Tim Armoo made his first fortune at 17, before he was old enough to vote, and lost every penny of it before he turned 19. The British entrepreneur sold a publication called Entrepreneur Express to Horizon Media for £110,000, a sum that felt like a life-changing windfall to a teenager from South London. Within 12 to 15 months, the money was gone.
Armoo told Fortune that the loss stemmed from overconfidence rather than bad luck. «I got cocky, I got arrogant, and I started to invest it in stuff that I had absolutely zero clue about,» he said. He had started his first business, a tutoring service, at 14 and scaled it to 65 tutors within six weeks. That early success convinced him he had unlocked a repeatable formula for making money quickly.
He poured part of the £110,000 into a dentist affiliate website he believed would take off. It did not. He then turned to spread betting, a form of financial speculation, assuming his prior success would carry over. «I thought I knew how to make money, and spread betting seemed like an easy way to make money… Silly,» he said. «Within 12 to 15 months, all of it was gone.»
Armoo eventually rebuilt his wealth the only way he says he really knew how: by starting another company. In 2017, during his second year at university, he founded Fanbytes, an influencer marketing agency. While many of his peers were out partying, he was building a business that would go on to land clients including the U.K. government, Deliveroo, and Samsung. Brainlabs acquired Fanbytes in 2022 for an eight-figure sum, when Armoo was 27.
The second exit brought a different kind of challenge. For years, Armoo had dismissed founders who described feeling hollow after selling a business. «If you're empty with £10 million in the bank, okay, baby, go hug your money, and you wouldn't feel empty,» he recalled thinking. For about six months after the Fanbytes sale, he felt «on top of the world.» 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,» he said. The problem, he explains, was not the sudden wealth but the fact that he had been so focused on building that he never considered what life would look like after the sale. «It was just build business, sell business, make money, die. It was just like there was nothing afterward.»
He found himself asking who he was without the business and what he would do for work now that he did not have to work. «I had to work really hard to not tie who I was to my achievements,» he said, adding that it took about 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's experience is not unique among founders. Arianna Huffington, who built Huffington Post into a major digital media brand before leaving in 2016 to found Thrive Global, has said she has seen countless executives struggle with the same identity crisis. Some, she told Fortune, remain in jobs they no longer love because leaving feels like losing themselves. «The financial trap is much easier to see, while the identity trap is less tangible but no less real,» she said.
Brian Chesky, cofounder and CEO of Airbnb, has said he desperately wanted to be successful because he thought it would bring adoration and solve every problem. But the company's 2020 IPO, despite making him a billionaire, was «one of the saddest periods» of his life. Vinay Hiremath, cofounder of Loom, described a similar collapse after selling his company to Atlassian 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,» adding that the windfall left him with «infinite freedom» but no idea how to use it.
Armoo's advice to founders who feel empty after a big exit is blunt: go hug your money. But his own path suggests the recovery takes time, introspection, and a willingness to rebuild an identity that is not tied to a company's sale price.