Millionaire Timothy (or Tim) Armoo made his first fortune at 17, before he could even legally vote. He blew through every penny of it before he turned 19.
“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.”
Despite arriving in the U.K. as a child with no money, no network, and years of instability behind him, Armoo started his first business—a tutoring service—at 14 and scaled it to 65 tutors within six weeks. Then he built Entrepreneur Express, a publication he sold to Horizon Media at 17 for a life-changing amount.
“That company got bought for £110,000. I’m this kid from like South London, I was like, bro, this is £110 million,” he added. “So I got cocky, I got arrogant, and I started to invest it in stuff that I had absolutely zero clue about.”
Convinced his early success meant he’d unlocked the secret hack to building wealth fast, he tried to turn his newfound fortune into passive income. He poured some of it into a dentist affiliate website he was convinced would take off. It didn’t. Then he tried spread betting next.
“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.”
Eventually he made his money back, and more, the only way he really knew how to: by building another business.
In 2017, while most of his university peers were out partying, he spent his second year founding Fanbytes, an influencer marketing agency that went on to land clients like the U.K. government, Deliveroo, and Samsung. Brainlabs acquired it in 2022 for an eight-figure sum, when Armoo was just 27.
Armoo tells founders who feel empty after selling out to go hug their money
For years, Armoo had zero sympathy for founders who described feeling hollow after a big exit. Then he sold Fanbytes and found out for 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.”
And for about six months after the sale, Armoo felt “on top of the world.” But then the hollowness he’d once mocked finally 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, wasn’t the overnight wealth—it was that he’d been so busy in build-mode, he hadn’t considered what life would actually look like after the sale.
“It was just build business, sell business, make money, die,” Armoo said. “It was just like there was nothing afterward.” He found himself asking: Who am I without the business? And what will he do for work, now that he doesn’t actually have to work?
“I had to work really hard to not tie who I was to my achievements,” Armoo said, while adding that it took around a year to separate his big win from his ego. “That was a big thing… I had to go through quite a lot of mental change, psychological change.”
Armoo isn’t the only founder who’s struggled to separate his identity from his achievements
Armoo’s “who am I without the business” spiral isn’t unique to him.
Arianna Huffington, who spent over a decade building Huffington Post into one of the biggest names in digital media before walking away in 2016 to found Thrive Global, has said she’s seen countless executives go through the same struggle. Some, she told Fortune, even stay stuck in jobs they no longer love, purely 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.
Growing up, Brian Chesky, the cofounder and CEO of Airbnb, said he “desperately wanted to be successful” because he thought it would bring him adoration. Plus, having social worker parents who were by no standards rich, he also thought a large sum of money could “solve every problem.” But actually, he said the company’s blockbuster 2020 IPO—despite making him a billionaire—was “one of the saddest periods” of his life.
Meanwhile, Loom cofounder Vinay Hiremath hit a similar wall after selling his company to Atlassian for $975 million. In a blog post candidly titled “I am rich and have no idea what to do with my life,” he described the identity collapse that followed the company’s rapid rise and eventual sale. “I lost myself,” he wrote, adding that the windfall left him with “infinite freedom” but no idea what to do with it.
