Three-Part Investment Filter

A successful investment strategy shared by experienced entrepreneurs focusing on overlooked opportunities and reducing market risk.

Core Investment Principles

• Invest in smart people you know personally

  • Look for opportunities within your network
  • If you lack capital, raise money to invest in smart friends
  • Example: Missed opportunity with Calm founders ($2B+ company now)

• Invest in products/services you use

  • Look at your company's P&L expenses
  • Invest in the tools and services you're already paying for
  • Examples: PagerDuty, Elasticsearch, Stripe (missed opportunity at $2B valuation)

• Don't wait for VC validation

  • VCs often identify opportunities 3-4 years late
  • Look for niche opportunities that seem small initially
  • Focus on current problems and opportunities, not past successes

Risk Management Strategy

• Reduce market risk

  • Look for opportunities with proven market demand
  • Example: Pizza-making robot
    • High engineering risk but zero market risk
    • Clear value proposition: perfect pizza, 24/7, lower cost than humans

• Avoid common startup traps

  • Don't feel pressured to build "billion-dollar companies"
  • Focus on niches and community building
  • Consider agency services and smaller experiments
  • Avoid "playing by Silicon Valley rules"

Key Mindset Shifts

• Question conventional wisdom

  • Challenge the "laser focus" mentality
  • Be open to multiple revenue streams
  • Look for opportunities others dismiss as "too niche"

• Stay alert to opportunities

  • Many opportunities are "right under your nose"
  • What seems small today might be huge tomorrow
  • Don't dismiss opportunities because they seem "late"