#410: Ryan Holiday — Turning the Tables

Ryan Holiday — Turning the Tables | Brought to you by LinkedIn Jobs https://linkedin.com/Tim and 99designs http://99designs.com/tim. Welcome to The Tim Ferriss Show http://tim.blog/podcast?utm_source=podcast&utm_medium=podcast&utm_campaign=podcast-description! It is — usually — my job to sit down with world-class performers of all different types to tease out the habits, routines, favorite books, and so on that you can apply and test in your own life. This time we have a "turning the tables" episode. What does that mean? Well, I will not be the one doing the interviewing. Instead, I will be the one being interviewed by my friend, Ryan Holiday. So who is this Ryan fella? Ryan Holiday (TW https://twitter.com/ryanholiday/IG https://www.instagram.com/ryanholiday/: @RyanHoliday https://twitter.com/ryanholiday) is one of the world's foremost thinkers and writers on ancient philosophy and its place in modern life. He is a sought-after speaker and strategist and the author of many bestselling books, including The Obstacle Is the Way https://www.amazon.com/Obstacle-Way-Timeless-Turning-Triumph/dp/B00K5JUNSU/?tag=offsitoftimfe-20, Ego Is the Enemy https://www.amazon.com/Tim-Ferriss-Audio-Ego-Enemy/dp/B01GSIZ9EY/?tag=offsitoftimfe-20, and The Daily Stoic https://www.amazon.com/Daily-Stoic-Meditations-Wisdom-Perseverance/dp/B01MA32SO0/?tag=offsitoftimfe-20. His books have been translated into more than 30 languages and have sold more than two million copies worldwide. He lives with his family outside of Austin, Texas. You can subscribe to receive his writing at RyanHoliday.net https://ryanholiday.net/ and DailyStoic.com https://dailystoic.com/. Ryan was also the fourth-ever guest https://tim.blog/2014/05/06/the-tim-ferriss-podcast-episode-4-ryan-holiday/ on the podcast in the very beginning, and he has written multiple popular guest posts https://tim.blog/2009/04/13/stoicism-101-a-practical-guide-for-entrepreneurs/ for my blog, which you can find at tim.blog. His latest book is Stillness Is the Key https://www.amazon.com/Stillness-Key-Ryan-Holiday/dp/0525538585/?tag=offsitoftimfe-20, which was an instant #1 New York Times bestseller and Wall Street Journal bestseller. I also recommend checking out the interview on YouTube, if you like, as I made sure to have video from multiple angles for this episode. Just go to youtube.com/timferriss http://youtube.com/timferriss. Please enjoy! This episode is brought to you by LinkedIn Jobs https://linkedin.com/Tim. Hiring can be hard, and it and be super expensive and painful if you get it wrong. Today, with more qualified candidates than ever — but also more noise than ever — employers need a hiring solution that helps them find the right people for their businesses. LinkedIn Jobs https://linkedin.com/Tim provides just that by screening candidates with the hard and soft skills you’re looking for so you can quickly find and hire the right person. LinkedIn can make sure your job post gets in front of people you want to hire — people with the skills, qualifications, and other insights that help LinkedIn paint a better picture of potential candidates. It’s no wonder great candidates are hired every eight seconds on LinkedIn. Find the right person meant for your business today with LinkedIn Jobs https://linkedin.com/Tim. You can pay what you want, and the first $50 is on LinkedIn. Just visit LinkedIn.com/Tim https://linkedin.com/Tim to get $50 off your first job post! Terms and conditions apply. This podcast is also brought to you by 99designs http://99designs.com/tim, the global creative platform that makes it easy for designers and clients to work together to create designs they love. Its creative process has become the go-to solution for businesses, agencies, and individuals, and I have used it for years to help with display advertising and illustrations and to rapid prototype the cover for The Tao of Seneca. Whether your business needs a logo, website design, business card, or anything you can imagine, check out 99designs http://99designs.com/tim. You can work with multiple designers at once to get a bunch of different ideas, or hire the perfect designer for your project based on their style and industry specialization. It's simple to review concepts and leave feedback so you'll end up with a design that you're happy with. Click this link and get $20 off plus a $99 upgrade http://99designs.com/tim. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts https://podcasts.apple.com/us/podcast/the-tim-ferriss-show/id863897795?mt=2/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. For show notes and past guests, please visit tim.blog/podcast https://tim.blog/podcast/?utm_source=podcast&utm_medium=podcast&utm_campaign=podcast-description. 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 http://tim.blog/transcripts. Interested in sponsoring the podcast? Please fill out the form at tim.blog/sponsor http://tim.blog/sponsor. Discover Tim’s books: tim.blog/books http://tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss https://twitter.com/tferriss Instagram: instagram.com/timferriss https://instagram.com/timferriss/ Facebook: facebook.com/timferriss https://www.facebook.com/TimFerriss/ YouTube: youtube.com/timferriss https://www.youtube.com/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/, and many more. 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• 0:01Tim Ferriss?

