🤩 A-ha – “Take On Me”
🙉 Dexys Midnight Runners – “Come On Eileen”
🕺🏻 PSY – “Gangnam Style”
Put your music tastes aside—each of these tracks blazed up the charts and burned into public memory, complete with questionable dance routines and cultural footprints. They were unforgettable, often unrepeatable, and very, very hard to follow up.
I had a chat with a founder who experienced something similar—but in the startup world.
His first business hit product-market fit (PMF) almost effortlessly. The product landed cleanly, grew fast, and exited well. But now on his third venture, he’s finding that lightning doesn’t always strike twice. This one’s a grind.
In the back of my mind, I was thinking:
“Welcome to the real world.”
But to be fair, he’s in good company. Even Steve Jobs had a one-hit wonder moment.
Even Legends Have to Restart
Jobs struck gold early with the Apple II. It wasn’t just a success—it carried Apple through its early years. But after that? The path wasn’t so easy. The Lisa tanked. The Macintosh floundered before finding its feet. He was fired from his own company.
Then came NeXT (commercially underwhelming) and Pixar, which eventually soared—but only after years of pain and pivoting.
Despite the myth, Jobs didn’t ride a constant upward curve. He built, failed, adapted, and waited. His second and third acts were hard-earned.
The Second (or Third) Time’s Not Easier—It’s Different
In business, we sometimes think early success means we’ve cracked it. But success is deeply contextual:
- Markets shift
- Timing changes
- What worked before may now be irrelevant
- The expectations are higher
- And we’re not the same founders we were the first time round
I’ve experienced this personally. I’ve been through three iterations of the same core product, each shaped by deeper insights and (let’s be honest) hard lessons. I’m only now feeling like it’s truly coming together.
Blimey—it took a while.
Long Term Commitment to Failing, and Learning
Even if you score a breakout hit early on, building a lasting business is a different beast. It requires:
👊 Solving real market problems (not just shipping cool tech)
🙋 Listening as needs evolve
🕹 Accepting that you can’t control everything
Founders who succeed long term don’t just chase the next big thing—they stay curious, they experiment, and they learn how to stay in the game even when it’s not glamorous.
The founder I spoke to? He’ll crack it. It won’t be a chart-topping one-hit like his first, but something richer and more sustainable. And no, I doubt he’ll be breaking into a PSY-style shuffle anytime soon.
