Why 75% of Founders Regret Selling (and How to Exit Without Losing Yourself)

Hey everybody, welcome to another episode of the Business Lunch Podcast with your hosts, me, Roland Frasier, and the wonderful and telescopically inclined Ryan Deiss.

Hello, sir. Yes, for those not watching this on YouTube, I do in fact have a telescope behind me. Um, it was a gift from a friend that I literally never used, and my youngest son decided last night that he was going to figure it out. Um, we had like a full moon. We're at our beach house right now trying to squeeze in one last family vacation. He decided last night at like 10 o'clock at night. When I'm ready to go to bed.

Nice.

Like now, now is the time to figure out the freaking telescope. Uh, to his credit, he did. And, um, got some, you know, closeups of the moon. So yay. I just didn't get any sleep. But yes, that's why there's a telescope behind me. Nice.

Yeah. Speaking of telescopes, um, you and I were talking about founders exiting their companies and not being happy. How's that for it? That's a really good smooth transition.

Nobody even, dude, uh, like, I mean, just seamless.

Like, right?

Seamless transition.

Yeah.

Love it.

Uh, how about this? Speaking of looking at things more closely through things like telescopes, let's put founder exits and, uh, how they feel about post— how about themselves and life post-exit, uh, into a close-up view. How about that? That's a, that's a more seamless one. Yeah.

Yeah. That was definitely, um, sequitured.

So you were saying. You were saying that, uh, that you were looking at, I think, an article or some stats or something about this and, uh, and had something to take away from that. Yeah.

I mean, well, you know, you and I talk to a lot of business owners, obviously, who, who want to exit, who wind up exiting. I mean, that's kind of a lot of what we do, what we talk about, what we help, you know, clients and portfolio companies do is exit. And I think that's what everybody wants is this exit. And a trend that I've noticed amongst a lot of the people that we know who have exited is after, you know, a couple of years, it seems like the majority of them wish they hadn't. It's kind of something that I had noticed. And then, yeah, I just happened to stumble across this article. I guess Hartford Financial did this study. Hartford Financial Group did this study and they found that 75% of business owners regret selling their company. And I was like, yeah, that sounds about right. You know, every now and then you see these studies come out and you're like, all right, this is stupid.

Did it break down like the whys any more specifically? Than just a general regret? Like, were there categories? Yeah.

I mean, they, they talked about how, um, identity crisis was a biggie. And I know that's something that, that we've seen. Um, they cited loss of purpose, which I think is really just kind of a subcategory of identity type stuff. Um, disappointment with the buyers. Um, and, and just generally poor planning. And so a lot of people will sell their business, they'll get all this cash, and some of them will just go and spend it all, or they'll, you know, they'll be incredibly bored. And because they don't have this purpose and they don't have this identity, they decide now all of a sudden that they're going to be investors. And so they start investing in every little business and they lose because they don't have a plan for what to do with the proceeds or with themselves and their time. And so a lot of them either just kind of live in this like quiet, regretful desperation, but a significant chunk, more than half of businesses that get sold, the owner winds up swooping back in to the business. And so I thought that was all very kind of interesting.

I'm surprised it's that, that it's that high because so many of the businesses are not capable of being taken over again. They've been, you know, just decimated by the people that came in and tried to run them. And the people don't abandon them because they've made investments in them until there's really not much left. And so it's, it's, I, it would be interesting to know of the 50% that come back, what percentage of those actually get back into business versus go on and fail. Because I've watched a lot of people that we've worked with where private equity came in and bought the company and then, uh, our people come back in and they just can't, they just can't get it back. The magic's gone. The time has passed. The thing that worked, doesn't work anymore, the people or the audience has been left to wither too long or whatever. But that's a curiosity point. But let's talk about our personal experience because you and I have exited several businesses and I'll start with, for me, probably the biggest identity thing that I left was practicing law. Because the first thing that almost anybody says when you meet them is, you know, so what do you do?

Right?

And my answer for years and years and years was, you know, oh, I'm an attorney and I do this, that, and the other. And the truth is, is that I was less an attorney than I was an investor, but investor just sounded weird to me. Like, you know, like I'm a day trader or, you know, something like that. You know, you're an investor. Oh, you buy and sell stocks? You know, no, no. You know, I invest in companies, you know? Oh., you know, can you invest in my company? No, I don't do like startups and venture stuff. You know, I, I do this. I like, the explanation was just too long. And, um, and that was, that was an interesting thing. And it, for me, it was like, in that case, it was more the, like the category or the box of being able to say I'm an attorney, but that, that was very much an identity for me. And so not being able to say it was weird, you know, it was like, and I didn't feel like investor had as much status as attorney when the truth is it actually had, should have a lot more. But to me it was just too vague. And then, um, to you, probably significantly less than me, you were the initial like force behind making Digital Marketer happen, which hasn't exited, but you were also the,, you know, a primary force behind the event Traffic and Conversion Summit that we sold to one of the Blackstone companies. And I was wondering, 'cause we haven't really talked about it, but did you feel any kind of identity change or shift there positively or negatively when we sold that company? 'Cause that was a—

Yeah, I did.

