Ep 481 After the Deal: What 70 Founders Reveal About Generational Wealth, the Achievement Trap & the Happiness Illusion
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Hi there, and welcome back to another episode of Built to Sell Radio, the podcast designed to help you punch above your weight in a negotiation to sell your company. I'm the executive producer, Colin Morgan, and today we're welcoming back John Rood, who first appeared on episode 437, Escaping the Service Business Trap, where he shared how he built Next Step Test Prep into a multi-million dollar business before selling to private equity in 2018. But

But instead of jumping straight into another venture, John took a step back to study what really happens after an exit. He interviewed 70 founders for his new book, Beyond the Exit. And what he uncovered challenges a lot of assumptions around generational wealth and what makes founders happy. If you're thinking about selling or already have, this conversation will give you a fresh perspective on what really matters after the deal. Without further ado, here is John Rood.

Enjoy. John Rood, welcome back to Built to Sell Radio. Hey, John. Nice to see you again. Yeah, good to see you too. I mean, we had a really good chat. Gosh, it must have been several months ago, maybe five or six months ago about your business next step test prep.

This was a test prep business where people would, well, you know what, you describe it and just maybe encapsulate the exit as you remember it all these years ago. Sure. Yeah, I'll give you a quick overview. So I in, geez, it's such a long time ago now. So in 2010, we created this business. And the background of it was that I had been in management consulting for three years and

And it just got to the point there where in management consulting, it's like kind of like up or out. And I was not going to go up any more there. And so I decided that I would kind of try my hand at being an entrepreneur. I had no idea what I was getting into. I had no like lifelong aspirations to be an entrepreneur.

I had basically no skills to do it. And so what I decided to do was, you know, I had worked in the test preparation industry as an instructor and I made $20 an hour with that, which was the most money I had ever heard of anyone making in my whole life. So I thought that was a pretty good, pretty good industry to get into. So we started a little company there. We ran that through kind of all the ups and downs that you might expect in your audience going through right now. Then in 2018, we sold that to private equity.

Got it. And that exit, remind me just some of the metrics. And the reason I'm asking around this is because I want my listeners to understand sort of the financial impact for you personally. Yeah.

Just talk about how big the business was and however much you're comfortable sharing around the valuation. Yeah, sure. So we were single-digit millions in revenue and single-digit millions in earnings. I don't really get into the valuation stuff publicly, but it was a substantial exit such that I've got pretty good freedom now for what I want to do in life. Got it. And so you crested the point where work became something...

you can want to do, but don't have to do it. Would it be fair to say that? Yeah, I think it's fair to say, although it also say, you know, to the audience, um, that point is, is really variable. Um, and that's, that's totally at the, at the mercy of how much you want and need to spend. And, um,

I remember once early in my career, like before I sold my business, once I was in a conversation with a guy and he said, you know, all I need to do is earn $20,000 a month to support my lifestyle. And at that point, I was 25 years old. I was like, oh, my God, like $20,000 a month. That's like...

That's incredible. That's the hugest amount of money I've ever heard. You spend it every single month. And now that's gotten a lot easier to spend that kind of money on a regular basis. But, you know, that's why it's really about what do you need in your life? Like, how much do you need to spend? Where do you need to live? You know, how much do you think it costs to raise your kids? How much do you think you need to give to your kids when you knock off this mortal coil? All of that's pretty flexible, I would say.

And some of these questions you delve into in the book, Beyond the Exit, there must have been something that happened in your life post-exit that was so meaningful, so transformative that you wanted to write a book about it and talk about it publicly. So what happened?

Why write the book? So to me, it's a couple of things. One of them is totally selfish, which is one of my goals in life since I've been a little kid was to write a book.

And, you know, in our test prep business, we publish lots of test prep books that, you know, that mostly my team wrote, although my name was on the back of some of them. And I just had not done, had not written a book in life and decided to do it and started to think about like, well, what do I know? You know, what story can I tell? What can I impart? And I thought, I remember thinking this, I was like, well, I could write, you know, like the 100th book

on implementing like traction and KPIs or whatever. Like, yeah, I could write that book. But this was something I knew really intimately. And it's funny, at the time, when I started to conceptualize this book, it really felt like no one was talking about

the challenges as well as the opportunities in the post-exit life. And now, two years later-ish after I started the project, it seems like a lot more people are talking about it, including you and your audience. But I see a lot more of it. And so I'm happy to have the book out, happy to have done it, and happy that that's a broader conversation now where it doesn't feel like, oh, this is the only guy who's talking about it.

Yeah, yeah. No, for sure. It's certainly come up a lot on this show. We've, as you know, dedicated a whole series to the topic because it's one that is important and not talked enough about enough, but certainly getting more sort of awareness in the community. So talk me through your own personal experience exit. Like what sort of emotions did you go through? What was the impact on you personally? Sure. So

You know, one of the things I didn't know to expect was, you know, when I sold to private equity, I kept working there in the business. So it's funny, like the, you know, the day before I exited, the day after I exited, my job title was totally different. My responsibilities were totally different, but I was still going to work, you know, every single day. And I worked there for two years in that business. And then, yeah,

At the end of that, you know, it was just time to move on and time to start thinking about what I wanted to do next. And one of the funny things looking back, which is...

like both surprising for me personally and kind of embarrassing is when I started to think about selling the business, I don't think I really sat down and thought, what am I going to do after this? Right. I thought, you know, I'm going to, you know, these guys are going to keep me on for a little while and keep working in that business. But after that, what am I going to do? I don't know that I ever really sat down and thought about it in a systematic way. Um,

And, you know, inside our business, we do tons of planning. We do our annual goals and our quarterly goals and our OKRs and whatever, whatever you want to call them. But I didn't sit down and do that for my life. And so actually one of the reasons why I wanted to write about it was to encourage people to work on that process and to start working on it well in advance of actually being out of their business. What was that like for you when you actually sat down and do it? When I sat down to do it, it was...

It was surreal, I would say. Like sitting down with a blank piece of paper and trying to figure out what to do with your life as a... You know, I was in my late 30s, I guess. It's very unusual because the things that we're programmed to do...

