Modern Wisdom · 2026-03-14 · 117 min · 20,958 words

If You Hate Your Job, This is How to Start Over - Bill Gurley - #1071

Listen to the original audio · Transcribed with NVIDIA Parakeet · Timestamps stay in sync with the live audio

What got you into thinking about the idea of career regret as somebody that's had a very seemingly successful and fun career? Why did you think about it? I um I used to I so I spent 25 years as a venture capitalist and the four years before that as a self-side analyst on Wall Street. And through that process, I started writing as a way to differentiate myself. And so I was a

early blogger. It was actually a fax. That's how old I am. Um when I started. And I got in the habit of when I had ideas, jotting them down.

And then, you know, either developing them. A lot of them ended up just undeveloped, but I would if I developed them, they would become a blog post. And there was a period in my career where I was reading a ton of biographies. And I finished this third one and saw a through line with these other two from people that were in wildly different fields. And I jotted those notes down.

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