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

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Welcome to another 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 apply 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 earlier 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 keep things interesting.

Bill Gurley (@bgurley) has spent more than 20 years as a general partner at Benchmark. Before entering 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 more 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 bigger media outlets, ultimately landing it on The New York Times Best Sellers list, where it stayed, more 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 again for giving me a shot way back 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 Business 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 alternative applications, undervalued competitive advantages, the Santa Fe Institute, how to cultivate anti-tribalism, problems open 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] Angel investing and The 4-Hour Body.
  • [16:40] Investing rulesets and takeaways.
  • [19:09] How a choice location maximizes serendipity.
  • [20:42] Why did I back away from angel investing?
  • [22:28] Entering the blogosphere.
  • [27:02] Why podcasting?
  • [28:33] Early and enduring lessons for improving the craft.
  • [31:37] What makes a successful podcaster?
  • [34:57] The power of direct communication with one’s audience.
  • [38:48] Leveraging a lean infrastructure.
  • [40:34] Helpful steps for effective 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 effective purchase of $100 or less.
  • [55:30] Favorite failure.
  • [57:50] Billboard.
  • [58:49] Best investment ever made.
  • [59:30] Most life-improving new belief, behavior, or habit.


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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

  1. Tim this one was GOLD. I’ve heard a ton of your interviews and there were some unheard gems y’all dug up here. Requesting these more often, porfa x)

  2. Tim – Hi! Great interview. I love hearing people’s origin stories!

    ‘m a self-published author who has sold 10 million copies of my books so far. I’m now repeating this success in 4 other languages. I love your podcast and I was thinking it might be super helpful for female-and male-entrepreneurs to hear how I got here and how they can do it too.

  3. Potential Guest. Having listened to this episode and hearing how Tim selects his guests, I would like to suggest International Health and Well-being Expert Jessie Pavelka; Trainer on the Biggest Loser USA, Sky TV presenter ‘Obese: A Year to Save my Life’ and author of ‘The Program’ – and my business partner.

    I’d be happy to send through a synopsis of why we feel he would fit the criteria for Tim’s show. His life experiences through childhood, early life and finding his way to where he is now, carries some powerful messages around health and mindset, that the world needs to hear, and, he lives just outside Austin.

    Thanks Team Tim!