There's lots of good reasons not to do them. Right. So, for example, you know, the most obvious one being, you know, everyone's got their non-compete and I don't want to go back into that. I would not go back to that same business I was in one way or the other. But, you know, you can't be in the niche of your industry that you've been in. And that's where all of your personal connections are. That's where your professional connections are. That's where you understand the market and the opportunity.

And so you start thinking like, okay, well, you know, what other kind of business should I start? And I think that's a really natural inclination because we're entrepreneurs, right? And that's what we do. That's our identity. That's our expertise. And you start to think about that and you start to kind of like,

It catches up with you a little bit. Like, wait a second. Like, I don't I don't need to do that. Like, why am I voluntarily doing this thing, which I personally remember being remarkably hard and stressful? And I'm going to go do that in a situation where, you know, I wouldn't say that for

for entrepreneurs is all about the money, but it's at least in part about the money. And I just didn't need it. And so part of what I write about, and I interviewed 70 other entrepreneurs as I worked through this book, was kind of those stages that people go through where you sell your first business, you get out of it, and then you sit down and you're like, I've got a list of 35 other business ideas. I'm going to go do them. And then

And then maybe you do it or maybe you don't, but there always comes a point with entrepreneurs in my experience where you just say like, why? Like, why am I doing this? Like, what's the meaning in me creating another industry or another business in like whatever industry that might be in? And that's a real kind of soul searching moment. That's actually, I think, a harder moment than...

for people that like leave their business then or say like, okay, I've got my, you know, I've got my spreadsheet of 30 business ideas. I'm just going to do one, you know, automatically. Right. Cause that's like what, that's how we kind of flow into the next thing. That I think is the big challenge is kind of getting, getting over that hump and saying, I, you know, I don't need to do another business. What's the utility in my life of doing that? What did your research show about people who did go back in the same industry they left? Yeah.

I talked to a couple of people that had done that. And I think it's, I think some of them were just very comfortable in that world. And that makes total sense to me. I think, you know, as human beings, we develop our expertise and we develop, you know, we, that we have the skills and we have the expertise that we have, and we like to put our skills to the test, right? Like it feels good to do something that you're good at fundamentally. And so for a lot of those people, I think that

They got to continue going down that road and they keep doing it. I think for all of us, there eventually comes a time when we look at that and say, what are we doing that for? And for some people, that comes earlier than others. I interviewed one guy. We didn't write about him explicitly in the book, but he was...

I'm trying to think of what he even did. He was in the food industry and he would buy a food business and then run it for a few years and then sell it and then buy the next one and sell it and did it over and over. And so one thing I asked everybody in my interviews was I said, like, what's, what's the end of this process like for you? Like, when are you going to say I've made enough money in the food industry or whatever, and now I'm done. And he said, I think I'm going to die doing it. And I, I was surprised to hear it. Uh, that was surprising to me. Um,

There's an author, I'm sure you know his work. So Bo Burlingham wrote Finished Big, a great post-exit and exit planning book. And he says in the very beginning, you're going to exit your business eventually one way or another, even if it's in a body bag. And I'm...

And so I think that's really true. Obviously, that's really true. And so thinking through that process of like, wait, you know, do I really want to be doing X, Y, Z for the rest of my life? Like, that's definitely a wake up moment for people. And in your case, you thought, well, maybe I'll do another test prep business. I've done MCATs, I've done LSATs, maybe I'll do whatever, GMAT. But you chose not to do that. Yeah.

Yeah. I mean, I thought about like I'm not interested in going into exactly those niches, but I thought about some kind of an education business in K-12 selling to schools or something. And, you know, it's possible that I could do that. Like I have the tools to do that again. But it just seemed like that wasn't that wasn't the way for me to grow personally. That wasn't wasn't on my dance card.

So what did you decide was on your desk? So there's a couple, so there's a couple of things. One of them is I try to manage my workload and workflow kind of around the rest of my life. And I try to be really meaningful about that. So, you know, I've, I'm, I'm early forties. And so I'm generally okay to good health. I've got little kids and I,

I saw it the other day, like I saw this, this graph and it's like graphing out the amount of time that you spend with your kids. And it turns out, yeah, you've seen this. I know you've seen this. And so it's like, there's like this remarkable statistic and I'm going to mess it up, but it's really close, which is like, by the time your kids leave for college, when they're 18, you spent something like 80 or 85% of all the time you're going to spend with your kids in your entire life. And I saw that as like, you know, my gosh, like I need to be prioritizing that.

among all these other things that I'm doing. And so I wrote this book, which is great. That was a great project. I'm almost certainly going to keep writing books just because it was so much fun to do it. I've got a little business in the AI world that I run with an old buddy of mine. That's pretty interesting. And I do it because I think it's interesting and I think it's fun. But as an example,

two years ago in that business, or maybe it was last year, I got invited to speak at a conference. It was like a big conference and it would have been good for the business that we have. And so I asked like, okay, like what's the date and what's the slot? And they said, well, it's in, you know, North Carolina or something. And it's October 31st and it's at like 2.30 PM. It was like, no, I'm busy October 31st. Like I have like 10 Halloweens with my kids and that's one of them. And I'm not going to miss it to be at that conference. And, you know,

You know, if it had been my first business, I would have said yes, because those are the sacrifices that we make. But when we get to a point where we don't have to make as many sacrifices, I think those are the things I try to be more mindful of. It sounds idyllic, you know, the idea of being able to prioritize your life. What's the expression? Work to live and not live to work. I'm getting that right. The idea that priorities that you have come first and so forth.

But it can't be that easy. I mean, you know, we've interviewed folks on this show who've had real difficult periods after selling their company emotionally, psychologically. I mean, it sounds too easy than it possibly can be. Like, what's been your experience? Like, you know...

