Singles Over Home Runs

A look at how successful investors like Egan Durbin (Silver Lake) and others approach investing with a focus on consistent, optimized returns rather than swinging for home runs.

Core Investment Philosophy

• Focus on hitting "singles and doubles" rather than home runs
• After base hits, aggressively optimize through operations ("steal third")
• Look for 1-2 major investment opportunities per year
• Push all chips in when finding the right opportunity
• Aim to be the best risk-adjusted tech investor globally

Key Investment Principles

• Concentration over diversification

  • Make few, large concentrated bets
  • Look for "can't say no to" opportunities
  • Willing to wait for right opportunities

• Operational Improvement

  • Active involvement in portfolio companies
  • Focus on operational excellence after investment
  • Use expertise to improve company performance
  • Example: Skype turnaround
    • Settled lawsuits
    • Hired strong CEO
    • Invested in product improvement
    • Sold for $8.5B after buying for $1.9B

• Market Timing

  • Willing to stay out of market when overvalued
  • Patient capital - can wait for right valuations
  • Example: Stayed away from late-stage tech in 2021
  • Predicted unicorn valuations would crash

• Deal Structure

  • Creative deal structuring
  • Example: Airbnb investment during pandemic
    • $1B investment when company struggled
  • Structured deals with warrants/debt components
  • Focus on downside protection

Personal Characteristics

• Aggressive but calculated approach
• High conviction when opportunities arise
• Willing to be contrarian
• Focus on long-term value creation
• Strong operational understanding
• Patient but aggressive when committed