Great Entrepreneurs Learn When To Pivot with Alan Ezeir

Nobody can predict the next wave that rewrites business, but we can get better at spotting signals, choosing partners, and selling something people truly want. We sit down with Alan, a lifelong entrepreneur and investor whose journey runs from UCLA side hustles to telecom, domain names, and backing founders across industries. His stories are candid, specific, and full of lessons you only earn through repetition, risk, and recovery.

For decision-makers dealing with uncertainty—and for any founder who’s ever felt alone in tough calls about pivots, partnerships, or timing—Alan brings a deeply question-driven approach to entrepreneurship. What problem is real enough that people will pay to solve it? What signal matters versus noise? And are you adapting because the market changed, or because fear did?

We dig into why sales is the first job of every founder, why distribution is often the real moat, and how to build resilience without sliding into stubbornness. Alan shares what he looks for when investing: timing validation, repeated behavioral patterns, and the character traits that predict who stays standing when markets turn. It’s a form of peer-powered disruption—surrounding yourself with people who sharpen judgment, challenge blind spots, and help you avoid building in isolation.

The conversation also explores co-founder fit, “manufacturing serendipity,” and the difference between chasing every opportunity and committing to the right pivot. Sometimes growth means deciding what’s not your problem so energy stays focused where momentum actually exists. Other times it means learning to run toward the roar when the data is incomplete but the opportunity is real.

Then we go deeper on the human side of leadership: fear, anxiety, ego, trust, and the subtle ways money can make businesses worse by lowering urgency and dulling creativity. We close with a grounded take on AI in business: don’t worship it, don’t ignore it, and demand real ROI before calling it transformation.

For anyone ready to challenge their comfort zone around entrepreneurship, investing, and leadership under uncertainty, this conversation will sharpen your instincts without pretending there are easy answers.

Real leaders. Real stories. Real action.
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Transcript

Cold Open On Timing And Resilience

Alan Ezeir 0:00

No one can predict it. You know, no one could have predicted the iPhone and O seven would have changed everything, but we were all kind of like, hmm, this is an interesting device. And now we look back and say probably one of the biggest changes we had in our generation in what happened in industry. People's ability to be resilient. So I think uh not every entrepreneur is created equal. And resilience with some common sense a little bit, like uh not a haphazard resilience where you just you'll do it until the dying end. And I've watched many entrepreneurs do that end up with uh a half a percent of their company. And all right, that wasn't the smart way to do it, but doing it with resilience and and picking the right people. So in my seat, I'm like, is that the right person that's gonna go through the war and is gonna do the hard things? And are they recognizing timing? And there's a little bit of luck in timing. So um I I I do believe what people get caught up in is, and no one ever should get caught up in this, is falling in love with the product or service.

Mike Maddock 1:00

Welcome to the Your Seat at the Table podcast with your hosts, idea monkey Mike Mattock, and ringleader John Tobin. We're two founders, a serial entrepreneur and a billion-dollar operator who talk to leaders about how, when, and why they made their most pivotal decisions in life. Join us as we share wisdom, mistakes, and a few laughs learning from the brightest minds in business today. Okay, lucky us. We have uh my friend Alan with us today. And Alan is here is uh, let's see, Brian Wish, our mutual buddy, put us together. See if I get this right. You are the founder of Circle Swear Cap. You are the founder, I believe, of Sipping Life Tequila. I want to talk about that. One of my favorite drinks, founder of Crypto Portfolio, founding member of uh a fellow founding member of a YPO chapter. Both of us got to do that, which is fun. Um so you are an entrepreneur that is now investing in yourself and investing in a lot of other businesses. So I'm keen to understand uh what wisdom you have after seeing so many businesses succeed and fail. But before we get to that, thanks for coming and give us a little story about how you went from I think you started in domain registration. Yeah. How'd you how'd you start and how'd you get here?

UCLA Hustles And Early Lessons

Alan Ezeir 2:30

Well, appreciate it, Mike. Thank you for having me on. I think um when I think of where it all started, I go back to college where I didn't feel like I fit in, but I found my people there in an entrepreneurial group called the Southern California Entrepreneurship Academy. And it was very, this is like uh late 80s. And um I realized I just wanted to uh uh transact in business, you know, buy something for one price, sell it for another, add value, and did a lot of things on the campus of UCLA, um, where I was selling t-shirts, selling computer services, uh, got involved in uh promoting uh spring break trips. Uh, and I was the one that would get up at five in the morning, and back then you would actually post flyers on billboards, you know, it's like uh we we or or on kiosks. So I think it all started then, and I wanted to graduate. And uh ironically, UCLA did not have a undergrad business school. They have a graduate business school, and I wasn't gonna stay in school uh for that much longer. And that's when my entrepreneurial journey began and thanked my parents for not putting me in debt and said I'm we're not gonna get a job. And that was uh a moment where my dad was like, What are you doing? And my mom's like, I'll I'll I'll uh support you any way I can. Uh and that's when it all started.

Mike Maddock 3:59

Um, many go ahead, Mike. Yeah, so yeah, I it seems like it started before that because you're already making your own money. And yeah, I do you think that um if I had to pick one seat for an entrepreneur to start with, it would be the rainmaker seat because you have to have sales to have a business. Yeah. Do you agree? I mean, like you the rest you can figure out as long as you have cash flow and sales. Is that your would that be the first horse you'd pick? A hundred percent.

