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Scott Clary
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Eddie Wilson
With Belay, I was young. I was going to have to front all this capital. Realized like very quickly that I was at the table with somebody. I didn't understand who they were. I was up against it. I had already booked all the ads. In the end they gave me seven times ebitda, which is great. Had I been able to book all the revenue in the next 90 days, that would have been $30 million more.
Scott Clary
He isn't just an entrepreneur. He's known as the king of exits. Eddie Wilson has owned and exited over 100 companies that totaled more than $1 billion in exits, earning him that legendary title in the entrepreneurial world.
Eddie Wilson
So many entrepreneurs, the bad thing happens to them now classify. This is who they are. I look at most of the businesses I buy and think, man, that guy's a better operator than me. That guy had more vision than I have. But I believe that I can do something with it that they can't. And that changes everything.
Scott Clary
He's the creator of the Empire operating system, a framework used to scale and manage businesses with precision and purpose. And through his nonprofit impact others, he's feeding children, empowering communities, and creating sustainable change across dozens of countries.
Eddie Wilson
You're not going to truly scale a company when it's based on one person. If you're going to truly build community, you cannot think monetization first. Community has to be community first. Success takes time. Every poor choice I made along the entrepreneurial journey is I made it because I believed I didn't have time. When I'm young, time is my ally. When I'm old, time is my enemy.
Scott Clary
Take me back to that first exit you had at 24. I want people to understand sort of where you came from, how you got into this game of exit, of acquisition, of buying, selling companies. But the first real notable thing that happened in your sort of entrepreneurial life was that exit at 24 when you learned the game, but you got taken for 30 million. So walk me through what happened.
Eddie Wilson
It was an ad agency that I had built from scratch. I was sole owner of it and was sourcing capital. And so, you know, in the ad space when you were, you know, I was booking ads for Subway and Buffalo Wild Wings and all that stuff. And you have to carry that ad spend typically for 60, 90 days. So you get these big contracts. And I was young, I was in my 20s. I didn't know I was gonna have to front all this capital. So I started going after capital. And, and so I'm sitting at a table thinking about the close on sourcing of capital so that I could carry this ad spend for the next, you know, 60, 90 days and, and realized like very quickly that I was at the table with somebody that I didn't understand who they were. So my M and A attorney was trying to source capital, but really did not vet these, this group well. So I'm sitting across the table from three or four just sharks, you know, and I'm young and they're looking at, they're very calm. And then the one guy says, hey, today's not going to go like you think it's going to go. And I was up against it. I had already booked all the ads, the, you know, ads running all across this southeastern part of the country. I've booked, you know, $20 million worth.
Scott Clary
Of ads banking on this capital, banking.
Eddie Wilson
On that capital, on everything. Beg, borrowing, stealing whatever I could. And they had promised me a close about 10 days before that, delayed it. So I'm just thinking, oh, they're going to delay. And I just, I had a deadline and the deadline was like two to three days later. And so I'm stressed, you know, in my 20s. And he, I said, okay, well how long is going to take you to get the capital? He said, no, we're going to buy your company today. We're not giving you capital. And I was like, what? Like, it just caught me so off guard. And I'm looking at my guy thinking, you know, like, what's going on? And so he said, he said, we're going to buy your company today. He said, we're going to be fair. He said, but the reality of it is, he said, you took something that was ours. He said, do you know who we are? And I said, I have no clue who you are. And I said, you know, do you know who they are? And he was like, well, whatever capital source. And they said, we're the largest ad agency in the world. They said, you basically stole these clients off of us and today we're going to get them back. And they're like, we're going to be fair with you. So in the end, what happened was they gave me seven times ebitda, which is great in the ad space, I could have held out for more. But it was that I was on this massive trajectory and had I been able to book all the revenue that I made in the next 90 days, that seven times would have, would have been $30 million more. And so like that, that's where they, they knew what they were doing.
Scott Clary
And so they knew that you were over leveraged.
Eddie Wilson
Oh, 100%. I mean, because I had to disclose everything to them because they came in as a lender, they came in as a debt structure and they were going to, you know, give me money and I had to show them my contracts. I mean, I showed them everything, you know, like open kimono and just had no clue who they were. And that day I made a couple of promises to myself. And the first promise I made, first of all, they gave me 24 hours and they said, you'll sign tomorrow or we're walking away. And we know what that means for you. And it's going to implode.
Scott Clary
We're going to get our clients back.
Eddie Wilson
We're going to get them all back. Yeah. And they said 24 hours. So I'm ticked. I mean, I'm, I'm going to call my lawyers, I'm going to blow whatever. Like, I just, I was, you know, I had no recourse at all. I get home, I'm frustrated. My, my mom always taught me I went through a lot of loss in my early life. Lost my sister, lost my brother. And my mom would always like, make me rehearse gratitude. She would be like, Eddie, if you'll rehearse gratitude in any situation, you'll end up getting the bonus of whatever problems come in your life. You know, like, you'll find the mountaintop versus being. It's like so many entrepreneurs, the bad thing happens to them and it now classify. It's like, now this is who they are. And my mom teaching me just to rehearse gratitude. So I'm in the, I'm coming back in the morning to back downtown Chicago and I'm like, okay, what, what good could come out of this? You know? And it dawns on me, I was like, you know, okay. So I'm thinking through the exit and it's like, okay, they're going to give me seven times ebitda. Well, ebitda, essentially, you just look at his net. It's like I would have to do the same thing for the next seven years and get the same result, change nothing. And they're essentially gonna give me seven years of my life back. And so like, it dawns on me like, wait a minute, like, this actually isn't a bad deal. Like, obviously I'm giving up, you know, my mind. 30 million, 25. 30 million. But I also was getting seven years of my life back and getting it today. And they were willing to pay me capital, like cash within the next 30 days. So I get to that place, I'm like, okay, well this isn't that bad. Like, what would I do if I had seven years of my life back? Like, where would I go? And so like I'm, I'm, you know, 40 minute drive back into Chicago. So I get there and I sit down at the table, I'm smiling at them and they're looking at me like, what? You know, what's up with you? You know, And I had that thought in my head and I made two promises that day. The first thought I had was, I'm gonna get this Capital and I'm gonna go do something with it. I don't know what I'm gonna do with it yet. But I'm never gonna treat somebody like they treated me. But also I felt like I just unlocked something. Like if I could sell something on a multiple and I'm a real, I'm third generation real estate investor. So I was like, I, I don't get a multiple like that in real estate. You know, like I don't get projected revenue and then paid on it. You know, it's like there's no speculative revenue sources and real estate, I mean there's some. But not degree not, not no. And so I was like, man, this is different. And I started thinking, well, number one, I'm not going to do what they've done. I'm never, never going to take advantage of somebody like this. And number two, I'm going to learn this game. Like, obviously I am outmatched, outplayed. I had no idea they had to explain to me what EIDA was. And so like I, I was like, what Exactly. I'm like talking to my guy. First of all, I was just ticked off at him.
Scott Clary
Probably fire him first.
Eddie Wilson
Oh yeah, like, how do you know? You know, I was like, you're not getting your commission on this deal. But anyway, so we, we kind of get. He's like, he writes it down on a piece of paper. Earnings for interest, taxes. Like he. And I'm like, is this like kind of our net? So it's my net. And he's like, well, it's probably a little bit more than your net. I'm like, okay. Like I had no clue. You know, there was no chat GPT for me to like sit there and act like I knew what I was talking about.
Scott Clary
But I think that, you know, one thing that I fully, fully believe is in that moment, fortunately you had like a really healthy relationship with your identity and you understood what gratitude was. I think that in that moment somebody could have taken that away and it could completely demoralize them and killed. Even if they took the deal, they would have felt like they were like screwed over. They would have felt like they were taken advantage of. It's like, oh, you know, the world's out to get me. I work so hard. All this bad luck and then it like reframes your relationship 100% with entrepreneurship, with building a business and then you just self sabotage.
Eddie Wilson
Totally.
Scott Clary
And, and this was on the other side of getting cash too. I think this, I think to be quite. Most entrepreneurs screw themselves because they Something bad happens and they're not getting cash. And they also self sabotage for sure.
