The surprising boredom of selling your business for $532 million

According to Fortune, Tom Grogan co-founded Wingstop UK and sold a majority stake for £400 million (about $532 million) after seven years of building the business from scratch. The 20-something entrepreneur went from construction worker to multimillionaire through a journey that included one cold email to Texas and 50 investor rejections before opening 57 restaurants. Despite the massive financial success, Grogan found life after the sale surprisingly boring and unfulfilling, describing the transition as “surreal” and admitting money doesn’t “fill that void.” He’s still renting rather than buying mansions or fast cars, and after taking the first half of this year off with cofounders Herman Sahota and Saul Lewin, he’s already planning to return to work. Grogan confirmed his next venture probably won’t be in food and beverages.

The entrepreneurial void

Here’s the thing about building something massive – it consumes your entire identity. Grogan spent seven years where the business was “all you think about,” and when that suddenly disappears, what’s left? It’s like running a marathon and then just… stopping. No more training, no more goals, just this weird emptiness where your purpose used to be.

And he’s not alone in this feeling. Brian Chesky from Airbnb described his company’s IPO as “one of the saddest periods” of his life, despite becoming a billionaire. He thought success would bring him “all these people around me, all these friends, I’d have all this love.” Instead, he found himself lonelier than ever after pouring 18-hour days into his work for years.

Money doesn’t fix everything

Look, we all fantasize about what we’d do if we suddenly had millions. But Grogan’s experience shows that the reality is often different. He’s still renting, not buying mansions. He’s not collecting supercars. Instead, he’s discovering that managing wealth requires “a whole different skill set” from building businesses.

Basically, going from entrepreneur to money manager means learning about “financial instruments, stocks, bonds – all of that stuff that’s all new to us.” It’s a completely different game, and one that many founders aren’t particularly excited to play. The thrill isn’t in preserving wealth – it’s in creating it.

The need for purpose

Grogan puts it bluntly: “I can’t live life sat on a beach.” He needs “something to occupy our minds, to challenge ourselves.” That daily purpose to wake up for is what’s missing now. And honestly, how many of us would feel the same?

Think about it – we spend our lives chasing financial freedom, but what happens when we actually achieve it? Chesky described it perfectly: “At the bottom of the mountain, you have hope. But the problem is when you get to the top of the mountain oftentimes you are at the top by yourself, disconnected.”

Back to the grind

So what’s next for someone who’s already achieved what most entrepreneurs dream of? Grogan is already planning his return to work, though he’s wisely avoiding the food and beverage industry that made him rich. Smart move – why compete with your own success story?

The real question is whether the second act can ever match the thrill of the first. Building something from nothing has a certain magic that’s hard to replicate. But for entrepreneurs like Grogan, the alternative – sitting around being rich – seems even less appealing. The chase, it turns out, might be more satisfying than the catch.