The Sam Hartman Story: Dreams To Draft | Exclusive Interview

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Brief Summary In this rich and reflective conversation, Jeff Dudan welcomes Tom Rowland—legendary Florida Keys guide, television host, and podcaster—for a deep dive into life on (and off) the water. From humble beginnings in Chattanooga to fly fishing in Yellowstone, competing in elite tournaments, building a 20-year television brand, and becoming a wellness role model, Tom shares how his passions for fishing, fitness, and family shaped a purpose-driven life. With stories of big fish, bigger storms, and even bigger life lessons, this episode is both inspiring and grounding. Key Takeaways From Room Attendant to Fishing Icon : Tom’s journey began cleaning toilets in Yellowstone—just to earn free time to fish. That decision changed his life. Tournaments Were His Fast Track to Mastery : The pressure and competition of professional tournaments accelerated his learning curve beyond anything else. Fitness Is the Foundation : A 4:30 a.m. training schedule, Wim Hof breathing, and sauna sessions form the backbone of Tom’s longevity and mental clarity. TV Success Didn’t Come Overnight : The first season of Saltwater Experience bombed. But Tom pivoted to a two-host, no-voiceover style that’s now iconic. Water Quality is Florida’s #1 Issue : Tom gives a masterclass in the ecological crisis around Lake Okeechobee and why supporting clean water initiatives like Captains for Clean Water is vital. "You Can Do It" Is the Whole Message : Whether it’s switching careers, starting a show, or trying fitness at 50—Tom’s entire story is living proof.

Brief Summary In this powerhouse episode of On the Homefront, Jeff Dudan sits down with serial entrepreneur, author, and business builder Brandon Dawson, co-founder of Cardone Ventures. Together, they explore Brandon's journey from family business struggles to ringing the opening bell on Wall Street, scaling businesses into the billions, and building a new generation of empowered entrepreneurs. Packed with no-nonsense insights on equity, family dynamics, AI, hiring, platform businesses, and building legacy—this episode is a masterclass for anyone serious about scaling their impact. Key Takeaways Most Founders Never Make It to CEO : The journey from founder → entrepreneur → CEO is rare, with fewer than 0.002% of businesses ever reaching true CEO-level operations. Don’t Take Capital Too Early : Instead of outside capital or debt, force your business to be self-funding. Build the discipline first, scale later. Mentors Are Not Friends : Brandon breaks down the difference between learning from someone and needing their approval. You don’t need to like your mentors—just learn from them. Family Businesses Need Structure or They Collapse : Success requires transparency, accountability, and removing family if they’re not contributing. Use AI & Automation or Fall Behind : Businesses not deploying tech to streamline sales, marketing, training, and operations will be left behind by PE-backed or scaled competitors. Collaboration > Partnerships : Don’t give away equity. Align people through shared goals, incentives, and collaboration instead. Build Legacy Through Others : Real freedom comes when you help others succeed personally, professionally, and financially. Featured Quote “You’re not building a business until it can feed itself. Until then, you’re just hustling for survival.” TRANSCRIPT Brandon Dawson’s Unlikely Rise: From Pastor’s Son to Wall Street Jeff Dudan (00:01.195) you want to share about we do kind of the hero's journey. We don't have to dwell on it, but maybe I'm going to. Brandon Dawson (00:05.806) Yeah, I think you just jump. I think you just jump. Let's just go for it. And, and you can ask me and it'll come. Jeff Dudan (00:10.315) Yep, you got it. Brandon Dawson, welcome to the home front. Brandon Dawson (00:15.726) Yeah, thank you. Great to be on your show. Jeff Dudan (00:17.259) Yeah, super excited about it. Your book is the first one that I ever listened to on tape. I was traveling yesterday, so I didn't realize your voice was this deep. It sounded really high on two times speed. So I'm glad to, yeah, but it was really great. We have very similar backgrounds growing up. I think if we added our GPAs together, we still fall short of like five. So, but yeah, 100%. Brandon Dawson (00:29.226) Yeah, that's awesome. Yeah. Brandon Dawson (00:41.518) Makes sense. Jeff Dudan (00:44.523) What can you share about how you grew up and how that shaped who you are today? Brandon Dawson (00:50.606) Yeah, great question. Well, I was in a little town in Corvallis, Oregon. My dad was a pastor. My mom was a nurse and she and my dad divorced in 1976 and she met a gentleman who is an entrepreneur invented the in the ear hearing aid. And so he was running around the country trying to convince people to try to buy it, even though they didn't work real well. And she and my dad divorced. She ran off to Minnesota with him and took me with her. So when I was eight years old, I moved to Minneapolis and I watched this little tiny lab from the vision of an entrepreneur grow to when I left there in 1995, it was a $375 million global company that had gone through several iterations of ups and downs. They went through a nasty divorce in 91. I was still there working, running North American sales. And so between going back and forth to my dad and my stepmom, that were your traditional kind of middle America family, and then being in an environment with an entrepreneurial family with my stepdad and my mom, I really got the true context of rich dad, poor dad, thinking and doing. And I knew as a little kid, I didn't want to live in Corvallis, Oregon. I wanted to go build something huge, something cool, and I got my juices going. And once I graduated high school from Corvallis, Oregon, I was out of there. And that was the start of my journey. Jeff Dudan (02:27.915) You got into a family business and very quickly made a name for yourself as a top producer. And it's really difficult when you get inside of a family business because everybody thinks everything's handed to you. You got to work extra hard to prove yourself. People still don't believe it. There's a lot of resentment inside of that. We're a family office, family business here. And we have a lot of family members working in the business, some of our young people. What experience would you share? for people that feel stuck inside of a family business. The Family Business Trap: Resentment, Rewards, and Reality Brandon Dawson (03:01.422) Yeah, well 93 % of all businesses under $125 million in revenue have family orientation is what I call it. So there's somebody in the family working in the business and 97 % of all those businesses will fail every 10 years. So it's very difficult because when the family business fails, usually the family suffers and then when the family suffers, the community suffers. So I clearly understand this idea that when you're in a family business and you're expected to do more, for wanting less and not complaining, I get that that's a majority of the mentality of family businesses. When I grew up, I had all my older brothers working for me and I had fired them all at some point in time. So it is very difficult. In fact, it really helped me get stronger because I felt like if I can do that with my own family, my older brothers, I can certainly do it with strangers. And so, What you need in a family business is you need targets, you need resilience, you need transparency. And it is true that most older founders that have kids in the business treat them disproportionately to even their lazy employees. And so what I would say is every business should be structured properly to recognize the contributions of the people contributing. There should be reward mechanisms. And if you're family or not family, you should follow that exact process. And if you are family and you're not, you should be replaced because otherwise the good employees will think there's no opportunity for them because you're allowing mediocrity to exist in the business. And these are the things that are very difficult for family businesses. And generally speaking, they'll screw all that up because they don't want to play with the politics or dynamics. They either screw their family up or they screw up the business. Jeff Dudan (04:39.211) That's right. Jeff Dudan (04:50.059) Yeah, they don't they room they don't want to ruin Thanksgiving is it your experience that family businesses or are more reluctant to find a bigger room to get outside you know we always go find things like strategic coach or these other networks that people get involved with to get around other business owners that are up to something and going somewhere and Right. Brandon Dawson (05:13.998) Well, I mean, that's the premise of our whole business, right? Like we have tens of thousands of business owners cycle through our events every single year and millions participate online with us. But to answer your question, birds of a feather flock together. 99 or 98 .3%. So 1 .7 % of all businesses under 125 million ever break $3 million of revenue. The average business at three million has 12 employees. And that's where they sit. They sit there forever until the 10 -year cycle, until their profitability gets eaten up with cost and taxes and expenses, and then they go out of business. And so it's unfortunate, but what happens in a lot of family businesses is they don't want to put pressure in the system because they don't want to deal with it at home. They don't want to hold their kids or their spouses accountable. They're tired of fighting about everything. So they just exist. until it doesn't work anymore and it's very unfortunate. Now, contrary to that, when you learn to align your business, for example, Cardo Ventures, we're a high performance organization, started this business exactly 60 months ago after partnering with Grant and Elena, a husband and wife team. My wife is the partner and co -founder of Cardo Ventures, we're a husband and wife team. My brother runs sales, her brother runs technology. And so when you have the right rules in place and expectations, Everyone can thrive, not just survive, but thrive. But when you're placating to people and when you're holding certain people accountable and others not accountable, you are ripe for problems in your business. So I always tell business owners to have family. Treat everybody when they walk through that door in the proportion that they contribute to the organization. And it's easier to remove family that's not working because then the rest of the business will work. And those family members will move on and find things they're actually passionate about instead of feeling obligated or stuck to work for the family business and being disappointed they don't feel they're being treated fairly. Mentor vs. Friend: Why You Must Learn to Separate the Two Jeff Dudan (07:19.147) You make a very interesting distinction between mentors and friends. Can you speak to that? Brandon Dawson (07:24.622) Yeah, a mentor is somebody that you're specifically learning and developing from. That has nothing to do with being a friend with somebody. So when you're friends with people, you're co -contributing to each other, personally, professionally, financially. When you're mentoring from somebody, you are specifically learning and developing in areas of opportunities for you to succeed. You don't need to know your mentors. You don't need to like your mentors. Your mentors don't need to know you. They don't need to like you. They don't need to know anything about you. A mentor is someone that you learn and develop from because you're inspired by something that they can help you with. And if you really learn your mentor's information and bring that to fruition, bring it to life, you probably will meet your mentor at some time who will want to be your friend because you exemplify what they're teaching if you handle yourself properly. But there's no... There needs to be clear understanding. There is no commonality between a mentor and a friend. Those two things are entirely separate and they have nothing to do with each other unless you're able to develop a rich enough relationship with a mentor that then they become a friend. And this is what I've spent a majority of my life doing and I talk about it in my book. Almost every single mentor that I had, I didn't know because I was reading their books or I was somehow otherwise found them. But all those mentors became dear friends, some of them family, and collaborators, because of the contribution they made to me, me always telling the world I learned this from them. A lot of people aren't willing, because of the egotistical aspect of the human nature, when they learn something new and they're quoting it, I'm an expert in leadership, and this and that, they don't talk about where they learned it from. So if I'm somebody that's teaching something and someone's using my words, and I know that I've talked to that person or they've read my book and they're not quoting me, then when I do meet them, I have less of an aptitude or less than the appetite to actually get to know them because I feel like they're not, they're not giving back to what I did. Jeff Dudan (09:30.187) Yeah, it's really clear when you pick up a book and it's just a collection of things from other people's book that are put together as opposed to the authenticity that comes across in your book, sharing your stories, sharing your experiences, and really giving people a blueprint and a framework with which they can inform their lives and their journeys. Acquisitions, you built a company very, very rapidly through acquisitions. You got out over the tips of your skis a little bit with the board. And now what you learned in that process has led you down a very interesting path in building businesses through collaboration. Can you talk a little bit about how important it was and what you learned in that acquisition process that spoke into what you're doing today? Brandon Dawson (10:18.638) Yeah, great question. You know, a lot of I have and I know you have experience with this on both levels, both being the acquirer and capital raising and all these things. So when I was 26, I went the traditional route. I went out and made hundreds of presentations, got my first million, then raised six million, then raised 28 million with Warburg Pincus at 29 years old, rang the opening bell of the American Stock Exchange. Jeff Dudan (10:30.155) Yes, sir. Brandon Dawson (10:44.686) as a high school graduate, voted least likely to succeed. All those were things that I was told would never happen, and I was able to make them happen. The problem was buying 130 businesses and shoving them together to try to create a platform company. And for those that are listening, they're like, what's a platform company? A platform company is what Wall Street talks about that has 10 specific elements. It's an organization that has a strategy, it has proper promotion and marketing, it has proper sales conversions, it has... proper people alignment mechanisms, it has proper operational protocols, it has proper leadership, it has proper data that it knows what it's looking at and what it's doing, it has proper technology and systemization, and it has proper investment thesis that fits the strategy. And in order to afford all that and to be successful making 20, 30 % of profitability per year, you're gonna have to be between 100 and 150 million dollars of revenue. or you can't afford all that and the expertise associated with it. So a platform company is a company has all those resources, all those assets, all that leadership, all pulling the business in one direction towards a stated objective to execute and drive value. Okay, that's what a platform company is. A platform company isn't a 10 million or a 20 million or a 30 million dollar business because you're not big enough yet to have all those things. So understanding what a platform company is. and I understood what it was because my mentors told me so I was on a race to build a platform. And I had to do it by buying hundreds of little tiny half a million million million and a half dollar businesses and trying to shove them all together and create all the leadership team and create all the systems and create all operating protocols at 29 years old with no formal education. So if there was a recipe for disaster, I was it. But because I was able to survive and push through, I had this false sense of I can overcome everything. And that caught up to me. Actually, the business started doing unbelievably well. We were going to be the largest in the world. People were throwing money at me. But my investors of five years, Warburg, the professional investors, were watching me thinking any minute this guy could drown, right? Any minute he can make a technical mistake. Because although I was in survival mode, feeling like I conquered, they were in, my god, this guy's in panic mode all the time. So. Brandon Dawson (13:02.062) when there was an opportunity for them to exit, take all their money, plus 100 % of their money, plus, plus, plus, plus, plus, leaving me and my investors with nothing, they took it. At the time, I was bitter and upset about it, but in reflection, if I was them in today's state, I would do the same thing because I was just very fortunate that I survived. I was missing the strategic and leadership and investment thesis side, and I just looked like a reckless doer. when I go back and look at myself at that point in time, right? So everything in business is two things when you're building a business, context and contrast. And until you have wisdom and experience, it's very difficult to have context and contrast. But I would never trade all those experiences because they were unbelievable. And the one thing it did say to me is I can overcome whatever's in front of me. And so what I wanted to do in my next iteration of business is retool how businesses are built. And that set me on the course I'm on today. Jeff Dudan (14:03.595) You had unusual vision at a young age. thinking about that acquisition strategy, building the platform, had to be informed from what you learned and what you saw in the business that you were a family business from growing up. And said, I can do this bigger, better, faster. I can do it differently. And today, you work with business owners. I saw one podcast where you had somebody on there that came to you pre -revenue. And it was an engineering firm. So you work with businesses from zero, probably up into the hundreds and hundreds of millions of dollars at Cardone Ventures. When you... Brandon Dawson (14:36.942) Billions. Jeff Dudan (14:37.739) Yeah, billions. So when you think about the smaller companies that come to you and ask for help and ask for partnership, when is it appropriate for them to take on debt? What have to be the conditions in the business for them to take on debt versus perhaps raising outside capital? Brandon Dawson (14:56.014) Yeah, it's a great question. I always recommend they do neither. So what we teach businesses is to do what I did with my last company that I sold for 77 times EBITDA, and that is force the business to be responsible enough to fund itself. Because here's the thing, 97 % of all businesses fail within 10 years. So if you're raising money from third parties outside investors, you're going to have all the pressure associated with demands that you will struggle meeting because you're just going to struggle in general building a business that works. In addition to that, Jeff Dudan (15:11.947) Yeah. Brandon Dawson (15:31.758) When you raise money, the first money you raise will always be the highest valued money statistically because the next round you raise is because you're not working the way you said you're gonna work and then you're gonna get crushed. So instead of putting any energy into that, because I know a lot of entrepreneurs, they're just professional fundraisers and this whole concept that Wall Street pedals of deficit financing, you know, raise capital and sure, Uber, it worked for Uber. It worked for Amazon. Bezos was made fun of for not making money in today's richest guy on the planet. Okay, so yeah, so there's a few scenarios where that works. WeWorks is an example where it didn't work, right? So even though the founder made out better than all the shareholders, everyone else lost money. So at the end of the day, the best, safest way for the average founder, now this is different, a founder is different than an entrepreneur. Jeff Dudan (16:04.651) Yeah, he can deal with that. He's fine. Jeff Dudan (16:12.011) That's right. Brandon Dawson (16:29.262) and an entrepreneur is different than a chief executive officer. And so anybody can be a business owner founder. But you don't become an entrepreneur until you recognize the significance at the 15 to 25 million mark when you actually realize, wait a minute, I need a strategy. Wait a minute, I need leadership. Wait a minute, I need systems. That's when you move to being an entrepreneur because you start recognizing the things the business requires in order to succeed. A CEO is someone who's chartered with creating massive value, aligning, incentivizing teams, hitting targets, defining the business objectives and strategies, and knowing where to properly invest in the organization in order to create massive value and hit internal rates of returns. That's a professional CEO. A lot of founders call themselves CEOs, but they don't even know what it means to be an entrepreneur yet. So founders tend to be, founder business owners tend to sit in that one to two, 15 million range struggling to survive every day. And so what I tell business owners is you need to know your place and you need to know the difference between the specific differences in competency, contribution, and abilities. And you need to be honest with yourself because if you don't, you're gonna surround yourself with all the wrong people. So you ask a question which is, When is a good time to bring on capital? Well, the best time to bring on capital is when you can prove, because remember the chief three complaints for why businesses fail. Chief complaint number one is no demand for product or service. You should never bring capital into the business if you haven't yet vetted the demand for product or service. Chief complaint number two is can't find any good people to help me. Well, until you prove that you know how to be successful with your products or services, you're never gonna find good people because good people don't work for shitty business owners. So it's a natural law of progression. And then three, can't get access to capital or money. Well, what moron's gonna give a founder money that can't hire any good people because they themselves can't prove demand for product or service. So it's all excuse for actually not vetting what the true business opportunity is and not owning the responsibility of actually building a business. A business is a thing that has its own life, that is able to grow up and feed itself. It has a purpose. Brandon Dawson (18:50.03) It has mission, it has vision, it has values, it has intentions. And so I tell business owners, the best time to bring on money is when you know how to generate 20 or 30 % profitability, you know how to scale and grow your business. You built a great management team. You haven't given any of your equity away. That's a good time to bring money in, in order to go through rapid expansion. Until then, statistically, you're going to die. Why take all your friends with you? Jeff Dudan (19:12.556) Yeah, that's such a great answer. That is, people need to listen to that. That was really incredible. Brandon Dawson (19:20.718) Well, you're in the business too. How many people tell you, I just need capital. I just need capital. I just need capital. It's the default thing because in their mind, if they just had money, they could solve their fact that they can't even build a basic business and demonstrate it works. So like do that first. Jeff Dudan (19:26.507) every day. Jeff Dudan (19:39.179) Yeah, and then I think at the other end of the scale, and we see it with some of these great national brands that have gone bankrupt, they go through a transaction, they get levered up on debt with the promise of using that debt to expand the business. But again, they haven't vetted out the products or the service. The plan doesn't work out. You try another CEO, and the next thing you know, you're in trouble. and you've got so much debt on your business, interest rates go up and now you're in trouble. Where great businesses, I mean how much cash does Apple have on the balance sheet? I mean just, you know, tons of tons of tons of cash. So the fact that these businesses need to grow up and feed themselves, I think that's a great analogy for what founders and entrepreneurs really need to think about. Brandon Dawson (20:27.342) Well, and I'll be honest with you, and you know this, you're a successful business owner and you talk to a lot of people. You're gonna sleep so much better at night when you have a little money in the bank. You don't have the gun to your head. You don't have people yelling at you. Even if you're not growing at the speed in which you wanna grow, if you're sleeping well at night and you're able to achieve your personal, professional, financial goals, you've got a team that's able to achieve their personal, professional, financial goals. The business has the discipline to self -fund. you're just gonna have a much higher quality of life. And so the first reason to not take on debt and not use other people's money with the concept of trying to build something is you're probably gonna fail and you have to live with all that liability. So go slower at the beginning, structurally build it correctly, learn the rules of starting building, optimizing, scaling, and then exiting a business. Learn those rules, this is what we teach. And then just, Do it a little slower until you figure out the algorithm for doing it. And then build a great team of people who enjoy working with you, that you can be passionate with, that are highly aligned for execution, not being mediocre and incentivized to flourish and prosper. Prune the orchard once in a while when it's not working, keep the core discipline in place, go prove out what you're doing, and then hit the accelerator. after you've built some cash reserves. So if you're wrong, you can afford to make the mistake and you just retool and go back to where you level set and do it again. That is ultimately gonna be a much, for pro survival mode, that's gonna be a much better way to do it than just trying to chase everything as fast as you can using everybody else's money only to suffer the consequences of the statistics that 97 % of all businesses fail within the first 10 years. Jeff Dudan (22:17.387) Yeah, that's right. And losing other people's money is a bad look. Brandon Dawson (22:20.814) sucks. Jeff Dudan (22:21.899) Yeah, so you just walked us through a mindset progression where founders to entrepreneurs to CEO. So Cardone Ventures works with people and you have tools and you have processes and technologies that you put in place. How do you communicate how to these people, how they should think bigger and think in a more disciplined manner? Brandon Dawson (22:47.246) That's a great question and really the art and the reason I wrote this book is because sure I have a bunch of operating system books right like like we have documented there's to go from zero to a platform company 125 million there's 10 specific elements 76 sub elements and 240 specific things you need to do okay so that's all been documented we teach on it every day across every single one of those 10 elements in the sequence in which you need to do things if you think of your business as the thickness of a pad of concrete. and you start your business thinking you're gonna build a one story building and then as you, and that would be to three million statistically. And you get to three million and you're like, man, this was good, I'm gonna go for eight million, but you don't increase the thickness of the structural pad. After you add a second and third floor, you're gonna collapse. So there's three to five things that you must have in place at level one through level seven, and that's zero to 125 million. There's actually 11 break points to a billion. Jeff Dudan (23:30.571) Hmm. Brandon Dawson (23:45.39) And so as you're building your, so think about it. If I came to you and said, engineer me a 10 story building, 12 feet each, 120 feet high, and you do the engineering work, you build the blueprints, I pick the interior design, we pick the exterior design, we go through this whole process and then we start building. Well, that is entirely contrary to how the founder builds the business. And it isn't until you run through a couple cycles as a failed founder that you ask the question, what do I need to do differently next time to be successful? And that's where you move to entrepreneur. Now, if you can bypass the failures at 15 to 25 million, you're going to be sitting around going, how do we get bigger? How do we make more money? And someone's going to go, eventually, you know what we need? We need a strategy. And you're like, strategy. We just have always just done, and it worked. And so you grow into being the entrepreneur. Like, we need to think further out. We need to have better things in place. We need to find, attract, align, develop, and retain great people. You start to move into that out of necessity. And if you don't, you will collapse and fail, right? So there are three to five things at each break point, zero to three million, three to eight, eight to 15, 15, 25, 25, 45, 45, 75, 75, 125, all the way up to a billion, there's 11. If you know what elements need to be in place, now what you need to do is ask yourself the question. So this is the fundamental question. Do you have the patience to build? Because there's a few things that you need to equip yourself with. to move from founder to entrepreneur to chief executive officer. And those things you need to equip yourself with is the patience and the resilience to learn context, contrast. If I do this, what can I expect is gonna happen? And if I do it wrong, what will probably happen? And you need to be patient and move delicately. Jim Collins talks about innovation as incremental improvement on the things that you can prove work. So first part of innovating is proving what works. Or you can apply radical innovation, which is what Elon would talked about, which is just invent something new and go all in on it. There's a few people that have been successful doing that, but most fail. So in small business, you need to apply the Jim Collins definition of innovation, granular incremental improvement on the things that you can prove works. Slowly, systematically. Brandon Dawson (26:11.598) within the rules, and then you build. Well, if you follow that principle, you're gonna be successful because you're not gonna have big radical shifts because you're not doing big radical things. You violate those rules and you start trying to do big radical things, chasing revenue, statistically you'll collapse. So what happens is you engineer as you go, but if you don't recognize the fact that you're on the third level or fourth level and you have not reverse engineered, you've not structurally engineered, and you haven't gone backwards to say, what did I miss that I need to have in place? You will eventually implode. And this is what happens to 97 % of all businesses in the growth cycle. So you're either going to break through to the next level or you're going to break. If you break back one break point, it's a slip back. If you break back two break points, it's a snap back and it's catastrophic because you can't catch yourself in the fall. So there's just all these rules. And what we do is we teach business owners these rules. Now, the fundamental question that we talked about is, do you have the patience to learn context, learn contrast? Do you have the resilience? Are you willing to do the hard things, like family and moving people around and realizing you put the wrong people in the wrong place and you're paying them too much, you're not paying them enough? Do you have the resilience to make good decisions? And then fourth, do you have the wisdom? And then fifth, do you have the aptitude? Do you really want it? Because boy, if you don't really want it, it's going to be so hard. You will conform to mediocrity and sit wherever you're at until your costs exceed the benefit ratio of being in business and you go out of business. Or you sell. Jeff Dudan (28:01.995) And then P makes all the money, which happens, I see happen all the time. People spend 25 years, 25 years building a business, they sell it for nothing. The people that know what they're doing come in and two years later they sell it for 10 times what they paid for it. And it's not that difficult. Well, know what it is, because I'm gonna reference your model of founder to entrepreneur CEO. I would suggest, and I'd love to get your feedback on this. Brandon Dawson (28:07.214) Dude, you and I. Yeah. Jeff Dudan (28:30.827) Without a card on Ventures Playbook, as you described, 95 % of founders will not transition to entrepreneurs. And I would say another 95 % of entrepreneurs are not going to transition to CEO. True? Fair? Brandon Dawson (28:46.766) I would say the stats are higher because remember 98 % of all businesses are stuck at 3 million or less if they're under 125 million. So only 2 % break through the 3 million zone. So you get to the micro percentages at 15 million to 25 million. So I'd say 0 .05 or 0 .08 get to the entrepreneurial stage and 0 .002 get to the CEO stage. Because how many entrepreneurs do you know? or founders do you know that built businesses greater than 75 to 125 million and stuck with it without bringing in the professional leadership team to run it? Jeff Dudan (29:20.875) We acquired five businesses in 2022. And we spent the entire year platforming them onto a business platform, a franchise business platform. We went out and hired the best C -level executives that we could. We launched to the market in 23, and this year we'll do somewhere around $98 million with those businesses. And. Brandon Dawson (29:38.862) Yeah, because you're an entrepreneur, dude. You're not even the CEO. You figured something out. Here's the funny part. When you say that, like you and I are going to laugh at this, the people listening to it need to hear this because you and I have never met and we've never talked. But we're speaking exactly the same language because here's what you and I are. We're entrepreneurs that are investors. We don't want to do the work. Jeff Dudan (29:43.307) Right. Jeff Dudan (29:56.331) Right. Jeff Dudan (30:00.587) Yes. Yes. Brandon Dawson (30:03.182) There's no reason for us to be the CEO. We don't need that control. We just need to know we put the right people in the right place, doing the right things the right way in order to hit the right targets. We're entrepreneurs who are investors. We see opportunities, we go acquire the opportunities, we build the things that I mentioned to take care of all the bullshit that we're not going to want to do. Not that we can't, we just don't want to do that. We've been there, we've done it. So we do it differently. And I think that's the difference is that you are an entrepreneur investor who can be a founder, who can be a CEO, but you and I both know it's not the highest use of our contribution and we're better off finding great people and giving them that opportunity to succeed and doing more of those things. So what you just described for those listening is he is an entrepreneur investor that knows the requirements to build a huge business. Jeff Dudan (30:46.091) That's right. Brandon Dawson (31:02.318) and knows the people that need to be there to do the right things. He's building teams, finding opportunities, placing people in there, giving them the opportunity to accelerate and thrive and conquer. And then he's going to go get the next deal because that's what smart people do. By the way, it's a $12 trillion space, that small business space, and 5 trillion of it is looking for an exit that can't find it because they're not profitable. And you're running around picking off all those businesses. and then bringing life to them for the people that are sitting there underneath the poor owner that can't figure out how to grow it, and they probably love you for it. Jeff Dudan (31:35.211) Yes, we're closing in our sixth brand today. The docuSigns are in my box as soon as we're done. And by the way, it's my birthday. So I think that's Serendipity 56 today, closing on our sixth brand. And I will, was that right? Well. Brandon Dawson (31:41.934) Happy birthday, dude. Yep. Brandon Dawson (31:47.15) You and I are the same age, man. We're one month apart. Yeah. Mine's May 22nd. We're two weeks apart. Jeff Dudan (31:52.363) happy birthday to you. And of those six brands, only one original founder remains active in the business. It just, it didn't work. It