Alan Ezeir 4:33

I I I think people forget that. And there is cases that that's not the case, but it's very um it's not as often, right? I can I can name a couple ideas that are like, oh, it didn't have to be a salesperson, but you came up with something that was like too easy to sell or the timing or whatever it is. But in the end, I think I ask everyone go find something that you can make, buy, and then enhance it and sell it for more. You know, it's or find a distribution channel that didn't find that thing that you made or bought and sell it. I mean, in the end, one of some of my mentors would say when we when I was in the stage of buying companies, he's like, look at their distribution closely. Because if it's hard to create that distribution, that's the asset. The product and services are what move across the table because there's a demand. But what's really the moat, what's creating the why do they exist? And uh, whether you're starting a business or buying a business, you have to see those things. But I agree with you. The first seed an entrepreneur needs to do is feel comfortable with taking something that they made or bought and selling it to somebody that needs it.

Sales First And Distribution Moats

Mike Maddock 5:50

You know, it's interesting you should mention distribution and have a tequila business because what it reminds me of is we took on Old Style, which is an old beer brand years ago, and then I started uh an investment fund, which was a complete disaster, by the way. I had no right being in the investment business. Um, but that's we don't have to do that. The failures are good. Some don't, yeah. Yeah, the failures are good. We we looked at a few alcohol brands, and what I learned from uh startups, what I learned from old style was distribution is everything, and it is so hard to crack that code. So, but let's let's not go there. We'll we'll get you so you you get out of school, yeah, and what happened?

Alan Ezeir 6:37

Yeah, and then and look, I I'll skip over the probably half a dozen businesses I started, but one of them was critical because it taught me that I really loved what I was doing, which was I had a t-shirt business, which a lot of kids in school end up by having a t-shirt business, but I had a distribution with small rock bands in Hollywood. I grew up in Los Angeles, and I would make 144 t-shirts from for them. I'd make a couple bucks a t-shirt, maybe I'd make $300 a sale, and one of my bands got signed, or one of the bands that I was working with get signed. They need 5,000 shirts delivered to Canada where they're playing in a show, and I'm making $3 a shirt at that point. And when you're just out of college and someone cuts you a check and your profit's fifteen thousand dollars, you're like, whoa, I I've made it here. Unfortunately, that was the only sale I got from them because they're they're uh the the company that signed them said, Well, we have a distribution company that handles merchandise, so who's this Allen guy? And I to be um yeah, it was uh the they're still not around, but it's the electric love hogs. And I'll never forget I still have their CD, and uh I the the my my cla my claim to fame was I got to grab the CD and you know they have the credits on there, and I was, you know, they put me on the credits, and um, you know, great guys, uh you know, rock band music back in in the in the early 90s. But in any case, that taught me, and there's a lot of uh lessons I learned because the company I worked with to get the t-shirts done went out of business. Then I had to, I literally went to the factory with silk screening myself. I learned like how do you face adversity? And I loved it. Like it was three in the morning trying to figure out how to fulfill this order, and I was I was in my element. So um yeah, I was in my zone. And then and then I went through this discovery process because I always kept my cost down. So I always tell entrepreneurs, you know, if you can put a roof over your head and food in your mouth at a very low cost and not get caught up in the expenses of life, you have space to find things. And I was really good at that at a young age, and it was something my father taught me. So I lived pretty meager where all my friends were, you know, having their first jobs and being able to go out to dinner, and I just didn't do that. You know, I was just like, let's keep my cost down. And then um I got into the telecom space because I saw this need. This is back when we had telecom at uh you know 20 cents a minute for a phone call, you know, back in the in the 90s. And that business, I say, came at the right time where I teamed up with my college roommate in the mid-90s. And the second telecom business I had was like, hey, there's this internet thing. Why don't we just leverage this internet infrastructure to run a telecom business?

Mike Maddock 9:33

And just like how AI is a big deal now, we yeah, and uh you're surrounded by giant companies saying, No, that's not how it's done, I'm sure.

Alan Ezeir 9:43

You just decide yeah, and I'm thinking, I'm thinking, well, we can buy time cheaper and look for a segment of the audience and charge them 10 cents a minute or five cents a minute or three cents a minute. And this is back when that case, and over a period of a couple of years, we built up a base of 50,000 customers that were paying us. We have three employees, so very AI-ish in the sense that we use the infrastructure of the internet to do billing collections customer service. This is before you could actually make a phone call online. So we still had a traditional phone call. So that business grew, but then it went to all you can eat, you know, like right now, a phone call costs nothing, and we immediately needed to pivot. And that, I think, is like kind of lesson number two, which is oh shit, you can be at the business at the wrong time. And we were at the tail end of an industry where you could still stay in it, but it could be very difficult. And that's how we got into the domain business because we scoured we were on the internet, we're like, what other internet businesses are recurring revenue, service-based, kind of have some uniqueness to it. And domain names were the easy transition from telephone numbers or phone calls. And uh that was the the aha moment. And looking back at it now in 1997, 98, we were there at the right time, right place, took the the chance, couldn't do it now in 2026.

T Shirt Chaos And Loving Adversity

Mike Maddock 11:06

It'd be very difficult. Yeah, question for you, Alan. You said you you your college roommate became your partner, yeah. And I've written a lot about uh the ability to pivot and how it can be like a superhero power. And for me, it's also Achilles heel because I like to pivot too much. Like, let's change it, let's change it. Who was it? Was it you or your partner that said who's better at pivoting? Because one of you had to be good at follow through. One of you had to be like, okay, we figured this out, let's scale it. Can you speak to that?