Eddie Wilson
It, it seats in your, in your subconscious. And it's like now, in order to keep you safe, your subconscious is okay, there's a marker. Don't ever go back past that point again. And then they do, they self sabotage. I've had so many business partners later in life that I've bought a business off of or I'm, I've bought it and I'm still hold them in an operator seat and you just watch them do crazy things. And it always stems back to, well, this failure that happened now is their ceiling, you know. And little did I know that little tip of my mom saying, you know, like, find gratitude even like I, I lost my sister when I was 6 and my mom, I would struggle with it. My mom would say things like, Eddie, instead of thinking about how much you miss her, think about, let's think about what was her favorite toy that she played with. What would you like? It was like a mom that was just so emotionally intelligent to help me process those things that gave me this crazy tool later in life that I, I easily could have been the guy that got ripped off for 30 million. I could, you know, like, I could have been sitting here talking about, you know, this horrible experience in my life. It's like, but it wasn't that at all. You know, it's like, and then through that gratitude then I made these commitments and then those commitments carried me past that point immediately. It's like I, I remember going home and thinking I, I literally was searching online, going, how do you find out about private equity and acquisitions and roll ups like that? I mean I'm, a day later, I'm like figuring it out, you know, versus sulking and you know, being frustrated. And I made my first acquisition within a year of that moment. So it's like I, I wasn't slowing down, there was no downtime.
Scott Clary
But you, I mean like now you see it at scale because you work with so many different CEOs and I'm assuming that some of the CEOs where you are not all the businesses that you acquire are distressed. But I'm sure when you do see some distressed businesses, this is the reason why, like they, they are a mindset away from taking action or doing something that could radically change the outcome, but they're over it. They think that there's no out, there's no positive out. And they're like, okay, I just have to get rid of this.
Eddie Wilson
I, I typically my strategy is Usually not buying distressed. I, I always say I'd rather buy somebody's success than their problems. Um, but I will tell you that even in their success, they've gotten to a place where they feel like they can't, they can't get more out of the business. They can't take it to the next level. Like they, they could be making a million, 2 million, $3 million a year profit to themselves and still believe that they have no path to get to 10. You know, it's like, it's just, it's a wild thing, but it usually.
Scott Clary
Why do you think they have that limiting belief?
Eddie Wilson
It's a, it's a weird marker that gets, gets set in the mind of an entrepreneur. It's like they hit something, they hit some wall. It's. And it's 100% mindset. It's 100% mindset. Most of them have such a, like, I look at most of the businesses I buy and think, man, that guy's a better operator than me. That guy had more vision than I have that guy. It's just. But I believe that I can do something with it that they can't. And that changes everything.
Scott Clary
Your first acquisition was a year later.
Eddie Wilson
Yeah.
Scott Clary
How did you figure out, you know, the, the art of acquisition, the art of figure of buying of. And was it an individual acquisition or were you thinking like roll up or you like, what was your thought process when you were getting into private equity?
Eddie Wilson
Having a conversation with my grand, who said, if you ever get the chance to like get involved in insurance, he was like, it's a century old game. There's not a lot of new information. He was like, there's some disruptions that are happening. He was like, if you ever get captives. He's like, he's like, it's, it's kind of this pre. He was like, think about all these actuarial scientists that determine the success of this thing. He's like, you should invest in insurance. So I got a buddy of mine had an insurance company who's looking for some capital and I was just going to be passive and so I went in and I was looking at his deal and it was a group of guys and they had 20, 30 companies and they had rolled up a bunch of stuff and they came in and they were like, hey, we don't have an operator. They're like, what would you consider. So after a month or so talking there, I was going to make the acquisition or at least be a passive investor in the insurance company. They're like, would you actually be okay with us giving you matching the equity in this insurance group with all these companies over here, and we'll match it, but the only caveat is you have to come in and run them. And I was like, well, I would consider it. And so I took the next five years and I essentially took that group of. Yeah, there was like 24, 25 companies, something like that. Very small stuff, like the insurance company was the prize possession. And then there's a bunch of little random tech companies and some technology stuff and, you know, things that complemented insurance. And then I ended up going in to run that. And then because of that, it gave me the ability to go buy because now I had this group of companies leveraged things I could add things to. So it was like it gave me this master course immediately, within the first, like year. So really what I do is master operations among many assets. Once I mastered that, then we went to 76 companies. We sold, you know, I had a big exit in 2019 and sold, you know, 76 of those assets. And so it really was an investment that turned into a lot of operational kind of prowess and understanding. Then I was like, oh, and those guys wanted to add more to their portfolio. So then they had deeper pockets. I had capital. It was just the perfect storm.
Scott Clary
Do you feel like this is interesting? Because I always see. I always see great operators, in some cases have a hard time becoming good investors. They do. What allowed you to become a good investor aft. And I do think that to become a good investor, you do have to be a good operator first. You actually know how things run and you know how to hire good talent and whatever. But what allowed you to sort of do both things simultaneously? Because that seems to be a rare skill because I have some friends that have had massive exits that lose a ton of money trying to figure out how to invest.
Eddie Wilson
Yeah. And that is the case. I have a buddy in New York right now that had a huge exit and calls me non stop with the most absurd ideas. And you're like, what are you doing? You know, like, why would you. He's so far outside of his lane.
Scott Clary
But he's so good at what he did.
Eddie Wilson
Yeah, he's amazing at what he did. Yeah, I think that what hap again, I think it was serendipitous or maybe it was divine, I don't know. But it was like, I think that going in and because they had. There were too many companies for me to operate right off the bat, I had to then build my empire by building the people When I was building the agency, I was outselling, I was doing everything. I had a media background. So it's like I could speak to the, the technology that we were using. I spoke the language. So it was like my insurance or my, my advertising agency was really based on me. And this now was too big to be based on me. So then I had to attach to these leaders. And really what happened was, is. And I realized very quickly I can't run all of this. I have to, I have to put myself into this seat that I'm good at. And, and then I really just, I was forced into building people. Then I really focused on how do I build these people. Then as I built the people then I saw this theme was like, oh, that guy is a great operator. And that guy's great upper, that lady's, you know, crushing. And it's like. So then when I would acquire the company, I would essentially create a bench of people to essentially operate.
Scott Clary
You were forced to do it?
Eddie Wilson
I was forced to.
Scott Clary
What size company do you acquire now? Do you see that great operators still have that problem hiring great people every day because they weren't forced to figure.
Eddie Wilson
It out every day? And so what happens is, is most investors, or let's just say somebody who exits a company, they exit for a sizable amount, you know, revenue capital covers sins. And it's like. And so what happens is it allows them to make bad choices. Usually the best operators are the people who run low margin businesses or they've been forced to because they've been under the gun or they don't have capital. It's like they're the best operators, you know, but they also then ceiling out because they learn really bad lessons in that journey. And then they can't get to where I was forced to. It's like if you're four stop. I own coffee companies, coffee shops. We have a coffee roastery and lots of shops. And we're expanding super low margin in order to run a coffee shop. It's a different mindset to run than to run the coffee organization. And, and it's just like there's steps to that game and people get stuck. But the nice thing is, is I was forced. I didn't have a choice. It was either sink or swim. It was sink or swim when I was building my business and it was sink or swim when I was at the private equity side. It was like there was just like this constant push. And so there was no way to just let my capital kind of COVID the bad choices I was making. And that's where a lot of people that exit, that's where they literally throw money at things to see if they know what they're doing and then they find out they don't.
Scott Clary
I also feel like founders can be incredibly effective to a significant degree. Like, I mean like they can grow a company significantly and bring in sometimes tens of millions of dollars in revenue while still having a massive key man problem in the company. 100 which blows my mind. And I'm sure again you, this is probably what you see with a lot of companies you acquire too. Because yes, there's the mindset of can I take this company from 10 million to 50 million or I don't know what your buy box is but say that's one of them, right? Like somebody who's stuck at 10 million and they're taking home some good money at the end of the day. But is it, can I do it? Like do I believe in myself to do it, but also do I know how to hire the people that will take it there with me? And you can be a. There was a company that I worked for when I first started my career and the, the company was doing around $11 million in revenue and half of that was coming from founder led sales. It was just his relationships.
