Invest Like the Best with Patrick O'Shaughnessy

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

257 snips
Dec 26, 2023
Doug Leone, former Sequoia Capital partner, shares wisdom from his 25+ years in venture capital. He discusses the importance of keeping investment strategies simple and transparent, offering insights on go-to-market motions and trust-building with founders. Leone reflects on his evolution from leader to mentor, emphasizing resilience and the value of genuine relationships in navigating the ever-changing investment landscape. He also highlights the critical choices between venture capital and entrepreneurship, advocating for alignment with one's strengths and passions.
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ANECDOTE

Early struggles and mentorship

  • Doug Leone initially struggled at Sequoia, receiving a note from Don Valentine that said, "Not fit to listen to founders."
  • Valentine's toughness, while harsh, pushed Leone to reflect and improve, demonstrating a unique mentorship style.
INSIGHT

Transformation and Perception

  • Doug Leone's transformation from "insufferable" to "charming" highlights the impact of experience and track record.
  • Maturity and wisdom, gained over time, can significantly alter how one is perceived and how one interacts with others.
ADVICE

Understanding Motivation

  • Understand people's core motivations by asking "why" repeatedly.
  • Look for outlier traits like drive and resilience, even if perceived negatively by others, as they can indicate potential for success.
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