#74 Serial Entrepreneur Phil Hollingdale - Risk, Resilience and a £170m Exit cover art

#74 Serial Entrepreneur Phil Hollingdale - Risk, Resilience and a £170m Exit

#74 Serial Entrepreneur Phil Hollingdale - Risk, Resilience and a £170m Exit

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What does it take to risk everything — your home, your family’s security, and even walk away from a million-pound payday — in pursuit of something bigger?

In this episode of The Bulletproof Entrepreneur, Phil shares the raw truth behind decades of building, selling, and reinventing businesses. From sleeping on an office couch to securing one of the UK’s biggest fintech exits, his journey is a masterclass in risk, resilience, and relentless drive.

We also get into the tough questions:

  • Why most startups never make it — and what separates those that do.
  • How policy decisions can shape the future of entrepreneurship in Britain.
  • The one skill that underpins every business success.

This isn’t a story of overnight wins. It’s a story of calculated gambles, painful setbacks, and bold moves that paid off in ways few would dare imagine.

Resources:

  • Shoe Dog by Phil Knight (founder of Nike)
  • Play Nice But Win by Michael Dell
  • Phil's LinkedIn


This podcast is produced by GR Media
Sponsored by Capital Asset Management
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