can't work because it's the, they get the bends. Brandon Dawson (32:05.07) Dude, one of two things, I hope you're, one of two things, you know this, and you're listeners, look, again, I'm gonna qualify this, you and I have never talked, this is the first time we've ever had a conversation, true? But we know something, we know that there's only one time a business works, and that's when it's kind of working. Because when a business, when you acquire somebody's business and it doesn't work, they're gonna be disenfranchised and they're blowing out on you. Jeff Dudan (32:16.843) True. Brandon Dawson (32:30.542) When you buy a business and you blow it up and it becomes more valuable than it's ever been, they're pissed off at you because they think that you screwed them over. When the reality is they just couldn't figure out how to do it, which is why they sold in the first place. So the only time a founder actually works in a business after you acquire is when it's just kind of going along and they haven't been able to get enough money to score. So they're willing to drug it out or fight it out. There'll still be a pain in the ass in most cases. But the only time it works is when it's just kind of working because when there's too much money or not enough money, it's always gonna be a disaster. Jeff Dudan (33:01.003) Yeah, that's fair. Okay. Can we talk a little bit about the future trends? I would love to get your perspective because I think you're probably thinking five, 10 years ahead of me and everybody else that's listening here. Marketing tools, 24 months. I've been on the road 16 of the last 30 days talking to, looking at, figuring out like what... the marketing stack and customer lead generation stack at tomorrow looks like. And some people have really figured it out and they are blowing up their businesses and other people are trying to figure it out. The risk of not figuring it out, not incorporating these tools. I mean, if I owned a marketing agency, I would be, I couldn't even, how do they even keep up? with everything that's going on and serving all their clients and stuff. What's your view of marketing tools, automations, technologies, and the impact on people, things that people used to have to do that they no longer have to do? And how are you leveraging that? Brandon Dawson (34:10.158) Yeah, and this is where small businesses really needs to like open their mind up, right? Because there's seven promotions in a business, you know, promote who you are, promote what you do, promote why you do it, promote your impact in the community, promote why somebody should join your team, and then teach everybody the six promotes. That's the seventh promote. Now, how do you promote? You promote through digital strategies, paper strategies. You and I are 56. Back when we were 20, we were running around handing flyers off and sending newsletters to people and doing all that bullshit. Today, you've got a full automation stack that AI should be able to make the outbound calls, should be able to qualify the leads, should be able to schedule them into the appointment, should be able to confirm the appointment, should be able to listen to you actually communicate when you have a live person either on site or over the phone and score how well you're doing it and then immediately give you feedback on did you fit within the 90th percentile of being the best version of what we know works or are you in the... 70th or the 50th or the 30th and it should automatically Institute training protocols and you as the owner should just get your alerts green yellow red red means somebody's entirely Butchering the process yellow means they could use some work mean green means they're great and they're your top performers So so now the question is okay does that even exist and the answer is yes And not only does it exist but it can do it in every language in this world and do it in real time And so then somebody's like wow does that? Is that real? Yeah, but it has to be structurally built because here's the thing. The only reason marketing doesn't work, if you think about there's this funny thing that, and you'll appreciate this because I know you're already looking at it in your due diligence. So you and I have never talked. I know you look at it. Recurring revenue, what percent? If a business has been in business for five years, 65 % of its revenue should come from a second, third, fourth, fifth, eighth sale to somebody they already built a relationship with. 35 % should come from. new relationships. If the ratio is 80 -20, 80 new relationships, 20 % recurring, it's a broken business and they're spending 10 -15%, 20 % marketing because their operations suck. Okay, so if you know that and you understand what your targets are, now I don't mean to tip off these businesses that are like, how do you guys know if we're good or not? There are certain things that a guy like this and I will look at immediately and we'll know if you're good or not. Brandon Dawson (36:26.83) even if you try to trick yourself into thinking you're the best. So here's the thing, automation, AI. will work to the extent that you're committed to operationalizing the best practices across the total spectrum of everything you do, and you're willing to hold the manual teams, the physical team members, the people you're inter -reliant on, to the extent you're willing to hold them accountable and incentivize them to do the right things at the right time in the right way. Okay? You can have all the technology in the world, but if you're not gonna be able to do that with your team, you're still gonna fail as a business. So technology for businesses that embrace the systemization, the automation, and the intellectual capacity of what all this technology can do for you, if you're willing to embrace it, that's great. But to the extent that you're unwilling to initiate the discipline and accountability through the manual delivery of it, you'll still go out of business. So to me, I think that technology is creating this unbelievable, and now if you're competing against a large institutional owned business and you don't embrace the idea that you need to embrace these tools, deploy them in your business, align your team with them and hold them accountable to doing the right things at the right time with the right people, you're gonna go out of business. And the private equity guys, There, you know, I go to Alaska and I go to Alaska and fish with my buddy and we're in the back of the boat jigging for salmon. Then the big troller comes by, right? And you see him throw all hundreds and thousands of fishes in there. And then they're throwing off the ones that you're like, man, I would love to catch one like that. Boy, I haven't got a bite for five hours. They're throwing out fish. I'd love to catch. Well, because they have the benefit of having a net so wide, they are looking for something so specific. The rest of it, they don't even think about it, right? Versus you're just sitting there jigging in the water. Jeff Dudan (38:25.643) Right. Brandon Dawson (38:28.046) Well, if you're the business owner who's just jigging in the water, private equity or the guys coming by and trolling through or your big competitors are just throwing back the stuff they don't want and keeping the absolute best of what they do want. If you want to be the best and the most valuable, that is a commitment that a business owner needs to make. And then it's a pursuit they have to stay committed to with all the resilience in the world or their. They're working harder, not smarter, and they're not able to create value for their team, so they'll never have the best people. Because once your people find out you're not paying attention, and you're not pursuing excellence, you're top performing people. We'll go to those other groups that are growing fast, because fast growth is exciting. Fast growth that recognizes talent is rewarding and exciting. So if you're not that person that's talking about growth, talent, and rewards, through operational effectiveness, you're in big trouble. No matter how much technology you think you can deploy, if you can't align your team with it and execute to it, you will be left behind. Jeff Dudan (39:38.091) It feels like entrepreneurship is accelerating at an accelerating rate. There's so many sophisticated collaboration companies out there, such as your own, that have really figured out how you can get into win -win -win alignment with companies. And I see companies, particularly in the blue collar spaces, like we operate, we're property services, some companies just seem to be hitting the nitrous in the car and just accelerating away from the pack. So the bigs are getting bigger. There's roll ups that are happening out there that puts more pressure on the small business owners. Yet entrepreneurship, it seems like even at the side hustle level, the blue collar level, online, you know, influencers and marketers and Amazon shops, it just seems like entrepreneurship is really alive and well and expanding and accelerating to people that had never really thought about it before. What's what's your view on that over the rest of this decade here? Brandon Dawson (40:38.062) Yeah, well, there's 12 trillion of existing businesses in the small business space. Five trillion are looking for a back door. It's really, there's never been a better time to want to be an entrepreneur. You don't need to start it from scratch. You can just walk into somebody else's existing brand and business and make it better immediately. And, and it will be self -funding, but you need to learn the skill set and the talent to do it. I think it's important for business owners to understand that Gallup Pull does a survey every single year. And in that survey, a hundred million U .S. workers respond. Two -thirds say they're disengaged. 18%, 18 million of the US workers say they're actively disengaged. They're sabotaging the company they work in. So really, if you have 10 employees, three are actively engaged, aligned with you. You better make sure you know who those three are and you're leaning into them. And you need to get rid of the bottom two or three and replace them. And then just continue to have that mindset. Because if you're looking at your workforce right now and you're like, wait a minute, I haven't added anybody or fired anybody in five years, two -thirds of your people are disengaged or actively disengaged. They're sabotaging you. Jeff Dudan (41:20.843) That's right. Brandon Dawson (41:36.814) and three or four are gonna leave because they're like, man, nothing's happening here. We're gonna go take advantage of this entrepreneur wave that's happening because who becomes an entrepreneur? Well, here's the funny thing. We interviewed. So I did all this research in 2009, 10 and 11, and it's interesting because many of the blue collar businesses back then, HVAC, garage doors, electrical, plumbing, they were considered low valued EBITDA businesses. So a $50 million blue collar sheet metal building business would have been worth. four to five times EBITDA back in 2009, 10, 11. Today it could be, well, two years ago it would have been 12 to 15 times. And that's because where technology was deployed and where you have a business that becomes a front door to other things happening, you're worth so much more now because of the recurring revenue and the automation, blah, blah, blah, all these things that allow that to happen. But here's the thing. There's so many businesses, 96 % of businesses, I'm sorry. 86 % of business owners self -disclose that the reason they started their business became entrepreneurs is because they didn't want a boss, they didn't want to be told what to do, they didn't want a limitation on their earnings, they didn't want to be held accountable, and so they started their business because of what they did not want versus those that started for what they do want. So when you talk about the ability to flourish and prosper as an entrepreneur, The three people out of the 10 that are working in somebody's business who are watching this dysfunction happen, the reason they go start a new business is because they don't want to deal with the bullshit anymore. So they move somewhere where they can be in control and you lose your good people and then you're really in trouble, okay? So could there be an amazing boom? of forward thinking entrepreneurs. Well, when you go start a business, you're already like, I'm moving to something new. I'm excited about it. I'm going to get it going. If they can learn the technical aspect of how to do it right out of the box versus before they get disgruntled and before they get disappointed, before they're under stress, pressure and anxiety and fear and all that stuff, they could crush it. And we're seeing that with 20 some year olds because they're not stuck with all the broken thinking that they're experts. They go find help. We have so many people between the age of 18. Brandon Dawson (43:58.03) and 28 that are running 10, 20, $30 million businesses. I can't imagine a better time in the history of youth and entrepreneurialism than there is right now. Just remember that space of 31 million small businesses that do $12 trillion a year in revenue, they employ 67 % of the workforce. It creates 45 % of the gross domestic products, the GDP, the economy, and yet it's only represented 8 % on the stock market. So all those founders with all those employees that are killing it every day, they just never get the value. Imagine a world where you could learn how to turn the switch of value creation on like you have, and all of a sudden bring all those young, ambitious people that are, or older, ambitious people that are tired of the BS where they're working into your atmosphere. You pull them into your world and put them to work where they can pursue their personal, professional, financial goals. There's no rules. It's a wide open throttle. and you know the valuations on those businesses are going up every single year, so you know you'll have a huge accident at some point if you build it right. Man, I can't imagine. I'm 56, you're 56. Could you imagine the knowledge we have today at 26? Jeff Dudan (45:08.683) yeah, it'd be amazing. But you know what? Man, there's a lot of things we can do right now to stay good. So we got time. We got lots of time. Dan Sullivan with Strategic Coach. I don't know if you know who that is. One of his great books, Who Not How. Don't look for the who, find the how, like you mentioned a lot of these young people are doing. He's 80 and still just, you know, doing it every day. Whether it's a partner or whether it's a key person or a star employee, what are some of your favorite strategies for incentivizing and retaining these people? I know you mentioned P shares at one point, you know, really from structuring, you know, the ability to structure some collaborations and some deals like that. What would you speak to some of the people could use to really be more thoughtful about how they retain people and incentivize the right behaviors? Brandon Dawson (45:58.19) It's a great question and you and I both know that the top five reasons businesses fall apart between zero and 25 million is bad partnerships. People giving equity to the wrong people with the wrong expectations, getting the wrong results, and then the sabotaging and destroying their own companies because they're all caught up in the emotional aspect of that. So look, there's a proper way to incentivize people. You have long -term incentives, LTIs. You have short -term incentives, STIs. And what you want to do is you want to create Jeff Dudan (46:09.167) Yeah. Mm -hmm. Brandon Dawson (46:27.438) the motivators that drive value in your business, you wanna be able to give your team STIs, you don't wanna overcompensate. There's a bunch of problems that happen with compensation between 3 million and 25 million, and most people do it wrong. It's another huge reason at 15 to 25 million, they go through a massive break point, they lose a third of their best people because they realize they've been entirely compensating incorrectly. They switch the compensation, the best people leave, because they go find another business owner who doesn't know that yet. and they're able to go command the income they were earning and the business owner ends up falling backwards. So there's so many technical things that are as certain as gravity in business. And what I would say to people is if the equity that you want to have with all your employees is their personal, professional, and financial goals, if you can align and if you could listen to your human beings talk about the things they're most ambitious and excited about over the next one, three, and five years. personally, professionally, and financially. And if you could show them through their contribution in the organization how you're going to help them achieve those things, that is the equity in your business until you're about 50 to 75 million where you need the sophistication of bringing somebody that knows how to run a hundred million or 200 million dollar company into your organization and they're looking to make that move downward, they're looking for something they missed the last time. And so that's where you talk about real equity. And that has to be structured appropriately as well or end up screwing things up. So the equity, a business owner sub 75 million should really be thinking about with all their team members is how do you align their personal, professional and financial ambitions and allow them to succeed and accelerate and accomplish those goals through the business by contributing to the business, knowing when the business wins, they win when they win, the business wins. That's the best equity you can have. And then the technical equity. outside of that and normal compensation, you should factor whatever base you pay somebody, you should show them how they can make 50 % to 100 % of that base through driving value in the company. Then on top of that, have that goal setting mechanism I talked about. So I would say it's very important, but most people are giving equity to the wrong people when they're too small, they already don't know what they're doing, and then they have a disastrous cap table, and then it causes all the friction and resistance and it keeps them small. Brandon Dawson (48:51.278) I wouldn't even contemplate equity or partnerships in business. Statistically, those are all be the reasons you fail anyway. They're in the top five of all reasons you fail under 25 million. And so I would just try it. If you're going to start a business, collaboration with other people is the best. Let them have their thing. You do your thing. You guys work together. You add value to each other, but you own your business. They own their business. Collaboration is the highest form of currency. that you can have with people and I would just recommend that you try that first before you start giving your company away to a bunch of random people. Jeff Dudan (49:24.491) Great advice. Partnerships and sinking ships, avoid them both sometimes. We're heading towards the barn here, Brandon, but this has been Fireman. I really, really appreciate it. What would you say today is the number one way that you would like to define your legacy? Brandon Dawson (49:48.366) You know, I have in my career, I now have 290 millionaires to multimillionaires that I've been directly involved with impacting their life. I have another thousands of people behind that that I've helped hit their largest income goals they've ever hit in their career. I want to help 1 million 10x business owners achieve their personal, professional, and financial goals and because For me, that's somebody that wants to hit 50 to a billion dollars. So that's millions of human beings to this personal, professional, and financial planning strategy and compensation, long -term incentive strategy that we've created for the businesses we work with. I want to be responsible for millions and millions and millions of Americans or people globally. We just launched CardoMentors UK. I want to be responsible for millions of people. Like when I'm on my deathbed, I would love to be getting those messages saying, you changed my life by teaching me how to achieve something I'd never been able to do before and it's impacted my life, my family's life, my legacy. That's what I'm looking for, to be the ultimate. I don't wanna be the king, I wanna be the kingmaker. I wanna create million, multi -million dollar kings all over this world that can invest in their families, invest in their communities. invest in the things that will create value to other human beings. And that's what I want to be known for. It just so happens my talent and my skill set in doing that is is economizing businesses. Jeff Dudan (51:26.411) That's beautiful, man. That is a purpose worth doing, definitely. And we need it. I mean, we absolutely need it. Think about today. Kids can't buy a starter home for less than $400 ,000. People have more month at the end of their money because of inflation. Wages and things don't go up as fast as everything else has. And you're really starting to see the stress of this economic condition that we're in. And you got to give people a way to achieve their financial freedom, economic security, create generational wealth on Main Street USA for everybody. And I think it's a very important patriotic thing to do. It's important work that needs to get done. And I applaud you doing it. That's why that's our, you know, we have three purposes here. The one I just what I just said, and then we want to impact kids. So we're building reading rooms across the country in Title I schools because. The earlier in a manufacturing process you fix the defect, the cheaper that it is. So the more that you can pour into youth, I think is critically important. And then we support transitioning veterans through Operation Homefront. So. Brandon Dawson (52:28.974) Dude, we're right there with you. I just signed a partnership with 52 Ventures, Ray Lewis and the Grant Cardone Foundation and Cardone Ventures to start bringing all this technology and learning abilities into inner city kids and kids without fathers. Those are our missions. We have a huge vet space. I have a SEAL Team Commander 4 and I have a retired special forces very high up and I have a general or two. that we're launching a bunch of programs to give vets an opportunity to own businesses. So I'm right there with you and here's what I already know. I know that this is the first time you and I ever met. We did this podcast together. We're so aligned in how we view the world because of our experience, by the way. That should tell your listeners if they're like, well, how do I know I can do it? The only reason you and I are having this conversation and we're speaking the exact same language intuitively is because you'd learn by doing it. It's trial or error. You're either gonna do it with somebody collaborating. or you're gonna go figure it out yourself, which is the slow way to do it, to be honest with you, and it's the most dangerous way. I have a feeling that post this podcast, you and I are gonna connect somewhere and we're gonna end up investing in something or somebody together, or a multitude of things together, because this is what happens. Smart people wanna work with smart people. Good people wanna work with good people. The predictability of somebody's ability to be smart and good is based on historical results and what they're currently doing. And I would just recommend to anybody listening and watching this show, surround yourself with people that have proven they're actively doing it and they're willing to share how, or do it with people who are actively doing it and being successful. Just make sure that you're aligned emotionally, you're aligned. with the target, you're aligned with the mission, the vision, the purpose, the values. And if that's the case, man, go all in because you and I both know we've created so much wealth for people who work with us. They don't have to own the business. They can do it through us and with us faster than most people will do it by themselves. So I have to just say, look, get involved, go show up, educate yourself, get out of your mindset. This is what nine figure mindset is about getting around the right people. Brandon Dawson (54:49.134) Becoming an owl. Who can I trust? Who's doing it? Who can I do it with? Who else is doing it? Who can I learn from? Who's gonna do it next? Who do I need to talk to to get help from? Who, who, who, who, who? Become a professional owl. And I know either one of us would entertain that conversation with someone who is serious about wanting to succeed. Jeff Dudan (55:07.499) 100 % and I'm gonna make that happen. I'm gonna chase you around and figure out where you are and then we'll just happen to bump into each other. Last question here, Brandon. If you had one sentence to make an impact in someone's life, what would that be? Brandon Dawson (55:12.43) Let's go. Brandon Dawson (55:23.822) The true freedom of personal, professional, and financial success is through how many people you can help achieve that, and then you will find that freedom. You doing it for yourself isn't gonna get you there. Jeff Dudan (55:37.803) Perfectly said, perfectly done. This has been Brandon Dawson ripping it up with Jeff Duden on the home front. Brandon, thanks for being on. Yeah, right on. And. Brandon Dawson (55:46.318) Jeff, thanks for having me.

Brief Summary In this soulful and hilarious conversation, Jeff Dudan sits down with Casey Webb—actor, seasoned restaurant pro, and host of Man vs. Food. From his blue-collar upbringing in New Jersey to a late-blooming entertainment career, Casey shares stories of grit, grief, growth, and gratitude. The episode is packed with rich storytelling, laughter, and powerful reflections on family, purpose, and staying open to life’s adventure—one “yes” at a time. Key Takeaways "Yes, and" isn't just for improv—it’s a life strategy. Casey credits his improv training with helping him build a career by staying open, present, and engaged. Athletics laid the foundation. From nose guard to performer, the discipline of football shaped Casey’s resilience and confidence. Late bloomers bloom beautifully. Casey didn’t land Man vs. Food until he was 40, after years of restaurant work, acting gigs, and creative hustle. Losing his father changed him. The pandemic gave Casey unexpected time to care for his ailing dad—a gift he now carries forward on global travels with his father’s ashes. Behind the scenes of food TV is wild. From eating challenges to custom-created show openers, the grind of production is real—and so is the fun. New show in the works. Casey’s pitching Stage, a Dirty Jobs-style series exploring the unsung heroes of restaurant kitchens, from dishwashers to prep cooks. Featured Quote “I stopped saying no to myself. No, I don’t have enough time. No, I can’t do this. I realized I was the same person bartending and acting. I just had to say yes.” — Casey Webb TRANSCRIPT Casey Webb’s Road Trip, Rebirth Band & Crawfish in the Carolinas Casey Webb (00:02.318) Oh hi. Jeff Dudan (00:03.892) Hey Casey, how are you? Casey Webb (00:05.934) I'm doing great. Oh, do you wanted me to start? Oh, I'm sorry. Was that was I leading this? I'm totally ready. I'm ready to go. Are we ready? Jeff Dudan (00:11.412) Yeah, awesome, awesome, awesome. Well, hey, we're here with Casey Webb. I am Jeff Duden and we are on the home front. Welcome, sir. So excited to be on with you today. Casey Webb (00:21.422) Thank you, Jeff. I appreciate it. And we just so happen to both be in the Carolinas, which I don't live in, but I do visit often. So that was a nice surprise, right? As far as surprises go. Jeff Dudan (00:32.628) Yeah, absolutely. Down in Wilmington, we're in Lake Norman area, north of Charlotte here. So what have you been up to down there this week? Casey Webb (00:40.462) So I took a road trip with my dog, landed in Cape Charles, Virginia, camped out over there on the Chesapeake, which is pretty incredible. And then I came in day before yesterday, it's a buddy's birthday party. He hired the Rebirth Brass Band from New Orleans, Crawfish Boil, at this dive bar called the Greensville Yacht Club, which is formerly the Double Nur, which is right near the Greensville. Ample Theater or theater that's over there. So it was a lot of fun. We had a good time yesterday and it's really cold and dark and rainy in the Northeast and New Jersey where I live and where I'm from. And so it was time to take a little road trip. Last year I traveled a bunch, Thailand, Costa Rica, Ireland, New Orleans for Jazz Fest, which I'm going to next week for fun. And I could, I usually write that stuff off because it's travel and part of business. It's part of doing business. Jeff Dudan (01:15.86) Yeah. Jeff Dudan (01:33.3) That's right. Casey Webb (01:36.494) But this year I was, I hadn't gone anywhere. I was just kind of embracing the winter in New Jersey and I'm sorry I did that. Because January was the longest six months of my life. But hey, I'm here and I got some sun and it's great to be outside. Yeah, I can hear you, can you hear me? Did you lose me? Oh, we're good. Jeff Dudan (01:49.364) I see you froze a little bit there. Are you still good? Can you hear me? Jeff Dudan (01:54.868) Yeah, yep, awesome. Now you're just kind of freezing a little bit here and there, but that's cool. Well, hey Casey, so tell us a little bit about growing up in New Jersey and the things that you did. Casey Webb (01:59.566) Okay. From Football to Theater: The Pivot that Changed Casey’s Life Casey Webb (02:10.638) So I'm originally from New Jersey. Parents are both New Yorkers that made their way in the late 60s to a little town called Little Silver, where the train conductor affectionately called it as small change. And a lot of blue collar in that town, mixed, I guess. Dad commuted to the city. So my mom was a stay -at -home mom, which is pretty great. I got to spend a lot of time with my mom in the kitchen. Yeah. Very humble beginnings, you know, for me, sports was a big part of my life. Later in life, I guess through high school and into college, I played football, I wrestled in high school and played football in high school and college. That led me to play or high school led me to play football in college for a brief stint. And it was I realized then like I did real well. I walked away with no injuries. I had the body for a football player, just not the height. So I went D3, I thought I was going D1. And then, you know, like most things sometimes it's time to put, you know, hang up your helmet and leave it on the field. So I did. And that's actually when I started acting. Or I was always acting out, but I put some energy into actually performance and I started doing theater at 18. But. Jeff Dudan (03:23.38) Ha ha ha ha. Casey Webb (03:30.318) Before that, you know, living in a small town, like, parents know each other and a friend's family had a pizza place. So I started washing dishes at this pizza place. So there's like this parallel world of acting in restaurants that would lead up to why we're here. Talk probably about man versus food. Jeff Dudan (03:41.46) Yeah. Jeff Dudan (03:46.068) Yeah. So what position do you play in football? Casey Webb (03:50.894) I was a defensive tackle. They tried me on both sides and I just wasn't, I was more, I was more, and this is much as such as life, you find out later in life, I was more reactionary, you know, or reactive. So defense is where I excelled and I was about to go in as a freshman. I was like 230, 240 at five, nine, just a big head, big shoulders, big hands. It's my Italian Irish heritage, I think to that and my grandfather. So, uh, I, uh... I... then what? Jeff Dudan (04:22.228) And I'd put you right over the ball, right? That's what I'd have done with you. Yeah. Casey Webb (04:25.102) Yeah, I was nose guard. I was a nose guard. So I later became nose guard. Yeah. And I was, by my senior year, I really got into running, believe it or not, my junior, senior year. And when we go to football, we went to football camp every year at Penn State from Jersey. And it was pretty, really probably still is popular camp for kids. And that really got us ready. These days, kids are playing whatever sport. all year long, which is incredible. We would have been a different team if we played all year long, like most kids are doing with, be it baseball, soccer, basketball, what have you. But I dropped like 30 pounds, like over the course of like junior to senior year. And then going to senior year, they had to change the defense. So I was a D tackle. I became nose guard fast and just popped out of my stance and coach called me pop. Actually, that was my nickname. And he would scream it from across the field. And he was like, Jeff Dudan (05:14.42) So what? Casey Webb (05:17.294) He had a titanium hip and he walked like he had one too and he would scream and it was amazing. He was like the coach you would see a character on a television show or movie and I was like, it was complete and we were the Buccaneers believe it or not, we were the Bucs so go Bucs. Jeff Dudan (05:27.028) Like a pirate. Jeff Dudan (05:32.212) So you had, you were the Buccaneers and your coach had a metal leg basically. Casey Webb (05:36.526) He was a total pirate without the parrot. He was pirate without the parrot. And my buddies to this day, it's like anytime there's anything, because a lot of these guys that I grew up with, now their kids are going to the opposing schools that we definitely were up against, or I still hate actually. And their kids are going to those schools. And anytime I finish off with texts, it's always go bucks, go bucks, go bucks, you know, hashtag go bucks. So I haven't forgotten and I will never forget. Life Lessons from Sports: Visualization, Grit & Growth Jeff Dudan (06:01.076) Yeah. Anything you learned as an athlete that you still take with you to this day into business, entertainment's tough, you're always getting knocked in the mouth, you gotta go do auditions, it's kind of thankless and football man, like you make a mistake, you're out. What, yeah. Casey Webb (06:18.414) Yeah, I'm gonna go jump off a bridge right now. No, that's not. It's every all of it, you know, truthfully, because I had my older brother was just a tough son is still a tough son of a bitch. And he, he kind of paved the way for me, my grandfather was my uncle's my dad. Just a sweetheart of a man wasn't an athlete, but he was really wise. And so like, I had this great. masculine energy from my uncles and my brother specifically because it was home with me and then my grandfather this looming presence of my grandfather and then there's my dad who like He would sit me down and when I was a junior in high school when I started playing a lot more I actually made Varsity as a sophomore you have to play freshman and then unless you're like a really good cat you catch real well so as a defensive player I made Varsity as a sophomore he would sit me down and visualize my day and visualize the game every Saturday. Every Saturday, he would do that. And like, and my dad grew up in the Bronx, poor Irish guy from the Bronx, but he's part of this program that brought him to Massachusetts in the summer. So he had some worldly vision. And he growing up in the 60s and 70s, he found a, you know, as a Catholic, he grew up Catholic, but he had these life philosophies that he, he passed down to me and my brother and he would have, he would have me visualize and, and quite that, that changed the game. for me because I already saw what I was doing and like everything was in slow motion, but I was at full speed and that's how I excelled really. And I've taken that with me wherever I go, especially with, you know, for any sort of performance. Um, you know, I got knocked around a long time, but that's just part of the business. I didn't man versus food for instance, was like what people most know, know me for. I didn't get that till it's 40, you know, and that was 2017. So I had worked as a PA for years, uh, while Jeff Dudan (08:04.852) Right. Yeah. Casey Webb (08:09.934) bartending, working in restaurants, pursuing acting, I was trying to do all these things. And the sports element, that's where it came to a point when I was in college, I was like, I'm done using my noggin to knock people over. I'm good at it. That's great. And I'm not going to be a pro. I'm just a small guy, right? So I hung it up. And that's when I really started pursuing like, you know, because it was always a physical and emotional release. You know, we had some problems as kids, parents got divorced, yada, yada, yada. But I was able to use of sports to kind of relieve that tension, that child of the banks or even just testosterone, you know? And it was, I just jumped into another thing and that was, it was acting theater. Yeah, it started with theater. Jeff Dudan (08:53.204) So when you jumped into that, were you doing scripted productions or improv? What was your first opportunity? First Cold Read, First Failure: How Improv Saved the Dream Casey Webb (09:00.174) So I came back home to New Jersey. I was in Western