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

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. 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 GrubHub , Nextdoor , OpenTable , Stitch Fix , Uber , and Zillow . For more takeaways from his incredible investing career, you can find my interview with Bill at tim.blog/billgurley . 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 tim.blog/sxsw . One last thing: Hugh Forrest , if you’re listening, thank you again for giving me a shot way back in the day! Please enjoy! * This episode is brought to you by Secureframe ! Secureframe’s industry-leading compliance automation platform, paired with their in-house compliance experts and former auditors, helps you get audit-ready in weeks , not months, so you can close more deals faster. Secureframe simplifies and streamlines the process of getting and staying compliant to the most rigorous global privacy and security standards. They help thousands of businesses achieve compliance with security and privacy frameworks including SOC 2, ISO 27001, HIPAA, PCI, and GDPR . Schedule a demo today at Secureframe.com , and tell them during the demo that Tim Ferriss sent you to unlock 10% off for your first year. * This episode is also brought to you by AG1 ! I get asked all the time, “If you could use only one supplement, what would it be?” My answer is usually AG1 , my all-in-one nutritional insurance. I recommended it in The 4-Hour Body in 2010 and did not get paid to do so. I do my best with nutrient-dense meals, of course, but AG1 further covers my bases with vitamins, minerals, and whole-food-sourced micronutrients that support gut health and the immune system. Right now, you’ll get their Vitamin D Liquid Formula free with your first subscription purchase —a vital nutrient for a strong immune system and strong bones. Visit DrinkAG1.com/Tim to claim this special offer today and receive the free Vitamin D Liquid Formula (and 5 free AG1 travel packs) with your first subscription purchase! That’s up to a one-year supply of Vitamin D as added value when you try their delicious and comprehensive all-in-one daily greens product. * This episode is also brought to you by Eight Sleep ! Eight Sleep’s Pod Cover is the easiest and fastest way to sleep at the perfect temperature . It pairs dynamic cooling and heating with biometric tracking to offer the most advanced (and user-friendly) solution on the market. Simply add the Pod Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. It also splits your bed in half, so your partner can choose a totally different temperature. Go to EightSleep.com/Tim and save $250 on the Eight Sleep Pod Cover. Eight Sleep currently ships within the USA, Canada, the UK, select countries in the EU, and Australia. * [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. * For show notes and past guests on The Tim Ferriss Show , please visit tim.blog/podcast . For deals from sponsors of The Tim Ferriss Show , please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter ( 5-Bullet Friday ) at tim.blog/friday . For transcripts of episodes, go to tim.blog/transcripts . Discover Tim’s books: tim.blog/books . Follow Tim: Twitter : twitter.com/tferriss Instagram : instagram.com/timferriss YouTube : youtube.com/timferriss Facebook : facebook.com/timferriss LinkedIn: linkedin.com/in/timferriss Past guests on The Tim Ferriss Show include Jerry Seinfeld , Hugh Jackman , Dr. Jane Goodall , LeBron James , Kevin Hart , Doris Kearns Goodwin , Jamie Foxx , Matthew McConaughey , Esther Perel , Elizabeth Gilbert , Terry Crews , Sia , Yuval Noah Harari , Malcolm Gladwell , Madeleine Albright , Cheryl Strayed , Jim Collins , Mary Karr, Maria Popova , Sam Harris , Michael Phelps , Bob Iger , Edward Norton , Arnold Schwarzenegger , Neil Strauss , Ken Burns , Maria Sharapova , Marc Andreessen , Neil Gaiman , Neil de Grasse Tyson , Jocko Willink , Daniel Ek , Kelly Slater , Dr. Peter Attia , Seth Godin , Howard Marks , Dr. Brené Brown , Eric Schmidt , Michael Lewis , Joe Gebbia , Michael Pollan , Dr. Jordan Peterson , Vince Vaughn , Brian Koppelman , Ramit Sethi , Dax Shepard , Tony Robbins , Jim Dethmer , Dan Harris , Ray Dalio , Naval Ravikant , Vitalik Buterin , Elizabeth Lesser , Amanda Palmer , Katie Haun , Sir Richard Branson , Chuck Palahniuk , Arianna Huffington , Reid Hoffman , Bill Burr , Whitney Cummings , Rick Rubin , Dr. Vivek Murthy , Darren Aronofsky , Margaret Atwood , Mark Zuckerberg , Peter Thiel , Dr. Gabor Maté , Anne Lamott , Sarah Silverman , Dr. Andrew Huberman , and many more. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .