See on Linkedin

Recently, over cold coffee and surprisingly enthusiastic networking, I found myself in conversation with a fascinating character. He was one of those people who quietly drop bombs of wisdom between stories, without even realising it.

This chap had studied engineering, only to pivot into law—a dramatic enough career shift. But he didn’t stop there. After landing a plush job at a major U.S. law firm (the kind that makes your bank manager smile just hearing about it), he decided the corporate ladder wasn’t quite the climb for him. So, naturally, he started his own finance company.

By 2007, his business was flourishing, and the offers to buy him out were… let’s just say, very generous. But he declined. “It’s my baby,” he said. And then came 2008—the global banking crash. He lost everything!

Fast forward to another encounter, this time with someone I met through a friend at a casual gathering (which, as it turns out, was far more educational than most webinars I've attended). This man and his wife had spotted a quirky delicatessen name on a U.S. road trip and thought, “Wouldn’t that make a great pub name?”—despite knowing absolutely nothing about the hospitality industry. Naturally, they opened a pub.

It was an instant hit. Child-friendly, warm, busy. They repeated the model eight times over. A brewery swooped in with a tempting offer. He sold the lot—on the condition he didn’t compete in the area for five years.

So, he went elsewhere. Bought another pub. Asked the locals what they wanted. Built again. Seven pubs later, a private equity firm came calling. Deal done.

And just when you think the tale ends, he circled back to his original turf. The old chain? Gone. So, he did what any sane person would do (if they had nerves of steel and the foresight of a chess grandmaster): started over again. New pubs. Local insight. Same formula. He sold the third chain in January 2020.

March 2020: COVID-19 lockdown. Hospitality hit rock bottom.

When I asked him the secret to his three-time success, he didn’t mention strategy, or spreadsheets, or Silicon Valley-grade innovation. He said this:

“Getting in is easy. You listen, you build, you adapt. But the real skill? Knowing when to get out. Never treat the company as your baby—because you’ll never let go. And when the world changes, you’ll miss the signs.”

That stuck with me.

You see, I’ve watched friends build start-ups across tech, health, media—you name it. The founding spark is always bright: risk, passion, personal investment. But somewhere between beta-testing and Series B funding, something shifts. The founder starts to believe only they can lead it forward. And suddenly, progress stalls.

Research backs this up. Founders often struggle to scale their businesses beyond a certain point, partly due to over-attachment and partly due to skill mismatch (Wasserman, 2012). The very qualities that make someone a great founder—vision, grit, belief—can be the same traits that hold them back from being a great CEO.

So, here’s the uncomfortable truth: your business is not your baby. It’s your venture. Your creation, yes. But also, your asset. And like any asset, its value often depends on your ability to know when to grow, when to pivot—and when to let go (DeTienne, 2010).

After all, exits aren’t failures. They’re strategy.

And maybe—just maybe—the smartest entrepreneurs are the ones who build with one hand on the wheel… and the other already reaching for the parachute.

The exit is mightier than the launch.

References:

DeTienne, D.R. (2010) ‘Entrepreneurial exit as a critical component of the entrepreneurial process: Theoretical development’, Journal of Business Venturing, 25(2), pp. 203–215.

Wasserman, N. (2012) The Founder’s Dilemmas: Anticipating and Avoiding the Pitfalls That Can Sink a Startup. Princeton University Press.