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A
Hey, everybody. Welcome back to the Unemployable Podcast. I'm Jeff Dooden. If you were raised in a family of entrepreneurs, bought your first property by the age of 23, and in your 40s, owned more than 120 companies, if you leveraged your experience to build the empire operating system now used by over 3,000 companies worldwide, and if you launched the Aspire Tour, billed as the largest business tour in America, all the big names on it. And if you have leveraged your success for impact, and through your foundation, feed and educate over 4000 children globally every single day, your name can only be the king of exits. Eddie Wilson, welcome.
B
Thank you. Appreciate it.
A
Yeah, yeah. Excited to have you on here today and very inspired by what you've done. And, you know, it's interesting. We get out into these. Into these circles, and I. I just candidly, and I know based on listening to you, you won't take this offensively. I didn't know who you were.
B
Good.
A
You know, and. And then as I got into your background and history and then really listened to you on a lot of podcasts, I really developed a deep understanding, a deep appreciation for your approach to life and your approach to business. Which leads to my opening question, which is this. Historically, how many decisions do you make with lessons for your children in mind?
B
I think that that is always on my mind as a dad of three boys. You know, so much of life and what I'm creating is really is an example to them, and I don't always do it well, but, you know, it is very much at the forefront. And I would say 80, 90% at.
A
Least, when I heard you mentioned something like that, and you didn't say it directly, but I picked up on it. And I've got three children, 27, 24, and 21, and they're my greatest work. Like, it's. That's my gift to the world. And I've, you know, however it worked out, my wife and I, between. We're drastically different in the way that we grew up, and. But the combination of us and the attention that we paid to them, really, I'm very proud of all. None of them. None of them have given us a bit of problems. But more importantly, like, every time I wrote a book, it was to say, I want to put this here for. So that they can understand who I was. I mean, and I just. When I heard you talk about it, I really think that along with, like, for me, that's a purpose. It's a great purpose. And if you take the people that are closest to you that you care about and you use them as a litmus test against doing the right thing. Doing the right thing when nobody's looking. If you know the right thing to do, then do that. I think it's a great near filter to you to make really solid decisions.
B
It is. That's 100% the way that I live my life today. It's not always the way I've lived my life. I think that when I was in my younger years, I have a 24 year old, I have a 19 year old and I have an 11 year old. So we're all spread out. But I had my first when I was 22 years old and I would look at people that would say things like, maybe one of the greatest accomplishments I have in life is raising good kids. And I would think, you know, in my 20s, I would think, well, that's a cop out for people who don't actually do anything big in life. You know, all of a sudden you get to a place where you have teenagers and young adults and you realize like, oh, that's so true, like that my greatest accomplishment is if my children live in, purpose, create impact in the world, you know, have joy and happiness in their lives, raise good kids. It's like that is the greatest accomplish. You could sell 100 companies. And I don't know that it would be any harder than raising good, solid human beings as children.
A
Capable, contributing, independent. That was my litmus test. And if I could accomplish that, I had a simple model that was truth, triumph and self determination. And I grew up in a very unstructured. I mean I was 12 and 13 years old. I was working in a Mexican restaurant in Chicago behind a bar, lighting people's cigarettes. I didn't grow up in a nuclear. My mom's still alive, but she doesn't listen to anything I do. So I can say it wasn't great. You know, I love her, I moved her down here to be with me. She's in a great place. But you know, but what that gave me was and nobody lied to me to protect me. So I didn't have the habit of lying to protect my children and then triumph. I don't rescue my children because they can go through it, they can survive it. I'm not going to go advocate to the coach for their playing time and stuff. Like they've got to figure it out and they might even have to get disadvantaged and figure it out and then being very careful to make sure that their life is their idea and that they, they are Self determined in the way that they, they do their thing. And, and what that leads is for us. If you have that purpose, I think it leads you to build purposeful businesses. I'd like to hear you talk a little bit about founders. You've been a business owner, you've built a hundred and something businesses, you've had a bunch of successful exits. So at some point you turn from being an operator and then you figure it out and you're like, okay, these are the things that I look for in a business. These are the characteristics that I look for. Every business starts in a scrum unless you buy it. Everything starts with two or three people looking at each other wearing 11 hats. And then, and then you get to these six, seven, eight, nine figure exits. Where do, what is the journey of the founder as they go through that and where do they get stuck and where do they fail?
B
Sure. Yeah. I think that really there's three pieces to this journey. You have really a founder, which the founder is, is more of a position versus a title. You know, it's, it's the responsibility of it versus like the action that the tactical action needs to be taken. And I really think that there's really like three positions we have to grow through. It's really like operator, then CEO and then what I would just say is business owner. Right. And in the beginning, almost every founder has to be at least an operator. They may not be a great operator, but they have to operate to some degree. And usually that's the Achilles heel of most founders. There's usually they're visionary leaders. They've got the idea, they've got the passion, they've got the drive. And really what separates most of them is their willingness to take risk when no one else will take risk. They'll jump out of the plane with no parachute. That's usually what you know, is like indicative of a founder. The problem is, is that, you know, I use this illustration a lot. You know, I love, I love Roman history. Obviously I built a company called Empire Operating System. And it's the difference between Julius Caesar and Marcus Aurelius. It's like you've, you know, got Julius Caesar, who's this great leader in general, and he's what we would see as like more like a founder. And everything is on his shoulders. Everything rise and falls with him. It all goes through him. He's the bottleneck of Rome to the point where the sen. Ultimately turn against him, convince his best friend Brutus to stab him and kill him. Right. Like, because they felt like for the betterment of Rome. Like he had built it, but he had. He'd create now the ceiling that was preventing it from becoming what it could be. Marcus Aurelius is very different. He employs everybody around him. He gives everybody the accolades around him. While he's a great leader in general, he really then relies on everyone else. Now the question would be is, can Marx Aurelius really exist without Julius Caesar? Right. And it's like, and that's where we kind of get into this kind of founder, you know, issue is that you really need that ego driven, you know, aggressive founder to get something off the ground. I'm not a great founder. I'm a. The reason that I've exited so many businesses, because I've purchased so many businesses. I, I purchase people's successes and take it to the next level. But what happens is, is most founders get to a ceiling, and their ceiling is their ability to organize, delegate, and rely on others for their strengths and abilities. Because they're typically so ego driven and it's all about them. And they got it off the ground. And it was their idea that they then really struggle to then become the bottleneck. And I always say that it's the hero that ends up turning into the person that gets assassinated. You know, it's like so many heroes in that kind of founding position five years down the road are getting assassinated in the bathroom by their CFO and their, you know, all the people around them because they won't let go, rely on other people's strengths. And it's just a natural progression that I see a lot of businesses struggle with. And that's why, you know, the SBA says that less than 1% of all small businesses will get past $5 million in revenue. That that's what it is. There's a legitimate ceiling there. And that legitimate ceiling is typically created by the founder.