Eddie Wilson
It's pretty typical, which is crazy. It is crazy. And that's. We always say there's really five phases of business, right? Like you have startup, then you have perseverance. That's kind of your pre profit phase. Then viability. Viability, you really don't truly reach viability. You could be a $10 million in sales and not be a viable company because you have a single point of failure. That single point of failure can be a really charismatic leader who can go sell $10 million worth of product, you know, or services. And so then you get to scale. You rarely go from viability to scale if it's still personality led, you know, it's like you can have the personality led companies but in the end you realize like there's a lot more to this, you know, like they're using it as, you know, whatever, lead sourcing or something like that. But it's like, you know, you're not going to truly scale a company when you're, when it's based on one person. One interesting point that you made that I want to you kind of jump onto is like most entrepreneurs, especially the guy that can go out and sell 5, 7, $10 million worth of product, they have a delusion as well that I see a lot and that is when they go to create the team to take that from 10 million to 50. They get so enamored with their own ability. All they do is they go reproduce themselves. And what happens is that next phase is they reproduce their problems at a higher rate than they did their productivity. So it's like the guy that can sell 10 can go hire a guy that can sell 7, but the guy that could sell 10 is barely fulfilling at the level to, to hang on and create that viability. So then they go create this next guy that's going to, you know, maybe do 70% of what they do. And they just maximize their problems. They don't actually maximize their output.
Scott Clary
That's interesting. Okay, so fast forward in your career. You have now how many companies that you're, that you're running. Basically you have like 76. You said you sold, so I sold.
Eddie Wilson
You know, we had 86 total. And then in one calendar year we sold 76.
Scott Clary
Sold 76. So that was what between 2010, 2013.
Eddie Wilson
So 2013, I got involved in that group. 2019 is when we sell all those companies.
Scott Clary
Understood, okay. And thinking about that, that strategy of selling stuff off, what was the reason for the sell off? You just wanted to exit out. You want to do something different.
Eddie Wilson
Like felt like the, there was a lot going on there. That my biggest exit, I still am under NDA and can't even like really talk about it, but that one's like that, that exit really was something that I could not choose. I wasn't the majority owner and so I just was along with the ride. The 76 companies was, there was a little bit of infighting with the ownership group. You know, there's always something. But then also it really was market conditions. 2019, if you like. I, I love following the economy and I'm an investor so first. And so it's like when you follow that kind of conductive wave, the K wave. I knew we were at peak and I'm watching, you know, Warren Buffett selling off and it's like I knew we were at peak. So when we started getting offers from one private equity company was like, well, why not? Let's see how far this can go. And so I had no idea Covid would be the next year. And you know, we had thousands of employees. I had no idea. But it really just felt like the peak of the market and we were getting higher multiple offers than I had ever seen before. I was like, okay, this seems like it's a little bit of a bubble, a little bit in inflated. So we should exercise the. The right to sell. So we sold. And then I ended up, you know, I, I think I ended up during COVID Having maybe 30, 40 employees total from thousands. And like, it was just a. It was a wild decision. That was really the perfect timing.
Scott Clary
How important is timing and everything?
Eddie Wilson
Timing is everything. Most people play. They'll play the games, they'll play the, you know, like, right now it's like I have so many buddies that are like, I'm. I'm rolling out H Vac companies. And I'm like, okay, I get it. Are you looking at market conditions while rolling this up? I get everybody else is doing it, and I get there's plenty of capital and I get that there's private equity everywhere trying to buy these H Vac companies that are $100 million plus. But are you watching the economy right now? Like, are you watching what's going on with AI specific to that industry? And it's like you and most of these investors, they, they get very transactional and especially the institutional level. And they don't play the economy. I play the economy. The economy is like the board I'm playing on and everything else are just pieces, whether it's a multifamily deal or it's a private equity deal. And I'm looking at market condition.
Scott Clary
Do you feel like they're just chasing hype? A lot of investors chase hype, even. Like, I know that it happens like when there's just an individual who's putting a little bit of money into the market and they, you know, institutions bitcoin on the news and they're like, I'm going to. Yeah, but institutions do this as well.
Eddie Wilson
Oh, yeah, by far. And, and what happens is, is there's what, what we have, you know, is like the whales, you got the big, big giant ones. You know, you got the, the multi billion dollar. You know, you got blackrock and Blackstone and, you know, all those. And then, then downstream, you've got midcap. And Mid cap always is watching the large cap stuff. And so to me, I actually don't get lost in the. Right now, Mid cap is so focused on. On aggregating revenue, finding efficiency, selling off within a. That's all they think about. They think about eating the minnow. The minnow turns into the midsize fish, and then they serve it up to the whale. I played that game for a while, and right now there's so much competition in the midcap space. Like people rolling up H Vac companies, people rolling up doctor practices, people Rolling up dental practices like the roll up game is so crazy. But I will tell you that I kind of paused for the last year, year and a half. Like I've, we've made a couple of acquisitions but nothing crazy. But I will tell you that the new tax bill, again I'm playing the economy. So the new tax bill that just came out actually allows 401ks, which is the first time in history to actually be allocated towards private equity funds. So the, you know, $1 trillion that's on the sideway, the sideline in liquidity and PE today is going to turn into 2 trillion probably in the next 18 months. It's like, okay, now they're going to overpay again because they're trying to find yield because all this capital is, you know, flowing in. So again, I'm always playing the market, not the, not the games.
Scott Clary
That's interesting. It's interesting that even at a higher level people, they just succumb to this fear of missing out. Truly. Like, and I, I also think it's because some of these firms, they have mandates to invest.
Eddie Wilson
Yeah, they do.
Scott Clary
And that will screw them over if they're not making. Because like right now you see the conditions, you're not just following the hype, you can take a step back, right. And that, that will allow you to make smarter moves.
Eddie Wilson
I, the, the biggest difference between me and a big fund or even a mid cap fund is I am not raising capital to buy companies. I may raise capital here and there more as a syndication model for specific companies, but I'm not, I don't have a pool of $100 million that I have to give yield to. And it's like they do and so, and they, and then they chase the bigger pool of money that has to give yield and then you, you find these massive breakdowns. But yeah, I, I think that overall private equity took us a slight, you know, hiatus, just like real estate did. I mean it got flat and I think it's going to ramp up for a little while just because there's going to be so much liquidity.
Scott Clary
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Eddie Wilson
Yeah, my theory is, has always been build community first, serve the community by buying companies that serve that community. So it's always been my theory. So, like I have the Aspire tour, it's largest business tour in America right now. We travel every month. And what I'm, what I'm doing is creating community. And so we have masterminds off those communities. And you know, our one mastermind has over 3,000 members. Well, 3,000 small businesses. I can literally say, hey, what are you guys struggling with? Where are you spending your money? Let me see your P. Ls. And what we found was, is tax firms, financial services, bookkeeping, it's what they were all struggling with. So if I can build a viable company there, I've got 3,000 potential clients. You know, it's like, well, you know, you look at Ernst and Young, they've got, however, their market cap is ridiculous and they have less than 5,000 clients. It's like, I know these clients are significantly less, but it's like you look at what they're doing to service them. It's like, could I create a tax room that has 5,000 clients? Like, yeah, I could. Could I have a billion dollar valuation? Yeah, it probably will. You know, it's like, so I create community and need before I go make an acquisition. So I'm not looking at acquisition. My buy box is different because I look at my buy box based on what my community can create in valuation.
Scott Clary
Interesting. And I don't do a lot of firms do this. No, I don't think, because we were talking to you before we press record about sort of how Aspire came to be and it was all from this community play, Build the community first. Right. And we're talking about how it seems like a super high risk bet because that's an expensive community to build. So I don't think any other private equity firms are putting on the largest business conference in America. Right. So it makes a lot of sense.
Eddie Wilson
But if I gave them the metrics and the numbers and I said, hey, is it cost me a million bucks and Aspire, and out of that million, it's going to give me, you know, 3,000 small business leads that now know like and trust you, 10% are going to say, we don't want anything to do with you. And a Good, you know, 75 to 90% are like, what else do you have? Is there's some other way you can serve me? Can I be a part of your community? It's like, and if, then I showed them the lifetime value of that 75 to 90% and they saw the lifetime value versus the million dollar expense, every one of them would be in the live event space.
Scott Clary
But this is how you disrupt an industry. So what, you're disrupting private equity, correct?
Eddie Wilson
Trying, trying. But it's a big space to disrupt.
Scott Clary
It is, but I mean, it's a, it's an innovative way of sourcing customers and, and figuring out what people need. But it's a very smart way. I mean, some of the best businesses I know are community first.
Eddie Wilson
And, and in that community, it's like, you know, we spend a lot on digital ads. Digital ads are great. Our conversions are great. We figured out kind of the digital marketing space. However, when someone comes in, they see you in person, they see you on a stage, they, there, there's, there's a, there's a connectivity. They see you in proximity to all the celebrities that they love and then they hear you speak, like, they hear me speak every Aspire for an hour, like, and it's in person and then they see me in the hallway and then they see my non profit in the hallway and it's like, that's different than hey, come to my webinar for the next 90 minutes. It's like the funnel, it speeds up. It's the same reaction, but it's the reaction time is, is, is, it's a.
