Simon Swords bootstrapped Fundipedia for nearly 20 years before selling to FE fundinfo in May 2025. He started in a garden shed with an Ethernet cable and a VoIP phone, ran three businesses at once for years, and eventually landed clients like HSBC, Barclays, and Legal & General. He negotiated the entire life-changing exit himself with his chairman and a ChatGPT subscription, without a corporate broker.

In this episode, Simon and I go deep on what it actually costs to play the long game. We talk about the childhood that wired him to push through anything, why he says he would rather have died than given up, and why he cried the day the deal closed.

We also get into why he sought therapy after the business was successful, not during the struggle. And why he thinks once you have the money, you're no longer allowed to be sad.

This is a conversation about whether the exit actually sets you free, or whether the real work starts after. If you're playing the long game, this one's for you.

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(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

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

Connect with our host:

• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
• Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

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