A
How is it that or. Or in your experience, do you see people make it through all three phases? And what, what does somebody have to do? Do they have to get in a bigger room? Do they have to humble up? Do they have to go through a crisis? What causes people to break through to the next level?
B
It's, it's usually all the above. And it's important that they almost go through all the above. The founders oftentimes they either they either break through because of an awareness that's created of their own lack or inability, and so they humble themselves, or they get humbled by some issue or problem, and they have to break through by then relying on others because they realize like they can't get it there. But typically that comes through crisis. So really it's typically a humbling, but it's usually a humbling of like self awareness or it's a humbling of crisis that then allows them to break through into. Now what does a CEO do versus an operator? And there's true functions that a CEO has to, has to exist like be in in order for a business to really truly grow and scale. And then obviously, you know, then a lot of people struggle with that third step which is now I'm just a, let's just say chairman of the board. I'm the, I'm the business owner, I'm a past person in this because somebody else has to be the CEO and leader to scale to the next level. And very small percentages of, of business founders, operators, CEOs owners ever get successfully through all three. And it take, it typically comes with awareness.
A
Real estate has been a focus for you early in your career, but as I look across the companies that you've built, acquired and resold, it's varied. What do you look for or what have you learned to look for in an acquisition? In terms of management team characteristics, when you see a business, what says that's an opportunity?
B
For me, I have bought a lot of different types of companies. I'm a real estate investor through and through. I'm a third generation real estate investor so that I get honestly businesses are different in that typically what I'm looking for is either, you know, I start with the jockey in mind versus the horse. Like I want to know who's running this business, who can I attach myself to Because I'm a great CEO, but I'm not, I don't want to get stuck in this operator, founder bucket in that I am good at helping others see that path and create that awareness of them stepping up into the next, you know, position for them. And so I'm typically looking and one of the big things that I would say that separates me from a lot of people is a lot of these business courses and people that run around the country and tell you to buy these, you know, businesses that buy these ugly businesses, buy these distressed businesses. I don't agree with that. I think you should buy people's successes, not their mistakes. Oftentimes you're not qualified to fix their mistakes and neither were they. And so now you're betting on the ability to change something that's going wrong versus accentuate something that's going right. So no matter what the business is, I'm looking for somebody who has successful but they haven't achieved the greatest success that's possible. So it doesn't matter what it is. Now the secret sauce to my success is that I build community first. And in that community I look for what services and products and needs does that community have. Then I go buy the products and then I have the trust of that community. They'll go with me. For instance, you know, I. We have the Aspire Tour. The Aspirator is nothing more than an aggregator of small businesses nationwide. And then when I got into that community, we have the one of the world's largest masterminds, about 3,200 members. And it's like, and all I did was I said, hey, let me see your P. Ls what are you spending money on? Well, insurance, taxes, all this stuff. And I said, okay, I can go acquire that. And then now I have a ready made customer list. And so now I'm looking at lifetime customer value. And they know like and trust me already. So I don't have attrition issues, I don't have acquisition issues. My cac, you know, customer acquisition model is very inexpensive. And so that's how I build and grow and scale companies. So I'm really looking at how do I serve the greater communities that I possess. Right. And I typically have four or five communities at all time was my next.
A
Question was how do you define community? So it's either a mastermind or you're part of some sort of a group and then you mine that information to see where the holes are and then you go out and build products and services to fit that.
B
Yeah, my dad was an amazing entrepreneur. Still is. You know, I grew up in a home of both mom and dad being entrepreneurs. One thing my dad used to say all the time was he said, eddie, just find out what people need and serve that you'll never lack for. You'll never lack for clients, you never lack for capital. And that is really what we do. Like I mine that data and I realize like, oh, they're being underserved when it comes to tax preparation or underserved in whatever capacity. And most of the businesses that I've grown scaled, exited are just that there's something that served a greater community.
A
I have many friends and maybe myself too. I had an exit in 2019 and I got pretty broad. I think I ended up my, my business coach, my mentor said resist the urge to do, you know, anything bigger, better, the same thing. Bigger, better, faster, take some time. So I heeded his advice I took three days off, and then by the end of the year, I had 42 additional K1s that I was getting.
B
Yeah.
A
And not, you know, not everything worked right. Because I had a genius attack that thought that I would be successful. I had the golden touch, and people said, you had the golden touch, and then they wanted a little bit of your money. And, you know, I didn't get really, really hurt, but certainly learned a few lessons. But as I sit back now, and I'm six years removed from that and have a really nice stable of companies, I see commonalities and things that I look for, and then I see other things for me that are deal breakers. What are some of the things that you think are common amongst most or all of the businesses that you choose to own and operate?
B
Yeah, I really like Patrick Lencioni's model of hungry, humble, smart. I love when founders and operators are hungry. They still have a passion and desire. I love when they're humble. They'll take some advice, but they're intuitive, they're smart. I would say I'd add a couple of other pieces in there, but the biggest piece for me right now is that they have to adhere to a system. And if they won't adhere to the system, they have to come sit in a passive role with me. I don't mind taking people with me, and most of my exits have somebody with me. Like, I don't. I don't know if I've ever, maybe once or twice out of a hundred companies have I exited a loan where I owned 100%. I don't mind. I don't mind taking people with me. So for me, it's like, I really want somebody who will adhere to the system. I have a tried and true system. That system works. That system protects all of us, and it gives us insight into the growth of the business. And so that's where the humble part comes in. The hungry, humble, smart. It's like they have to have a level of humility that allows the changes to be made. If I. The deal breaker for me is like, as we're going through negotiation, if I'm going to keep the founder on, which sometimes I don't. Sometimes I have a. I have a bullpen of operators that I can, you know, tap on the shoulder and. And they can sub in. But for the most part, I'm looking for people who realize that they've hit their own ceiling in their own capacity and they're ready to take some help.
