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

Brought to you by Eight Sleep’s Pod Cover https://eightsleep.com/Tim sleeping solution for dynamic cooling and heating, Secureframe https://secureframe.com/?utm_source=partner&utm_medium=podcast&utm_campaign=TimFerriss automated security and privacy compliance platform, and AG1 https://drinkag1.com/tim all-in-one nutritional supplement. Welcome to another episode of The Tim Ferriss Show http://tim.blog/podcast, 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 https://twitter.com/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 http://www.grubhub.com/, Nextdoor https://nextdoor.com/, OpenTable http://www.opentable.com/san-francisco-restaurants, Stitch Fix http://www.stitchfix.com/, Uber https://www.uber.com/, and Zillow http://www.zillow.com/. For more takeaways from his incredible investing career, you can find my interview with Bill at tim.blog/billgurley https://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 https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357/?tag=offsitoftimfe-20, 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 http://tim.blog/sxsw. One last thing: Hugh Forrest https://twitter.com/hugh_w_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 https://secureframe.com/?utm_source=partner&utm_medium=podcast&utm_campaign=TimFerriss! 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 https://secureframe.com/?utm_source=partner&utm_medium=podcast&utm_campaign=TimFerriss 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 https://secureframe.com/?utm_source=partner&utm_medium=podcast&utm_campaign=TimFerriss, 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 https://drinkag1.com/tim! I get asked all the time, “If you could use only one supplement, what would it be?” My answer is usually AG1 https://drinkag1.com/tim, 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 https://drinkag1.com/tim 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 https://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 http://eightsleep.com/Tim! Eight Sleep’s Pod Cover http://eightsleep.com/Tim 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 http://eightsleep.com/Tim 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 http://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 https://tim.blog/podcast, please visit tim.blog/podcast https://tim.blog/podcast/?utm_source=podcast&utm_medium=podcast&utm_campaign=podcast-description. For deals from sponsors of The Tim Ferriss Show https://tim.blog/podcast, please visit tim.blog/podcast-sponsors https://tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday https://go.tim.blog/5-bullet-friday-1/. For transcripts of episodes, go to tim.blog/transcripts https://tim.blog/transcripts. Discover Tim’s books: tim.blog/books https://tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss https://twitter.com/tferriss Instagram: instagram.com/timferriss https://instagram.com/timferriss/ YouTube: youtube.com/timferriss https://www.youtube.com/timferriss Facebook: facebook.com/timferriss https://www.facebook.com/TimFerriss/ LinkedIn: linkedin.com/in/timferriss http://linkedin.com/in/timferriss Past guests on The Tim Ferriss Show http://tim.blog/podcast include Jerry Seinfeld https://tim.blog/2020/12/08/jerry-seinfeld/, Hugh Jackman https://tim.blog/2020/06/26/hugh-jackman/, Dr. Jane Goodall https://tim.blog/2020/04/16/jane-goodall/, LeBron James https://tim.blog/2018/11/27/lebron-james-mike-mancias/, Kevin Hart https://tim.blog/2020/05/20/kevin-hart/, Doris Kearns Goodwin https://tim.blog/2018/09/07/doris-kearns-goodwin-leadership/, Jamie Foxx https://tim.blog/2015/12/06/jamie-foxx/, Matthew McConaughey https://tim.blog/2020/10/19/matthew-mcconaughey/, Esther Perel https://tim.blog/2017/05/21/esther-perel/, Elizabeth Gilbert https://tim.blog/2020/05/08/elizabeth-gilbert/, Terry Crews https://tim.blog/2017/12/20/terry-crews-how-to-have-do-and-be-all-you-want/, Sia https://tim.blog/2020/08/12/sia/, Yuval Noah Harari https://tim.blog/2020/10/27/yuval-noah-harari/, Malcolm Gladwell https://tim.blog/2016/06/21/malcolm-gladwell/, Madeleine Albright https://tim.blog/2020/05/27/secretary-madeleine-albright/, Cheryl Strayed https://tim.blog/2017/03/30/cheryl-strayed/, Jim Collins https://tim.blog/2019/02/18/jim-collins/, Mary Karr, https://tim.blog/2020/11/11/mary-karr/ Maria Popova https://tim.blog/2014/10/21/brain-pickings/, Sam Harris https://tim.blog/2020/05/15/sam-harris-2/, Michael Phelps https://tim.blog/2021/01/21/michael-phelps-grant-hackett/, Bob Iger https://tim.blog/2020/01/16/bob-iger/, Edward Norton https://tim.blog/2019/10/31/edward-norton-motherless-brooklyn/, Arnold Schwarzenegger https://tim.blog/2015/02/02/arnold-schwarzenegger/, Neil Strauss https://tim.blog/2014/06/24/neil-strauss/, Ken Burns https://tim.blog/2019/09/12/ken-burns/, Maria Sharapova https://tim.blog/2017/08/26/maria-sharapova/, Marc Andreessen https://tim.blog/2016/05/29/marc-andreessen/, Neil Gaiman https://tim.blog/2019/03/28/neil-gaiman/, Neil de Grasse Tyson https://tim.blog/2019/10/03/neil-degrasse-tyson/, Jocko Willink https://tim.blog/2016/09/21/jocko-willink-on-discipline-leadership-and-overcoming-doubt/, Daniel Ek https://tim.blog/2020/12/03/daniel-ek/, Kelly Slater https://tim.blog/2020/09/08/kelly-slater/, Dr. Peter Attia https://tim.blog/2019/11/27/peter-attia-fasting-metformin-longevity/, Seth Godin https://tim.blog/2016/02/10/seth-godin/, Howard Marks https://tim.blog/2018/09/25/howard-marks/, Dr. Brené Brown https://tim.blog/2020/02/06/brene-brown-striving-self-acceptance-saving-marriages/, Eric Schmidt https://tim.blog/2019/04/09/eric-schmidt/, Michael Lewis https://tim.blog/2020/05/01/michael-lewis/, Joe Gebbia https://tim.blog/2018/03/08/joe-gebbia-co-founder-of-airbnb/, Michael Pollan https://tim.blog/2018/05/06/michael-pollan-how-to-change-your-mind/, Dr. Jordan Peterson https://tim.blog/2021/03/01/jordan-peterson/, Vince Vaughn https://tim.blog/2017/05/31/vince-vaughn/, Brian Koppelman https://tim.blog/2020/04/23/brian-koppelman/, Ramit Sethi https://tim.blog/2019/05/07/ramit-sethi/, Dax Shepard https://tim.blog/2020/11/18/dax-shepard/, Tony Robbins https://tim.blog/2014/10/15/money-master-the-game/, Jim Dethmer https://tim.blog/2020/05/18/jim-dethmer/, Dan Harris https://tim.blog/2020/11/19/dan-harris/, Ray Dalio https://tim.blog/2017/09/13/ray-dalio/, Naval Ravikant https://tim.blog/2015/08/18/the-evolutionary-angel-naval-ravikant/, Vitalik Buterin https://tim.blog/2021/03/08/vitalik-buterin-naval-ravikant/, Elizabeth Lesser https://tim.blog/2021/03/16/elizabeth-lesser/, Amanda Palmer https://tim.blog/2019/04/18/amanda-palmer-2/, Katie Haun https://tim.blog/2021/02/18/katie-haun/, Sir Richard Branson https://tim.blog/2017/10/09/richard-branson/, Chuck Palahniuk https://tim.blog/2020/09/02/chuck-palahniuk/, Arianna Huffington https://tim.blog/2017/10/18/arianna-huffington/, Reid Hoffman https://tim.blog/2015/08/31/the-oracle-of-silicon-valley-reid-hoffman-plus-michael-mccullough/, Bill Burr https://tim.blog/2017/09/17/bill-burr/, Whitney Cummings https://tim.blog/2015/06/26/whitney-cummings/, Rick Rubin https://tim.blog/2015/05/15/rick-rubin/, Dr. Vivek Murthy https://tim.blog/2020/03/26/vivek-murthy/, Darren Aronofsky https://tim.blog/2017/09/09/darren-aronofsky/, Margaret Atwood https://tim.blog/2022/02/22/margaret-atwood/, Mark Zuckerberg https://tim.blog/2022/03/24/mark-zuckerberg/, Peter Thiel https://tim.blog/2014/09/09/peter-thiel/, Dr. Gabor Maté https://tim.blog/2018/02/20/gabor-mate/, Anne Lamott https://tim.blog/2021/07/09/anne-lamott/, Sarah Silverman https://tim.blog/2022/01/12/sarah-silverman/, Dr. Andrew Huberman https://tim.blog/2021/07/06/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.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Tim Ferriss?