Pennsylvania playing football, which is a school called Wilkes. It was Wilkes College then. It's Wilkes University. It's near Scranton, near Susquehanna River. And it's only football and beer, basically. Football, beer, and girls, which is great. I just realized that I wanted to do a little bit more, you know? Are you leaving? You're taking the show on the road? Jeff Dudan (09:15.956) Right. Jeff Dudan (09:24.083) Wait a minute. Jeff Dudan (09:28.884) That sounds good. Casey Webb (09:30.446) Yeah, it was great, you know, at the time, but I was just like, I just had to change the heart. And I wrote this really long letter to my father and my brother and told him that I was done. You know, I drafted this letter on legal tender letterhead, whatever, legal pad, and he just wrote, wrote, wrote telling that I was done playing football. And that was when the hardest, probably the first hardest decision I've had to make because, you know, the legacy my brother had and like, I was. He's a bit of a hero of mine, as well as my father. So to tell them that I was quitting something, because my heart just wasn't in it anymore. And I couldn't just do it anymore because of them, for the sake of them. So that was the toughest part. So I got back to Jersey and a really close friend, my three closest friends were pursuing acting in some capacity. One was going to conservatory, American Academy of Dramatic Arts. The other one was getting his undergrad at UVM University, Vermont, but he was minoring in theater. He later went on to go to New School Actor Studio under James Lipton at the New School. And I auditioned with him to get in and he got in. So I got to audition in front of James Lipton, which is a pretty big deal for a theater actor or an actor in general. And I mean, I didn't have my undergrad. So I was studying with the teachers that taught privately, but not at university level at the university. Anyway, there's a lot of ways there. And I just took my way, you know? So my buddy at home was at community college. It was when I, he... Jeff Dudan (10:43.252) Right. Casey Webb (10:52.942) He encouraged me to audition for this play at the community college in the area where I grew up, mom. It's a Brookdale Community College. And it's like the two -year school for Rutgers, Monmouth University, a bunch of other schools, and Seton Hall, you know, all these Jersey schools. It's a two -year school for that. So I auditioned for the first time, cold read. Basically you take a piece of paper. This is actually an audition I have to do later, but, and you read it cold. and you perform it on a stage in front of your peers that are auditioning for maybe the same role and I failed. It was the hardest thing. Jeff Dudan (11:27.22) So how much time do they give you when they hand the piece of paper to you? Do you read it from the paper or do you have to memorize it real quick and then do it? Casey Webb (11:34.702) It's a little bit of both. You got to, you know, like it's, it's, it's part, um, owning some of it. What can you do with this? Exactly. Exactly. It's, it's cold for a reason because it's not hot enough for you to have spent time with it or put any emotion behind it. So it put me in a position where I had to just rely on just instinct and gut. And, and that led to me not getting any roles in that play, but I did step into that, the next class that semester, which is all improv and then that changed my life. Jeff Dudan (11:37.108) Okay. Jeff Dudan (11:40.628) Like here, what can you do with this? Yeah, here, what can you do with this? All right. Casey Webb (12:03.726) as far as I was concerned. Because then that's what I realized, like, that's what this is what I want to do. This is my next challenge. This is what I want to do for the rest of my life. And, and, yeah, I never, yeah. Jeff Dudan (12:14.164) How much of improv is systematized? Because I'm fascinated by the concept of it, and all I watch is comedy, man. That's it. And so if you're in Second City or if you watch the Farley documentary, that kind of stuff, how much training? Is there just systems? Casey Webb (12:23.886) Yeah. Is that why I'm here? Do you find me funny? You froze, Jeff. Where's Jeff? Try to experiment. Sure. Jeff Dudan (12:41.108) and processes that you use that help get you to the next joke, to the next line, to carry it forward. I imagine there is, but like to me, it doesn't, it would be hard to, it would be hard for me to make up like how that process works. I'd be interested to hear you talk about it. Improv Training for Real Life: Listening, Reacting & Hosting on the Fly Casey Webb (13:01.07) It's a lot of play and it's all listening. So it's listening and reacting and upping the ante. And there's a, you know, you'll probably hear it, maybe you've heard it, there's this yes end element. Cause as soon as you say no to something, you cut off all conversation. So like, I've never, you know, leading into Man Vs Food, I never hosted a TV show, a show on TV, but I have hosted live stuff, you know, and with improv. Jeff Dudan (13:12.66) Right? Jeff Dudan (13:16.564) It's over. Casey Webb (13:27.758) experience and not just practice like how to get the Carnegie Hall practice practice practice right so with interviews it was the same thing I use these tools that I learned as a young person who failed on a cold read on a stage how to listen you're actively listening because if you're thinking about the next thing you're going to say while you're performing of course there's a bit of that but like you're you have to be listening to what what's being said to you in order to react to that and take from that mind from that and then use it. and to up the ante or create another story or, you know, or, you know, take us along the road. Like you're both walking this path. You and your other characters could be two, three, four, five of the people that you're improvising within a group. And just to give you an idea, like with Man vs Food, I'm talking to strangers about food. I know what I need to say. I know what I want them to say. I have to lead them there to say it. So we're mining for sound bites to give you an idea of like what I was doing when I was a young person was basically active listening. And I, my opinion, the greatest gift you can give anyone is your full attention. I'm listening to you. I'm hearing what you're saying. I'm not thinking about the next thing I'm going to say. Though I'm excited and I want to add to what you're saying, I need to take a deep breath and actually absorb what you're saying and then let that information wash over me and then proceed and have that dialogue. You know? Um, so it's really, it's really about listening and being open to play and not saying no. It's like, yes, end your life, you know? And it's funny because that happened to me and there was a point in my life where I was like, I hate bartending, but I love acting. I'm living in Brooklyn and I'd just broken up with a girlfriend for many years and I was in a weird place and I was like, wait a second, I'm the same person that's bartending, that's acting. And what it was affecting me in the room, because like we used to, believe it or not, we used to go into a studio or an office space and audition. We don't do that anymore. It's now like this, right? It's all, which I miss. So it was affecting my work because I was like in my head about this hating, I just like this duality in life. something snapped. It's like I'm the same person behind the bar having these conversations with these folks and being entertaining or whatever, trying to entertain as I am the same person that would walk into the room auditioning for this job that might help me pay my rent, you know, or, or advance me in my career or, you know, so it was like this literal switch. And then that would, that's what led me to a great deal of success because I got out of my own way. I was listening to my gut, my heart, truthfully, and, um, I didn't say no. The Power of “Yes, And” in Career and Life Decisions Casey Webb (15:52.174) You know, I stopped saying no to myself. No, I don't have enough time. No, I can't do this. I was like, holy crap, this is affecting all of it. Like not just the work, but my whole life, you know, I was closing myself off by saying no. So with improv, you're just saying, yes, you're advancing the thing. So when I say yes, end your life, it's that's what I'm actually doing that. You know, I, that's what got me down here. You know, I was like, I got to drive, like I could have said no a million times and never drove to drove down to a woman said, but I did because I knew like, The juice would be worth the squeeze. The nine hours in the car would be worth all of it. And it was, of course, I'm like on the Chesapeake cooking steaks with my dog. It was amazing. You know, just cause I said yes, you know, if I said no, I'd be home in the cold wondering what the hell was going on down here. This crawfish boil. So. Jeff Dudan (16:38.42) Yeah, look, everybody needs an adventure in life and the more you can have, the better your life is gonna be. We end up right where we are in life based on the decisions that we make and the talk in our head that we listen to that put walls up around us. And I think just saying yes to, defaulting to yes is a powerful tool to get you where you wanna go. And then I think United is similar and it's obviously smaller, but. Casey Webb (16:42.958) Yes. Amen. Jeff Dudan (17:07.06) you know, with this podcast, I look back at the first ones that I did and I was like, I could tell my body language, I was nervous and I was, I had scripted questions and you know, and, and, and then at the end of the day, I think I was, I just, and then what I, what I realized was if I'm smiling and the guest is smiling and we're having a good time, then like, that's about as good as you can get because people can hear smiles. Casey Webb (17:17.614) Were you like this? Were you like this? Were you like this? I mean, I would be. Jeff Dudan (17:34.068) And if you're having fun and you're going, you know, you might not get to everything you wanted to get to, but who cares? You know, have a good time with it. And, and then, you know, people, people seem to resonate with that. So you, again, you gotta, you can't, can't take yourself too seriously. Get out of your own way. Don't be fearful. And by the way, none of this is fatal. Like you don't get the, you don't get the part. Okay. Yeah. Casey Webb (17:39.502) Okay. Casey Webb (17:55.15) No, no, no. That's part of the job. You know, like I learned very early on, like not to tell anyone that I had any audition for anything because when you do, I was like, yeah, mom, dad, I got auditioned for this TV show. And then like a week later, do you get it? No. And you would say that a lot because there's a lot more times you're saying, no, I didn't get it to the yes, I did get it. So that got cut off very quickly. And you know, with the yes thing, like you say yes to it, you could decide to say no to it. Jeff Dudan (18:15.156) Yeah. Casey Webb (18:21.806) eventually once you've sussed it out, but don't rule it out until you know more about what that thing you're knowing, not N -O -I -N -G. So yeah, like just if you start with yes, you're open, you're opening the thing up. When you start with no, there's no possibility, you just end it. It ends the conversation. So that's how I see it. I'm a very visual person and visual learner. So, like I could, in my mind's eye, and my father kind of lent that to me. He passed this little, um, torch of like, uh, just the visualization torch, let's call it, you know, and that's helped me every day, you know, when I get caught up here, cause it's a motor, right? It's like, it's your gut and your heart is really, you have to listen to that, that little person inside. Some people call it the angels. Some people call it your inner child, whatever that voice be and whatever you call it, really trusting in that, because then you can put it up here and then put it to work, right? Cause it's just a machine, you know, that we get caught up in. the cogs and the wheels of it all sometimes and becoming quiet is the point. And that's what he was doing for me. So my father's a very much he was he did pass a couple years ago, but he meditated, you know, for years that he taught me, you know, he brought me to a place that introduced transcendental meditation and meditation is a big part of that too. That's meditation is also prayer. It you know, it's a lot of things, you know, and for a lot of different people, but becoming still helps, you know, the the uncertain waters, you know, like it helps you navigate through things a lot easier when you're calm, you know, quiet and you're available to receive, you know. Jeff Dudan (20:00.436) I spent four hours last weekend with a business partner and he brought up this, and it's time we hadn't really spent together out of the office. It was on a weekend. We just went and sat around his pool on the lake and might've had a couple of cocktails, but he's in this training. He said, you know, I'm learning to sit in awareness. Casey Webb (20:16.494) Sure. Jeff Dudan (20:23.38) And he described it as, you know, I'm in this situation and something's going not well and I'm tending to get upset about it. But if I just sit in awareness and say, all right, what is this situation? What is the universe trying to tell me with this situation? Where are my opportunities to learn? I can take it as a slight, I can take it as a problem or a mistake, but in reality, if I just sit in awareness and I... I get objective, I get extra -spective, I get outside myself and I look at this objectively. What am I learning here? And I'll tell you what, man, I've found that to be a powerful little three words. Just when I'm, my head's, when everything's spinning, I got everything going on, just sit in awareness for a minute. And I have worked on meditating, but man, it's hard. Yeah. Casey Webb (21:13.23) It's work, you know, it's not easy and it never will be easy. It's just one of those things where you have to make time and carve out time to become still because as soon as you hit the ground in the morning, it's like, you know, things are moving. So it's really the time when you wake up, you know, I have a thing like get up. It doesn't always happen, but when you wake up, get up, you know, make your bed and then start your day. Cause you'll never get into a made bed faster than you would in an unmade bed. You know, if your bed's unmade, you're gonna crawl back into bed. If your bed is made, and then, you know, my dog is often in there, so I'm like, get out so I can make the bed so we can start the day, you know? But yeah, when you're in stillness, when you're quiet, and you're in that awareness that you speak of, you're able to receive things. You're able to see things without judgment. Just like walking meditations is very similar to this, is you're just taking a walk. You're not judging anything. You're not calling out. You're not speaking. You're just receiving the color, the light. You're just letting it wash over you. And... the things that come up when that happens, it's like, it's just clearer. Things are just clearer. You're seeing more by not judging or like having them, you know, like thinking about all your problems in that moment when you're actively listening and being still and quiet. All this stuff washes over you, just especially in nature. I mean, I lived near Prospect Park in Brooklyn in New York City. And to me, everything outside of your small apartment, in my case, is your backyard is and that was all the New York City. So I was able to retreat there often because I grew up in the suburbs. We camped my whole life as kids. I thought I was going to go outdoor mountain rescue, fire jumper, all these crazy things before I was led my way to acting. But I've I've I've always sought out nature because I know it's just I mean, it's it's it's there for us. You know, it's like especially living in a city for most of my adult life. It's one of those things where it's telling you to become quiet and listen. You know, so you can have your wits about you if there's, you know, wild animals or like impending branches or what have you, you know, it's like, it's a, when you realize how lucky we are, you know, it's a, or when you realize how lucky you are, there's so much to get, you know, with very little giving. It's just like this, all these beautiful things, you know, in nature that gives us. Caring for Dad During COVID: Cooking, Connection, and Closure Jeff Dudan (23:31.828) Yeah. Hey, I'm sorry to hear about your dad. It sounds like he made a big impact in your life. Casey Webb (23:35.022) Oh, thanks. Yeah, thank you for saying so. You know, I was lucky enough, as the story goes, we finished filming in Florida in the Keys, in Key West. This is like BC before COVID, right? And right after we were finished filming, coincidentally, South Beach Wine and Food Festival was going off and I wasn't working it, but it's a very, it's all the pros from Food Network are doing demos and it's a really great event. and it's right on the beach in South Beach. And I went just to go see some people that I knew, people in the industry and just decompress and quite honestly digest. Cause I think I had to eat like a giant key lime pie or something the day before. And I got back to New Jersey and we just moved my daddy sold his place. He moved into this winter rental and he was looking to buy or maybe rent. I get sick. Like, and that was like ground zero for apparently for me for COVID. I got that then, you know, I got sick, let's say. And well, in the short, I get better. I have a trip planned to Costa Rica and I go to Costa Rica, was it March 16th and March 20th, the whole world shuts down. So I find myself in Costa Rica. I want to stay for three months because there was nothing going on in New York city. It was just like, friends are like, stay, cause it's hell here. My brother was taking care of my parents. Everyone was cool. So I stayed there. The network and the production company were figured out. I got a 10 episode gig called Best Places to Pig Out and I had my microphone and my stuff there too, because I had to do some episodes of Man Vs. Who, do the voiceover, because we do voiceover for the show. So I was like, oh my God, I'm in freaking paradise, you know? And then this is a long story long about my dad. But after three months, it was like, I was there with friends and it was time to go. And it's like when paradise can become purgatory, because I started listening. Casey Webb (25:34.222) my mind was just over. I had to get back to work. I had to do something because I just, I was almost felt guilty. Went back home and, um, we moved my dad into this beautiful building and, uh, he just aged a lot. And I was like, I, I gotta make a move here. So I was literally blowing up an air mattress in his place and putting it back, you know, before he woke up cooking. And so if we didn't have that time off, um, cause we would went right back into production and I'm, gone, you know, it's like 10 days on 10 days off and more or less and when we're in production. So I had to spend like over a year with my dad before he got sick. And then he passed never had COVID but he got he wanted a little bit of cancer, a lot of treatment. And he's just an old Irish guy who's been bet that that it's a tough thing to go through that part of it because it's you want it to work but it doesn't seem to ever work, you know, for those of you who are older folks to just their immune system is. Jeff Dudan (26:11.7) That's great. Casey Webb (26:31.438) is not as strong, but I had to spend the beauty of that. I wouldn't have not, I wouldn't have had that time to spend with him if the world didn't shut down quite honestly. So some people have had terrible experiences and some others not. And mine was pretty incredible. We fought like brothers, you know, cause we just did. But I got to cook for him every day, multiple meals. And, and, um, that was, that's, that was really special. And then since then, um, he, he wanted to be cremated and, uh, awesome. He had taken care of all of it, you know, and, and he was a volunteer fireman for many years in our town and like, like whatever fun they paid into took care of all of it. Like everything was taken care of. Like my brother and I didn't have to do anything. And it was like, wow, this is cause that gives a very stressful time talking to friends that had similar experiences with their parents. And so he, I have these ashes and my brother's like, all right, what do you, you take them? I'm like, he's not very sentimental, you know? And I was like, all right, so I'm going to take them with me. I took them to Thailand, I took them to Costa Rica, I took them to New Orleans. I took... Jeff Dudan (27:32.436) Awesome. How many times did he get tested at the airport? Casey Webb (27:39.022) Uh, no, it's funny because I had them. I didn't have the whole bag. I took enough for Thailand. It took enough for Costa Rica. I took enough for, you know, jazz Fest in New Orleans. I took them to, I took them to Ireland. Um, Jeff Dudan (27:45.172) That's right. Yeah. There's not little bits of him in blue vials across the airports of the world. Casey Webb (27:55.15) nose and like a plastic bag rolled up and I just put it in my carry on. I fly a lot. So truthfully, they're looking for, you know, they're looking for, you know, uh, bombs and, and lots of heroin, I guess. I don't know, you know, right. They see they're like, Hey, you're the guy. No, I hope not. I, you know, maybe, uh, yeah, I mean that that's funny. Cause I meet a lot of, you know, TSA folks who are just great. There's they're, um, Jeff Dudan (27:59.86) Yeah. Jeff Dudan (28:06.58) Look, they know who we are now. They know who you are. You're not on a list. Casey Webb (28:22.51) you know, they're like doing their job and all of a sudden like, Oh, wait, you're the guy. Yeah, you know, some of my greatest conversations were in airports because it's like, Oh, well, because you're all stuck in the same place. And, and to me, you know, I found success later in life or success found me however you look at it. And people stopped me in airport and then like, we're talking and they're like, they're like, look at their watch like, we got to go. Oh, all right. Like they leave me before I leave them usually, you know, I'm like, All right, I guess you got to go, you know. It's just funny to me because Jeff Dudan (28:25.844) Yeah. Casey Webb (28:52.174) They are ones say hi to me, but I'm the one who doesn't want to believe, you know, uh, cause oftentimes I'm like in my head and I don't want to necessarily be there thinking about all the things I gotta do, what I didn't do. I could have done this better. And then it's like, Oh wait, like you're, you're, you're like these little, you know, people that I don't call them angels or whatever they are. You know, they're just people that come into your life. And it's like, I want to make time for them, you know, cause kids watch the show, couples watch the show, older folks, what just like families and people. There all kinds of me watch the show. So I have all the time in the world if you have time for me, you know. Jeff Dudan (29:27.06) That is much appreciated, I'm sure. Yeah, I lost my dad in the beginning of COVID, so I couldn't go see him because it was right when everything shut down and he was in bad health. And my older brother did get there and kind of get in right there at the end. But the year before he passed, I had sold the business in 2019. So the year before he passed, I made it a point four times to fly to Chicago. Casey Webb (29:36.462) Yeah. Casey Webb (29:42.126) Yeah. Jeff Dudan (29:53.268) take him out of town for three days. He'd never had a massage in his life, so we went up to Lake Geneva and got him a haircut, got him a massage, went to the restaurant, and just sat there and talked for two or three days. Sometimes my brothers would show up or whoever, but I am so thankful I did that. Because I had moved away and we hadn't been together very much for the previous 10 years. Casey Webb (29:59.694) It's amazing! Yeah. Jeff Dudan (30:21.108) I was just like, man, this is it's now or never and took the time to do it. And then sure enough, you know, COVID came the next year and that was, that was the end of it. And he didn't die from COVID, but you know, it certainly made it more difficult to handle everything. Cause it was like right in the beginning of it and everybody was really freaking out. And then, uh, Yeah, so he was cremated too, but my favorite joke, my dad was hilarious. Like he would appreciate, I wouldn't tell this joke if he didn't appreciate it, but he was just so funny and he was so nice and so kind and so funny, little soft, you know, kind of like maybe you said about your dad, like he could have probably stood up for himself a little more, but so like I'll serve my kids friends like this crispy chicken we get from the fresh market and it's great. And it's got this really thick breading on it. I'll be like. Casey Webb (30:49.87) Yeah. Casey Webb (30:55.918) Yeah, same. Grief and Growth: Jeff & Casey Reflect on Losing Their Dads Jeff Dudan (31:10.516) Yeah, you guys like oh, this is great. I'm like, well, it's my dad's recipe But enjoy it because the urns almost empty But I don't know that's just that he would have appreciated that would have been his type of joke but and then I took I We live in the urn and then I took his ashes up to Canada where he used to take me fishing as a boy and I Casey Webb (31:18.382) Oh my god! Casey Webb (31:30.254) Well, we live and earn, don't we? We live and earn. Jeff Dudan (31:40.276) spread them a lot, spread them a little bit in the lake. So yeah, I mean, it's, I miss them. You know, it's funny that connection we have with our father, as young boys, it's pretty cool. Casey Webb (31:43.374) Amazing. Yeah. Casey Webb (31:53.07) Can I share something with you? I had a friend, I didn't see it yesterday, but I'm on this text feed with all my buddies where I say, you know, hashtag go bucks. And we lost another dad recently and yesterday actually, and big golfer Irish guy, you know, just, just a total character. But like, I wrote this, I like woke up and I was reading what friends are writing. And I was like, you know, we had a long day yesterday, crawfish boy out in the sun, you know, this band played, it was quite incredible. And, um, We were definitely in our cups as they say, right? And I was sitting there, I was just kind of like tearing up reading what my friends are writing. Cause we're all at this age, like I don't have kids, you know, I didn't, I didn't, I didn't get married. I haven't been married yet. You know, just parents divorced. I chose work and yada, yada, yada. But I, you know, I have friends that have kids, I have a lot of friends that have kids. I don't, I don't have any, but I have a small dog I treat like my kid. He's in the, he's in the corner over there, but um, If I could share this with you, just like, I don't know where it came from. And sometimes this stuff just kind of appears. It just kind of channels through you. I very much believe that things channel through you from somewhere, what be it, you know, wherever. But a friend of mine had written something about heroes and legends and like there are heroes, heroes die, but legends, you know, are here forever. And our friend's dad, Jim, Jim, big Jim O 'Brien. Jeff Dudan (32:49.908) Yeah. Casey Webb (33:13.198) He was one of those guys. Like all our fathers were in their own right. But I write in my mind as I'm reading, I see our fathers, brothers, mentors that have passed as statues on pillars in some hall of remembrance. This way I can visit them. Casey Webb (33:38.734) This way I can visit them when I need to. It really makes me proud to know you guys and the mighty men that raised us all to live in power until it's time to rest in peace. Love you boys. Jeff Dudan (33:51.092) Beautiful. That's awesome. Casey Webb (33:56.462) Yeah, I miss him too. I have conversations with him, like my funny little dog, he's the quirkiest little thing. He reminds me of my Dex, my dad loved him so much, that sort of thing. And when he was sick, I was working out through my workouts and some of those, that stuff helps tremendously. Jeff Dudan (33:59.38) Yeah, yeah. Casey Webb (34:21.614) I do a lot of like CrossFit style stuff, high impact yoga. Like I just, you know, I'm in the water as much as I can and in the right season. But it was always like when he was sick, it was like, do it for dad, do it for dad, do it for dad. So it's like, it got me out of my head and then back into my body. And it was like, it's cause some people, you know, they kiss it up to God, you know, athletes, they do it to God or whatever. It looks as a peers or they're giving God the credit, you know? And I think there's something about that in performance. especially physical performance where you're able to kind of detach and it's bigger than all of us. And that's kind of my relationship with the visualization part, sitting down and getting my mind right and bringing myself to that place. So I'm prepared to be present and be in the moment and do my job, because like, especially in performance or acting, they just want you to show up and do your best. And I learned that by the process of not getting the job. by not getting, I got so much more because I was able to correct and tweak and make changes to, so I would get the job, you know? And just a quick crazy story. I used to have a beard and it was graying, you know? And I was like, and some auditions, cause I have a younger look, so I would, no, not at all. I'm embracing it. I mean, look at this thing. It's like a neck beard. Jeff Dudan (35:43.7) Not that there's anything wrong with that. It happens. It happens to the best of us. Casey Webb (35:50.254) Um, totally. It's part of the process, but I still have a full head of red hair, right? So I was, I was like for auditions, I was starting to color it. I was like, Jesus, I'm done doing this. Like I don't want to, I don't, it's, you know, I started doing that. I was like, I want to be as transparent as possible. So I shaved the beard for this cop show was Brooklyn nine nine nine, whatever that great funny show. I didn't get that job, but I shaved the beard off and I was like, Oh, I got this new look. I look like my dad, but 30 years younger mustache, fiery red hair. Jeff Dudan (35:54.484) Yeah. Casey Webb (36:19.662) And I tell you the truth, I got every job after that. And it was six jobs in a row. And like a few of them were commercials. One of them was in Panama, the country. And then the last one was Man vs Food. Well, I actually got Man vs Food before I got the Panama commercial, which was that's a whole other story. Like, I lost my passport while I was there. I was supposed to fly out that day. I had to go to get do a police report to get go to the consulate to get a new one. And then I had a I was flying out on Monday, it's Good Friday on Friday, and like the whole country shuts down on Good Friday. So like I had to do this in a day. I didn't have any money in my bank account, my buddy, they paid us in cash. And I had Jeff Dudan (37:01.492) Was this for the audition or for the show? For Man vs Food? Casey Webb (37:04.558) So I already got the show. But this is this commercial that I did in Panama. And I'm in Panama, it was this German real estate company. It's a pretty funny commercial because it's like, don't be like these guys. It's like Wolf of Wall Street, we replicated Wolf of Wall Street in a two minute commercial, cheaper to film it in Panama, it looks like Miami. I drove a Lamborghini had a Cartier watch wearing suits, we destroyed this like this office space was hundreds of extras where it was crackers, helicopter, it was Jeff Dudan (37:07.284) Okay. Right. Casey Webb (37:33.934) bananas and it's such a beautiful country. Yeah, like they I imagine they dubbed it in German and English but it was like it's like we were speaking English in the commercial and it's German real estate company it's like at the end like the doors kick in we're having this crazy party champagne everywhere there's like clothes are off it was like literally 100 extras and we're just going nuts everyone's soaking wet they're shooting hundred -dollar bills out of this cannon and confetti gold confetti and then it's like Jeff Dudan (37:36.916) And it was in English, it was an English speaking commercial. From Panama to Milwaukee: Behind the Scenes of Man vs. Food Casey Webb (38:03.918) record scratch is like, as if the cops are coming in, like the feds are coming in to end it all. And then it's like cuts to like a white screen. It's like, it's like, well, invest. It's like, basically, don't be an American, you know, it's like, well, invest, we kind of sold out a little bit. But it was hilarious, you know, like, I'm gonna pull smoking a cigar with this, like, amazing looking woman next to me that I can never get, you know, it's like, and like, on the top of this rooftop, you know, it was just, but like, I got caught there, I was almost not gonna leave the country, I had a date with my before like a first date with a girl that I want, I'm dating for a long time. That's Saturday, you know, so, and then Monday I was flying out to Milwaukee to shoot the first installment of Man Vs Food and like, so like my life was so incredible and so like it could have ended, you know, I could have like, you know, if I didn't make it back, I was screwed basically. And so the only ticket left was like, I paid cash for it, I remember, cause they paid us in cash, like just a wad of money to do this commercial and um. Jeff Dudan (38:52.884) Right. Casey Webb (39:01.998) I flew first class and I laid down the whole way and I ate ice cream and they'll never fly first class if you if you're never gonna if you're not always gonna fly first class never fly first class because once you go first class you can't go back it's tough especially when you're a bigger guy I'm like sitting next to other big guys and like coach and like get out of here you know anyway it's obnoxious but that's how I feel Jeff Dudan (39:05.972) Yeah. Jeff Dudan (39:17.524) Yeah. Casey Webb (39:28.174) Oh, but yeah, I made it home, thank God. And like, I got to go to Milwaukee to do this first episode. And we were filming the intro to the show too. So we went to, we were in Chicago and like we shot there too. And it was, it was crazy. Cause we filmed, we had to film the opener of the show and we had to create like challenges. So we went to places that I didn't necessarily eat a challenge, but we created challenges in that first season to, you know, we just didn't have. Jeff Dudan (39:53.076) right. Casey Webb (39:56.046) There was not enough time for me to eat all that food, but we made the time to create the opener, which is really, you know, heart -hitting. And so. Jeff Dudan (40:03.668) Okay, so are you saying that there wasn't always a challenge that kind of was interesting to you guys, so you had to create them at restaurants or just for the opener? Casey Webb (40:10.19) No, oh, well, for the opener, just to get the visual of like these giant steaks and things to give, you know, like we created that, you know, cause the show was off the air for five years. So it ended in 2012, the show didn't come back to 2017. Charles Nordlander, who was executive at the time at Food Network was the one who basically resuscitated and said, it's time, you know, it's time to either bring Adam back or Adam Richman. Jeff Dudan (40:17.204) Oh yeah, yeah, yeah. Yeah. Casey Webb (40:39.214) or get a new host. And yeah, so they went up, I guess he didn't have any interest. And then so they cast for it. So you mentioned Andrew Zimmern, who was recently on the show. I met him, how I met him, I met him, well, I met him in first class. He had no idea who I was on our way to Minneapolis for, well, for him, I guess it was for the Super Bowl, because he was having this huge party. And we filmed, yeah, he lives there now, yeah. Jeff Dudan (40:56.084) Yeah. Jeff Dudan (41:04.18) Yeah, he lived there. Yeah, he lives there. Yeah. Casey Webb (41:08.43) He we were doing two episodes. We did Minneapolis, St. Paul. We did Minneapolis on the same week during Superbowl. It was bananas. I did like a ton of press. Yeah. Yeah. Yeah. Um, totally. And we met on the plane and introduced myself and he's like, Oh, you got to come to this party. Cause his executive Charles Nordlander was my executive. And then I was like, Hey, uh, do members who said, Oh, you got to come to the party. This is a funny story. So I go to the party and I was doing press all day. Cause we had that day off. It was in between. Jeff Dudan (41:14.452) Okay. And were you flying out of New York? Flying out of New York? Okay. Yeah. So he spends, he's a lot, he's in New York a lot. Yeah. Casey Webb (41:38.286) doing the two episodes of Man Vs Food. Shooting an episode of Man Vs Food is three days of filming. So each restaurant gets a day and we do three restaurants. The third day is the challenge day and at the end of that hour, the last hour of that shooting is the challenge. Whatever it be, hot or huge. So anyway, I had, we're shooting. Jeff Dudan (41:54.516) on the third day or on every day. Casey Webb (41:57.262) On the third day, there's a challenge. So it's three restaurants each episode. One restaurant is a challenge and that's at the third day. And when that hour is over, when we're done, the cameras go down, lights go down and then like the guys are in the car, like ready to go. Like it's like, we're out, you know? And it's like, yeah, I'm dragging my leg to get into the car to go sleep on a hot rock somewhere, like a giant iguana to just digest, you know? And so I go to this party with Charles and like we did a bunch of press, we did. Jeff Dudan (41:59.252) Okay, right. Jeff Dudan (42:12.052) And you're heading to the emergency room. Exactly. Casey Webb (42:26.734) Um, one of the, uh, Dan Patrick show I got to do out there, which was hilarious. I got to, I wrestled one of his guy. Yeah, it was good. He's great. I, I'm a huge fan of his and, uh, they brought me on the show like several times, which is once I think we start doing some more episodes, I'll probably be back on there to see those guys. Maybe wrestle Paulie again. Uh, did you see the takedown? Did you see that part? Did you see me wrestle Paulie? It was in the Minneapolis. Oh yeah. Look it up. It's pretty great. Um, Jeff Dudan (42:31.124) I saw that one. That was a good interview. Yeah, it was a real good. Jeff Dudan (42:49.876) No, I didn't see it. Alright. Casey Webb (42:53.774) Well, Dan was like, Oh, so you wrestled in high school is like, yeah. And he's like, are you gonna wrestle Paulie? I was like, you want me to wrestle Paulie? Like my brother long time ago is like, you don't you don't you don't slap box either because he boxed he boxed and kickbox and he's like, you don't do you just don't do that. Either you fight or you don't fight. Okay. And so Dan was like a coach to me, you know, like I treated in that moment, he was my coach and I was like, you want me to I was like, okay, and so I just picked him up and I slammed Paulie to the ground and in a Hawaiian shirt and I could feel the breath leave his body. I thought I killed him. I swear to God, I thought I killed him. But I mean, I'm like 250 pounds of just dead weight, bones, and mass on top of this guy. And he was like, he wanted to do it. He was like, all right, let's go. And so we did it. It's worth looking it up. So I'll send it to you. So we go to this party, me and Charles Nordlander. And it's Andrew Zimmern's party. He was opening up his... Jeff Dudan (43:24.788) It's just... Jeff Dudan (43:41.716) All right. Casey Webb (43:50.19) restaurant, it was before he opened the restaurant, like Sweet Cricket, I forget it was Asian Fusion style restaurant that he was opening up. So the place is packed and I'm looking around like, oh my God, like all these people are from William Morris Endeavor. 