That was a decade-long thing plus, right?

Yeah, it was. And I definitely did. And I think now I'm kind of far enough away from it that I can actually be somewhat introspective about it in a helpful way, not just in like a, you know, let me just get all up in my feels kind of thing. But yeah, I mean, and even though we didn't sell Digital Marketer, you know, the asset like that is still in our portfolio today. When we sold Traffic and Conversion Summit, we were effectively positioning Digital Marketer for sale. So I did exit that business from both a, you know, identity perspective and also from just say, this is my day-to-day, you know, work type thing. And it was all good. You know, it's kind of the classic case of you would much rather sell a business for a lot of money and have a loss of identity and kind of purpose than to have a business fail, lose a bunch of money, and also have a loss of identity and purpose. So I just want to just make sure that that's said, that this is, you know, still being in an incredibly privileged position. But it's why we talk about this stuff, because it's a lot of the stuff you're not you know, allowed to talk about necessarily. But yeah, I mean, after we sold that chunk of the business and then I effectively exited the business in preparation for selling the rest of it, you know, which was kind of the plan had COVID not happened and stuff like that. I was definitely wandering for a while and we had plenty of stuff to do. But what I hadn't given enough thought to is, yeah, what does my kind of Monday through Friday look like? And I think that's the difference between business owners who are builders, right? And that's kind of what I would distinguish a little bit between— it's kind of the maker-manager construct, right? There, there, you know, there are people out there who like make stuff and there are people who manage the stuff once it's been made and you need both to run a successful business and both can be, you know, incredibly valuable people and even entrepreneurial at times. But if you're primarily a maker, if you're primarily a builder, which to your point, you were even when you were quote unquote just an attorney, you know, and attorneys are almost by definition managers, not, you know, makers necessarily. Like, um, but the, I still was in this place where I'm like, well, I don't know what to build next. I don't know what I'm supposed to be moving towards and what, you know, what does this mean for me in terms of my activities? And I just felt, yeah, very kind of lost and purposeless and got You know, I don't, I never was like diagnosed with depression or anything like that, but my wife would tell you that I was not a lot of fun to be around. Yeah. And it wasn't really until we all kind of got clear on what we were going to be doing next. And, you know, I could find a new role and new thing to move forward in that I got my mojo back. But man, that took me probably a year and a half.

Yeah. And it was, it, It's very, it sneaks up on you too, because this is a conversation that I have very frequently in the companies that we're exiting and advising on exiting with the, you know, the primary people is the story that we were sold on when we sold that business was, I remember sitting at dinner talking about it, the, when we were getting like serious about it and was, they, and the conversation was, no, no, no, no, we don't want to do, we're just coming in. We want you guys to keep doing all the things you're doing. Um, you, you've built it, you've done it right. And, um, so, you know, nothing's going to change there. We're just going to, you know, expand it with the things that we've got. And I got to say, within 2 months of coming in, it was absolutely clear that they didn't want us meddling in a whole bunch of the things that they did. And ultimately, really just wanted us to show up, take advantage of our personal brands and have us talk. And I'm not saying that bitterly. I'm just saying like, the fact is they had a plan and I don't know if I would say, if I would, you know, raise it to like dishonesty, but it's pretty close because that conversation was, I mean, I, I remember it well and I bet you do too, sitting at, I remember what people were wearing even. Um, and, uh, and I remember having that conversation and it was just inaccurate and you could, you could slough it off to, well, the integration team is different from the acquisition team is different from the operational team. But in this case, there were a few carryovers from, from them. And the truth is, is that like, it was a completely different post-exit reality than we were sold and then was described to us. And so. That's a surprise to a lot of people. And I'm going through a couple of those right now where, you know, you're having the conversation with the founders and saying, look, they don't want you there after. And the argument back is always, no, no, they say they do. And I'm like, I know, but at best, it's a misunderstanding of how it's going to be. And at worst, and to me, probably, you know, closer to, it's just a lie. And I don't, it's interesting because we haven't talked about this, but it's, and I'll stop because I really want your feedback and I'm asking you too many things, but, but like that, that is something to think about. And, and that I'm kind of curious as to your take on is like, it's, they know it's not going to be the way that they're representing it and yet they're representing it that way. And that's the majority of the time. And so I'm kind of curious, just, I'll just say, you know, your thoughts on that.

