Bootstrapped 20 Years to Life Changing Exit | Simon Swords

Resources mentioned

• Simon on LinkedIn: linkedin.com/in/simonswords
• Fundipedia: fundipedia.com
• FE fundinfo (acquirer): fefundinfo.com
• The IA Engine: theiaengine.com
• Practical Founders Podcast: The Grind Behind a Stellar SaaS Exit in the UK

Key timestamps

(02:00) Why bootstrapping for 20 years was the making of him
(07:31) Cumulative childhood trauma and growing up in Dagenham
(11:30) Anxiety as a superpower in business
(12:59) "I would have rather died than given up"
(15:38) Thinking he was having a heart attack on an onboarding call
(18:30) His chairman buying him out for a million pounds
(20:12) Waking up with the money and the anxiety still there
(21:52) The dragon he was chasing for 30 years
(23:30) Why most of his therapy came after success, not during
(28:30) Running the exit himself with ChatGPT
(32:31) What the cry on closing day was really about
(34:56) Why once you have money, you're not allowed to be sad
(38:30) The friends who anchor him to reality
(42:23) The panic attack that made him stop
(45:30) His 2026 plan to fill the space the business used to occupy
(48:05) What he's most proud of

Episode summary

Simon grew up in Dagenham, a working-class part of East London where the local Ford factory was past its prime and the social fabric was fraying. He was a loner kid with a head brace, debilitating hay fever, and parents who didn’t always get along. He learned early on that the only person he could rely on was himself.

That self-reliance built him and broke him at the same time. He calls himself a solutions-orientated kid, constantly ideating about how to fix things. By 18 he was selling computers. By his early twenties he'd cycled through web design, custom software, and a few failed ventures. In 2008, a client called Investec asked him to build a fund data platform for buy-side asset managers. He kept the IP. That became Fundipedia.

In the early years, Simon ran three businesses at once. Atlas, the bespoke dev shop. Staff Squared, an HR SaaS. And Fundipedia. He was scattered, exhausted, and by his own admission, doing all three badly. The turning point came when his mentor John Farrow called him negligent for ignoring Fundipedia's potential. There were leads sitting unanswered in the inbox. He got focused. The business started to climb.

In 2019, Fundipedia landed HSBC after a brutal two-year enterprise sales cycle. The contract was a tenfold step up in client size. During one onboarding call, Simon thought he was having a heart attack. His response was to finish the call before deciding whether to go to the hospital. He tells that story not for shock value, but as a small example of the magnitude of pressure he'd been carrying for over a decade and just considered normal.

A few years in, his chairman John could see what was happening. Simon had 99% of his net worth tied up in the business. Some of his staff were earning more than he was. John offered to buy a chunk of his shares for around a million pounds so Simon could finally take some skin out of the game. Simon took the deal. He thought it would bring relief. It didn't. He remembers waking up one morning and realizing the anxiety was still there.

That's when he started seeing a psychiatrist. He talks openly about being diagnosed with generalised anxiety, emotional dysregulation, catastrophic thinking, and a fragile sense of self. He'd been carrying all of it his whole life. The dragon he was chasing, it turned out, wasn't the next milestone. It was the version of himself that finally felt safe.

In May 2025, after turning down an earlier offer he thought undervalued the business, Simon sold Fundipedia to FE fundinfo. He negotiated the entire deal himself with his chairman and a ChatGPT subscription. Twenty thousand pounds in legal fees, a small accountancy bill, and a fifteen-quid-a-month AI tool. No corporate broker. When the deal closed, he cried. Not from relief. From decades of pain finally letting go.

A friend gave him the metaphor that stuck. For every year you spent in the trenches, you need a month to decompress. Imagine a deep sea diver coming up too fast and getting the bends. That's what Simon did after the exit. He tried to jump straight back into new ventures and lasted twelve weeks before nearly having a panic attack in a public place. His wife told him she'd been watching him wind himself up again and was relieved when he stopped.

We talk about the part of post-exit life nobody warns you about. Why once you have money and options, you feel like you're no longer allowed to be sad. How you lie to friends about what things cost so they'll still come along. Why he uses the phrase "the elephant is gone but the bones are still crushed by it" to describe how he feels almost a year later. And what he's doing now to fill the space the business used to occupy. A half Ironman, a metal band, a chess tournament, a car he's building, two businesses he's mentoring on his own terms.

When I asked what he's most proud of, he said two things. Not having given up. And the emotional connections he made with people along the way. The staff who've been with him for nearly twenty years. The friends who anchor him to reality. The little fleeting moments of connection. Not the money, not the exit. Though those are certainly nice to have.

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