75 % of all people in food, hosts, chefs, what have you, a lot of them are with William Morris Endeavor. I'm not with William Morris Endeavor, I'm with CAA. So I look around and I'm like, holy crap. I had to say no to that group of people because I, I'll tell you the story. So I'm on the road filming Man Vs Food and I'm with one agency and my dad's like, yeah, there's a voicemail, a radio show, keeps calling and leaving a voicemail at his house, my childhood home number, which is now debunked or defunct 842 -8487. I had it since I was a kid. And, um, And I go and I go to his house, I get off the road, I go to his house, I hit the answer machine. And it's like, Hey, this is Johnny Johnny from WME, which is William Morris Endeavor. So William Morris Endeavor was calling my dad's house looking for me to set an appointment for me to go talk to them in their offices and see if I wanted them to be my agency. I was like, Dad, you realize? I was like, I forget it. Like the second biggest one of two of the biggest eight at the time agencies, you know, it's like, holy crap. And CAA came knocking at the same time. So, I'm at this party with Charles Norwood Lander. I see Andrew's name. I go say hello to him and like thank him. And then I'm looking around the room, like all these people are from William Morrison Devere or they're, they're represented by. And I also see, well, I still have never met to this day. I see Adam Richmond who was in the wings and yeah, we still haven't met. So, it was just, I was just like, wow, I'm in the lions then right now. Like seriously, I was like, I'm really uncomfortable. Jeff Dudan (45:34.644) Yeah. Casey Webb (45:38.606) But then I just put on a face, like, oh, hey, how's it going? Oh, yeah, CIA's great. It's not fatal. And I did, and I did. I was arm in arm with my executive. This guy, he travels with Andrew, right? He's traveling with me. I had to put my defenses up a little bit, but it was fun. It was an incredible week of, I love that town. If you've ever spent time there, I'm sure you're being from Chicago. You've been to Minneapolis, St. Paul? Yeah. Jeff Dudan (45:38.708) See what? Jeff Dudan (45:43.444) It's not fatal. Walk in there like you own it. Not fatal. Yeah. Jeff Dudan (46:04.212) Yeah, yeah, 100%. It's great. Casey Webb (46:06.862) And I got to see the Super Bowl. Last minute, I got a ticket. I don't know how it happened. Someone said it was in the works and I got to see the game too. So that was probably the greatest filming in its entirety. It was just an incredible week. I haven't been to a Super Bowl since, but just because of timing. I would love to go back and do that again. But it was the first time I rooted for Philly ever, because I'm from New Jersey. We're Giants fans. So it was like, yeah. Anyway. Where were we? Jeff Dudan (46:38.772) Man, we were getting, just getting into the, we're 46 minutes in and Man vs. Food comes up. So it's, well, yeah, 100%, 100%. So, but I, you've been on Bobby Flay also. Casey Webb (46:43.502) Oh, yes. Well, you know, it's I've done other things, you know. Casey Webb (46:59.31) Yeah, I did, you know, like in the, in the, in the mix of things in the first through several seasons, they throw you into the mix because it's now Warner Discovery owns everything. Um, you know, food network, cooking channel. I was a guest host. I was a guest host. So they bring in three judges and then they bring in two guests hosts. Jeff Dudan (47:08.244) Yeah. Were you a judge on there? Were you a... Okay. Okay, yeah, you were one of the two guest hosts. I love Man vs. Food. I watched a gazillion episodes. I love Bobby Flay, Andrew Zimmer. And I've gotten into Robert Irvine a little bit. Yeah. Hey, do you know Mark Tarbell? Out of Arizona? No, okay. Casey Webb (47:22.35) Yeah. Casey Webb (47:26.51) Oh good. Yeah, Bobby's great. Casey Webb (47:32.462) He's intense. He's like a circus. He's intense. Not personally, no. Jeff Dudan (47:41.14) just met him in Arizona just a few weeks ago. Casey Webb (47:43.598) Well, we, wait, did I, wait, did we film with Mark? Did I? Jeff Dudan (47:48.82) Yeah, he said he's been out of it a little bit because he's got a couple of kids he's raising, but he's getting ready to get back into it. But yeah, and so I'm interested to know your, do you have a culinary background? I know you've worked in restaurants, but do you have a chef background at all? Casey Webb (47:55.854) Um, yeah, I've met Mark. I don't know Mark personally. Yeah. Casey Webb (48:07.598) So very much like my acting pursuits, I started washing dishes at 14 because you could then or no one really said anything in a small town. Child labor laws didn't exist in the small town of New Jersey. And that led me like being a dishwasher in any place, you really see the nuts and bolts of things. And because if you slow down, if you get backed up, you're screwed. Everything slows down. And like I would marvel at the like because there were it. Jeff Dudan (48:15.156) Yeah. Jeff Dudan (48:29.876) Right. Casey Webb (48:34.862) I'm surprised there isn't a series that's about the pizza delivery and pizza place because it's just hilarious. The characters that drove, you know, that delivered pizza, the sub guys versus the pizza guys, you know, they're all different characters. And like the pizza guy, like, you know, he was he's probably a convict and that's okay, you know, like, but he had it rolled up sleeve with cigarettes in it. It reminded me of Uncle Headband, like Fu Manchu mustache and like, you know, he was tight tattoos like I I love this guy, you know, this guy's bad ass, you know, he's like, he's just embodied toughness and he's like, just making pizza flawlessly. And I was like enamored by the people in it. And like, I learned then like, anytime you work in any restaurant scenario, there's always gonna be food, right? Like you're never gonna go hungry, you know, and you always have a little bit of money in your pocket. And so that was my entrance into culinary. And then I was, I had a bit of a, I guess, behavioral problem in grammar school. So I went up to this. Jeff Dudan (49:19.316) Right. Casey Webb (49:32.046) other school for a couple years. I think I even mentioned I was acting out before I started acting. And at that school, there was it was a lot of vocational stuff. And you kind of it was a point system. So it was like, if you focus your energy, and this is kind of where my dad stepped in, and my parents split up at the time, and, and the visualization, the focusing thing, and like, I was able to narrow my focus. And like, they were like, you know, we had to see a therapist and like, he has ADD, my dad's like, okay. Jeff Dudan (49:32.532) I can't, I find that very hard to believe. Casey Webb (50:01.326) You're not putting my kid on drugs. And so like, uh, never was medicated for any of that stuff. And it's okay if you are just, he just decided not to do that. I'm thankful that he didn't. He gave me other tools to work on. And, um, so it did vocational culinary basic, basic stuff, like not how to, how not to burn your house down, how not to cut your hand off, you know, that kind of stuff. And, and that progressed. So I had vocational culinary there and that led me into kitchens actually working in kitchens and like Bourdain's great at this. He's like, don't go to culinary school. He's like, go out and work. do that because once you're, I was just listening four hours of driving on the second half of my, my route to, um, medium raw, which is a really great read and or listen. Um, and he talks about that. He's like, you're going to be $40 ,000, even though he went to CIA and a lot of my friends with the CIA colonial Institute of America, which is like the best, you know, next to French culinary, which is now, um, uh, yeah. So I, I went, I worked in kitchens and, um, I got opportunities to move up within kitchens and. Jeff Dudan (50:41.876) Yeah. Casey Webb (51:00.718) And then like I was moving into New York city to pursue acting. And I realized like, you're, there's more money in the front of the house. And that was a bit of a character. So I went to the front of the house, started bartending. Well, I started, I would bus boy, food runner, expediter. And then you, you eventually work your way up to bartending. Like that's, you, we wait tables before you bartend typically they're not going to story behind the bar. So I worked every area and then even to management I've never owned. Um, Jeff Dudan (51:11.444) Yeah. Casey Webb (51:30.03) So I didn't go to conventional culinary school. I just, I learned in kitchens and got opportunities to do so. And, um, yeah, so I'm not a chef, a chef leads kitchens. I mean, people call me that, but it's like, I'm not a chef, but, um, well, you asked me if there's anything I wanted to talk about. There's a show that we're actually pitching, which is called Stage, which is essentially, I like to affectionately, um, describe it as dirty jobs with microbeets food. And it's working your way through each of these roles in the restaurant business that shine a light on how. Jeff Dudan (51:34.484) Got it. Jeff Dudan (51:54.356) Okay. Casey Webb (51:59.918) difficult, you know, and how necessary these roles are and be it the dishwasher at the burner den to the hot dog person at Yankee Stadium, you know, who's like that's you have to start you have to and staging is essentially a free internship that you would go work in a kitchen for nothing and learn skills from that chef and then maybe get hired. And so I for me, it's like I didn't have an opportunity to go current go to culinary school nor did I have an opportunity. to, it was a financial thing to go to a conservatory for acting. I paid my way to train and do my thing, whether it be improv, sketch, stand up, I just went and did it, you know? And... Jeff Dudan (52:39.092) Look, man, that's a brilliant idea for a show. I can see it. Like, I can see, like, because, so when I was 12 and 13 years old, there's a lot of similarities in our lives. I was acting out as well. And so when I was 12 and 13 years old, I was working Friday and Saturday nights, four till 1 a .m. in a Mexican restaurant in Chicago. And I started, you'd go in there and, yeah, and they would, so we'd spend the first hour. Casey Webb (52:42.062) Thanks. Casey Webb (52:52.046) No. Casey Webb (53:02.317) Por que no? Why not? You know? Jeff Dudan (53:08.244) and we would be folding napkins into triangles and doing setups and things like that. And then they would bring out plates of enchiladas and the entire staff would eat together. And then, and then it would open up around five o 'clock and you know, it would just be, you'd just be crushing till 11 or 12 o 'clock at night. So I started as a bus boy. Then I moved into the kitchen and I did appetizers. So I was like, I don't know what it, what the position would have been, but like I would do the appetizers and stuff like that and move. Casey Webb (53:16.782) Amazing. Jeff Dudan (53:37.108) plate, whatever they told me to do back there. And then I also ended up behind a bar wearing a little black vest at 13 years old lighting people's cigarettes. So I don't know what that says. But there's a there's a lot of stuff. There's a there's a lot of stuff that happens in the back of the house that is I mean, if you think if you think kitchen confidential is bad, I mean, you know, get outside the chef stuff right into all the other support people. I mean, Casey Webb (53:45.838) Yeah, Chicago, right? Casey Webb (53:54.926) Oh yeah. Casey Webb (54:02.414) Sure. Jeff Dudan (54:04.308) you know, it's gonna be it's gonna be interesting how far you go with that because, you know, sometimes if people see what happens in the kitchen, they might not eat there. Casey Webb (54:14.222) Right. And then, you know, a lot of people haven't read Kitchen Confidential and, you know, I recommend you do, you know, because it's not only is a great read, it gives you a bird's eye view. It gives you, no, it gives you a fly in the wall. Hopefully not. Because there are flies on those walls. An intro to, you know, to kitchens and how things are run from Anthony's perspective, which is I read that it was like, oh, OK, like, you know, anyone that has worked in restaurant business can relate to some degree. And he's just. He's just a, he was and is to me just a kind of a superhero in the industry. And yeah, it was like, it was like a Bible, you know, at one point I was like, okay, you know, we're not alone, you know. Jeff Dudan (54:55.156) Yeah. Did he narrate medium raw himself? Was it his voice? All right. Look, I can't get enough. I still to this day cannot get enough of that guy. Casey Webb (55:00.814) Yeah, yeah, yeah, yeah. Yeah. Yeah. No, and he's relentless, but he's honest about it. I feel like, and about himself too, and he really opens up. They're like vignettes, each chapter is like a deep dive into something specific. I'm looking forward to the other half of it on my way home. I waited, I stopped listening to, I'm like a total true crime degenerate. All I do is listen to true crime stuff for whatever reason. I'm just really fascinated by human behavior, whether it be, this way I can see it coming. Jeff Dudan (55:11.06) Yeah. Casey Webb (55:35.726) You know, it's like, oh, that guy's, you know, you should watch over that person. But yeah, it's worth a read or and or listen. It's in to hear him speak it. It's like it resonates that much more instead of me thinking of his voice in my head when I read it. It's just nice to hear his voice, you know. And yeah, culinary, I, you know, yeah, he's told Poe and like he talks about his relationship with Food Network and he's basically they let everybody go, you know, Emeril and him and they're like a new regime came in and. Jeff Dudan (55:54.036) He was a poet. Casey Webb (56:04.334) That was the best thing that could ever happen to him because then he became the journalist. I think that he was always meant to be because of that, because he went to other platforms, you know? And so, which is, and it's funny because we were with, he was on travel channel first, as I remember. And so were we with Man Vs Food the first two seasons. And we, it was like the wild west. I could say anything, which was amazing. A lot of that stuff. I grew up watching Warner Brothers cartoons. Funny enough, Warner Brothers now owns, it's Warner and Discovery. And just, you know, the subtleties of things, you know, the innuendo and like letting, you know, letting things, people say the craziest things and like, and working off of that. I love my job for many reasons. You know, I don't like the eating part, at least the humongous and the hot stuff, but everything else is pretty amazing. So it's, yeah, anyway, it's a good read. What was I gonna say? Oh. Jeff Dudan (56:58.228) Well, I'll tell you what, yes sir. Casey Webb (56:59.854) The real real quick, the the the stage thing, it's not picked up yet. So we're still pitching it. So if you know anybody or a network that really wants to see me very much like Casey and Man vs. Food, Lumix is way through every position in the restaurant business, you know, over and over again. And with with hopefully with as much humor as Mike Rowe does on Dirty Jobs, because I really see it like that. And I love Mike Rowe for what he does. He's just brilliant at that. And Jeff Dudan (57:07.028) Okay. Jeff Dudan (57:26.548) Yeah. Casey Webb (57:28.526) showcasing what people do as far as hard work or the dirty jobs that people don't want to think about or do. It's like there was this other show that we had this idea for and it was American Trade, which is very much of the same thing. It's the things that are still made in this country and like just made here, you know, by people that live here, no matter where they're from, you know, like, you know, we're all immigrants at one point, you know, so it's a, it was just a beautiful foray into that world. But anyway, Staj, yeah, if you know anybody, let me know. Jeff Dudan (57:45.108) Right. Jeff Dudan (57:57.556) So is your vision to have the truth cam and the cameras behind the camera? Because the brilliant thing about Dirty Jobs was the fact that they had somebody that was always rolling. And if he wanted to do the camera take, he could always, they were filming it, but then he always had the camera he could turn to and just say the most ridiculous thing. And it was like. Casey Webb (57:57.998) You Casey Webb (58:08.494) Oh yeah! Casey Webb (58:14.222) Sure. Casey Webb (58:18.542) Yeah, I really, I feel like there's things missed. Some of the things I've said in situations on Man Vs Food are ridiculous and just because of the person I'm talking to, not just because of me. Like I said, things channel through us. It's in the moment and it's like, man, it didn't make it. Because it's only 22 minutes. So there's only so much that get put in and they still have to make a show. So yes, definitely. And I hope it's on some sort of streamer that we could say whatever we want really to really show and show and tell. Jeff Dudan (58:39.252) That's right. Jeff Dudan (58:46.964) Yeah. Casey Webb (58:48.494) you know, not just, you know, show, you know, and I think that therein lies the brilliance, you know, to really, to dig deep into that stuff and really get dirty, you know, cause it is a, it's, it's a dirty job. All of it, the restaurant business, you know, it's like, um, but you know, I wouldn't change any of it. You know, like I, I, uh, yeah, some of my, my, my closest people in the world are restaurant folk from, you know, top to bottom all over the place. So. Jeff Dudan (59:00.564) Yeah, it is. Jeff Dudan (59:13.3) Well, I for one appreciate Man Vs Food. You're incredible on the show. I watch it all the time and appreciate what you do there. Last question for you today, Casey. If you had one sentence to make an impact to speak into somebody's life based on your experience, what would that be? Casey Webb (59:17.454) Oh, thank you. Casey Webb (59:22.478) Thank you. Oh, uh -oh. Casey Webb (59:33.486) I have it written at my desk and it says focus on the work. And it's, um, that can mean, uh, cause often, oftentimes we get like caught up and we've talked about this in this past hour plus, or however long we've been talking, but it's when, you know, if you just focus on the work, I really feel everything else will be there, whatever that work is and just get out of your head and physically take action, take the action to do the work and, and, uh, you know, trust in that and breathe through it. Jeff Dudan (59:38.612) focus on the work. Casey Webb (01:00:02.83) You know, so focus on the work. That's something I tell myself every day. Jeff Dudan (01:00:07.7) Casey, this has been awesome. Thanks for being on. Casey Webb (01:00:09.998) Thank you. I appreciate you. And let's do this again. All right. Jeff Dudan (01:00:13.972) Yeah, 100%. Casey Webb with Jeff Duden, and we have been on the home front. Thanks for listening. Casey Webb (01:00:20.91) Thanks guys.

Brief Summary In this value-packed episode of On the Homefront, Jeff Dudan interviews Kevin Short, founder of Clayton Capital Partners and the author of Sell Your Business for an Outrageous Price. With over 45 years of M&A experience, Kevin shares war stories, pricing psychology, negotiation strategies, and practical wisdom for business owners looking to maximize their exits. This episode is a must-listen masterclass in running a competitive sale process, understanding buyer behavior, and avoiding costly mistakes. Key Takeaways You Only Need One Buyer, But You Need 150 to Find Them : Kevin’s proven process starts with 10,000 prospects and filters down to 15 serious offers to generate bidding pressure. Outrageous Prices Are Real—but Only With the Right Process : Strategic buyers sometimes pay double the average EBITDA multiple if the deal solves a big enough problem for them. Your Competitive Advantage May Be Hidden : It's not always your product—sometimes it's your location, team, or how you fit into the buyer’s existing business puzzle. The Willingness to Walk Away is Crucial : Sellers must be trained to maintain leverage, stay quiet, and let their advisors control the narrative. Terms Matter More Than Headline Price : Earnouts, rep & warranty insurance, IP structuring, and holdbacks can make or break your outcome. Choosing the Right Advisor Is Mission-Critical : Past client references, industry trust, and battlefield-tested negotiation skill matter more than a slick suit or fee structure. Featured Quote “Sellers are not professional sellers. Buyers are professional buyers. That’s why you have to level the field with process, preparation, and representation.” TRANSCRIPT Who Is Kevin Short? 45 Years of M&A Experience Explained Jeff Dudan (00:03.776) Welcome everybody. This is Jeff Duden and we are on the home front. And today we have a guest that I've been trying to get on for quite some time because of the impact that they made in my journey and what I learned from their book, Sell Your Business for an Outrageous Price. Welcome Kevin Short. Kevin Short (00:22.222) Thanks, Jeff. Excited to be here. Jeff Dudan (00:25.208) Yeah, yeah, fantastic. So I've been looking forward to this. Kevin, can you give the listeners a little short synopsis of your background? Kevin Short (00:35.074) Yeah, absolutely. Grew up in St. Louis, which is where I'm located still. Came out of school, went into the financial advisory business for about 10 years. And during that time, clients, local clients that wanted to acquire businesses, had me go out and do that for them. And so that's where I began to learn the M&A path for I'd call entrepreneurially owned company. So. The companies I've learned how to do deals with are anywhere from 10 million to 200 million. And my practice is all over North America. So we're an investment banking practice. All we do is M&A. All we do is privately held companies that have decided to sell. Jeff Dudan (01:22.068) And was your background in accounting or finance? What were you trained in originally? Okay. Kevin Short (01:26.378) Yep, finance. Yep, St. Louis University, finance. Jeff Dudan (01:31.68) Yeah, well, my brother, he's got a son who's a pitcher at NC State University. And he told me when he was young, he said, if you love your kid, you'll teach them to bat left, throw right. And then I've added, and learn finance. So I've added that on. You know, it's the money. It's the science of making money with money. Kevin Short (01:44.302) Hahaha! Kevin Short (01:47.634) Yeah, that's exactly right. Kevin Short (01:53.77) Yeah, absolutely. It's a fascinating time. It's very challenging every day. A lot of creativity is important. Negotiating is important. Salesmanship is important. Jeff Dudan (02:05.188) Yeah, and you've really seen the rise of private equity throughout your career. Can you speak a little bit about that? Rise of Private Equity and Why You Must Run a Competitive Sale Kevin Short (02:11.07) Yes, I started 45 years ago doing deals and private equity was nowhere to be found. They were there, but they were very small. Today, we track 4500 private equity groups and we market our deals to them because we never know where the right buyer is going to come from. We will slice and dice the database because there are some private equity groups that are more on point than others. And then of course, we go out to the Kevin Short (02:40.578) The deals we have, you know, it's not like you're selling IBM to GE where everybody knows who the buyer and the seller is. We have companies that most people haven't heard of, so we've got to find the buyers and get them to the table. So in our process with private equity, with strategic, private equity is by far the largest number of respondents to our different marketing efforts. But the A&A... we close about 80% of our deals with private equity. When we go to market, we will market to 150 folks will raise their hand, sign an NDA and say, we wanna look at your deal. So that's one of our advantages is we put in the hard work to make sure we have plenty of qualified buyers at the table because when you go to ask for offers, which is a big part of the process, if we do not put a selling price, as you know from reading the book. We ask them for offers. You better have a lot of people there at the table because many of them don't want to participate in an auction or they don't want to pay the price. But if you have plenty there, at the end of the day, you only need one buyer. And so that's what we do. You start with 150. We start with close to 10,000 prospects. 150 will raise their hand and say yes. I'll sign an NDA. That 150 melts down to about 50. And that 50 turns into about 15 offers when we ask for them. That's the process. Jeff’s Franchise Exit: 120+ Offers, 10 Finalists, 2 at the Finish Line Jeff Dudan (04:15.9) That's my experience as well. We were represented by Boxwood, Pat Gallaher. Really, they've been exceptional inside of the franchise space over the last five years. I think AdvanaClean, my company, was their second deal in the space. Did a great job. I think we had 121, what would be, indications of interest. And then I think 35, maybe, LOIs. And I think we had 10. Ten came, we put ten in for management meetings, and we ended up with two at the end of the day that were right down to the end there, so. Kevin Short (04:51.826) Yeah, that's an excellent auction result. Jeff Dudan (04:55.808) Yeah, yeah, it really was exceptionally well done. We had a good product. There was people looking. I've shared some of the wisdom in here and I pulled the book back out and I found all my old highlights in it. And again, it's sell your business for an outrageous price. If people are out there thinking about selling their business, it's a highly recommend because the book is so... easy to read and understand. It doesn't get into the technical aspect of finance. But it really, I mean, it'll give you some diligence lists and things like that. But what it really gives you is an understanding of what the process needs to look like. So you're a seller and you're unsophisticated. You've never sold a company before. There's a real chance that you can get taken advantage of inside of that process. And there was four things and I've... I've changed it a little bit over time, but now I got right back to it, looking back in the book again. But there's four things that you recommend as pillars of a good deal and a good process. One is that you need to have a competitive advantage. I've said you've got to have a competitive advantage that you can articulate, that you can prove, that makes sense. The second thing is you've got to find the buyers, which means ultimately you've got to run a competitive process. Four Must-Haves for Selling a Business at Maximum Value so that you can find enough buyers of interest so that you can find the best buyer inside of that. Number three, you've got to have a seller who, and this is the way I've said it, is who will keep their mouth shut and who will be willing to walk away. I mean, even inside of our deal, and we were clearly represented by an investment banker, I was getting calls on the back door, people trying to. you know, get in touch with me and see where I was, maybe emotionally around the business, or, you know, just trying to, you know, break, you know, subvert the process. And so really, the seller has to, has to maybe just watch the process happen and then be, people have to believe that the seller's gonna be willing to walk away. Because if you don't have that, then you're really putting your representation at a disadvantage in their negotiation. Jeff Dudan (07:12.992) If they know you're not gonna walk away, then I've just cut the legs out from under you if you're advising us. And then the fourth thing is, is you've gotta have proper representation. You've gotta have a great advisor that's done this before, has relationships. I would even go farther as to say what I've learned in the last five years is somebody that the industry trusts, that when they do the diligence or quality of earnings and they put the SIM together, Kevin Short (07:13.302) Yeah. Kevin Short (07:19.202) Correct. Jeff Dudan (07:40.844) and it's all out there that you're a reputable company, they know you've done your homework and that you're gonna be able to defend at the end of the day what you put in that SIM. So. Kevin Short (07:50.41) Yeah, that's an excellent, all those points are dead on, of course. Uh, the buyers have to be able to check out the investment banker and they've got to be legit. If they're not, they don't even play because that, that becomes too expensive for them. But you're right on. And what started the journey, Jeff, going back to one of your earlier questions, it's been 15 years ago that I had a company that I took to market and a steel service center. And the only. We had several buyers that came to the table. They were bidding around a five multiple. And that's what I was expecting. One buyer offered a 10 multiple. I thought they'd made a mistake. I did not mention that to them. And we kept moving forward and we closed the deal. And I ran into the CEO about six months later on a golf course. And by this time, I assumed he had figured out that he paid twice what he needed to. and he's holding a driver in his hand. I thought, oh, this could be nasty. And he I went up to ask the pet, tell me how it's going. He said, it's unbelievable. He said, you know, we close that one plant that was losing a lot of money. We have rid of the union. We did this. We did that. All the things they knew they were going to do. I did not know as a seller rep. I did not know any of that. He did. The buyer always knows what they're going to do. And that's part of the process for me to assume that I know what this is worth to a buyer. Jeff Dudan (08:53.452) I'm going to go ahead and close the video. Kevin Short (09:20.35) is a critical mistake. You have to assume nothing. You have to assume that the buyer knows what you're doing, you give them the data, you then have to work your process to get them to go to the highest level they can. So today, that's what our process is built around, how to find buyers that will pay two times or more the average EBITDA, the average multiple in that industry. So in your industry, EBITDA was probably quite a bit less than you got. you found the right buyer that was willing to pay more. So that's the magic. We were all trained in the investment banking business that you go for an average EBDA because nobody's going to pay you more. Why would a sophisticated buyer pay you more? The answer is if they have to, they will do it. The “Outrageous Price” Deal That Sparked the Book Jeff Dudan (10:08.912) Yeah, in our process, all business owners generally that have a business of size are going to get inbound solicitations from potential buyers, strategics. And over the years leading up to my sale, I had gone through the process with very large industry players, sophisticated players. And I... Engage the process, you know Not that seriously, but hey if I can give some information and figure out what somebody's willing to give me and I worked really hard with one inbound buyer and Ultimately, you know it came down to it and they made me this offer And I know I know they felt good about it But I when I was sitting with the ceo and he made the offer I could see his eyebrows went up and he really wasn't like It's almost like, is he gonna take me seriously on this offer? And then less than 14 months later, I sold my business for five times what that offer was by running that process. Kevin Short (11:16.61) Right, exactly. But you did the critical part. You read the buyer. You knew, because we do it over and over again. I will explain it often to clients. I might make my money, I would earn my money, in about a 10 or 20 second bite. If you saw the eyebrows, you've earned your money. That's where you made your money, right there. You knew he wasn't serious. You knew that was not his top number. Jeff Dudan (11:23.553) Yeah. Kevin Short (11:46.626) So you're right on, you're right on. Jeff Dudan (11:46.832) That's right. Yeah, that's right. And then, you know, and of course, we weren't running the process. So there was nobody else. So and they knew that. There's buyers. You know, everybody tries to make money when they buy something. OK. Kevin Short (11:53.611) Right. Kevin Short (11:59.338) They're professional buyers. This is what they do for a living. Sellers are not professional sellers. It's a big difference. Jeff Dudan (12:05.172) That's absolutely right. Yeah. So going down these pillars, competitive advantage. You know, if you're kind of in a me too business, what would be an example of a competitive advantage that somebody might not even know that they had, or if it doesn't exist, then is it more difficult to get two times the average EBITDA multiple? Why Competitive Advantage Depends on the Buyer’s Blind Spot Kevin Short (12:31.814) It is because the competitive advantage changes. The competitive advantage to one buyer may be very different to another buyer. We sold a company that was in the fresh produce processing business. So truckloads of lettuce would show up every day on one side of the building, and it would move through the building and be washed and sliced and diced. Nothing magic about that, right? It's a plain Jane business. Jeff Dudan (12:41.218) Oh. Kevin Short (13:00.13) What we found was a buyer who was very big in the industry, but their coverage was the perimeter of the US. So there's this big donut hole in the middle. So we went to the buyer and said, we have somebody that fits right into your donut hole. We are willing to sell for a seven multiple, which is what the industry multiple was. So we're not asking for anything more, except. we're going to multiply the amount of EVDA you're going to make by eliminating all that deadheading going back and forth to the middle of the country, all that wear and tear on trucks, all the new business you're going to make up and pick up because you're going through the middle of the country. And our estimate was we had to build a model that said that our EVDA was going to double because of these changes. And so we're not asking for a higher multiple, but we doubled the EVDA, which then doubled the price. So we got there through a different way, but that wouldn't have applied to almost anybody else. This was a very unusual situation. So their competitive