  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 to get audit-ready in weeks, not months, so you can close more deals faster. I polled a ton of you online on social and reviews came back, which were overwhelmingly positive for SecureFrame. 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. SecureFrame is the most comprehensive security and compliance automation platform with hundreds of integrations,

• 0:44Tim Ferriss?

  built-in security training, vendor and risk management, and more. You continuously detect and remediate misconfigurations across your technology stack. You also get complete visibility with actionable insights on critical security and privacy compliance issues. Security training for SOC 2, HIPAA, PCI, DSS, GDPR, and more are built into SecureFrame's platform. You can quickly meet security and privacy compliance requirements and save time signing, tracking, and reporting on required training. SecureFrame provides unmatched expert guidance every step of the way with their 30-plus former auditors and industry professionals. SecureFrame helps you quickly achieve and maintain compliance so you can focus on other things, like serving your customers, scaling your business, and growing revenue. So, consider automating your security

• 1:29Tim Ferriss?

  and privacy compliance with SecureFrame. Schedule a demo today at SecureFrame.com, as it sounds, SecureFrame.com, and tell them Tim Ferriss, that's me. Tim Ferriss sent you to unlock 10% off for your first year. Again, that's SecureFrame.com. And during your demo, tell them that Tim Ferriss sent you to unlock 10% off for your first year. One more time, SecureFrame.com.

• 1:55Tim Ferriss?

  This episode is brought to you by Eight Sleep. Temperature is one of the main causes of poor sleep and heat is my personal nemesis. I've suffered for decades tossing and turning, throwing blankets off, pulling the back on, putting one leg on top and repeating all of that ad nauseam. But now I am falling asleep in record time. Why? Because I'm using a device that was recommended to me by friends called the Pod Cover by Eight Sleep. The Pod Cover fits on any mattress and allows you to adjust the temperature of your sleeping environment, providing the optimal temperature that gets you the best night's sleep. With the Pod Cover's dual-zone temperature control, you and your partner can set your sides of the bed to as cool as 55 degrees or as hot as 110 degrees.

• 2:36Tim Ferriss?

  I think generally in my experience, my partners prefer the high side and I like to sleep very, very cool. So stop fighting, this helps. Based on your biometrics, environment and sleep stages, the Pod Cover makes temperature adjustments throughout the night that limit wake-ups and increase your percentage of deep sleep. In addition to its best-in-class temperature regulation, the Pod Cover sensors also track your health and sleep metrics without the need to use a wearable. So go to eightsleep.com/tim, all spelled out, eightsleep.com/tim and save $250 on the Eight Sleep Pod Cover. That's eightsleep.com/tim. Eight Sleep currently ships within the US, Canada and the UK, select countries in the EU and Australia.

• 3:18Tim Ferriss?

  Again, that's eightsleep.com/tim to save $250 on the Eight Sleep Pod Cover.

• 3:24Speaker 01

  At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question?

• 3:31Tim Ferriss?

  No, we're just in an appropriate time.

• 3:35Speaker 02

  I'm a cybernetic organism living tissue over metal endoskeleton.

• 3:47Tim Ferriss?

  Hello, boys and girls, ladies and germs. Welcome to another episode of The Tim Ferriss Show, where it is usually my job to deconstruct world-class performers of all different types 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 around, legendary investor Bill Gurley interviews me, and the recording is from earlier this year at South by Southwest in Austin, Texas. The conversation explores some of my lessons learned and favorite findings over the last two decades or so in areas like entrepreneurship, tech, and podcasting, just to name three. I also throw in some favorite books and other spicy bits to keep things interesting. Let me mention a bit more about Bill before we get started. Bill Gurley,

• 4:32Tim Ferriss?

  you can find him on Twitter @B Gurley, G U R L E Y, 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 incredibly impressive venture career, he has worked with such companies as Grubhub, Nextdoor, OpenTable, Stitch Fix, Uber, and Zillow, just to name a few. For more takeaways from his incredible investing career, you can find my interview with Bill, that's me interviewing Bill, at tim.blog/BilGurley. And as a side note, my 2007 South by Southwest keynote,

• 5:13Tim Ferriss?

  this was a speech, my first appearance at South by, that I mention in this conversation with Bill, was what started it all, in many senses. It's what put my first book, The Four Hour Work Week, on the radar of influential bloggers and bigger media outlets, ultimately landing the book on the New York Times Bestseller List, where it stayed more or less unbroken for the next seven years. It's been a wild ride, and this segment, this brief appearance at South by, is what kicked it all off. And if you would like to hear that 2007 presentation, you can find it at tim.blog/SXSW, which is the abbreviation for South by Southwest. So one more time, that's tim.

• 5:55Tim Ferriss?

  blog slash SXSW and my voice sounds hilariously different. My presentation skills hilariously less refined than they are today. Not to say they're perfect, but things have changed and we get better day by day, little by little. And one last thing, Hugh Forrest, if you are listening, thank you again for giving me a shot way back in the day. It made a difference and that is why I come back to South by just about every year. And without further ado, please enjoy a wide ranging conversation with Bill Gurley.

• 6:33Bill Gurley?

  Well, it's great to be here. It's awesome to have the opportunity to turn the tables on Tim and interview. I was just recently on Tim's podcast and so I actually suggested this before that so that it would keep him honest when we were going earlier. Tim, a lot of you, I assume all know who he is. He's one of the most celebrated and decorated and successful digital creators of our time. He sold 10 million books. I got a list here. He's got 2 million email subs, over 1,000 blog posts, 7 million followers on social media and his podcast is about to pass a billion downloads. And so since South by, you know, is a lot about interactive and, and how people can

• 7:17Bill Gurley?

  be successful in these types of fields. I thought it'd be great to see if we could dive deep and find out how he got here and what some of his core tenants are for being successful. So you graduated from Princeton in the year 2000 with the East Asian Studies major. Is that correct?

• 7:35Tim Ferriss?

  That's right. Yeah. Perfect setup for podcasting.

• 7:37Bill Gurley?

  Yeah. And in 2014, you launched your podcast.

• 7:42Tim Ferriss?

  Right.

• 7:42Bill Gurley?

  Okay. So 14 years, just tell us quickly what happened in those 14 years and how you found your way there. And I'm very curious about lessons learned and when it became intentional. Like, when did you know you were doing something versus just experiencing it?

• 8:01Tim Ferriss?

  I'll do my best to wrap it up without making it a Dr. Evil life story. Good morning, everybody. Thanks for coming. So let's see, graduate, moved to California, Northern California to be part of the tech pinball machine for serendipity. I actually think that was a very important decision, just geographically. Choosing where to be and then what to do being really secondary. Worked in data storage, selling, storage area networks, had a desk and a fire exit, definitely not up to code. I remember it was really packed to the brim. Learned a lot about selling. I think everyone should have a service job, work in a restaurant or something like that and have to sell for a period of time.

• 8:42Tim Ferriss?

  You learn so much about human interaction and I learned how to reach out to CTOs and CEOs and so on. How to reach them, playing the long game, not trying to sell a seven-figure system in one phone call. All of these things translated to many things later. I couldn't have seen that coming, but they did. Then I started this sports nutrition company, long story. A lot of people here probably know some of the bare bones aspects of it from the four hour work week. That experience was simultaneous with a professor of mine, Ed Shao, who taught high-tech entrepreneurship at Princeton, which had a huge impact on me. Inviting me back to guest lecture twice a year. And that went from 2003 to 2013 or so. Those notes later became the outline for the four hour work week.

