Unconventional Startup Success

The speakers share their regrets about blindly following Silicon Valley conventions and missing opportunities by adhering to traditional startup thinking. They advocate for a more independent approach to business building, focusing on practical opportunities rather than chasing the next unicorn.

• Missed Opportunities Due to Conventional Thinking:

  • Failed to invest in successful companies like Calm ($2B+ company) and Loom ($1B company)
  • Passed on buying Stripe shares at $2B valuation (now worth ~100x more)
  • Overlooked investing in tools they were actually using (PagerDuty, Elasticsearch)

• Silicon Valley Narrative Limitations:

  • Pressure to be "laser focused" on one venture
  • Discouraged from investing in other startups
  • Push toward building billion-dollar companies instead of sustainable businesses
  • Emphasis on being a "product guy" building new markets

• Better Alternative Approaches:

  • Focus on communities and agency services
  • Build and experiment without obsessing over massive exits
  • Consider businesses with less market risk
  • Look for opportunities with "no product market fit risk"
  • Build newsletter businesses and other practical ventures

• Risk Assessment Strategy:

  • Differentiate between technical risk and market risk
  • Look for opportunities where market demand is guaranteed
  • Example: Robot pizza maker - engineering risk but no market risk
  • Focus on operational risk rather than market risk

• Key Lessons:

  • Don't blindly follow VC narratives
  • Better lifestyle possible without chasing unicorn status
  • Look for opportunities right under your nose
  • Question what obvious opportunities you might be missing today