Deal Maker John Martinka: The Unspoken Reason Your Exit Will Crush You And The Playbook To Save It
What if your exit leaves you broke, bitter, and forgotten?
John isn’t just another M&A advisor. He’s the guy who shows up when founders realize too late that their exit strategy was built on ego, guesswork, and wishful thinking. Nicknamed “The Escape Artist,” John Martinka has spent over 25 years guiding entrepreneurs through the most emotional and high-stakes chapter of their journey getting out.
If you think building the business was the hard part, think again. What comes next is the part that most founders fail.
The Lie Entrepreneurs Believe About Exiting
Founders spend decades building a business, then expect to flip a switch and walk away rich and fulfilled. John has seen what happens when reality smashes that illusion. And the damage isn’t just financial — it’s emotional, personal, and sometimes permanent.
“They think people will line up to buy their business because it’s their baby. But there are a lot of other good businesses out there,” John warns.
The result? Missed exits. Lower valuations. Or worse, no deal at all.
Your Business Will Betray You If You Don’t Plan
One of the biggest exit myths? That size protects you.
John shared the story of a business that sold for $70 million. The founders realized, too late, they were still too essential to daily operations. That mistake can crush value even in eight-figure deals.
“They had a team, but they were still too involved. And that’s not unique. Most owners never truly detach.”
That owner dependency becomes a buyer’s nightmare. No matter how profitable the company is, if the founder is the business, there’s no enterprise value.
The Emotional Side No One Talks About
Exits aren’t spreadsheets. They’re identity shifts. For many founders, the business is who they are.
Jeffrey and John dive deep into the psychological minefield: fear of letting go, pride in the wrong places, and the myth that being needed equals being valuable.
John puts it bluntly: “Let your management team take over. Delegate. Even if they do it 70 percent as well as you, that’s still a win.”
You can’t exit what you won’t release.
Buyer Due Diligence Goes Both Ways
Most sellers think the due diligence process is one-way. It’s not. In fact, John argues that one of the biggest mistakes entrepreneurs make is failing to vet the buyer.
“You’re handing over your baby. You better know what kind of parent they’ll be.”
He tells the story of a seller who backed out of a deal because the private equity firm made them uneasy about the future of their team. The offer was strong, but the cultural fit was off.
This isn’t just about money. It’s about legacy, team, and trust.
The Myth of the Highest Offer
One of the most sobering truths in this episode: the highest bidder doesn’t always win. Founders who optimize only for price often regret it.
“I’ve seen multiple offers on the table, and the seller chooses the lowest one. Why? Because that buyer felt like the right fit,” John says.
The lesson? Culture matters. Alignment matters. Trust matters.
Because after the wire transfer clears, you still have to live with the consequences.
Rollover Equity and the Second Bite
John breaks down a common but misunderstood structure: rollover equity. In larger deals, sellers often keep 10 to 20 percent of equity in the new entity. That second bite can be even bigger than the first.
But only if you’re smart about who you roll with.
“If the buyer flips the company in five years, your 20 percent could become 80. Or it could become zero. That’s why vetting your buyer isn’t optional, it’s survival.”
Avoiding Seller’s Remorse
Not all regrets happen after a failed deal. Some happen after a successful one.
Seller’s remorse is real. John explains how it creeps in when there’s no clarity about life after the exit. Too many founders plan for the transaction, but not the transformation.
“You need a next great adventure. Without that, the money won’t save you from feeling lost.”
He urges every seller to work with a financial advisor before going to market. Know your number. Know your next move. And make sure your spouse is onboard — because your post-exit life is theirs too.
The Hidden Threats That Kill Deals
Forget market trends. The real deal-killers are often internal. John lists the hidden threats:
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Customer concentration
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Supplier dependency
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Weak or outdated financial systems
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Owner-operator structure
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Fake profitability from personal expense blending
“Too many owners treat the business like a lifestyle engine. They run personal expenses through it. They think they’re saving on taxes but they’re destroying value.”
John’s advice? Clean up your books. Separate personal and business finances. And stop treating EBITDA adjustments like a magic trick.
Why Your Lawyer Might Blow the Deal
This episode hammers home a critical, often ignored truth: your general business lawyer is the wrong person for M&A.
“You need someone who lives and breathes transactions. Otherwise, you’re going to burn time, kill trust, or both.”
John shares the story of a massive, over-engineered purchase agreement from a big-firm lawyer who had no feel for mid-market deals. The seller’s attorney didn’t even read it. They rewrote the whole thing from scratch.
If your advisor isn’t in the deal space full-time at your deal size — you’re taking a knife to a gunfight.
Legacy, Impact, and the Deeper Why
The episode ends on a powerful note. John shares his passion project: bringing tech to underserved schools in the Caribbean.
He’s donated over 10,000 laptops, set up dozens of Wi-Fi networks, and takes students on cultural exchange trips every year.
“When you give back, you benefit as much as the people you’re helping.”
This is the deeper reason exits matter. Not just for the payday. But for what you do with your freedom after.
The Bottom Line
Most entrepreneurs fail their exit. Not because of the market. Not because of valuation. But because they ignore the emotional, operational, and strategic landmines that John Martinka exposes in this episode.
If you want your exit to be a launchpad — not a breakdown — this is required listening.
Listen now and subscribe to The Deep Wealth Podcast. Your future self will thank you.
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