• 9:27Bill Gurley?

  How long did the startup exist?

• 9:30Tim Ferriss?

  Startup existed until, let's see, I want to say 2009 or so, when I sold the company. Not for any huge sum of money, but I sold the company around 2009, so.

• 9:40Bill Gurley?

  And how long was that experience, six years?

• 9:43Tim Ferriss?

  The experience of building it?

• 9:44Bill Gurley?

  Yeah.

• 9:45Tim Ferriss?

  I would say the building phase was the first three or four years. First year and a half, had no idea what I was doing. Say the subsequent year and a half to two years was building out distribution. And then I became very bored with the entire thing and was looking for a graceful exit, which turns out, you know, selling a company, even if it's for a very small sum of money, is one way to do something new.

• 10:09Bill Gurley?

  Did you raise money or?

• 10:10Tim Ferriss?

  I bootstrapped the whole thing. So it was credit cards, savings, trying to play, buying remnant advertising against incoming revenue, getting prepayment from distributors. You will be the exclusive distributor featured in this print ad if you pre-purchase X amount, which would then give me the money to pay for the ad in the first place that I negotiated 80% off of, because it was last minute, things of this type. So all of those games were what drove a lot of the growth, figured out that playbook. And then the focus really became trying to figure out what the hell I wanted to do when I grew up. And I'm still doing that, I guess.

• 10:49Bill Gurley?

  What did you learn from the startup? What were the key takeaways?

• 10:51Tim Ferriss?

  A few key takeaways from the startup were, number one, if you want to reach the decision makers, just call outside of business hours. So if you're actually cold calling, I was cold calling, smiling and dialing a lot and cold emailing, then just do it before 8:30 and call after 6:30. And very often, even in a company of 100 people, you'll get one of the top brass answering the phone at the end, which was astonishing to me. Next, I would say if you're going to talk to technical people, and I was not technical, but if you're going to talk to, say, VPs of engineering and CTOs, do your homework. And I ended up being really, really successful as a salesperson, not because I studied sales per se,

• 11:32Tim Ferriss?

  but because I actually took the time to try to understand what RAID was, what all the bits and pieces were that made up the hardware, what use cases would lead to them using Solaris versus something else, and being able to guess correctly what their setup was without them telling me anything, which opened the door to more involved conversations. Those would be a handful of things. And the value of storytelling, ultimately, for everything.

• 11:59Bill Gurley?

  For everything.

• 11:59Tim Ferriss?

  If you're a human.

• 12:00Bill Gurley?

  I agree with that.

• 12:01Tim Ferriss?

  Storytelling is key. It's the crux.

• 12:03Bill Gurley?

  So the life as a startup entrepreneur eventually wasn't working for you.

• 12:11Tim Ferriss?

  It wasn't working because the, for me, the learning curve had kind of flattened out.

• 12:15Bill Gurley?

  Yeah.

• 12:15Tim Ferriss?

  And I wasn't sure how to change that. I knew I wasn't a great manager. I didn't aspire to become a great manager, which continues to this day. I should probably revise some of that. So then, as is the case now, I have a very lean team, very, very small team. And if we flash forward, then the notes of that class become the basis for the Four Hour Workweek. I did not want to write a book, but a friend of mine who was an author suggested it and started making intros to editors and agents and so on. And I had to reply to those people, and that gathered its own steam. And the Four Hour Workweek is what, as a lot of people here know, opened the floodgates for everything. That got the visibility that led to the angel investing, that bought me permission to write a second book. And I'd say

• 13:01Tim Ferriss?

  To a question that you posed before we got on and you may have also just asked it. When did I start doing something intentionally or thinking about a trajectory? And I would say that's probably when I made the pitch for The Four Hour Body. Because I don't have a grand five-year plan. I don't have a grand 10-year plan. That's today, was true then as well. But I wanted to choose the door that opened more doors. And I realized that despite, or maybe because of the pressures that I felt externally from just about everyone to write The Four Hour Work Week 2.0 or The Three Hour Work Week, I could very quickly paint myself into a corner where that was my only niche and the only place I felt comfortable and the thing I felt I needed to defend.

• 13:44Tim Ferriss?

  And so I thought, well, I can always come back and do that later. That will be available, so let me do something in a completely different section of the bookstore. The publisher's gonna say yes because they are willing to at least take this bet. They'll give me a decent, not even a decent, a very good advance, which will actually make up for the 75 grand that I got paid over a year and a half for The Four Hour Work Week initially. And that type of decision-making, I think, has typified and defined a lot of my key decisions, which is entirely seemingly out of left field, but of interest to me that will potentially open new doors.

• 14:22Bill Gurley?

  When was the second book and when did the angel investing start?

• 14:26Tim Ferriss?

  Four Hour Work Week came out April 2007. The angel investing started within, I would say, 10 months. I owe Mike Maples Jr. a debt of gratitude for that. I traded him advice for exercise and diet for

• 14:39Bill Gurley?

  An Austin, like yourself.

• 14:41Tim Ferriss?

  Austin as well, meeting at Hobie's for breakfast and him telling me about his deals just so I could learn about them. And then The Four Hour Body was published in 2010, which means that I was probably working on it for two years.

• 14:53Bill Gurley?

  So you said you made 75 grand and you're hustling. How do you afford to angel invest?

• 14:59Tim Ferriss?

  Well, fortunately, the advance gets earned out. I had the savings from the prior company. So I had some savings and decided to place very, very small bets. So I was co-investing with checks of, say, $10,000. And the intention really early on, which comes back to playing the long game that I mentioned earlier, I wanted to be the cheapest, most valuable labor on the cap table, meaning like, here's a $10,000 check. Now I'm going to put in so much effort and try to be so helpful that it will make no sense to you because my ROI is probably not going to pay for the time I'm putting in. But that was to create raving fans and get referrals. And so that's what I did for the first six months. Very small

• 15:42Tim Ferriss?

  checks, putting in way too much time, but for me, it was actually the perfect amount of time, getting referrals. And then that steamrolled in such a way that I was able to get advising. So I was able to get sweat equity.

• 15:54Bill Gurley?

  Let's run down the angel path for a little bit and then come back to podcasting. So I didn't mention when I mentioned all the amazing things you've accomplished, your angel investing track record, which is actually pretty good, right?

• 16:05Tim Ferriss?

  It's turned out, yeah.

• 16:07Bill Gurley?

  So tell the audience some of the companies you invested in.

• 16:11Tim Ferriss?

  I invested in, let's see, invested. When I say invested, it's important to note that I mean time in a lot of these cases because I didn't have the bankroll to pay for investing. And I probably couldn't have invested even if I'd wanted to. So Uber would have been when there were two employees. Yeah, you've heard of it. And Shopify, first advisor when they had eight to 12 employees, first investor in Duolingo, that was a bit later, early secondary on Facebook and Twitter.

• 16:40Bill Gurley?

  What was your rule set back then? How were you deciding what to do?

• 16:44Tim Ferriss?

  Early rule set was super simple and it's the same rule set. It hasn't changed for me. And that is. Something that addresses a personal problem that I have, that I understand, that I could be a power user of, that I think I could feel very good about recommending to my audience. That's it. And that has worked pretty well. I mean, as you know, there are a lot of whiffs. I mean, you get a lot of things that zero out, but it's a power law game. So you're really aiming for the handful that return the fund. And I was always betting, this is actually another maybe key framework that I would say I've used over and over and over again. And that is, I viewed the angel investing and all of that as a real world MBA, assuming that I would lose all of

• 17:27Tim Ferriss?

  the money I put in, right? You don't get your tuition paid back to you by the same institution, but that the skills I would develop and the knowledge I would acquire and the relationships that I would end up cultivating would in the long term pay for all of it.

• 17:44Bill Gurley?

  Are there takeaways you had from specific investments that became part of your minimal?

• 17:50Tim Ferriss?

  I think the most consistent lesson for me, and I'm not recommending anyone try to replicate this, but the timing was also really good in that period of time. But choosing people that you really like to work with, because a lot of these startups are going to take, if they turn out well, longer than the average marriage. So you really want to make sure these people pass the beer test. Like, are you going to want to go out and have a beer with this person?