advantage for this buyer was very different than the rest of the industry. Jeff Dudan (14:10.924) Well, that's exceptionally well done because typically, or at least what people have tried to tell me is that the efficiencies go to the buyer. So if, right? I mean, so, but if, yeah. Kevin Short (14:22.57) They tried that. Yeah, they tried. They tried that. But think about that backwards. They weren't going to get these efficiencies with anybody else. So that was that was our advantage. If they wanted those efficiencies, they had to buy us. Jeff Dudan (14:33.348) That's right. Jeff Dudan (14:38.496) Yeah, so really it's like a big puzzle when you're going out to the marketplace and, you know, taking what you have against all the different strategic buyers, even P.E. backed or not, and trying to find the one that's going to get the biggest lift immediately by integrating the company. Kevin Short (14:58.87) Absolutely. We sold an IT company. They were building software for prisons and jails and court systems. And we held an auction, 10 offers. They grouped around a five and one PE group offered 11. And again, we didn't point that out. And we closed the deal. How One PE Buyer Paid Double Because of an Internal Problem Jeff Dudan (15:24.464) Thank you. Kevin Short (15:27.438) come to find out they had bought another similar company six months before but much larger and they had all kinds of trouble and our client was going to fix those troubles. Our client, they fit together so well that the PE group said look we know we paid too much but it didn't matter because it was fixing a multi hundred million dollar problem we had. That's exactly what happened. See again I would not have known that unless I could have read the buyer's mind. Jeff Dudan (15:54.872) right. So we've talked about competitive advantage here. We've also touched on process earlier. That's kind of what we opened with. I wanna get to the seller behavior. And the way that you said it is, you gotta have a seller who's willing to walk. How does that manifest in behavior or inside of a process? How did they know? How do you communicate to a potential buyer who may be re-contracting that? this seller is ready to walk. Kevin Short (16:28.438) Well, because they generally don't believe that when you say it. So part of what we have to do is train the seller. We call it, when a seller gets so excited, their eyes get big, eyebrows go up. They may puddle out. They get up from their chair, there's a big puddle in their chair from all the excitement. So if we have a seller like that, we have What Makes a Great Seller? Trainability, Discipline, and Silence Jeff Dudan (16:32.281) Right. Kevin Short (16:58.338) their access to the buyers. That's job one. Job two is we train them like crazy. Because at some point they're gonna meet that buyer. We have to train them to be able to impress and convince that they're going to walk away, that their advantages are truth. And don't be counting your chickens. We had a seller, you would love this guy, bigger than life. He was in the hazardous waste business. He's hauling away all the sharp containers from hospitals. And that business goes for about a four or five multiple. He had gotten an offer from the big dog in the industry, the biggest dog in the industry. It was, I didn't say that. That's exactly who it was. Jeff Dudan (17:38.564) probably stare a cycle, but you didn't say it, I did. You didn't say it, I did, but I know they rolled up, I know they rolled up like 30 businesses in like seven years or something. Kevin Short (17:49.994) Well, so they know this story because they've heard me say it at different conventions. They don't like it. So they offered our client a four multiple of a one and a half million dollar EBDA. Okay, six million bucks. Client came, but they walked away at the 11th hour. We never knew why. So he hires me 11, 12 months later, tells me the story. So we spent two weeks in my office brainstorming on a whiteboard. Jeff Dudan (17:55.426) Ha ha Kevin Short (18:18.682) Why in the world were they here in the first place? He was awfully small. And we came up with some theories and those theories became the premise of our marketing effort. So we had a premise that we thought that he was so good at marketing that he had wrapped up St. Louis market, but he hadn't expanded. You know, imagine his skill sets in New York or Philly or Chicago. So we went, the good news is, in the hazardous waste business, the good news is when you pull a permit to open up a location, It's public information. So we went to those cities exactly and pulled permits that we were going to open a facility there. He gets a call within a day. You know, Regis, what in the hell are you doing? You're going to hurt yourself. You don't know what you're doing. If Regis, we had scripted everything. Tell them, look, we're not for sale anymore. Cause they said, why don't we come down to St. Louis and talk about buying you again? He said, I'm not for sale. He said, but if you're willing to sell some of your locations, we can talk about it. So this threw him completely off balance. And I said, all right, hang up the phone, let's go quiet. In the meantime, we pulled some more permits to other cities. And they said to him, how are you gonna do this? He says, I have a private equity partner, I have an investment banker, we're going to grow like crazy. Well, they were the big dog in all the markets. For him to grow, the market share, the market itself wasn't growing, he was taking share away from them. So they knew. And they... knew his skill set. So they called back two weeks later. They called me this time. And they said, we want to buy your client. I said, no, thank you. I hung up. Now, this is a guy who puddles out on a regular basis. And I had to keep calling him and saying, Regis, they call. I told him to get lost. He said, I hope you know what you're doing. I said, me too. So they call again in two weeks. And I said, well, let me save you some time. We believe this business is worth, let's see, about a 20 multiple of the EBDA. So we were talking about low $20 million. And they said, you're crazy. I said, okay, thank you, goodbye. Hung up. I never hung up on somebody so many times in my life. They called back the next day and said, all right, we're not gonna pay you $22, $23 million, but we could pay you $14. I said, no, thank you, and hung up. Now, I have a problem. The Hazardous Waste Deal That Jumped from $6M to $20M Kevin Short (20:46.846) I've got to call Regis who needed the money a lot and tell him it is offered 14. He goes, hey, that's amazing. I said, well, I hung up. He goes, what? I said, yeah, they'll call. They'll call back. They call back an hour and a half later. They said, well, we'll pay you 18. I said, no, thanks. I said, save me the trouble here. If you hit 20, we'll do the deal. I don't want to keep hanging up on you. He said, all right, we'll do the deal. So the next problem was we had to go through due diligence. You know, if they're going to spend $20 million for a company that's worth $6 million, they want to make sure they're getting something for their money. And I prepared Regis, I said, Regis, this game is far from over. They're going to try to walk away and call your bluff several times. And they did. We kept walking away. And gluten the day of closing, which is what they did to him the last time, because we knew that was coming. So we said, no, thank you. And they called back in an hour and a half and closed the deal. He was so excited. He's still living large. off the closing. He calls me on a regular basis as he drives by my office in his Bentley. He said, I just got a new Bentley. Thank you. So it's a great story. Great guy. He was a good seller. He studied hard. He came in here one day with six suits. He said, pick the one that's going to make the right impression. So he was really into making the impression and studying his script. Jeff Dudan (21:54.436) Love it. Kevin Short (22:13.11) But you have a client that has to take, you got to have an investment banker that believes, that he believes in because it's going to challenge his logic. And so they have to believe it. I've had attorney, you have to have attorney on board, either will stay quiet or believe in the process. I've had attorneys say to the buyer, I don't know why you're talking about 11 multiple, this business, you could get it for six. I'm like, the hell are you doing? I called a client, told him he fired the attorney, of course. Jeff Dudan (22:13.53) Yeah. Jeff Dudan (22:42.841) Yeah. Kevin Short (22:43.126) But people just don't believe that people, that buyers will pay twice as much for the same business, same EVDA, as everybody else is paying half price. So you learn a lot. You learn a lot doing deals. Jeff Dudan (22:57.328) That's the ultimate game of chicken. And in my experience with the investment bankers I worked with, in my deal, I know when the money was, I know when they earned their money and it was right at the end. And I did a testimonial for these guys and I was just like, you gotta have somebody that's gonna be able to stand tall in that pocket. Kevin Short (22:59.506) It is. Kevin Short (23:15.485) Exactly right. Jeff Dudan (23:23.348) at the fourth quarter on the 10 yard line going in. And it has to happen because, you know, there was a couple of pullbacks there. And he ended up getting me like, I have just an extra several million dollars for something that was already included in the deal, but they didn't understand that it was. And I heard him quote it. He quoted it to him and I'm like, well, that's art. And he's just calm and... Kevin Short (23:43.983) Right. What you do with Jeff. Jeff Dudan (23:52.076) you know, Tom Brady like, so it was awesome. Kevin Short (23:55.355) Right. All the mistakes they make like that, well, we didn't understand that. It's always in the same direction against the seller. They never make mistakes the other way in overpaying. So it's fascinating. Picking the Right Investment Banker: Ignore the Suit, Ask Their Clients Jeff Dudan (24:06.548) Yeah, fascinating. So if you were going to advise somebody how to pick an advisor, an investment banker, what are the couple of things that somebody should consider? Kevin Short (24:17.218) Well, as I say often, be careful because investment bankers all buy their suits in the same place, have the same haircut, they look sharp, look professional, they speak the language. None of that matters. You've got to talk to their past clients and tell them how it actually went. How did it go when that 300-pound lineman was breathing down Brady's neck? Did he stand tall or did he bail? So the clients know that. Jeff Dudan (24:30.48) Yeah. Kevin Short (24:46.198) So you've got to have documented proof that they can do this. And there really are not very many people that can do it. There's a lot of investment bankers in the world that get paid very well because it's a very profitable industry, but there aren't very many people that do it well. So you've got to find the one that does it well. Jeff Dudan (25:05.368) Yeah, and you can't really be that fee sensitive. Everybody, all the good ones have a very similar model. But when I had that single inbound offer, I was working with somebody who was a tax advisor, but they were also a business broker. And I would happen to be meeting with him. I said, well, this is what this company offered. And he knew what my financials were. He goes, that's a pretty good deal. That's about what we would get you. And I like, but I already knew what I thought market was. because other people that had sold. And so I knew that it was way short and that I was gonna ultimately go and run an auction. But again, if this was my trusted person and they told me that that's what it was worth and I went with it, then I would have ended up with 20% of what I ultimately ended up with. And things would be really, really different. Kevin Short (25:55.089) Yeah, yeah. Your intuition was very good. Jeff Dudan (26:19.062) Yeah, and Jeff Dudan (26:25.216) associates working on deals. Well, I mean, I've got, you know, my son's a finance and econ major. He works with me now. My daughter's a first year law student in NYU. Her boyfriend's working in investment banking in New York. He's working on deals, right? So there's junior people that are doing the work. But I would also suggest that people should know who's the quarterback on my deal. And if you take too small of a deal to too big of a firm, Kevin Short (26:42.59) Absolutely. Kevin Short (26:48.15) Yep. Jeff Dudan (26:52.62) you might not get the talent on your deal that you need. Kevin Short (26:56.842) You don't want you're exactly right. You don't want to settle for low talent. You want the highest level talent who has the experience that you need and do not settle. Price vs. Terms: Why “All Cash” Isn't Always All That Jeff Dudan (27:07.34) Yeah, yeah, 100%. So I do trainings occasionally for franchisors. And on the second day, I open up, I bring in my deal binder, which is about 15 inches of paperwork, maybe in four or five different binders. And I slam it down on the table. And I say, I said, this is the paperwork. Kevin Short (27:08.851) expensive. Jeff Dudan (27:37.004) from when I sold my company. And I ask him this open-ended question, what do you think is more important, price or terms? Kevin Short (27:47.466) Right. It's terms. Terms. You get the biggest price in the world if you never collect it. Jeff Dudan (27:47.692) I'll ask, and I'll ask you. Jeff Dudan (27:55.928) Yeah. Tell me, tell us what you mean by that. Kevin Short (28:01.814) Well, they could wrap you up in earnouts and all kinds of weak notes for a big price and you'll never see the money. So you want the big price and you want excellent terms. You gotta have both. But the terms, the terms gotta be there. All the non-competes, all the intellectual property ownership, because we carve our deals out. It may be better for you to keep the intellectual property as a seller and sell that later. There's all different ways to skin a cat, but you've gotta have somebody who understands all that. Jeff Dudan (28:17.007) Yeah. Jeff Dudan (28:34.136) Yeah, so if you have all your IP in a separate company and you've been charging 1% lease to the company for it or something like that, and maybe you put that... I know a guy who has a 4,000 unit chain in one of the franchising here and I was talking to him and he took all their IP and their trademarks and it's a place where... It's a well-known place that cuts hair and he put... all their IP into a separate company and they lease it back to the franchise or and that's in his trust for his kids. So it's, you know, yeah. Kevin Short (29:11.21) Yep, that's smart. In case it doesn't work out, he can start up a different company the next day using an IP, because they will have blown the non-competes by not paying him. So that is very smart on his part. Jeff Dudan (29:24.608) Yeah, yeah, so sharp, sharp guy there. The other thing is like what kind of a basket, how reps and warranties insurance is a big thing. You sign off on all these representations and all these warranties and it's 50 pages of things that there's gotta be all kinds of little gotchas in there. You do it with the best of intent, to the best of your ability, but then will the buyer pay for. Insurance that if something does come up that was a violation of a rep or warranty that you made that it first goes to insurance And you know, that's important how much hold back how much of a basket how long? And are there any financial markers that have to be hit for you to get the rest of your money? I mean Um, I know I have a horror story here And i'll share it because people need to know Had a friend they had a contracting business They were in business with family. It wasn't really working out. They had started, some of the family had created the misalignment by creating a compatible but separate business without all of the original shareholders in it. So they were looking to sell and cash out of the original business. And I mean, it was only a $15 million deal or something like that. But it was negotiated over a very long protracted period of time. and there was only 30 or 40 percent of the money down and the rest of it was on an earn out. And the day after closing, the acquiring company filed a massive lawsuit challenging all the reps and warranties on the deal. And it devastated this guy. And they spent all they spent more than half the money that they had gotten up front in legal bills over the next two or three years, trying to work it out. And ultimately they didn't get. Kevin Short (31:07.722) Well, well. Jeff Dudan (31:21.568) I don't think they ever got anything more out of it. So that's the worst story I've ever heard. And come to find out after the fact that as they investigated it, they were able to find people. This was a pattern of behavior from this buyer. But they tie everybody up with gag orders. So you can't find anything about it online or whatever. So. Kevin Short (31:42.954) That's sad, that's sad because the entrepreneurs worked their whole life to build these companies. Jeff Dudan (31:48.268) Yeah, and I mean, possession is 9 tenths of the law. So if you would have got all your money up front and maybe a million dollars in escrow, then okay, they can argue over that million, but you got the majority of your money and you walked away with it, and then now they've got to come get it. So that was. Kevin Short (31:50.582) Yeah. Yep. Deal Killers at the 10-Yard Line: Surprises, Employees, and FBI Agents Kevin Short (32:05.258) Yeah, to your point, you don't want to be chief with your attorney. You want the best M&A attorney you can find. And to your point, the referent warranty insurance has decreased the escrows from 10% to 5%, and that often the amount of cash in escrows are around 1% because you have referent warranty insurance. So the buyer is protected. It's good. It's money well spent. Jeff Dudan (32:10.893) Yeah. Jeff Dudan (32:26.732) Yeah. Yeah, not cheap, but again, on the terms, you put it in the stipulations that the buyer has to pay it. Kevin Short (32:36.886) Yep, yep, exactly right. Jeff Dudan (32:38.976) Yeah, and then they're not arguing with you. It's probably easier too. They just make a claim. They get their money. You're not litigating over it, that kind of stuff. Kevin Short (32:46.59) Yeah, in the insurance companies, you'd be in the middle. So they know they don't have a rookie defending the claim. They've got a sophisticated insurance company defending the claim. Jeff Dudan (32:59.256) So you're in a deal and you're driving down, you're on the 10 yard line, you're going in. At that point, what are some of the more common things that kill a deal? Kevin Short (33:13.206) I would say things that pop out of due diligence that the seller didn't tell anybody, including us. That's a biggie. Sellers believe they're going to get away with it and they don't. We are very aggressive about keeping it quiet because the other thing that happens on the 10-yard line is key employees get wind of it and they either come in and try to hold the seller hostage. I understand you're going to get rich next week at a closing. Jeff Dudan (33:20.969) Oh. Jeff Dudan (33:35.919) Yeah. Kevin Short (33:42.57) I want $10 million or I'm walking out the door today. I've had that happen. We use stay bonuses a lot to make sure the key employees stay during the process. But I would say surprises and due diligence are the number one thing we worry about at the 10 yard line. Jeff Dudan (33:45.614) Right. Jeff Dudan (33:53.583) Yeah. Jeff Dudan (34:02.756) So it could be a payable or a liability that they conveniently forgot to tell you about. It could be a legal thing, a claim that was in their past or something like that. Diligence is pretty thorough nowadays, especially in our industry. There's been so many deals inside of franchising that there's specialty firms. If you just hire the right three or four specialty firms, they're gonna go through all the franchise agreements. They're gonna call every franchisee. They're gonna talk to them. They're gonna... Kevin Short (34:14.826) Absolutely. this. Jeff Dudan (34:32.2) They're just gonna dig, right? So. Kevin Short (34:36.458) And there's the unexpected, the surprises. We had a company that was manufacturing military-grade equipment, and we were within a week of closing, and a client called me and said, bad news. Last night, the FBI hired our China sales representative. He was selling secrets to China. And that, of course, blew up the deal. You could not have predicted that in a million years. Now we got it back on track and closed it. Jeff Dudan (34:57.886) Mm. Jeff Dudan (35:02.841) No. Kevin Short (35:05.634) But it was really a curveball at that point. Jeff Dudan (35:08.94) Yeah. So Kevin, when did you write this book? And was it written for anybody in particular? I mean, obviously, it's a great tool for business owners like myself to read and to get a little familiar with the process. It's also a great marketing tool for you, because you are definitely an authority inside of this space. You know, when? did you decide to write this book and what was the catalyst that triggered you to do it? Kevin Short (35:42.11) Yeah, going even further back than I said earlier, I had written it with a ghostwriter and we wrote it over a year and it was terrible. I just couldn't get onto paper what I was trying to say. It's hard to explain why somebody would pay twice the average price, the average multiple. So I finally found an editor. Jeff Dudan (36:06.189) Yeah, right. Kevin Short (36:10.494) And she and I would talk every Monday morning for two hours. And then she'd spend a week putting it on paper. And then we would review the next Monday. And this went on for five years. And it, oh yeah, it's, we, because we were, it was such an abstract concept. And our publisher, Amicomp out of New York, they did a worldwide search trying to find who had written a book about this subject. And surprisingly, nobody had. Jeff Dudan (36:21.68) Oh my goodness. Kevin Short (36:39.626) So it wasn't even a guide to use. How do you talk about this kind of pricing? So that, it was written for owners. Those were my clients, but it's become a textbook. It's used a lot in seminars all over the country. And advisors buy it quite a bit. We're about to go to our fourth printing because advisors are buying them up to give to their clients. They want their clients to sell so they can manage their money. So all those markets we didn't really expect. We sold about 25,000 copies. People bought it in Barnes and Noble in Vancouver to get on a plane in two days and come down and visit me. Crazy, crazy stories. But that was the whole goal. We didn't know where it was going to go. We just felt like if people were to read it, that they would get it. And they do. Jeff Dudan (37:38.816) I've recommended it to so many people and have borrowed from the insights as I coach people on how they need to think about what it looks like at the end. More just trying to slow people down and just say, look, hey, I got a call. I'm an owner in a men's clothing business. And it's... Kevin Short (38:05.827) Whoops, whoops. Jeff Dudan (38:07.712) It's no, it's good. It's a franchise. It's, you know, trunk shows and all kind of that. It's a really Kevin Short (38:09.408) Was it? Okay, good. Kevin Short (38:17.214) They stayed current. Good. Jeff Dudan (38:19.064) Yeah, it's a really, really cool business. Great product, good service, still kind of at startup phase, but a lot of people are jumping on board with it. And lo and behold, we put a suit on an athlete that wins a national award, and that commercial comes out, and now all of a sudden, there's a multi-billionaire reaching out saying, I want to invest in the business. And... Kevin Short (38:47.388) Smart. Jeff Dudan (38:48.436) And he's, but he's engaging one-on-one with the founder. And I'm just like, hey, this is a sophisticated group of people that you're dealing with, an entire team of finance people. I said, you know, if you're serious about taking on this, and I mean, they were, you know, there'll be an investment, right, if the deal goes through, but I mean, don't think for a minute that there's not gonna be claws for people to claw up. you know, above 51% or, you know, whatever the game of it is, or you're going to have to hit markers on it. So I kind of use the, you know, I use your book to say, look, you know, read this, look at this, look at these chapters. And you know, when you need to be, you need to be very thoughtful about, you know, trying to thinking that you can negotiate with somebody that's made billions and billions of dollars buying and selling companies. Kevin Short (39:46.522) That's a good thing. So sellers, you know, these entrepreneurs that we all know and love, they've made their living by their wits, right? They're very good at selling, they're very good at reading people. They think it applies to this process. It does not. Selling, you know, I-beams for skyscrapers does not equate to selling a business to Blackstone. So you have to accept that you're overmatched in bringing professional help. Kevin Short (40:42.946) Yeah, I didn't get it. Mine says we're still recording. Okay, we can do that. Okay. No, no, of course not. Kevin Short (40:55.171) Okay. Kevin Short (41:53.517) I can. Can you hear me? Kevin Short (42:00.616) Hello, hello. Kevin Short (42:42.779) How's that? Kevin Short (42:46.81) Can you hear me now? Kevin Short (42:51.174) Hello, hello. Jeff Dudan (42:51.386) Yeah, it's so crazy. I didn't even have to hit the record button, but I can't hear him. So see if you can hear him on your... I know you can hear me because he just refreshed. Jeff Dudan (43:04.984) It's so strange. It just started recording itself. Jeff Dudan (43:11.076) Kevin, do I got you? OK, yes, sir, thank you. There, I don't know. That hasn't happened for a while. We used to have that, where it would stop. But we're recording, and we're going, and Jim, we'll edit this right together. What was my question? Where were we? Where do we leave off here? We were talking about. Kevin Short (43:11.13) Hello? Yep, can you hear me? Kevin Short (43:33.498) the value of the advisors, not doing this on your own, no matter how good of a salesman you think you are. Jeff Dudan (43:35.668) Yeah. Not doing it on your own. Yeah, yeah. And we were talking about your book. OK, how it was used and all of that. Awesome. All right. Jeff Dudan (43:51.372) Kevin, what's the most creative deal name that you ever assigned to one of your deals? Kevin Short (43:57.054) We don't do that. That's funny you say that. We just put numbers on them. Yeah, yeah. Jeff Dudan (44:00.772) Oh really? So when you call somebody it's not project seaside or project airplane or jet. Kevin Short (44:06.202) No, no, we just did do, you know, we did do one recently for the first time. The client wanted to use a name instead of a number, but we use numbers so we can keep track of all of them more easily. Jeff Dudan (44:17.96) Well, sure, it's yeah, that makes sense. Yeah, all right, well, so much for that theory. I have that theory. Kevin Short (44:20.502) over time. That's funny. Kevin Short (44:27.653) Right. Jeff Dudan (44:33.664) So one of the things that you do, how much are you working doing investment banking? And then I also would love to talk a little bit about your radio show. Kevin Short (44:43.474) The radio show, this one, so we did a podcast for a couple years. Did two, two years of podcasts, about a hundred episodes. And then KMOX came to me and said, what do you think about being involved in the show? So I joined them as a sponsor first. And I sat in the studio doing recording and watched, and then just became an on air host, co-host. with a legitimate Radial personality in the stainless market and so I'm there asking questions. So that's that is all You know, we're going I say bigger time this year with the show but we've been doing this for probably four or five years and lots of Video and podcast over the years a lot of speeches So we learned how to market probably 15 years ago and learned that there was never enough marketing. There's cheesy marketing, so we avoided that. But if you're putting out a good product and you're building good lists, there's never enough because you never know when that next lead's gonna come from. And the marketing is what's fueled our business. In the book, the book really was, put us on the map. Jeff Dudan (46:11.092) Yeah, 100%. The show is The Business of Family Business. It airs on KMOX, which is 1120am throughout the Midwest. It's a pretty strong signal. And based right there in St. Louis, what day and time are you on? Kevin Short (46:25.894) Saturdays at 2 o'clock. Jeff Dudan (46:28.008) Okay, is it an hour? Man, how fun is that? And you've got the same co-host every time? Kevin Short (46:29.614) It's an hour. Yes. Oh, it is. Yep. And I get to meet crazy people. I love business owners. I always have. And I really have a lot of respect for them. Jeff Dudan (46:46.916) Is it like a Dave Ramsey thing where you're just constantly taking calls? Kevin Short (46:51.202) No, we don't take calls at all. We actually record ahead of time. We've talked about that. Can we get enough listeners that we could do a live show? As of right now, we don't do that. Jeff Dudan (46:54.621) Okay. Jeff Dudan (47:04.96) I started doing a navigating entrepreneurship webinar once a month, six in the evening, Eastern time. It comes out of our Facebook group and navigating entrepreneurship on our Facebook group. We got a lot of, it started small and now we've got more people showing up. It's the closest thing that I could do right now to a radio show where you've got interaction with an audience and people popping questions in there and things like that. I find it to be a lot of fun. It lights me up. It's, I mean, we had everything from, we had a guy who's an international board director and was the CEO of a huge company that sold for maybe $500 million and he pops in there, right? And then I got another guy that's a yoga instructor. And. Kevin Short (47:53.019) Right. I've had the same experience. But you have to love entrepreneurs because they're not perfect. You're not perfect, but they are very talented at what they do. Jeff Dudan (47:58.593) Yeah. Jeff Dudan (48:02.412) Well, what's interesting is they're engaging with one another and respecting one another and solving, you know, everybody has similar problems regardless of the scale of the business. So it was really, really interesting to see who shows up on that. But then I would love to do a live radio show or even record it or something like that. Kevin Short (48:21.262) Oh, it's interesting. It's, it's, it's fun. People over town here on their car radios and call me and say, I heard it. Uh, but you know, these entrepreneurs, as you and I have figured out, they all have a very different form of genius. And that's what's put them on the map. It made all their money. Jeff Dudan (48:36.435) Mm-hmm. Jeff Dudan (48:40.212) Yeah, yeah, it's interesting. And you spent a lot of time, it looks like, with charities in and around children. Kevin Short (48:47.618) I do educating children. In St. Louis, we have a race issue. And my solution to it, going back 30 years, was to try to develop schools that would lift these kids up out of poverty. And so I teamed up with the local archdiocese, and because they had the schools and the teachers and they had empty desks, and so we found donors, the big corporate donors in town, to provide the... tuition. So we launched that formerly 15 years ago and raised about $200 million over that 15 years and educated about 5,000 kids a year, which in St. Louis was a lot of the kids in poverty. And it was a grand slam. And those kids went on to college. And so we tracked all of them. And there's a national program for this called the Children's Scholarship Fund out of New York. that I'm on the board of and have been for a long time. And so I learned a lot from these programs around the country. But we were very, very lucky to have the board members, the staff and the donors, they were willing to support the cause. It was unbelievable. And to me, it was, since I've been in business for myself for a very long time, I don't have all that corporate training that the IBM guys do or the Goldman Sachs guys. I learned my training in the not-for-profit world. Jeff Dudan (50:12.341) Yeah. Jeff Dudan (50:17.3) Yeah, the same here. I've, it's been a long, long time since I worked for somebody. And all of my professional development I've had to pay for and learn through, you know, not failures, but, you know, I'm learning, but 100%. And, you know, we're passionate about Kevin Short (50:22.735) Right. Kevin Short (50:33.397) A chapter, they were chapters. Jeff Dudan (50:39.432) similar things. So we've partnered with Ben and Candy Carson and the Carson Scholars Foundation and Homefront Brands is building reading rooms across the country in schools in partnership with them and also participating in their Carson Scholars program where they give thousand dollar scholarships out and you can the kids can win them year after year after year. The money's put into an interest bearing account and then whenever they go off to school the kids get the money to use towards their education, tuition, books, or whatever it is. But as importantly as that is the events that they have where these kids who may not have had the opportunity to ever participate in something like that, they get to come to a banquet, they get an award, they get to be around other people, I mean, internship opportunities and all that kind of stuff. You know, and we like to say, there's the manufacturing analogy that says the earlier in a process that you can... repair a defect the cheaper it is to the overall production process. And it's kind of the same thing with children, the more that we can pour into them early. And we actually have a collaboration now that I think of it that was brought to me last week where they're looking for us at Homefront brands to build content that's targeted towards teens that are entrepreneurial, but is going to be safe for the kids. parents can comfortably go and say, you can send your kids here and there's gonna be guests and there's gonna be content for them that they can learn about business or about leadership or these types of things. And you don't have to worry that it's, people are gonna be swearing on it or there's gonna be other stuff that maybe they might not want their kids to be, they already consume enough of other places. So yeah, so I'm excited about that collaboration. Kevin Short (52:28.568) Right, right. Congratulations, that's a lot of hard work. Jeff Dudan (52:33.928) Yeah, yeah, it'll be good. But you know, we're kind of over that target already. I mean, it's not that big of a diversion for us to create that little channel of content there. And we've got great guests like you and other people that are coming on. So we're very excited about that. And we'll pursue that. Kevin Short (52:54.542) It's amazing what people will do. It's amazing what people will do to help others. You just got to show them the path. Jeff Dudan (52:58.612) Oh, that's what it's all about. It really is. All right. Well, this has been amazing, Kevin. I really, really appreciate you jumping on with us today. And again, I want to thank you because what I was able. I mean, I just on a whim, I said, I need a book that's going to teach me how I need to think about selling my business. This name popped up. Outrageous Price is attractive to anybody who's looking to sell. And so I just clicked. buy on Amazon and it really helped inform my thinking in a time when I needed it the most. So I appreciate that. Yeah, 100%. How can people get in touch with you today if you choose for them to or where would you point them to consume more of your content? Kevin Short (53:31.203) That's exciting. I'm glad it worked. Kevin Short (53:46.287) Yep, Clay You can reach me by phone, by email, and there's a lot of content that we keep up to date. There's other websites. So the outrageous word promoted a lot of marketing. So there's ThinkOutrageous.com. So we've had a good time with all that. So, but Clay dot com is the easiest and fastest way to reach me. Jeff Dudan (54:19.113) outs and spelled just like it sounds, C-L-A-Y-T-O-N, capitalpartners.com. And last question, if you had one sentence to make an impact in someone else's life, what's your go-to? Kevin Short (54:36.686) Don't give up. It's not about the fanciest degree or the fanciest anything. It's about understand yourself, spend time figuring that out, and then don't give up because it will happen. But many people give up on the 90th yard line and if they'd just gone a little bit further, they would have won. So don't give up. That would be my life story is just by persevering. Jeff Dudan (55:07.328) Words to live by with Kevin Short. I'm Jeff Duden and you have been on the home front. Thanks for listening. Thanks, Kevin. Kevin Short (55:17.179) Thanks, Jeff. That was excellent. Good job. All right. Thank you. Jeff Dudan (55:18.752) Yeah, man. Cheers. Hang on.