I think for a hard charging type, a achievement oriented, which kind of by default, you have to be to build a business in your case to millions of dollars of profit. Isn't it kind of hard to turn all that stuff off? Yeah, it absolutely is. And I think that's the struggle that I for sure have gone through. And I know that many of the entrepreneurs that I spoke to go through that struggle as well. And I think in part,

there's a grieving process to go through for the part of you that has to be a hard charging entrepreneur. And it's a totally voluntary process, which is why, in my opinion, so many people just like go back to work, like as soon as they possibly can and work as hard as they can on whatever the next thing is. Um, lots of people do that. And, you know, I have no judgment. That's, that's totally fine for people that, that want to live their life that way. Um, when

When you decide not to, I think there's a grieving process that you have to go to where the things that sustained, especially your ego, have to change. We're used as entrepreneurs to our businesses growing every year, that every year we're doing something that's bigger and better.

When we leave our business, the same thing happens to everyone who exits, right? So your friends come up to you and talk to you or you go to your relatives for the holidays, your in-laws or whatever, and someone asks you, what are you going to do next?

And it's a loaded question, right? It's not a straightforward question. It's a loaded question because the way that, whether it's meant this way or not by the speaker, the way the entrepreneur interprets that question is whatever's next has to be bigger and better because that's what we're used to, right? Like, you know, you'd never have a business be like, well, my business is going to decline 10% next year. Like that's my goal is decline 10%. Like, no, it's got to be, it's got to be bigger and better. And eventually you have to learn that

There just is no bigger and better, right? You can have a larger business. You can have a second business, a third business, a fifth business, like whatever. And certainly I know people that have done that. But if you weren't happy with the first one, you're not going to be happy with the 10th one. I love this quote from Naval Ravikant, who a lot of your listeners will know. He says, if you're not happy with a coffee, you won't be happy with a yacht. I just love that quote. I think it's exactly correct.

Interesting. If you're not happy with a coffee, you won't be happy with a yacht. Yeah. Yeah. And you learn to appreciate the little things. Right.

Yeah. And, and for us, it's funny, like the things that we can appreciate are not, are not little. I said, what you said is correct. But like, if you, let's say someone hypothetically, not me, but someone hypothetically, they exit for $50 million or whatever, like whatever the number might be. And then they say, you know, and then like, you know, their, their mother-in-law comes to them and says, what are you going to do next? I hope it's bigger and better. And they're like, Oh my God, like, how am I going to create a $500 million a year company? But if they do that,

There's nothing there. There's nothing bigger and better in it. It's just more. It's just more of that of the same. Like there's nothing more that they can buy. I mean, maybe your private jet guy will correct me, but like there's very little more that you can buy. There's very little more that you can do. So that's I think part of it. And the other part of it too is we're used to being important people. And I think that that's,

The day that you stop running a business, your importance to the world goes down so much. And then you ask your therapist, of course, your therapist is going to say, well, you're still enough. And that's true. And that's what we have to... We have to earn our way to that. But there's so many stories in my book of someone who... Maybe they sell and then they get fired by their new owners or whatever. And this guy that I met who's a professor now and a good friend of mine now here in Chicago, he says...

you know, the day that he's that, that he left his business, you know, you expect that the phone will keep ringing. And it just never, it just never does. Right. Like, you know, one guy who sold a business told me that he thought that like good morning, America was going to call and have him on to talk about the sale of his business. And I, he was kind of joking, but at the same time, you think like, well, you know, wait, I did, I did a really big thing. And now I'm going to be like a little bit famous here, but no, no, no one cares. Like people have,

seven, eight, nine figure exits literally every day. Most of those people are not going to be celebrities. So there's kind of like a death of that ego that has to happen. Some people listening to that probably feel a visceral negative reaction. Like the idea that you would go from

Because some people, they would say, look, I derive an enormous amount of satisfaction from life by achieving goals. Yep. Right? So it doesn't have to be in my current business. But if it's not in my current business, I want to be achieving fitness goals. I want to do Ironman. I want to write a book or I want to do like, but there are...

it's that adrenaline rush they get from setting and achieving goals and they're hearing you say your ego has got to die and it's like i couldn't exist in that world without that achievement so how do i get over my ego like what's the what's the do you know what i'm asking that's a great question yeah no i totally i totally get what you're asking um i think that

For those of us who have been very type A and goal oriented, it's really tough to let go of it completely. And I think that you don't have to. I think you have to let go of the kind of the business ego eventually to get on to kind of what the next thing is going to be. And so here's some examples. So

I interviewed one guy who sold his business. And I think that the headline price was like $700 million. And he had a partner in investors and whatever, but like he had a very, very good exit. And one of the things that he'd always loved doing was martial arts. So he didn't have that much time to do it when you're, you know, you're running a business. And, and,

So like for me, it's like, okay, like I like to play tennis. So I like kind of go play tennis at the club twice a week and hit it around a little bit. He went and got like an Olympic level trainer in his martial art and trained full time, like 40 hours a week.

And I think that's incredible, right? So that's like an incredible way to take that energy. And of course, some of that like financial opportunity that he's got where he can hire a guy full time to do this and really go hard at something that's totally different. That makes total sense to me.

Isn't that like the alcoholic just trading like scotch for gin? It might be, it might be, but I felt like he really liked it. And then another guy who I interviewed, I really love his story. His name is Jim. And he had a big like IT consulting business back when like you could get paid all this money to go put software into companies, blah, blah, blah. I'm sure you still can today. But anyway, it's a long time ago, sold that company. And then kind of like,

like futzed around with stuff for like eight or nine years, I think. And then one day decided that he would, he would, he wanted to go to this like, like knife conference, like pocket knife conference. Cause he always liked pocket knives. And he's like a knife guy and a watch guy, whatever. And he meets these guys from, I think like Denmark, like some like Scandinavian country. And he ends up partnering with them.

