Episodes

  • AI Risks Small Businesses Overlook: How to Avoid Costly Mistakes

    AI Risks Small Businesses Overlook: How to Avoid Costly Mistakes
    Oct 14 2026
    In this insightful interview, Paul Graham and David Robinson explore the critical risks and strategic considerations for small and mid-sized businesses adopting AI technology. They discuss how to identify real problems versus symptoms, the importance o...
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    31 mins
  • Unlocking $22.1m in Stalled Pipeline

    Unlocking $22.1m in Stalled Pipeline
    Oct 1 2026
    In this episode, Jen Kelly shares how a company unlocked $22 million in pipeline by refining lead nurturing and sales strategies. Paul Graham discusses growth mindset, customer diversification, and effective marketing tactics for business success.Timel...
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    34 mins
  • Why Doing Everything Yourself Cost $100 Million

    Why Doing Everything Yourself Cost $100 Million
    Sep 22 2026
    Larry G. Dix II shares his transformative journey of self-awareness, the importance of delegation, accountability, and living intentionally to maximize success and fulfillment in business and life. Timeline 00:00 Introduction and the importance of self...
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    52 mins
  • The Power of Fractional CFOs in Scaling Your Business

    The Power of Fractional CFOs in Scaling Your Business
    Sep 16 2026
    In this episode, Paul Graham and Richard Boyd discuss the critical role of financial management and fractional CFOs in scaling businesses from five to thirty million dollars. They explore real-world stories, misconceptions about CFOs, and how AI is tra...
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    39 mins
  • The End of Manual Capital Raising

    The End of Manual Capital Raising
    Sep 10 2026
    In this episode, Paul sits down with Elisabeth Bykoff ex-PwC, 10-year venture veteran, and founder of Boxsy, to break down why most founders start the fundraising process completely wrong, whether you actually need to raise at all, and how an AI COO pl...
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    32 mins
  • Before You Build a Family Office, Fix This First

    Before You Build a Family Office, Fix This First
    Aug 6 2026
    JD Rockefeller invented the family office in 1882 because every advisor he had was working in a silo and nobody was talking to each other. Most business owners today have the exact same problem. Dale Montgomery oversees a virtual family office with 70+...
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    25 mins
  • The Hidden Cost of Not Tracking Your Digital Assets

    The Hidden Cost of Not Tracking Your Digital Assets
    Aug 6 2026
    An advisor came to Perry Woodin and said his client had 50 crypto wallets. When they looked closer, they found 150. With dozens of digital assets across them that the client didn't even know existed. Perry Woodin is the co-founder of Node40, a digital ...
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    26 mins
  • How To Add AI To Your Business Without Breaking Everything That Already Works

    How To Add AI To Your Business Without Breaking Everything That Already Works
    Jul 20 2026
    It's not a magic robot. It's an LLM call on a while loop. Mike Vanamburg has built AI agents for companies across industries — from cannabis dispensaries to bookkeeping firms to his own business — and the lesson he keeps learning is the same every time...
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    35 mins