Tom Grogan, a 35-year-old British entrepreneur, should have been living the dream. In 2024, he sold his stake in Wingstop UK for a staggering $532 million, securing the kind of fortune that most in the FIRE (Financial Independence, Retire Early) movement aspire to. Yet, just months later, he found himself “bored” and unfulfilled—proof that money, while liberating, doesn’t always buy purpose.
Grogan, who started his career as a construction worker earning $5 an hour, built Wingstop UK from scratch after cold-emailing the Texas-based chicken-wing brand in 2017. The journey wasn’t easy: over 50 investors rejected his pitch before he opened his first outlet. Seven years and 57 restaurants later, his risk paid off spectacularly when a US private equity firm bought a controlling stake.
But the satisfaction was short-lived. Speaking to Fortune, Grogan described the aftermath of his big payday as “surreal” and “empty”. “It’s all you think about. And then when you get there, it’s like, okay, it’s done now—now what? Money doesn’t necessarily fill that void,” he said.
Grogan’s story echoes a broader trend among young millionaires who find that financial independence doesn’t necessarily lead to emotional contentment. The FIRE movement, popularised over the past decade by tech workers and entrepreneurs, preaches extreme saving and investing to enable retirement by one’s 30s or 40s. Its appeal lies in escaping corporate drudgery—but for some, like Grogan, the absence of work creates a new kind of void.
“You have to change your head from ‘we’re building a business’ to ‘we’re managing money’—and they’re two different skill sets,” he said. The shift from founder to investor left him disoriented. Despite the windfall, Grogan didn’t splurge on mansions or super cars; he still rents his home and spent the first half of the year simply reflecting on his next move with his co-founders.
Grogan admits he cannot imagine spending his days idly. “I can’t live life sat on a beach,” he said. “We need something to occupy our minds, to challenge ourselves. You need a purpose every day to wake up for.” His comments underline what psychologists describe as post-achievement depression—a dip in motivation after reaching a long-pursued goal.
He’s not alone. Airbnb CEO Brian Chesky has previously admitted that his company’s blockbuster IPO, which made him a billionaire, triggered “one of the saddest periods” of his life. After chasing success for years, Chesky said he found himself lonelier than ever.
Grogan’s reflections serve as a reality check for a generation idolising the FIRE lifestyle. Many early retirees discover that financial freedom can expose the deeper question of what to do with that freedom. While the movement emphasises autonomy, it often overlooks the human need for structure, challenge, and meaning.
Experts say that the healthiest form of “retirement” might not be about quitting work entirely, but about gaining the freedom to choose meaningful work—whether that means starting another business, mentoring, or pursuing creative ventures.
As for Grogan, he’s already preparing for a comeback—though likely outside the food and beverage industry. His fortune ensures he’ll never need to work again. But as he’s discovered, needing something to wake up for might just be the truest kind of wealth.
