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How to Be a Serial Entrepreneur | Rob Finlay
Rob Finlay is a serial entrepreneur, investor, and bestselling author of Beyond the Building and Hey, Dad…, a life-advice book inspired by his journey as a father of four. Over the past 25+ years, he’s built and successfully exited four companies, pioneered debt optimization strategies in commercial real estate, and founded Thirty Capital and Defease With Ease, helping advise billions in transactions. Today, Rob’s focus spans AI, data analytics, leadership, and sustainable agriculture — proving that business success and long-term impact can go hand in hand.
In this episode of Startup or Shutup!, host Colin Fraley dives deep into Rob’s entrepreneurial journey — from scaling in volatile markets to balancing profit with purpose.
Conversation Breakdown:
Rob’s early spark for entrepreneurship and lessons from multiple business exits
The evolution of commercial real estate and how AI is transforming the industry
What sustainable agriculture taught him about patience, resilience, and leadership
The story behind his bestselling books Beyond the Building and Hey, Dad…
His “Shut Up Moment” — the leap that changed everything
- Why legacy and impact drive his decisions more than ever before
Tune in to learn how Rob combines innovation, leadership, and sustainability to build a legacy that truly goes beyond the building.
🎙️ Sponsored by PeerFounder.com — the free-market crowdfunding platform empowering entrepreneurs to launch, fund, and grow their business on their own terms.
View all episodes
By Colin FraleyRob Finlay is a serial entrepreneur, investor, and bestselling author of Beyond the Building and Hey, Dad…, a life-advice book inspired by his journey as a father of four. Over the past 25+ years, he’s built and successfully exited four companies, pioneered debt optimization strategies in commercial real estate, and founded Thirty Capital and Defease With Ease, helping advise billions in transactions. Today, Rob’s focus spans AI, data analytics, leadership, and sustainable agriculture — proving that business success and long-term impact can go hand in hand.
In this episode of Startup or Shutup!, host Colin Fraley dives deep into Rob’s entrepreneurial journey — from scaling in volatile markets to balancing profit with purpose.
Conversation Breakdown:
Rob’s early spark for entrepreneurship and lessons from multiple business exits
The evolution of commercial real estate and how AI is transforming the industry
What sustainable agriculture taught him about patience, resilience, and leadership
The story behind his bestselling books Beyond the Building and Hey, Dad…
His “Shut Up Moment” — the leap that changed everything
- Why legacy and impact drive his decisions more than ever before
Tune in to learn how Rob combines innovation, leadership, and sustainability to build a legacy that truly goes beyond the building.
🎙️ Sponsored by PeerFounder.com — the free-market crowdfunding platform empowering entrepreneurs to launch, fund, and grow their business on their own terms.