• 18:15Bill Gurley?

  Right.

• 18:16Tim Ferriss?

  And that doesn't always apply. And I think really good founders are often pretty cantankerous. But I stuck to that. And for instance, you know, I was thinking about some of the decisions in this area, and it's true for so many others. I could say, well, becoming an advisor to Uber was a really good decision, but that's not really the right story. The right story is working with Garrett on StumbleUpon.

• 18:45Tim Ferriss?

  Was the right decision, which didn't pay off, but we got to know each other and that led directly to Uber. So rather than looking at the decisions that are most well-known for, say, successful people, I, even to this day, when I'm interviewing people, I look for the antecedents, like, okay, well, let's look at what happened before that, without which those great decisions that are on the cover of magazines never would have happened.

• 19:09Bill Gurley?

  We were talking about this in the back because it's a question of can you increase your optionality for fortune or luck or whatever anyone else says by taking meetings that may seem superfluous or uncertain or that then lead to these big outcomes.

• 19:24Tim Ferriss?

  Yeah, totally. And for me, moving to the Bay Area and then later moving to San Francisco. So it wasn't enough to just be in the Bay Area. I moved all over the place, eventually got to San Francisco because I realized if I want maximum serendipity, if I want it to be easy for someone to say, hey, I'm over at this place, come and have a drink, rather than driving an hour to an hour and a half to get there, I needed to be in San Francisco or I wanted to be in San Francisco. And the question of where, I think, in an increasingly virtual world, actually becomes more and more important. If you can operate in person, you have a huge competitive advantage.

• 19:59Bill Gurley?

  And it's a contrarian mindset today where everyone's relishing in the fact that they can live wherever they want.

• 20:05Tim Ferriss?

  Yeah, so choosing at least seasonally, if you're not willing to kind of bet the farm in terms of moving to one place, to be in certain locations. If you're still in that growth phase of your career or life, professionally speaking, then I think that's undervalued.

• 20:23Bill Gurley?

  Yeah, I agree with that. And some of the work I've done in studying, like Danny Meyer, when he wanted to be a great restaurateur, he moved to Europe and worked in any job he possibly could.

• 20:34Tim Ferriss?

  It's all, it's all the same. People ask about patterns across the 700 or so interviews I've done. I'd say that's easily one of the most obvious.

• 20:42Bill Gurley?

  That's cool. Now, you've mentioned recently publicly that you've backed away from angel investing. So for someone that's had such a prolific run and successful run, why step away? That doesn't seem to make any sense.

• 20:55Tim Ferriss?

  Yeah, I'd say number one, I didn't grow up with much money or spending much money, and I still think I'm actually quite bad at spending money. So. Why gather more Skittles until I figured out how to use the Skittles I have? I think is one thing that comes to mind. Number two is things have gotten more difficult, I think, in angel investing. There's just more noise, more competition. It's like in the early days, I learned how to count cards with single deck blackjack with a handful of friends. And now they're like, eh, we think we're gonna change the odds, we're gonna swap it.

• 21:29Bill Gurley?

  You need a different brain to count into an eight deck shoe with three pit bosses.

• 21:32Tim Ferriss?

  Exactly. The game is harder. And I also feel like, as with most things, my bolus, the majority of my really fast, nonstop learning happened in the first few years. And that there are a lot of people who can invest. And there are a few things that I think I'm reasonably good at, that I've, I don't want to say neglected, but paid less attention to. And I prefer to return to some of the creative stuff. And also I've been doing it for a long time. So generally, when I've been doing something for five plus years, I think, what is something that for whatever reason I'm attracted to? That seems completely unrelated, it's a total left turn.

• 22:14Tim Ferriss?

  And that is something that I'll try to experiment with because it's just worked for me over and over again. If something energetically is pulling me, I want to pay attention to. And right now that's fiction and animation and AI and a handful of other tools.

• 22:28Bill Gurley?

  Let's go back now to your journey as a creator. So where does the second book become the blog, become the email list, become the podcast?

• 22:37Tim Ferriss?

  I'll put them in order. So the blog was started in 2006, which was of course before the book came out in 2007. That's not a coincidence. I had interviewed, long before I had the podcast, I interviewed people. That's part of the reason it was easy for me to segue to the podcast. But I interviewed best writing authors, so people who had books that were acclaimed and that had won national book awards and so on. While I was writing The Four Hour Workweek, to try to be better at writing books. I also interviewed, reached out to. Best-selling authors, not always the same thing, and asked them about launch and the vehicles and the types of media that seemed to be undervalued but were increasing

• 23:19Tim Ferriss?

  in impact in their mind. And there were patterns. Blogs were the big thing. They said, "These things called blogs seem to move a lot of books, but most authors pay no attention to them." And I was like, "All right, I don't have a whole lot of wiggle room here for a number of reasons with, say, a large budget for launch. I know the publisher's gonna want to control quite a few variables. I'm going to focus on two things: blogs and in-person events to reach bloggers." And to do that credibly, I thought I really should have a blog that has some good articles on it. And began that in 2006. And that then led

• 23:57Tim Ferriss?

  to the book, or I should say, was followed by the book in April 2007. March 2007, really important inflection point, was presenting here for the first time. Thank you, Hugh Forrest, for giving me overflow space. I think it was next to a cafeteria, but it was like a last-minute cancellation. I rehearsed at my friend's garage using his Chihuahuas as my test audience. And if they got bored and walked away, I was like, "I'm losing them. I'm losing them." And so I'd do it again. And that really planted the toehold in tech that I think directly contributed to the success of the book in the first,

• 24:37Tim Ferriss?

  certainly in the first year. And then you have, let's see, email gathered with the very first website. So I was gathering email beginning in 2007. I knew that email could be important, but I didn't send the first email until something like 2014.

• 24:54Bill Gurley?

  You just collected them?

• 24:55Tim Ferriss?

  I just collected. I didn't do anything with them. And then I continued to work on the blog. That became the way I communicated directly with my audience, which maybe we'll come back to, based on WordPress, which meant I did not feel captive to any platform. I knew that I could take this open source Platform. And if I wanted to migrate my blog and my content, I could do that. And that flexibility of migration has been a core tenet of my professional life, I would say, ever since.

• 25:25Bill Gurley?

  When you're interviewing these other authors, you've transitioned to intentionality, right? At that point, you're trying to do the best you possibly can on that product.

• 25:35Tim Ferriss?

  Yeah, on the books, on the books for sure. And I wanted books that would last. And thankfully, they have. I mean, these books still continue to do very well. I think most of.

• 25:45Bill Gurley?

  Because the content's more evergreen?

• 25:47Tim Ferriss?

  I think it's almost all evergreen. And that's true for the podcast as well. I really don't want to produce content that has an expiration date that is really obvious. That just requires more work for me.

• 26:01Bill Gurley?

  What year are you aware you're a professional content creator?

• 26:05Tim Ferriss?

  I thought of myself at that time as, I would say, a professional writer. And books are a very particular thing. They have a permanence and they have a static nature. You can update them, but it's harder. It's easier now with Kindle. That requires a lot of forethought. And I think that that's something I also try to use now. I still try to measure twice, cut once with producing any content, which in a world of kind of be fast to be first, I do think that pause gives you an advantage. And then as far as say, I've never thought of myself, to be honest, as a content creator. It's always been as a writer or an interviewer, something that makes it more finely categorized.

• 26:50Tim Ferriss?

  Because it helps me then to work on a craft. If you say I'm a creator, that doesn't give you a great search function for trying to improve your craft. So I've always been very finely sliced. And it was author, it was then investor, early stage, consumer facing tech investor, to be clear. Then in 2012, The Four Hour Chef burned me out. It was probably a three to four year project that I put together in a year and a half. Very proud of the output, but it just physically demolished me. And in the process of doing the launch, I'd asked another cohort of bestselling authors, which platforms were neglected, but.

• 27:32Tim Ferriss?

