In a remarkable business success story, 35-year-old entrepreneur Tom Grogan has become a multimillionaire after selling his majority stake in Wingstop UK to a US-based private equity firm. The landmark deal was valued at an impressive £400 million (approximately $532 million), yet Grogan reveals an unexpected emotional struggle following his financial windfall.
The Unfulfilling Taste of Success
After nearly a decade of building the UK brand from scratch, Grogan finds himself surprisingly discontent with early retirement. The entrepreneur, who faced 50 investor rejections before ultimately establishing 57 restaurants, shared with Fortune that life after the sale has presented completely new challenges.
"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," Grogan confessed about his post-sale experience.
From Construction Sites to Restaurant Chains
Grogan's journey to multimillionaire status is particularly inspiring. He began his career as a construction worker earning just $5 per hour, but his entrepreneurial spirit emerged in his early 20s when he became a founder. He established Wingstop UK in 2018, creating a restaurant chain specializing in buffalo-style chicken wings, along with boneless wings, tenders, fries, and milkshakes.
The transition from hands-on entrepreneur to wealthy investor has proven unexpectedly "slow-paced" and "boring" for Grogan. He attributes his emptiness to the sudden shift in his professional identity: "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."
Not Alone in Post-Success Emptiness
Grogan isn't the only successful founder to experience this phenomenon. Brian Chesky, cofounder and CEO of Airbnb, previously described how his company's IPO represented "one of the saddest periods" of his life, despite it making him a billionaire.
Chesky grew up believing financial success would bring him admiration and solve all problems. However, when Airbnb reached its $100 billion valuation and achieved widespread recognition, he found himself lonelier than ever, having dedicated up to 18 hours daily to his work.
Unlike typical sudden wealth stories, Grogan didn't rush to purchase luxury mansions or expensive car collections. He still prefers renting and spent the first half of this year reflecting on future plans with his cofounders, Herman Sahota and Saul Lewin.
Grogan made his position clear: "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, the young multimillionaire is already planning his return to business, though he hints that "it probably won't be in the world of food and beverages." His story serves as a powerful reminder that financial success alone doesn't guarantee happiness or fulfillment.