Yeah. I mean, I'm, I'm, you know, like you said, we haven't really talked much about this, but I've thought about it, you know, a fair bit. And to your point, when we've been kind of walking with founders, um, and, and business owners through the exit process. And we say this to them, we're like, look, you want to make sure you get this deal figured out. You want to make sure that you don't have too much of an earnout. You want to make sure that you don't have these things because they're not going to want to listen to you after the sale is made and you're not going to want to really work with them. Like, no, no, no. And, and what I have never really articulated is I hear you. I believed it too. And I should have known better, like both you and I. Been down this road before. Like both you and I know how the game works and yet we still believe them because everybody believes that this deal is going to be a little bit different, that this person, and maybe it will be, but it probably won't. And so allow yourself to be pleasantly surprised, not disappointedly surprised. And I think that's the, that's the mistake that's made. And what's interesting is I don't know, like, If you were to hook them all up to a lie detector, right? Would they pass? I almost think they probably would.

I think they would.

I think in the moment, that's why I don't know that it's, you know, like outright deception or anything. I think in the moment they believe it too, and they kind of want it to be true. But when they get on the other side of the sale, I think a lot of it is arrogance on the part of the acquirer to say, okay, step aside and check out what we can do. I think there's an aspect of that. I also think that it's inherent for the past team because always, I mean, part of the reason that, you know, again, the stat, I need to go and find it, more than 50% wind up swooping back in. It's because like 40-something percent of business owners never left. They always stayed with the company in some capacity, right? And so because they're there and they're trying to kind of, You know, say, well, this is how we do stuff here. Now you got the new owner who's like, well, and they sort of got to flex a little bit and it winds up being this overreaction on both sides. And a lot of it's because I think during the due diligence process, everything is about what is the company worth today. And one side is spending all this time talking about how amazing it is and why you should pay so much for it. And the other side is trying to come up with all the reasons that the business is broken and it sucks. And even though they eventually do come to some sort of agreement, I think they're still coming into it post-negotiation with that mentality. The person who sold, the seller is saying, but it's so freaking awesome. And the person who bought it said, yeah, but it sucks. And I think that's the thing that inherently is going to pull the two sides apart.

Yeah. And even not on the extremes of that, because I don't see that as much as like in, you know, car dealers, car sales where it's like, you know, ah, it looks like, you know, it's got a dink here and a, you know, this happened and probably in an accident. It's more, we're arguing over the amount of add-backs, we're arguing over the, you know, working capital peg, we're arguing over the multiple and things like that. And so I think it is definitely there, there is, that's the extreme version. The usual version I think that we see is they're coming in and they've gotta ROI the investment and they have, built-in either arbitrages or fixes that will help them hit the goals that they want to hit. And the other thing that I think, and I don't mean to accuse the people in that deal of being liars. I'm trying to just say, I think that they—

this isn't a formal declaration of shenanigans.

I think that they do know, like you said, but they don't believe, or there's a mask over their knowing at the time that they're having the conversations. Or, you know, maybe they just are always eternally optimistic when they're talking to the founders. I don't know. But the truth is it seldom works out that way. And it makes sense that it seldom works out that way because you got to think you're not going to be there ultimately long-term. Even if you are there, the decisions that you made, were you making the decisions and you're not less used to anybody second-guessing you or you having to justify yourself to anybody so you can make some really bad decisions and all of us do, you know, I know we have multiple times for millions of dollars. And so when they're in there, usually debt-backed and investor, you know, funded, they've got to, you know, they've got to hit their numbers too, or it's not going to be good for them. And so they're going to want to be responsible for their accountability, not abnegate the responsibility to you and hope it all works out. And so I get it. I think that's something that a lot of founders would be, you know, and sellers would be better off if they understood it. But I think that the key is that it's not going to be status quo and you should know that. And so what we did in our deal though, that did surprise me Um, and I think, uh, I'm gonna, you know, I'm gonna say, I don't know if we should have known better or not. I mean, I know that we suspected and we went into it realizing that that was a possibility and had conversations about it internally, but we also had multiple companies with multiple contracts, like written contracts that had us continuing to do things. And even with that, it was kind of like, yeah, yeah, we're doing our thing our way, which.

They bought it, right?

That's, that's their right. But, um, but even in that scenario with multiple continuing contracts, a role in our personal brands, you know, it still wasn't what we thought it was going to be. And we were still associated with it. So we haven't gotten to the, the topic at hand here today, but, um, when it ultimately ended because ultimately they, you know, the pandemic happened, you know, thanks again for your internal dreams and fears that caused us to say, let's go on and sell it when we did. Uh, but the pandemic happened, they shut down, you know, almost a billion dollars, I think, worth of acquisitions that they had done, just shut, shut the doors. TNC was one of them. Uh, Traffic and Conversion Summit, the event we sold, was one of them. And, um, and then I feel like that's when, at least when I really felt more of the identity, because it's like, that's not around anymore because when T&C was around, we had people coming to us all the time that wanted access to that distribution channel. And when it was gone, it wasn't there anymore. And so that was an interesting thing. Did you experience anything then in addition to what you had that first year and a half after?