And they create this pocket knife business. And actually, I got one. I got one for Christmas. So I've got his pocket knife like right here. And they won Blade of the Year. And they're an Inc. 5000 business now. And what I think is cool about that, it's not like like, yeah, it's cool that he built like a successful business, but it's a thing that he really loves to do. And he loves the topic area in a way that like I don't think that he loved before.

software installation. Like maybe he did like a little bit, but not the way he lost knives. And so when you think about like, what are you going to do with this big ego with this drive? Like it's about finding a thing that you can point it at that creates a lot of meaning. Maybe it's a business, maybe it's a hobby, maybe it's a nonprofit. It's definitely something like it's not sitting around like on your couch. But that's like, that's I think the struggle that people have to go through. How old are your kids? My kids are nine and seven.

Okay. So pretty influential times. How did you think about the impression you wanted to leave with them as it relates to hard work? Because I know a lot of entrepreneurs work because they want to set an example for their kids.

And even though they might not have to work as hard as they do, they want to show up and look like they're working hard. So their kids see someone working hard. So they instill the values of hard work on their kids, even though financially they don't have to work quite as hard anymore.

Did similar things kind of come up in your mind? How did you kind of reconcile that with the, I'm going to go to the 10 Halloween events because I'm not going to the conference. Because eventually the kids are going to figure out dad seems to prioritize us over work. Yeah. Yes. Oh man. I have so many stories that I could tell about that. Let me tell two stories about it. So one of them is...

I was doing a little like kind of like exploratory consulting work with a private equity firm. And so they invited me to come to like one of their big events. And so they're like their big partner, their main partner is speaking. And I won't I won't name drop him, but he's a he's a billionaire many times over. Like he does not need to work 10 generations in the future. His family will not need to work.

And he was talking about this issue and he was saying that he wanted his kids to see him go get up every morning, go get on the commuter train and go downtown to work. He thought it was really important for him. And I was listening to that. I was like, this is like one of the richest people, like, I mean, one of the thousand richest people in the entire world. And still, still feels the need to go do that. Now, if that was his sole motivator, he could go downtown and just like stop

hang out in an office all day and like watch TV. You could go downtown or like just go to the country club and while away the days, right? Like, and just come home at seven o'clock. Hey, it was a hard day at the office. So when I hear people say that, I think there's probably more, there's more there than meets the eye. I don't think anyone is putting in 60 hours a week for their kids. And maybe that might be a bold claim.

that's how I feel. And the reason I think that is because if you look at any evidence about what's good for kids coming up, having parents around is massively beneficial. Having parents spend time with kids is massively beneficial. And I have seen basically no evidence that says that

parents being out of the house like 60 hours a week, like on the road four days a week, like doing consulting in Cleveland or whatever. Like I just haven't seen the evidence that that's that benefits kids. And when I think about what lessons do I want to pass down the lesson of.

earn as much money as you can and work as hard as you can, like forever until you have a heart attack and die. That's not, that's not, that's not the lesson for me. Like to me, the lesson is family is important. Balanced life is important. Health is important. Um,

Those are the things I think are important. Coming now from a very privileged point where I can say those things, knowing that like my kids are going to eat like no matter what. So I recognize it's a nice thing to have. And if I was, you know, grinding out a sales job for, you know, for 90k a year or whatever, like my attitude would have to be different.

Yeah, yeah, for sure. And at the same time, you know, I just did this interview with Preston Holland. It'll have gone live by the time, you know, this interview goes live. Preston Holland is a guy who writes a newsletter called Private Jet Insider, and he's got a whole following around his business, which is advising people on buying a private jet.

And you can imagine the circles he runs in. It's all kind of YPO and Tiger 21 and all the sort of super wealthy entrepreneurs who, in most cases, can't get off the hamster wheel. Like he told a story of entrepreneurs who've sold their business, cocktail parties that he's been at where, you know, they quietly tell him,

you know, like I could never just live off my capital. Like I want to, I want to build the next thing. And they're on this sort of hamster wheel. And, and I, I'd imagine there's some of my listeners who,

who feel the same way. They've got an exit in mind. They want to build, sell, and they want to go do this again and go to fancier parties and drive bigger cars and maybe one day buy a jet or a fractional jet car. Because they want to live a life that is very glitzy and connected. They want to get invited to the inauguration. They want that sort of life that they feel is a big life.

What advice would you have for someone thinking that way? So, first of all, that's totally OK. And that's not that's not what I want. But I think that different people want different things as long as they have kind of examined what the point of it is. Here's here's what I mean by that. I.

thought when I started to do my research that I would have to like kind of like bucket my research subjects into a size of exit and that size of exit would dictate what kind of problems and opportunities they had. Um, and I found basically none of that. So the problems and the opportunities that people have are fundamentally the same from $10 million exits to, you know, billion dollar exits. Um,

You can spend more on things. At a certain point, you have to kind of try hard to spend more money on things. But the problems are the same. And I read about this story in my book where Larry Ellison, the founder of Oracle, was going to launch his new yacht. And one of the Microsoft guys, like Steve Ballmer, maybe the other, not Bill Gates, one of the Microsoft guys launched his yacht. It was like X number of meters. And then...

Larry Ellison launches his yacht like a week later and it's like in secret he made it like five meters longer just to piss off the Microsoft guy right and so at the very top level like the very richest people in the entire world it's still not enough so if you're the sort of person that's comfortable kind of saying that and saying like I don't there is no enough for me like I can I need more power and more money and whatever and that's what drives me like that's that's totally fine

The lesson I want people to realize is that

It's okay to say that there's not an enough for you. But the trap I don't like people getting into is the feeling that whatever the next milestone will be, that will be enough because it almost never is, right? Someone has $10 million in the bank. It's not enough. Okay, now they have 20. It's not enough. Now they have 40. It's not enough. And there's this really good research that I write about in my book and it came out of Harvard. And it's talking about how at every level of the wealth spectrum from like,

truly poor people to like the global elite, if you ask people how much money would make them feel comfortable, it's always twice as much. Someone who has $100 in the bank, if you'd say, I need $200 so I can eat this week, that's what they want. If you talk to someone, they say, I've got $50 million, but I can't get into the private party with the jet guy. I need 100 to go to that private party, right? And so...

