Billions From selling his company to Booking.com to building a fintech unicorn! - Arthur Waller
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Jan 23, 2026 
Arthur Waller, a serial entrepreneur and co-founder of fintech unicorn Pennylane, shares his journey from selling his first company to Booking.com to tackling the accounting industry. He reveals the power dynamics among co-founders and discusses fundraising strategies that minimize dilution. Arthur emphasizes transforming accountants from adversaries into allies, while navigating the complexities of European expansion. He also touches on the importance of remaining private versus going public, and offers invaluable advice for aspiring founders.
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Exit Via Earn-Out And Learning At Booking
- Arthur sold PriceMatch to Booking.com and received most value through stock appreciation rather than upfront cash.
- He stayed ~3.5 years at Booking to run the business and learn how large tech product teams operate.
Pick Replaceable Problems In Huge Markets
- Choose markets that are huge, software-friendly, and where you can replace an existing painful solution.
- Arthur prioritized market size and replaceability to maximize long-term upside for his next company.
Raise Early To Build A Bigger Cake
- Raising from day one can be fine if your goal is to build a huge company and you value growth over ownership.
- For PennyLane the founding equity split reflected previous exits and who joined at ideation versus later.