Digital Social Hour
Why 99% of Entrepreneurs Fail to Exit (And How Not To) | Eddie Wilson DSH #1094
Sun, 12 Jan 2025
Discover why 99% of entrepreneurs fail to exit their businesses successfully and learn the proven strategies from Eddie Wilson, known as the "King of Exits" with over 100 successful company sales! 🚀 In this eye-opening conversation, Eddie reveals his three-pillar approach to creating valuable businesses that buyers chase after. Learn how he achieves an incredible 78% success rate (compared to the industry average of 8-9%) and why operational efficiency is the key to commanding premium valuations. From his first painful exit where he lost $30M to building a business empire and transforming countless companies, Eddie shares raw insights about what really matters in business and life. He breaks down why most entrepreneurs struggle to sell their companies and provides actionable strategies to position your business for a successful exit. Beyond the business tactics, Eddie opens up about the surprising truth of wealth, materialism, and finding genuine fulfillment through impact. His journey from chasing profits to feeding over 4,300 children daily through his humanitarian work offers powerful lessons for entrepreneurs at any stage. Whether you're building to sell or looking to create lasting impact through your business, this conversation delivers invaluable wisdom from someone who's mastered both the art of the exit and the pursuit of meaningful success. 💫 #operationaleffectiveness #operationalefficiency #commonpitfallsinbusinessexits #efficiencystrategies #operationalperformance CHAPTERS: 00:00 - Intro 00:50 - Eddie's Events 02:10 - Podcasts and Media 04:30 - Acquiring Companies Strategies 05:00 - Prolon Overview 06:00 - Red Ocean vs Blue Ocean Strategy 07:20 - Aspire and Ambition 09:46 - Artificial Intelligence Insights 11:06 - How to Sell Your Company Successfully 13:09 - Importance of Mentorship 16:28 - Defining an End Goal 17:56 - Materialism and Its Impact 20:58 - Money Doesn’t Buy Happiness Discussion 24:00 - Selling a Business: Key Steps 26:09 - Eddie's Track Record and Achievements 28:28 - What Eddie's Excited About in the Future 29:21 - Where to Find Eddie Online APPLY TO BE ON THE PODCAST: https://www.digitalsocialhour.com/application BUSINESS INQUIRIES/SPONSORS: [email protected] GUEST: Eddie Wilson https://www.instagram.com/eddiewilsonofficial SPONSORS: Prolon: http://prolonlife.com/DSH LISTEN ON: Apple Podcasts: https://podcasts.apple.com/us/podcast/digital-social-hour/id1676846015 Spotify: https://open.spotify.com/show/5Jn7LXarRlI8Hc0GtTn759 Sean Kelly Instagram: https://www.instagram.com/seanmikekelly/
Chapter 1: Why do most entrepreneurs fail to exit their businesses?
Mid cap space, and then I serve it up to the big guy. So with operational efficiency, all I'm doing is taking something that already exists that's good, making it better, and making it something that they can actually enjoy, take advantage of, and run. And so what I've gotten really good at is seeing the small guy for what he can be.
All right, guys. Eddie Wilson is here today. We've had this on the books for a while. Thanks for coming in, man. Glad to be here. Yeah, I think we scheduled this a year ago because you're so busy traveling. Long time.
Where have you been lately? Everywhere. Nashville, Chicago, LA, you name it. London, Egypt. I mean, yeah, all over. And you're having events in every city? You know, I have a nonprofit on the international stuff. So I don't do a lot of events internationally. I'll speak four or five times a year. But for the most part, the events are in the US.
Got it. And you have over 100 exits. So did you start doing these events after you were selling companies? I did.
You know, I've always built community. And then as I built community, I would actually build or buy companies to serve that community. So most of my exits were tied to community. So I've been doing events for a long time, but they're more educational than inspirational. Lately, we've gotten more inspirational, self-help, aspiring entrepreneurs, stuff like that.
So you're seeing that thing in the market where people want more inspiration these days?
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Chapter 2: What is Eddie Wilson's three-pillar approach to business exits?
They do. They get beat up on everything. They get beat up on the economy. They get beat up on politics. They get beat up on everything. And then you find this source of positivity and inspiration. They kind of flock to it today.
I could see that. Yeah, I've been to like five Aspire tours. Have you really? Yeah. Wow. I will say some of them are very emotional. I remember vividly some speakers crying, like back to back to back. I'm like, damn, this is crazy.
One of the big pushes that we have is for them to be authentic and open and real. You'll see the people that come back over and over again on our stage is somebody that's willing to open up. Because if you can't open up, if you can't get vulnerable with our crowd, you're really not going to give them a pathway to success.
And so we have had a lot of emotional moments there because we ask them to be vulnerable. And then all of a sudden, you're sharing your sold to 3,000, 4,000 people. And it can be emotional for sure.
Chapter 3: How can operational efficiency enhance business value?
People like that authenticity these days. That's why podcasts are taking off. You saw how instrumental they were with the election. Yeah, they're huge. I was just watching Patrick Bet-David was on Graham Stephan's show, and he was saying how next election cycle, people will be debating on podcasts.
I think they will. I think Rogan kind of created that entryway, and it was so funny because I felt like all of us were like, why wouldn't you go? I mean, look at the eyeballs on these shows versus mass media, and you can control your message. Right. And super powerful. I think podcasts are going to be huge in the next election. I think so, too.
I think the way that we saw meta back maybe in the Obama administration then get hyper-used during the Hillary-Trump election, I think the same thing. You're going to see that natural inroads this past one, and then you're going to see massive digital media. I actually do a lot with... I used to have an ad agency that we primarily consulted big election. We promoted a lot of election.