At some point, you have to decide to just get off that and be happy. So if people are listening to this and they're intellectually understanding what you're saying, like clearly if Larry Ellison and Bill Gates or Steve Ballmer or whatever are arguing over the size of their yacht, then clearly I get it. I believe you that I'm never going to feel satiated by anything.

Like there's no revenue band I can get to, no EBITDA multiple I can get to that's ever going to make me feel happy. So they understand it intellectually, but they can't give it up. Like they don't know how to turn that off and say enough is enough. What practical tools, what questions, like how can you get someone to

off the never enough sort of hamster wheel. Yeah, totally. So I think therapy and coaching is an easy answer, which I always recommend to everyone. There's a couple of exercises that I put in the book for this. And

One of them is this kind of like life visioning process where you do this thought process. So if you've had an exit and you think, okay, I'm going to start another business and it's going to take me 10 years to build that business and I'm going to sell it. I'm going to be twice as successful. So previously I sold for, you know, 10 million. Next time it's 20 or 20 or 40 or whatever, whatever the numbers are. And so you say, okay,

In each area of my life, right, I've got, you know, my family life, my health, my professional life, my financial life. What is going to look different in 10 years if I have twice as much, right? What is that actually going to look like? And, you know, for me, if I sit down and do that, it's like, okay, my family life will be exactly the same, right? Like, because all I want in my family life is for my kids to go to like a nice school, for them to live in a safe neighborhood, right?

a warm house like it's it's six degrees out my kids are warm they're learning like they're fine that's all i want for them right like like more money or prestige for myself isn't helpful um you know what do i want in my professional life well personally i want time flexibility and i want to work on only projects that i like and with only people that i really enjoy working with um

And I do that now. And having more would not be helpful for that. Now, I totally agree with what you said, though. There's definitely people that would do that process and say, well, I get to go to this level of political fundraiser, but I want to go to the next level of political fundraiser. Or I get to go to...

X conference, but I really want to go to Davos or whatever. Like, and that's the goal. That's great. But I think when most people really sit down and say, what would I do with more success and more money? Oftentimes the answer is, is not that compelling that there's just not that much more out there. So how do they get from that realization? The life visioning exercise you reference is one tool that,

But what other sort of tools in the toolbox are there? Because you mentioned therapy, obviously recommended if folks are inclined that way.

What other sort of exercises have you gone through or do you recommend in the book? Sure. So there's another good one, which is called The Wheel of Life, which I think a lot of people in your audience would have seen. It's like an old YPOEO thing. And I'm an old man now, so I hold up pictures of printed pages to cameras. But that's The Wheel of Life. If you're not watching, maybe we can just describe their three impact.

Yeah, we've got a wheel. There's about a dozen kind of factors and we're going to rate them. And so the factors, I won't go through all of them, but so there's definitely our finances, our career there.

There's our family. There's our fun. But then there's things like our spiritual life, our emotional life, our intellectual life. And I find when people go through that exercise, what you're trying to do is you're trying to take a holistic view of your entire life, like all the things that make you like a human being, like not just like a business person. And what I usually find is entrepreneurs are...

always like eight out of 10 in their career if they're at this level of success right like they're like they're already really successful um they're generally also doing pretty well for their kids right like most entrepreneurs i know are not actually you know on the road in cleveland like five nights a week like most of us who are you know who are parents say like okay my career is going to be first but my kids are going to be like 1.1 priority or whatever um

But then it falls off really quickly after that, right? So a lot of people sacrifice their health. Almost everyone at this point sacrifices things like their spirituality, their creativity, like their intellectual life, like their learning life. And so I think when people see that...

then there's a real decision to make, right? Where, you know, if you're living a life that's out of balance, you have to give certain things up and reprioritize to get back into balance. Now, to your point, like the next question you could reasonably ask is like, what if you don't want balance? And that's like totally okay. And some people I think will kind of be spiky in that way. Like, I think there's probably a lot of monks who are 10 out of 10 in spirituality and one out of 10 in their finances. And that's okay too. But for those of us who have more flexibility, I find like,

kind of adjusting for some of those, that spikiness can be helpful. What about people who say, yeah, but John, I want generational wealth. I don't want to be rich. I want my, I want generate, you've heard this multi-generational wealth. It's like this buzzword that people aspire for multi-generational wealth. And so sure, I've got enough to live happily for the, you know, but I want

What would you say to someone who aspires for generational wealth? So it's a big topic. And I might write a second book about this. It's such a big and popular topic. And here's what I've observed talking to people about this. What I've observed is 99.9% of humanity is trying to get more and more for their families and themselves, of course, and their kids, right?

Then there's a switch that flips when you get to a certain amount of prosperity where you start to say, am I going to give my kids too much? Am I going to ruin my kids by leaving them too much money? That's the problem, right? So if you have $100 million in the bank, which I don't, but for people that do, the problem is not, am I leaving too little? It's, am I leaving too much? And so...

The space in between there where people are like, oh, I'm going to hand down to my kids exactly the right amount of money is like, I've never met anyone who's ever said that in my entire life. It's always, oh, we need to leave them more or we need to leave them less. So I think first of all, most of the people that I've ever heard talking about trying to get generational wealth don't have it. And most of the people that have generational wealth that I talk to are trying to figure out how to manage it so their kids don't get ruined by having all this money.

Let me stop there. This is a very fruitful conversation. That's been my observation. Yeah. Yeah. Well, I think that's interesting. But why stop there? What other – like what are you holding back on? It sounds like you're biting your tongue thinking you might say something but not. Keep going. No, no. I'm happy to talk more about it. So for the people that really have – what you might consider generational wealth, right? So where they definitely have enough, their kids definitely have enough. A couple of things happen. So –

Number one is you start getting to spending a bunch of time working on your estates and your trusts and your and like the structure. And when you do that, you start to figure out that you have to put in place or you are encouraged to put in place all these like constraints on your money, like from beyond the grave. Right. Because like if you knock off, you want to make sure that your 19 year old kid doesn't inherit 100 million dollars and like go waste it on.

crack and yachts and whatever. That's a big problem, right? So you have to spend a lot of time working on that problem. You also start to hear

uh, over and over this three generations, uh, rule, which seems to be pretty prevalent where the first generation makes the money. The second generation kind of like is does like, it doesn't totally waste it, but doesn't make any more. And then by the third generation, it's all gone and like, like pissed away and, you know, uh, drugs and, and fancy cars and all that stuff. Um, so, uh,

You then, as the first generation, are now having to spend a lot of time thinking about those issues. And when you think about what those issues, how do you actually solve those issues? Like there's no amount of like lawyers and trusts that can put enough structure on that problem to solve it. What's left is trying to raise your kids in such a way that they're able to receive that inheritance and not totally waste it.

