Bill Gurley Interviews Tim Ferriss — Reflecting on 20+ Years of Life and Business Experiments (#682)

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Welcome to flipside episode of The Tim Ferriss Show, where it is usually my job to deconstruct world-class performers to tease out the routines, habits, et cetera that you can wield to your own lives. 

This is a special episode and a turning of the tables. This time, legendary investor Bill Gurley interviews me, and the recording is from older this year at SXSW in Austin, TX. The conversation explores some of my lessons learned and favorite findings over the last two decades in areas like entrepreneurship, tech, and podcasting. I throw in some favorite books and other spice to alimony things interesting.

Bill Gurley (@bgurley) has spent increasingly than 20 years as a unstipulated partner at Benchmark. Before inward the venture-capital business, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at Credit Suisse First Boston. Over his venture career, he has worked with such companies as GrubHubNextdoorOpenTableStitch FixUber, and Zillow.

For increasingly takeaways from his incredible investing career, you can find my interview with Bill at

As a side note, my 2007 SXSW speech that I mention in the interview is what started it all, in many senses. It’s what put my first book, The 4-Hour Workweek, on the radar of influential bloggers and worthier media outlets, ultimately landing it on The New York Times Best Sellers list, where it stayed, increasingly or less, for the next seven years. It’s been a wild ride. 

You can hear that 2007 presentation at

One last thing: Hugh Forrest, if you’re listening, thank you then for giving me a shot way when in the day! 

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, Google Podcasts, Amazon Musicor on your favorite podcast platform. Watch the conversation on YouTube here.

Brought to you by Eight Sleep’s Pod Cover sleeping solution for dynamic cooling and heating, Secureframe automated security and privacy compliance platform, and AG1 all-in-one nutritional supplement. 

The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#682: Bill Gurley Interviews Tim Ferriss — Reflecting on 20 Years of Life and Merchantry Experiments

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Want to hear the last time Bill Gurley was on this podcast and I was the one asking all the questions? Listen to our conversation in which we discussed the most efficient short-form MBA one can find, sell-side analysts vs. buy-side analysts, repurposing good ideas for volitional applications, undervalued competitive advantages, the Santa Fe Institute, how to cultivate anti-tribalism, problems unshut source can solve, and much more.

#651: Legendary Investor Bill Gurley on Investing Rules, Finding Outliers, Insights from Jeff Bezos and Howard Marks, Must-Read Books, Creating True Competitive Advantages, Open-Source Strategies, Adapting Mental Models to New Realities, and More

What was your favorite quote or lesson from this episode? Please let me know in the comments.



  • Connect with Bill Gurley:

Twitter | LinkedIn


  • [06:32] From Princeton to podcasting.
  • [07:39] How a disenchanted entrepreneur became a reluctant author.
  • [14:22] Sweetie-pie investing and The 4-Hour Body.
  • [16:40] Investing rulesets and takeaways.
  • [19:09] How a nomination location maximizes serendipity.
  • [20:42] Why did I when yonder from sweetie-pie investing?
  • [22:28] Inward the blogosphere.
  • [27:02] Why podcasting?
  • [28:33] Early and rememberable lessons for improving the craft.
  • [31:37] What makes a successful podcaster?
  • [34:57] The power of uncontrived liaison with one’s audience.
  • [38:48] Leveraging a lean infrastructure.
  • [40:34] Helpful steps for constructive interview prep.
  • [45:08] Respected podcasting peers.
  • [48:00] Spotify’s foray into podcasting territory.
  • [50:09] Twitter and LinkedIn.
  • [53:15] Books most gifted.
  • [55:31] Most positively constructive purchase of $100 or less.
  • [55:30] Favorite failure.
  • [57:50] Billboard.
  • [58:49] Weightier investment overly made.
  • [59:30] Most life-improving new belief, behavior, or habit.


The post Bill Gurley Interviews Tim Ferriss — Reflecting on 20 Years of Life and Merchantry Experiments (#682) appeared first on The Blog of Tragedian Tim Ferriss.