What do you do when the world starts changing faster than your ability to make sense of it?
Do you hold tighter to what you know… or do you learn how to evolve, let go, and redefine who you are?
In this episode, I sit down with legendary investor and True Ventures partner Tony Conrad, a man who has helped shape some of the most influential companies of the past two decades — and who is now in the most reflective stage of his life and career.
We talk about the quiet side of leadership, the inner work required to stay relevant, why the AI revolution is forcing everyone to rethink their value, and how a surreal moment in a deportation jail in India woke him up to the fragility of everything we take for granted.
Timestamps:
00:00 — Who is Tony Conrad? Identity beyond job titles
02:00 — Building True Ventures & the early days nobody saw
05:00 — The J-curve years: failure, doubt, and patience
08:00 — AI: the biggest shift of Tony’s lifetime
10:00 — How True Ventures stays mentally fit as a team
12:00 — Culture > ego: why they avoid the Midas List
14:00 — Travel, awareness & seeing the world clearly again
17:00 — The India deportation jail story
20:00 — Japan, America & the truth about cultural contrast
22:00 — Why Tony stayed in San Francisco through every cycle
25:00 — Reinventing his role: from “points on the board” to empowering others
27:00 — Being public vs staying private: how the VC world has changed
30:00 — The ancient teachers question & who Tony would speak to
33:00 — Shackleton, survival & the greatest leadership example he knows
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A special thanks to our mental fitness + sweat partner Sip Saunas.
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Special props 👇
Music: Clouds - Joakim Karud
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