1652: Founder Exit Strategy & Life After Liquidity with Jerome Myers

Robert Plank 0:00 Jerome Myers is the founder of Exit to Excellence, and he is the creator of the Founders Exit Paradox and Founder Observatory. And his work draws on more than 3500 founder conversations, over 400 podcast interviews, and over $2.5 billion in exit value represented, and he is the author of three books, and has dedicated his work to understanding a question the exit industry rarely asks, which is what happens to the founder when the business they built no longer needs them. And it's all in his newest audio book, narrated by me. That's how he met. It's called The Exit Expedition, and it takes founders beyond preparing their companies for an exit and into that much harder terrain of preparing themselves for what comes next. So, Mr. Jerome Myers, good to see you. How are you?

Jerome Myers 0:53 Robert? Good to be with you, man. So cool to put a face with the name. You know, all of our conversations were over LinkedIn up until this point, and so be able to hang out with you live is an honor, man. Thank you so much for having me on the show.

Robert Plank 1:07 Thank you for thanking me, and yeah, like I think our generation, we've had sometimes you meet that friend on the internet back when the internet was primitive, and there wasn't always visual images, video, and then sometimes you meet that person in real life, and it's like, whoa! It's kind of like I know you, but I don't know you, and it's a weird quasi déjà vu. And and so, yeah, I'm excited to chat with you about the the book and the podcast. And so, what are you all about? What do you think makes you unique?

Jerome Myers 1:34 Yeah, we're on a mission to end founder suffering. We watch so many people spend 15 to 50 years building something that one day they're going to exit, and we watch so many of them descend into the founders' exit paradox. Whether they got the money and now they have time and treasure and talent, and they don't know what to do with it, or they close a business that they fought really hard to keep alive, and they just couldn't overcome whatever the reasons were that they were going to close it or they give it away and some people get really excited about that. The only problem though is most of the time they didn't save much money for retirement and so then they become a burden to the person that they gave the gift to. And so our goal is to help people exit well. Unfortunately, 75% of people who exit regret it, and it's our goal to cut that number down day by day, minute by minute, hour by hour, in order to make sure that more founders get the reward that we believe they deserve for all the work that they've done.

Robert Plank 2:38 Well, that is a crazy, scary statistic that there's that regretting of it, and the the image you lay out, it feels like just falling off a cliff, right? Where, like you say, you fight to keep this business alive. It becomes a huge part of your personality, years, maybe decades of your life. It's your mission, it's your purpose, just your identity. And then to get rid of that for whatever reason. It just seems like a really scary undertaking, and a lot of you know bad things happening afterwards. And so, what's this typical situation like? The the founders that you serve and you help and you know, like you know, what's what's going through their head? What goes wrong?

Jerome Myers 3:16 Yeah, so I think the first thing that sets them up for failure is the belief that having a liquidity event is the finish line. I watch many people believe that everything gets better if they have enough money, and the fact of the matter is that's just not true. The money just amplifies what's going on in their lives, and so we can say we're busy running our company. We can say we're doing this or doing that, and in all of those things, we aren't actually taking care of the most important things. And so, if you happen to get to a liquidity event, which is more rare than playing professional sports, you end up in this space where you can't avoid it, you can't hide from it anymore, and you have to deal with it. The issue, though, is on the backside of a liquidity event. You don't have any of the things that organized your life. If you're a business owner today and you were in a meeting this morning, it was because the business told you so. If you look at your bank account, it's because the business put the money there. If you look at who you're going to spend time with? It's because the business put it there, and if you think about the problems that you're solving, it's because the business put them there. And I think too often people believe that entrepreneurship is this thing of freedom, and you know your own your own boss, and you do whatever you want. But the reality is, the business is dictating, is organizing your life, and it's not a bad thing. It's just something that we have to come to understand is true, so that once we accept that truth, we can make the adjustments and interact and engage with the business as we see fit. I was doing a presentation. I had about four hours with a group in Edmonton. And one of the things that I uncovered when I was with that group was this fact that most owners are the catch-all. So whatever the problem is, if it doesn't fit in one of the employees' job description, it is my problem, and I must go solve it. And what we think is ideal is that the problems are being solved, and that the founder, the owner, they get to pick and choose which problems they work on, and so flipping that dynamic, I think, is extremely important.

Robert Plank 5:32 Yeah, the way you describe it, the business almost feels like its own alive person.

Jerome Myers 5:38 Well, so you know whether it's a person or not, we don't get into those details. But every owner has a relationship with the business, and that relationship changes. And when the relationship changes enough, some people believe that they should exit it. They should end the relationship in some way, shape, or form. And that is where I think we can help people a lot because an exit, especially a liquidity event, isn't the only option. And so, as people are going through this continuum, I've got a good friend named Tina. She runs a company called Liberated Leaders, and they came up with this business maturity diagnostic, and it allows you to see if your business is actually acting its age. And that, for me, is probably one of the biggest epiphanies in my thinking in 2026. It's like, you know, people talk about the business being their baby, but if you've been running a business for 20 years and it's still a baby, you're probably not interacting or engaging with the business in the proper way so that it can grow up and go off and be independent, which is what is the ideal situation for somebody who wants to exit their company. But if it's a baby, nobody really wants to get up in the middle of the night and feed a baby. Nobody really wants to change diapers. Like those things are onerous, and we do them because we love babies. But I don't know any person that wants broken sleep and to be woken up from the screams of a child who's hungry or wet.

Robert Plank 7:09 Yeah, I like that analogy, and like it's okay taking care of a baby for a while temporarily, but you don't want it to be that way in perpetuity, and so that's a fun analogy of you want it to grow up, and when when I talk to guys like you who are on this topic of exiting, it just seems like a massive undertaking, right? It seems like something that takes like many years on end, and it like blows my mind of how much planning is needed and how like complex and careful you have to be. And so, what do you wish more people knew about this whole process?

Jerome Myers 7:46 Yeah. So we've already talked about the transaction not being a finish line. You know, in the book you narrated for us, we talk about the frame of exits or business ownerships being an ascent, a summit, and then a descent, so a mountain expedition. And what I wish more people knew is that the most dangerous part isn't getting up the mountain or even hitting the summit. It is the descention. It is coming back down the mountain. I had a friend who just finished climbing Mount Kilimanjaro in Tanzania, and after a few days, I was like, "Are you alive? Because he didn't send me any pictures, and I asked him to send me pictures whenever he could. And so, no. And then, of course, he sent some pictures on the backside of it. But the most dangerous part of that expedition is the descent. And so, we talked a little bit already about how you don't realize how much the business is organizing for your life, or you don't want to give the business credit for what is organizing in your life. But when you pull that out, and now you're trying to make decisions with the most resources you've ever had, it makes everything look like a great opportunity because you don't have anything to filter it through. You you can't say I don't have time for that because your calendar is empty. You can't say well I can't afford to invest in that because you've got the cash to actually invest in it and the opportunities, the board opportunities, the new company ideas, you don't have a limit on where you can apply your talent, and so we encourage people to figure out what they want to do while they still have the business to organize things, such that when they get to the place where they don't have something that's anchoring them, they have this new filter, this new approach to life that they came through when things were steady and familiar.

Robert Plank 9:48 Oh, interesting. Well, getting the structure back, and it reminds me of all the stories you hear about people that win the lottery, right? When people kind of have a lot of money coming in for whatever reason, and they don't have a plan. They end up broke. They end up dead. They end up all their relationships ruined. Versus, if you're trying to kind of think for into the future a little bit and say, "Hey, well, I can't plan for everything, but I know that there will be some, you know, more money, more problems coming my way. Then you hope that you can kind of like mitigate the risks, or at least kind of make whatever catastrophes are in your future not not as as life or situation ending as they might be if you had no plan.

Jerome Myers 10:31 Yeah, I think you got to have a plan without question. You know, again, you're going to have more money, time, talent, and treasure than you've ever had, and so if you don't plan for that, then you are going to have tremendous issues. I interviewed a guy named Alan; Alan Crockett a few weeks ago on my podcast, and he's a rancher, and so we were talking about fields, and it was like you know, till fill is going to grow something. It's just a matter of whether it grows weeds or flowers, and it's a function of what's planted there. And so, what we have for people on the backside of their exit is a tilled fill, and it's a matter of do you just want it to be happenstance, or do you actually want it planned? And you know, you you don't end up with a beautiful garden by accident. Each plant was selected, it was placed, and then they were pruned. And you know, I was hanging out in the botanical garden this morning in my town, and you know, the rose garden is a beautiful. You got all these flowers, and you know, it's getting towards it in the summer here, and a lot of that stuff's going to go away. But you could see the intentionality placed in each plant, and you know, somebody took great time to make those selections and then do what was necessary in order to help them stay healthy throughout the summer. Because you know, we were actually having a drought, and so they had to water the flowers in order for them to stay alive.

Robert Plank 12:06 Yeah, so it makes a lot more sense to be intentional instead of just letting random chance happen to you. And the the subtext of what you're saying too is to allow the time to think things things through and make sure that you're doing the right thing and accounting for the unexpected problems, like well, I have to kind of you know do more manual watering, things like that. And so your book, it's a parable book, I think they call it, right? Where it's like, well, there's there's lessons in there, and you know, as you can imagine, I've narrated all kinds of books, and some of the ones that talk about exiting a business are really dry, right? They talk about EBITDA and GAAP and all these terms, and it's kind of it's okay for a while, but it's devoid of the personality and the story. And what's great about this kind of blend of fiction and nonfiction is like it gives you time to think through the ideas and sometimes draw your own conclusions, right? Because you're like hearing this fictitious story, and then you kind of you make your own connections, and it feels closer to lived experience. And but I'm curious about this approach to it. Like, why did you make it a parable book, and what was that like to like figure out how to write it this way?

Jerome Myers 13:20 Yeah, well, the Bible is a parable, and it's the most read book and best-selling book in the world. I think the other piece of it is I read some Patrick Lecioni books in business books, Five Dysfunctions of a Team, and a few others, and I just thought it was brilliant how he was able to convey the message and the lessons through a parable. Now, you know, sometimes you can get lost in the sauce. It's overdone, and we were a little concerned about that. But you know, when you get to a book that's 300 pages, you got to have something to carry it through. And from my perspective, the parable made it human. You know, we we could have made it a research paper and something that psychologists would read, but that's probably boring. We wanted something that was going to grab the interest of a founder, let them see themselves in the main character James, and then go on the journey with him as he was figuring out how to get up the mountain and get back home. Because at the end of the day, if we can't get the founder back home safely, we as exit advisors have felt them.

Robert Plank 14:35 Wonderful, and it's it's such a cool metaphor. I keep going back to that, you put all the attention on the climbing of the mountain, but then there's that kind of forgotten piece of well, getting back down safely and getting back home. If you don't have that very important part, then the whole mission was a failure. And what's also great about the writing process is you always discover something about yourself, right? I think that's universal to like any human when you write things down, and the the decisions you make when you go from whatever whatever book you imagine in your head versus what is written down, it's drastically different. And on the way, you kind of come across some own your own your own personal aha. So I'm curious about in the process of writing this book, like was there anything that you discovered about yourself that maybe surprised you?

Jerome Myers 15:26 I will tell you what I discovered about the exit process. So the whole reason why the book became a book, because it started as a white paper, was because of our understanding of the transaction illusion. I didn't get it before. Like business as a marathon was a thing. I didn't question it. I didn't question the thoughts around that when you get the liquidity event that there was an end, and like the fact that there was so little done on the backside of it was like, oh well of course there's nothing really done on the backside of a marathon like you drink beer and you eat carbs and you try to replenish yourself but nobody talks about the blisters nobody talks about the sore legs they don't talk about that part they just talk about their metal they show their metal but I didn't connect the dots the mountain is a much better metaphor from my perspective, and the whole reason why the book came out was because of the transaction illusion. And now that you've asked me this question, because nobody's ever asked me that question as it relates to any of the books, what I learned was that about myself is that being a thought leader is core identity for me. I want to be on the leading edge of the concepts and frameworks, and even best practices for the exit planning industry. And so, this book to me, reframes it in a way where we can actually move the needle on the 75% of regret, and being there in that space and offering this to the exit planning community is a point of pride, and it's why we decided that it was worth making an investment to get it on Audible when we haven't done it with any of the books before this. And you know, we've done three exit planning books, and then there's another three that aren't related to exit planning. But like this, this thought that we would go that extra step and make it available so that we can get broader reach. Is it? It furthers this concept of we want to be the ones that are on the leading edge of the most important innovations as it relates to exit planning.

Robert Plank 17:58 Very nice, ybuilding a whole ecosystem, right? You have the book, the Audible, the podcast. You're doing the speaking gigs. You're kind of pursuing all these avenues to get attention on what you're doing. And I think that's a lot of fun to hear about how the the core factors of the book take shape, right? And something as kind of foundational as the metaphor, we've all been there, where like someone has a weird metaphor that like doesn't quite fit, and then but they've been using it so long that it's kind of stuck. It's a cliche, like the whole marathon thing. So that's cool that that came to mind, and that now it's visual. Even the picture behind you, right? It's it's hard to get that out of our head once we've seen it. So you're doing a lot of things correctly, and you know, having a lot of amazing conversations and helping people, and so there's so much to this topic, and it's like such a whole world, right? Like I'm sure, like the you've talked about in your podcast, it's just like it's a whole other frame of mind, isn't it? When you hear people about they they grow a company and they sell it and they buy another one that's struggling, and they build it up, and they sell that. It's like, whoa! It's such a such a whole other world that people play a part in that sometimes we don't even know is is possible. And they just kind of you know achieve great things. And so, with everything that that you know and you've seen and you heard, you taught, you've done, do you think there might be a missing question in this conversation happening right now that I should be asking you. I just don't know to ask you.

Jerome Myers 19:29 That's a tough one, man. I think the question that's worth talking about. Is why do founders regret their exit? Because I don't think we've talked about that. I just made the stated the I stated the fact and didn't cite a source or anything else. But I think why they regret. The exit is probably worth having a conversation about.

Robert Plank 20:03 Okay, and why do they?

