Using ChatGPT During Due Diligence

Simon Swords founded Fundipedia after starting in a backyard shed building bespoke software. Originally a custom development shop, his firm built a data governance platform for major buy-side asset managers including HSBC, Barclays, and Legal & General.

Over time, Fundipedia evolved into a high-retention enterprise SaaS platform with strong net revenue retention and Rule of 40 performance. Simon navigated long consultative sales cycles, regulatory tailwinds, and a tightly networked financial services market to build a durable recurring revenue engine.

After turning down an initial offer, Simon grew ARR further and ultimately sold in 2024 at approximately 10x ARR. He exited fully, used ChatGPT extensively in diligence, and now reflects on endurance, discipline, and surviving long enough for luck to compound.

Key Takeaways

• Survive First — Don't make a mistake that kills you or the business. Staying alive creates the opportunity for luck to compound.
• Enterprise Patience — Two-year sales cycles are normal at the top end. Persistence and reputation matter more than speed.
• Rule Of 40 Discipline — Strong growth plus profitability gives founders leverage in exit timing and valuation.
• Problems Over Product — Founders obsess over product; buyers care about solving painful, expensive problems.
• Build To Exit Cleanly — Structure the company so it runs without you before you start acquisition conversations.

Quote from Simon Swords, Founder of Fundipedia

"I think the most important thing is not to make a mistake that kills you or the business. While you're in the arena and you've not been taken out yet, dragged off by the hyenas or lions, whatever they used back in the Roman days, you've still got a chance to make something magical happen. "You do something stupid, kill the business, kill your reputation, you're done. Entrepreneurs hate the word luck. I do feel luck. I am lucky. Of course I'm lucky. I have to be lucky. You make your own luck.

"But I'll tell you what I didn't do. I didn't make a mistake that killed me or the business and the entire way through. Even when I was going through hell, never, no matter how neurotic or anxious or all the negative kind of traits you can imagine would have flown through me. I never made a mistake that killed the business."

Links

• Simon Swords on LinkedIn
• Fundipedia on LinkedIn
• Fundipedia website
• FE fundinfo website

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