A
And you bring capital. Do you bring intellectual capital to that and human. Human capital. Capital capital and intellectual capital, all of it.
B
And one of the big pieces, I would say the secret sauce to what I do is I have my empire operating system. My empire operating system is, you know, like, if I'm going to invest in a company even passively, they have to overlay the system on their business. But the biggest piece is I have fractional, I have fractional people that are on my bench. So I have fractional COOs, fractional CFOs and those fractional COOs. You know, I can infuse into the business and immediately start seeing results right away.
A
Right.
B
But at a fraction of the cost. And so like, you know, I don't have to pay, I don't have to go hire a $200,000 coo. I can go tap someone on the shoulder for three or grand a month and I can put them in, they can train somebody that's already there. They can sit in just about any seat. And so, and they know my system. And so that's a huge advantage that I have.
A
Business owners get myopic. One of the questions I've learned to ask myself, if private equity walked in the door today and bought my company for me, what's the first thing that they would do? And we've got all kinds of reasons why we put things off and sacred cows and people and this, that and the other thing. But if you really took an unemotional view at a business from an outsider, if you were extra retrospective, it's amazing the change that you can make in your business and you can accrue the benefit. Because I think many founders in my experience, and we do, we do a lot of little acquisitions now we're, we're, I'm building a property services platform in the franchise space where just did a consolidation. We did five standups really, and had a lot of success over the last 30 months. So now we're consolidated and we're going out and we're acquiring businesses to add to the platform. And man, these guys are tired like these, these, you know, they've, they've bumped against the ceiling a little bit and now they hit their head really hard. And I can see clearly exactly what needs to happen. But for whatever reason, they can't or they won't.
B
Yeah. If that's great insight I have in my empire operating system, I really say there's five phases of business. Startup would be phase one, perseverance would be phase two. That's kind of your pre profit phase. You're in and out of profitability, ability. That's when you have right people, right seats, you have consistent capital, then scale, right? Like you never go into scale until you're truly viable. And then lastly, succession. Once I start getting into viability, we should be planning for succession. And the thing that happens is, to your point is when we go into succession planning, we ask the question, what if private equity came in, right. What would they ask us to change and what would we be willing to change and what would you be willing to leave? Like, most private equity just want meat on the bone, right? Like, so what they want is you to start the process, have a fundamentally secure process, but still have opportunity, you know, and so we have all those discussions and succession planning and it's the same, same exact process. If you're not willing to make the change that a private equity company would, then you really don't want the success the private equity company could have.
A
How many of your acquisitions or potential acquisitions come out of your communities because you've had the opportunity to get exposure to the business to see a little bit, learn a little bit about them? I think that's the Dan Martell model with SaaS Academy. Coincidentally, I have a mastermind in franchising called Fran Mastery, which gets me exposure to early stage franchise companies and provide them some value, but get to see kind of how they roll, how they operate, what they're thinking, what the results are. Was the original intention of building the communities to serve them, but also to create a feeder for.
B
No, my feeder for always was always linked to the Empire operating system.
A
Okay.
B
You think about those 3,000 businesses that now are essentially operating on my system, you know, and if they, if some of them I have insight into. So my communities really are a place of service. And so I'm looking for the businesses that serve that group now naturally, because, you know, they know I buy businesses, things have come that direction, but I don't really mind that group specifically for that. It's. But what I will do is I'll introduce them to my Empire operating system. And when they put the Empire operating system on their business, I can really see the gaps. You know, like it now we're speaking the same language. I see the gaps, I see where funding could really, you know, take them to the next level. So I would say that's kind of the bifurcation of that.
A
Got it. Do you use your own models or do you have outside coaches, mentors, perhaps board members, trusted advisors that keep you safe from your own genius attacks?
B
Yeah, you know, it's interesting When I was younger, I always tried to be mentored by somebody who was a step ahead of me, just always that step ahead.
A
Hard to find that now for you.
B
Yeah, you exit for over a billion dollars, and all of a sudden it's really, it's rare air.
A
Yeah.
B
And so what I find is, is my, my coaching, and I still have coaches, but my coaches are really more working on my interpersonal. The traumas I bring into life, my own limitations, my own ceilings. Like, I've found that, like, on the coaching, the business side, it's like I really, you know, not that there's nothing to learn over there. There's always something to learn, especially right now with like, AI and all the stuff that's going on there. But I find myself being coached more on the personal side and the interpersonal issues that I deal with, and really, like, my own limitations and my own belief systems. Like, I find that that's. Over the last three or four years is really been like, the direction that I've taken.
A
Have you done anything that you found particularly helpful? Meditation? Any. Any. What's, what's your particular cocktail for? Yeah, keeping, Keeping yourself in shape. Mentally, physically, emotionally, spiritually.
B
Yeah. I have a coach, and we actually bought his business for the purpose of acquiring him and his staff, but a guy by the name of Larry yacht, he's led SE3, I believe it was. Larry basically brought into my life this understanding that, you know, I. I've been through a lot in my younger years. You know, I lost a brother, lost a sister. We've had quite a bit of loss in my life. And, you know, but in my mind, I never thought I went through trauma, never thought I went through any issues. I, I thought, you know, I'm. I'm pretty solid. I've got amazing parents, you know, something like that. And what Larry brought into my life was that all of us have some level of trauma and that that perceived loss of control, not loss of control, but our perceived loss of control, create mental barriers, subconscious barriers. And so I've dove deep into my own subconscious limitations. You know, your subconscious is there to keep you alive, but oftentimes it's making decisions that are keeping you safe in areas that you don't necessarily need safety in. And so, you know, I find myself, you know, in weird ways, having massive success and then still creating personal suffering. You know, it's like forcing myself to go to the next level. Like, nothing is ever good enough. Things like that or, or choosing, you know, like, I, I. My nonprofit. It's like, well, We, I think we're up to 5,300 kids a day. We feed and educate on a daily basis. And it's like. And all I can think about is how to get to a hundred thousand versus really enjoying the 5,300 that we're at today. And so I find that, you know, all of that, most of what I'm doing, that cocktail you talk about is tied to this, to this understanding of my own, you know, self limitations based on my subconscious, you know, belief system. And so oftentimes it is meditation, it's prayer. I've got a deep faith and in a belief system that I was created for something greater but also tied back to the place, but I was also created. And in that creation I can experience joy and happiness and fulfillment. And so most of what I'm doing today, whether it's physical or emotional or mental, is tied back into. How do I seep deeper into that belief system?
