"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." - Bill Gurley to Tim Ferriss

Bill Gurley'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. A love affair with technology, a gambling bug, a deep curiosity about markets, a need to write, and a desire for wealth. Most people would pick one. Bill held all five, with no idea how they'd fit together - and kept building until they did.

This is a Craftsmith Letter, an audio letter to a living craftsperson.

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 changed everything: "What is your dream job?"
The 10:30 PM walk on the 36th floor of Park Avenue Plaza - and the question he asked himself
What Bill told Tim Ferriss that reveals the pattern of his entire career: "I made it up. It's not a career that other people have."
Why boredom isn't ingratitude - it's data about which fascinations aren't being served

Chapters:

(00:00) - Why This Letter
(00:28) - Bill Gurley’s Big Idea
(01:21) - Five Fascinations
(02:31) - NASA Roots in Texas
(03:48) - Sister’s Compaq Spark
(05:07) - Gambling Bug Awakens
(06:06) - Writing as Thinking
(07:47) - Bored at Compaq
(09:23) - MBA and VC Dream
(10:19) - Wall Street Detour
(11:34) - Palm Pilot Power Move
(12:54) - Silicon Valley Breakthrough
(13:15) - Boredom Returns Again
(14:21) - Finally Venture Capital
(16:46) - Permission to Fail
(17:28) - Post-Benchmark Restlessness
(18:34) - Make It Up Again
(19:45) - Lessons on Boredom
(20:56) - The Book Needed Permission
(21:57) - Invitation and Next Steps
(22:07) - Weekly Exercise and Share

References:

Runnin' Down a Dream by Bill Gurley
Bill Gurley's UT Austin talk - the original "Runnin' Down a Dream" speech
Above the Crowd - Bill's blog

Source conversations referenced in this letter:

Bill Gurley on Tetragrammaton with Rick Rubin - where Bill discusses permission and disinhibition
Bill Gurley on The Tim Ferriss Show #840 - where Bill reveals "I made it up"

Help deliver this letter:
If you think Bill should hear this, send him this episode:

@bgurley on X
Bill Gurley on LinkedIn

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Craftsmith is a podcast by Bill Allred about people doing work they love, so you can too.