You know, funny enough, I think I had done enough business with it that when it did finally go away, I felt very little. I almost felt a sense of relief and closure in it that it's like, okay, you know, this isn't going to be a path anymore. But I had sort of the only way that I kind of got right with it in the past, because I think I felt the loss sooner than you did and the identity shift, you know, so you were much more a piece of it than I was for sure. Right. Um, and again, I was also trying to do business with the reality that the entire company was going to go, not just this one, you know, piece of it. So I kind of had to, you know, build this, you know, these other lifeboats, if you will, which again, we should get into this. It's something that you should do, like knowing what you're exiting to is just as important as knowing what you're exiting from.

Well, that's where I want to get. So I want to finish this part first and then I do want to talk about that.

But I think that's why for me, I had sort of already shifted my identity. I'd already shifted what we were doing. And so for me, it almost felt like a, okay, cool. I don't need to divide any attention over there. So I I think I felt a sense of relief at that point in time. And it's probably good, you know, as business partners, like, I'm, you know, obviously, like, we're fine and stuff like that. Like, but why it's probably good to talk about some of this stuff if you're in business with somebody else, because I think you and I were going through same things at different times, you know, and it can always feel like the other person, you know, you can almost feel like the other person just doesn't understand or they don't care anymore. They don't, whatever. Like, I think we've had enough trust built up that that never really happened. But, um, I do think it's something you have to be careful of where you have a co-founder situation. Um, especially if you want to keep doing this together in the future.

So talk about that a minute.

Well, I mean, you know, I know when I was like wander, like after the, after the initial sale, when I was kind of wandering and generally worthless, right? Um, you were very patient with me and you were kind of like, hey, we going to do stuff or like what's going on? Right. And you sort of let me work, you know, you sort of let me work through it. I don't know that ordinary, you know, co-founders that didn't have the same type of, you know, history that, you know, you and I had would have necessarily extended that much grace because I, it's not like I ever said, hey, I'm kind of going through some stuff right here. I need, need your help. Like I just was worthless, right?

Well, you were, weren't you also kind of going through, wasn't that around the 40-year-old, uh, man, I had turned 40.

I was just a total fricking train wreck. Yeah. I mean, it was just a, I'm a, I'm a basket of emotions. Yeah, no, it was a, it was, it was a whole, it was a whole thing, but you know, it sounds silly, but just like married couples should go to, you know, should sometimes like go to, go to counseling, even if nothing is wrong, just to have a place to talk about it. I think there's a place for, you know, business couples to just say, how you feeling? Like, what are you, what are you thinking right now? Talk to me about this kind of stuff. Because obviously there's a lot of places where the analogy, you know, stops sharply, but there are, you know, business partnerships are still very analogous to marriages. And so, yeah.

And we've sent people, you know, multiple times to people to talk to that help basically business marriages, right? So that's, it's a legit thing to do. Okay. So, so that's the from our perspective, a couple of things. Now what's interesting for us, I did not have, when I exited the practice of law, I did not have anything in mind. I didn't have, I had other businesses, but I didn't really have another business that was me. I was the managing partner of my law firm. I founded it. I helped build it up. You know, I operated in it for about 14 years and then it wasn't, and I didn't really know what to do. I knew that I had things I was interested in, but I was kind of at sea on that. The difference I think with the exit, like from Traffic and Conversion Summit was we still had Digital Marketer. You still had Digital Marketer. There wasn't like a, Hey, I don't do that anymore and I'm not there and I'd not kind of welcome there. So that's the thing that I see a lot of founders dealing with and it usually manifests itself in negative ways through addiction, infidelity, partying too much, depression, investments. Yeah.

Yeah.

Oh my gosh. The fastest way to lose all the money that you made selling your business is to fancy yourself a venture capital investor and invest in all the startups that your are now coming to you with this. So the positive side though, and I think what really helped with T&C for you and is something that I really do want to talk about here is what are the threads that save you from being adrift on the ice flow of identity loss when you sell that business, close that deal, and get that wire. Um, now what do the people that are happy do? And I have some ideas about it, but I, I, I think you've touched on it, so I'll let you riff on it first.

Well, I think it does, it's, it's being clear on, on one, yes, what your identity is. So what are you going to call yourself? If you're no longer a business owner because you sold your business, then you can't really think about yourself as that. Nor can you be—

I'm the CEO of Digital Marketer. You know, what do you do? I'm the CEO of Digital Marketer. I'm the CEO of Trafficking First. I'm the founder of XYZ Co., right?

Now you can't, you, you can, You can say you're the—

we're the founder, I guess, but that's not where you want to live. No.

