Invest Like the Best with Patrick O'Shaughnessy

Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]

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Feb 28, 2025
Doug Leone, former leader of Sequoia Capital, shares invaluable insights from over 25 years in venture capital. He emphasizes the importance of clarity in decision-making and balancing tough leadership with compassion. Leone discusses common pitfalls in investing, particularly the need to focus on business fundamentals over mere technology trends. He reflects on building competitive advantage, the significance of resilience in the face of market downturns, and the power of simplicity in investment opportunities, leaving listeners with lessons on kindness and integrity.
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ANECDOTE

Don Valentine's Heart

  • Don Valentine, Sequoia's founder, was initially perceived as purely business-driven by Doug Leone.
  • Later, Leone learned about Valentine's softer side through his children's eulogy.
ANECDOTE

Tough Feedback

  • Don Valentine left Doug Leone a note saying, "Doug, not fit to listen to founders."
  • This direct feedback, though harsh, pushed Leone to reflect and improve.
INSIGHT

Transformation

  • Doug Leone's interviewing style evolved from "insufferable" to "charming" over time.
  • He acknowledges this change as a "Marcom transformation."
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