Craftsmith

·E3

Letter to Bill Gurley: Five Fascinations

March 9
23 mins

Episode Description

"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:


Source conversations referenced in this letter:


Help deliver this letter:
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Craftsmith is a podcast by Bill Allred about people doing work they love, so you can too.

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