Jerome Myers is a Certified Exit Planning Advisor, the founder of Exit to Excellence, and probably the only person in the space who introduces himself as "the product of bad exits." He built a $20 million division from zero in one year, watched half his team get cut, walked away, and then spent years trying to understand what happened to him psychologically.
He now helps founders navigate what he calls the Founder's Exit Paradox, winning on paper and falling apart in person.
This was a different episode for us. We didn't talk about deal structure or portfolio construction. We talked about what happens to people after the check clears.
Here are the parts worth your time.
The $2B founder who still couldn't answer the question
Jerome was standing in a conference room in Carlsbad, California when a founder who had exited for $2 billion started describing the exact same feelings Jerome had been carrying. Loss of meaning. Loss of relationships. An existential crisis he couldn't name until that moment.
When Jerome asked him how he got out of it, the guy said he'd let him know when he did.
That was the moment Jerome realized nobody was solving this problem. The only resource he could find was a Harvard Business Review article that basically said: congratulations on selling your business, now prepare to be depressed. He decided that couldn't be the reward for 15 to 50 years of building.
Why $15M in cash feels worse than $3M a year
This one stuck with me. Say you're making $3 million a year running your company. You sell for $20 million. After taxes you take home maybe $15 million. On paper, you should feel rich.
But Jerome says most founders feel the opposite. You went from a stream of deposits hitting your account to nothing. You only see the balance go down. And the question that plays on repeat is: how long before I run out?
He calls this the “Transaction Illusion”, the belief that the money is going to make you happy, fulfilled, and free. But money only solves the first two levels of Maslow's hierarchy. Shelter and safety. It doesn't touch love, belonging, purpose, or impact. When the exit doesn't deliver those things, and it never does on its own, the gap between expectation and reality is where depression lives.
60% of your life vanishes overnight
Jerome runs workshops where he has founders list the five people they spend the most time with. Three out of five are almost always people they work with.
Now imagine exiting. Sixty percent of the people you spent your days with are gone. And most of them were what Jerome calls "dear friends", or the people you're close to because of proximity, not because of a deep relationship. Men especially make friends this way. You work next to someone for years, you consider them a friend. But when the proximity ends, the friendship ends too. A lot of founders don't find that out until it's too late.
The Five Scars of Success
Jerome has identified five experiences that shape how founders behave after a liquidity event. The one with the most impact is total financial ruin: not growing up poor, but having lost everything as an adult.
He told me about a client who exited for $44 million. The guy went through bankruptcy earlier in his career. Private credit from personal connections was the only reason he was able to rebuild. After the exit, Jerome couldn't even get him to book a trip to Destin, Florida. He was driving a 15-year-old car. Jerome eventually got him to buy an $80,000 Lexus, and the guy's first reaction was "what are people going to think about me?"
The approach was small steps. Not trying to change the mindset overnight, but showing through small experiments that things won't fall apart if you spend a little. Jerome sends clients like this the book Die with Zero, and he says it's had real impact on how they think about delayed gratification turning into something that actually works against them.
What fulfilled founders actually spend on
I asked Jerome what he's seen people spend money on post-exit that actually made their lives better. The answer wasn't material stuff. It was experiences with people they care about.
He told me about a scholarship he funds at his alma mater. One of the recipients was about to drop out because her parents couldn't afford tuition. She finished her engineering degree debt-free, stayed for a master's, and texted Jerome on Mother's Day to thank him. He said that text meant more to him than any car he could have bought, and he's a car guy. His dream purchase was a Nissan GT-R because his dad's first car was a Nissan Maxima.
The research backs this up. Jerome referenced a longitudinal study that found doing things with people you enjoy is the single strongest driver of life satisfaction. Not doing things alone. Not buying things. Experiences, with the right people.
The purpose formula founders already know
This is the part I want every founder listening to sit with. Jerome says the question you need to answer is simple: who are your people, and what problem do you solve for them?
If you can answer that with clarity and specificity, you're on the right track. If you can't, everything sounds like a good idea, you become a target for other people's agendas, and you end up a supporting character in somebody else's story instead of the main character in your own.
The irony is that founders already know how to do this. It's exactly how you build a business. Who's the customer? What's the problem? How do you solve it? They've done it professionally for decades. They just forget to apply it to themselves.
Give the full episode a listen. Jerome is one of the most thoughtful people I've talked to about what happens on the other side of a big exit, and this conversation goes places we don't usually go on the show.
— Sam Silverman
Silverman Capital