Scott Clary
Micro, you can compress it. So when you think about building out Aspire and building out community, how did you do it right? I'm sure there was a lot of that didn't go right. Very stressful.
Eddie Wilson
Yeah, very stressful.
Scott Clary
But how did you do it right? Like, what allowed you to? Because other people try and build communities I don't think I've seen. Honest. I see you everywhere. I see Aspire literally everywhere. So you've done something right. And it's, and it's, and it's still growing and you're still building momentum. So how do you build a community properly? Because I think that's a very useful skill for somebody even if they don't do it at the level you're playing at.
Eddie Wilson
You have to, if you're going to truly build community. You cannot think monetization first. Most people do not put in the time. I guarantee you did not monetize your first podcast. You gave and you gave and you gave and you gave and you gave. And then typically what happens and when it happens correctly is then they ask for something and they're like, oh, now I have the right to monetize. Most people do not have deep enough pockets to do what we do, what we did, and they didn't have enough patience. It's like we. We had so little to sell in the early days, and we sold it for so cheap. Today, we sell it for a lot more because there's a value tied to it that I can prove. But it's like our. Our, like our mastermind. Everything. We. We were a third of what everybody else was. And all we were trying to do was cover our cost. And it was like, we were like, man, if we could buy year two, cover our cost, use it as leverage points to build. Listen to them, tell them. It's like, community. Community has to be community first. And it's like, you can't be community and I monetize first. You know, it's like. Or else all you do is erode the community.
Scott Clary
So you feel like when people try and do this, they get greedy.
Eddie Wilson
I think they get nervous because you have to go in so deep. I think there's a lot of altruistic people that are like, I'm going to build community. And then you do it and you do it and you do it and you do it and you think like, well, man, I'm. I'm in the hole, you know, like, at some point this has to pay me back. And then I think that nervousness and that weight, it's. It's. It's a very patient game.
Scott Clary
I see this with a lot of creators. I mean, I'm in this world now, and people just commit 5, 10 years towards even this podcast. I've committed years of my life to it before it makes a dollar, really. And I think that's the game that, again, you have to be in a good position to be able to do that. Or, or maybe you don't stress yourself when you're first starting. Like, if you want to put on an event, series, whatever, maybe you don't quit your job right away, and maybe you do it as a side hustle so you can still, you know, pay the bills. I think that people, this is. This is not exclusive to community building, but I think people just. We are sold this lie of overnight success. And it's even worse with social media now, and it feels like everyone's getting everything Instantly. And I think that the people that can set proper expectations, can play the long game, can commit to something for five, 10 plus years. Those are the people that end up winning.
Eddie Wilson
You think about it this way. So my story is interesting. I have all these exits, right? And I'm the architect of these exits. I didn't benefit from the billion dollars, but it's like architected over a billion dollars in exits. I had no social presence, and I'm here with a local influencer that everybody would know. And he said, I know you sold all this stuff for a billion. Why don't I know about you? And I was like, I actually feel like I don't want you to know about me. I was like, I like anonymity. I feel like there's a lot of crap that comes with exposure. And he said, I think it's everything you want is on the other side of exposure. And I was like, okay, tell me why. So he started going down that path. He told me, you know, if you ever want to attract capital and attract good talent, you want to try. He was like, I built my entire brand on attracting all this stuff. And I was like, huh? I was like, yeah, I mean, maybe I'll try. And, like, I just want to see how much the negative is going to outweigh the positive. So I started. And this is now. Well, I mean, it was two years for the Aspire tour, so I'm five years in. And I still. I mean, I have a top 10 podcast on Apple, and. And it's very organic, and I still don't monetize it. I don't even know how to monetize it, to be honest. Like, you. You crush it. And I do not. I don't even know how to do, like, it's just funny.
Scott Clary
Well, you're very busy, but if you ever want tips, I need them.
Eddie Wilson
I need them. But it's like, it's funny because now you look at it like, I have capital that chases me. I have talent that, you know, it's, it's. It's interesting. It's just hit a coffee shop right before we came here, and I'm walking in, the guy walks up and he's like. Shakes my hand. He's like, Eddie, he's like. He's like, I saw you here, saw you there, watch your podcast, and I didn't know who this guy was. That stuff almost irritates me, like, because I love my space and I love. Like. But. But then he goes, you know what? I. I heard about your operating system. That you have. He's like, could you put me in contact with. I mean, like, it was a lead that was created out of nothing because I just stayed with it for the last five years. I mean, like, and I don't even know. I mean, it's like, I say I don't monetize it, but I. I monetize it in massive ways because it's the Aspire tour, it's all these things, you know, it's like, well, you have a.
Scott Clary
Smarter offer tied to the. To the content. You know what's interesting? Have you ever seen that Naval Ravicant tweet thread on the four kinds of leverage? So, of course. So then media leverage is one of the four kinds that I think everybody should lean into. And obviously, I'm in this game and you are too. Now you can have massive success without building an audience. I just feel like it just makes it easier.
Eddie Wilson
It's way easier. And it's the currency of today. You know what was interesting is watching how AI is progressing and we're building certain technology at our office and we have a product that we're going to launch by April and all this stuff. And I'm watching how AI is searching for information, right? Like, and it's very different from Google, right? And. And there's a relevance. And what I'm seeing now, and I. And I've asked so many people, I've asked at the highest level, like, that is, I literally was on a call with the number three guy from Instagram, one of the early, earlier guys on Instagram I was talking to the other day. I'm like, I said, is. Is content. As you know, I said, to me, it seems like AI, I said, whether it's ChatGPT or you name whatever AI tool you want to use, seems to be putting a premium on my content information versus my published information, right? Like, I have a website, I have all this data on me. I have white papers. I have. And it's like. And if you ask AI question in regards to anything that I've said or any of my theories or something like that, it's pulling up content from YouTube. It's pulling up content for my podcast. It's pulling up. And it's like, I think that the currency that people are going to miss out on is if they don't build what you're talking about, what you help people do. I think that, you know, gone are the days where Google's searching index content, and it's like AI is pulling directly from your Instagram. So I mean, like, it's pulling from.
Scott Clary
Because that's what people are interested.
Eddie Wilson
What they're interested in, and it serves.
Scott Clary
Up what people are interested in. That's it.
Eddie Wilson
And it's real time. It's like, I could have built my website two years ago, and so I looks at that and says, oh, that's two years old content. But what he just posted on Twitter an hour ago. Yeah.
Scott Clary
Okay, so I want to go back to your story after you exited. So the, The. The. The 76 companies was in 2019. That wasn't even the largest exit. But I want to talk about some sort of real things that you went through, because I think these are interesting. I feel like it's. Entrepreneurship is very lonely and isolating, and I think this sort of shaped who you are today. You mentioned you're more focused on sort of philanthropic, altruistic endeavors. You had a bout of depression. Speak to me about what was going on in your life after the exit, because obviously you've made more money than most people will ever make. Why are you still lonely? Why are you still depressed? How do. What was the thing in your life that was not being solved when you were just trying to build businesses and make more money?
Eddie Wilson
I could speak about it scientifically, I could speak about it practically. I could speak about. Because in the end, it's like most entrepreneurs, the dopamine that they get from the identity of the success of whatever they're creating is something that becomes addictive. And for me, you know, from a scientific standpoint, it's like you get addicted to being the guy, you know, like, you get addicted to solving all the problems. You get addicted to making the sale and hitting the milestones. And it's like, that's part of it. The second part of it is, is in that loss of identity, you, if you don't have a clear path to recreate it, which is why most people make bad decisions after their exit. It is. They're just trying to recreate some sort of identity. And so they go try to invest or they try to be. They try to reinvent themselves in some way. If you don't have a clear path that really does give you fulfillment, what happens is, it's like a. It's like you fall off the cliff, and then there's like another cliff. It's like, it's just like. Is this constant, like, tripping down the mountain type thing. It's like. And for me, that's what happened. I. I lost my identity. You know, like, I. I had this. The first exit And I then was really hyper focused on my acquisition. So that, that was like where I was. So I didn't really have that big identity hit. But then when I was, you know, because I had the first exit, then I acquired this other company. Then we got 76, you know, 80, 86 total companies. We had a big insurance company. It's like now I'm on the stage and I'm being asked to speak and Now I'm speaking 25, 30 times a year internationally. And it's like, and, and at colleges and it's like now my identity is this. And now it's all gone. Thousands of employees. Now I have 30 or 40 to talk to. You know, it's like I had seven high rise buildings in Kansas City and it's like they're all gone. You know, like I'm sitting in a small single office in Atlanta, Georgia. You know, it's like all of it. And that was really tough to deal with because money doesn't bring fulfillment. And really, you know, most people that have an exit if, if you increase your income to, you know, let's just say somebody's doing really well and they make, you know, 500 grand to a million bucks a year and all of a sudden you get to 3 million bucks a year. You know, you really from 3 million have a hard time really creating a different lifestyle, right? Like, unless you want to go crazy and go buy yachts and just go crazy. But it's like you really, once you get to that level, like you're really not buying a bigger house. You're really not, you know, you're not buying 50 cars now. You still have the ones you have or you upgrade, you're not, you're still busy, so you're not taking a whole year's worth of vacations. You're not, you still have a lot of the same friends, you know, so it's just like, is this weird, weird experience. So the money all of a sudden becomes like, oh. And then you're looking back at it going, well, I really thought it was going to provide this for me. And then it doesn't. So you like are lacking fulfillment, you're lacking purpose, you're lacking identity and you're feeling it. And I was feeling it in a big, big way.