Brief Summary In this episode of On the Homefront, Jeff Dudan sits down with Stephanie Postles, founder and CEO of the Mission, a modern media company producing high-impact podcasts for Fortune 500 brands. From humble beginnings on the Eastern Shore of Maryland to working at Google and building a podcast empire, Stephanie shares her journey, insights on sustainable media, the future of storytelling, and her bold plans to transform kids' content, comedy, and more. It’s a masterclass in entrepreneurial grit, creativity, and purpose-driven media. Key Takeaways Early Hustle Creates Future Leaders : Stephanie’s childhood side hustles and DIY education in investing helped shape her unconventional career path. Google Recruited Her for Her Side Projects, Not Her Résumé : Her entrepreneurial experiments caught Google’s attention more than her finance career ever did. Media Must Be Owned, Not Rented : After Medium shut down her monetization, Stephanie committed to never building on borrowed platforms again. Podcasts Built for Brands, Not by Them : The Mission creates and owns its own shows while securing aligned sponsors—ensuring creative control and brand integrity. Internal Talent Is Strategic : Most hosts at Mission are employees, not influencers, allowing the company to maintain control, consistency, and culture. Kids Content Is Next : Stephanie is passionate about building value-based storytelling platforms for kids that go beyond screens and junk content. Featured Quote “You are 100% responsible, 100% of the time. Everything around you is being created by your thoughts, your actions, and the energy you’re putting into them.” TRANSCRIPT From Raking Yards to Rolling Silverware: Stephanie’s Scrappy Childhood Stephanie Postles (00:00.109) locally so it doesn't normally matter if it misses a few beats. Jeff Dudan (00:02.414) now. Welcome everybody. This is Jeff Duden. We are on the home front today with Stephanie Postles. Welcome Stephanie. Stephanie Postles (00:12.397) Thank you. Thanks for having me. Jeff Dudan (00:14.542) Yeah, very excited that you're here today. I had the opportunity to meet you over the last couple of months and learned about your podcasts and your interesting take on the podcast industry and how you've built a really powerful business off a really interesting business model. Before we get into all that, would you care to take us back a little bit and tell us who is Stephanie Postles? Stephanie Postles (00:42.189) Yeah, who am I? It's such a good question. So maybe I'll go, yeah. I mean, I'm like, wow, where do I even start? When I was four, who am I? Yeah, I'm like, that's still a question I'm constantly figuring out. Who am I today versus yesterday? But if I maybe go back to younger days, earlier days, you know, back in Maryland is where I grew up, Eastern shore of Maryland. And I grew up in a very scrappy household where, Jeff Dudan (00:45.71) Is it? Is it really? It's the one we have. Yeah. Stephanie Postles (01:10.957) It was known that you go and you do what it takes to get what you need, to get what you wanted. And so from very early on, like age seven, I just remember raking neighbors yards, doing really random things for people, putting some little stickers on the mailboxes for our neighborhood. I mean, anything that myself and I have a twin sister and brother could do. We were out there hustling, hustling all of our older neighbors to just give us a dollar to rake their yard for like two hours. And so that was kind of the early days of just. doing what it took, learning a lot. Got into the restaurant industry at 14, rolling silverware for about eight hours a day during the summers, just all day, outback steakhouse rolling silverware. And that was at 14, definitely highly illegal. Now when I look back, I'm like, pretty sure I know why I was getting paid cash now. And when I say sign no paperwork to get into that place and red lobster too, I was like, just in the back, just rolling silverware for so long. Jeff Dudan (01:51.854) at 14. Jeff Dudan (01:59.182) Yeah. Jeff Dudan (02:06.542) Nice. Stephanie Postles (02:07.437) But that was kind of the moment when I realized I don't like hourly pay. This doesn't work for me. I'm like working so long, so many hours, and it doesn't feel like I have a way to compound this quick enough to get where I want to go. And I knew what I wanted. I knew I wanted to get off the Eastern shore of Maryland. I wanted to expand my horizons. I just didn't see a way out really. I mean, my family was not wealthy growing up. Um, but what I did have was a really smart dad who was brilliant when it came to finances. lost a shit ton of money in the stock market though. So I also watched that too, where I'm like, he's really smart and whoa, over -hedged and lost everything. And it took, I mean, fast forward to today, I still don't know if he ever really climbed out of what had happened back then, but he taught me a lot about finances and he offered to open up a custodial trading account for me when I was 14. And he showed me how to read different stocks and how to think about diversifying. And for every hundred dollars I would put in, he would put in a couple of dollars too, just to kind of incentivize me to like put some money in your E -Trade account and just play around. And that was when I started seeing that there was a way out in different ways. Maybe it was going to be investing. Maybe it was going to be starting my own company. I didn't know what it was going to do, but it just couldn't be an hourly thing. So that was my aha moment. Stayed in the restaurant industry for a while because then I realized bartending could make you outsized returns for your investment of hours. So did that and yeah, I was like, this is actually pretty good now that I'm not on the hourly wage system. You know, I can use this personality for something and get paid. And then it got to 21. I had a finance degree at that point. I got out of college in three and a half years. Um, and I got an investment finance degree just because I was like, I don't want to invest other people's money, but I want to know how to do it myself. Um, and that was when I realized, I don't know if degrees really matter that much because I actually learned more just investing my own money. Jeff Dudan (03:30.638) That's right. Stephanie Postles (03:57.869) in my custodial E -Trade account than I did going through and learning the technicalities of, you know, how to do math by hand, which I'm like, this is dumb. I don't know how to do this and I don't really want to, but got out of school, um, got recruited by Fannie Mae, got to get into the whole mortgage space after all of that had crashed. So it was a really interesting boot camp to jump in, learn what the housing crisis was about, see how many people were underwater and then rotated through different finance and economics groups, um, for about two years. Jeff Dudan (04:26.83) So was that maybe 2009 you were in that? 2011, okay. So we were clawing our way out of it. Yeah. Stephanie Postles (04:29.261) That was 2011. Yeah, but it was still. Yeah. Yeah. I mean, the numbers were still, at least when I went in there, I was like, Whoa, I didn't even know this was still a thing. And it definitely was. There was just so, I mean, there was so much data to look at. And that was when I started realizing, like, if you have access to data like this, you really can create a lot. You can create a lot of, I mean, we were writing housing reports. I was so new and young, but because I had this power of data all around me and I was learning how to use SQL code to pull it, I felt super like powerful on top of the world. I can do anything if I have a lot of data and I can. Jeff Dudan (04:43.086) Yeah. Stephanie Postles (05:03.693) tell people a story around this data because most people don't know, you know, maybe how much in fees they're paying just to see if they actually own their land or how, you know, what should your debt to income ratio be? And what did it look like back in 2007? So super interesting. But then I started looking around one day and this was what I thought I always wanted. Every day I manifested where I got. Every day I would wake up in Maryland, in my parents' home and I'm like, one day I will be in Washington, DC and I will be in a white walled building with people in suits and it's gonna be so impressive and I'm gonna be so fancy. And then I remember looking up one day and I'm like, oh shit, I just got myself into this. I thought my way into this scenario and I put myself exactly where I imagined every single day without realizing it until a couple of years in where I'm like, I really don't like this. I don't like corporate. I don't like corporate finance. I don't like economics. Jeff Dudan (05:56.11) Yeah. Stephanie Postles (05:59.469) And I don't like, like being so far detached from the consumer where it's like, you don't even know who you're serving really. And so that was my first moment realizing one, the power of your mind. And I got myself into this now I need to figure it out. Um, and thankfully the universe came in and provided and Google reached out and recruited me. And that was where it kind of like many, many things changed. Um, but. Jeff Dudan (06:23.918) Were you a big reader growing up? I mean, I would think you would have to be. Stephanie Postles (06:27.213) Yeah. Yeah. I definitely read a lot of books, a lot of business books. Um, so the one part I kind of left off was that from about maybe senior year of high school, all the way up through Fannie Mae, I was always tinkering on things. And I was always thinking, how do I build a company? How do I build a product? How do I drop ship? I was looking into things that probably most 14 year old girls were not looking into. And I knew that because I had my twin sister reading the exact opposite from me. I would look over and she'd be reading these really sad, like teen drama girls dying from cancer, cancer when they're 15. And I'm like, Oh my God. I'm like, we're so opposite and we're twins. And I'm over here reading, you know, how to create a brand that lasts a lifetime or something. So definitely read a lot. My parent, my mom took us to the library quite often. We could get, you know, any books we wanted. And yeah, so I was always tinkering. Jeff Dudan (06:54.126) Right. Jeff Dudan (07:12.174) Yeah. Jeff Dudan (07:21.07) Who was the entrepreneur that you saw? Because generally, so an early entrepreneurial experience is almost always an indicator of future entrepreneurial success. People that are thinking that way and always trying to maximize their time and scrap for a buck. When you find successful people, you go back and that's what you find. But generally, they were exposed to somebody. Was your dad an entrepreneur? Was it somebody else that you knew? Stephanie Postles (07:49.805) No. Jeff Dudan (07:50.67) that you knew or the other side of it is you just needed money. Like that was mine. Like I needed money. Stephanie Postles (07:56.205) I think I just, yeah, I needed money because my parents couldn't pay for us. My mom was a teacher. And then we had a family of five and my dad didn't have a job a lot of my life. I mean, he was a stay at home dad for a while after the stock market stuff and then in and out of jobs, but really he didn't have one until today. Still he's at home. So I think I just saw to me like a scarcity mindset. Jeff Dudan (08:00.43) Okay. Jeff Dudan (08:13.454) Okay. Stephanie Postles (08:24.621) And then what it looks like to be confined in a salary and how I would see people around me wanting this, these big visions of like, I want this, I'm going to have a boat. I want like a condo in Ocean City. I mean, big visions, but even me when I was younger being like, well, if you don't change something drastically in your life and make some humongous decision that's outside of the path you're on, there is no way you're going to get there. Like there is no amount of interest that you're going to save or even a certain percent on the stock market that will get you there most likely. And so. That's, I think it was more of the need of like, okay, I can't do that. And it was just seeing what I didn't want. And I didn't have anyone around me. My grandfather was in finance. My grandmother was a teacher. The rest of my family's in Germany and other places. And I think it was more just the need for, I want to be able to make money. Jeff Dudan (09:11.694) I remember, and I don't know where it came from, but having a real fear of being trapped. And so taking, when I looked at, when I graduated college, I didn't take one job interview because I thought about it and I'm like, oh, I remember here's Ernie and Julio Gallo. They were recruiting on campus. They wanted to interview me and you know, it's like, well, you know, in the job and I read the job description, I'm like, well, you can be a wine distributor so I can go around to. Stephanie Postles (09:17.805) Yeah, yeah. Stephanie Postles (09:26.381) Mm -hmm. Stephanie Postles (09:34.413) Mm -hmm. Jeff Dudan (09:41.614) do whatever they do with their wine to put it in the stores and whatever. And I'm just like, yeah, but if I do that, then I'm trapped. And I'm trapped inside of that. So I think I've spent early in my career, in my first life, it was the avoidance of being trapped. And how that's manifested with me is I react negatively to leverage. I don't like, now I be very careful to put myself in situations where I lose my leverage. Stephanie Postles (09:48.045) Mm. Stephanie Postles (10:03.981) Yeah. Jeff Dudan (10:11.566) And sometimes when I've gotten situations where I've lost leverage, that's where I've lost money. So I don't know. But yeah, we're unemployable, Stephanie, is actually what we are. Yeah. Stephanie Postles (10:11.597) Mm -hmm. Stephanie Postles (10:15.725) Mm -hmm. Stephanie Postles (10:23.245) I know. Yeah. I think I felt trapped too, but in a different way, I was trapped to the Eastern shore of Maryland where I was like, just looking around and no one ever left and no one in my family ever left. Everyone just stayed there. And I saw how a mindset can get trapped in a location of just how easy it is to not know what you don't know. And so just be like, okay, I have a finance degree. I'm going to go and work at a bank. That's the Jeff Dudan (10:31.95) Okay. Stephanie Postles (10:49.293) or at the hospital, like that's the two best options for having a finance degree in my hometown. And just knowing that no one leaves and you stay with your family and here's my mom, like she wants us nearby and your grandkids, like it was just such a culture to stay there. And I just didn't know any different. But I had a feeling if I just got out for a little bit, I always thought if I go to DC, I'll come back. I'll come back to home and I'll just go and test it. I just want to try it. But then once I did that, then I kind of realized, oh no way, I cannot go. Jeff Dudan (11:13.326) Yeah. Stephanie Postles (11:19.213) back somewhere where it feels like any of my ideas were, yeah, squashed by anyone. I was really around because they just couldn't imagine things that I was talking about. And then when I went out to California and started working at Google, then I'm like, oh my gosh, I really didn't know what I didn't know. I mean, I, you just, the more you move around, the more you try, the more you experiment, the more you realize like how limited your mindset is and how small you're thinking until you just go and, I mean, to me, try things that are riskier, which now it sounds like you don't want to go too risky. I'm like, Jeff Dudan (11:29.454) Yeah. Stephanie Postles (11:48.845) I just want to try it all. I want to live my life and try everything. And even if it fails me in a big way, sometimes I'm pretty confident I can recover. I can get out of it eventually. Jeff Dudan (11:57.678) Yeah, yeah, for sure. So Google was recruiting and was it one of the puzzles where they put it up on a billboard and you have to, and only the smartest people can figure it out or did they tap you on the shoulder? Stephanie Postles (12:08.877) No, no. Yeah. So they tapped me on the shoulder, but they did not tap me on the shoulder for my corporate history. They, on my LinkedIn, I had listed a couple apps that I had built, an iPad magazine I had written, some books I had published. I had all these side projects of things that I had launched over the many years and they reached out and they were like, we have a couple of jobs we want to interview for. And when I got there, I realized they didn't even ask me once about Fannie Mae. They didn't even care any bit about my technicalities of finance. They were just like, we do have these jobs here, but we actually really just like all these startup projects that you've been doing. So tell us about those. And so that's when I also realized, yeah, yeah. Jeff Dudan (12:50.094) Yeah, smart creatives. Yeah, yeah. So like, I don't know how Google works, the book, I've referenced it several times, but basically built their entire company on smart creative, understanding how to identify those people and that just putting them in and giving them a lot of latitude to be great and to create. Was that your, that was your experience? Stephanie Postles (12:59.789) Mm -hmm. Stephanie Postles (13:05.517) Yep. And that's what they did. Yeah. And I'm sure I know it's not that for everyone, but when I came out, I interviewed for about five different teams and I got offers from all five, four of them, and they were finance offers, but four of them felt very much like I was going to become a part of a system. It was YouTube, it was ads, it was, you know, they're very well -known brands who were already built up. And so it felt like I was going to be going in there, just being a part of the financial system to report to Sundar. One of them though, felt complete opposite. It was a group called GEO and it was Maps, Street View, Google Earth. It was a whole mix of groups and they had never really had a finance person. They had a billion dollar P &L. And so when I was interviewing, it was very much like, well, we don't really know what you're going to do. So like, if you can come in and just like help tell us what to do, but then also we need you help over here and we need you to probably come to Japan and figure out the Street View cards there. And can you help us acquire this satellite company and - It was just all over the place. And I was like, yes, this is my style. I don't love structure. I don't like someone coming in and being like, here's your 10 things to do. And then you're done. I want chaos. I like chaos. That's where it's fun. Where I get to come in, build the systems, build the structure, and then get pulled into different things where I'm expanding my excitement into virtual reality. And then it does something very different in Google brain. So I took that offer and had the best time there. I mean, it was so much fun and so much chaos and. I saw what it looked like to really work under a really great manager. And it also made me realize how terrible my manager was at Fannie Mae back in the day where I was like, and it's good to have both. I was so grateful. I'm like, I didn't know. But then when I had a really good one who the one I was working for at Google, I mean, she would put me, I mean, there were no levels. There was no hierarchy. It was just like, here's Steph, go present this to the CEO. You want to do that with the budget? Okay. I mean, there was so much freedom to make the choices I want. And then. And I just didn't realize who I was working for in corporate finance back in the day versus how it could work if you really have a manager who stands for you and, you know, wants to promote you many, many times. Jeff Dudan (15:16.718) Yeah. Jeff Dudan (15:22.926) You know, as a couple, both of us building companies and I'm just, I'm the autonomy guy. Like I'm not a great manager, right? In terms of the blocking and the tackling. Well, part of it is definitely, I've never had a job. So, no, no, I had lots of jobs, but not like a real job. You know, like a perfect, like an adult, I've never had an adult job. Yeah, I've never worked in corporate. Stephanie Postles (15:40.845) You've never had a job? Like not even one job? Stephanie Postles (15:46.509) Yeah, yeah. Like corporate. Yeah. Yeah. Jeff Dudan (15:51.758) So I didn't, so I had to go out and get all of the training and stuff and all that methodologies, but, you know, you know, voracious reader, lots of professional training, lots of all through the years and all that stuff, just from, you know, the organizations and things like that, that you go to. But I still always come back to, if you want to have great people and you want to have A players, you've got, you can't define, the boundaries in which they're gonna run around and do it. I mean, you use your culture and your values to set the fence. So you give people a big yard in which to run around. You make sure that there's a clear mission, clear goals. Everybody knows like who, what we're really trying to accomplish, who the customer is, keep them front and center. You know, we build franchise brands and everything we do is keeping the franchisees at the center of everything that we do and every decision that we make. Because that's gonna keep you, that's going to keep you on track as to what's most important. But then, you know, as we build, we get all kinds of different managers that come from all kinds of different backgrounds and people want to put systems and constraints and these types of things in there. And, you know, really great people love to operate in a scrum or a small team to create things, to be brilliant, to test and fit, to see if it works. And, you know, if you over, if you over manage, and you over -checklist things, then that tends to be just what people do. Now, we also run a call center. So you gotta show up at this time. That's much more structured. So getting the right level of autonomy based on the team and based on the goals and the responsibilities of that area is critically important. But I've read How Google Works more than once. I highlighted it. I keep going back to it because, Stephanie Postles (17:20.973) Mm -hmm. You got to have a checklist for a call center. Yeah. Yeah. Jeff Dudan (17:45.102) That's the kind of company that I'd want to work at. That's the kind of company that I'd want to build. And, you know, I believe one day they'll be very successful. Stephanie Postles (17:53.517) Yeah. Yeah. I mean, I'm, I hope so. I mean, I don't know with all this stuff coming out right now. I'm like, Ooh, looking a little bad, looking a little scary with how fast the market's developing. So to be a big company right now, I hope they figure it out because they were really fun. And I mean, the smartest people in the world that I was working next to every day where I'm like, this is such a treat. Yeah. Jeff Dudan (17:56.686) I'm not there. Jeff Dudan (18:03.534) They'll figure it out. They'll figure it out. Yeah. Jeff Dudan (18:11.502) 100%, 100%. Awesome, so how long were you there and how did that run its course for you? Stephanie Postles (18:20.557) Yeah, I was there for four years or so. Um, and after about two years, I started getting a little bored because I had a process built. I was like, okay, this is how we run the finances for this group is how y 'all get the budgets. It's how we do experimental projects. And so then my manager was like, well, let's put you over here. Let's try and promote you into this group. And so we tried and we tried to move me around in different ways. Um, but in the meantime, I started mission. Jeff Dudan (18:24.59) Okay. Stephanie Postles (18:50.445) Mission started though, as a very small side project on a platform called Medium. And I started it with my ex -husband, now ex -husband, but back then it was just a blogging platform where we were just submitting our stories to our, you know, our Medium publication. And we were trying to pull other people into the writing of it as well. And so we were reaching out to all these writers like, Hey, would you want to come and submit your story here? We saw a really great story you posted here. Can we put it on our publication? And so it was really just this very scrappy act of we wanted to tell the stories we wanted to tell. I wanted to tell the stories of these executives that I was sitting next to at Google and some of the trends that were happening in Silicon Valley. And then also just stories that I thought were really interesting that needed to be told. And we wanted to promote other people's work that we liked as well. So that's how that started. It was super slow on the side. A lot of working on the morning, working on it throughout the day, the evening, trying to just pull people into the vision of like, you should write for us for free. And give us your content and we'll put in our publication that one day we'll have a lot of views. It doesn't right now, but I think it will one day. So that was how it started. Um, and then over time it actually did grow and it became the top publication on medium. It had millions of people viewing our publication every month. We had hundreds and hundreds of some of the best writers who were. Actively pursuing us because they knew if they put their article in our publication, they were going to, going to get a lot of views on it. And so it started just taking up a lot of time and we thought. We should monetize this because right now I have no incentives to be working with all these writers who are texting me all day and begging me to approve their content and edit it and asking me about metrics and why they are something. I mean, it's just so much time. And so we thought we should get a sponsor for this publication because there's so many millions of people coming and reading our content. Why not? I think that's how this works in this world. If you have a big audience, you should get a sponsor. And so we struck up a couple of very, very small ad deals, just banner ads. And we put these banners on the publication and very soon after the medium team who was on their own, trying to create their own publications and they were competing with us and they were trying to get our writers to go to them. And they were trying to write similar content. So it was kind of already was feeling a little bit weird where I was like, don't you want this? Like, don't you want us to have people coming here? And now you have these competing publications that of course you're going to win. This is your platform. You know, the rules, you can change the rules whenever you want, but. Jeff Dudan (21:14.574) Right. Stephanie Postles (21:16.749) We kept building, we put these banner ads on and then soon after about two weeks later, Medium was like, you can't do that. You guys are not allowed to run any ads on your, any of your stories and we're building an ad platform and you have to run through us. And that's the only way it can work. At that point, we didn't have any of our readers contact information, emails. I mean, we really didn't even know who we were really talking to. We just knew it was a lot of people. And that was kind of the aha moment of we don't want to build anything on someone else's platform. Like we don't want to be. I mean, they can just change the rules anytime they want and it's their platform. And then you're shit out of luck. And you're like, okay, I just kind of built a business on someone else's platform. And now, you know, I can't do anything with any of this. And so that was back in 2017 and podcasting was still pretty new back then. Um, but we saw the potential and one of the stories that we had written on this media and publication was called the story. And it was telling the unknown backstory of people who changed the world. And we would keep their identity hidden until the climax. So very hero's journey, but we did it for a reason because we saw that a lot of people in the Bay area were very pessimistic towards people who were literally changing the world. They were like, Oh F Elon Musk. Oh, that person's stupid. And like, we're like, man, I feel like this person did a lot before what you see now. So maybe if we just tell you the story in a human centric way, without telling you who they are, you'll have a little more respect towards what these people are doing. And so. Jeff Dudan (22:18.702) Oh, yeah. Jeff Dudan (22:35.438) Yeah. Jeff Dudan (22:42.926) Yeah, some objectivity there, right? You know, like, okay, I'm judging it on the merits of the fact pattern that I'm reading. And when you get to the end of it, and I'll tell you what, Mike Rose podcast, he had little bits on there, like the 15 minute things, but like he had a podcast and he would do the exact same thing. And at the end, it was always some like hook about, and that's, you know, that's how Pringles were made or something, you know. Stephanie Postles (22:44.717) Mm -hmm. Mm -hmm. Stephanie Postles (22:49.421) Yeah. Stephanie Postles (22:54.253) Yeah, yeah, dirty jobs. Okay. Stephanie Postles (23:08.749) Yep. Yep. Jeff Dudan (23:09.486) And it was all but like it was you never knew where it was going in the story and you couldn't click away because you had to hear the end now that you were invested in it. So what a brilliant strategy. Stephanie Postles (23:15.629) Mm -hmm. Yep. Yeah. So this format's definitely not new. I mean, I think there was a radio show in this exact format a long time ago that did really well as well. Um, but yeah, this one, it was just super fun. And we got to tell so many stories and looking to so many people's backgrounds that, you know, a lot of them, I just didn't know about and didn't know all the stuff they had done to get where they were. And so that medium pub or that story really took off. Um, the whole, all of them did. And that was when we saw like, man, this could do really well if it had audio, if it had. something to really pull you into the story. And so we took this format and essentially pitched it to Salesforce because they were already in our network. We already had someone connected there and we just pitched it to them and said, Hey, do you want to sponsor this show? And so that's how the company mission really turned into a media company was because of realizing like we have a great story here. It's already doing well in written format and we think we can turn this into a podcast as well. And so. Jeff Dudan (24:16.814) Yeah, so it's podcasting in reverse. It's, yeah, finding a sponsor who would be the perfect fit for the show that you want to produce and then building the show for the sponsor. Stephanie Postles (24:19.789) Yeah, for that one it was. Yep. Stephanie Postles (24:31.885) Yeah, we don't build it for the sponsor though. So they can always sponsor our stuff, but it's not theirs, which is very intentional. But yeah, for almost all of our shows since, and now fast forward to today, we've built 33 different podcasts. And we call them shows because they're also all in video like this. They've got video clips and all that. But fast forward to today, we do, before we ever build a show, we also already have a sponsor probably lined up for it. But Mission, it's still a Mission -owned show. We're hosting it. Jeff Dudan (24:35.758) Okay. Stephanie Postles (25:01.389) We're growing it, producing it, distributing it. And then we've got these big sponsors like Salesforce or New York stock exchange. They're sponsoring these shows because it's aligned with what they want to do. So it is a bit different of a model. Um, and like I said, it was very intentional because I saw what media was turning into on medium and has always been that way of just race to the bottom, you know, get as many views, as many clicks as you can fear -based. And I just didn't want to operate in that model. So I thought, how can we. Like, how can this be sustainable? How can we do this long -term? How can we actually partner in a way that isn't just more, more, more, but quality, reach the right audiences, get the right guests on, have good content, and just create a sustainable company instead of one that probably will be competing with the gimlets and the wonderies who are all just trying to get more eyeballs on them on everything. Jeff Dudan (25:53.07) What is your strategy around talent? Stephanie Postles (25:57.165) Yeah, you mean like the hosts of the show, the shows? Yeah, so it's an interesting question. Well, look, you're already one, you're already a famous host. Oh man, I knew there was an ulterior motive. Always, yep, at the end. So most of our hosts are mission employees. I do this because I'm unsure and I never wanna say, Jeff Dudan (25:59.47) Yes. And how can I be one? How can I be one? Now this is just an audition for you. Jeff Dudan (26:11.374) Yeah, there always is. There's always an ask. Stephanie Postles (26:25.453) never and I, my, most of my strong opinions are very weakly held and so they can always change if I get better information, but I'm not sure if I want to deal with talent, really someone who, you know, there's so many creators out there, amazing ones, but they want what they want and they're the star of the show. And that's great. If you're already getting millions of views and you've got your audience, like, Keep doing it and then get the brands who want to reach the consumers, get the B2C brands who are selling the socks and the meandis like perfect. But if that's not you already and you don't have that, and then you want to be, you know, a host for instance, I just think it can get tricky around making sure that mission, my company's happy, the host is happy, and then the sponsor's happy. And there's so many people to keep happy. And I find that if someone is like, I'm the talent. It can turn into a bidding war. It can turn into, okay, well, even though mission, this is your show. Now I've got this captive audience and it's, you know, this is my thing. And I mean, you've seen many podcasts hosts run up the price of like continuing a podcast. And so that was also just a game that I didn't really want to play. And I do hire hosts, um, outside of, uh, my employees sometimes if I create a show and we have a sponsor and I'm looking around and I'm like, man, I really don't have someone on our team who. Jeff Dudan (27:18.67) Yeah. Jeff Dudan (27:32.526) Yeah. Stephanie Postles (27:45.005) is the subject matter expert about that. And so, for example, Experts of Experience is a show that we have and it's around customer success, customer experience. And I was looking around, I'm like, I don't know anyone on my team who can really speak well to that, which most other topics, I'll say you can. I've hosted a commerce show, I've hosted a marketing show, most other things you can learn pretty quickly just by interviewing 20 people. And all of a sudden you're like, okay, like for e -commerce, I'm like, I can talk to you about supply chain and logistics and all the things now just from. researching, getting on some newsletters and then interviewing. But some things I think you might want to be a bit more of an expert in, especially for bringing on the Fortune 500 to get onto a show as guests. Like that's who you're gonna be talking to. And so for that show, I was like, we need to find a different host outside of the mission team. And so we found an amazing one who was recommended to me, which I also think is very helpful when your friends are sending people to you, because they're like, you know who Steph likes, we know what she's looking for. Jeff Dudan (28:24.558) Okay. Stephanie Postles (28:40.045) Um, and finding someone who this could really benefit them. So it's a win -win. It's not someone who is desiring to be the talent and the influencer or anything like that. It's someone who, you know, they are in customer success, customer experience. They maybe want to start a newsletter. They do some consulting work. Um, and this is a great opportunity for them and us. So I try and find win -win scenarios like that where it is, um, it's just a win -win and it's not someone holding power over the other. Jeff Dudan (29:07.15) You make an excellent point and I just want to double click on it for the audience because it went by really fast. And it has to do with when you're building a business, where do you allow yourself to be middled? Like where are the opportunities of failure for you? Because, so I'm big on collaborations. When we were there, when we were together, we were at an event and there was sessions on collaborations and collaborations are great because everybody's sharing their expense. Stephanie Postles (29:35.533) Mm -hmm. Jeff Dudan (29:35.63) in a way to build a project. And okay, that's great. But at the same point, if you don't have control over it, now there's different leverage points inside of that project inside of that deal. And then like you did on medium, you built this great property, and you spent all this time and energy and skill and expertise to pull that together. But at the end of the day, you didn't have control over it. So you decided you had to go another direction. So by having Stephanie Postles (30:01.069) Mm -hmm. Jeff Dudan (30:05.518) control over who the hosts are, you know, you just can't be middled and you can't be leveraged by something. So, but guess what? You have to pay those people. So, you know, the bigger budget you have or the more risk you're willing to take, you can definitely shift the risk in your direction and, you know, minimize it and things like that. So for people that are building a business, those are decisions that you make every day. And sometimes it's not at startup. Stephanie Postles (30:24.621) Mm -hmm. Jeff Dudan (30:34.99) because you do whatever you can to spin the wheel and get the business going. But then as you grow your business, you're going to be faced with these things. And I see it a lot in technology. I see it a lot with marketing vendors. Hey, we have this incredible platform and it does everything. And we'll just drive all the leads and we'll do that. I said, well, okay, what about the data? Well, that's going to be on our platform. I said, well then. you know, how do we disengage, how do we break up and how do we get our data? Oh, well, we're going to have all the data. And, you know, so there's no build, you just start right now, but just realize long term value, 84 % of the value of transactions today are in the IP and in the data. So, you know, if you abdicate your data, which is probably the wrong word, somebody can look that up. Stephanie Postles (31:07.149) Mm -hmm. Jeff Dudan (31:27.758) If you let somebody else own all your data, then you've really devalued your business. So I just want to, it's really interesting to me that you came to the decision to employ all of your talent. And because the other side of it is I was thinking, I was actually thinking it was going to go the other way, because I was thinking about the analogy of reality TV. You know, I've done some reality TV. Stephanie Postles (31:41.773) Yeah, yeah. Stephanie Postles (31:49.037) Mm -hmm. Jeff Dudan (31:51.982) And it was amazing. It only costs about a million dollars to produce an episode of Undercover Boss, where an episode of Friends, it's $10 million, and it's all in talent. So it's the same production cost, but so the reality TV is so pervasive because there's no cost for the talent. People just do it for free. They'll do it for their 15 minutes of fame. For whatever reason, they want to do it. Stephanie Postles (31:59.373) Mm -hmm. Stephanie Postles (32:05.453) Mm -hmm. Yeah. Stephanie Postles (32:13.613) Yep. Jeff Dudan (32:18.862) And podcasting's a lot the same way. I mean, we're just regular people, but trying to build a platform. So anyway, interesting, but sorry for the digression there, but I just found that to be a really thoughtful strategy that you employed there. Yeah. Stephanie Postles (32:38.477) Thanks. Yeah, it was very, very helpful for sure. And yeah, you just see how when your employees get the choice also to work on things that maybe they might feel they're not even qualified to do. And they're like, I mean, I remember a couple of people I hired. They were just like, wait, you're going to put me in front of Fortune 500 chief marketing officers. Why? I don't even know marketing. I'm like, you don't need to know marketing marketing. You just need to