Tom Grogan, a 35-year-old entrepreneur, has become a multi-millionaire after selling a majority stake in Wingstop UK to an American private equity firm worth £400 million ($532 million). Still, he says he hasn’t been able to find joy in early retirement and plans to return to work.
After nearly a decade of building the British brand from scratch—from cold-emailing Texas and facing 50 rejected investors to finally opening 57 restaurants—Tom Grogan told Fortune that navigating life after the sale was a completely different challenge.
“It’s all you think about. And when you get there, it’s kind of surreal. It’s like, OK, now it’s done. Now what? And money doesn’t necessarily fill that void, either,” Grogan says.
From construction worker to multi-millionaire
The entrepreneur began his career as a construction worker, earning just $5 an hour, but fate had other plans. He became a founder in his 20s. However, he admits that the change from entrepreneur to multi-millionaire was unexpectedly “slow” and “boring”.
Tom Grogan founded Wingstop UK in 2018, a restaurant chain that primarily sells buffalo-style chicken wings, along with boneless wings, delis, fries and milkshakes.
He blames this sense of emptiness on the sudden transition in his professional life: “Now you have to change your mind because we’re not building a business anymore. We’ve gone from being an entrepreneur to managing money – and those are two different skill sets,” he said.
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After selling his stake, Grogan didn’t rush into buying a mansion or a fleet of fast cars and still prefers to rent. Along with his co-founders Herman Sahota and Saul Lewin, he spent the first half of this year thinking about what they want to do next.
But Grogan made one thing clear: regardless, he won’t be resting on his laurels or enjoying the fruits of his labor because he finds that mindset “boring.”
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He stressed: “I can’t live life sitting on the beach. I think we need something to occupy our minds to challenge us. Every day you need a goal to wake up to, which we don’t have now.”
For these reasons, he is already planning to return to the grind, although he does not yet know what his next venture will be. “But it probably won’t be in the world of food and drink,” he suggested.
Brian Chesky felt a similar wave of sadness after Airbnb’s IPO
Tom Grogan isn’t the only founder to feel empty after reaching such a massive milestone. In fact, Airbnb co-founder and CEO Brian Chesky previously shared that his company’s IPO was “one of the saddest times” 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 the admiration of people. He also belonged to a household that was not rich at all, so it was ideal for him to think that a large sum of money could “solve every problem”.
But when success really came knocking on his door, when Airbnb reached a $100 billion valuation and “everyone in high school” knew what he had done, he was lonelier than ever, pouring all his energy into his job, up to 18 hours a day.
