The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified 501. Spotting the Next Big Thing, Why This Cycle Is Different, Acceptable vs Unacceptable Risk, and Why Duration Is a Feature Not a Bug (Jon Callaghan)
Feb 2, 2026
Jon Callaghan, managing partner at True Ventures with two decades of early-stage investing and hits like Fitbit and HashiCorp, talks curiosity-driven sourcing and spotting nascent markets. He discusses why long duration is a feature, how to balance acceptable versus unacceptable risks, the value of repeat founders and referrals, and what makes this AI cycle different. Short, thoughtful, and contrarian perspectives on early-stage venture.
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Early Market Bet That Taught Everything
- Jon Callaghan started a mountain bike shop at 17 after a bike shop owner dismissed the sport as irrelevant.
- That early bet taught him every operational lesson and framed his taste for spotting nascent markets.
Curiosity Is The Primary Edge
- Successful early-stage investing depends on a learner's mind and relentless curiosity, not just charisma.
- Treat every conversation as deep inquiry to discover possibilities and founder talent.
Venture Is A 5% Game
- Venture returns come from a small fraction of hits; Callaghan estimates roughly 5% are true fund-makers.
- Accept being wrong most of the time and focus resources on the few companies with breakout potential.