like know how to pull out a good story and know what things to drill in on. Jeff Dudan (32:51.662) Yeah. Stephanie Postles (33:06.765) You just have to be curious and be smart. Like go read some newsletters. You'll figure it out. But I mean, it doesn't, for most of these shows, it doesn't take someone who is an expert. And actually when someone is an expert in the space, then they're just going to do all the talking. And I'm like, that's not what I want. Like if you're, if you're too much of an expert and you're like, well, I've been a CMO for 50 years, who's probably going to run the conversation. So I'm like, I would rather have someone who, you know, is actually a little bit more of a newbie and ask the questions that everyone wants to know anyways. And. Jeff Dudan (33:28.302) That's right. Stephanie Postles (33:34.925) Yeah. If you can be a heartfelt person who just wants to bring out a good story, you can interview almost everyone. Um, I will say our one show that that does not work for us. It visionaries where we interviewed chief technology officers and chief information officers. So very technical it people. And thankfully I did have someone on my team who has a background. He used to be a CIO at this big company. And so he had the background, but that's one where I'm like, just being loving and heart centered doesn't work for like that group. You really actually have to know it, but. For the most part, many people can host if they're just curious. Jeff Dudan (34:08.75) Yeah, it makes sense. So what was your breakout podcast? Stephanie Postles (34:13.069) So, I mean, right now of all the years, I'd say the one that I'm hosting Mission Daily is probably our breakout one. That one gets about a million to 2 million downloads a month. So that one's our top performer, but I will say most of our shows, we don't just want more. We don't just want more downloads because our shows are focused on a niche audience. They're focused on having the chief marketing officer listen to it or the customer experience officer. So a lot of our shows, we don't want... Jeff Dudan (34:19.502) Okay. Okay. Stephanie Postles (34:41.549) a million downloads on it because we're actually probably not reaching the right people. If we're getting that big of an audience on a C level marketing show. And so most of our shows, we don't view it that way. We might view the, like the success for those shows as who were the guests that came on? Like, Oh, we just had today, the CMO of Sotheby's come on. Like that's a pretty big company and that's a great person to have on and to share their knowledge. And they've never really done a podcast before. Like those are the metrics for success for some of those shows. Um, But then mission daily is much more entrepreneurial focused. I mean, I talk about so many contrarian things sometimes on there. I think of course it's going to draw a bigger audience because I'll talk about almost going bankrupt, getting divorced when I'm pregnant, building mission backup, crypto, psychedelics. I mean, I talk about so many things that are a little more click worthy where people, yeah, they just want to listen to that more. It's just a bigger audience. So that one does do well. Jeff Dudan (35:33.422) Yeah. Jeff Dudan (35:40.526) Most shows that I've seen fall into categories of either educate, entertain, or even inspire. When you're looking at a show, most of yours are going to fall in the educate category. Stephanie Postles (35:45.645) Mm -hmm. Oh, yeah. Yep. Stephanie Postles (35:55.341) Well, do you remember when I pulled out my notes about this too, where I was like, that was like the vision of mission is inspire, educate and entertain in that order. Yeah. Where we both were like, what? We both have the same vision statement for our companies. Jeff Dudan (36:03.054) Oh, that's right. Yes, that's right. Jeff Dudan (36:08.686) Yeah, and you asked me, said, well, what does the show do? I said, well, we educate, entertain, and inspire. And you pulled it, and you had it on your paper. That was so, yeah, that's right. Yeah. Stephanie Postles (36:12.941) Yeah. Yeah. Yeah. Yep. Yeah. So, I mean, I'd say a lot of our shows, we want to do all of that. Um, yeah. So it's in that order though, for us inspire, educate and entertain, but a lot of the content we're like, just because it's executive, you know, executives being featured, doesn't mean it has to be lame. It can still be fun. Um, and interesting and exciting and how you can cut these clips up can be fun. So I think you can do it with all kinds of content. Everything is just how you structure a story and how you can relate to that person. Jeff Dudan (36:36.046) Yeah. Stephanie Postles (36:46.253) Yeah. Jeff Dudan (36:46.99) So what makes a good guest for Mission Daily? Stephanie Postles (36:50.381) So for Mission Daily, I sometimes have guests on there. It used to be very guest -driven. And then we kind of shifted away from it, but guest -driven as in it'd be the people that, like authors like Annie Jacobs would come on or Marissa Mayer came on. So it was like higher profile people in the Bay area where it's like, those people were very exciting to have on back then when we started this show. And then over time, it just... Jeff Dudan (36:56.494) Oh. Jeff Dudan (37:06.126) Sure. Jeff Dudan (37:15.534) Okay. Stephanie Postles (37:20.237) To me, I'm like, those conversations weren't always the most interesting. Sometimes they were, but sometimes if someone was a brand name, they came on, you're like, eh, you're a little too like PR focused talking and that's not fun for me. So, yeah. So it shifted a bit away from that where now if I have someone on, they're probably my friend. They're probably someone that I think is just doing fun things. And, um, yeah, I want to bring more attention to what they're doing. So that's. Jeff Dudan (37:30.766) Yeah, little too careful. Stephanie Postles (37:48.077) kind of what's happening now. So right now it's mostly just me and then my COO at the company who he's been at Mission for a long time. He has seen Mission through so many ups and downs and we have a very great dynamic because he's so opposite from me. I'm like woo spiritual, like doing things over here and he is very like logical, just not woo at all. And so it's an interesting dynamic because we're always on such opposite ends of the spectrum when we go through just different topics. Jeff Dudan (38:08.686) Yeah. Jeff Dudan (38:16.686) Interesting. So what's going on with Coachella this year? Tickets are available. Have you heard that? Stephanie Postles (38:20.749) No, I don't, I've never been to Coachella. So what's up with Coachella? I feel like that's what younger people go to, right? Jeff Dudan (38:24.974) Okay. Well, I would have thought well, that's why I thought you'd have been there Stephanie Postles (38:31.085) No, I go to Burning Man. Burning Man is a yes, but Coachella just feels like, I mean, I'm sure it's cool. I don't know, but yeah, I would probably keep going to Burning Man instead. Jeff Dudan (38:33.55) Oh, okay. There you go. Yeah, I'll... Yeah, absolutely. Are you going this year? Nice. OK, I think we talked about that too, actually. Yeah. So, well, awesome. So your vision for the podcast going forward, what's the next iteration on this? Have you thought about how to grow it? I mean, obviously, it's doing very well. Stephanie Postles (38:44.397) Mm -hmm. Yeah, that'll be my third year. Yeah. Yeah, yeah, I think so. Jeff Dudan (39:08.686) It's gotta be very rewarding financially and otherwise. What's next for you? Stephanie Postles (39:15.021) Yeah. So next is, I mean, continuing. I know, right. I did actually, someone called me out there like, wait, are you just bored because mission's working now? Because they're like, you seem like you were having a lot more fun when your company was almost bankrupt and you were getting a lot more exciting out of like excitement out of saving it. And they're like, and now it's stable and you're talking about moving on. So for mission, I mean, I am still so excited about bringing more like B2B enterprise, SaaS companies. Jeff Dudan (39:16.622) Cause you're bored by now. I know you're bored by now with this. You've been doing this too long. Jeff Dudan (39:29.262) Oh. Yeah. Stephanie Postles (39:42.381) into sponsorship of our model because our model admission is so different than any other podcast. And so just bringing more tech companies into it to show them how to really use media strategically and how to actually get an ROI on media. So I still love that space. We have more new sponsors coming on than we have before and really fun ones and great ones that I'm super excited to work with, which is I think a very big shift this year is anyone I work with gets to be fun. I get to like the team, I get to like the product, and I get to like the partnership, which was not always the case. And there's been a client in the past that we actually had just be like, we're not working together anymore. And that's a new thing for me. And so this year, just finding really innovative, amazing SaaS companies who want to tap into the sponsorship model. And then... Jeff Dudan (40:30.702) Yeah. Why are people like that, Stephanie? Why are people like that? You know? Like, I want... Stephanie Postles (40:37.197) I don't know. And I think when you're an entrepreneur, you just say yes in the early days because you're like, well, I have team members and I've got payroll and I have things to do and I just have to pay my bills. And you say yes. And then six months later, you're like, God, this person's annoying. Like, why? Why am I letting them pay me pretty small amounts at this point? Jeff Dudan (40:49.294) Yeah. Jeff Dudan (40:53.87) I don't know why people like it's being hard to work with makes the work harder. And it's it really does. And it's it you know, I don't get it. I do pick and choose a lot who and some of the networks that I know you go to and that I'm involved with, man, it just seems like these are really high level people. They set a financial bar where if you want to work with me, I just hired somebody and. Stephanie Postles (40:59.789) Mm -hmm. Mm -hmm. Jeff Dudan (41:23.726) great marketing mind. And literally he said, it's a $25 ,000 rate card. And then he wouldn't tell me with any detail what he was gonna do. He wouldn't like, and then so I just said, well, give me some references. So I call these references, like this is the best person ever. They've 10x to my business, just do everything that they say. It's so great. And I really had some great conversations with this person and I liked them, but he had just decided he didn't wanna fight over money. Stephanie Postles (41:35.501) Yeah, uh -uh, that doesn't work for me. Stephanie Postles (41:47.629) Mm -hmm. Okay. Stephanie Postles (41:53.069) Mmm. That's good. Jeff Dudan (41:53.358) and he knew that he was good and he knew that his reputation and his references. So I just paid it. And then we had our first call and it was the greatest thing ever. I'm like, this is the most brilliant marketing mind I've talked to. And he says, that's included. I said, well, tell me how this is gonna work. No, we're doing it all. We're doing it all, we're gonna handle it. It's only gonna take this long. We've already got started on it. Stephanie Postles (41:59.661) Hahaha Stephanie Postles (42:06.893) Okay. Jeff Dudan (42:21.774) And it was just, it was the best experience, but like the $25 ,000 was a qualifier so that he didn't have to work with people that he didn't want to work with. And he didn't have to jump through hoops trying to sell it. And I think kind of the higher up you go into things, you know, you're going to find people out there that take that position. And I, you know, I just find it really interesting, but man, I do, I just want to work with people that are up to something, going somewhere creative. They're cool. They have good perspectives and um, Stephanie Postles (42:26.797) Mm -hmm. That's good. Stephanie Postles (42:47.757) Yeah. Jeff Dudan (42:50.766) And they're out there. You just you just have to. Yeah. Stephanie Postles (42:52.077) Yep. You just gotta take, it takes a while to learn that. I mean, I think, and you can't demand those things upfront. Like you have to work with shitty clients, some like in the beginning to then figure that out. And like, that's something where I'm like, man, started this company in 2017. And as of like this year, I'm finally like, no, now I can demand that I want to work with cool people. It took that many years of really taking what I had to, to build a company. And I think, so you have to be a certain. Jeff Dudan (43:01.582) You do. Stephanie Postles (43:19.405) space in your life and with referrals like he has and a background to be like, okay, now I've elevated and I don't need to actually prove myself because my referrals will speak for me. So that's pretty baller. He sounds great. Jeff Dudan (43:31.79) So if somebody came in and bought the whole thing from you today, of course, you've got a young family, but you were completely free to go and do anything that you wanted to do and you had no more, they didn't even want you involved at the company anymore. Where would your feet be in three to six months? Stephanie Postles (43:57.389) Well, I mean, I actually think about this often, because I think it's a good thing to think about. It would probably be doing something similar to the things I'm doing now around these new shows I'm launching. So we have all this business tech content, executive content, founder content. That's been our network for, you know, since we started. But this year we had a goal to launch 10 new shows in Q1. And these 10 new shows were not business tech or any of that. They were... Jeff Dudan (44:02.35) It is. Stephanie Postles (44:26.861) very outside of that space. They were around spiritual concepts or one's called like sacred echoes. And it's highlighting these spiritual sites around the world and what's happening there, just showing like the unification of experiences of what's happening in Russia is happening in Sedona, it's happening in here. And so these things I didn't care about 10 years ago, but then after many different experiences and having kids and all this kind of stuff, fast forward today, I care about a lot of different stuff. And so, that kind of content we're putting out. We have a show coming out on Shipwrecks. I've got kids content coming out, which I have four kids. So looking at the media space for kids is like appalling to me. And my kids don't do screens. And so it'd be good for them to listen to good stories with good intentions behind them. So just launching new shows and probably getting into comedy and some reality TV, which now that I know that you did that, I might talk to you, but just trying new things in media, because I do think... Jeff Dudan (45:03.118) Yeah. Stephanie Postles (45:24.973) media has the power to impact and influence generations to come in such a great way if you have good intention behind it. And so that's what I would still do just, and I'm doing in a different way. Even if I had all the money right now and mission was fully taken care of, I'd be like, okay, what new things can I launch that will change the world? Jeff Dudan (45:39.118) Yeah. Jeff Dudan (45:46.702) Well, so what's beautiful about that answer is you're already doing it. Stephanie Postles (45:50.413) Yeah. But it's because I was asking myself that question a year ago, two years ago, um, because building a company is not always, you know, like it's not probably where you can make the most money always. And so I think it's good to step back and check of like, is this still worth it? There was many times where I'm like, I could just jump back to my job at Google and make more money right now and have a way easier life working nine to five than I am right now worrying about X, Y, and Z. Jeff Dudan (45:52.078) Yeah, that's awesome. Jeff Dudan (46:06.094) Yeah. Jeff Dudan (46:15.854) right? Stephanie Postles (46:20.109) And so there was so many times of me thinking of like, okay, would I want to do that? Cause you know, that's a lot easier. And yeah, asking myself that question and being like, okay, I still would do this on the side though. I would go back and I'd work at Google and then I would start doing this on the side again. And then I'd be back here again. So it's definitely not the money that's driving this always. Um, and you know, it's nice, but it's a good question to ask yourself. Jeff Dudan (46:44.558) I'm interested in the kids content. We were just asked to do a collaboration with a charity and a pretty notorious popular figure. They've got about 15 million followers on different platforms and things have a pretty good name. And they were interested in doing content, entrepreneurial content, but focused towards children. So they wanted to say, you know, they have these foundations and a lot of they do a lot of stuff around children. They said, we want a safe place. Stephanie Postles (46:58.669) Mm -hmm. Stephanie Postles (47:07.021) Mm -hmm. Jeff Dudan (47:14.35) to be able to send people to, to build so that they're, you know, young people can get entrepreneurial content, but it's going to be, you know, clean and you know, what they would want to see. And so we've got, you know, this on the Homefront podcast here. And I thought, Hey, we can build a whole of a library of content in that way. I mean, it would just, for me, for us, it would be easy because it's the direction the horse is already going. And it would just be getting the right guests on and then making sure that. Stephanie Postles (47:25.453) So good. Mm -hmm. Stephanie Postles (47:40.717) Mm -hmm. Jeff Dudan (47:43.918) the content and which is, you know, my background is in coaching, lots of kid stuff, man, just all about that. So it's very, it's an interest that I have, something that I'm interested in. And I hope we can pull the project together because I think it would be great. And also I think we'd be bringing in a lot of viewers into something like that. So. Stephanie Postles (47:47.245) Mm -hmm. Mm -hmm. Stephanie Postles (48:04.941) Yep. I mean, the market's there. I've looked at the numbers and I see the need and I mean, it depends on the age group, but I mean, that kids project, um, ours is that missionkidsapp .com. And that's where it's showing all the different kids stories that we want to tell. But I mean, depending on the age group, there's really nothing for ages like five to eight or so, which is such an important milestone. And like that time of life is so influential before age seven. Jeff Dudan (48:12.206) Yeah. Jeff Dudan (48:20.974) Yeah. Jeff Dudan (48:28.014) Okay. Stephanie Postles (48:34.349) And so if you have stories that are in a way that kids can understand what the characters that they get to know and love, and you're learning about grit and resiliency and entrepreneurship and long -term thinking and compound interests, I mean, if you're learning about these things through a story, that's what changes the world. Stories are the things that spread through generations. So I love that. Let me know how we can help with that too, because that's something I'm super passionate about. Yeah, for sure. Jeff Dudan (48:40.398) Yeah. Jeff Dudan (49:00.238) All right. Well, all those things. Those are some unpopular topics for kids you just mentioned, but very, very important. Very important. Yeah. Well, take it or leave it. Click away if you must. And the comedy angle, are you a frustrated standup? Stephanie Postles (49:05.293) yep I know. yeah oh well. yeah I know yeah yeah. Stephanie Postles (49:22.477) So this actually comes because so many of my friends, they're just like, Stephanie, you are so ridiculous and funny. And like, why don't you do more of that? And my mind feels like it's a constant circus of like, just immature. That's what she said jokes, even when I'm like talking to executives, I'm like, I need to hold back from the ridiculousness of my mind. And so I started thinking more about this and just thinking of like, man, comedy is one of the highest forms of intelligence, I think, if you know what you're doing. Jeff Dudan (49:50.734) It is. Yeah. Stephanie Postles (49:51.725) Like to me, I mean, I don't know if you've ever seen Joe Rogan, I'm here in Austin. So I saw him and I'm like, he's got a lot of truth in there, a lot of messages and people aren't offended mostly because it's through humor. Same thing with South Park, same thing with Silicon Valley, don't look up, Book of Mormon. Like these all have interesting messages in them. And to me, that's how you spread awareness of things without overly triggering people. You'll still trigger people because... Jeff Dudan (50:12.206) Yes. Stephanie Postles (50:18.829) and many people will get triggered just by you saying hello. So it's not about that, but it allows for a message to spread and the right people will look further into it. And so that's why I think it's a very powerful medium and I really want to get into it. And I just think it'd be fun. Like just, why not? Jeff Dudan (50:21.934) Yeah. Jeff Dudan (50:33.422) Yeah, I've got that eye too and it gets me in trouble because I think everything's funny. Like, I mean, we, yeah, I mean, it's just everything I look at is just like, oh man, I got the joke right away. I mean, but you know, you can't when you're in business, you gotta, you gotta pick your shots. Have you been to the Comedy Mothership? Have you? I'm coming out. That's gonna be, yeah, I haven't picked the date, but I'm just, I'm coming. I gotta be there. I've got a friend who's been, Stephanie Postles (50:38.125) Me too. Me too. Yep. Yep. Stephanie Postles (50:52.269) yeah yep yeah Oh, are you. Jeff Dudan (51:03.31) going out there and hanging out a little bit. So I'm probably gonna hook up with him and go out and do a trip out there, but I'll let you know. Stephanie Postles (51:05.485) Okay. Tell me. Yeah, I'll definitely come. You just have to make sure Joe is actually at the comedy club. Cause a lot of times it's like Joe and friends and then it's just his friends. And I'm like, no, I actually want Joe. Yeah. Okay. Jeff Dudan (51:16.558) Yeah, you know what, that'd be okay. I want to see his club and see what he's built there. I'm sure there'll be good acts and all that kind of stuff. If we can inside scoop and figure out when he's going to be there, that would be great. Well, look, this has been awesome. I really appreciate you coming on. Had so much fun talking to you. I'm so glad we got a chance to meet this year. Stephanie Postles (51:26.029) Yeah, they are. They are. Stephanie Postles (51:40.013) Same. Yeah, me too. Thanks for having me on and yeah, well have to do it on mission daily sometime, by the way, bring you on my show. Jeff Dudan (51:42.542) Yeah, 100%. Last question. Hey, well, look, I wasn't going to ask, but okay, how about next Tuesday? So last question for you, Stephanie, if you had one sentence to speak and make an impact into somebody's life, what would that be? Stephanie Postles (51:49.677) We'll get you bugged. Stephanie Postles (52:05.197) Wow, that's a really big question. Probably that... Let me think about this one. Stephanie Postles (52:17.229) It would probably be. Stephanie Postles (52:22.381) understanding the power of your thoughts and just realizing how your thoughts are creating your reality and how when you start seeing that and you realize that you are a hundred percent responsible, a hundred percent of the time, everything around you is being created by you and your thoughts and your actions and your energy that you're putting towards those thoughts. I think your life can change. And there is one book that I recommend for that as well, that is super old called the game of life and how to play it by Florence Goebel Shin. She wrote this book in 1925 and her concepts are so interesting around this, around what's showing up in your life. And it's like, this is life. How do you actually play this game? It's a mix of spiritual and religion in a way that is grounded. And I actually could get through it because I'm not a super religious person. I didn't grow up in the churches. I didn't, you know, so this was a helpful book to bring it all together. Um, but that's a good one to start that if I were to go back, I would have started reading that because. that would have helped me realize why I ended up at Fannie Mae. Jeff Dudan (53:24.11) Perfectly said and Stephanie, thank you so much for being on. Stephanie Postles (53:29.613) Thanks for having me, Jeff. Jeff Dudan (53:31.278) Yep. This has been Stephanie Postles. I am Jeff Duden, and we have been on the home front. Thanks for listening.

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Brief Summary In this heartfelt and purpose-driven episode, Jeff Dudan sits down with Ben Higgins—former Bachelor, author, and founder of Generous Coffee. From growing up in small-town Indiana to national fame on reality TV, Ben opens up about identity, loneliness, addiction, and the shift from spotlight to service. Now building a for-profit company that funds nonprofits, Ben shares what it really means to live generously and lead a life of impact, not just attention. Key Takeaways Fame isn't a finish line—it’s a fork in the road : After The Bachelor, Ben faced a choice between chasing relevance or building something meaningful. He chose purpose over popularity. Generous Coffee is mission-first : The company donates 10–15% of revenue to nonprofits and builds community through ethically sourced, specialty-grade coffee. Loneliness can be a teacher : Ben’s book Alone in Plain Sight was born from personal pain, addiction, and the realization that vulnerability connects us. Reality TV isn’t reality : Ben shares the pressure to perform, the manufactured drama, and how staying grounded helped him avoid the post-show crash. Purpose-driven entrepreneurship attracts talent : Ben now leads a team of high-capacity leaders who left traditional success behind to create impact-driven businesses. Your story is your superpower : Whether building a brand or healing from brokenness, Ben emphasizes owning your narrative, even the messy chapters. Feat ured Quote “Live every day that you give more than you take.” — Ben Higgins TRANSCRIPT From Bachelor to Business: Ben Higgins' New Mission Jeff Dudan (00:03.961) All right, three, two, one. Welcome everybody to On the Homefront with Jeff Duden. Have a great guest on today, Ben Higgins, who was the bachelor and is now an entrepreneur with Generous Coffee and really has made an incredible splash in our social scenes and on our televisions and now really making an impact with a very purpose -driven business venture. Ben, welcome to On the Homefront. Ben (00:31.36) pumped to be here. Thanks for having me. Jeff Dudan (00:33.081) Oh, right on, man. Right on. So let's dig right into it. Would you mind just sharing a little bit of your background, kind of how you grew up in Indiana? Who is Ben Higgins? Ben (00:44.768) Yeah, definitely. So I grew up in Indiana, northern Indiana, so in a small little town called Warsaw. It's best known really as the orthopedic capital of the world. So it's a super wildly set up town where you have five major headquarters in a town of about 10 ,000 people. And then there's really nothing within 30 minutes outside the town. So you have this really small area of Indiana that has an incredible economy. A lot of really intelligent people, a lot of really good jobs, and then outside of it you have nothing. And so I grew up there. It's a great town. Really love my childhood. I'm an only child. Great parents. And then went to Indiana University in Bloomington for college just as a student. Athletics or huge part of my upbringing, huge part of my life, but after a. A knee injury. I had to kind of refocus and re identify myself, which was a wild journey. And that's what led me to Indiana to to go be the biggest fan of the basketball team because all of the guys that played a you with pretty much went and played basketball Indiana. And so instead of me joining them, I became their biggest fan, which was a humbling experience, a really fun experience. Jeff Dudan (01:59.481) Ah. Ben (02:09.546) But it definitely was a big kind of pivot point in my life and how I viewed myself. Jeff Dudan (02:14.553) Yeah, so I didn't realize it when I saw you on television, but you're like 6 '4", right? Ben (02:18.848) Yeah, yeah, taller. It's it's it's it is weird people nowadays when they when we meet in person like you're taller than I expected. And I said, well, I don't know what you expected. Typically, you know, you go to Hollywood. If I go out to Hollywood still, I'm taller than everybody about about six inches. Yeah. Jeff Dudan (02:20.761) Yeah. Jeff Dudan (02:35.481) Yeah, well, I mean, the Tom Cruise, like the majority of the good actors and they, I think it's just the way they look on. Yeah, man. And they just look good on film in that way. I don't know. I guess, you know, but well, also, what were you like a, were you a shooting guard too? Were you a one, two, three? What would you do? Okay. Ben (02:56.16) I was a three so kind of had to learn to slash shoot a little bit. If I want to go play in college, you know I can't claim I would have gone to play. You but if I want to play in college it was kind of transition for me from being the biggest guy on the floor to now not being the biggest guy on the floor but all but you know. Being a taller three and in Indiana basketball is the thing like you know they say in 49 other states is basketball. That's true. Jeff Dudan (03:07.641) Right. Ben (03:25.984) Like it's in Indiana, basketball is the thing you do. It's the thing that you, if you're good at, you're known for, uh, that people celebrate you for. And for a long period of my life, like I was pretty decent. And so, uh, to have that kind of be taken away or for me to switch from it was a, it was a big shift. Jeff Dudan (03:32.825) Yeah. Jeff Dudan (03:46.041) Yeah. So I was like, I was sick. Basketball was everything to me until I was a junior in high school. I switched over to football because I was, I'm still, I'm about 242 right now, about 62, 42. So that, you know, that, uh, it doesn't work on the basketball. I wasn't going anywhere playing basketball and I was, uh, took three charges, used five fouls, average six points a game. You know, yeah. Oh, you gotta have somebody's got to do the dirty work and let you guys score. Ben (03:57.664) Yeah, it's a salad. Ben (04:10.688) We need those guys. Somebody's gotta do it. Yeah. Jeff Dudan (04:15.673) Yeah, well, cool. So did you do any acting or modeling or in front of camera work growing up? Ben (04:24.608) Goodness, no. Not at all. I mean, I went to Indiana and I left Indiana. In fact, my buddy and I moved to South America, moved to Peru because I didn't have a job offer out of college. No, I didn't know acting, nothing on camera, no television. I then came out to Denver to take my first job because it was the only job offered to me. And I was working in a cubicle in the basement writing user manuals. And so my social scene was very limited. I knew I had no friends in Denver. I moved out here really only because of the job. I had no experience until obviously I showed up in a limo on national television. Jeff Dudan (05:09.101) Tell me a little bit about how that happened. Was that just online? Let me send a picture in and see if I can get on. Did somebody, did mom tell you this is something you should do? Ben (05:19.806) Mobbed and not know it was actually the marketing director of my company. So like I said, I was in this basement. I was at this company. We kind of had an outdated software. We were supporting some clients. I was writing the user manuals and test scripts. I wasn't great at my job. Definitely didn't love my job, but I was working a lot and the marketing director came down. She's very sweet. She said, Hey, I love this show. Um, Jeff Dudan (05:23.831) Oh. Ben (05:47.904) and you're the only person at our company because the company had a pretty old demographic that I know would even be available to be on the show. Yeah, that was not a thing yet. And so she asked if we could go to her office and sign up, like go on the website, sign up. And we did. And then they call and you kind of go through a process. You go through. Jeff Dudan (05:57.881) And the Golden Bachelor was yet to be founded. Ben (06:11.296) obviously the online application, then you go through a video application, and then if you pass it that, then they send you out to LA and you do a psych test and a blood test and more in -person interviews. And then the next step is the show. And so I went through the whole process. It kind of took about six months sent from my application date. And then all of a sudden I got a phone call saying, hey, can you be in LA on this date? And I said, let me check. So I went back to my company and I asked, I didn't want to get fired. So, you know, the risk is you go there, you're there two days, you get sent home, you're jobless now, I didn't have any money, I needed my health insurance. And so my company was nice enough at the time to say, hey, how about we just give you a sabbatical and unpaid leave? You come back whenever you come back. And nobody knew it was gonna be like two and a half, three months off for me to be on the show, but that's what happened. And then I became the bachelor. And so there's another three months off, but I stayed at the job the whole time. kind of would work Monday through Thursday and then they gave me Fridays off to flat to LA and do whatever I needed to do. Jeff Dudan (07:16.057) I've done reality TV, I did the undercover boss thing. So when there was a moment for me where it was this go or no go, and I don't know if you had that or if you knew where you were when you had it, but it's like, you're like, ah, you know, because there's always, especially if you don't come from it and you weren't looking for it, and now all of a sudden, oh man, they're gonna put me through, I'm gonna be on this show. Like. What could go wrong? What's the upside? What's the downside? Did you have any of that hesitation? I had a family at the time. I knew that people were going to look at my kids differently because they had no idea the size of the business that we owned. We didn't, because it was a national, it was interesting because it was a national business. There wasn't that much local presence. So people didn't really know that we had 240 locations out there. And. Ben (07:55.582) Yeah. How an Office Prank Led to Reality TV Fame Jeff Dudan (08:08.109) If this show goes through, they're going to have to go to their school and kids are going to see me giving away $250 ,000 and all this other stuff. So that was it for me. Did you have anything that was holding you back or was it all gas, no brakes for you? Ben (08:23.552) Oh, it was very much holding me back. In fact, once they asked, I took a bunch of time and faith is a very big part of my life. And so I kind of said a prayer at the time, it's the only prayer I knew. I said, hey, if this isn't meant to be close a door, like make that any important door to me, just close it, make it very clear that I, this is not a good step in my life. And so I said that prayer and kind of went out into the world and then I asked my buddies, what do you think? And they said, I think you should do it. Ask my family, my family was like, this sounds wild, but you know, let's spice life up a little bit. Let's create a new story for you that think you should do it. So then the final step was really my job. And like I said, I'd moved out to Denver. I was renting a house at the time. I wasn't making a lot of money. I didn't have much in my bank account and I'm 25 years old and I'm thinking I can't leave my first job, go do this because I don't know what I'd do next. And so I, Went to my, the CEO of the company, it was a smaller company. And I said, hey, here's this opportunity to have, I do want to do it. It is something I think could be fun and exciting and tell a cool story in my life. But I'm not going to do it unless the company here approves it because I can't lose my job and I can't lose my health insurance. And he said, I think this could be good for all of us. And he's like, when you come back, how about you move into sales and get out of user manual writing. being a business analyst. I said, that sounds great. That's what I want to do anyways. And so when he said, go do it, I was like, all these doors have been flown wide open. There was no hurdles. And so then it was kind of all gas. Then it was like, Hey, this is meant to be, this is going to be something. Something's going to come from this. I don't know what, but something good is going to come from this because again, because of my faith and because of the steps I took, I felt like I had crossed all the boxes off and said, okay, you know what? I gave the opportunity for somebody to say no and they never did. Jeff Dudan (10:23.417) What principles or beliefs based on making that decision to walk through that door and to go for it have you incorporated in your life as you continue to make big decisions that could change your trajectory for good or for bad? Ben (10:30.24) Mm -hmm. Ben (10:39.04) Well, I think taking risks is a big one. I think as an entrepreneur, that's about all I do is take risks and try to do my best to alleviate the risks at some level, but then always know that the risks are very much there and there's unexpected things at every turn and every day and every moment. So being more comfortable with risk, I think is one. I think the second piece of that, Jeff Dudan (10:41.145) Mm -hmm. Ben (11:05.248) is it's not easy for me. It was kind of my journey on the show as well was to have confidence in myself a little bit to know that, hey, if I put in the work, if I try to stay a man of integrity, then, you know, maybe good things will happen or at least the bad things will be a little minimized. And so being more confident myself to not change who I am. depending on the situation or change who I am, depending on the environment, but to stay true to who I am and try to be the best version of that in these, in really every moment. And then the final piece I would say that I've taken in is, is to also have the humility and know that nobody knows fully what they're doing and that everybody's kind of building the plane and flying at the same time. And, uh, kind of having some like comfort in that to know, again, there's some ways that I can try to learn and, you know, base my base and decisions on experience, but to know that all of us are kind of in the same spot. We're all trying our best here. Jeff Dudan (12:07.481) Right. Look, nobody knows what you forgot to say. And they can't show anything that you don't say. So if you're disciplined enough about keeping your emotions under control. Ben (12:21.824) Yeah. Jeff Dudan (12:22.169) And you're a little bit thoughtful and you just take a beat. Cause I know like undercover boss men, like they put you under massive stress. Like they're trying to create drama and something's going to go wrong and you fire somebody. Like the worst it can go, the better TV it's going to make. And then you got to have the ones that go great and very emotional. So, so they're pulling you back and forth. And I just, I mean, I would just had to fight them off for like two weeks, man. Just like, I'm not going to say that I'm not, no, that's, no, that's not the way I would handle it. Ben (12:44.832) Yeah. Jeff Dudan (12:48.985) You know, don't you want to go in there and just yell at them? And I was like, no, I don't. But, and then, you know, I think the big thing is nothing is fatal. At the end of the day, like if you die filming the show, it's not, it's because of other life choices and a bad diet. It's not because of the show, right? So, and then we, you know, we had a set of family values. I set my kids down and the last three are fail fast and move forward. Trust yourself to take chances and always do more than is expected. Like that's kind of the last three in our little family crest. And when you look at that, it's like, well, we can say no to this and we can play it safe, or we can look at this as a new adventure, a new opportunity and have this as an inflection point in our