What No One Admits About Selling A Business

This is a transcript of a panel-style YouTube conversation (Capitalism.com) featuring Ryan Daniel Moran and others about the often-unspoken psychological effects of selling a business. Major themes: loss of external validation (status, attention), resurfacing of pre-existing insecurities once money no longer "covers up" them, boredom and loneliness after an exit, difficulty reconnecting with purposeful work, and coping strategies (honesty, presence, creative sharing). The speakers use anecdotes (Mark Cuban, Phil Knight/Shoe Dog, a long-time business owner) to illustrate that money doesn't automatically resolve identity questions and may amplify internal issues that were previously masked by busywork and achievement.
Chapters
I read somewhere that Mark Cuban, the minute he was watching his computer and when he was actually a billionaire, he was sitting there in his underwear and he's, like, refreshing the page. He's now a billionaire, and his phone's just silent. No one called him.
No bullion.
But I'm a billionaire now. No one gives a fuck. I don't know if you would edit that out, but anyway, that's.
Fuck. Say whatever you want. You can say fuck, shit, cock, balls, whatever you want. So the thing that I experience after my exit was I threw myself back into work, and I tried some things that didn't go the way that I thought. And so my immediate thought was. My immediate reaction to it was I thought I was good at this. Maybe I'm not. Maybe I'm a big phony with a few more dollars.
I'll never have another successful thing again, so I won't matter.
So who does that mean I am?
And.
Everyone. That was the big one. Everyone's passing me now. That's the. That's the big one. Everyone's passing me now. Like, I. I have had and still have feelings of being Michael Jordan when he retired and the game moves on. And now the debate is, is Kobe the best ever? Is LeBron the best ever? And I just imagine that Michael's on the sidelines. Be like, I was better than all of you in my prime, but not anymore, dude, you're. You're 53 years old. And. And so that I'm experiencing some of that. But as soon as I turn off the stress and the noise and I go, oh, there I am, that thing's gonna, like. That thing's gonna come. I'll be good. But I'm so used to operating in the workaholism mode that I have a hard time remembering how to get back to that place. So. So is or not?
Oh, 100%. Yeah. We just had a wedding in Chicago, and our friend. Our good friend got married. Her dad and I just hit off a conversation. It was awesome. He imagine what you went through. But he. I think he had his business for, like, 30, 40 years. Had a huge call center, massive staff. Said, was my family.
He said, yeah, I made an awesome. A massive amount of money. It was very well worth it. The process was interesting, but I really missed it. He said, I still miss it. I don't regret selling, but I miss the business. And I think the longer that runs on, the harder that would be to replace. But the good thing is you're still young, man. Like, he's retired you know, he's. He wishes he could go back and do it all again. Have you read Shoe Dog by Phil Knight?
Yeah.
Okay, so you gotta read this. I won't finish that sentence because it's right at the end. My favorite part of the book is at the end, but I can't give it away. It's also the best entrepreneurial story I've read. Really. So, yeah, it's all about Nike and how it all came about. Everything you think you know is very different and. Yeah, amazing. Amazing. But yeah, a lot of. So I think the longer, the longer someone's in business, the more that matters, so.
Well, tell me if you think this, if I'm right on this. I think most people.
Especially now, most entrepreneurs, make a lot of money to cover up some things and.
Feeling of not being enough. You cover it up with money.
Boredom, which is so weird. We have so much to do, but we're more bored than ever because we have no, nothing that we have to do. All our needs are met.
Boredom, loneliness is another one. So you cover them up with achievement and success and admiration of others and money. And when you sell a business, you get a whole lot of those cover ups. And then once your brain normalizes it, there ain't nothing.
Yeah, you and your problems are still there, but there's no more stuff to cover it. There's no more distraction to cover it up. And so I think a lot of your inner demons come out when the, the drug goes away. And so I have found, like, other vices now are more challenging for me to fight. Like food. I have a tendency to overeat if I'm not very careful.
And by very careful, I mean show a lot of willpower. Unless I'm. Especially if I'm stressed.
Or coffee.
Like pouring. Like pouring.
I don't know what you mean.
Just pouring gobs of more coffee because you just want another distraction because you don't want to deal with whatever it is.
So I find that coming and I notice it and I caught it. It's like, oh, okay, I need to do something about this. Which is why there's the.
Movement for me to back.
You think it's like an out, like an external goalpost. So you think, oh, if I do this, if I do this, if I do this, then I'll get that you do it all. And then, you know, but I'm still here. And I read somewhere that Mark Cuban, the minute he was watching his computer when he was actually a billionaire, he was sitting there in his underwear and he's like refreshing the page. He's now a billionaire and his phone's just silent. No one called him. He's like, but I'm a billionaire now. No one gives a fuck. I don't know if you would edit that out, but anyway, that's fine.
You can say whatever you want. You can say fuck, shit, cock, balls, whatever you want.
That's so interesting. So you have to be really. You have to be happy with who you are and have your own goal post, I think, which is hard, really hard to do. And then get that feedback from yourself. And the external stuff is nice, but it needs to be that internal flywheel to keep you going to do the thing that you want to do. That's my 10 cents on it.
Alex and I are having this conversation over dinner about Alex made the statement that his.
Growth has never been predictable. It's ever been linear. Right of once I get here, then I will get here. Here, then I will get here, then I will get here. But I. Which means other people, I'm sure as well have the idea that that's how it's going to be. And I learned by mistakes. And then my best successes come out of the mistakes. So I go like, I go like this. But I think if you were to operate from that place of like, where you're truly connected to whatever it is you're excited about, you just naturally do and are attracted and attract the things that give you those exponential things forward. I just, I just know I experience when I'm in that zone. It's really easy for me to do sales and turn away bad clients because you're happy with what you got.
But when you're in your head or stressed about it, go chase bad decisions in the form of money.
Downsides and missteps are actually way lower learned. So the success, like an exit. You think, oh, I should learn a lot from this. You don't. It's the other stuff that got you there. And then you think, well, I should be 10 times smarter now because I'm 10 times richer or whatever. It's not the case. So maybe the stuff after, when you're saying some things went wrong, you had this bias that, oh, now everything I should do turns to gold. And it doesn't. And you're like, oh, shit, what do I do now? No, but that's the thing.
Yeah, I have money now and I'm good. So everything that I touch is going to turn to gold. And when it didn't, it's like, wait, am I not good because I Thought I was really good at this.
Okay.
That make a decent amount of money in a year, and then something changes. Then I go.
What do I do now? You're not alone, man. It's just part of the ride. Enjoy it.
Isn't it amazing how I really. At the end of the day, money is like a path for more self discovery.
Yes, sir.
And everything is right. I mean, like.
Through money, you get pain and pleasure. Both are portals to discover more about who you are. Even if it's things like, I enjoy this, so I want. I want more. Ah. And that. And that's why, like, when you're not stressed about it, it's things. It's that it's realization of, like, wow, everything is just perfect and the way it's supposed to be. Because eventually you get the lesson.
I don't understand how you can be stressed about money when you already have enough. And you live in a country where you have enough almost from the starting point.
Yeah, funny. So I am not stressed about money. Okay. Oh, this is fascinating. And I'm embarrassing to say this because there's a camera going, which means I have to say it.
I'm not embarrassed. I am not worried about money. I'm worried about losing the status that comes from more money. I hear you. Right now. This is real talk. Yeah. Because as I run through the scenarios, when you get that space, like, when you're not attached to it anymore, like, when you. When you can take a moment, like, all right, what's really going on in the sphere? Like, am I really afraid that this business is not gonna turn around? No. No. Because, like, I can pay for that mistake. What I'm afraid of is the fact that my peers are crushing it. My peers are doing fine. And now I feel like I'm being left behind. What are they gonna think of me when they pass me?
Does the status really go away?
It's.
I'm fully aware that it's the dumbest thing ever. Okay. Right. I'm fully aware of this. It doesn't prevent the racket from. You can catch it and you can deal with it and you can laugh at yourself for having that dumb egoic need in the first place. Comparison. Absolutely. Again, this is. This is why on your stage, I start like, this is my junk. Yeah. This is what I deal with. Love it. Because that wasn't a show. I opened up my laptop to work on that speech and I was like, who the fuck wants to listen to me?
Because I know that's my own junk and it's not the perception of other people. And I know that my status doesn't go away when I have a failure. As long as I'm honest about it. Yes, I'm comfortable, although feel very vulnerable. Talking about it and sharing it, that idea of your.
What we were talking about earlier.
Sharing your internal stuff, and then you can deal with it, can be creative.
A friend of mine that was with us at the pre.
Event.
Event of the. The event in Bucharest told me, do you realize that no matter what happens, you can go and live at any of these people houses for months and years and they will gladly have you in their home? Like, there's no. No low point for you as like, you'll be living in big houses around the world, having great friends, and just enjoying your life.
So right.
When you were talking about going to a different country, changing your name, and starting all over, I had the vision of.
Me in Austin working at Juice Land, which is a smoothie place that I go to in Austin. I just go work at Juiceland, and I would probably be happy as hell. And the thing is, as long as you are present in what you were doing, you.
You.
You won because whether you are like, you have $10 million in the bank or you're sitting in a suite in the Cleveland Indians owner's box, or you are working at Juice Land.
Were we in the owner's box or we were.
No, we were just. We were in the Peasant luxury suite. Okay, I see. I see. Okay. Yeah, we weren't cool enough to get in the owner's box. Just. Just the. Just the. Okay, the lousy luxury suite.
But.
I'm sure the owner's been there.
But as long as. No matter what your scenario is, if you're present in it and joyful in it, that that's when you've won, is when you have won. And we chase all these things, like money and an exit so that we can feel those things, and when they don't give it to us, we go back into this, and it's like life going like, are you ready yet? Like, still here was always here. You're. Are you. Are you ready to. Are you ready to be here yet? Or are you gonna go do another district? Okay, you're gonna. You're gonna drink more coffee. All right, I'll be here when you're ready. It's like, I'm probably. I'm probably gonna hit you a little faster next time. And so. Yeah, you over. You over. Drink on coffee and have adrenaline fatigue. Are you ready now? No. Oh, no. Now it's girls and sex. All right, cool. I'll be here when you're ready. And it's just like always there, just waiting and then. And that's why you had like that blissful like I found it. When you finally turn off the noise and get present or you get silent another way.
Isn't this exciting? Isn't this fun?
I just love this.