Scott Clary
Did you. I've, I've had this conversation with a few other people that have had pretty large exits. Was there ever a feeling like, oh, I've now killed my cash flow, I can't this up.
Eddie Wilson
Yeah, there was a stress to it, but I I didn't have that necessarily because I felt like, oh, I already did it once before and oh yeah.
Scott Clary
You had a repeat.
Eddie Wilson
Yeah, so I had a repeat. So that helped. I wasn't fearful. There wasn't a lot of fear. I will tell you though, that when, you know, I was in my late 30s when that happened and the midlife crisis kind of came in because it's like, well, what if that was the biggest moment of my entire life and I. What if I lived to 80 or 90? What do I have 60 years worth of Nothing is as good as this. You know, like there was some of that.
Scott Clary
What would be your advice to an entrepreneur then so that they don't fall into that? Is it like build for the right reasons?
Eddie Wilson
Yes.
Scott Clary
Is that it?
Eddie Wilson
It's 100, it's mindset, why am I building? And then once I get that under control, you know, it's like, like if I'm, if I'm building not for ego based purposes and then I tie it to purpose and I'm building for something that's purposeful, the purpose never goes away. Your identity never goes away and the purpose never goes away. It's like if you can master those two things while building a company, I think it actually becomes very, very. And I've worked with a lot of guys that are exiting, founders that are exiting, and that's the conversation we start having a year or two in advance. You know, it's like part of succession planning isn't just like, what am I going to do to avoid all the taxation on exiting this company? It's what am I personally going to do to avoid the, you know, the, the identity tax that's going to come if I'm not tied to purpose and growth for the right reasons.
Scott Clary
And this is where you had to find purpose post exit.
Eddie Wilson
Yeah, that was it.
Scott Clary
Do you think a lot of people struggle with this because there's no like playbook, there's no rule book for no. And nobody talks about purpose when you're building a company because when you're young, you're so hungry and I think when you first start you're like, I want to make money. And then you realize that money's not coming. It would be way less stressful to just work a job. So then you got to have to like some internal reason for doing this if you want to keep doing it. And it's not money anymore because then you start to make money, but you're like, I'm working 100 hours a day so I can't Even spend the money that I'm making. But then I could totally see how on that sort of treadmill, fast forward 10 years, you exit, you haven't thought about purpose for the last 10 years. And then your whole identity overnight is just like gone, gone.
Eddie Wilson
But I don't think that you can substitute purpose for like another gear to get to the success you want, which is what most people do. They're like, explain that. Okay, so most people are like, okay, I've got these gears and I'm hitting like, it's like you find this success gear and it's like, okay, now I'm, I've hit this revenue goal. Okay, now I've got profit. Okay, now I've got my dream house. Okay, now I've got. And it's like. And they almost like try to attain to purpose. It's like, okay, now that I've got my dream house, my dream car, my dream life, now I need purpose. And it's like, I think purpose starts way earlier. Like the quest for purpose starts earlier than that. Because it's not just like another gear, it's not just like another notch on the belt. It's like if so it's such a big letdown, you know, like, because purpose is interesting because oftentimes purpose isn't found in days or moments. It's fine. It's found over a lifetime. You know, it's like. And so you need to start like searching for it early, you know, because when what I, what happens, I have a non profit, we're in 100, 103 countries now. I have a lot of entrepreneurs are like, hey, I want to go on a trip with you. I'm like, okay, we've got orphanages, feeding centers, we're digging clean water, we're building businesses overseas. Come with me. And they expect that that purpose is going to come in that one, you know, four or five day window of feeding orphans or helping dig a well or whatever. It's like. And they're like, okay, but it didn't come yet. So now what? You know, it's like that's, it's, that's not how it works.
Scott Clary
Have you heard of the, the concept of the hedonic treadmill? I have, yeah. So that's exactly what you're describing. It's a toity, basically you just keep looking for more and more and more because I guess the dopamine hit from the next achievement that wears out and you go after the bigger dopamine hit. And I think that they're actually, they think that purpose is at the end of this treadmill.
Eddie Wilson
Yeah, they think the ultimate.
Scott Clary
It's the ultimate. If I. If I finally exit for 100 million, 500 million, whatever, then I'll find purpose in my life. And that is not the case at all. Which means that you're not even building for the right reasons.
Eddie Wilson
It's not. And what you find is when you get on this deep search for purpose, most of the time you're still looking at it as productivity or an output. And what you find is that purpose is actually being content with who you are at its core and what you bring into this world. It's like, you know, I found purpose in my nonprofit, but really my. It was a journey of trying to understand who I was and what I did and what I felt called to and why I was created. It's like all these things. Then it was like my. What people would call my purpose. I wouldn't say is my purpose. I just think that's the output of my purpose.
Scott Clary
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Eddie Wilson
Yeah. Okay, that's it.
Scott Clary
If somebody is at that stage in their career and they've had some great success, what is your advice to that person who doesn't have the purpose? They're kind of seeking it a little bit depressed. They're trying to figure out where they should spend their time and energy. Like, what do you tell that person?
Eddie Wilson
Yeah, it starts with a lot of self work. You know, we. If they're going to keep chasing outputs versus chasing inputs. Like what. What is actually going on inside? You know, it's like, I have a guy that I really subscribe to. His name's Larry Yatch. He's super great guy. He's former SEAL team leader and does a lot of trauma work. And so much of what we do is just based on our subconscious activity, right? It's like we get taught these things in our subconscious and then they just happen, you know? And real quick, I was sitting in Columbia with a group of entrepreneurs and this lady looks at me. I have. At that time, I was probably serving 3,4000 orphans a day.
Scott Clary
So you'd already started?
Eddie Wilson
I built it, I scaled it, you know, like. And I'm sitting there and she looks over at me and she says, why orphans? And I was like, I. I don't know. I. You know, it's like it was like this weird moment of like. And I was like, because it brings me some level of fulfillment. She was like, why? And I was like, well. And I, I started walking Back through it. And what it was was I had a brother that, but got a really horrible disease and basically like, started off life normal and then progressed to death. And he ends up in almost like a vegetative state where my parents have to take care of him. So I watch like, the world love my brother and then reject my brother in the same lifetime. Like, he's a cute little kid and the world loves him. And then, and then my later life is watching thousands of people stare at him, tell my mom, like, you know, just say horrible things that when people don't understand, when people go through that stuff, stuff. And what I realized is like, I really get a lot of fulfillment out of being a voice for someone who has no voice. And you don't, you don't even realize why you do those things. You're just like, doing them. It's like, oh, I felt the fulfillment of giving, you know, orphans a voice by being there for them. But I never realized what it was. So like, literally on that trip was like, it dawns on me. It's like, oh, yeah, like I, I get it now. It's like. But it's like, I think that it comes with self reflection, self work work, like the internal self work. But I do think that it oftentimes comes naturally. Begin to understand ourselves when we begin to serve, when we begin to give, when we begin to extend ourselves past our own little bubble. So oftentimes I just say, start by doing what makes you happy and gives you fulfillment in any way. Like, go find a way to serve something. Like serve a board. Serve something. And, and, and it really depends on, you know, lifestyle too. So one more step back. I have a lot of 20 somethings that ask me this question, right? Because they've seen me exit, they've seen the stories. And I always tell them, you're either a gonna, you're gonna search for purpose and meaning today, or if you don't have that, let's just say that DNA, because most of them don't. They're like, they're not gonna just go sit and meditate and think through deep thoughts. So then I tell them, okay, well, what's your, what's your desire? Well, I want the Lamborghini, the jet. I'm like, okay, then hurry up and go get it. Because one day you're going to be taking a selfie on the Runway with your Lambo and your jetting and realize like, well, this is the emptiest feeling in the world. And then that's going to take you to the Place where now you don't have a choice but to do it. So either do it now because you can, or go crush it so that at some point it forces you to, so that you still can have that experience in life.
