Pre-IPO Share Strategy

The speaker discusses a missed opportunity strategy around buying secondary shares in proven startups pre-IPO, using Stripe as the key example. The strategy focuses on identifying already-successful companies and buying shares before they go public.

Key Points:

• Target Proven Companies:

  • Look for clearly successful startups (like Stripe at $2B valuation)
  • Focus on companies that are already "the best startup" in their space
  • Don't worry about being "too late" - there's still massive upside

• Investment Strategy:

  • Buy secondary shares from existing shareholders
  • Look for companies you're already using in your tech stack
  • Examples of successful targets:
    • Stripe
    • PagerDuty
    • Elasticsearch

• Validation Methods:

  • Invest in products you're actively using and paying for
  • Look at your company's P&L/expenses to identify potential investments
  • Focus on companies that are proven but pre-IPO

• Returns Example:

  • Stripe shares at $2B valuation would have returned ~100x
  • Focus on proven winners rather than trying to get in at the earliest stages

The strategy emphasizes investing in clear winners even at what seems like "late" stages, rather than trying to find the earliest-stage opportunities.