Alan Ezeir 11:40

Yeah. Um, so I think if um to break up our skill sets, uh, he was very good at seeing around corners and seeing what was next. Um, and he was a programmer. I was good at the people, operations, legal, uh actually understanding how to do a PL and saying, you know, you you have to make money. So um and and so that, but on the pivoting question, I think we were both on the same page. I think what ended up by happening is we we used that we used to have this comment when we would get interviewed back then, is he would jump at everything. I would grab one of his legs and say, let's not jump there. Yeah. And then he would jump again and I'd say, not there. And then he'd jump again and I'd say, there's a good one, let's both jump. So I think he would jump too fast and I would analyze it just enough and then say, okay, there's the one that has the least amount of risk. Because you can, you know, if you take too much risk, you're gonna, you know, you're gonna crash a burn.

Mike Maddock 12:44

I'm gonna look back. Can you can you understand or do you believe that you were really lucky finding the right partner early? Yeah, so so many partners get together and they have the same skill. They both want to jump. They both want to jump, or you know, and and it it doesn't work. It it it it's uh so I I I see partners at work as uh like the third or fourth or fifth partner is probably not luck, but the first one, if you get that one right, man.

Alan Ezeir 13:14

So so Mike, you're you're speaking right into my heart right now because um I've spent a lot of time in the last year trying to replicate that. And I've actually used AI to say, here's what happened when I was 19, 20, 25, and and it, and I have this word that I printed, and it's just serendipity. And I believe I was it was a very serendipitous moment that I met someone that we had complimentary skill sets, we had the same vision, we had the same, we were, we were young, we were ambitious, um, and we moved forward. Now, frankly, like after two decades, that partnership ended because we've moved in different directions. I've been over the last decade, because it's been a decade since that relationship, I've been trying to replicate it. And I've literally like my vision going forward as when we first spoke, um, and I've done a lot of work on this, is I'm not actually looking for the next business, I'm looking for the next co-creator, someone that I can co-create with. And I have a list of one, two, three, four, five, six people on my desk here that have made the cut out of 20 that I've been meeting with, and eventually I'll cut that down to three and then two, and maybe co-create with two and then see which one works. And I don't care if we sell ice cubes or AI tools. It's like I need to find that person because I'm better when I'm co-creating with somebody. So you hit it, you mailed it when you said that.

Telecom Boom And The Pivot Moment

Mike Maddock 14:42

So I just sent uh the final transcript to a book called Your Seat at the Table. It's the same name as this podcast. Uh it describes the um the six seats at the table: the operator, the strategist, the rainmaker, the visionary, the tech futurist, and the orchestrator. Yeah. And one of the chapters that is um and it describes like the superhero power and blind spot of each one and how you build a team. So it's something I think about all the time. So and I should tell you that when I speak, I I actually use the phrase manufacturing serendipity. I like it. Yeah, like because some people seem to be able to do it. You you know, you hear, isn't that guy lucky, or isn't she lucky? Isn't she lucky? And then you notice that they're lucky again and again. Yeah, like luck. They're doing something. Yeah. So so like permission, just a quick digression. Um, I I know uh because we've spoken in the past about all the different businesses you've had, I also know you have children the ages of 10 to 40, right? One of them is a if I remember correctly, a sports caster is a dreaded icy tundra of Green Bay, Wisconsin. Even saying that. I know. What is how how, as a dad who is a really successful entrepreneur who is clearly willing to share wisdom, like hard-earned, I've got the bruises, I've got the scars, I made a lot of mistakes, wisdom. How does that affect your parenting?

Alan Ezeir 16:21

So I um I've learned early, and I don't know if it was just, I think it was my mother's influence on me that you can be anything you want to be, but don't be anyone that you're not. And um I respected that because it wasn't, oh, be a lawyer, doctor, you know, because that's a safe path or that's a path that will give you notoriety and money, fame, whatever it may be. You know, find out who you are. And in the parenting side, I was very good to watch my kids' actions and then give them, I had the opportunity to give them opportunities. And then you watch. And I had two children, and and one's 27 is my daughter, and my son's 25, who you said is in Green Bay. Um, and both of them picked careers that I could have told you when they were about 10, 11, 12 were very in in the interested in. And my ex-wife now, but my wife then kind of said, Hey, let's nurture this, and if they don't like it, let's let them shift. And I think not getting caught up in the like I I did try to influence my son. I'm like, hey, you know, traditional network television is probably not the way to go. Why don't you team up with some people and start your own channel on YouTube? And he's like, Dad, I'm not like you. I want to go get, and he said this early in life. He's like, I want to go get health insurance. And I was like, wow. Okay. And I knew he was very much uh needed that safety net. And I just never needed it. So rather than pushing him there, I put him in front of everybody, and I figured what would stick would stick. And my daughter ended up by becoming a school teacher, and we knew that she was going that direction even before my son. So it's so I think allowing your children space to learn and then not trying to, you kind of give them options, but don't drag them there. Um, with that said, my son recently came to me, uh, and I I feel like it was a mistake in my parenting. Um, I used to play golf. I played golf for about 20 years and then just stopped because I just got less interested. Uh, and we were members of a golf club, it was close to our home. And he told me recently, he's like, Dad, I'm mad at myself for always complaining and then not wanting to go play golf with you.

Mike Maddock 18:50

Yeah.

Alan Ezeir 18:51

And I pushed him a little bit, but I didn't want to, I didn't want to like make him do something he didn't want to do. And part of me kind of wishes I pushed him a little bit further because he now plays golf and he's like, God, I wish I had that time to learn younger. So there's a balance between going, this is better for you, versus, you know, you got to find your way. So I can't say I did everything right. I definitely didn't do everything right.