Scott Clary
Do you feel like after doing a lot of sort of, you know, deep self work, do you feel like this has made you a better entrepreneur?
Eddie Wilson
I actually do. Not because I think there's more productivity or efficiency in my life, but because now I see everything as purpose driven, you know, like, so I think one of the greatest things we do is not me acquiring companies and performing them. I think it's the. I go into third world countries and give money to kids that have come up through our system and helped them start businesses. And even though their businesses, like I have a young guy named Isaac in Guadalajara who has a little cleaning business and I funded it, he can support his family. Like, this is not going to be a hundred million dollar business. He can support his family and he can have a good living. And I look at that and go, that's success. That's true entrepreneurship. The ability to take care of oneself and the things that they love and to be able to provide for those around you. It's like, that's entrepreneurship. And it's like, so I look at those moments and think like, that's what defines entrepreneurship for me.
Scott Clary
That's the way that people should start it if they could, but I feel like they don't.
Eddie Wilson
To your point, that was a huge expectation as to what it's going to create and what the, you know, what the world sees as success.
Scott Clary
Right now you run 27 companies, you speak to around what, 5,000 plus people monthly at Aspire Tour, like everybody's coming up to you, trying to, you know, pick your brain, connect you, I'm sure, like non stop. But you also speak about being lonely. How come you feel like you're lonely at this stage in your life when you basically accomplish whatever you want to accomplish now you're getting the exposure. People know who you are.
Eddie Wilson
Loneliness is, it's not about, it's not about people in proximity. It's about true connection. And when you get to this place in your life where you really just want to live in purpose, live in alignment and do good things in the world, it's like what you find is there are few people that live on that plane. And so then when few people live on that plane and everything's about business growth, like every question I get asked is, well, how do I scale my company? How do I do it more efficiently, how to find the right person, how do I train this leader, how do I source more capital, how do I. It's like those are lonely questions. Because like, what I want to talk about is like, okay, well we have this group of orphans and you know, the Philippines, that I want to somehow teach them entrepreneurship. And it's like, though I don't get asked those questions. So. Loneliness is not about proximity to people, it's about connection to the things that you love. It's like, I mean, think about like if you've ever been in a relationship and you're not on the same plane, you could sleep in the same bed and be lonely. And I think that that's where life is sometimes for me. You know, it's like, and I have my inner circle and I'm not, I wouldn't say that I'm lonely, but I experience lonely loneliness. And it's mainly because the whole world wants something from you that you know is not going to serve them well. And all you want to do is give them something deeper, which is that lack of connection.
Scott Clary
How do you navigate that when you walk into rooms?
Eddie Wilson
I think I constantly speak towards the need of it. And I feel like the law of attraction, what happens is as I speak it and as I talk about it and as I'm open with it, like I'm not, not normally an open person. So like if you'd asked me four or five years ago to talk about loneliness, I'd been like, yeah, let's cut this, let's not get this direction. But today what happens is now that is me putting it out there. The law of attraction will put somebody else that's in that same feeling and same space into connection with me. And I'd be like, hey, I feel the same way. You know, it's like now all of a sudden I'm creating connection.
Scott Clary
You mentioned how sometimes it's frustrating to get through to people who are younger in their career that are looking for the Lambo in the private jet, right? And I think that that's probably, you know, this, this version of success that has been sold, sold to them by Instagram and tick tock and everything. What frustrates you the most? Like, if you could just take that person, that 20 year old Eddie and say like, please stop believing the hype. What frustrates you the most about that person? What would you tell that person to do differently?
Eddie Wilson
Yeah, what frustrates me the most is I. We have Tim Grover come speak week quite a bit and Tim Grover wrote a book called Winning. And what frustrates me the most is people that say they want something but won't give themselves to it. So I have a 20something that says, I want the Lambo and the jet. I'll talk about the purpose, and then you can see it just go out. It's like it doesn't connect at all. I'm like, okay, well, let's talk about get the. Let's hurry up and get you the Lambo in the jet because you're going to realize that you need purpose. So, like, let's hurry and get. Get you there now. Past this point, you got to be all in. And very, very few people are all in. Like, very few people are willing to give the time, the effort, the energy to take, or what it takes to get to that. So you realize, like, oh, they're going to chase this thing their whole life, never get it, which is the majority of humans, and never actually experience fulfillment. You know, it's like, that's frustrating because it's like, if you would just go all in. I mean, think about it. You. You know, I know that you do a lot in the workout space. It's like, could you get somebody in shape that they just would give you the time? Of course. Could I get somebody success? Could I grant somebody success in business if they just give me the time? Yeah, It's a natural part of life. So my frustration is typically a lack of commitment. And I see what you talked about earlier, which is we want that instant success mentality. We want the social media mentality. And so what happens if it doesn't come fast enough? Then they're onto something else, which is only going to prevent them from getting to fulfillment longer. Right.
Scott Clary
I've thought about this a lot, you know, mostly because I experience it with the podcast. I've probably had, over the course of me building this podcast, about 40 or 50 people ask, like, how do I start a podcast? It's a pretty common question. And I have all my SOPs, and I have all my everything that I've ever done, and I should probably sell it at some point, but I never have. I have it sitting in my Google Drive and I just send it to people. And there's two people that have actually taken it and ran with it and actually have successful podcasts. I'm not great at math, but it's not a. It's not a significant percentage of. 2 out of 50 is not a significant percentage. I guess that'd be 4%, but. Yeah, but the point is, I think the Bar is so low because so few people will really do what it takes to be successful. But it's also, it's a lot of work, but it's not that complicated.
Eddie Wilson
No. And it's about, and I say this in kind of the business teaching and, you know, speaks that talks that I do is like, it's not about being 100 better than your competition. It's about being 5% better consistently. It's like, you know, I've got three boys and my sons. Oftentimes I'll sell. I'll say to them, like, look, if the average person gets out of bed at 7:45, in order for you to be above average, get up at 7:30, it's 15 minutes. Like, like. And you've literally crushed the rest of the world today. Like, the bar is so low. And that's business too. You know, it's like with our coffee company, people are like, man, you put a coffee shop right down the street from Starbucks, Are you crazy? It's like, no, the, the bar is so low, you know, like, it's, it's like, I don't have a problem with that. Like, it's, I wouldn't either because I.
Scott Clary
Don'T even like Starbucks. So I would totally go to.
Eddie Wilson
Right. And, and the world does. And, and it's like. And so. You're absolutely right. Like, it doesn't take, it doesn't take that much more effort to be exceptional.
Scott Clary
So what's the blocker then? Outside of just needing instant gratification? I mean, you speak to over 5,000 people monthly. You've worked with how many CEOs of companies? I would say the CEOs of companies are probably oriented towards action. So there's probably not a good sample size, sample audience. But out of the 5,000 people that come to Aspire Monthly or whatever that number is, how big is Aspire now? Am I quoting right? Numbers?
Eddie Wilson
Okay, yeah, I mean, we, if it's bigger, it depends on the market. I mean, like, we could have 2,000 or we could have 5,000. It really just depends.
Scott Clary
So, Basil, you're getting thousands of people walking into that room. They're listening to the most influential motivational people on earth.
Eddie Wilson
Basically, some of the greatest business minds too.
Scott Clary
I mean, what percentage of those people actually take action and change their lives and, and why don't 100% of those people do it? Like, what's the blocker?