And then the question is like, okay, so what are we actually, what is the actual goal now? Is the goal to have all this money and then to retroactively have to like raise our kids to not waste it? Or is the goal really just to have great kids, right? Who we're going to raise in like a responsible way, um,

And that to me is like kind of like where I would end up, right? Like, you know, my kids will have some kind of inheritance someday, probably. I want them to make the most of it. But the way that I do that is by bringing up really good kids, showing them the right examples, teaching them the tools to manage money, as opposed to thinking I'm going to earn so much money that I'm going to get ahead of this for, you know, for a hundred generations, right? Like the number of

many multi-generational families is like pretty small in my experience. Yeah, it's the old Warren Buffett's famous for the line, you know, I'm going to give my kids enough so they can do anything, but not enough so they can do nothing. That sort of adage. I mean, you're a young guy. You've had a successful exit. It doesn't take a rocket scientist to put compound interest in place and know that when you're 80, you'll have a lot of money. You live a relatively frugal lifestyle from what I can tell. What...

are you thinking of doing with your estate when it's time to kick off? It's such a good question. And the actual answer is I barely remember. So I put that stuff in place two years ago. We had all sorts of lawyers and blah, blah, blah, and thought really hard and long about it at that point. And so there's a bunch of stuff. I mean, somewhere there's a binder with 1,000 pages of legal documents in it. And

I forget what's in it, right? I knew at the time, spent a lot of time worrying about it. Not really sure. There's some trust. There are some controls as to kind of who gets the money and when, I think. But ultimately, it just doesn't matter that much to me. To be honest with you, like, number one, I'll be dead.

So the amount of concern that I can plausibly have about it is going to be pretty low. Number two, I think, you know, again, like you can put all this structure in place and do all these things with it, but ultimately like,

your kids are going to get this money somehow and they're either going to manage it well or not going to manage it well. And that comes down to like, are they good kids? Did you raise them? Well, good adults by that point. Did you raise them with the right values? Did you introduce them to the right people and show them the right examples? That's what that stuff comes down to much more than like,

And I've seen people who have like, okay, well, there's $50,000 for a wedding and $50,000 for your first car and $150,000 for your down payment on your house or whatever. And just to me, it's like, no, I don't need to be managing my kids from beyond the grave for three generations. I have no interest in that. You know, it's funny. James Ashford was one of the first people we interviewed for this series about life after an exit. And he described...

The tension he felt with his wife, his spouse, after selling...

their business. And I remember the story. He said, you know, when you're, you know, up and comer and you're pouring all your money back into your business and you don't have any real money to speak of, in some ways it's easier because if your kids are going to go to a school, they're going to go to the local school. You're not going to ship them off to some private school. And so your world of decisions you need to make as a couple is very small.

Because you're doing things that you can afford and it's a relatively limited band. When you have a liquidity event, all of a sudden there's a lot of money and a lot of friction can occur between a couple because suddenly unearthed, unspoken about values around money are immediately revealed because you have the money to make decisions and to

All of a sudden you learn that you don't share the same values around money that your spouse does. You're nodding. What, what experience did you have around that? So I want to, your points are really good when I want to broaden it. Sure. So in my own life and in the research that, that I did, um, the time after an exit can be really hard on marriages because it's a time of transition. So it was hard on my marriage. And then as I interviewed more and more people, um,

Most of them said the same thing. And that was a real surprise because you would think like, you know, exactly as you would outline, you know, you, you know, you're an up and comer, like you're working really hard, like trying to, you know, make your family work. And then finally you have this event, which you think is going to like fix all your problems. And then it turns out that a couple of things happen with, with marriages. Number one, like,

the person that sold the business is going to be around a lot more, right? Like, and you know, and this is the modern world, right? Both spouses work in many or most marriages. So it's not like there's like one spouse like hanging out at home, but like,

Now you're just around a lot, right? In a way that you weren't before. There's also a lot of tension that happens when you're building a business because a lot of the family energy, in my experience, ends up having to go to the entrepreneur, right? And we see that you see a lot of entrepreneur families where, you know,

there's one entrepreneur who's building this huge business. There's another entrepreneur who kind of has like a normal job, right? And all the energy gets sucked up into the business, right? And the other half of the couple who's a teacher or a nurse or a mechanic or whatever, like they might be, like doesn't get as much bandwidth. And that comes home to roost after the exit in a lot of cases. Right.

I think that just all that tension and now as a place to escape, whereas previously like it didn't,

And what I mean by that is, you know, both spouses have time to kind of slow down and think like, wait a second, how is this really going? Like, we don't need to go 100 miles an hour right now. We can step back and think about this relationship, et cetera. And then some of the issues that you had raised also come up, right? Like we have now, we have to figure out like our trust in the states issue. We have to figure out like, you know, we no longer have to live in

Akron or wherever, like, cause your business is there. We can live wherever we want in the whole world. Where do we want to live? And to your point, exactly. Like there can be some disagreements there as well. Yeah. Are you really sure any that you went through personally? Yeah, I'll share one, which I think is actually a, it's actually a less serious one. Cause I don't want to, I don't want to get in trouble with my wife, listen to this later. So the serious one is like, we had to figure out where to live. And yeah,

We really did like at a certain point have the entire world to choose from. Right. So we live here in the Chicago suburbs. We've lived in Chicago since we left college and my wife's family's from Michigan. So they're nearby, but we went and like, looked up like living in Portugal. We thought about living in France. We thought about, you know, where can you live? Like living like San Diego, like somewhere that's just like, like this, but warmer and ended up like making no changes. But that's like,

That's a thing that can be, uh, that, that people can butt heads if they have different, different values about it. And where were you on that continuum? Did you want to leave? I was, I was, I was, I think more okay leaving. Um, I am, well, I think I was more okay leaving, but then as we started to see more places, um,

I started to feel like every place has its problems, which is like obviously true. But like, you know, you go somewhere like, oh, like, you know, we live in San Diego. The weather is great. Like San Diego has problems, right? I just like Chicago and Chicago suburbs has problems. And ultimately where I landed up or I ended up was wherever I am, like there's that old line, like wherever you go, there you are. Like, that's really how I feel about it. Like there's happy people and miserable people in every place on earth. Do you ever feel empty? No.