Co Founder Balance On Jumping

Mike Maddock 19:19

Yes. We uh I think if we knew exactly what our parents did right, we would just do it, but none of us know. You know, we do the and then the other thing is your kids can be so different from one another. Entirely it in the Midwest, we say you plant corn, you get corn. Uh, that's not the case in my family. My kids are pretty much opposite of me. You know, they they might laugh at similar jokes and they might, but I'm like, I've always been like, what could possibly go wrong? Let's just try it. And they're very like, no, no, no, you one step at a time. So I let me ask you some questions about um what you see because you look at so many businesses. You might look at more businesses in a month than most people live, you know, look at in a lifetime. Um do you see any patterns that CEOs miss or or something that they think investors care about that they really don't? Um what they miss.

Alan Ezeir 20:22

I think um the one, uh it's a good it's a good question. I'm just trying to think of things that I look for. Um, and the two things I look for is getting validation from enough resources to know the timing of that industry or product. So that's number one. I like try to go because no one can predict it. You know, no one could have predicted the iPhone and 07 would have changed everything, but we're all kind of like, hmm, this is an interesting device. And now we look back and say 07 was probably one of the biggest changes we had in our generation um in what happened in industry. Um uh people's ability to be resilient. Um, so uh I think not every entrepreneur is created equal and resilience with some common sense a little bit, like not uh haphazard resilience where you just you'll do it until the dying end. And I've watched many entrepreneurs do that, end up with a half a percent of their company. And all right, that wasn't the smart way to do it, but doing it with resilience and and picking the right people. So when on my in my seat, I'm like, is that the right person that's gonna go through the war and is gonna do the hard things? And are they recognizing timing and there's a little bit of luck in timing? So um I I I do believe what people get caught up in is and no one ever should get caught up in this, is falling in love with the product or service. Yeah, you really can't do that.

Mike Maddock 21:54

I just like we talked about being a rainmaker, you need someone. That is just so in, and they're a huge cheerleader, and they're all in. I think there's this tension between grit and quit that is really important. Like I have friends who are entrepreneurs and they quit so quickly. They're like, Yeah, it's not gonna work. Me, like I've got a burning carnage of a business, and I'm trying to get keep it going. Like, what are you doing? So, like sometimes being all about grit is worse. Yeah. And people are like, Nope, you gotta know. So I wonder how you I think you learn that over time. Yeah. How do you pick that when you're investing?

Manufacturing Serendipity To Find Partners

Alan Ezeir 22:37

So, so it's very difficult because if we all knew we would just follow a roadmap, and I got some advice. Uh, and again, this may not be as relevant, but back when I was uh in college, I would go to a lot of networking events, and there was one called the Association of Collegiate Entrepreneurs, Ace, and it was a all that, and this is a long time ago. And Michael Dell was a keynote speaker. This is 1988, so he was, you know, I think they just went public or it was or it was early on. He had a $50 million company. He's not the way who he is now. And I remember being able to walk up to him and said, hey, look, I just need some direction. And he goes, see that yellow brick road? He goes, just start walking on it because what you st what you start today is not gonna be what is gonna happen tomorrow. And you need to keep Mike moving and seeing things rather than thinking about it. And I I think you've got to go with your experience, um, information in the marketplace, and uh, and I betting on somebody strictly because they had previous success is not a recipe for a win. But betting on someone that's never had it, yeah. Uh and then betting on someone that's never done it is not a recipe for a failure. So it's like you just gotta get a sense of do you do you believe in this direction and can and visualize it in the future, and then say, okay, who's got the the amount of grit and willingness to to to get it there? Um, you know, it's easy to everyone to bet on Elon Musk today, right? But seven, eight years ago, people are like, maybe he's a crazy guy.

Mike Maddock 24:20

And now he's he's like saying he's a crazy guy. He just has to be happens to be a crazy guy that's good at business.

Alan Ezeir 24:26

Yeah, and then if you look back, maybe the timing of SpaceX and Tesla are like just great timing too.

Mike Maddock 24:35

Yeah, and it's I I I have a real like the the best metaphor that I've heard is surfing, because you know you can be the best surfer in the world, and if you're a lousy wave, you look like you can't surf. You can be an average surfer and get a great wave, and you're like, my gosh, who is that out there? That's how business is. And I and I think that picking the right wave at the right time makes uh average business people look really, really great. So I love what you're saying about timing. Uh yeah.

Alan Ezeir 25:07

Mike, I have a good answer for you. It's and you just made me think of something, is being very um like being in tune with the repetition of what you see. So if you see something like an entrepreneur repeat something that is the right direction over a period of time versus the to making mistakes, then you're like, well, he's he's done it more than once. And when I mean that, not like a big win, but like an action. Whatever action happened along the way, um, that's when you start to go, okay, I'm gonna bet on that guy, because there's a higher likelihood. But when they only win once, you don't go all in on that because it could have been just timing and luck. So you got to see the repetitions and someone's kind of like I saw consistency in relationships, right? Like your spouse, when they're consistent with you, you're like, Oh, I've got someone that I can is predictable and consistent. Now, yeah, they they go off the rails sometimes, but that's okay. But you know you know them.

Mike Maddock 26:11

So yeah, they remarried um after my late wife passed, and um so four years after, but but um the I went and asked permission from uh my wife's father for him because that's what you do, particularly in the South. Sure. And he goes, Well, you know, you know, marriage is forever, right? You know that, right? And I kind of looked at him like and he goes, Oh yeah, yeah, you do. I had a pattern that we could easily recognize. You know, you're thinking of um in reminding me of the uh an entrepreneur in Chicago, Eric Lefkowski. He's had five or six businesses that have been pretty like some phenomenal businesses. And after the third one, I'm like, he's it's the same pattern. He is and it's a callback to your distribution. This guy is finding uh inefficient distribution systems and collapsing them. Every one of his businesses, that's what he's doing. And so I think, you know, if I was an investor, uh uh I I'd be like, there it is. He did it again, he's about to do it again. So that's his superhero part. It's like really, really great insight. Have you ever um have you ever backed the wrong idea because of the right CEO? You believed in someone so much that you're just like, all right, I don't see what this person's seeing, but I really believe in this person. They have a great pattern, so I'm gonna back them. Has that ever happened?

