Sold his company for $532 million, but ‘bored’—Millennial bizman finds no joy in early retirement, returns to work

Tom Grogan, a 35-year-old entrepreneur, became a multimillionaire after selling a majority stake in Wingstop UK to a US-based private equity firm in a deal valued at £400 million ($532 million). Yet he says he has failed to find joy in early retirement and plans to return to work.

After nearly a decade of building the UK brand from scratch — from sending a cold email to Texas and facing 50 investor rejections to finally opening 57 restaurants — Tom Grogan told Fortune that navigating life after the sale has been an entirely different challenge.

“It’s all you think about. And then when you get there, it’s just a bit surreal. It’s like, Okay, it’s done now. Now what? And money doesn’t necessarily fill that void either,” says Grogan.

From a construction worker to a multimillionaire

The entrepreneur began his career as a construction worker, earning just $5 an hour, but fate had other plans. By his early 20s, he had become a founder. However, he admits that the change from being an entrepreneur to multimillionaire has been unexpectedly “slow-paced” and “boring.”

Tom Grogan founded Wingstop UK in 2018, a restaurant chain that primarily sells buffalo-style chicken wings, along with boneless wings, tenders, fries, and milkshakes.

He blames this feeling of emptiness on the sudden transition in his professional life: “You have to now change your head from we’re not business building anymore. We’ve gone from being an entrepreneur to managing money—and they’re two different skill sets,” he said.

After the stake sale, Grogan did not rush into buying a mansion or a fleet of fast cars, and still prefers renting. Together with his cofounders, Herman Sahota and Saul Lewin, he spent the first half of this year reflecting on what they wanted to do next.

But Grogan made one thing very clear: no matter what, he won’t be resting on his laurels or enjoying the fruits of his labour, because he finds this mindset plain “boring.”

He stressed, “I can’t live life sat on a beach. I think we need something to occupy our minds, to challenge ourselves. You need a purpose every day to wake up for, which we don’t have right now.”

For these reasons, he is already planning to get back to the grind, although he doesn’t know what his next venture will be. “But it probably won’t be in the world of food and beverages,” he hinted.

Brian Chesky felt a similar wave of sadness after Airbnb IPO

Tom Grogan is not the only founder who has been feeling emptiness after achieving such a massive milestone. In fact, Brian Chesky, the cofounder and CEO of Airbnb, previously shared how his company's IPO was “one of the saddest periods” of his life, even though it made him a billionaire, Fortune reported.

Growing up, Chesky admits he “desperately wanted to be successful” because he thought it would bring him adoration from people. He also belonged to a household that was by no standards rich, hence it was ideal for him to think that a large sum of money could “solve every problem.”

But when success actually knocked on his door, as Airbnb hit that $100 billion valuation and “everyone in high school” knew what he did, he was lonelier than ever, having poured all his energy into his work for up to 18 hours a day.