A
You talk a lot about time. How far out in your life have you planned your time and how specific is it?
B
It's very specific. My father, as I grew up in his house, he basically would always elevate time over money. He would even not allow me to speak in the, in the confines of money. I bought my first car. And he said, I always went to buy this car. And I said, dad, I'm gonna buy this car. Are you good with it? And he's like, how much? I said, eighteen hundred dollars. He said, no. He said, you make five bucks an hour, you work this many hours a week. Or is this car worth this many years of your life? This car isn't money. This car is time. And he would constantly reframe that. And so it became such a huge part of who I am. For me, I'm on this pathway of by. I'm 46 years old right now. I have it pretty intentionally planned out to 60. Obviously, you know, I can't control health, I can't control various things, but I have this very specific pathway of wanting to create this endowment for my non profit. And by 60, I really want it to roll into a specific structure. But I, I'm pretty planned out and I have most of next year planned out by the day. I have that next year planned out by typically the month, and then I've got quarters planned out until I'm about 60. So it's very, very intentional.
A
Yeah. And is your father still with you?
B
He is, yeah.
A
Yeah. Sorry to hear about your brother and your sister, by the way.
B
Yeah.
A
What are some of the lessons looking Back that the little things that your father said kind of made you who you are today. We created, you know, as I was building my first national franchise company, I was raising my family at the same time. And if you think about a franchise brand, it's not a thousand people. It's 155 to 7 people. Little companies, little families, right? And they're all building a team. A team of employees and referral partners and everybody else in there. You know, the things that I coached our franchise owners to do by having a set of values and, you know, opera, you know, communicating what you know, communicating to people with such clarity that it's like you're speaking to fifth graders and things like that. So I built a set of values in my company, and then I built a set of family values. And it's amazing to me how with a very loose leash, I was able to put hard fundamentals into these kids by things that were said. They weren't throwaways. They were intentional, but it's not like they were beat over the head with these things. It was almost like I did Undercover Boss. And one of our family values is always do more than is expected. Fail fast and move forward. Trust yourself to take chances. Those are like the bottom three. It's live fun, be humble, respect others, be a servant, leader, never panic. And then those other three. Right. So that's kind of how we rolled. What are some things early in your life other than the one lesson that you mentioned that your dad. You can look back and say he put something into me that. That made me who I am today?
B
I think I really learned two great lessons that I think have served me well. One for my mother, one for my father. You know, experiencing the loss of my brother and sister. I experienced the loss of my sister when I was young, and I was really struggling through that. And my mom would constantly rehearse gratitude. You don't always feel or experience gratitude, but you can rehearse it, and ultimately, it does play its part. Gratitude really changes everything. And so, you know, when I was going through the loss of my sister, my mom would constantly bring me back to this place of saying, hey, Eddie, I know you're struggling. I know. I miss Rebecca, too. But tell me about the favorite toy that you got to play with with her. Tell me about your favorite moment. And, man, aren't you so grateful? And so, like, even though I was struggling, she would just give me to rehearse gratitude. And she would always say things like this, like, eddie, you know, gratitude in the valley in Your worst situation is a catalyst for your greatest growth. Because most people create limitations when they're in the valley. Like, you know, the first time I ever sold a company, I was taken advantage of by these kind of corporate raider types. And. But it was. It was me rehearsing gratitude in that moment that got me to a place where now I. I am where I am. You know, like, I could have been the guy that gotten taken advantage of, but now I'm. I've reversed that. And. And that's because of the gratitude that my mother had me rehearsed. So gratitude is just ingrained in me and it's been such a valuable tool. The second thing is that my father, other than the time, kind of the time constraint and the time consciousness, my father, even though my grandfather was successful, my father. It's very much generational, our family. You got to go out and find success on your own, and they really don't help you financially. It's just like, hey, you got to find your own path. You have to create your own success. They will give you resourcefulness, but never resources. It's like, hey, I'll open this door for you. I'll introduce you. But, you know, my dad would say, resources are going to be a noose around your neck if you don't know how to deal with them. And so why would I give you resources? So that was just kind of the family I grew up in. Well, he had the same experience, but he struggled when I was younger in that we really didn't have a lot. There were Christmases, but there were very little. And I remember moments where my dad would struggle with feeling the lack of success, like, feeling like he was a failure. And so it brought my dad into a place of. He's very, very conservative. He hates liability. You know, he and I do real estate together, and he wants everything free and clear, and I want to leverage everything, you know. And what I learned from him is really how to deal with fear. But it's interesting because I learned it by later in life, him expressing to me how much fear held him back. You know, it wasn't that he was going through it. He later on. And so, like, it's. And it's, you know, always an encouragement to me because that. What that shows is, is I can screw up earlier in life, but as long as I'm willing to live within the truth of what has happened and the truth of what is real, there's still a potential for success. My dad, later in life would talk to me a lot in my When I was building my companies, about how fear held him back and if he would have taken that step, how much further he could have. And to not let fear make your decisions. And so my, my dad gave me a really profound respect for liability and fear and how to deal with it emotionally so that it isn't making my decisions for me.
A
When you were talking about founders who. And risk and you know that they don't see the risk and they're big risk takers. That's me. Man to a T. And then my oldest son, he's our chief growth officer, but he went and got a finance and economics degree, and he is the opposite. We have different profiles for Personality Pro. We've done all the testing. Not the DNA testing. Nobody really wants to know, but, you know, we've done all the. We've done all the business type testing.