Alan Ezeir 27:43

Um, oh yeah. I've I've I've made the mistakes of falling in love with product. I've uh followed uh an entrepreneur that uh I didn't know uh, you know, really didn't want to be back, but wanted the money. And, you know, like you just and it's hard because it takes time to get to know somebody. And sometimes you can get to know them quickly. It's kind of like when you meet somebody, you're like, wow, I feel like I've known you forever, versus some people you're like, you know, I still need to get to know them because maybe I recognize something that they did that made me a little bit like unsure of who they are. So yeah, I've I always I I spoke uh once a friend of mine was a visiting professor at Cornell, and he said, Hey, I'd love for you to share your story. And it was one of the most fascinating things. I wrote down inflection points. And I'll tell you, when you look back, and I and I on the slides, I'm I I put it like a little red highlight or a green highlight, and the red was failures and green was wins. There was more failures than wins. And you're like thinking to yourself, wow, but it's like the analogy, you know, it's like if you're a baseball player and you strike out three hundred seven times and you're fine.

Parenting Without Forcing The Path

Mike Maddock 28:58

So and you're in the middle of fame. And that's how like that I I I um, by the way, before I forget the thought, please inflection points is the name of your book. That is a really, really great idea where because I suspect that there's a pattern to inflection points that entrepreneurs could learn from. Like, oh, and in in you know, in the West, I've always said the United States' unfair competitive advantage is that we celebrate failure. Yeah, we don't shame our family. Here it's like, oh, your kid's an entrepreneur? Wow, that's really great. Yeah, it's like you know, crash two or three businesses, but you still had it unbelievable. Where you know, in other countries you your family to you ever again. Yeah, is there something so you invest in a coup in a company? Is there something that just pisses you off? Like you all of us have lost lots of money by investing in companies. True. When do you get angry?

Alan Ezeir 30:00

Uh like I get I I I don't I don't I maybe don't get when I say I get angry, I get upset when there's an opportunity with someone, I see such skill in them, and they look for a way to get one over on you. You know, like they they they manipulate the situation in with a little bit of greed. And and I know you know, I have to remind myself, people are out for themselves, but maybe I'm in this for the joy of the journey, and I love the wins at the end, but you know, when I see someone going, your failure or me getting something on you is my win. I I get upset with myself, going, God, I wish I could teach you that that's not that's like if you start thinking energetically, that's just like bad for your soul, right? It's like around. Yeah, and it's frustrating because you see their skill level. Like I I'll use an example of a person I don't know, but his public persona is to do that. And it's Mark Zuckerberg, right? You hear the stories. I don't know if it's true or not, but it seems like he really pushed people down on the way up. But it could have been that he had the reason to. Maybe there was real reasons for for doing uh for doing so. It it it like I I just when I hear it, and I'm not I don't know Mark never met him, um, but when I hear the stories, I think about my own stories with people where I'm like, God, if you just worked with me, it would have been a lot better than if you tried to play that game.

Mike Maddock 31:42

So yeah. And that my trigger too is when things go south and I wasn't asked for help. Like I could have helped you. Like I it feels dishonest. Like I I I'm not here. It's okay. What what do you need? Let's let's figure this out together. Um is there a time when money makes a business worse?

Alan Ezeir 32:03

Um, yeah, I think it makes it again. The the the answer is yes and no, but the the real answer of yes is it makes it worse if it's in the hands of someone that thinks the money is going to solve the problem. Because the money doesn't solve the problem. Um, I think it sometimes uh deflates the the what you need to focus on. And and that's scary. So I think uh, you know, oh we have plenty of money in the bank, so we take the foot off the gas on things that are really important. Uh and I think it happens to everyone. It's kind of I heard an analogy recently, and spare the next 90 seconds, I think you'll really enjoy it. Uh, it's about the the cat and the cheese. And if you're the mouse and you're and and and you see cheese, you you run at a certain speed. If you see a cat, you run at a certain speed. If you have cheese and a cat, you run 10 times faster because you have motivation to get something and you have someone chasing you. And I think everybody needs cat and cheese. You know, they they need they need that. And this was scientifically done with a uh with a um a spring, and i i it will not get into it, but I'm constantly now sharing like, do I have enough cheese to chase? And is there a cat? I don't need to be feared, but I just need to know that I'm moving that direction because something like obviously Elon Musk's his cat is he thinks the planet's gonna die. His cheese is he wants to habitate another planet. I mean, those are two big things.

What Investors Actually Look For

Mike Maddock 33:39

Right. Yeah. I I think it's important. Yeah. I I uh I like saying that everyone has a ghost. Um, they're either being chased or chasing the question who's chasing who. My I and I the the it's a chip on the shoulder, the you know, the the parent that didn't believe in you, the English teacher that said you were stupid, the coach that said you'd never amount to anything. I I um and the the challenge though from my seat is that eventually, unless you really understand that it's cat, it's a cat and it's cheese, like it's a king, like if the most evolved leaders that I know, they get it and they they they actually have fun with it. Like, okay, you know, like you don't think I can do this. I got you. But but if they don't, if they haven't realized that that that they're being chased and what's chasing them, they can they they become neurotic a-holes. I mean, you know, like and it's like, what is your problem, man? Yeah, I like leaders who have figured it out, you know.

