He sold his company for ₹4,680 crore to live the dream but still feels a 'void': UK entrepreneur says 'I can't live life sat on a beach'

For most people, selling a business for billions is the ultimate dream — the kind that ends with beachfront villas, luxury cars, and a lifetime of leisure. But for UK entrepreneur Tom Grogan, that fantasy quickly turned into something he didn’t expect: emptiness.

The Wingstop UK co-founder, who sold a majority stake in his company for £400 million (around ₹4,680 crore), recently told Fortune that despite the massive windfall, retirement didn’t feel fulfilling. “For seven years, your whole mind is occupied with making a success of this business,” he said. “And then when you get there, it’s just a bit surreal. It’s like, okay, it’s done now. Now what? Money doesn’t necessarily fill that void either.”

From £5-an-hour worker to millionaire, but ‘it’s boring’
Grogan’s story reads like a modern business fairy tale — a young man who started as a construction worker earning just £5 an hour, co-founded a fast-growing restaurant chain, and turned it into a nationwide success. But after the deal was sealed and the excitement faded, he found himself restless.

“You have to now change your head from business building to managing money,” he explained, adding that it’s a completely different world involving “financial instruments, stocks, bonds.” Unlike what one might imagine, he hasn’t splurged on mansions or supercars — he’s still renting and taking time to plan his next move.

“It’s boring,” Grogan admitted. “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.”

Why wealth doesn’t guarantee fulfillment
Grogan’s reflections echo a growing sentiment among successful entrepreneurs who discover that financial freedom doesn’t necessarily equal happiness. Fortune also cited Airbnb CEO Brian Chesky, who confessed that the company’s $100 billion IPO — a moment that made him a billionaire — was “one of the saddest periods” of his life.

Chesky said he once believed success would bring admiration, love, and happiness, but instead found himself lonelier than ever after years of working 18-hour days. “I had this image that if I got successful, my life would be fixed,” he said on the Armchair Expert podcast.

Indian entrepreneur echoes similar struggle
The same feeling was shared by Siddharth Shankar, an Indian-origin entrepreneur based in London who sold his company Tails Trading for $500 million in 2024. In a candid conversation on , he revealed that after years of relentless work, the sudden slowdown was difficult to cope with.

“After 15 years of being constantly engaged, I struggled with the lack of purpose,” he said, jokingly adding, “How much PlayStation can one play? How much golf can I play?” Like Grogan, Shankar realised that the rush of building something couldn’t be replaced by leisure.

Both Grogan and Shankar’s stories highlight a rarely discussed truth about success — that purpose often matters more than profit. When the grind stops, what remains is not peace, but a silence that many find hard to live with.

As Grogan put it, “Money doesn’t fill the void. You still need something to wake up for.”