  Seemingly powerful, they said podcasts. I went on a whole host of podcasts. I was very lucky to be there at that point in time also. So you had Joe Rogan, you had Nerdist, you had Marc Maron, and this entire cohort, Adam Carolla. Those really moved the needle. They were also such a sharp contrast to the morning TV shows and so on that I'd done previously, where I could actually get into nuance, I could curse, I could be myself. I had a blast and decided, I am too burned out to do another book. I want to try something else. Let me try podcasting. I'll do six episodes to give myself a graceful exit. I'll set that expectation up front. It was either six or 10 episodes. And even if it fails,

• 28:14Tim Ferriss?

  this is coming back to something I mentioned earlier, even if it fails, meaning the audience doesn't like it, or I don't continue doing it, I will get better at interviewing. And I will deepen relationships or make new relationships, all of which will persist after the hypothetical failure. And then I just kept doing it because I was having fun.

• 28:33Bill Gurley?

  Do you have a similar story to the book story on podcasting or interviewing where you went out and studied the art or the craft?

• 28:41Tim Ferriss?

  Definitely. I studied anyone I thought had something to offer, even if the format was very different. That would include people like Dan Carlin, Hardcore History, which I think is one of the most spectacular podcasts of all time.

• 28:55Bill Gurley?

  I don't know that one. The audience might. Tell us about him and why that's so.

• 28:59Tim Ferriss?

  Hardcore History is, I would say, one of the super, super first gen, long-form podcasts. Dan Carlin does a deep dive on some facet of history, some chapter of history. For instance, Wrath of the Khans about Genghis Khan is, I think, four or five parts. Each one is probably four to five hours. And there's no one who, if he had gone to a market research firm and said, what do you think of this idea? Uniformly, he would have been told it was a terrible idea, doomed to failure. If they could bet the farm against him, they would. And it worked. And even to this day, I think he just had a new episode come out a month ago. He has multiple podcasts now, so he can scratch the itch of doing something more

• 29:41Tim Ferriss?

  frequently on current events. But the Hardcore History podcast, I think there was an eight month interval where there were no episodes. So he's effectively publishing audiobooks, but it became massively successful. And I love studying those outliers because anytime you're told you have to do A, B, and C, my first question, at least internally, is can I find exceptions? And if you can find exceptions, it's not a must.

• 30:05Bill Gurley?

  And what did you, anything you took away from him or others that you borrowed?

• 30:10Tim Ferriss?

  Don't believe the, any dogmatic rules around what you have to do or what you should do. Test, experiment. It doesn't matter to maybe paraphrase Richard Feynman, it doesn't matter how beautiful, how pretty your theory is, if it doesn't match with experiment, it's wrong. So test, do lots of tests. And I, in the early stages, also took my transcripts and ended up hiring a senior researcher from Inside the Actor's Studio, amazing show, to look through my transcripts and identify where I could do a better job.

• 30:42Bill Gurley?

  Wow.

• 30:43Tim Ferriss?

  Where did I not follow up on a question that was a gem? How could I have reordered the questions for a better flow? All of these types of things.

• 30:53Bill Gurley?

  And that was fruitful, that exercise?

• 30:55Tim Ferriss?

  Very fruitful.

• 30:56Bill Gurley?

  Yes.

• 30:57Tim Ferriss?

  And at the very least, I think everybody here should record a podcast just so you have to listen to yourself talk, and you will find so many things that drive you insane. Everyone will have some form of tic that will drive you batty. And you'll notice where you're sloppy also in your thinking, because really, I mean, speaking is just thinking out loud. And you become a much clearer thinker, you become a much more concise, deliberate thinker. And for that reason, I think everybody should try a podcast for at least three episodes, even if you never publish it. Interview your family. Save that for your kids or grandkids. Serious.

• 31:37Bill Gurley?

  What makes you a great podcaster? Can you reflect on that?

• 31:40Tim Ferriss?

  I'll answer it maybe a little bit differently. I think what makes me a successful podcaster is, first and foremost, I chose a format very consciously that was simple enough that I would, I could persist in doing it. So I knew I would have the ability to endure, I would have the endurance to...

• 32:05Tim Ferriss?

  Do a long form interview and then follow that with minimal editing and share it. I knew I could do that. And many podcasters, I think, commit to failure before they even start by choosing a format that is going to be too difficult or too exhausting, given other obligations. So there's this elephant graveyard of, you know, three-episode podcasts for that reason. Yeah. The second is, I chose a category, let's say, and I earned the ability to do this. I'm not sure if I could have done this in the beginning. Four Hour Workweek was very narrow. Four Hour Body then says, hey, and I guess it was proved to me that the hypothesis was correct, that a lot of my readers would follow me for my thinking, not just for a single topic.

• 32:49Tim Ferriss?

  And then it kept broadening. And by the time I got to the podcast, landed on the very unoriginal title of The Tim Ferriss Show, because I didn't want to apply a label that would constrain what I could do. And you see what can go sideways. There are a lot of things that can go right with a very narrow niche. But if, for instance, and this is very common, you decide you're going to be the funny voice, wear unicorn hat guy on your YouTube channel, and God forbid that becomes mega-popular, like, four years later, are you still gonna wanna be the funny voice, unicorn hat-wearing guy on YouTube? Maybe not. And many people end up feeling like they can't escape a monster of their own making, if things go right.

• 33:31Tim Ferriss?

  So I was able to make it very broad, which means I can explore my interests wherever they might fall, which also gives me endurance, which is a competitive advantage. If you are not able to endure, especially with the amount of noise and the number of entrants now, I think it's very, very challenging to establish any type of firm footing upon which you can build a business, which was never my intention. I didn't monetize the podcast until... I don't know, 20, 30 episodes in, which I still would recommend to most people, but those are some of-

• 34:06Bill Gurley?

  That waiting window.

• 34:07Tim Ferriss?

  That waiting window.

• 34:08Bill Gurley?

  Yeah.

• 34:08Tim Ferriss?

  Because if you focus on, this is just my perspective, my two cents, I'm sure there are many counterexamples. I would love for people to point at examples that prove this to not be correct for everyone, because of course that's true. For me, I wanted to focus on becoming as good as possible at the craft. I wanted all of my attention to be on that. And we all procrastinate in different ways. As a writer, my favorite way to procrastinate, reading. Socially acceptable. They're like, wow, you're such a, such a serious reader. It's amazing. I wish I could be so dedicated. I'm like, damn right, I'm dedicated, but really what I'm doing is procrastinating, doing the thing I should be doing, which is the writing.

• 34:46Bill Gurley?

  Right.

• 34:46Tim Ferriss?

  Similarly, as soon as someone dangles some carrot in front of me that's related to like, marketing, business models, whatever. Oh, I love thinking about that stuff. I'll just skip the hard work, which is focusing on gaining better at interviewing.

• 34:57Bill Gurley?

  In kind of learning from your experience and your success, one of the things that jumps out, you talk about controlling your own destiny. And email and podcasting are two content forms. They're both these highly distributed things, just by the way they're technically implemented.

• 35:16Tim Ferriss?

  Yeah.

• 35:17Bill Gurley?

  That's been something that's been, you've been passionate about all along, or you feel like an-

• 35:21Tim Ferriss?

  I feel like it's an existential imperative.

• 35:23Bill Gurley?

  Right.

• 35:24Tim Ferriss?

  To have direct communication with your audience to the extent possible. And so I gathered email, starting in whatever it was, 2007. Did an email, I want to say, I'm getting the dates slightly off, until maybe 2013 or 2014, somewhere around there. And then started Five Bullet Friday in 2015. So this very short format, easily digestible. Here are the five coolest things I found through my enormous network this week. Check them out. You can read it in 60 seconds. So that, that Five Bullet Friday-

• 36:00Bill Gurley?

  Reinforce the podcast.

• 36:01Tim Ferriss?

  It reinforces the podcast in some instances. It is legitimately whatever I have found most interesting that week. Took a photograph of a book I'm reading right now and sent it to my team, saying, add to 5BF, I'll draft the bullet later. Art and Arcana of Dungeons and Dragons, if anyone's interested. Beautiful book. And that-

• 36:22Tim Ferriss?