B
Yeah.
A
You know, he is. I mean, he says, I don't know how you've survived with your risk profile. And I'm like. But it always seems to work out. So it's, it's, it's really interesting. And again, I literally, I mean, my mom gave me a 72 Buick LeSabre, this was 1989, to drive halfway across the country on a football scholarship. And I had five T shirts in a. In a trash bag. Two of them had profanity on it, one was the M's. It was crazy. So for me, everything in my life is upside and I don't have the fear of loss because I didn't have anything. And. And now while I've become more responsible and certainly more thoughtful and continuing to want to get better, a better investor, a better business builder, a better steward of our resources for future generations. I still catch myself getting out over the tips of my skis. And what I've had to do is I've had to surround myself with great finance people. Like, great, you know, like, I mean, they need to tell me no and, and then to make sure that I'm not having a genius attack that's gonna, gonna do that. But I think it's interesting because with your success, it would one of two things. Either is you have a. You had a different risk profile than your father and. Or you're just exceptionally disciplined and good. Which is probably both. True. Are you a creative or analytical more?
B
I'm more analytical.
A
Okay.
B
Engineer.
A
By the way, engineers are 40% of the world's billionaires. And that's why.
B
Yeah, well, it is why I would say that I have a mix of both. Like, every test I ever Take whether it's predictive index or it's, you know, Myers Briggs or Colbier, whatever. I always bridge that gap in a weird way where I have a little bit of creative, like, I'm willing to push the envelope, but I also want to know how things work. And I think that most people in the space, it's like you're either competent or you're conscious competent. Conscious competent is just somebody who knows what has gotten them to success. And I think that it's that pushing a little bit beyond what everyone else would, taking enough risk, which is my father saying, hey, don't let fear hold you back. But it's also that analytical mind of saying, but what actually got me to success, you know, it's like, it's why I have the Empire operating system is like, I had success once, and I was like, oh, I could replicate this. You know, like, I.
A
Right.
B
Actually see the steps to it. And so I think that that's. I think that's the benefit of, of the profile. I have.
A
Yeah, I have the. I have a. I have a system to take a franchise brand from inception idea all the way through, you know, hundreds of locations every step. And every time I build. We're building five brands all at once right now. And, you know, we accomplished in five months what took me five years to do before. It's just because you have the system and you, You're. You understand what the growth is going to be and what you need to do and what you need to have to get ahead of it. Fascinating. I'd love to talk a little bit about your impact. Has it always been something. Were you always purposeful in your business building? Was it about the money first? Was it about security first? And then at what point in your career did you turn and say, you know, I need to use my skills and my resources for a greater good? And Branson, you know, it's a great book, is you can. You can do well by doing good. I absolutely believe that. I've had people buy me that mug before. I mean, we've been a huge partner to St Jude Children's Research Hospital. We're partnered with Ben and Candy Carson right now. We're building reading rooms across the country. Like I've almost been. When I create a new venture, I'm almost like, okay, well, who do we get to help?
B
What's.
A
What's. You know, what's the purpose for it? Because that's where I get really lit up. And I've learned that I care almost as much about what it means as to what. As what it makes, which is why I need good finance people around me.
B
Absolutely. Because then you can give it all away. I think that my journey is probably similar to a lot of people's in that I started off, I didn't care about money. Money wasn't the driving force. It was. I wanted to create change. I wanted to. I really love disruption. I loved thinking outside the box, doing something no one has ever done before. Like, it. I have this very, like, exploratory nature where I just want to do different things, you know, and boredom sets in, doing the same thing over and over again. So I think that was the path. But then it was like, once I got to the top of that path, I realized, like, oh, there's no satisfaction or fulfillment here. So another house, another dollar, another trip, another. Whatever it was, other company. It was just, you know, you climb Mount Everest and realize, like, oh, wait a minute, there's another mountain over here that's taller. Like, I should go pursue that one. And it was that rat race of just over and over and over again. I think, that brought dissatisfaction. That really caused some introspection to say, like, why do I. Why do I have such success on the outside and feel so unsuccessful on the inside? That's when I turned to what actually lights me up. Like, what actually. What do I. There's gotta be something bigger in this, you know, like, this experience, this human experience, than just what I have. And so that was the journey. Then it was okay. Now it's exploration, and, you know, it goes hand in hand with a lot of that introspection I've been doing, which is, you know, I've had the nonprofit since 2013, so I started it long before I ever knew I needed it, But I was just doing it to do it, you know? Like, I almost felt like it was what you do, you know, you build a business, you give some away. Well, I might as well control what I'm giving away. So I'm going to start this nonprofit over here. Then as I sold all the companies I had the Big X in 2019, sold 76 companies in one year, and I'm borderline depressed now. My identity's gone. I don't have a reason why I have to get up in the morning, you know, like, it's just like, oh, man. And it all hit me. And that's when I just said, I got to figure this thing out. And so while I had the nonprofit, I really wasn't giving myself to it. Then I decided, I'm Just going to explore this and then started feeling just like amazing, you know, like my life changed when I really gave myself to it. And I think that it's tied a lot to our subconscious, it's tied to our upbringings. You know, I had a brother, my brother that passed away was. Ended up being special needs before he passed away, kind of had a normal younger years and then progressed and just like digressed towards death and passed away when he was 18. But what I saw was the whole world accept him as a little boy and then not accept him when he was sitting in a wheelchair and my parents had to take care of him. So I saw in my mind, I saw just like society reject someone to me who was so pure and so loved and so amazing. And I watched all of the world around look at him negatively and stuff like that. So when I started diving in to represent kids that, that if I didn't show up, the whole world looked down at then it was like there's a sense of just like my past, it was tied to my present. And all of a sudden representing these children that have no representation, the kids, you know, the street kids in India or wherever we serve, you know, that no one is going to care for them. All of a sudden I started feeling fulfillment and things that I'd never felt before. And it was that joy and that happiness that then I wanted more of. That was like, wow, I can't get enough of this. And then I just, then I kind of went back into what makes me successful and I just decided that, you know, I, I had a skill set, I had a gift that I could build, take businesses, see things that others couldn't. I could, you know, create and operate these in a way that most won't or, or choose not to. And, and, and I can give it all away. You know, it's like I can just choose to go make impact on the world. So that's kind of the path. And you know, I get the chance to speak a lot. And a lot of young guys, whatever they're chasing, you know, like they're young entrepreneurs, they think it's the Lambo or the Jet or whatever. And I tell them, you know, I, I actually don't give them a hard time about it. I say, look, if, if what you think is success is a Jet or a Lambo, go find a way to get it. Like, go and get there fast. You know, like, you know, sacrifice what you got to sacrifice, do what you got to do, go get it, because what you're going to do is you're gonna stand next to that jet one day taking a selfie, and realize, man, this thing does not, not make me happy at all. And you're gonna be in the same boat I am. I ended up being in, like, I don't know that I get to where I am today if I don't have the exits, you know, it's like, I think I would have always been chasing. And so I just kind of like, tell them, like, set the goal, go get it. And then you'll realize that, you know, that's, that's not where fulfillment lies. And then real purpose begins to set in.
