Invest Like the Best with Patrick O'Shaughnessy

Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, EP.181]

145 snips
Jul 7, 2020
Charlie Songhurst, former head of strategy at Microsoft and an investor in nearly 500 companies, shares his unique insights on success in business. He discusses the motivations behind power, money, and fame, emphasizing how these influences shape decision-making in startups. Charlie explores essential traits in founders and the importance of early hires. He also highlights the value of diverse perspectives in investing and how mentorship contributes to navigating the complexities of investing.
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ADVICE

Stack Rank Vices and Motivators

  • Stack rank vices (power, money, fame) and motivators (impact, intellectual interest, people).
  • This reveals good-fit answers for founders/hires and helps understand organizational success.
INSIGHT

Founder-Market Fit

  • There's no single ideal entrepreneur; founder-market fit is key.
  • Consumer founders need empathy, while enterprise founders need rationality.
INSIGHT

Stages of Startup Failure

  • Startup failure often stems from predictable issues at each stage.
  • These include team dynamics (pre-seed), product-market fit (seed), scaling management (Series A), and institution building (Series B+).
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