  Ended up being, I think, one of the fundamental key decisions for increasing direct access to my audience because podcasting is largely a black box for analytics. And just by contrast, I would say, I remember having a conversation with someone who had a massively successful business built on one or two Facebook pages. This was probably five years ago and I asked, I asked him what it was like to run these businesses and he said, "It's like having the most profitable McDonald's in the world on top of an active volcano." Because if the algorithms are changed, if your organic reach is throttled. Right. Ah, fuck. Now you have a real problem on your hands. And I never wanted, I have enough trouble sleeping as it is, I did not want to be kept

• 37:07Tim Ferriss?

  up at night worrying about those types of things. So yes, I use Facebook. Yes, I use Instagram. Yes, I use all these platforms, but I fully anticipated that at some point, organic reach would be throttled across all of these. Yep. Maybe it's the next procession that sparks it and people need to improve their bottom line, but at some point that's gonna happen. And I don't want to have all of my chips, I don't want to even have the majority of my chips in those places. From a risk management standpoint. From a risk management standpoint. And I am not, I don't view myself as a risk taker. First and foremost, I really view myself as a risk mitigator.

• 37:45Tim Ferriss?

  Just a quick thanks to one of our sponsors and we'll be right back to the show. This episode is brought to you by AG1, the daily foundational nutritional supplement that supports whole body health. I do get asked a lot, what I would take if I could only take one supplement? And the true answer is invariably AG1. It simply covers a ton of bases. I usually drink it in the mornings and frequently take their travel packs with me on the road. So what is AG1? AG1 is a science-driven formulation of vitamins, probiotics, and whole food sourced nutrients. In a single scoop, AG1 gives you support for the brain, gut, and immune system. So take ownership of your health and try AG1 today. You will get a free one-year supply of vitamin D and five free AG1 travel packs with your first subscription purchase.

• 38:30Tim Ferriss?

  So learn more, check it out, go to drinkag1.com/tim. That's drink A-G-one, the number one, drinkag1.com/tim. Last time, drinkag1.com/tim. Check it out.

• 38:49Bill Gurley?

  One other thing you talk about a lot is staying lean and you run this thing at a massive scale, but you have very little team and infrastructure, correct?

• 38:58Tim Ferriss?

  Yeah, very few.

• 38:59Bill Gurley?

  And you just said something earlier that I keyed on, you said endurance. Is part of the endurance tied to that? Like just not having the overhead of it all?

• 39:08Tim Ferriss?

  I think they are tied together and I should say, there are many instances for many people where building out teams makes perfect sense. Because I recognize some of my weaknesses, as I mentioned earlier, I don't think I'm the most effective, actually, I think I am an effective leader. I'm not the easiest person to have as a manager and I recognize that. So I have a very lean team. I mean, currently just have three employees and we do everything effectively with that team. We have very well-defined processes and it maps back to the four-hour work week, honestly, which is like define, there's define, definition, elimination, automation, liberation, we will get into liberation today, but defining exactly what your outcome measures are, to

• 39:53Tim Ferriss?

  use the fancy acronym, KPIs, right? What are you measuring week to week, month to month that matters? Why are you doing these things? What are the priorities, one, two, let's just say? Then eliminating as much as possible that don't relate to driving those forward and then automating as much as possible with really, really good processes. So we have very, very good processes for the podcast and for that reason, we don't need 20 people, we don't need 30 people. And I've pushed back a bit against the trend towards video because it would end up increasing the infrastructure required. It would also fix me to one location and I'm not willing to make that trade-off largely.

• 40:34Bill Gurley?

  How do you do prep? You're doing this many podcasts, you're not reading a thousand books a year, are you?

• 40:39Tim Ferriss?

  No. Step number one is write a blog post, which is called, I think it's called the decision that removes the thousand decisions and then in parentheses, why I'm not reading any new books this year. So make it a policy. If you, if you want to say no to a category of thing, make it a public policy. So number one is making it a public policy. I'm not reading any books published this year. That way I can tell every guest, not reading books without having to ruffle feathers. The next step is

• 41:06Tim Ferriss?

  Looking at, before I even invite someone, looking at long-form video and audio to the extent possible, and maybe I have to find something that was recorded behind doors, that's something I'm usually pretty good at doing. Interviews, Wikipedia, what am I looking for, though? What's the filter? I'm looking for a handful of things. One would be any odd hobbies or passover comments that weren't fleshed out, that I think would make for a good first question or second question, in part because it will prove to the interviewee that I have actually looked at the details and done my homework, which is really important for a lot of interviewees. Because if you don't prove that early, they're gonna go on autopilot, and they're gone. They're checked out. They're thinking about their next vacation. Right?

• 41:50Tim Ferriss?

  You might as well be talking to Max Headroom or something, it's just not gonna be very interesting. And then, I would say, beyond that, I will try to identify what has been neglected, what has not been mentioned. And that can lead some interesting places, not always comfortable places, but that can lead, for instance, if they haven't talked about their childhood at all, I might ask them if they're okay with me asking about their childhood. Few other key, I would say, housekeeping, and this is also in the category of prep, it's just right before we record. I will talk to anyone, we did this, even though we know each other, for five to 10 minutes beforehand. Number one, just for so everybody can get their hamstrings warmed up, we're not trying to sprint out of the gates after hitting record.

• 42:35Tim Ferriss?

  Just talk. But there's a format. I will say, "You have final cut," just like every one of my guests, this is no gotcha show, I've had that happen to me, it sucks, this is a friendly, my job is to make you sound as good as possible. "You have final cut, we can send you the transcript, so don't worry about it." It's not live, so bathroom breaks, water breaks, if you wanna restate something, we can do that. And then I ask them, and... People comment on this because almost no one asks this. What would make this a home run for you? Looking back after it's published, say, two months after it's published. What would make this one of your favorite interviews or something that you would point people to? Great, and then I can help steer it. And that puts people at ease and helps them to be vulnerable.

• 43:19Tim Ferriss?

  Another thing that I will think of, if I want to try to unbox something that hasn't been explored before, there's probably a good reason it hasn't been explored. So I will find something in that same category. Could be childhood, could be relationships, could be a business failure. I will volunteer that information from my side first.

• 43:38Bill Gurley?

  Yep.

• 43:38Tim Ferriss?

  Just to provide some transparency, because I know that sometimes it seems like I'm talking a lot. And I am, but there are reasons for, in this case, doing that. I'll ask the question so they can think about it. Then I buy them time so that they don't feel too under pressure. Then I volunteer an answer from my own life that basically makes me vulnerable simultaneously, and it makes people much more likely to reciprocate. So those are a few of the things that I do. If I have any access to that person or their lives through friends or acquaintances, then I will also back channel to a few folks and ask them what topics or questions.

• 44:23Tim Ferriss?

  I'll always preface, I'll say, "I'm obviously doing a ton of my own homework, because people don't want to help you, including my friends, if you're being lazy." So I'll say, "I'm doing a ton of my own homework, but are there any questions or topics that you think could be fun or uncommon to explore with so and so?" I did this with, I sent a text to you like that for Danny Meyer when I interviewed him recently.

• 44:42Bill Gurley?

  Right, and you earn reciprocal trust through those, many of those techniques.

• 44:47Tim Ferriss?

  Absolutely, and then I will also, and this leads to... A lot, and it smooths out the entire process. I will very frequently ask guests, not always, but ask them if there's anyone they think would really have fun having a conversation on the podcast. So I'd say 70% of the guests come from other guests at this point.

• 45:05Bill Gurley?

  You asked me that about Mike Mobison.

• 45:06Tim Ferriss?

  Yeah.

• 45:07Bill Gurley?

  You just had him on.

• 45:08Tim Ferriss?

  I did.

• 45:09Bill Gurley?

  One topic that I adore, just as a fan of media, is what I call pure respect. So I remember Shaq went on this five-minute rant about all the greats that had come before him, which was just super endearing. Tell us a couple of other podcasters that you respect and why.

• 45:28Tim Ferriss?

  There are a lot.

• 45:29Bill Gurley?

  You mentioned one.

• 45:30Tim Ferriss?