Jerome Myers 20:05 Most people would think it's the money, and on very rare occasions, it's that unless they underestimated what the company was worth, and then they found out that they couldn't do what they wanted to do with the proceeds from it, meaning retire. The reason why they regret it one is they don't know how to introduce themselves, and they struggle with who they are without the business. The second is they're typically lonely. What we find in our workshops is three out of the five people they spend the most time with, or 60% of the people they spend the most time with are tied to their business, and so when they leave the business, they lose 60% of their social interaction. The third thing is you get 40 to 60 hours a week back, and if you don't have a plan for that, you are bored because you don't have the challenge and you don't have something to fill that time with, and so you struggle with the freedom of not having something on your calendar. But you also struggle with the freedom of not having something to challenge or make you struggle. And then I think the last piece would be they start questioning whether or not their life matters, and so if you don't know if your life matters because the thing wasn't the thing anymore because you sold it, then you struggle quite a bit, and those things lead to what I would call dissatisfaction with life and experience, and it takes quite a bit of time for them if they don't go through a structured process to get back in the space where they truly understand who they are, who they should be spending time with, whether or not the things that they're doing with their time matter, and how to fill the time that they got as a result of clearing up their calendar.

Robert Plank 22:06 Some really big questions, especially centering around identity and this thing that we hope and think is a gain, but then you sell the business and all these things you mentioned, it's really a loss. So you need to turn the bad back into a good by kind of dissecting this problem, and as you say, go through this structured process. So, if someone is curious about this process, if they'd like your help, your advice, what they want to know about your book, websites, programs, what are some next steps here after listening to this podcast?

Jerome Myers 22:37 Oh man, I think the best thing a business owner could do, whether they're thinking about exiting or not. I assume they're thinking about exiting if they got to this part of the show, is to go to exittoexcellence.com forward slash era. That's our exit risk assessment, and it will allow them to get a complimentary report that has action items for them over the next 90 days on things that they can do to reduce risk to them having a successful exit. The fact of the matter is, exit strategy, good exit strategy is just good business strategy, and you'll enjoy your business more the better you are prepared for an exit.

Robert Plank 23:21 Very nice, and you hear a lot about that, right? That if even if you aren't planning on exiting immediately or for the foreseeable future, it's still there's value in fixing up that business, right? And making it where like you do have options, and if the right opportunity does present itself, then you're much better positioned, and you have a business that's less chaos and more fun and and just you know more reliable and and all these things that we're hoping to achieve and maybe we we wanted this when we started but then we get caught up in the day to day we kind of drift and lose track of some of these important factors and you say that quiz that diagnostic is at exit2excellence dot com for to get that personalized exit risk report, which includes highest risk areas, hidden dependencies, post-exit vulnerabilities, immediate priorities, and risk reduction recommendations. It's a diagnostic designed to show you what deserves a closer look? We've been speaking with Mr. Jerome Myers at exittoexcellence.com/era to generate that exit risk report. So that way, if you're thinking about selling, if you're approaching that point, then you can go into it with intention and some strategy and some thoughtfulness, and not just be winging it and flying by the seat of your pants. So exittoexcellence.com/era. But before I let you go, Mr. Jerome Myers, it's time for the scary part of the podcast where I try to stump you. I try to put you on the spot by asking you about a fun or interesting quote or lesson that has served you. So. What comes to mind as far as a fun or interesting quote or lesson?

Jerome Myers 25:04 I don't know how fun it is because it ends up being work on the backside, Robert. But the quote is, "Your dream should be real. I watched so many people stop dreaming as a kid, and when they stop dreaming as a kid, they assume that they have to be practical. They have to be reasonable, and they just continue to live the same year over and over and over again. And I just dare people to believe that they can live that life that they had their wildest dreams of, and if they've done everything they dreamed of as a kid, I dare them to dream something new. I'll never forget Raleisha, my lady, asking me once, "Do you even know how to dream anymore? Are you just living in everybody else's? And it really well it it was it didn't hurt, man. I'll be honest with you. What it did was pull me out of being the supporting character in everybody else's story and movie, and allowed me to find what my main character energy was, and then make sure that when I'm supporting other people, is this in support of my own? And I think when you have that, you rig success.

Robert Plank 26:32 Yes, that's inspiring. Well, let's rig our own success and tap into some of that main character energy by checking out those resources. exittoexcellence.com/era is the diagnostic assessment, and then the audiobook that we've been mentioning is called the Exit Expedition: Why the Deal is the Only Summit, and we'll have those links underneath this podcast in the show notes. And thanks for taking the time, Mr. Jerome Myers, for being an inspiring, guiding, positive force, and I'm glad we took the time to do this. I had so much fun speaking with you.

Jerome Myers 27:06 Robert. This was awesome, man. Thank you so much. I see why your show is so popular.