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Asolica > Blog > Business > 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 | Fortune
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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 | Fortune

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Last updated: November 9, 2025 11:57 am
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1 month ago
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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 | Fortune
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Contents
  • From $5 an hour builder to multimillionaire sounds just like the dream—however this founder says ‘it’s boring’
  • Brian Chesky known as the Airbnb IPO ‘one of the saddest periods’ 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 resolve 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 each day 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 whole mind is occupied on making a success of this business,” Grogan completely informed Fortune. 

“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.”

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

“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,” he stated. “So we have to discover the world of financial instruments, stocks, bonds—all of that stuff that’s all new to us, but we’re being strategically careful.”

As a substitute of dashing to purchase a mansion or a fleet of quick automobiles, Grogan added that he’s nonetheless renting. And alongside together with his cofounders Herman Sahota and Saul Lewin, the trio gave the primary half of this 12 months to take a seat again and begin fascinated by what they need to do subsequent.

However one factor is for certain: 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 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.”

It’s why he’s already planning to get again to the grind—he doesn’t know what his subsequent enterprise shall be, “but it probably won’t be in the world of food and beverages.”

Brian Chesky known as the Airbnb IPO ‘one of the saddest periods’ of his life

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

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

Rising up, Chesky admits he “desperately wanted to be successful” as a result of he thought it could convey 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 “solve every problem.”

“I had this image that if I got successful I’d have all these people around me, all these friends, I’d have all this love, all this everything, and my life would be fixed,” he informed Armchair Professional podcast. 

However truly, when Airbnb hit that $100 billion valuation and “everyone in high school” 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.

“At the bottom of the mountain, you have hope,” he concludes of his journey from scrappy start-up founder to billionaire. “But the problem is when you get to the top of the mountain oftentimes you are at the top by yourself, disconnected.”

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