Oh, really?
Process, yeah, and ran some campaigns. And what you see is like an earmarking of the budget early. So as these big organizations start running all of their ad spend to try to gain dollars, they're already earmarking. And I was talking to an election official recently, about two weeks ago, and he said he believed that over 60% of all spend would go into digital in the next election, which is huge.
Because if you think about today, I mean, probably 70% is on national TV, radio, so on and so forth. It's going to be a massive shift.
Yeah, I was seeing billboards everywhere when Kamala was running. Even Trump had a lot of billboards. They both raised over a billion dollars. It's wild. Crazy, right?
But think about that 60% of essentially $2 billion now moving into digital media. Some of these podcasts are going to do very, very well financially if they position themselves well, specifically to one side or another. Yeah. Would you ever acquire a podcast? I would. I actually love the idea of aggregating people eyeballs data. Right. And so, again, it goes back to.
If you have a community that knows, likes, and trusts you, then you can serve them with products. And not products they don't want, but products that already exist on their P&Ls. That's why I roll up insurance companies, tax firms, so on and so forth. Because if you can give them a better option than what they already have, they'll naturally migrate over.
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Chapter 4: What lessons can be learned from Eddie's first painful exit?
So there was a lot of those events in the health space?
Well, it's the events. It's also the influencers. The influencers really control that space. So in health and fitness, you've got massive influence from digital influencers. And if they don't show up to your show, if you don't play ball with them, you can't just run nuclear media. You can't just run ads and try to get people there. You have to play with the people who have influence.
And they really control it. And most of them have their own shows, their own, you know, digital outlets, their own communities. So they don't necessarily want to bring them into a community that they could access maybe, you know, a hundred influencers that, you know, would begin to create attrition to their own list and their own, you know, community.
100%.
Where you're making all the decisions. Yeah, that makes sense. That's why Aspire is crushing it.
It is. Yeah.
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Chapter 5: How does community building influence business success?
I mean, you go to every major city and thousands of people every time.
We do. We've hit well. That was never really our intent. We thought we'd do three or four and see how it goes. We sold out the first three and knew we were onto something, felt like our messaging hit. And how rare is that to actually try something and then your messaging hits immediately? Usually it's like you're testing, trying, growing, and modifying. And for us, Aspire hit right off the bat.
I think it's the first time in all my companies where something just hit immediately. Wow. And you've had hundreds of companies. Yeah, hundreds. But the resonance was crazy. You felt it. The moment you got there, the people walk in and you're like, wait a minute, this is exactly who we marketed to. They showed up.
And then the resonance with the actual speaker and the content, we knew we had something. It felt like lightning in the bottle the very first show.
Chapter 6: What role does mentorship play in entrepreneurial success?
Yeah, it's energetic, man. That atmosphere, it's inspirational. You're changing lives. And I feel like you can monetize that with all those emotions involved. Sure. Absolutely. Yeah. And you guys are having, what, an event a month?
An event a month. And we're scheduled out through all of 2025. Already?
Wow.
We already have all 12 markets picked. I think we've got probably 11 or 12 of the venues already locked down. Nice. Speaker's already building. It's been an interesting thing. In the beginning, when you're trying to get all these celebrities, it's like you're trying to convince them. And the first time we ever went after Kevin Hart, we threw 500 grand at him. Holy crap.
For 30 minutes, and he wouldn't even pick up the phone.
Damn.
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Chapter 7: How does authenticity affect business relationships?
And then he ends up coming in later for a lot less because the show had so much notoriety. We tried calling everybody. Mark Cuban said no. O'Leary said no. And then they see the notoriety, and then all of a sudden their agents start calling us and saying, do you think that we should be on your stage? So it just puts you in a position of strength now.
But in the beginning, it was tough trying to get those people to align with us. And they don't want to align with somebody that's selling stuff or monetizing their brand or their audience.
100%. Yeah, it's a risk for them when they speak at certain events, so I understand that perspective. Same with the show, though. I couldn't get any of those guys on at first. I didn't have the viewership.
And now you have everyone, right?
Chapter 8: What does Eddie foresee for the future of business exits?
Yeah, now more people reach out to me than I hit up. That's great. But before, it was the complete opposite. Yeah, that's awesome. So you got to start somewhere. You have to.
Then you hit critical mass, and then all of a sudden you start playing downhill versus uphill.
Absolutely. Are you doing anything in the AI space?
I'm doing a little in the AI space. It's one of the big curiosities for me right now because I'm a hardcore operator. I buy businesses, but I love to operate the business. And to the degree that you can create efficiency in a business is the degree you create both success, longevity, but also enterprise value, what you're going to ultimately sell it for.
Where AI really creates a gap is the efficiency side. So like I have operating system, empire operating system I put on all my businesses. But it's like the AI, we're messing with AI trying to determine how to make even our operating system more efficient so that we can get to better success metrics faster. And so I'm not necessarily building tech that I'm going to sell the public for AI.
I'm using AI to try to maximize my operational efficiency in my companies.
Got it. Yeah. I couldn't tell if that was a bubble or not. So I kind of stayed out for now.
I don't think it's a bubble. I mean, I think the early investments, early adopter type stuff is a little bit of a bubble, but not enough money moved into it. You know, like the crypto space or the dot-com boom. I mean, you didn't see massive money moving in early. But what you saw was massive adoption by the big brands, you know, like Microsoft, IBM, Apple.
And so I think that was a good indicator that it's the direction that the country is going to move.
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