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Reading: After promoting his enterprise for $532 million, this millennial says a lifetime of leisure was surprisingly ‘boring’, so he’s selecting to return to work
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After promoting his enterprise for 2 million, this millennial says a lifetime of leisure was surprisingly ‘boring’, so he’s selecting to return to work
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After promoting his enterprise for $532 million, this millennial says a lifetime of leisure was surprisingly ‘boring’, so he’s selecting to return to work

Scoopico
Last updated: November 9, 2025 11:21 am
Scoopico
Published: November 9, 2025
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From $5 an hour builder to multimillionaire sounds just like the dream—however this founder says ‘it’s boring’Brian Chesky referred to as the Airbnb IPO ‘one of many saddest intervals’ of his life

This millennial has a message for anybody who thinks a million-dollar windfall—whether or not it’s from the sale of their enterprise or the $124 trillion Nice Wealth Switch—will remedy all of your issues. 

If that was the case, Tom Grogan ought to have been residing the dream. After cofounding Wingstop UK and promoting a majority stake for £400 million ($532 million), most individuals would count on him to get up daily feeling on high of the world. However the actuality? Removed from it. Wealth didn’t magically make life really feel full.

“For seven years, your complete thoughts is occupied on making a hit of this enterprise,” Grogan solely instructed Fortune. 

“It’s all you concentrate on. After which if you get there, it’s only a bit surreal. It’s like, Okay, it’s completed now. Now what? And cash doesn’t essentially fill that void both.”

After practically a decade of constructing a UK model from scratch—together with one chilly e mail to Texas, 50 investor rejections, and 57 eating places later—he admits that navigating life after the sale is a complete different problem.

From $5 an hour builder to multimillionaire sounds just like the dream—however this founder says ‘it’s boring’

Whereas Grogan’s rise from a building employee to a founder (all in his 20s) was meteoric, the transition from entrepreneur to multimillionaire has been… unexpectedly slow-paced, he admitted.

“You must now change your head from we’re not enterprise constructing anymore. We’ve gone from being an entrepreneur to managing cash—and so they’re two totally different ability units,” he mentioned. “So we now have to find the world of monetary devices, shares, bonds—all of that stuff that’s all new to us, however we’re being strategically cautious.”

As a substitute of dashing to purchase a mansion or a fleet of quick automobiles, Grogan added that he’s nonetheless renting. And alongside along with his cofounders Herman Sahota and Saul Lewin, the trio gave the primary half of this yr to take a seat again and begin interested by what they wish to do subsequent.

However one factor is for positive: He gained’t be resting on his laurels, having fun with the fruits of his labour and driving off into the sundown any time quickly.

“It’s boring,” Grogan provides. “I can’t stay life sat on a seaside. I feel we want one thing to occupy our minds, to problem ourselves. You want a goal daily to get up for, which we don’t have proper now.”

It’s why he’s already planning to get again to the grind—he doesn’t know what his subsequent enterprise might be, “but it surely in all probability gained’t be on this planet of meals and drinks.”

Brian Chesky referred to as the Airbnb IPO ‘one of many saddest intervals’ of his life

Grogan isn’t alone in feeling the vacancy that may observe an enormous milestone. Years of relentless focus and sweat poured right into a single enterprise can depart an odd void when it’s out of the blue previous the end line.

In actual fact, Brian Chesky cofounder and CEO of Airbnb, beforehand admitted that his firm’s IPO—regardless of making him a billionaire—was “one of many saddest intervals” of his life. 

Rising up, Chesky admits he “desperately needed to achieve success” as a result of he thought it will deliver him adoration. Plus, having social employee mother and father who have been by no requirements wealthy, he additionally thought a big sum of cash might “remedy each downside.”

“I had this picture that if I received profitable I’d have all these individuals round me, all these mates, I’d have all this love, all this every part, and my life could be fastened,” he instructed Armchair Knowledgeable podcast. 

However truly, when Airbnb hit that $100 billion valuation and “everybody in highschool” knew what he did, he was lonelier than ever, having poured all his vitality into his work for as much as 18 hours a day.

“On the backside of the mountain, you might have hope,” he concludes of his journey from scrappy start-up founder to billionaire. “However the issue is if you get to the highest of the mountain oftentimes you might be on the high by your self, disconnected.”

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