Eddie Wilson
There's a lot of blockers. There's a lot of signal to noise ratio in that they don't choose a path I always, I say this a lot. Like, you know, I have an operating System, we have 3,000 companies globally that operate on my operating system. And somebody will say, is yours better than EOS or Traction, you know, or scaling up? And I'm like, I don't know that I can quantify and say it's better. The fact of the matter is, is it, it works when somebody uses it and so does eos and so does scaling up, and so does every other operating system out there. Like they were created on success model. It's like that, that signal to noise ratio is really loud today. And so what happens is you've got a lot of people that look at it and they change on a daily basis of what they think success is. So you have to stick with something. You have to choose a path, stick with something. But second to that is oftentimes it is the instant gratification that we seek. And again, it's like, if you think about my principle of like, you gotta be 5% better than the competition on a consistent basis, this. But you also only have to outlast your customer one more day than they last, right? So it's like, what's the, what's the, what's the equation? It's like there's really four steps that I call the perseverance continuum. It starts with, you know, there's always fear in starting something. There's always pain and starting something, and you really can't determine how much pain you're going to go through. And there's always perseverance. How long am I going to stand to the weight? And then there's always success, right? And the fact of the matter is, is most entrepreneurs are just an entrepreneur who stayed in the game one more day than somebody else.
Scott Clary
That's it.
Eddie Wilson
It's like the bar is so low. So most people don't architect their lives that way. A lot of entrepreneurs, they, they'll choose multiple pathways because of all the noise. And then they get frustrated. And then instead of just sticking it out for one more day and tell themselves, one more day, just one more day, day, just one more day. What they do is they've kind of got this roulette mentality where it's like, I'm just all in on black and let's just see what happens. It's like, I'm just going to spend all my money in marketing this month. I'm just going to, I'm going to put all. And it's like, and if it doesn't work, it doesn't Work and I'll go back to corporate. It's like, that's the mentality.
Scott Clary
And then they chase something new and shiny, and that doesn't work because they had the same mentality that would have applied to that. You know, somebody asked me yesterday what would be a good side hustle to start? And I'm like, any of them? Yeah, just stick with it. Yeah, just stick with it. And you'll find a way to make more money than a. Than a. The market will always pay you more for your skills than an employer will.
Eddie Wilson
It's so funny. I have a barber that comes to the office and cuts my hair. I have a guy that, you know, comes and cleans my car. Both of them in the same week. Ask me, what would I. If I had a side hustle, what would you do? I said, I'd be a barber because you're a barber. And then, like, the guy that's detailing my car, he's like, what would your side hustle be? I was like, detailing cars. He's like, no, no, I mean, like, what would your side. I was like, detailing cars. He's like, well, what about. For me? I was, like, detailing cars. It's like. It's like, it's the point. You know, it's like, you know, you can. Doesn't take that much more effort to be exceptional. Like, could he be the greatest barber in our area? Yeah, like, he could be. Like, could you be the. Could you add social media to your presence of. Of doing detailing cars and become the greatest, you know, car detailer in our. You could, like, 100.
Scott Clary
It's just the bars have to get after. And the. And the bar is exceptionally low.
Eddie Wilson
Yeah.
Scott Clary
One of the last things I wanted to touch on. I love Ryan Holiday. You've read Ego is the Enemy multiple times. Why is. And. And Ryan Holiday is actually more known for stoicism than. Than anything. But why Ego is the Enemy? Why is that such an important piece of work that you love?
Eddie Wilson
Yeah. So Ryan Holiday, we've had him come and speak, and he's. I like that he rephrases stoic philosophy most. I love. I love the meditations of. Of Marcus Aurelius. Like, I think that should be a must read for every entrepreneur because it creates a. You know, it's like, I always tell the story of Julius Caesar now. You know, his rise to fame ends up getting him stabbed by Brutus, his best friend, because he became the bottleneck of his empire. Right? Like, he grew so fast, and then every decision stopped with him. So the Senate Literally talks his best friend into walking in and stabbing him. Marcus Aurelius, if you read his Meditations, he's very much like self reflective and you realize like he puts a huge emphasis on the people that help him build his empire and there's a huge difference there and the outcomes are different. And so when I read the Stoics, I feel like most of them have the emphasis of self reflection, self regulation, an understanding of what I'm capable of, commitment to all things that are purposeful. It's like there's so many things that memento mori living today. It's like there's so many just amazing philosophies in that. And I think Ryan Holiday is a modern day writer who makes it plausible for a young entrepreneur to read it and understand it. I've given meditations out to so many young entrepreneurs and then I asked them to read it and they haven't. I give out Ego as the Enemy, which I think is one of the biggest works of Ryan Holiday and one of the most important first steps, you know, his last one, Wisdom Takes Work is an amazing book. However, if you don't read Ego as the Enemy, you never actually realize you need wisdom. You know, it's like, so I say that because I get platforms to speak and I. It's the book I want every young entrepreneur to read because it's like if they can get ego out of the way, it goes back to my thesis, which is then it's self reflection. Then you start working on purpose, then you're doing things for the right reason.
Scott Clary
Fully agree with everything you said. I love Ryan Holiday's work. How do you get ego out of the way?
Eddie Wilson
Ego is nothing more than, you know, believing something, you know, like believing that you're, your abilities, who you are, is more important than it really should be. The way that you get that ego out of the way is oftentimes reflecting on who you really are and living and being okay with your flaws and with your limitations. Oftentimes. The biggest mistake that I see my friends make in going and acquiring companies, they sell a company, like I'm going to go acquire a company is they walk in and believe that they know how to solve it. I think I tell them every time when they're acquiring it, when you're acquiring the first one, believe you don't know how to solve it and believe that the person actually has the answer. They haven't unlocked it yet. So start looking at their genius versus your genius. Because so much of of our failures are tied to a elevated Belief about ourself that's not real. And so it's like if you come into every situation believing you don't know the answer, you are probably wrong, right? It's like then all of a sudden you, you always have wisdom and knowledge and information at your fingertips.
Scott Clary
This turns you into a forever student.
Eddie Wilson
Forever student, yeah.
Scott Clary
One of your quotes, which I love. Everything I want is on the other side of my ego. I wish more people would understand how powerful that is. I, I really, really. Because I think about, think about why somebody would fail in business. It's because they think they know what they don't know, right?
Eddie Wilson
Every time.
Scott Clary
And that's it. Because if you didn't have an ego, if you just understood that, you go into it like, I'm an idiot. I don't know what to do here. Let me, let me research as much as I can. Let me study as much as I can, let me ask as much as I can. Like, all of those habits only exist if you don't have ego.
Eddie Wilson
I think that to be a true entrepreneur that is good and successful as fast as you possibly can be, you have to walk in every situation with no ego. But also with decisiveness, you can allow your ego to then paralyze all things like, okay, I don't know, so I'm gonna have to just sit back.
Scott Clary
But that's difficult because there's a duality.
Eddie Wilson
There's a duality there. And so to be a successful entrepreneur that moves fast, you have to remove your ego and then make decisions. And I, it's the 80% rule. I need to be 80, I need to be 80% right on every decision that I make and have enough ego or have enough, enough absence of ego that when the 20% of me being wrong shows up, that I adjust. And it's like Lee Iacocca always talked about how his business model is not plan and prepare. It was act and adjust. And so I have an act and adjust model. I go into situations without ego as much as possible, believing that I don't have the answer, but I'm willing to fail. So I make decisive action. And because of my experience, I'm right 70, 80% of the time. Then I admit when I'm wrong 20 to 30% of the time as fast as possible. And then I adjust to optimize how you learn too. It's iterations.
Scott Clary
What's next for you? So I mean, your focus now, obviously you have aspire, you're still acquiring businesses. What does the next 10 years look like for you?
Eddie Wilson
The next 10 years for me is a full sprint to endowing my nonprofit with all of my investments and opportunities. I have a nonprofit called Impact Others. It operates in over 100 countries. We do feeding centers, orphanages, clean water projects, and build small businesses for budding entrepreneurs. And I don't want to pass on the burden of fundraising to the next generation. So I'm creating it. But it's this big monster machine now. I need to make sure that it's endowed forever so that I can pass on the ethos and the activity to the next generation without the burden of fundraising. So that's why I'm still doing what I do.
Scott Clary
You, you've had incredible success. If you could go back, tell your 20 year old self one thing, one piece of advice, what would that piece of advice be and why?
Eddie Wilson
The piece of advice would be that success takes time. It's like we want things so fast. And every poor choice I made along that entrepreneur, entrepreneurial journey is I, I made it because I believed that I didn't have time. You know, it's like, like what happens is now I actually don't have as much time as I did back then. Back then, time was my ally. If I just would have waited one more day, if I just would have waited out certain situations. And so when I'm young, time is my ally. When I'm old, time is my enemy.
Scott Clary
How has your definition of success changed?