Yeah, exactly. And so I think you need to have clarity on what is your identity, which is as simple as, yes, when somebody says, what do you do? You have an answer for it that makes you happy. That makes you proud to say it. Um, and you may not have it immediately day one. Um, but to work in pursuit of that is important because to your point, yes, like we sold T&C still technically had Digital Marketer, but in my mind at the time, that was going too. So I was disassociating myself from that. So as far as I was concerned, it was gone. I didn't even want to claim that. And so that's why I was a bit adrift is I didn't know what to say anymore. Right? I didn't know what to say from an identity. So their identity is definitely a piece of it. What is also though an important piece is just what are you going to be building next? Because I think once a builder, always a builder. And, you know, one of the biggest mistakes, let's say you're okay with saying, I am an investor, right? I'm going to shift from, you know, from running this company and from building this company to I'm just going to be an investor for a while. And that is an identity that you're okay putting on. You know, you mentioned that you kind of struggle with that. Let's live in a world where somebody is okay with that. The reality is, and why that's still problematic, is that if you're a builder, You're going to want to build something. And like my problem was, yeah, we had these other companies in the portfolio, but they were either being run by other people or, you know, I didn't know enough about them to necessarily feel like I could swoop in. It would be inappropriate for me to be like, well, I'm done with this thing. So now I'm going to play with your toys. Like, you don't just get to do that. And so I didn't have anything new to build. And it wasn't until it was like, okay, let's do this. Scalable thing together that's not just investing, right? I mean, yeah, that's kind of the, the, the backend piece that we want everything to flow to, but it is a business again that we get to build together and operate and tinker. And I still want to be able to do that. And I think for the vast majority of business owners, and it doesn't even have to be a for-profit thing, but deciding What is the thing that you're building? Because the people I know who have sold and they're still happy, they didn't just move forward into a new identity, but they move forward into a new activity, a new daily activity. This is what I'm doing now, and this is specifically what I'm building. And if it's not in the business world, it still needs to be something that you feel like is creating this surplus value.

I like it. Yeah, I think the thing that that I've identified is it is fulfillment continuity. And the way that works is that you have to look at what percentage of fulfillment is the existing business that you've got occupying in your life. And if you are a—

And you're referring to personal fulfillment, just so we're clear, not like fulfillment of the end product that the business sells.

Correct. Yes. Yeah. Not manufacturing fulfillment, but on the side because the gap, the identity gap happens, I think, because you're doing something that you feel good about and that creates what we'll call personal fulfillment. And if 100% of your personal fulfillment and identity is coming from the business, then you're in trouble when it gets cut off with a knife and runs off a cliff when you sell the business. So, and even if you have a, you know, most businesses don't have more than about a 1 or like, I'd say most of them don't have more than a 1-year period that you're going to continue to be involved, even if you've got a 3 or 4-year earnout or something like that. They want you out, you know, almost always. And then there are exceptions, but almost always. So, um, so what happens when you are not there anymore? And if you walk in the office, it's kind of annoying for people. And so I, I remember us having, we have a mutual friend that sold, you know, at a, at a good, Price. And, you know, he was saying, you know, I go in the office and, you know, it's like, they don't want me there. It's like weird.

It's awkward.

Like, you know, why are you here? You know, kind of thing. So if that's your, your 100, you know, if that's where you're getting everything, then that's going to be a problem. And so the way to avoid having that be so impactful is to lose, you know, 20% of your identity because you've got other threads that are going on. And so, I like the idea of what are the things that take precedence over the business for you personally? And not that you do them to the detriment of the business, but you don't really move those things. And so I'm curious as to what you've got. I've got, I play now probably about 15 to 20 hours of pickleball a week, and that's, I make appointments in my calendar for that and I don't schedule anything around it. And I've got other people that depend on me. So, That would be disappointing. And it's a, like, I have a real strong goal of where I want to get with that. I have, you know, 500+ synthesizers and musical instruments that would take me 3 lifetimes to learn how to work all of them the way that I would like to. I see that, like, I think actively that's my quote unquote retirement because I could live in there and get lost for hours and hours. Learning is like that. Losing at chess to my wife who's got a chess obsession, that's part of it. The travel, 158 countries and I still have desire to go to the ones that aren't bombing each other right now and go back to several and share it with my kids, my wife, my grandchild. Those are all threads that extend past the closing of the identity of being this business person. And for me, 'cause I'm much less an operator now, it's not as extreme anymore. But I think if you have those things, like the people that I see be successful, or they have the next business they want to do, 'cause a lot of people just want to retire, you know, and, but the people that I know that retire from business that are true entrepreneurs are absolutely bored with, you know, the racing team that they put together, the the golf that they're trying to get down to scratch on the travel. It isn't enough because it scratches a different itch. The, that builder entrepreneur, make things happen, deal maker kind of energy and the fray of that is not to me replicable. It doesn't exist in all those other things. If you decide you want to be a philanthropist and you're going out there and philanthropying all over the place and that gives you fulfillment.

That's awesome. Philanthropying.

That's awesome. But for me, like, I like the idea of that, but I absolutely would miss the battle, you know, and I mean battle in a healthy way. Like, I like the negotiation. I like that interaction. And I watch a lot of people that, that leave have that intellectual fall-off and they just kind of, they just kind of are done. And, and that's, you know, that's sad. So either it's that you've got a menu of things, 4 or 5 things that are those continuity threads that will allow you to be fulfilled doing those things while you find the thing that replaces whatever business gave you. Or maybe you're tired of business and you just don't want it anymore, which is fine. I don't get it. It's not going to be me. But there are people that I see living happy lives that way. So that's, that's kind of my thinking on it. I want to know your thinking on it. And then if you have things like that, that you've kind of got in there for that same reason.

