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.

🧠 x 🥵 = 😃

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Special props 👇

Music: Clouds - Joakim Karud

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