Eddie Wilson
Definition of success has radically changed in that I would say success is about living a daily optimized experience. It's not about a metric of. It's not a KPI, it's not a, it's not a capital requirement. I think success is a daily optimized experience that I'm going through. I think wealth is about having enough today that if I, if I take care of all my needs, it doesn't diminish my amount tomorrow. So it's like, it's not a mon. It's like I'm going down these redefinitions of everything in my life because then it creates contentment. And when you create contentment, then you can live in full purpose.
Scott Clary
What's one opportunity that you're excited about today that people start looking at?
Eddie Wilson
I'm excited for the disruption that's happening with AI. I mean, and we're investing heavily in tax software specific, you know, the, the, the government right now, the, the IRS is, it's, it's something I know our people need our, our members, our community.
Scott Clary
Because, you know, because you, you have this community, they're Telling you. Yeah.
Eddie Wilson
And they're like, like, and the government is using AI to go through everybody's tax returns and they're finding these little pieces and, and it's like, I want to create a. We're creating a preventative process where you're not going to have to have such a worry about being audited because now they put everything through AI. So we're creating a pro, a program called Business Taxes AI. And that's a really exciting project for me because I have lived at the upper echelon of, of wealth for a while. And what I realize is when people talk about the 1% we are given, you know, most people are given CPAs as like the ultimate knowledge for tax. And in our world, the CPAs are the, the doers. Right. Like, then we have tax strategists and tax architects and tax attorneys. And it's like. And so in that providing all of that at the lowest level at the cheapest rate, I think is going to really disrupt this space.
Scott Clary
I love that. So that's a, that's a huge entrepreneurial lesson too. If you find like a legacy industry that is, is like massively just inefficient and you apply AI, this is what you're doing. And, and I mean, that's a, that's a huge pain point for a small business owner.
Eddie Wilson
And it's a race to whoever gets it out first, whoever gets market share first. And so that's fun. Like, you know, it's like having the ability to go after it, create market share. I already have this massive database, so it's like, that's fun. And then really the second big thing is I'm really creating a lot of businesses overseas. And so we're constantly raising capital or getting donations to help entrepreneurs overseas create sustainable income that then feeds the greater ecosystem. And so what I'm trying to do is create not just an endowment program, but like in Guadalajara we have, we've started over nine businesses. Each of them do not have to give a dollar back, but they have to give 10% of their revenue to the ecosystem. And so in that, then that feeds the orphans that digs water. Well, stuff like that. So that's a big, big project for me.
Scott Clary
I'm so curious what happens when, when, when we can use AI to properly understand taxes.
Eddie Wilson
Yeah.
Scott Clary
Have you thought about this? Because, I mean, the reason why people pay so much in tax is because they don't understand the tax law.
Eddie Wilson
They don't. And, and what happens when we already have every, every word of tax law? In our program. And what. And if you say to this AI system, hey, you know, I need. My tax bill is going to be $20,000 this year. And it says, okay, well based on everything we have and the connectivity to your bank account and everything that we see in this classified, this is a high percentage of. You're never going to get audited. And it would never flag, you know, anything. And now you can save $24,000 in taxes by using this thing. And by the way, here's the tax code.
Scott Clary
And completely legally, legally, the.
Eddie Wilson
You're in the green the other day.
Scott Clary
Very interesting.
Eddie Wilson
Think about every entrepreneur today. Most of them live in the gray areas of taxes, right? Like they're writing off things that, you know, their trip to Disney World and saying they had a business trip, right? Like they're writing off things and AI IRS is getting smarter. Okay, well what are you going to do to combat that?
Scott Clary
This is how you combat it. So you know, all these industries that are basically, and I guess tax is an industry, but all these industries that are based on lack of knowledge are going to be. So I'm thinking like health insurance or nobody knows what they're paying for. No, at all.
Eddie Wilson
Health insurance. I mean we, we have a, we have a life insurance company and we are constantly looking at models for AI. We have a hedge fund, right. Like we have a hedge fund that, you know, we've had for a while. I force all of our traders to every trade to go into our AI bot and then I look at the efficiency and then I literally could replicate what they're doing. And I have, have 12 years worth of trades that I could feed into there based on the market conditions. It's like, it's just, we're looking at AI and everything we do not, not necessarily to replace things because we're, we're successful. So we don't. I don't need more efficiency, but it's. What does it look like at product? Like at scale? Like. Yeah.
Scott Clary
How do you get 10x out of every single person? That's very. You're going to build the next renaissance for your hatch?
Eddie Wilson
I don't know. I think it's feasible. You know, it's like, it's wild.
Scott Clary
And now, I mean like how that happened, which is a mathematician who figured out how to apply that trading. And this is what AI can do at scale.
Eddie Wilson
So that's.
Scott Clary
But when everybody has access to it, first movers advantage for sure. But what happens when everybody can.
Eddie Wilson
That's the, that's, that's the trillion dollar Question.
Scott Clary
Okay, Eddie, I appreciate you so much, man. Where can people connect with you? Where do you want to send people? Social, all that.
Eddie Wilson
I'll put stuff in its own notes. The biggest thing that I, I try to, you know, work at is connectivity. And so Eddie Wilson officials, all my social handles and I try to answer as many DMS as I can and really connect with entrepreneurs that need help.
Scott Clary
If you could only pass on one lesson to your kids, like the most important lesson you've ever learned, what would that lesson be?
Eddie Wilson
It would go back to ego as the enemy. I think everything that they want is on the other side of their ego. If they'll be that constant learner, if they'll look at the world with wonder and you know, and, and look at the creativity that's all around us and explore, it's like, man, they would be unstoppable.
Scott Clary
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Podcast: Success Story with Scott D. Clary
Episode: Eddie Wilson – 100+ Companies Exited (Aspire Tour Founder) | The Most Expensive Education
Release Date: January 20, 2026
Host: Scott D. Clary
Guest: Eddie Wilson
This episode dives into the remarkable journey of Eddie Wilson, entrepreneur, investor, author, and philanthropist known as the “king of exits,” thanks to his record of owning and exiting over 100 companies totaling more than $1 billion. Wilson unpacks the lessons learned from his early setbacks, the importance of gratitude, mastering acquisitions, building community-first businesses, and why fulfillment and purpose matter more than money. The conversation is candid, covering the emotional and mental sides of entrepreneurship, as well as tactical business strategies.
Memorable Quote:
“That day I made a couple of promises to myself... I’m never gonna treat somebody like they treated me. And I’m going to learn this game, because I was outmatched, outplayed.”
—Eddie Wilson ([06:50])
Insight:
Notable Quote:
“Most entrepreneurs, the bad thing happens to them and it now classifies... now this is who they are.”
—Eddie Wilson ([06:50])
Takeaway:
Key Learning:
Quote:
“When I was building the agency, I was outselling, I was doing everything... This now was too big to be based on me. So I had to attach to these leaders.”
—Eddie Wilson ([16:42])
Notable Quote:
“You’re not going to truly scale a company when it’s based on one person.”
—Eddie Wilson ([22:00])
Quote:
“The economy is like the board I’m playing on and everything else are just pieces.”
—Eddie Wilson ([25:04])
Quotes:
“Build community first, serve the community by buying companies that serve that community. That’s always been my theory.”
—Eddie Wilson ([30:51])
“You cannot think monetization first. Community has to be community first.”
—Eddie Wilson ([34:41])
Memorable Quotes:
“Money doesn’t bring fulfillment… If you don’t have a clear path that really does give you fulfillment, what happens is it’s like you fall off the cliff, and then there’s like another cliff.”
—Eddie Wilson ([42:00])
“Purpose isn’t found in days or moments. It’s found over a lifetime.”
—Eddie Wilson ([47:21])
Insights:
Quotes:
“Everything I want is on the other side of my ego.”
—Eddie Wilson ([70:59])
“To be a true entrepreneur that is good and successful as fast as you possibly can be, you have to walk in every situation with no ego, but also with decisiveness.”
—Eddie Wilson ([71:18])
To his 20-year-old self:
“Success takes time… Every poor choice I made along that entrepreneurial journey is I made it because I believed I didn’t have time. When I’m young, time is my ally. When I’m old, time is my enemy.”
—Eddie Wilson ([73:26])
On what he would leave his kids:
“Everything that they want is on the other side of their ego. If they’ll be that constant learner... they would be unstoppable.”
—Eddie Wilson ([79:57])
For actionable business wisdom, real insight into the entrepreneurial mind, and lessons on success that go far beyond money, this episode stands out as essential listening.