Invest Like the Best with Patrick O'Shaughnessy

Doug Leone - Lessons from a Titan - [Invest Like the Best, EP.318]

857 snips
Feb 28, 2023
Doug Leone, former leader of Sequoia Capital, shares his journey of transforming a small fund into an $85 billion powerhouse. He reflects on overcoming early hardships, the importance of simplicity in investment strategies, and balancing toughness with care in leadership. Leone discusses navigating the venture capital landscape, recognizing talent, and common pitfalls investors face. His insights emphasize adaptability in a changing market and the value of transparent communication in building trust with investors.
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ANECDOTE

Don Valentine's Two Sides

  • Doug Leone initially perceived Don Valentine as purely business-driven, prioritizing returns for their clients.
  • Later, he learned about Valentine's softer side at home, a contrast to his tough work persona.
ANECDOTE

Tough Feedback and Hidden Support

  • Don Valentine left Doug Leone a harsh note, bluntly assessing his ability to interact with founders.
  • Despite the tough feedback, Valentine also saw potential in Leone, advocating for him when others wanted him out.
ADVICE

Identifying Outlier Qualities

  • Look for outlier qualities in founders and investors: extreme drive, unique motivations, and a willingness to take risks.
  • Understand their motivations by repeatedly asking "why" to uncover their true drive and ensure it's channeled positively.
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