Well, I think what you said there, I think is really, really important, which is figuring out what it is about running the business that is what creates the fulfillment. Because if we just say, oh no, it's just owning a business. That's probably not it. I mean, because you pointed out, like, you enjoy the battle, like the negotiation, like that, that kind of piece of it. That's not really the part that I like the most, right? I like more the—

Makes us good partners.

Exactly. Yeah, no. And yeah, by the way, if you're in business with— if you're a business partner and you have overlapping skills, you know, and your Venn diagram just looks like a circle, then one of you is superfluous. But yeah, and I really like the, like, the creative part, the zero to one, like, let's get this, let's get this new idea going and then helping to build some systems around it and then hand it off. And then once that happened, it's like dead to me, right? I mean, so there are pieces I like. I know people who, what they love, which is what neither you nor I love, but they love walking into a building filled with other human beings that they get to sort of orchestrate. And they like being the conductor of people. And so I just think it's important to know and to be self-aware enough and to acknowledge what is that thing that you like. About what you're doing right now, because there's always stuff that in any given day of the month that you're going to be doing and you're like in your genius zone and you're loving it. And there's always going to be stuff that you hate. And so, yeah, I mean, you know, life is always about trying to do more of the stuff you like and less of the stuff that you hate. But when you think about selling a business completely, the entire vehicle of fulfillment, positive and negative, is now gone. So if you can at least capture that thing that you love, even if it's going to be now exercised through a different vehicle, that's the first step. And I think being able to articulate that, and when I didn't have a mechanism of creativity, like a place where I could just go and build something new, because I also don't like to just do it by myself. I like to do it with some people. I need help, right? And so when there wasn't, you know, a packaging to do that with, that's when I felt the most lost because it's not like I just want to step into an existing business and like operate the day-to-day and start leading team meetings. I hate that. Now, our other business partner, Richard, that's exactly what he would want to do. And as long as frankly, he could go and find some people to boss around, he'd probably be perfectly happy and fulfilled. You know, I wouldn't, you know, for your thing, like you want to see, like, I want to, I want to tinker in a bad way, but you're like, I want to be able to get in and fix the things that are broken. I want to see how we can take this thing to something new. And so you're more puzzle solving and problem solving. So it makes sense that the activities that you've chosen have to do with that. I'm really currently struggling a little bit, and I'm where I'm kind of outside of business to find that fulfillment piece. And a lot of it's because, one, I'm we got the business and I'm able to, you know, play in. So, I mean, I've, I kind of got that back in a company, but outside of that, sort of thinking about the avocational stuff, not just the vocational, you know, for me, my primary outlet is, you know, my kids and kind of what I'm helping to create with them. And I'm going to go through probably another just total emotional crisis when we're full-blown empty nesters, I guess, um, which is only a few years away. So stay tuned for that one, Roland.

It's kind of good with 4 kids, 2 years apart though, you know, each of them 2 years apart because You're getting, you know, a 25% reduction, you know, kind of weaning off, right?

Exactly. It is happening. And we are at the point now going back to like something that's analogous to when the businesses, you know, when you sold the company and you come back in and as the boss and people don't, they're like, why are you here? I love my oldest very, very much. But when he comes back from college sometimes and he's like in the house, like for the first, it's like, yeah, I'm so happy to see you. And after a while it's like, All right, dude.

I mean, that absolutely happened with us too.

Oh, the Katya. So anyway, so all that to say, like, I'm glad that I've been able to sort of check that box in this, you know, in this new business. But, and I think I would struggle to do it in a philanthropic or a nonprofit thing. Because what I like is creating something and seeing if somebody wants to buy it. Like, that's the exciting piece for me. Like, does anybody think enough of this that they're willing to give some money to it? So I don't really get a lot of juice from philanthropic stuff. I mean, I'm— it's a different thing. You get it.

I know you enjoy it and you do it, but it's just not the same. It doesn't scratch that itch.

Not even close. And I don't know that I would necessarily be able to find— like, I love golf, but golf doesn't check that box. It doesn't scratch, you know, that itch. So I've just kind of accepted the fact that I never want to retire. Right? I mean, like, it's why when we were talking about the scalable company, like, what would we sell it for? It's like, what if we just didn't? You know, what if this was the goose and we sell the eggs and we just keep owning the goose? Because the goose is what allows us to, you know, that company is what allows us to keep doing the stuff we want to do.

