Millionaire Timothy Armoo Lost His First Fortune in 15 Months

Timothy Armoo sold his first company for £110,000 at 17—and lost every penny of it within 15 months.

"I made my first bit of money at 17—that was the first business that I meaningfully sold," Armoo told Fortune. "And then I lost all that money from that."

Armoo arrived in the U.K. as a child with no money and no network. At 14, he started a tutoring service and scaled it to 65 tutors within six weeks. At 17, he sold Entrepreneur Express, a publication he built, to Horizon Media. The deal changed how he saw himself.

"That company got bought for £110,000. I'm this kid from like South London, I was like, bro, this is £110 million," he said. "So I got cocky, I got arrogant, and I started to invest it in stuff that I had absolutely zero clue about."

The losing streak

Convinced he had unlocked a shortcut to building wealth, Armoo chased passive income. He poured money into a dentist affiliate website he believed would take off. It didn't. Then he turned to spread betting.

"I thought, I did it before, so I'm just going to do it again," Armoo explained. "I thought I knew how to make money, and spread betting seemed like an easy way to make money… Silly. Within 12 to 15 months, all of it was gone."

He made the money back the only way he knew how: by building another business. In 2017, during his second year of university, he founded Fanbytes, an influencer marketing agency. The firm went on to land the U.K. government, Deliveroo, and Samsung as clients. Brainlabs acquired Fanbytes in 2022 for an eight-figure sum, when Armoo was 27.

The hollow exit

For years, Armoo had dismissed founders who described feeling empty after selling. Then he sold Fanbytes and felt it himself.

"When I was building, I'd read these stories of people saying they felt empty after selling a business, and I'm like, okay, mate, all right," he said. "If you're empty with £10 million in the bank, okay, baby, go hug your money, and you wouldn't feel empty."

He felt "on top of the world" for about six months after the sale. Then the hollowness he had once mocked caught up with him. "I definitely had that. Oh, now what? And that 'now what?' was there for about two years."

The problem, he says, was not the wealth. It was that he had never planned for life after the sale.

"It was just build business, sell business, make money, die," Armoo said. "It was just like there was nothing afterward."

"I had to work really hard to not tie who I was to my achievements," he said. Separating the win from his ego took around a year. "That was a big thing… I had to go through quite a lot of mental change, psychological change."

A pattern among founders

Armoo's identity crisis is common among exited founders. Arianna Huffington, who left Huffington Post in 2016 to found Thrive Global, told Fortune she has watched executives stay stuck in jobs they no longer love because leaving feels like losing themselves.

"I have CEO friends who've stopped loving their jobs, but they're afraid to leave," she said. "The financial trap is much easier to see, while the identity trap is less tangible but no less real."

"They're so identified with the CEO role, or the anchor of an evening show, or whatever big job comes with a lot of recognition—it's become their identity," she added.

Airbnb cofounder and CEO Brian Chesky said he "desperately wanted to be successful" growing up, believing money could "solve every problem." Instead, the company's blockbuster 2020 IPO—which made him a billionaire—was "one of the saddest periods" of his life.

Loom cofounder Vinay Hiremath hit the same wall after Atlassian bought his company for $975 million. In a blog post titled "I am rich and have no idea what to do with my life," he wrote: "I lost myself." The windfall gave him "infinite freedom" but no idea what to do with it.

Armoo's trajectory—two exits, one wipeout, and a two-year identity crisis—suggests the hardest part of a big sale often begins after the wire hits the account.