Why do you ask? Because I think for a lot of entrepreneurs, their business gives them a tremendous amount of satisfaction, a tremendous amount of intellectual challenge, a tremendous amount of accomplishment. And I just wondered for you, you've described this idyllic life where you're home with the kids at Halloween and you've got a great spouse and you're living in Chicago and everything's sort of

great. And I'm just curious if you ever miss it. Like, do you ever miss that sense of fulfillment from achieving something from, did you sort of ask? Yeah. Yeah. Yes. I feel like I'm achieving things now. They're just different. So I think that

Writing is is fulfilling to me. That's very different. Like that feels very different because no one says that you're doing a good job or a bad job and you're not busy. Like no one calls and like needs you for anything if you're just writing. So I think that's like a very personal thing is like what like what brings someone meeting in their life. I think that we get to kind of choose that.

in many ways. And there's definitely days where I personally would miss running a business. One of the things that... This is the way I feel. And as I asked other people about it, almost every entrepreneur I've talked to feels this way. The time of the business that you miss is like the zero to one period, where it's like maybe it's you and your co-founder, and then three other people, and you work in some crappy office or in your garage or whatever, prototypically your garage.

That's the time that people tend to miss. That's the time I miss. Like when I had like lots of people and like all sorts of like HR problems and customer problems, whatever, like I don't miss that. And so if that's the kind of thing that you like, which is what I like, I think that there are ways that you can be thoughtful about engineering that into your life, right? Like, so abstract from that a little bit, like let's say I liked the first three years of running my business. So I like working on a small team, which I hand select,

where, you know, I get to pick the things to work on. I mean, the customers do too, but like, you know, I get to like choose those things as opposed to putting out fires and having to go to like conferences that I hate and whatever. I can back solve for that, right? I can back solve for that in,

starting my own small business, which is kind of part of what I had done as I described. I can back solve for that and being part of like community efforts to do certain things. So I think there's a lot of ways once you figure out what are the qualities of activity that you like to do, you figure out how to do those things in different ways or you can do them the same way. And that's totally fine too.

You interviewed 70 entrepreneurs who had sold their business in a range of exits from huge to less meaningful. What stories that we haven't spoken about so far

are most memorable for you? I'll tell you my two favorites from the book. The first was, I'm going to be weird and hold up my knife again. First was my friend, the knife guy, right? Because my friend, the knife guy figured out how do you turn a thing that you were incredibly passionate about into your day-to-day life in a way that ticks all those boxes, right? So he did a great job at that.

My other favorite story, it's the very end of my, of my, my book. I was so happy to put it there. So I, when I, it always comes back to me, of course, when I was 22, 23 or coming right out of school, I got a job working for this guy named Russ and he had, he had like an X, how to describe it. It's like a, like an expert witness placement.

business. And he'd had it for a long time at that point. And I was 23 and maybe he was 33, right? He was still a pretty young guy. So I worked for him for a really short time before I went into consulting. He was really the first successful entrepreneur that I knew until I found out that one of my friend's dads in high school owned like a third of the real estate in our town. But I didn't know that at the time. So anyway, he's the first entrepreneur that I thought I knew that was really successful. And

And he sold his business. And then Wynn did like all this other stuff. Like he started like a line of like luxury pens. And he had this like project to like heal the Israeli-Palestinian conflict through entrepreneurship and like all this stuff, like all this like really cool, interesting stuff. And then one day he gets the opportunity to go buy his old business back, right? So this is a guy who built this business for like 20 years, sold it.

comes back to the same business. And at the end of our interview, I asked him, you know, Russ, you know, you, you know, you're a successful person. You have resources, like you could be doing anything you want in the entire world. And you're running the same business that you ran before. And you know, what's, you know, what's on the other side, right? Like you've gone through the whole process. Like, like what else, what else could you be doing? Like, do you want to do anything else? And he said, like, what?

And I love that. Like, I just love that answer because like, here's a guy who's like seen everything. Like he's like, he, like, he knows what it's like to leave a business. Like can do hobbies, travel around the world, whatever. And what he wants to do is run his business that he was running when he was, you know, 22 years old, 23 years old. Do you feel the same way? Like if you could rewind the clock, would you go back to running the test prep business? No.

No, I, you know, I could, I would run a, it's possible that I would run a different business, but as the business got more complex, I enjoyed it less. And I think that's, that's relatively common. You know, it's nice to see like bigger numbers and like bigger growth and whatever, but like my favorite times of running that business were the early days. And I can go, I can go engineer that, you know, as, as we'd already said in my own life.

It's interesting. I'm reading Simon Sinek's book, The Infinite Game. Have you read it? No, I read his other book. I don't think I read that one. Yeah, yeah. It's actually a really interesting concept. Simon Sinek, of course, the guy who wrote Start With Why. The Infinite Game is this idea of, you know, there are finite games where there's a winner and a loser.

There's an objective goal that you reach the goal and then you decide you've won. And so it could be a financial, like I want X million dollars of net worth or whatever, would be a finite game. In his mind, an infinite game is one that just goes on forever. You never win or lose. You're always optimizing and trying to aspire to this kind of idyllic land on a hill that you never actually get to. And I wonder...