  Yeah, yeah, I mentioned one. There are many, and I respect them for a whole lot of different reasons. I would say it runs the gamut from, say, like a Guy Raz, so How I Built This.

• 45:41Bill Gurley?

  Yeah.

• 45:41Tim Ferriss?

  Who is using, I don't want to say this American life format, but he's doing a lot of prep, a lot of recording, and then immaculate editing with his team, and telling a story arc, so they might move things around. And that is a particular game. That's a very particular game, and he's very, he and his team are very, very good at it. I would say, this is going to seem like an easy one, but Joe Rogan has done an excellent job of becoming a category of one. He wasn't emulating someone else. And for those wondering where I get, where you might be able to read up on how to do this, there's a chapter called "The Law of Category in the Twenty-Two Immutable Laws of Marketing."

• 46:24Tim Ferriss?

  A lot of the other chapters are outdated. This one, everyone should read. He did an excellent job of, number one, experimenting with a brand-new format early. He has been in the podcasting world for a very long time, and he's tested a lot.

• 46:38Bill Gurley?

  Yeah.

• 46:39Tim Ferriss?

  And he found his footing reasonably quickly, and the combination of entertainment and in-depth interview.

• 46:49Tim Ferriss?

  And tripling down on long format, I think he deserves a lot of credit for popularizing. He also made incredibly, incredibly good strategic decisions before most. I'll give you an example. YouTube, one of the world's largest search engines, who did one of the very first spectacular jobs of capturing podcasts on YouTube, not just long form, but using clips on a separate channel. So he has played that game like the consummate professional. And so he would be another example. I think Lex Friedman does an excellent job. I'd say our formats are probably closest in some respects.

• 47:33Tim Ferriss?

  Patrick O'Shaughnessy, who we both know, who focuses on investing in investors, I think does a fantastic job. I could list another 20. There are some really, really good interviewers out there, but it's not enough to be a good interviewer. I really think you need to seek to be a category of one. It's a lot easier to be the only than it is to be the best when you have millions of podcasts to compete against. So spend a lot of time thinking about positioning.

• 47:59Bill Gurley?

  I have a couple of questions about big events in your world that have happened in the past two or three years. So Spotify leaned heavy into podcasts, did a couple of high dollar acquisitions with Joe and Bill Simmons. And at least based on what they've said publicly with the layoffs and stuff, they backed off a little bit.

• 48:19Tim Ferriss?

  Yep.

• 48:20Bill Gurley?

  What are your thoughts on that in and out and what it means for your world?

• 48:23Tim Ferriss?

  I think first and foremost that it was a very smart strategic decision to acquire talent and that podcasts and audiobooks or some form of audiobooks are probably existentially important to Spotify versus say an Amazon, right? Amazon has

• 48:44Tim Ferriss?

  Put a lot of resources into podcasts and certainly they are the dominant player in audiobooks with Audible, but they could survive without those things.

• 48:51Bill Gurley?

  Uh huh.

• 48:52Tim Ferriss?

  And for that reason, for Spotify to acquire talent at whatever price necessary to fold in existing audiences, to get a lot of PR, which gets the attention of other high-profile creators who then might reach out through their lawyers or agents to have conversations. I think it was very smart and I expected, no matter what, that once they became a more meaningful percentage of every podcaster's downloads, that they would back off of that. Because why buy audience when you get to the point where most podcasters have to pay attention to you and they're coming to you at the same time they might go to Apple to ask for promotional help, you've established a different level of leverage at that point.

• 49:35Tim Ferriss?

  So it doesn't surprise me that they've backed off. I think that would have happened either way.

• 49:40Bill Gurley?

  You're in a position to know this, I'm not. How successful have they been encroaching on Apple's podcast player or others?

• 49:47Tim Ferriss?

  They've grown a lot. They've grown really significantly. I can't link that causely to

• 49:54Bill Gurley?

  Right.

• 49:54Tim Ferriss?

  The one lever of, that they've pulled in terms of

• 49:58Bill Gurley?

  Where are, do you know on a, as a percentage, at least for you?

• 50:01Tim Ferriss?

  You know, I don't and I would share it if I had it, but it's easily tripled or quadrupled in the last handful of years, without a doubt.

• 50:08Bill Gurley?

  Cool. And then the second thing I was gonna ask you about on this front is just Twitter. Obviously Twitter's been through a lot of changes in the past

• 50:16Tim Ferriss?

  Yeah.

• 50:17Bill Gurley?

  two years, but it's also a platform for redistribution, pretty powerful one in your world.

• 50:23Tim Ferriss?

  I use Twitter in a very particular way. I am not totally convinced of its power as a distribution mechanism. It may be just the same 200 people yelling at one another all the day, every day. It's hard for me to tell sometimes, but Twitter principally for me is a way of connecting with, I would say, a third of my podcast guests. And it is an excellent means by which you can make contact with someone who would otherwise be very difficult to get hold of.

• 50:52Bill Gurley?

  Oh, the DM part?

• 50:53Tim Ferriss?

  DM, because

• 50:54Bill Gurley?

  It's unbelievable.

• 50:54Tim Ferriss?

  Because if you are reaching out, say, to have a conversation with someone through an agent, a lawyer, A manager, a fill in the blank. There's so many layers and so many hurdles. Even for me, it's very difficult to make contact with a lot of people. Twitter just gets rid of all of that because if you both follow each other, and in some cases, you have open DMs, but you can communicate with someone and they don't have to share any of their contact information. They're not going to be getting a late night texts from you, thinking of you, "How are you?" You know, they're not going to have, the creep factor potential is much lower. So I would say probably a third of the people I ended up having in my book Tribe of Mentors came from DMs on Twitter.

• 51:39Bill Gurley?

  Yeah, I've wondered over the years if LinkedIn hadn't polluted their in-mail and made it monetized.

• 51:44Tim Ferriss?

  Yep.

• 51:45Bill Gurley?

  And they had done what Twitter did, how much of the most powerful conversations in the world would have happened?

• 51:51Tim Ferriss?

  Yeah, I will say, I do think LinkedIn is going through a powerful resurrection of sorts where I actually think LinkedIn is going to become a more powerful platform than people expect for broadcast. And I've seen inklings of that. However, I should add a warning, which is if you don't have a focal point, like an email newsletter, or you don't have a focal point, like the craft of improving your podcast, because quality always has a market. If you aim to be the best in a category of one, right now, I know I'm combining a few things I said might be separate. They're not mutually exclusive. If you don't have that type of focus, you haven't made those definitions ahead of time, you are going to be like a rabbit in a maze trying to find a piece of carrot.

• 52:34Tim Ferriss?

  You're going to be jumping from one platform to the next, to this, to this, and even on one platform, "Oh, the algorithm changed. Now I have to change everything that I'm doing." It's all about dogs farting now. Okay, great. How long can it be? 27 seconds? Okay, that's what I'm going to do now. And you are going to lose. You're not going to actually, I think, achieve any of the goals if you have defined those goals in advance at all.

• 52:56Bill Gurley?

  Cool. So what I'd like to do now is, this gentleman, Tim Ferriss, wrote a book called Tribe of Mentors, where he came up with a list of questions for a whole bunch of different people. So I'd like to turn them on you. Because I want to earn your trust, I'll answer them first and show a little vulnerability.

• 53:13Tim Ferriss?

  Perfect.

• 53:15Bill Gurley?

  So the first question is which books or books have you gifted the most? For me, it's Complexity about Santa Fe Institute and a wonderful book called Mr. China about this guy that lost his shirt, this British gentleman that lost his shirt investing in China. Those are my two. What are yours?

• 53:32Tim Ferriss?

  Okay, I would say the Moral Letters to Lucilius, better known, I'd say, through Penguin as Letters from a Stoic. These are letters of Seneca that I think are very, very easily applicable to many different situations. That would be one. Another one is Awareness by Anthony DeMello, a long since dead now, but Jesuit priest who is also a psychotherapist. Awareness and then I would say assorted poems, mostly of Hafiz.

• 54:00Bill Gurley?

  And you give these out?

• 54:02Tim Ferriss?

