Chapter 2An Exit is Not the Silver Bullet You've Been Looking for
On a hot and humid spring night in April 2021, I was rocking my seven-month-old son to sleep for the eleventh time. With one hand I cradled him, and with the other I drafted an all-hands message announcing another round of layoffs. We were about to reduce the headcount from around fifty to twenty. It would be the second round of layoffs in a year, but this time I swore it would be the last. I promised myself I would never again fire people who had become my friends.
After the cuts, the company would technically break even, but I was spent. Seven years of nonstop running, endless fundraising and firefighting, and now the sleeplessness of new fatherhood had left me empty. Growth had plateaued, I was exhausted, and I feared I wouldn’t even make it to my son’s first birthday. I needed a way out.
At the time, I clung to a dangerous fantasy that many founders secretly hold: that an exit could magically solve everything.
You might be tired, bored, envious of a competitor’s big headline, or spooked by an unexpected inbound email—and convince yourself that selling is the obvious next move. But here’s the truth: M&A does not exist to give you closure, relief, or validation. Potential acquirers don’t care about your burnout. They certainly didn’t care about mine. What awaited me instead was a painful four-year slog through the harsh realities of the acquisition process.
If your company has plateaued or you want to retire, you need to understand the math. Most private equity firms won’t even look at you unless you’re clearing $2–5M EBITDA, or $10M+ in recurring revenue with healthy margins sustained over years. And even then, they may require you to stay for six months to a year to transition and train new management. Below those thresholds, your company isn’t buyable—it’s fixable. Your job is to improve it until it clears the bar. Even if you have hit the numbers, selling might not be the smartest option. In many cases, hiring professional management and collecting dividends is a far better outcome than handing over the keys.
Another illusion is what I call the competitor headline trap. You see someone in your space announce an acquisition and assume you’re next. In reality, that deal usually means there’s now one fewer buyer available. Acquirers spend months—sometimes years—digesting a single acquisition before they make another move. Their spree is over, at least for now.
And then there are inbound emails. They often arrive out of nowhere, dressed up as “exploring synergies” or “wanting to learn more about your market.” Founders get excited, start imagining terms, and talk themselves into believing it’s their moment. But most of the time, those emails are fishing expeditions. Corporate development teams are gathering intelligence, not offering lifelines. Even when the interest is genuine, the emails usually go out to every player in your space. After a couple of conversations, once they’ve learned what they need, the replies stop. That’s not betrayal—it’s just how corporate development works.
Of course, there are rare exceptions. Every so often, an email comes directly from the CEO or founder of a company you respect, or through a trusted investor introduction. Those signals are stronger, but even then, caution is essential. Any serious acquirer will also be evaluating multiple targets. Deals collapse all the time, even after late-stage meetings and signed term sheets. Until the definitive agreement is inked and the money actually hits your account, nothing is real.
The lesson is this: don’t trick yourself into believing an exit is the cure for fatigue, a stagnant business, or the fear of missing out. M&A is not an emotional solution. It’s a transaction that happens only if the numbers work and you solve a problem the buyer can’t solve on their own. Until then, an exit isn’t a parachute or a reset button. It’s just a pipe dream.