Letter to Bill Gurley
Legendary venture capitalist Bill Gurley published a book Runnin' Down a Dream: How to Thrive in a Career You Actually Love based on a talk by the same name he gave years ago.
Bill’s first principle is “find your passion.” But how did Bill actually find his? He didn’t have one passion. He had five fascinations pulling in different directions: technology, gambling, markets, writing, and wealth. Most people would pick one. Bill held all five, and kept assembling his career until they fit together.
Listen to the episode:
🎙️ Letter to Bill Gurley: Five Fascinations
Here’s the most revealing line I found, from his conversation with Tim Ferriss:
“I couldn’t discover something that got me excited. Slowly, I’ve come around to an idea that I made up. It’s not a career that other people have.”
He made it up. The career that made Bill Gurley one of the most successful venture capitalists in history didn’t exist before he assembled it from five separate fascinations. He didn’t find his passion. He built it.
The force that propelled Bill forward was boredom; not as distraction, but as data. Bill was “surprisingly bored” at one of the most exciting companies in tech. Most people would push through that feeling. Bill treated it as a signal that some of his fascinations weren’t being served.
In this letter:
- How growing up on a street of NASA scientists in Dickinson, Texas shaped how Bill learned to think
- The moment his sister's stock options at Compaq showed him a different kind of wealth
- Why Bill was "surprisingly bored" at one of the most exciting companies in tech
- The Palm Pilot move: how he spammed 350 of the most powerful people in tech with his newsletter
- Frank Quattrone's question that unlocked the final piece: "What is your dream job?"
- The 10:30 PM walk on the 36th floor of Park Avenue Plaza - and the question he asked himself
- Why boredom isn't ingratitude - it's data about which fascinations aren't being served
Listen:
If you want to find out whether this letter reaches Bill, and what happens if it does, follow Craftsmith wherever you listen to podcasts.
Talk soon,
Bill
P.S. Bill is @bgurley on X and on LinkedIn. If this resonated, send it his way.