life. And if you're going to be true to your values and it's not just talk, then we didn't have a choice. Like we had to push forward with it. And they have to participate. be on the show and all that. So it was very cool. And now for us, and I'm still active in business, so whenever it plays around the world, we get a whole influx of opportunity and brand and exposure and all that kind of stuff. Do you still get, how far is it in your rear view mirror or? Is it something that today with your work with Generous Coffee or other things that you care about, is it a, when is it a big positive for you to have that on your resume, you know, on the big Instagram, like, you know, the big social media accounts don't hurt. Like that doesn't hurt. And then when is it, when is it ever a negative? Faith, Risk, and Saying Yes to the Unknown Ben (14:24.992) Yeah. No. Ben (14:30.944) Um, you know, I think that in a sense, and I'm, it's a loaded question because I think there's a lot of like my story that has to play into answering that. And, you know, you go a couple different directions. You come off the show and it's, you know, you're everywhere and you're getting paid to show up places. You're getting paid to not show up places. You're getting paid to sign stuff. You're, I mean, it's, it's, you know, it's about six months, I would say of just full till, uh, craziness of, you know, being you is the most beneficial financial asset you have. And then it kind of dies off. And once it started to die off for me, you kind of go one of two directions at that point. You either try to stay relevant, meaning you're trying to create new headlines, you're trying to date people, your agents are setting you up on dates with more famous people and they're calling upon the paparazzi to get a picture. or they're wanting you to cause a little chaos in life. And that can be on the front of a headline and people are interested in that chaos. So they wanna hear from you again. And that search for relevancy can be a path that is very lucrative and can really last a long time. The problem is you're consistently working at keeping your name in the headlines. For me, I wasn't good at it. I wasn't good at trying to stay relevant. It was exhausting to me. It felt like it was very much soul sucking for me. It was not when I had a mentor of mine kind of say, hey, Ben, what did you dream of as a kid? Or what were you really good at as a kid that kind of set you apart from everybody else? And maybe that's your dreams now. And so as a kid, it was the creation of things. It was being involved in story. It was being involved in the kind of making things happen. And so me just trying to stay relevant just felt like it was. an empty pursuit that led to great financial gain. So I had to have a come to Jesus moment for me where it was, what do I want to do with all this? And a buddy of mine recommended to me, maybe this is never meant to be about you, what if this is meant to be about something greater than you? And once he said that, my life kind of switched to, okay, I have the social media following, I have the platform, I still have name recognition, but I don't want to build brands based on me. Ben (16:54.944) So can I build brands that could even outlast me? Could I build brands or businesses or could I get involved in things that are not about how famous I stay but still allow me maybe the financial freedom, the personal freedom, but also allows me to stay very actively engaged and involved in these things and then, hey, you know, God forbid something happens to me where I'm no longer on this earth, right? The brand still continues or maybe I do something super stupid. Jeff Dudan (17:20.057) Thank you. Ben (17:21.92) You know, wake up one morning, I say, I'm going to cause a lot of chaos in life and a bad headline comes out, right? And I get pushed aside by society. Well, the brand maybe can still continue, right? They can still pick their feet back up, build up and continue. And so that was kind of my trajectory. So to answer your first question, it's always been a benefit to me. There's been moments where I definitely could see where it would have been a hard, but since that kind of. Jeff Dudan (17:33.559) Yeah. Ben (17:48.992) pivot point to where it's no longer about me. I no longer feel the pressure to use the bachelor necessarily for my own gain. But oftentimes it's just kind of if people know about the show, if they've seen the show and I'm on a call trying to, you know, close a deal and they're like, Hey, you were on that show. Typically, I've never had a moment where it hasn't happened. They're like, that's cool. Tell us more about it. It builds a different relationship. They feel like they know me and and good things come from it. So for me, I've never been resentful towards the show. I also had a pretty good ride on the show, right? The show was pretty good to me overall. And I don't necessarily even know how I can answer like why that was. Maybe because I didn't try to say stupid stuff and cause fights and get myself into trouble. But, but no, overall, it's been a really good experience for me, one that I'm very grateful for. And icing on the cake was that my wife responded to my direct message on Instagram. Jeff Dudan (18:35.001) Yeah. Ben (18:47.968) because I had a blue check mark and I know she was getting hit up a lot on Instagram by people. I just stood out maybe because I'd been vetted a little bit by social media. Jeff Dudan (19:01.177) Really a huge compliment to you because I'm older, I'm more senior in my career. Although I was thinking I was in the fourth quarter and I've reset back to halftime now. I actually just, I'm having so much fun now. Dude, I turned 56 like in 30, in May. And, but I don't know, man. I've never, last kids out of the house, I've never felt more purposeful. Ben (19:12.544) Oh, let's go. Jeff Dudan (19:27.033) and had more ability to be more purposeful and also having more perspective and resources to be able to be even deeper into my purpose. And, but for somebody your age to say, you know what, I've got, I've got this going because it's exactly what you said. I really hadn't connected the dots, but when people are, or they get notoriety, next thing you know, they start showing up everywhere and all this click baits and they're popping up and all of a sudden it's like, I'm like, oh wow, those famous people, they must all date each other. I didn't know that people were setting you up to, you know, to, cause everybody's furthering their career to see who's dating who and who's, you know, your brands gaping and swapping audiences and all of that. Okay. Well, that's all fair. That makes sense. That's the world we live in. But, Post-Fame Burnout and the Pressure to Stay Relevant Ben (20:00.224) Yeah. Ben (20:11.168) Yeah, I'm not, and I don't say any of that, say that path is bad necessarily. It's business. It's, you know, I think for me, it just, it exhausted me at a level. I couldn't continue it, you know, but some can do it. And those people are very impressive to me, but you know, different strokes. Jeff Dudan (20:14.477) No, no, it's business. It's just business. Jeff Dudan (20:33.433) Yeah, well, so like, here's the deal, man. Our will is an exhaustible resource. So you only have so much every day. And then we all have a personality profile, who we are. And then there's another personality profile, who we need to be at work or in public in this case. Depending on the size of your battery, you can only be somebody you're not for so long until it just starts to wear you down. And you said it was exhausting, right? To try to... keep all this stuff straight. Well, it just wasn't who you were. And you very early in your life came to a place where you see a lot of other celebrities do this much later in their life as they decide, you know what, I'm going to use what I've got for good. And I'm actually going to go into, you see it with clothing companies and all kinds of business stuff. So, but the fact that you came to it so early and, uh, you know, it was really, it was really impressive, uh, really impressive. So. At some point you decided to write a book and I heard you on a podcast as I was preparing to talk to you today that you said it took you a couple of years to get done. Which means you, which means you wrote it yourself. I think. Yeah. I mean, like we all have editors and ghosts. You can dictate stuff and there's all kinds of services out there, but. Ben (21:34.56) Mm -hmm. Ben (21:46.464) Yeah, for the most part. For the most part. Jeff Dudan (21:54.361) They would have kicked you the curb long before two years. They would have got you. They would have got you done in 90 days. But so what what motivated you to write it alone in plain sight? Ben (21:57.182) Yeah. Ben (22:06.912) You know, I kind of going back to, I think I had a self -fulfilling story. As a kid, I felt very, for a period of my life, like as a little kid, I felt very much like the outsider looking into life. Kind of felt like nobody understood me. I didn't really understand others. You know, I'm an only child, so I spent a lot of time around adults and around my parents. Went into school. uh, had a kind of a weird time trying to make friends and, but really desired friends and really desired like that, those relationships. And so then I, you know, obviously I talked about sports a little bit, which is, you know, some people dismiss it because it was in high school. But for me, sports was such a huge part of my life. It was also a huge part of how I made friendships and how I made connections and what I was known for. So then I got her tore my knee all up, had to kind of switch what I was going to be in life at that point or at least in the, you know, for the next chapter of life and got incredibly down on myself and ended up forming an addiction to opioids because I was on painkillers for prescribed painkillers for six, you know, six months straight. And so then I never really got out of it for four years. Kind of came out of that and felt more lonely than ever because I felt like I had pretty much pushed aside every good relationship in my life. I really didn't know who I was as a man. I didn't know who I was to others. And that's when the book really started. And so I hadn't started writing it, but I had this notebook that I had all these feelings and quotes of mine in, that I would sit at my little desk in college and write down all these thoughts going through my head. So obviously the show happens, Bachelor happens about five years later for me. and come off the show. And on the show, I had this moment where I was in the bachelor at the time. And one of the producers came up to me one day and he says, I don't like you. And that's like the one thing you could say to me that would like make me feel as small as possible is I don't like you because you don't let me get to know you. You say the right things, the right moments, and then you hide when moments get hard. And he goes, you've been here how many weeks and I don't know anything about you. And it was always kind of my thing. Ben (24:31.456) Right? Like I always kind of desired to know others better than maybe I even knew myself or how I would ever let them get to know me. Because my fear was that the more they got to know me, the less they would like me. And we, you know, that could be five hours of us unpacking how that kind of build up. But that was my general consensus is the more people got to know me, the less they would like me. And so I admitted this on national television. I said at the time I felt unlovable. I kind of have re Assessed and said I think I was meaning I felt more unlikable. I felt like it was really hard to like me which would be hard than to love me and I say this on television get off the show and the response was crazy. I've never had anything in my life even today where more people have reached out said I feel the same way. And so that's when the book started from that moment on so started writing it started telling my story. Jeff Dudan (25:06.393) That's fair. Ben (25:28.544) And then I started telling the stories of others, some people in my life that I've ran into who maybe had every excuse to feel like outsiders, yet they had chosen not to, or they had some good tips on how to keep grounded. And so, yeah, it took a long time. A lot of it took a long time because I was kind of unwilling for a while to admit and write some of the stories in the book that I thought could really be, this were just were hard for me. to vocalize or ones I had kind of forgotten because I pushed them so far down in myself. And so two years later it came out. It's about connection. It's about loneliness. My hope is that people read it and they feel less alone after reading it. The problem with all this was, and it wasn't planned this way, it came out right in the heart of COVID. So all the good book tour plans and all the good activities to help people get connected again weren't happening. But at the same time, it was kind of a good time for the book to come out because a lot of people were feeling lonely. Writing Alone in Plain Sight: Addiction, Identity, and Connection Jeff Dudan (26:32.345) Yeah, that's fair. You've mentioned several times that you've got some somebody shared some experience with you, gave you some advice. Is there one or two people in your life other than a family member who you would point to and say they've had a huge impact speaking into your life? Ben (26:51.968) You know, a lot of people come to mind like when you say that, but I was at a leadership summit in college and the guy that was speaking got up on stage and he said these words that really stuck with me. He said one of the best lessons he learned later in life. And anytime you say, hey, you know, as a 22 year kid and there's somebody up there who's 60 years old and they're saying, hey, this is something I wish I would have learned at 22. I'm, I'm listening. I'm in like, all right, tell me, tell me what's going on. And he said, I wish I would have been willing to learn from anybody. And so I've taken that with me is just to be very willing to learn from anybody. I'm going to agree with everything I'm hearing. But if you're speaking from a place of your story has led you to this belief, you know, be it politically, religiously, from business, personally, family, whatever the big topics of why you hold on to your strong convictions. If you're telling me that this is where life has led you to believe, I want to hear what you're saying. and I want to understand how you got there. And so maybe not, maybe people, like there's some people that I would lean on maybe more consistently than others, but over the last, you know, 10 years of life, it's really just kind of having a listening ear and being open to hear what, you know, what others are saying. Jeff Dudan (28:11.353) My best advice is to don't take advice and don't give advice, but look for shared experiences. Because some of the times when I've made decisions that I tried to inform with other people, they gave me their advice, but they really didn't have experience in it. And I'm in a group called YPO, which is Young Presidents Organization. And I learned that late in... Oh yeah? Yeah. Ben (28:33.184) My father -in -law's in it. Yeah. Jeff Dudan (28:36.569) It's a great room. It's a great room to be in, but they, that's it. If you don't have an experience to share, whether you're in forum or whether you're in one of the meetings is like, don't say it just because it's not your job to spit ball other people's problems on something that you have no experience with. Uh, so it's, it's interesting, but it's very subtle. Uh, but now when I'm, I have mentors and people that I look up to and. I'm fortunate to be able to get in a lot of different rooms and I really seek other people's, I even ask specifically, like have you had experience or what's been your experience with that? And so for the 60 year old to share his experience, I guess he, it's different man, advice and experience, like they're cousins, they're close, but. Ben (29:24.64) Yeah. Well, they kind of build off of each other in a lot of ways, but I'm with you. And another thing that's kind of been fun for me is I look for people who've experienced, kind of gone through the valley of the shadow of death, like gone through it, because those people are the ones when they come out the other side, they just have a whole different world. And it's also been really, in June of three years ago, I went through a really weird, very kind of like solemn state. I just noticed, hey, I'm not who I am. I was engaged to my fiance at the time. I was like, I'm not who I want to be. I just feel super down. I have a thousand questions. I have a thousand concerns about what kind of husband I can be, what this marriage thing even is, where my career is going, how I'm even going to help support our family alongside of her. And I just kind of went through it. And I... actually kind of left Denver went back to Indiana where a place I was familiar with. I sat on the lake for about a month and a half and all of a sudden it kind of hit me. It was like, you know, you're going through it right now and you're going to this mental kind of like note in my head, like you're going to make it through this and you're going to learn a lot during this season. Like this is not you losing yourself. This is not you being less than. And here's the thing. Four years ago or four years before that. when I would have went through, I would have beat myself up so bad about how can you be this type of guy? Like how can you have these types of questions? How can you be so down? Life's so good. Like instead I was like, no, you're learning something here. Be willing to learn it. And when you come out the other side, you're gonna be able to speak with and to people based on this experience and probably relate with them in a way you wouldn't have unless you had this time. And it gave me this whole new like purpose, this whole new mission. Ben (31:19.104) And I actually came out of the other side, I think healthier than ever. I don't know if I'll go through it again. I might, you know what, life's weird, who knows, but it gives me this whole new kind of like perspective on when you go through your times of trials, the benefits then of what you're gaining on the other side. Jeff Dudan (31:35.385) Yeah. Look, man, your ability to self -correct is noteworthy. So like negative progress is the greatest dissatisfactor in life. Nobody likes to be worse off than they were. That's why child actors and celebrities who you've been it like even my little bit on the show. You were the star. Everybody's taking care of you. They're taking you to the trailer. They're putting your makeup. They're doing all this stuff. I mean, imagine if you're a child actor for 10 years and you're living in this fantasy land of everybody's just taking care of you. doing everything for you, everybody wants to be around you, you grow up in that. And then when that goes away, like people really struggle to make that transition because it feels like negative progress. So, you know, you blow up on the bachelor, you've got all this great stuff going on, it goes on for years, they bring you back, you're one of the most popular ones. Ben (32:16.896) Mm -hmm. Jeff Dudan (32:26.777) It's some, you know, you transition into a different life and a different, a different season in your life. And there's going to be the bends, you know, it's just, it's going to happen because most people make the mistake of thinking that the trend line always goes up into the right. And, you know, they just keep going. I mean, you know, why do people make a hundred million dollars and then they spend the rest of their life killing themselves trying to make 500 million. It's because they've got a. You know, they you can't self everybody's just got to keep climbing for that next that next mountaintop, which is fine, but done incorrectly. It'll kill you. I mean, it'll just it'll it'll like, oh, I, you know, I'm going backwards now and and which isn't generally true, but definitely you can feel that way. Well, very cool. Man, I'd love to. spend the rest of our time on Generous Coffee. I've been on the website. It's a purpose -based organization where profits are, it's a for -profit company that gives your profits to nonprofits. And I don't know the percentages or anything like that, but like that's the concept of it all. How did you first get involved with the coffee business? Ben (33:45.024) Well, it's actually interesting on base on what you're just saying about, you know, the trajectory up into the right. And like, what exactly does does that look like? I think there's some great ways that. We've tried to quantify what success looks like, and there is some very, you know, distinct ways, right? But some of the coolest people in my life are Franciscan monks who have never, you know, really made a dime and they're wise and they're peaceful and they're joy filled and they have a ton of time for others and they have crazy cool stories like, you know, There's a lot of markers of success is my point here. Generous Coffee: Building a Brand That Outlives You Jeff Dudan (34:17.337) Yeah, and they're 100 % good with it, probably better with it. Yes. Ben (34:20.736) They're content with it. They're happy. They're in it. So the story goes like this. So when I was 15 years old, I went to Central America for the first time with my local church and I saw deep seated poverty. So like, and this poverty was mostly coming from some type of corruption or injustice placed on these communities all around Central America. And so with this organization that I went with, It was me and a few of my buddies with our families. We went, we did this thing where we go into these communities and we passed out food boxes. We told people to come to church with us. Again, I want to say, you know, faith is a big part of my life. Church is a big part of my life. I'm very much in favor of healthy, good church relationships. So this, you know, comes with that dynamic. But we would say, here's a food box. You get this food box if you come to church tonight. Then they would come to church and we'd do this whole thing. And then next year we went back. The following year we went back to the same communities. and they were still very thirsty, very hungry. They didn't have jobs. They didn't have education. They didn't have any better infrastructure. Uh, and we did the same practice and I got pissed. I left and I was fired up. Uh, and I didn't know why I was like 16 years old. I couldn't really conceptualize why I was so mad, but I was like, this feels, uh, one, I feel a ton of guilt that I'm going back to my home to, um, I feel like what we just did was very purposeless. And I took a bunch of pictures with some poor people and came back home to tell my friends how, how cool I am, that feels very weird to me. And so I lived about three years of my life in this just like anger at a lot of things. And I didn't know it was like a righteous anger at the time. I thought I was really like losing myself in this. And finally, one day my buddy comes to me and he goes, hey, I know you've been mad about this for three years. You've been very outspoken about this. I got this idea. Jeff Dudan (35:48.857) Right. Right. Ben (36:14.4) What if instead of this transactional relationship with these people who've been hurting by injustice is placed on them. What if we go into these communities and we ask them, what do you need? What do you want? What do you dream of? And how can we help? And we let them guide us. So we come back to the US where obviously fundraising is a little easier. We can get some support, some rallies, some networks around us. Go back in and do it. let them lead us on, hey, if they want jobs for women, let's figure out what jobs their women can do and let's help them build these businesses. Or if they want clean water, let's help them pay for a clean water tank, right? But they're owning this thing. And we started the organization and it's awesome. I mean, it still exists today. It's great. It's not like super unfamiliar to new modern age missions work. Like the 80s, 90s, 2000s kind of like transactional come, do this and get saved kind of idea is no longer as popular as it was back then. So this whole kind of partnership idea is now common. People aren't shocked by this anymore. But it was new back then. The problem was we were all in our 20s and resources for donations were limited. We could only tap into our parents, grandparents and friends so often and our friends are all poor. So like Jeff Dudan (37:29.241) Yeah, and you gotta save them to sell them the Cutco knives. Ben (37:32.16) Yeah, exactly. Exactly. So we so went on the show, kind of fast forward, still involved in the organization, ended up joined the board of another nonprofit called Project Hope. Project Hope is one of the top 10 largest nonprofits right now in the U .S. So it's huge. So I'm on this dynamic where I'm on the board of a organization fighting to stay alive. And another one that's, you know, blessing endowments and doing massive, massive medical like hospitals. And so I came back, kind of had that moment where I talked about where I was like, this thing has to be for, I have to do something greater than myself, something that's not built on me. What if we started a business because I love business. I don't want to lose. I don't want to lose my touch on skill sets that, you know, helped me stay involved in business because I don't know how long this bachelor thing is going to go or how long my fame is going to pay for pay for me. So what if we start a business that's for profit? Uh, the executive team and the ownerships agree to never be repaid from it, to never take a salary from it. And then we donate 100 % of our profits to nonprofits so that we can become a sustainable fundraising source for those organizations that are doing great work, but just having a hard time figuring out where to tap into. And... So I said it, you know, to kind of go on what you're just saying. One of the cool things I found when we started generous. So to date we donated close to $200 ,000. We're sit seven years in. We're trying to grow our business. We're about 70 % wholesale kind of promo corporate gifting wholesale accounts and 30 % retail. But one of the cool things we found was as I, as we launched generous and I kind of ran it myself for two years, then all of a sudden we had these people. Like my co -owner now who was 30 years old the CEO of this huge insurance crop insurance company and He kind of goes at 40. He's like I'm kind of done. I don't know what to do next Right, but he's financially set perfect person right comes into generous whole new You know complex business to try to figure out and run but the benefits for him are not financial what they are is story and impact Ben (39:54.684) And the benefits of this is beautiful for him because he lived a lot of his life saying, I just need to make the next hundred million. I need to make the next hundred million. And all of a sudden that wasn't working for him anymore. And he didn't know where to turn. So now he turns to generous and he says, let's let's rock and roll here. Like, let's build something that is is creates a better story. So we're able to donate anywhere between 10 and 15 percent of our revenue. So outside of, you know, once we pay for everything else. larger volume years we can get to 15 % lower volume years we haven't dipped below 10 % yet. That's the numbers, the percentages of what is actually being able to be given. Jeff Dudan (40:33.145) And is it mostly online sales? Ben (40:35.904) Yeah, yeah, mostly online. I mean, we have some boutiques and like some some smaller box stores that sell generous. The problem with us is because of our donation model, we can't really get into the large retailers because of the margins that are already cut. But, you know, those smaller like local towns and homes and then are, you know, really here over the last year and a half, it has been more of the branded merch. Jeff Dudan (40:49.657) Right. How the Coffee Model Works: Profits, Partnerships, and Purpose Ben (41:02.752) partnerships that have really helped us, you know, take the next step. Jeff Dudan (41:06.553) Nice. And where's the roastery and where do you get the beans? Ben (41:10.656) We get the beans from all over. So that we're specialty grade coffee. So we get smaller lot coffee. So this coffee will be from anywhere from Africa to Mexico, South America, Central America, all over for beans. And then we roast in War Sandia in my hometown. In fact, in May, we have a building right now that's never been open to the public. So we bought this old warehouse, put a roaster in there. We have some offices from some of our employees. And. Jeff Dudan (41:19.257) Okay. Ben (41:38.496) We've always package shipped, done everything out of there. Well, we just bought a new building that will open in May that's going to be open to the public. It's going to have a little counseling center in there. It's going to have a place where people can hang out and, you know, drink coffee, not necessarily a coffee shop, but just more of a chill area where you can work from there. And then we'll roast in the back. And it's a super cool 1890s building that we've renovated over the last six months that I hope because. just becomes this kind of like really proud moment for the small community. And then also just a really good like kind of location for people to gather and connect. Jeff Dudan (42:16.313) My mind is going crazy with partnership opportunities for this business. And I know I have a friend who has a pretty big addiction related charity and I know they do lots of things and you know. Fundraisers things for people to do things for people to sell things for people to package. I don't know. I don't know where you are. I was on the website. I saw you had a lot of partners partnerships and affiliations, but I really wasn't able to discern what each one did or what they meant. Uh, have you explored that with generous to say, Hey, let's, let's partner up with another, you know, maybe a nonprofit and then be able to further the brand and further the agenda that way. Ben (42:57.6) Yeah, so just for anybody listening out there that maybe is curious about how they could work with generous if you're interested, I would love to kind of explain how we're set up. So right now our partnerships come through a program that we call highlight hope. So if you get on our website, you'll see these highlight hope bags, which is probably what you're talking about. And every quarter we pick four new nonprofits and these nonprofits then design their own bag. So these these bags that you'll see. are designed by the nonprofit. It tells their story on the back. There's a QR code at the bottom that links to their website. And then it's our retail back. So it's what you would buy if you got on a website and subscribe to Generous Coffee. If you went to a store and bought Generous Coffee, these would be the bags that Generous are selling right now that we're known for. And then when you buy a bag, you're kind of voting with your dollar. And so you can just to be, you know, Uh, conservative here, you could know that 10 % of your purchase of that bag is going to go directly to the nonprofit that you chose. So you can choose what nonprofit you want. So it's kind of, you know, if a nonprofit sells a hundred thousand bags of coffee in that quarter, well, that's a lot of money going their way, right? If they only sell 25, 500 bags of coffee that quarter, not as much money going their way, but they get to kind of use that then for their fundraising. They get to go out and buy it at wholesale and go resell it, you know, in their shops or whatever with corporations. Um, Jeff Dudan (44:06.169) Sure. Ben (44:20.512) It's really cool. So like we just did a program with Capital One, where Capital One put us in their headquarters for a month's period of time. And then one of their employees actually helped is helping run this organization out of Haiti that you would see in our highlight hope campaign. And they bought this coffee and then we designed kind of a storytelling around it. It was like, hey, buy the purchase of Capital One. This money is going to be going to this organization. And so there's some employee engagement in there. And there's also some employee satisfaction where like my company cares about getting back even down to the, you know, cup of coffee we drink. And then also finally we do co -labeling and white labeling. So if like, uh, you'd see on our website right now, like Brian Peterson, realty out of Warsaw, right? Every time somebody buys a new house, he has his own bag. Generous isn't even mentioned on it. We package, we ship it. He gives it to his new, uh, purchasers. Jeff Dudan (45:13.401) Nice. Ben (45:16.512) But then on the back end, there's still money being donated because he's buying the coffee from us. So there's a bunch of different ways that we try to give back and that we partner with nonprofits to try to highlight what they're doing. We've just found it more successful recently to do it through maybe the more for -profit space where for -profit businesses or churches are saying, hey, we're serving 3 ,000 cups of coffee a day. Might as well buy your coffee. Then we can give it to this organization. Jeff Dudan (45:39.257) That's right. Yeah. Sustainability, packaging and all of that. When I looked on the website, stuff looks sustainable. Obviously the branding is done extremely well. Is that also part of it or is it just, I mean, is there any sustainable options? And here's the reason I ask. So my daughter's got an internship with a big firm in New York, one of the biggest. accounting, investment, consulting, whatever. And they have a Starbucks in their space in New York that's free to the employees. Okay, well, what if that were a generous coffee thing? And that's more work, it's outside the model, somebody's gotta pay for all that. But companies have these sustainability goals. And certainly from the optics perspective. You know, so I mean, you know, that's that's logistics. That's all of that. I mean, Starbucks does a really nice job with, you know, they they I think they're going to be very successful one day. Let me just put it that way. But one day they'll they'll finally get it right as I as I sit here with my my Trenta that I'm pouring into my speakable future mug. But. Impact Over Optics: Focusing on People, Not Packaging Ben (46:50.208) One day they're going to figure it out. Ben (46:58.688) Yeah. Jeff Dudan (47:03.361) Now, just because my New Year's resolution was two cups of coffee a day. So that's one. I only count that as one. I was like 20, dude. So now I get 230 ounces. Ben (47:08.64) is yet up or down from where you were at. of this. You need to be generous. You'd be our biggest purchaser at this point. Yeah, we you know, we're actually we're doing this really cool thing right now. We're doing them in high schools. So we're launching coffee shops, cafes and high schools where the students are going to run this business. We're going to provide them, obviously, with the stuff they need, but then they get to kind of do this, run the shop, figure out the books. Jeff Dudan (47:16.857) Well, I'm going to as soon as I get, oh jeez. Yeah. Jeff Dudan (47:31.905) Okay. Ben (47:42.048) pay their teams, order all their essentials, make sure their quality is good. I think it's, I actually, I didn't even think about this five years ago, but this is one of the coolest things to me is the idea that in high school I could have been working and running my own business and learning that whole thing. I think it's such an incredible education. I think it also is gonna get so many unique people really fired up about going to school. Jeff Dudan (48:00.185) Right. Ben (48:11.68) Like, oh, I got to show up to school, you know, an hour early today because I got a package, you know, this coffee because it's going out to our teachers. Coffee shops are hard. We've entered into a few of them. I would love to get back into them given the right circumstance. You asked about sustainability. There is sustainability options. So like our brown bags obviously are recyclable. Our bags right now that we saw on retail aren't exactly. Probably I couldn't brag and be like, yes, these are the. Jeff Dudan (48:13.975) Yeah. Ben (48:41.504) the healthiest thing for the environment. But one of the interesting pieces to generous that, you we get asked and I hope more and more from other for -profit businesses, kind of how did you design your give back model or, hey, we have this ESG program in our business and these are our goals. Can generous fit in to help us meet some of those or how would you speak into some of these? I always, my only, my number one, not my only advice, my biggest advice is to pick a lane. Jeff Dudan (48:57.559) Mm -hmm. Jeff Dudan (49:03.321) That's right. Ben (49:10.528) And so our lane is humans. It's what broke my heart first. It's what breaks our team's heart. Like when humans are facing injustice, be whatever that is, right? If it's human trafficking, if it's poverty, if it's lack of things, that's what our team fired up about. And so we've chosen humans as our lane. We love animals. We love the environment. My dog's laying at my feet right now. But we're solely focused on what can we do as a business right now with our capacity. to give as much back to the humans who need it. And then, you know, with scale with kind of greater visions with more resources, I'm excited to always look into the future. But right now we're still a small business and we're still trying to do what we can to make ourselves sustainable so that we can, you know, grow into the future. The Future of Generous: Schools, Storytelling, and Shared Impact Jeff Dudan (50:00.633) Well, well done. Great future for Generous Coffee. Love the brand, love the name. You know, I'm a franchise guy, like that's what I do. So, you know, I'm thinking, well, how can I put a double -sided driveway around a little thing? But, you know, I don't think franchise owners would give away all their profit. I think it would be a, you know, if I can connect that dot, man, I'll call you back. But I don't know, we, we, uh. Ben (50:05.28) Thank you. Ben (50:12.576) Do it. I'd love to. That's a tough sell. It's a tough sell. Ben (50:25.792) But if there's anybody out there listening that you know is has their own business or you know wants to do is for gifting or to provide in their offices like I would be not doing my job well if I said please don't reach out to generous I would love to figure out great ways to do it because that's what we're about and it's been fun for us so yeah anybody's interested let me know. GenerousCoffee .com Jeff Dudan (50:34.745) Yeah. Jeff Dudan (50:51.971) All right. Generouscoffee .com. Ben, last question. If you had one sentence to speak into, speak your experience into somebody else's life, what would that be? Final Message from Ben Higgins: A Life of Generosity Ben (51:07.162) Live every day that you give more than you take. Jeff Dudan (51:11.449) I love it. Perfectly said. We'll end on that. How can people get in touch with you other than GenerousCoffee .com? Where would you direct them to get your attention and connect with you? Ben (51:24.24) Higgins .Ben on Instagram is where I stayed most active. And then I do have a website that updates kind of what I'm up to or speaking engagements. It's a very narcissistic website called TheBenHiggins .com because BenHiggins .com was taken. So it's TheBenHiggins .com and you can kind of get updates on business life or kind of what's going on through that too. Jeff Dudan (51:48.057) Yeah, I actually own benhiggins .com. I squat on domains. So if you'd like it, we can talk after the show. But anyway, hey man, Ben, it's been incredible to have you on. Really appreciate your perspective. Enjoyed the conversation very much. All right, and this has been the Homefront with Jeff Duden. We've had Ben Higgins on here. And thanks, everybody, for listening. Ben (51:49.984) Yeah, I'm gonna check about. Ben (51:55.136) Appreciate it, man. Ben (52:03.104) Hey, thanks for having me. This was great. Ben (52:13.344) Jeff.