A
And that's why so many billionaires are on the. Is it the giving pledge? I mean, I think 75% of the world's, you know, billionaires have already signed up and said, we're going to give away 90% of what we got. I heard Bill Gates one time say, I'm not going to give my kids more than $10 million. That was pre inflation, right? But, but he said, I'm not going to give them enough to. I want to give him enough to do something, but not enough to do nothing. And so, like, I sold my company. I've sold, I don't know, 10 things, right? But one was much bigger than all the others. And, you know, I was 50, I'm 57 now. And it's like, okay, well, why, you know, what if I'm, you know, you know, the trusts are full, everybody's fine. You know, we. Everything's. Everything is where you planned it should be. And then, and then to your point, pressure keeps you grounded. It's the downward pressure of the demands of the people that rely on you. The downward pressure of the business. And in one day, with one phone call sitting around our kitchen table, 27 bankers and lawyers are signed off on a deal. It's January 1st. You hang up the phone and they're like, is it over? And I'm like, I don't know, I'll check the bank tomorrow. Yeah, but it, but at that point, I had nothing that I had to do. Literally. It was 25 years of business building pressure lifted off my shoulders all at once. And I think people underappreciate how they. That's a real first world problem, Eddie. But, you know, it's. But I mean, people appreciate, like, how difficult that is for some people to go through.
B
Yeah, it's very difficult. I've been to so many founder groups that, that, you know, of guys that have exited, and so many of them deal with Depression and alcoholism and drug abuse and it's just like, because they're, it's like, like you said, it's like all of that pressure kept them grounded. Then they, it was all taken away and oftentimes their full identity was removed from them. And it's like, and now what? You know, and they think that, you know, they've, it's just, it's, it's a difficult path. Like, and I know that like you said, first world problems, you know, it's like. But there's a reality to this. I mean there's a, there's an issue that most people face when they're separated from the thing that identifies them as successful.
A
Yeah, I, and what kind of got me really back into the game to, to come back and operate? I was investing, I was advising, but I mean it was just kind of the state of the country in the 2020 and you know, 2019, 2020, 2021, we had a lot of divisiveness that we hadn't had before. And look, our, our middle market creates 90% of the jobs and, and families. Economic freedom and financial security on Main Street USA is the most important thing that we can have to keep people safe. And when you lose your middle class, man, and you know, you're Venezuela now, so I had a particular skill set, I mean I had an entire system to build franchise brands from nothing to something. And why would I take that away and go to a boat or into a golf course and tell like I just couldn't, I couldn't fathom not serving the country in that way. And also too then you know, there is no outcome without income. And if I wanted to be purpose driven, then the more that I could make, the more that I could, I could leverage to create some change in the world. So I'm very happy today with what I'm doing. You know, I had 60. You know, you've got a few more years I guess to get to 60. But you know, I'm looking, I'm staring right at it. I mean I'm like, like I'm in turn one and this race is going to be over in three more turns for me.
B
Yeah.
A
You know, I've got to figure out what's next after that. So. But, but look, the closer you get to it, you still feel young, you still feel like a kid and all of that. So no awesome. Why I'm interested to you. So I've always had my charities, have always been around children. So first of all, well, I sold a bunch of my direct businesses in 2006, 7 and 8 to commit to the franchise model. And I came off the road because history was repeating myself. We were all over the world doing restoration, remediation work, Caribbean, all over the place. And I was, wasn't home. I had the three young children at the time. So when I came off the road I, I coached 30 seasons of my kids sports. I was building this national franchise brand at the same time people were coming to me and, and it was a really good fit. And then we connected with St. Jude Children's Research Hospital because I believe and we today build reading rooms with Carson Scholars Fund because to me it's all about the children. Like these are the, you know, the manufacturing, right? The earlier you can fix a defect in the manufacturing process, the cheaper it'll be. So you know, really investing into these, you know, 6, 7, 8, 9, 10, 11, 12 year olds has always been a real passion for mine. Why did you pick children to educate and to feed?
B
I think it goes back to that, the loss of my brother and really it's, it's more about just representing these kids that don't have representation. Like I just, it does my heart good to know that if I show up, you know, that these kids eat, they have a fighting chance at future, at a future. And it's like, and it's just, it's just where my joy comes from. And you know, we go to a lot of places in the world where you know, like for instance one of the ones I'll be in India in next weekend and we have a, an orphanage that is just made of in India. They still have leper colonies right where their parents are losing fingers and noses and ears and there's still leprosy in the world. But they'll once they contract it because that's a caste system, a caste based system. They're outcast like so now they have to live in leper colonies. Well, these kids don't have the disease but they're sent out into the community to beg for their, for their leper colony. Well, most of these, you know, life expectancy of these parents are short and so the kids are left, you know, orphans. So we. But then also because now they've lived in a leper colony, they're still in that lowest caste system. So there's no pathway back in. They'll always have, they'll always be street children. And so when we started doing that there and knowing that I could not just change their experience, their life, but generationally their children's lives and their Grandchildren's lives. You know, it's like if we don't show up, these kids don't ever get a chance at college or get a chance. Like they'll forever be beggars and they'll forever have that path. And so, you know, for me it's, it's that I think that it's the, there's a genesis there in that we really do four things that impact others. We have feeding centers and orphanages. And then those we kind of separate. Like we go into really underprivileged areas and educate and feed. Then we have orphans, we maintain orphanages. Then we dig clean water. We have a lot of clean water projects. We'll do 100, 150 clean water projects in various places in the world just because it's a need that's constantly present and we see the issues there every, everywhere we go. And then lastly, we build sustainable businesses. I take the gifts that I've been given and I build sustainable businesses. And I don't do it like a model where I expect something in return. It's not like a micro funding model or micro lending model. It really is. I'll help you build this taxi company, but you forever will give 10% back to this ecosystem. And I'll do it with the kids that grow up through our system. And so we teach them business, we teach them ethics, we teach them all these things, then we'll fund them. And I think we're up to 27 or 29 businesses that are then creating sustainable ecosystems. And so in Guadalajara, Mexico, which is probably our biggest site by children, we have a few feeding or we have an orphanage, we have three orphanages there. But we also have a sewing center and we have a construction company, we have a coffee business, we have a cleaning company. It's like. So it's like. And then I funded a bunch of their little startup businesses and stuff like that. And so I want to create a full ecosystem in that. But it has always started with the.