Alan Ezeir 34:45

There's a there's a a book called Um Mastering Fear. I was just looking it up on Audible. And uh my favorite quote in the book is the lion's not gonna eat you. And the moment, the moment you get comfortable with the lion not eating you, it's not like you just say, uh, you don't worry about anything. You just know the lion may get really close, but it's not gonna eat you. You know, it's gonna be okay. And the more calm you are through that, you know, you've got to be resilient, you've got to push, you've got to think strategy, but you the clearer you are, the better off. And I read that book because I thought the lion was gonna eat me at one point. Well, I didn't say maybe that, but I I was worried and I was like, why am I so fearful right now? Yeah, and I'm like, I shouldn't be fearful. Horrible thing.

Mike Maddock 35:34

And then I learned to let it go at night. If if me. You wake up in the middle of the night, you're hurt. I I actually I I've been going to um a thing called Gathering of Titans. You you should talk to the class. It's a I'd love to, yeah. It's an entrepreneurial conclave. We've been getting together for um 22 years now. It was a three-year program sponsored by MIT magazine and entrepreneurs organization, EO. Yeah. Apply to get in. At the end of three years, you graduated, they gave you a certificate. We went to Vern Harnish, who was the person who started it, a friend of mine, and said, we want to keep going. And I was like, nope, it's it's three years. So we gave him a Rolex that said thanks from our class. We collected credit cards, we nominated a chairperson, and that was uh no 22 years now. So we've grown up together. Um, and at one point, uh maybe 10 years ago, I was having anxiety attacks and I was waking up in the middle of the night and like I couldn't catch my breath and I didn't know what was happening, and it was just completely irrational. My subconscious was had me. And I remember asking the class, like in front of everyone, has this ever happened to anyone? Can you raise your hand if you this has happened? Um, 75% of the class raised their hand, and no less than 10 people came up to me later and said, I got rushed to the hospital. I thought I was having a heart attack. So anxiety that that, you know, what is it? Like, am I gonna get eaten by that lion is so real for uh for entrepreneurs. And I think that um the way I define entrepreneurship is if you fail, the bank comes and takes your house. So you know, have something to say about this.

Surfing Waves And Pattern Recognition

Alan Ezeir 37:24

Yeah, yeah. You know, when I get to the stage where I get worried about something, because I still do have moments of like, wow, I'm not sure what the the path is. I can't see the path, and you're not you're not gonna always see the path, the tunnel will be dark. Is I always remind myself 99% of the things we worry about don't happen. So if you're a betting person, I'll take that bet. You know, I'll throw a worry on the table and say, Do you want the over or under? It's gonna happen or not happen. And I bet you I'll win if I just say it's not gonna happen and you take it's gonna happen, I'll probably actually, you know, you'll eventually win because something will happen. But uh, but most things don't.

Mike Maddock 38:08

Yeah. I mean, all the research about people that live to 100 years old and what is your number one regret, every single time it's I wish I'd worried less because it didn't happen, but it robbed me of the moment that I could have had. And it is such a valuable lesson. And if I could hypnotize everyone in my life, including myself, to do that, like eh, you know, but it's it's it's hard to do.

Alan Ezeir 38:36

Um but it's at least a way of a reminder.

Mike Maddock 38:39

That's a good reminder. So let me ask you some um I'll ask you some some macro questions and I'll give you some rapid fire questions. Sure. Is there a trend right now that you think CEOs you're seeing it, but CEOs are underestimating? Underestimating. Um have a bigger impact on the world than people think it is.

Alan Ezeir 39:06

Are they underestimating? I mean, I know what some of them are overestimating. I'm trying to think of underestimating. I mean, the over over the overestimating is I really do believe they think this AI wave is going to change everything. And I think it's it's oversold right now. And um, and I feel like I have enough valid evidence to say it it's a it's a it's a methodology to assist businesses and it will change things, no different than the internet changed uh physical uh ways of doing business to doing things online. But I think they think it's going to increase profitability and decrease costs so much that everybody's gonna win. I think certain industries will, and certain ones, they just there'll be there'll be impacts, but not so grand, you know. So that's my opinion.

Mike Maddock 39:58

The economist in you saying that.

Alan Ezeir 40:00

Um, that's the is it that's no, that's that's the person that was will watch the internet being birthed and watched everyone overblow it then and go, wow, I'm hearing the same story all over again. Now, granted, I see the value of what the internet does, but I talk to people that are very involved with AI, and when I ask them the point of question, is like, what problem are you solving? How are you implementing it? And show me some ROI. And they're like, there's a little bit of that moment of we'll get there. And I'm like, Yeah, all right, I get it, but I still don't see a hundred percent of it.

Mike Maddock 40:39

So yeah. I was in uh, you know, I I have these flourish advisory boards, which are CEO roundtables, they meet virtually, and recently um one of the an operator, the operator seat of the six, uh said, We're really seeing some incredible things from the AI right now. And you couldn't, I mean, it was like all of a sudden everyone's like, What? Yeah, you present on it? Because you know, the operators are from the show me state. They don't take any of the assets it's like I don't believe any of it. So when an operator says, actually, we're getting some stuff happening here, everyone wants to hear about it. When visionaries like me say it's gonna change everything, people are like bah bah. Okay. So so that's the thing they're they're um overestimating. Oh, yeah. Do you think is something they might be underestimating?

