The Dart Board with Daniel Dart Bill Gurley | Benchmark – On finding your dream job, obsessive learning, and why passion beats the resume arms race
Bill Gurley, longtime Benchmark partner and author, shares his path from engineer to top venture capitalist. He explores obsessive learning, how to find and test a passion, and why going where the action is accelerates growth. He warns against the resume arms race, explains the value of reading and public writing, and discusses AI’s role in future-proofing careers.
50:40
Patterns Behind Elite Careers
- Bill Gurley noticed identical patterns across wildly different biographies and fields, revealing repeatable behaviors behind exceptional careers.
- He used his blogging practice to distill those patterns into teachable principles for career design.
Move To The Epicenter
- Go to where the action is and immerse yourself with the best learners and practitioners in your field.
- Co-learning at epicenters accelerates learning and creates more opportunities than staying isolated.
Judge Determination, Not Promises
- Ask whether someone will pursue an idea regardless of outside help to judge true commitment before investing or partnering.
- Look for founders who pursue learning obsessively because learning faster compounds advantage in a field.
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Intro
00:00 • 2min
Why Bill started studying elite performers
02:18 • 3min
From talk to book: nudges that mattered
05:19 • 2min
Why alternating stories and principles works
07:06 • 5min
The sixth principle: go where the action is
12:14 • 4min
Obsessive learning as a founder advantage
16:27 • 3min
Specialist vs generalist and career timing
19:26 • 1min
How to find your passion and test it
20:52 • 1min
Advice for parents: embrace exploration
22:15 • 4min
Danny Meyer and intentional career switches
25:50 • 1min
Bill's path: from engineer to venture capitalist
27:03 • 2min
Writing and building a public voice
29:05 • 2min
Serendipity and mentorship into VC
30:51 • 43sec
AI's role: learn the tool for your field
31:34 • 2min
Passion versus purpose and impact
33:16 • 3min
Best advice: make reading your superpower
35:53 • 2min
The power of admitting ignorance and listening
37:53 • 2min
Books that shaped Bill's thinking
39:55 • 3min
Bad advice: the college/resume pressure
42:40 • 2min
Value of an MBA when you lean into it
44:59 • 49sec
Turning failure into fuel
45:48 • 2min
Where Bill sees himself next
48:14 • 2min
Outro
50:04 • 31sec
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Meet Bill Gurley, longtime general partner at Benchmark and one of Silicon Valley’s most respected thinkers on markets, technology, and careers.
In this conversation, Bill reflects on his unconventional path into venture capital, the ideas behind his new book on finding and thriving in your dream job, and the patterns he’s observed across elite performers—from Bob Dylan to legendary coaches and founders. We talk about obsessive learning, building frameworks, going where the action is, and why doing what you love is the ultimate competitive advantage.
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