A
Children helping people, helping families, help themselves. Yeah, just awesome.
B
Yeah, it doesn't get much better.
A
No, it really, it really doesn't. Oh man. So much good stuff here. Personal brand, it's not something you've always done. Why did you choose to start to build authority? And how comfort, how's it going? How do you like it? And what advice would you give for people or experience advice? What experience would you share with people who have businesses and are not currently making themselves the face of it?
B
Yeah, it's a, it's a two edged sword. For sure. I really didn't start building my personal brand until three years ago. I had already had all the exits, and I really felt like everything I did not want was on the other side of exposure. And I was sitting in a meeting. My business partner and I were down in Florida talking to Grant Cardone, who. He's got a bunch of business, you know, like, he's got all the companies and he travels and stuff like that. And he. He. We were sitting in his office and he looked at me and he said, why don't I know you? And I said, you know me. I'm sitting right here. And he said, no. Like, no, you know you. I don't even know your. He's like, I know you've had a billion dollar worth of exits. He said, but I don't even know you. And I said, perfect. Just like I said to you earlier, like, great. That's. That's a good thing for me, you know? And he said, no, you're missing something. He said, everything you want is on the other side of exposure. And I said, now I feel the exact opposite. He said, let me ask you this. He said, do you want to hire better people? I was like, well, of course. And he said, well, I got a line out my door because of the exposure I have of 30 people that are begging to work for me today. He said, do you ever want more capital? I said, well, yeah, I mean, sure. I mean, maybe. I don't know. I said, maybe there's a day where I need more capital. And he's like, well, capital knocks down my door every day because they know who I am. He said, do you want to make greater impact in the world? And I was like, like, absolutely. He was like, well, he said, the more unknown you are, the more doors it's going to open for you. And he just kind of went down this path. And I was like, I don't know. So I decided to just kind of put my toe in the water and see how it goes. And I started speaking out, you know, started talking about the exits I had. And it went well for a while. And then we created the Aspire Tour. And the Aspire Tour right now is one of the nation's largest business tours. And that's why I speak on that every month. And it's. It's three, four, five thousand people a month. And it's. It's interesting. I think he was right. There's an entire group of issues that I didn't know would come with it. Oh, that I don't necessarily care for, but I think the good way outweighs the bad. And then now when it comes to all my businesses and AI and all the development that we're doing, you know, with a lot of these AI platforms, it's like your personal brand cuts through a lot of the noise that your business brand will be hidden in. And especially when it comes to AI and how these, you know, kind of AI platforms work. It's like it attaches to the personality so much easier and there's credibility in the personality that if you search for my companies or my companies are never going to be referenced in AI, but I get referenced all the time and cited in what I do. And so it's, I think it's a necessary evil. I, if I, if I could have the same success I have and get all the things that I get today because of my personal brand, without having a personal brand, I would 100% do it. Like, I'm the type of guy that would much rather live in anonymity than live on a platform. However, it is something that I think in this day and age is completely necessary. It's, it's, it's very important and it's advantageous. And I think that it's just something that you have to embrace. And I think it's, like I said, it's a necessary evil 100%.
A
Especially as these agentic engine optimization opportunities come up. If you look at all the citations and all the footnotes, they're plowing right past the company websites and they're like, yeah, but who, what is saying it? Why, why should we believe it? And these large language models create incredible bias. So we're almost at this gold rush of authority. I mean, there's a spot to take as the king of franchising. And I'm trying to take it. And you know, we're having great success with it. And you know, what does that get you? Well, maybe it gets you a deal. Maybe it gets you that great employee. Maybe it gets us some franchise deals, people coming in to join and build incredible businesses inside of our brands. But, and I went kicking and screaming. I mean, I'm an, I'm an introvert, a hundred percent. And you know, I like, I like a nice, close group of people. I like to go to war with people. I like to, you know, that's just. But at the end of the day, you know, there's a responsibility to the brands that you've got to go up and you can have the greatest business in the world. And if nobody, nobody knows about it, then really, what's the point?
B
Yeah. And exposure is so important in today's business model. It's like, you know, we measure everything in cac, your customer acquisition costs. And it's like, and just by sheer, the sheer nature of your voice cutting through the noise, it reduces the ability to gain customers. And it doesn't matter if you've got a sandwich shop or a coffee company or you're selling insurance. It's just, it's the nature of the, of the beast today.
A
Yeah. Before, you really personally didn't have the opportunity to break the tie. Now you can.
B
Yeah, you can, you can.
A
One short form Mid Video can break the tie on a $5 million account for one of your companies.
B
For sure.
A
Yeah, Eddie's going to be here. You might get to meet him. Oh, oh, okay. We'll come for the meeting.
B
Right, Right.
A
So that's awesome. Do you sprinkle in personal stuff or do you keep it pretty?