Trust Breaks And Money Mistakes

Alan Ezeir 41:31

Um, I think that underestimating that they they better implement it or they're gonna be in trouble. The ones that are so pessimistic, I do believe like if you don't look at your business and be realistic to know that it's gonna affect one person's business different than it's gonna affect yours, it's not a unilateral uh uh change for everyone, that you better like be on board because either you will be, you know, I think j uh um Aston Kutcher said this at a conference that I was at, and he goes, eventually we are all going to be AI enabled. Every person and the the difference between you and someone else will be did they AI enable themselves? Yeah, did they yeah, yeah.

Mike Maddock 42:16

So makes sense. It's um yeah, there's plenty of analogies there. Yeah. Okay, a little bit of a pivot. Yeah. Tell me what failure looks like for you. Like if if from your seat, with all you know, yeah, how should a CEO think about failure differently than they do? Think about it or how do what how how well I see it? Like how do they so I see it how to see it? Yeah. Uh I try to get mostly CEOs to listen to this or feel CEOs. So yeah, I I think I think so.

Alan Ezeir 42:48

Failure is is is is these lessons that you get to pile onto yourself so that you can do better next time. So that's how I I look at failures. I get upset with myself when I fail two or three times at the same thing and go, why am I not learning? What what is what's what's my roadblock that I need to break through? Um, so uh not to be afraid of failure, not to want to fail, but to at least accept failure as part of the process. You know, it's it's the it's miss the shot so that you can take it again and to perfect it, uh, learn from others. And now I feel like I can recognize a better opportunity and have less chance of failure. Still, there's opportunities of failure, but it's still um, I I I say no a lot more now because and and I and I'm not always right, but I say no a lot more now because I I I feel like I take those lists of failures and say, eh, that is a high likelihood to happen again. May not happen, but why why go down that road when there's too many identifiers that are going to put me in that position? Um, so So let's uh let's go a different direction.

Mike Maddock 44:02

And and you know, yeah, one of my one of my uh friends and mentors, a coach, uh I once said, Yeah, my instinct is to do this, Rich. This is Rich Hill, a buddy of mine. He goes, Is that your instinct or your intuition? And I said, What do you mean? He goes, Well, they're both really important, but they're different. Your instinct is what sees a stick on the ground and your brain says snake and it keeps you alive. Your intuition is the sum of all your experiences. So I like that. Hear yourself think my instinct says thinks this to stop and see if you're making decisions from fear or from wisdom. Yeah. It's really profound because what you just said was it's wisdom. You run a lot of experiments. You might be afraid you're gonna make the same mistake again, but your with your intuition is like, this is a pattern. I've been around the block a few times. This feels like a no for me. Now I could do some digging and figure out why, but this is intuition. Yeah, yeah.

Alan Ezeir 45:05

Yeah, I 100% agree. And I could I I I never uh go back and say, was I right? Because that takes effort to go, you know. You some of them, some of those things you can figure out fairly easily, but others you can't because no one has a crystal ball. So you don't know no. What did you learn about ego in business? Like that yeah, like plenty of time. Yeah, oh, ego, wow. Um, well, there's the ego in self, right? The the thing that you're like me against me when I'm in the gym, I'm like, I look around and and the trainer I work with, he's like, well, and I go, no, no, I'm fighting against me. Like, I don't care what the person next to me is doing. And he still always tries to, you know, make it like a competition. And I'm like, I don't know, I'm competing against myself. So that's just so um I think ego is important because you have to have that um that uh I you know I'm going there and I'm the one. It's the it's the level of ego, I think, where do the is it an earned ego? Is it a ego that they're allowed to to and and and how you portray it? Because I am a big believer that you know I want to enjoy this journey with the people. And I when I see egos that are out of control, I don't care if they're really smart, it's just not enjoyable to be around them. It it bothers my nervous system. So I think there's an ego level that is a healthy ego that helps you kind of transcend and grow and see things and enjoy the process. And then there's ego where it's just I call it childhood trauma that someone needs to have throw out their ego because they haven't solved something of their past. And and I just say, you know what? I I look at them and say, you know, best of luck to you. You know, I just don't need to solve that for you. And if you need that um ego to feel right, um, then you know, go at it on your own or find other people. And and they may be incredibly successful, you know. It's uh uh but at the same time, it doesn't work with me.

Mike Maddock 47:12

Yeah, I I there's uh some more things you say no to, like you're yeah, you're a project yourself. You don't need to be working as someone else. I like that.

Alan Ezeir 47:21

Yeah, yeah, yeah. There's it's a the circle, as uh uh a friend of a friend said, your your tent gets smaller and smaller as you get older because you allow certain people in your tent, and then you're like, there's no more room in the tent. I just don't have time for that energy or that ego or that that personality that's going to disrupt things. It's no different than in small groups that you know in my YPO group. Sometimes we add a person to our group and it just changes the dynamic. And sometimes you add them and it changes it in a good way, and sometimes it changes it in a really bad way. And you have to you have to recognize those personalities.

Fear, Anxiety, And Worrying Less

Mike Maddock 48:00

Yeah, I like the frame um is this giving me energy or taking energy. And it's a really good barometer for how um whether I'm engaging in the right uh conversations, the right uh communities. Um and I it it's uh you know, so some of the things I wish I'd realized much younger in life, you know, because I've I've gotten pulled into a lot of drama because I thought it was giving me energy, but it was actually a total suck. Okay. Okay, well, you have you have a you have a follow-up to that? Go ahead.

Alan Ezeir 48:39

I was just gonna say, I think you have to rather than say, you know, I I wish it didn't happen, I think part of each of our journeys is the sum of all our experiences. And as much as some of them are painful, if we sense that we have grown as as people, um those experiences were necessary. And I I don't think we have as much control as we think we do. So it's you know, I could sit there and say, you know, your past is is a lot harsher than mine, or vice versa, or compare it to someone else. We all just have this, this, this, this, some of these experiences, and we have to be okay with knowing that that's who's made who we are, you know, that that's how how we've become who we are.