Yeah. Yeah. It is, you know, for me, like learning, I'm a voracious reader, consumer. I know you are too of everything. To learn about everything. And it is such an awesome laboratory to have the company that lets you look in under the hood of so many other businesses that like, I would really, really miss that. I don't think it is replaceable with any of the things I do or anything I can imagine doing. What I do think though is that there's more room to do those other things. And as you exit and have more cash that's not tied up in companies or in one company, and you have, I've watched that like where 100% basically of my net worth was in the company to, oh, I can finally take the house and buy a house that I deferred and that, then I had the house and then you start to get a little bit of cash built up and then you make an investment or two. So it's interesting to watch that percentage and it's still for all of us because we are effectively like private equity. Our investments are not typically the stock market. Our investments are the companies that are in our portfolio, which return way better. But the same that like watching that percentage go from 100% of net worth in businesses and zero to, you know, 50/50 or 75/25 or whatever. The same thing is, I think for me happened in fulfill— in the fulfillment. Like I don't want to do, I like when you and I first got into business and you had War Room, which I came into and I was like, we could grow that. We can expand it. We can do 17 of them and we can do a lower War Room and a higher War Room and this, that. And then you, and it was so frustrating for me coming into that because you had lived it already for,, you know, a decade, I think, before I came in. And, um, and you were like, man, I don't want to do that. It's too many days. And I was like, what the hell? What do you mean? You know, like, that's, that's what we do. And you're like, nah, I just like, I don't, I don't like it. You know, I mean, I don't like it being that much. And then I've got a travel day, you know, on the front. And so it's really 4 days, not 2. And, you know, we do it 4 times a year, then that's, you know, so many days. And then I have to get ready for it and all that stuff. And I felt like that at the end when we, you know, ended War Room, I felt like I really don't like going to these things anymore because of all the things that you said. And so I think that what I've experienced is, and I am getting to a point, is that just like that allocation of capital, in net worth, for me it changes. And right now, like, I'm kind of like, I'd be happy with 60% business and 40% all the other things. But I don't think I could cross over that 51%. I think I need control. I think that business needs control, you know, voting control of my personal life to have fulfillment. I'm kind of curious as to like, do you have, things like that. Like, man, I wish I had, I would like to allocate, you know, 20% more of my time to art collecting or something like that.

Yeah. And I think that's called growth. Like that should change over time. And that's how, you know, you're kind of growing as a person is your personal resource allocations, both in terms of where you're, you know, putting, investing your money and also where you're investing your time. Um, you know, where my piece came from was I was kind of looking at these kids getting older and I was like, I just need a lot more time to invest in them because the business is going to occupy a significant amount of my time. That's okay. You know, they're in school, adults work, like that's fine.

And you love it.

Yeah. And I love it. Exactly. So, um, I, I have no problem whatsoever, you know, working. People would ask me, they're like, you know, how much do you work? I'm like, I work all day. Like, I mean, I work every day. Like, that's, you know, they're like, oh, but, you know, aren't you able to take off? It's like, yeah, I mean, I can, but I don't necessarily want to, you know, I got stuff to do and I like it, but I want to have the ability to invest more in the kids. And I wanted to have the ability anytime, you know, one of my boys asked like, hey dad, can we play golf? To say yes. And so for me, it had to do with being able to allocate more towards the family. Peace. Because I didn't feel like for a very long time I was allocating enough, certainly not enough for me. I want to be able to allocate more. And I also knew that my ability to do that was going to be limited because they're going to leave. You know, they're selfish and they're all going to start their own lives and go off on their own. And so that, that's really what it came down to. But now what I know is I'm getting to a point where the kids are getting older. They are starting to go off. Like my, that, that time is going away, which is opening up more time to do things like speaking and consulting days where before I would have been like, nah, I don't want to do any of that. Now it's like, okay, I can do more. And so I think it's about just finding, being intentional about what is appropriate for you now in this season and then pursuing that intentionality. I think all too often, nope, people aren't intentional. And then if they do have a sense, they don't work towards what they would like for it to be.

Yeah. Yeah, I think so.

Yeah.

So what are the things that you think you would expand if, as the kids move on, you have obviously lots of interests, would you devote more time to the business stuff or are there other things that might be threads that you would want to pull on more?

I would actually probably devote more time to business stuff than I'm devoting now. I mean, right now we take We do take a lot of vacations as a family. I mean, again, that's where I am right now. And I don't regret or resent like any of it, but there's also some cool stuff that I want to do that I'm having to say like, I can't really do that right now. You know, my, there, there are, there's speaking engagements, for example, because I do enjoy public speaking.

I enjoy getting out there and you enjoy teaching too, because I could see you as a professor, you know, with, you know, doing that more.

And that's another piece, the ability to teach, whether that's a formal teaching type position or just doing more of the type of speaking that I like to do, which is teaching, not going out there and doing a motivational talk or something like that. I enjoy that. That's fulfilling. And right now I've got— I mean, I literally just had a speaking request come in, and I'm like, no, I can't do it because it overlaps with the family thing. And again, I don't regret that at all, but it's like, it's a bummer that it overlapped because I would have liked to have done it.

Yeah.