B
I tried. I mean, I have a brand consultant who, you know, pushes me a lot harder than I want to be pushed on the personal stuff. You put me in front of a whiteboard and let me teach business, I'll do that all day long. But it's like if you want to, you know, sit there and ask me questions in my car about personal things and, and I, you know, and I resist the. I really, you know, I'm super blessed. I have all the toys and I have an amazing life, but I really don't want, like, it's so disingenuous to who I am. Like, I feel so much better about the orphans I'm serving than about the cars in my garage. And so, yeah, I'll, you know, they push me hard on lifestyle stuff because it's like they feel like the audience attaches to some of that. And so I'll allow it a little bit here and there, but, but I always find myself going back through my Instagram account and archiving stuff. If they put too much of it in there, you know, it's just like, ah, that's enough, you know.
A
Yeah, we got a, we have a 19 year old that swings through here with her tick tock phone ready to go. And I'll give her, I'll give her 30 minutes and you know, do this, do the thing right. But that's, every platform's a little bit tick tock. I mean, it's, you gotta, you gotta do the thing. I mean, it's creamy or crunchy. What do you want? Do you have a dog?
B
I do not have A dog.
A
Oh, wow. That's. See, that's how I get out of it.
B
Yeah.
A
I post picture of my dog.
B
There you go.
A
You know, hanging Christmas lights.
B
There you go.
A
Did that yesterday. Awesome. Well, you know, Eddie, I'm honored that you spent this time with me today.
B
Yeah. Glad to be here.
A
Yeah. I've really enjoyed talking to you. I've got a curveball and a fastball for you, straight down the middle. You feel like playing?
B
Let's play.
A
All right. You want to tell people how to find you or direct them to the Empire operating system or anything else before.
B
We do that, I think that I really do enjoy interacting with people. And so I've been answering my own DMs for about a year now, and. Which has been a interesting thing. And so, yeah, Eddie Wilson, official. Anyone has questions or needs help, I'm happy to engage.
A
And Aspire Tour is every month. On the month.
B
Every month on the month. We have a full. We'll slow down a little bit next year in 2026, and we're only going to do six events, so we'll go to every other month. But we. Three years in a row, sellouts for three years every single month. Everything from Madison Square Garden to small, you know, thousand person events in Columbus, Ohio, you know, so we've been all.
A
Over the place just crushing, crushing speakers and personalities in that deal. Just unbelievable. Anybody who you want to listen to, you can find at the. Get inspired at Aspire and join. Join the Mastermind. It's the biggest in the world. Awesome. All right, curveball, here we go. And this is a statement of market opportunity. Gun to your head. You're forced to start a business in the next 30 days. For you, probably not a problem. And it can't currently be a business that you're in.
B
Okay.
A
So where do you see the opportunity in the market? You have to. You're forced to start a business in the next 30 days. What are you going to do?
B
I'm going to go into financial services of some kind. I'm going to. Right now. There's so much opportunity with disruption and AI for financial services to provide a faster, quicker, cheaper solution. That's what I'm standing up in. In 30 days.
A
Yeah. There should be no reason that we have to do our own accounting anymore. That is the most black and white thing. And yet we've got people like, like elves cobbling away on these financial statements and, you know, putting receipts in. Yeah. Shouldn't be a thing.
B
Shouldn't be a thing.
A
Awesome. All right, last question. Right down the middle. If you had one sentence to make an impact in somebody's life, what would that be?
B
It would truly be to focus on what God given abilities you possess and then allow that to be brought into the world. That's my one sentence. Because in doing so, it's like you have fulfillment and you make massive impact.
A
Awesome. Perfectly said. Eddie, man, thanks for being on today.
B
Thank you. Appreciate it. Thanks for having me on the show.
A
Awesome. Awesome. I'm Jeff Duden here with Eddie Wilson and we have been on the unemployable podcast. Thanks for listening.
Unemployable with Jeff Dudan, Episode #236
Title: You Sold the Company… Now What? The King of Exits: Eddie Wilson on Life After the Exit
Release Date: December 16, 2025
Host: Jeff Dudan
Guest: Eddie Wilson (“The King of Exits,” serial entrepreneur, founder of Empire Operating System, philanthropist)
In this episode, host Jeff Dudan welcomes Eddie Wilson—a prolific entrepreneur known for having built, bought, and sold more than 120 companies, and creator of the Empire Operating System. Wilson is celebrated for his massive business exits, his unique philosophy of acquiring and scaling companies, and his deep commitment to impact through philanthropic work feeding and educating children globally. The discussion centers on what happens after a large business exit, lessons learned from both entrepreneurship and philanthropy, the transition through critical roles in business growth, and the keys to finding purpose after financial success.
On Founders as Bottlenecks:
“The hero… ends up turning into the person that gets assassinated. So many heroes in that founding position five years down the road are getting assassinated by their CFO because they won’t let go, rely on others’ strength.” — Eddie (07:35)
On Buying Successful Companies:
“I think you should buy people’s successes, not their mistakes… Why bet on something going wrong when you can accentuate what’s going right?” — Eddie (11:39)
On Philanthropy and Fulfillment:
“I realized, why do I have such success on the outside and feel so unsuccessful on the inside? …Representing these children that have no representation, I started feeling fulfillment and things I’d never felt before.” — Eddie (37:15)
On Personal Branding:
“If I could have the same success I have without having a personal brand, I 100% would… But it’s a necessary evil in today’s business.” — Eddie (51:19)
On Lessons from Mother:
“Gratitude in the valley… is a catalyst for your greatest growth. Most people create limitations when they’re in the valley.” — Eddie (28:16)
Eddie’s Next Business Idea (57:20):
“I’m going into financial services. There’s so much opportunity for disruption and AI to provide faster, quicker, cheaper solutions.”
Eddie’s One-Sentence Impact Advice (58:02): “Focus on what God-given abilities you possess, and allow that to be brought into the world… you have fulfillment and you make massive impact.”
Find Eddie Wilson:
The Aspire Tour:
If you’re an entrepreneur on the path to a big exit—or wrestling with “what’s next”—this episode is packed with hard-won wisdom from a true king of exits. Eddie Wilson delivers candid, actionable insights on scaling, delegating, and leaving a legacy through both business and impact. The dialogue is sincere, practical, and unfiltered—perfect for founders, acquisition-minded business owners, and anyone seeking purpose beyond success.