It's almost the antithesis of building to sell and selling a business so that you can have the kind of life you describe. And I'm just trying to reconcile that.

You know, this idea of the infinite game and building a business so that it becomes like your life's mission to build this business. Sounds a little bit like Russ, where he's just happy to build this, you know, expert witness placement business. And when he sold it, he wanted to get back into it. And I think some of our listeners may be asking themselves, like, do I want to play the infinite game?

and build this business and as Bo Burlingham says, go out boots first? Or do I want to live the life of John Rood, which is one where he sold his company and he's now flexing other muscles? Is there a way you can help guide people through that decision in their mind?

Yeah, here's another tool that I like to use. And so sometimes people call it the vivid vision. Sometimes people call it the painted picture. And it was the 1-800-GOD-JUNK guys were big on this one. And I think one of them wrote a book on it. Cameron Harold was the guy's name, wrote a book on it. Yeah. And it's a great exercise where you sit down and you're writing about

"X number of years in the future, here's what my life is like." And there's no bullet points, there's no numbers, there is text, right? So you're writing about, "Here's what my day looks like." And you're writing it longhand. You're like, "I get up at this time and here's what I'm gonna have for breakfast. And here's how I feel. And after breakfast, I do this."

And so you're thinking about what, like in the course of your day is actually really makes you happy is what is fulfilling. Right. And so not, not these like lofty long-term 20 year goals. Right. What we have is now, right. Like our, not too philosophical, but like our fundamental unit of human experience is now, right.

when we think about the future, we have anxiety about the future. When we think about the past, we have regret about the past. All we experience is now and today. So if you think about what do you want today to be exactly like, then we backfill that with like, what are the activities that get us there? Right. And so for me, um,

I've done that. And like, this is kind of the life where I'd envisioned where, you know, I'm doing, I'm on with you. I'm enjoying our time together. You know, I did some stuff for my, my AI business before with my partner who I, who I love, like one of my, one of my best friends. You know, I'm going to see my kids later, you know, we're going to have a nice evening together, et cetera. And this is what I want. But, you know, if you did that kind of exercise and you're, it's like,

I wake up at 5 a.m. because I have to get to CrossFit before the day begins at Davos or whatever. Then you build a different life around that, right? But it's really hard. It's easy to say like, okay, in 10 years, I need to have $10 million, right? That's kind of like too easy. I think it's harder and more impactful to say,

in 10 years, like here's what the quality of my lived experience is going to be like, here's like based on my values and how I know myself, like here's what makes me happy. That I think is a really good exercise to go through. And how do you stop and break the inertia? Because there's an enormous amount of inertia that, that I think

founders feel like pushing them forward. So, you know, there's a business that needs their, you know, demands their attention. There's customers that need their attention. There, you know, there's goals to achieve, there's et cetera. And society is constantly in your ear, you

saying to want more, right? You got to have more followers on Twitter. You got to have more longer yacht if you're Larry Ellison or whatever, right? It feels like it's not natural what you're doing. Your ability to write the vivid vision and write it longhand and live in and make decisions and sacrifices to live it. Like that takes a lot of energy to break that inertia, doesn't it?

Yeah, I think that it does. That's why for anyone, I recommend this to people all the time and I do a little bit of coaching. I always recommend this to my coaching clients where if you're getting to the point where you might sell your business in the next like three to five years, like it's even like a possibility to start doing these kinds of exercises that I've been describing now as opposed to once you're in that process or once you are through that process for a couple of reasons. So number one is you can start to think about

how urgently do I want to get out of the business that I'm in? Right. And for some people, some people are miserable running their business. Right. And there's constant firefighting and all these HR problems and blah, blah, blah. They just like want to get out. They're doing it for the money. They want to get the money. Great.

Plenty of other people that are having a great time running their business, right? There's a guy named, do you know AJ Wasserstein from Yale wrote these amazing papers on post-exit life? - No, I've heard the name, but we should have him on. - You should absolutely, he's an incredible guy with incredible story. His papers are great. He's in my book sharing his story. And he said this thing I'll never forget. He says, "If you wanted to run a business so much, why did you sell the first one that you had?"

And so that's why when you think, okay, right now, if you're a person who's in the world of running your business, you're trying to maximize its value, whatever, sit down. Take a three-day weekend by yourself in a cabin and really sit down and think about where do I want to be in five years? And the answer might be like, I want to be running the same business, but I want...

Steve, my CMO out. I don't want to see Steve again. Right. And then you kind of know what you what you have to do for a lot of people will be different. And then I think you can kind of back solve from from where you want to be to what the steps are today.

I could talk to you for hours, but I know your time is precious. So let's point people to the book. It's called Beyond the Exit. Get it on Amazon and everywhere. Yeah, on Amazon. John's got it up on the screen, which is great. So folks can learn more there.

If people wanted to reach out on social media, is there a good channel for them to do that? Yeah, sure. So I'm on LinkedIn. I'm on Twitter. You can just search for me. John Rood is R-O-O-D. There's not too many of us. So you find me there. And I love to hear from readers. I love to talk to entrepreneurs. So I encourage everyone to reach out. I love to have these conversations for sure. And we'll put John's coordinates in the show notes at BuiltToSell.com. John, thanks for doing this. John, thank you. Always a pleasure. We'll see you.

And there you have it for today's episode between John and John Root. If you enjoyed today's podcast, be sure to hit that subscribe button wherever you're listening to today's show. And if you want to help support this podcast, I'd encourage you to comment or leave a rating and review. Just as a reminder, you can head over to our YouTube channel and watch this full video interview at

at BuiltToSell. For show notes, including links to everything referenced in today's podcast with John Rood, you can visit this episode page over at BuiltToSell.com. There you're going to find links to everything referenced in today's podcast. Special thanks to Dennis Labataglia for handling today's audio engineering. And thank you to our community of certified value builders who help us bring our message to you. Our advisors are experts in helping you build the value of your company. To get in touch with an advisor or learn how to become one yourself, visit

head over to valuebuilder.com. I'm Colin Morgan, and I look forward to talking again next week.