  At this altitude, I can run flat out for a half mile before my hands start shaking.

• 0:06Speaker 01

  Can I answer your personal question?

• 0:08Speaker 02

  Now would be an appropriate time.

• 0:12Speaker 01

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

• 0:24Tim Ferriss?

  This episode is brought to you by LinkedIn Jobs. Hiring can be hard, can be super, super expensive and very painful if you get it wrong. I certainly have had that experience multiple times, have made a lot of mistakes. I am not eager to repeat any of them. So I try to do as much vetting as possible now on the front end. Today, with more qualified candidates than ever, but certainly more noise than ever, employers need a hiring solution that helps them find the right people for their businesses without wasting time, without wasting money. LinkedIn Jobs provides just that. LinkedIn Jobs screens candidates with the hard and soft skills that you specify, that you're looking for, so you can quickly find and hire the right person. They also look beyond work skills, so collaboration, creativity, adaptability, to connect you with

• 1:09Tim Ferriss?

  candidates who match your business perfectly. They have endless business-specific data points that help them to massage this and that which can help you to find the best fit. LinkedIn can make sure your job post gets in front of people you want to hire, people with the skills, qualifications and other insights that help LinkedIn paint a better picture of potential candidates. It's no wonder that great candidates are hired every eight seconds on average on LinkedIn. That's pretty wild, every eight seconds. So find the right person meant for your business today with LinkedIn Jobs. You can pay what you want and the first $50 is on LinkedIn. Just visit LinkedIn.com/Tim for more details. Again, that's LinkedIn.com/Tim to get $50 off your first job post.

• 1:54Tim Ferriss?

  Let's check it out. LinkedIn.com/Tim. Terms and conditions do apply. 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.

• 2:34Tim Ferriss?

  You will get a free one year supply of vitamin D and five free AG1 travel packs with your first subscription purchase. So learn more, check it out. Go to drinkag1.com/tim. That's drink AG1, the number one. Drinkag1.com/tim. Last time, drinkag1.com/tim. Check it out.

• 3:00Tim Ferriss?

  This episode is brought to you by 99designs, the global creative platform that makes it easy for you to find and work with amazing graphic designers online. Longtime listeners of this podcast know how much attention I pay to detail, how obsessively I approach nearly all elements of my work because the small things often end up being the big things. So whether it's your logo, your business cards, website design, even your email templates, all of these visual elements tell your customers, tell your users who you are and what you're about. So I think it's worth sweating the details. I've been using 99designs for years now to ensure that many of my creative projects, whether big or small, are as cohesive, professional and beautiful as possible. I've worked on draft mockups of book covers. I've worked on all sorts of things.

• 3:45Tim Ferriss?

  Most recently, I've been working with a designer at 99designs to update the illustrations and layouts for all of my downloadable eBooks. I've developed a really great working relationship with the designer who goes by the username Spoonlancer and I intend to continue working with him to bring ideas to life, one project at a time. I've also used 99designs for all sorts of high end illustration for different books like the Tao of Seneca. You can see a bunch of examples on my Instagram that I've put up and they've turned out better than I possibly could have hoped. So from logos to websites to packaging to books. 99designs is the go-to creative resource to build your brand on any budget.

• 4:24Tim Ferriss?

  So check them out right now, my listeners, that's you guys can get $20 off plus a free $99 upgrade on their first design contest. Contest is a great way to get started and find the right designer for long-term work. You can also book a free design consultation with a brand expert at 99designs to receive personalized branding advice over the phone. Their hands-on team has helped thousands of business owners at this point. It's a great way to get the most out of your experience with 99designs. So, take a look. Head to 99designs.com/tim for your discount and to sign up for design consultation today. That's 99designs.com/tim.

• 5:04Tim Ferriss?

  Well, hello, boys and girls, muskets and squirrels. This is Tim Ferriss. Welcome to another episode of the Tim Ferriss Show. This is Tim Ferriss. As I think I may have already said, it is usually my job to sit down with world-class performers of all different types from different areas to tease out the habits, routines, quirks, books, and so on that you can apply and test in your own lives. This time, we have a turning the tables episode. What does that mean? It means I'm not doing the interviewing. Instead, I will be getting interviewed by my friend, Ryan Holiday. He and I wanted to get together, so we figured, why not record the entire thing? And who is this Ryan fellow, anyway? Ryan Holiday, on Twitter and Instagram, @RyanHoliday, is one of the world's foremost thinkers

• 5:46Tim Ferriss?

  and writers on ancient philosophy and its place in modern life. He's a sought-after speaker and strategist and author of many bestselling books, including the blockbuster, "The Obstacle is the Way," which has been used by many of the top coaches and competitors in the NFL, military, and elsewhere. "Ego is the Enemy," and "The Daily Stoic." His books have been translated into more than 30 languages and have sold more than 2 million copies worldwide. He lives with his family outside of Austin, Texas. You can subscribe and receive his writing at RyanHoliday.net. Does some really, really good reading list, recaps, and recommendations. And DailyStoic.com. Ryan was also the fourth-ever podcast guest on this podcast in the very, very beginning. So...

