Tim Guleri has had a remarkable run at Sierra Ventures since 2001. He has invested in transcendent companies including Sourcefire and MakeMyTrip which both went public. Before that, Tim had a successful career as an entrepreneur and exec at companies like Scopus and Octane which was acquired by Epiphany in 2000.

Sierra has one of the strongest future of work and AI portfolios that includes companies like Paro, Krisp, and SupportLogic which acquired Emtropy Labs which was founded by great former guest Harish Batlapenamurthy. In full disclosure, Sierra and I are both investors in ArmorCode.

Listen and learn…

  1. Why the most successful venture investors were previously entrepreneurs
  2. Tim's thesis for investing in gen AI customer journey company Simulate
  3. How Tim identifies "gen AI whitewashing" when hearing pitches
  4. Why gen AI is more than just another platform shift
  5. How gen AI startups can beat Big Tech incumbents
  6. Why all companies are ultimately "financial products"
  7. Sierra's primary data from CIOs: "…they're spending money on use cases that unlock employee productivity"
  8. What Tim means by "build horizontally but execute vertically"
  9. Which jobs AI will eliminate vs. augment
  10. Tim's "one that got away" pitch from his early days at Sierra

References in this episode…