Mike Maddock 49:21

So very wise. Thank you. My friend and Yoda coach John Domsky says that life is the perfect curriculum to teach you what you need to learn right now. Yeah, so that's a great way at looking at, yeah, that was hard, but I learned something. It was good. Thank you for that. Um, okay, so a few rapid fire questions. Um let's see. Uh one question every CEO should ask himself before taking capital. Why are you doing it?

Alan Ezeir 49:57

And I have a lot of follow-up questions to that. It's like, you know, like what is the true reason you're taking that capital? And uh, do you know the people you're taking the capital from? Have you done the homework? Uh, what are you gonna use the money for? I I wish I could give you one answer. There's so many answers there, but yeah, but what are you gonna use the money for is probably a big thing versus just taking capital for the sake of taking capital, you know?

Mike Maddock 50:23

Yeah, so I think that um lesson that everyone should learn from Shark Tank is that Mark Cuban wants to know what the money is gonna be used for. Like it's like, okay, how much is the cost of acquisition? Like he wants to know exactly when you pour the fuel on this fire, where is it burning? How is it burning? You know, or if you can't answer that question, then you can't have any money. Um, so yeah. Okay. Um, is there a founder you bet on over and over again? And if so, what why? What is it they do differently? This might be a callback to a question you answered earlier.

Alan Ezeir 50:58

You know, um I don't have one, but I do know that there's repetition back to the thing we talked about is recognizing repetition and knowing that the odds are best with that. I do have actually somebody in my network that um I invested with and I continue to invest with, and uh the odds are always better with them because they just fight harder than most people. So I I do have someone like that. So I and I've just watched the way they think on calls and the questions they ask, and then the action steps after the call, and I'm like, all right, they're working harder than everybody else or smarter than everybody else, so I'm gonna bet on this horse.

Mike Maddock 51:45

Yeah, they refuse to lose. Yeah. Is there a what's the biggest? I I hear so much um quiet conversation about private equity. What's the biggest myth about private equity?

AI Hype Versus Practical Adoption

Alan Ezeir 52:00

Well, I think it became this popular fad to get into the private equity space. So they everyone equates private equity as these finances, the finance orders that come in and they ruin industries because they don't know anything about business. And granted, if you put enough apples in a in a bucket, some of them are gonna rot. And if you start to overfill it, some of them are gonna get squashed and shouldn't be in the bucket. And I think what we've lost sight of is not every private equity firm or group is created equal. And that makes it just harder to fish through who's best to work with. It's it's I think it's very much like the dating world. There's so much top of the funnel and opportunity that now you no idea like how to pick a spouse because it's a lot harder because there's just too much influx of opportunity to meet people. So when you do, you're like, wow, I I've you know discovered it. I think it's it's being intentional, asking the right questions, and not going based on, well, my best friend used this firm, or they have a reputation that I heard about. You gotta really like like dig deeper than that. You gotta date them.

Mike Maddock 53:18

Yeah, yeah, yeah. You you you said something, uh it's kind of like picking a spouse. And I know I'm not gonna pull the thread now, but that might be a few uh podcast. I know that's very interesting to you. Very much so. Um it's sort of a side project of partner and partners. Oh, yeah. I'll put that on a shelf and maybe we'll do a a follow-up because I think that'd be fascinating. Um, okay, last question for you, um, Alan. If you could tattoo one principle on every entrepreneur's arm, what would it be?

Failure, Ego, And Rapid Fire Rules

Alan Ezeir 53:55

Be passionate. Be passionate. If you can't be passionate about it, in the worst times, you need to get up and say, I still want to fight. So be passionate about that thing. If you're not, I always tell myself, if business goes to shit, will I still enjoy this journey? Like, because it's gonna probably have a moment and you can't tend. Yeah, yeah, or yeah, yeah, yeah, yeah. You're right. It's gonna have, but at least if you can't get through the first moment, you're not gonna get through the other nine, right? You know, so you gotta, you gotta, you gotta like sit there and go, you know, I have a perfect example is you know, I I I started a fitness business in 2004, and I remember before I wrote the check to sign the lease and the and the buy the equipment and everything, I was like, will I regret this on my grave to at least not do this? And I was always into fitness and I couldn't find something that fet fit my needs. So typical entrepreneur, let's start it. And um, and frankly, the business net net didn't make money, but I enjoyed the eight years running it uh with you know, I didn't do the heavy lifting, but I enjoyed the process. I just I enjoyed the process. And I and I and I when it was hard, I was still passionate about it because I was like, I really like this space.

Be Passionate And Keep Going

Mike Maddock 55:16

Yeah, I I I don't know if you ever read the book Shoe Dog by Phil Knight. If you haven't, yeah, please do. Oh I remember he he wrote three or four times in the book, his mantra was just period keep period going, period. And I have written that so many times, like just get through this, like you'll get through it. It there's the there's another side. Alan, thank you so much. Um thank you. I really appreciate it. I've enjoyed chatting with you, and I hope that uh the listeners out there listened all the way to the end because there's so much wisdom in what you say. Oh thank you, and it's hard earned, so I'm so grateful. Thank you. Thank you.

Alan Ezeir 55:54

And I look forward to coming to visit you. Uh Chicago's not far from Green Bay, so I I I'll probably be out there. Go to a Bears Packers game. Hey, you know, why not? Why not?

Mike Maddock 56:07

Why not? All right. See you in the icy tundra, Alan. Yeah, thank you.