Joys of Compounding
Episode 12 Bootstrapped European Software Investing
Joys of Compounding

Episode 12: Bootstrapped European Software Investing

Joys of Compounding

Episode 12

Bootstrapped European Software Investing

Oliver Thomas is the Founder and Managing Partner of Expedition Growth Capital. We cover the formative experiences in his education and early career, how he built a business from the idea of bootstrap investing, and what advice he'd give to aspiring builders of investment firms.

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(00:00:00) Welcome to Art of Investing

(00:04:00) First question - Reflecting on an upbringing in Wales

(00:12:33) The impact of sports during early years

(00:18:33) Finding motivation and drive at a young age

(00:24:09) Gaining insights into growth equity

(00:23:44) Tracing the evolution of bootstrap investing

(00:36:26) Key elements of successful bootstrap investing

(00:47:37) Examining the 'likability factor' in equity capital

(00:51:58) Introducing Expedition and its practices  

(00:59:25) Offering guidance for establishing an investment firm

(01:03:33) Highlighting favorite bootstrap companies collaborated with

(01:12:21) Exploring AI's role in bootstrapped companies

(01:16:11) Recommending inspirational resources

Bootstrapped European Software Investing

Introduction

Rick
Our teacher today is Oliver Thomas, Founder and Managing Partner of Expedition Growth Capital, a leading growth equity firm based in London and built to serve the next generation of capital-efficient, founder-led European software companies. Oli and I first met just over 20 years ago while we were both getting our MBA, and I quickly recognized I had stumbled on a human compounding machine of the highest quality and character.

Since then, I've sought to align myself both personally and professionally with him in as many ways as possible. This includes serving on Expedition's LP Advisory Committee, building companies together, including most recently Upliift Group and perhaps most importantly, having the great honor of being godfather to one of his wonderful daughters.

With that disclaimer, and my biases made crystal clear, I thought this class was just jam-packed with colorful stories, insightful career advice and lots of other helpful learnings, including a history on the bootstrap growth investing landscape that goes all the way back to the late '70s and originated by a woman named Jacqueline Morby while working at TA Associates, the archetype of bootstrap software companies and their elements of differentiation versus VC-backed peers, which tend to be better funded but more fragile due to capital dependency and finally, what it takes to win as an investor in this fascinating and attractive small corner of the market. With that, I hope you enjoy our class with the excellent European software investor and my good friend, Oliver Thomas.

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