  I have bookshelves full of these books at home and I give them to friends and guests and so on.

• 54:09Bill Gurley?

  Very cool. The second question, which purchase of a hundred dollars or less has most positively impacted your life in the last six months? Now, I was hoping you were gonna ask me this question, but you didn't, so I was, I was ready for it. I have a very peculiar answer, like really, really amazing nail clippers. Like, pay fifty bucks for them or something, like it'd change your life, I promise.

• 54:34Tim Ferriss?

  I mean, you know, I could, I could use some, some, some manicure ink.

• 54:39Bill Gurley?

  Most of us use really shitty nail clippers. Wait till you try a really-

• 54:43Tim Ferriss?

  So a piece of advice from Kevin Kelly, just a quick one. He's like, you know that, you have that bad pen and that, that one bad pair of scissors? He's like, yeah, just get, get rid of all those bad pairs or versions of whatever. Like, actually get a high-quality version. So fingernail clippers, a hundred dollars or less, I would say, and this is not gonna be applicable to a lot of folks, I have Raynaud's disease, so my fingers and toes get brutally cold in the winter and really hot in the summer. Getting rid of ski gloves, I tried all the fanciest, including heated gloves, just getting bins without finger dividers and putting heaters, cheap disposable heaters-

• 55:19Bill Gurley?

  And don't worry about the fact that they might not look cool.

• 55:22Tim Ferriss?

  They don't look cool and they make- Everything else harder related to buckling, but I was in some really cold temperatures recently. So mittens, there you have it.

• 55:30Bill Gurley?

  Third is favorite failure or failure that set you up for success. I was thinking about this last night. So I was very fortunate and got introduced into math competitions in the sixth grade and was super successful. But by eighth grade, I was getting my head handed to me. And there was just a whole influx of new students and new people, a lot of immigrants, and it just got harder. And in retrospect, I think feeling the victory, but then having it kind of get away was very humbling and gave me a proper perspective on things.

• 56:12Tim Ferriss?

  Yeah, that makes sense. I would say, I already mentioned one, which would be the Four Hour Chef burning me out and also getting boycotted by a lot of retailers because it was the first major title out of Amazon Publishing at the time. And for that reason, even though it sold 120,000 copies in the first week, which is a lot. And I think number two on the New York Times list sold something like 10,000 copies. It ended up number four on New York Times, which is largely an editor's choice list. If you want a compiled list, something like the Wall Street Journal is a truer reflection of, say, Nielsen BooksCan. And that was very hard for me to stomach after also just doing this suicide run of cramming it into a year and a half,

• 56:57Tim Ferriss?

  which led to the podcast. If I had not burned out, podcast wouldn't have happened. I would add to that, flashing back much earlier, when I was initially an undergrad, I wanted to be a neuroscience. I was a neuroscience major and I couldn't do the animal testing required in the lab within which I wanted to work. And I think it's important. I do think actually this type of testing is important. I couldn't personally do it at the time and I switched to East Asian Studies with a focus on language acquisition. And without that obsessive focus on language and language acquisition, I don't think the fidelity of my hearing and awareness would be such that I could do my podcasting the way I do it.

• 57:35Bill Gurley?

  That's cool.

• 57:36Tim Ferriss?

  Yeah, I think that cultivated a sensitivity that helped much later. So, just to add a footnote to that, do whatever gives you the most energy because energy is that currency that drives everything else. So I don't regret majoring in East Asian Studies at all.

• 57:50Bill Gurley?

  The next one, you ask almost all of your guests about the gigantic billboard.

• 57:54Tim Ferriss?

  Yep.

• 57:55Bill Gurley?

  I just a few weeks ago said, "Don't be tribal." And I just feel like there's no reason that 50% of the world should have their opinion on everything decided by one group of people. And then I just think we all need to kind of be responsible for our own thinking. What's your answer to your own favorite question?

• 58:14Tim Ferriss?

  I'll piggyback on the thinking theme and I'm going to borrow mine from BJ Miller, hospice care physician, who he does a lot more, but he's helped thousands of people to die. And I had him on the podcast and his answer was, "Don't believe everything that you think," which ties into the Awareness book, Anthony DeMello I mentioned earlier. But don't believe everything that you think. I think many of our ills come from not cross-examining the things we take to be true.

• 58:41Bill Gurley?

  Fair. That correlates with that famous saying, "Strong opinions loosely held."

• 58:47Tim Ferriss?

  Indeed, yes.

• 58:48Bill Gurley?

  I think I might know your answer to this one. What is the best investment you've ever made? Mine's Uber. What's yours?

• 58:55Tim Ferriss?

  Yeah, we've got the startup, we've got the startup investments, but I'm going to actually, just to try to give a different answer, I'm going to say going to Blog Expo, I want to say it was, because that is where I met a ton of bloggers in person, including Robert Scoble, who ended up being very, very helpful and putting something on his blog that I think was a sort of a phase shift moment for the Four Hour Work Week. Because without any of that... None of the other stuff happens.

• 59:31Bill Gurley?

  Okay, and then I'll do this one last. In the last five years, what new belief, behavior, or habit has most improved your life? For me, I've learned that if you just wait a little bit of time, a lot of problems go away. And I used, I, I, I used to go deep in them. And this weekend was a perfect example, and this is a good transition to Silicon Valley Bank. But a lot of people did a lot of crazy manic things this weekend that didn't matter.

• 59:58Tim Ferriss?

  Yeah.

• 59:59Bill Gurley?

  Cause it all got solved this morning. So that's my, that's do nothing and wait. My new habit.

• 1:00:07Tim Ferriss?

  I would say mine is probably studying things like nonviolent communication. I encourage everybody, check it out. Get the audiobook by Marshall, I'm blanking on his last name. Learning how to navigate conflict well. And I don't think I was terrible at it before, but nonviolent communication. And also, pro tip, if you are so dysregulated, if you're just so amped up that no matter what, it doesn't matter which tools you have in your toolkit, because you're gonna blow it. You're allowed to say to someone, which comes back to kind of doing nothing. I really just don't think I'm in a place right now to have this conversation go well. So let's just take a little breather and maybe we can do this later this afternoon or some other time.

• 1:00:52Tim Ferriss?

  Just giving yourself permission to wait.

• 1:00:54Bill Gurley?

  We're out of time.

• 1:00:55Tim Ferriss?

  We're out of time. Bill Gurley.

• 1:00:57Bill Gurley?

  Tim Ferriss.

• 1:00:59Tim Ferriss?

  Thanks, everybody.

• 1:01:03Tim Ferriss?

  Hey guys, this is Tim again. Just one more thing before you take off, and that is Five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend? Between one and a half and two million people subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I've found or discovered or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums perhaps, gadgets.

• 1:01:39Tim Ferriss?

  Gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange esoteric things end up in my field and then I test them and then I share them with you. So if that sounds fun, again, it's very short, a little tiny bite of goodness before you head off for the weekend, something to think about. If you'd like to try it out, just go to tim.blog/friday, type that into your browser, tim.blog/friday, drop in your email and you'll get the very next one. Thanks for listening. This episode is brought to you by Eight Sleep. Temperature is one of the main causes of poor sleep and heat is my personal nemesis. I've suffered for decades tossing and turning, throwing blankets off, pulling the back on,

• 1:02:24Tim Ferriss?

  putting one leg on top and repeating all of that ad nauseam. But now I am falling asleep in record time. Why? Because I'm using a device that was recommended to me by friends called the Pod Cover by Eight Sleep. The Pod Cover fits on any mattress and allows you to adjust the temperature of your sleeping environment, providing the optimal temperature that gets you the best night's sleep. With the Pod Cover's dual-zone temperature control, you and your partner can set your sides of the bed to as cool as 55 degrees or as hot as 110 degrees. I think generally in my experience, my partners prefer the high side and I like to sleep very, very cool. So stop fighting, this helps. Based on your biometrics, environment and sleep stages, the Pod Cover makes temperature

• 1:03:06Tim Ferriss?

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• 1:03:41Tim Ferriss?

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• 1:04:26Tim Ferriss?

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