My $25M Exit Fell Apart—Here’s Why It Nearly Broke Me

Selling your company is supposed to be the dream, isn’t it? The grand finale. The ultimate validation of years spent grinding, sacrificing, pushing through exhaustion, and clawing your way past failure. They tell you it will be worth it—that the payoff will wash away the doubt, the struggle, the moments of despair. But no one warns you about the other side. No one tells you that an acquisition, especially one that crumbles in slow motion, can unravel you from the inside out.

In 2019, we received an offer that felt like a coronation. Twenty-five million dollars. A sum that could rewrite the course of our lives. As bootstrapped founders, we had lived through lean months, through bets that barely paid off, through the kind of stress that carves deep lines into your soul. This was supposed to be the moment when all of that turned to gold. We had made it. Or so we thought.

The Seduction of the Exit

At first, you’re weightless. Euphoria pulses through your veins. You allow yourself to dream—of ease, of security, of stepping off the relentless treadmill and breathing, really breathing, for the first time in years. It feels like a kind of redemption, proof that the struggle meant something.

But exhilaration is a fickle thing. It fades. And what it leaves behind is something darker—a creeping dependence on the outcome. A slow erosion of perspective. When you come from modest means, a number like twenty-five million isn’t just a figure on a contract. It is safety. It is status. It is a new identity. And that is where the danger begins.

We started seeing the deal not as an opportunity, but as a necessity. Every revised term sheet, every renegotiated valuation, every delay gnawed at us. Each concession felt like a small wound, a necessary sacrifice to get across the finish line. We told ourselves that walking away wasn’t an option. That this was it. That we had to see it through.

The Trap of Sunk Costs

Deals don’t fall apart overnight. They unravel, thread by agonizing thread. Ours stretched on, past the initial excitement, past the early warning signs, past the point of reason. The valuation slipped. The terms tightened. The finish line receded into the distance, always just beyond reach. And still, we pressed forward.

Why? Because the mind is a stubborn thing. Behavioral economists call it the sunk cost fallacy—the irrational belief that the more you invest in something, the harder it becomes to abandon it. We had spent months in negotiations, endured sleepless nights, wrestled with impossible decisions. To walk away felt like setting fire to everything we had endured. So we stayed.

Each new concession was rationalized as just one more hurdle, just one more compromise. But the deal was no longer a victory waiting to be claimed. It was a trap, slowly closing around us.

And then, the inevitable. The deal collapsed. Just like that, the money vanished, the future we had sketched in our minds erased. We were left with our company, with ourselves, and with a hollow, aching question:

Who were we, if not the entrepreneurs who had just sold their business?

The Reckoning

No one prepares you for the aftermath. When your self-worth becomes knotted up in an outcome, its loss is more than financial—it is existential. The confidence that had once propelled us forward now felt like recklessness. Had we been naive? Foolish? Had we failed in some unspoken way?

For weeks, we drifted. Going through the motions. Trying to summon the same fire that had driven us before. But something had changed. The business we had built—the same one we had once cherished—felt smaller, almost diminished. Could we really just return to running it as though nothing had happened?

What I Wish I Had Known

Here’s the truth: an exit isn’t a win. It is just another phase in a game that never really ends. Real success isn’t in selling—it is in building something strong enough to thrive, whether you sell or not.

I wish I had known that earlier. I wish I had been prepared for the emotional gauntlet, for the euphoria, the doubt, the crushing weight of expectation. I wish I had built with an exit in mind from the start—not because I wanted to sell, but because I wanted to ensure that, if the moment came, I would hold the power, not the buyer.

Three years later, we did exit. On our terms. With multiple offers in hand. But that only happened because we stepped back, rebuilt, and structured our company for resilience. Because we learned the hardest lesson of all: that a deal should never define you. That the smartest move is sometimes to walk away. And that the real prize isn’t the exit.

It’s the ability to choose.

If you are considering selling, keep your head clear. Don’t let the numbers cloud your judgment. Assess every step, and never let desperation replace discipline. And most of all—never forget why you built your business in the first place. If you do decide to sell, do it on your terms. Build something unshakable. Because in the end, the goal isn’t just to exit.

It’s to have the power to decide when, and if, you ever want to.

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