• 6:30Tim Ferriss?

  He's been along for the ride and he's written multiple popular guest posts for my blog, which you can all find at tim.blog, including Beginner's Guides to Stoic Philosophy, of course, which I have spoken about and written about a lot, including in the TED Talk, which can be found at tim.blog/ted. Ryan's latest book is Stillness is the Key, which was an instant number one New York Times Bestseller and Wall Street Journal Bestseller. I also recommend, if you'd like video, checking out the interview, this interview, on YouTube, since we captured video from multiple angles for this conversation. You can find that at youtube.com/timfaris, of course, with two R's and two S's as per always. Please enjoy.

• 7:17Ryan Holiday?

  I've known you for a long time and I was thinking one of the biggest changes that I've seen in you as a person came when you got your dog. And I remember you approached it in very Tim Ferriss fashion. You didn't just like, "Hey, like me, like I got a goat one day because we saw it on Craigslist and we just like went and got it." But that's not like the Tim Ferriss way.

• 7:37Tim Ferriss?

  Yeah.

• 7:37Ryan Holiday?

  You were like, you were talking, you talked to a bunch of people, you read a bunch of books, but you ultimately end up, was it 10 years ago you got a dog?

• 7:44Tim Ferriss?

  Four and a half years ago, maybe five.

• 7:47Ryan Holiday?

  But, but it's been an interesting pivot in your life. Why do you think it impacted you so much?

• 7:57Tim Ferriss?

  I think that there are a few aspects to it. Number one is caring for a puppy. At least if you do it well, takes your attention outside of any type of self-indulgent reflection slash obsessive-compulsive rumination.

• 8:17Ryan Holiday?

  Sure.

• 8:18Tim Ferriss?

  And as someone who has had a history of depression, which is being stuck in the past and I think being highly self-referential, I mean, depression is, I think, as someone who's experienced it a lot in life. Very self obsessive. Yeah. So when you have something in front of you that requires and demands care, or it's gonna pee on your carpet every two and a half hours, like Molly, my dog, it's incredibly antidepressive in that sense because it forces a complete refocus. I also, I think, realized very quickly how absurd some of my reactions are to things,

• 9:02Tim Ferriss?

  or have been historically, in the sense that

• 9:06Tim Ferriss?

  if you have a problem at work, you have a problem with your partner, your spouse, your girlfriend, boyfriend, you can get upset and sort of create an imaginary agenda that they have where they deliberately did A, B, or C to upset you. Sure. But with a dog, that's completely absurd. Like, at face value, it's completely absurd, right? So all the problems are your fault. It's your fault, right? So if your dog chews on your shoes, that's your fault. It's a dog and you left your shoes out. Right? So a big part of,

• 9:38Tim Ferriss?

  I think, raising a puppy well is making it extremely difficult to make mistakes that then become habits, right? That's, that's, that's an approach, or at least a lens through which you can look at raising a puppy. And if you don't want your dog to develop a taste for chewing on shoes, don't leave your shoes out. Right. Put them on something or in something that makes that impossible. And similarly, peeing in the house. To avoid that, use something like crate training. And so I think that when I became, particularly in the early periods of training Molly upset because she wouldn't follow my instructions. Yeah.

• 10:21Tim Ferriss?

  After an initial period of just getting upset, which I think was my default and has been a default for a long time. Anger has been a go to.

• 10:30Tim Ferriss?

  Emotion, which, you know, I think is, I think Krista Tippett once said, it's fear shown in public or something like that, which I tend to agree with on some level. Getting upset is fear shown in public? Getting angry. Yeah. Yep. And it's a coping mechanism. Some people shut down. Right. Some people learn to get angry. I learned to get angry, like when I was, when I was little. So. Doing that, though, with this dog who does not speak English, was so ridiculous and ineffective that I had to resort to doing other things that, lo and behold, translate to other people and even to yourself, like positive reinforcement.

• 11:06Ryan Holiday?

  Yeah.

• 11:06Tim Ferriss?

  Right? I didn't, through sports and coaching and teaching or receiving teaching, had a little bit of positive reinforcement, but not a whole lot.

• 11:16Ryan Holiday?

  Yeah.

• 11:16Tim Ferriss?

  And so I've learned to go without it, even though that is unhealthy.

• 11:19Ryan Holiday?