You know, and so having more time to do that, I do enjoy when we get to work directly with clients and solve their specific problems. I see that as like entrepreneurial grandparenting, you know, where it kind of, you get to play with the kids and then when you're sick of them, you get to send them away. Um, and so it's fun to get to do that with other people's businesses and to be involved and to be able to give your advice and suggestions. And if they take it, great. And if they don't, that's okay too. Um, you know, just, you're there and you get to stay in it. So I look forward to being able to do more of that. Right now, that's a relatively small percentage of mine, of my time. I'd like to do more like art collecting. I'd like to do more, play more golf. My golf game is just in the toilet right now because I don't play enough. But yeah, mostly it really is kind of on the business side of just getting to do the stuff that I'm good at. We travel a lot. I don't know how much more we could frankly travel than we're traveling right now.

You've done a lot.

Yeah.

I look at your schedule and I'm like, oh man, I don't think I'd want to go that way.

It's a lot.

Yeah.

But no, I, what about, I mean, is there anything else with you?

That's, that's pretty much the things that I, I said. I, I enjoy teaching, so I like, you know, I like the ability to create content. So having a little bit more time to be more intentional about that, you know, we, we obviously have it as part of our business, but, but there's other content that I would like to create around music. And I know, you know, I made the decision a long time ago that I couldn't, make money at the level that I wanted to from music. It wasn't likely, you know, my odds were not, not such that I felt like it was a good thing to put, you know, to go all in on. But I really do enjoy it so much. And I don't get to spend nearly as much time. I, you know, even as playing, you know, like, not just because there's two things, there's like all the knobs and sounds to create and sound design, but then there's also composition, and then there's just playing. Like, I would like to be a significantly better piano player than I am. I would like to be a significantly better pickleball player than I am. I would, you know, like, there's those things like I'd love to, you know, have the time to play chess and golf because I like both of those things require a lot of time. And I just, I know I'm just going to be frustrated doing it because I can't, I can't give it what I need to give. So there's a lot of things like that. And then travel for me, you know, I am very, very comfortable traveling. I'm very comfortable, you know, living in a place. I would love, I know you guys have talked about, you know, moving to the, out to the Cotswolds or to Yorkshire, I think it was. I would like to, you know, have a multi-continental lifestyle. And it's hard to do with the business commitments that we have right now. So there's things like that I think that would be really, really cool. But the gist for everybody that's listening, just so it's not a Ryan and Roland personal development session, is that those things that we're talking about have helped us through multiple exits and kind of identity shifts to have some base that we can hang onto while We are losing parts of ourselves and I, and you are, you are consciously, willingly giving up a part of yourself when you're taking the thing that you've built and created and, you know, that has been your identity and shifting to something else. The key is it needs to be a shift and it needs to exist before the cutoff, um, or you're going to be lost and unhappy for a period of time that you may or may not recover from, and that is not necessary because if you plan for it in advance, you won't have that. You'll have a feeling of, of loss, but it's going to be significantly lower impact on your life because you have all these other threads to lean on while you're finding whatever scratches the itch that maybe you don't scratched by the thing that you sold. That's to me the big thing to take away from it, I think. What are your thoughts?

I think the most kind of sad, pathetic creature is the miserable rich person. Yeah.

And yet, if you have the ability to finance your downfall, that's a terrible thing.

Yeah. Money buys you a lot of things, and I'll tell you, I've been rich and I've been poor, and rich is better. But Uh, and, and while it doesn't, uh, you know, it, and it can bring more happiness if you use it as a tool, which means you got to know what you're building. Um, cause if you just got a fricking hammer and a, you know, saw and you don't know what you're building, then, then they're not helpful tools. So hopefully, yeah, what we talked about will get people thinking now, cause this, this is all useful stuff to think about now, even if you haven't sold your business, just asking what specifically about my, my business brings me joy now? And what's the stuff I don't like? Because if what you can do, if you can identify that earlier, not only can you know how to redirect the resources that you're going to have post-sale so that you can continue with the fulfillment and continue being the happy person with more resources, you can also build a much happier, more fulfilling job, for lack of a better term, for yourself right now. I mean, one of the exercises that I do just about every year is I reevaluate What was the work that I did this year that I liked and what was the work that I didn't? And I will fire myself from my current role and I will rehire myself. I'll write up a new job description. I'll rehire myself into whatever this new role is. And I won't necessarily make a big deal out of it to the team, but it's for me, it is this, it's almost like a ceremony that I go with internally of like the firing and the rehiring of myself to be intentional about the role and my identity within the company. So this is something that you can do now. And if you do it now, you're not only just going to be better set up for when you do exit, you'll just be better set up for operating your business today.

Yeah, I love it. Well, hopefully that was helpful to you guys. Um, if you enjoyed it, please share it with a friend, uh, or several friends. And, um, um, hopefully it gives you something that you can actually use in your business because this is, you know, and, and in your life to be happier because that's kind of what we were after. When we started thinking about this topic. And we'll see you next time on Business Lunch.

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