E20 — Six Exits in 30 Years with Matt Colebourne

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E20 — Six Exits in 30 Years with Matt Colebourne

"You don't need to leave. Acknowledge that you're not brilliant at everything and bring in a team who have the skillset and the experience that you don't, and let them do the job."

Apr 23, 2025

Transcript

A reminder. This substack has two sections:

Unconditionally Human (essays on Sundays) about AI-first startups, coaching, etc.
Startup CEO Succession (this podcast).

You can (un)subscribe to them individually.

While AI is all the hype today, Matt Colebourne founded and sold an AI startup 30 years ago. Since then, he put five further exits under his belt as a professional CEO who’s often brought in to turn around struggling firms or scale promising ones.

Needless to say, as both a founder CEO and a professional CEO, Matt has a lot to say about CEO successions. One of the key lessons? Founder CEOs don’t have to rush to leave. There’s a false narrative among some entrepreneurs but especially investors that once the company starts to scale, it’s time to bring in professional management.

The truth is, no CEO knows it all or has all the required skills. However, as long as they are willing to surround themselves with even more capable people and get out of the way, they have a chance of focusing on what they’re uniquely good at.

I’m grateful to Matt for sharing his hard-earned wisdom from his 30-year career (that’s not nearly over yet!).

Enjoy the conversation!