  Sure.

• 11:20Tim Ferriss?

  And reading about animal training, if you really want to take it seriously, if you look at, say, training marine mammals, like dolphins, you can't get pissed and hit it with a rolled-up newspaper. It doesn't work underwater, and they're faster than you are. So you have to figure out how to use like whistles and different clickers and means of marking the desired behavior and then rewarding.

• 11:42Ryan Holiday?

  Sure.

• 11:42Tim Ferriss?

  And getting into the habit of providing positive reinforcement, I think, led to me doing that more. I could still do it more with other people. And like how you treat other people, I think, impacts how you treat yourself and relate to yourself. So I think that those are all pieces of the puzzle. And then, last but not least,

• 12:05Tim Ferriss?

  feeling unconditional love, although granted...

• 12:10Ryan Holiday?

  Very conditional.

• 12:11Tim Ferriss?

  Giving your dog food and treats helps a lot.

• 12:13Ryan Holiday?

  Yeah.

• 12:14Tim Ferriss?

  But feeling this love from an animal and experiencing that in the absence of language, I think is really powerful.

• 12:25Ryan Holiday?

  Yeah.

• 12:26Tim Ferriss?

  As someone who tends to get tangled in their own inner voice in the form of language, to experience that type of deep, positive emotion and connection without language to trip over has been really impactful for me.

• 12:42Ryan Holiday?

  Do you think it was sort of giving you something to care about, like to be responsible for? That wasn't, there was, there's no...

• 12:52Ryan Holiday?

  There's no reason to have the dog. Like you have the dog because you love the dog. You know what I mean? Like you're not getting anything out of it in the sense of like, sure you have a nice car. You have to take care of the nice car, but you know what I mean?

• 13:04Tim Ferriss?

  I think so. I mean, you get a dog because you want a dog. It's in a sense, a very selfish act.

• 13:09Ryan Holiday?

  Yeah.

• 13:10Tim Ferriss?

  Even though you can adopt and do all these other things as I did with Molly that one would hope have some positive karmic impact, but ultimately you are choosing to have a dog.

• 13:19Ryan Holiday?

  Right.

• 13:20Tim Ferriss?

  Similarly, I think having kids is, this isn't a bad thing. It's not a value judgment, but like it is a selfish decision. Like you have kids because you want to have kids, right?

• 13:32Ryan Holiday?

  Yeah.

• 13:33Tim Ferriss?

  And I remember Mike Maples, who's this very well-known investor and friend of mine, said to me, he's like, rule number one with kids is like, they owe you nothing. Like their job is to receive love, not to give you love.

• 13:43Ryan Holiday?

  Yeah.

• 13:43Tim Ferriss?

  Because you decided to have the kids.

• 13:45Ryan Holiday?

  Right.

• 13:46Tim Ferriss?

  And I think that's true to dogs as well, or any type of pet. And for that reason, I do not recommend that everybody get dogs. Right? Because I think that for a lot of folks, as I felt for a really long time, I was too self-focused slash obsessed. And the only way I could see having a dog was to kind of wedge it into the open spaces that were left over. Once I had already

• 14:15Ryan Holiday?

  Sure.

• 14:15Tim Ferriss?

  executed on everything else I wanted to execute on or fixate on. And when I ended up getting Molly, I made the decision that I was going to actually reverse that and get Molly, prioritize, really taking good care of her, and then fit everything else around the dog.

• 14:32Ryan Holiday?

  Right.

• 14:32Tim Ferriss?

  And that's, those are two fundamentally different ways to look at it. And I think if you look at sort of the realm of behavior in humans and dogs, like most animals, including humans, are poorly trained.

• 14:47Ryan Holiday?

  Yeah.

• 14:48Tim Ferriss?

  And to do it well, takes a lot of effort and consistency. So if someone's ready for that, then I, I suggest, you know, adopting ideally, but otherwise I've, I've seen people who would, who get dogs and then just neglect them.

• 15:04Ryan Holiday?

  Sure.

• 15:04Tim Ferriss?

  Uh, and I'm conflicted as to how to feel about that. Cause on one hand, if they're rescuing a dog from a kill shelter.

• 15:12Ryan Holiday?

  Probably better.

• 15:13Tim Ferriss?

  Probably better. One could argue that's better. But I don't know. I'm not.

• 15:20Tim Ferriss?

  Yeah, I'm no professional ethicist, so.

• 15:22Ryan Holiday?

  No, there's a, there's a thing David Brooks talks about when his son was born. Someone sent him an email and said, this is his first kid, they said, you know, like, welcome to unavoidable reality. And the idea being that up until you're, up until then, sure, you have responsibilities as work and life, but like, pretty much anything you don't want to have to put up with, you don't have to put up with.

• 15:42Tim Ferriss?

  Right.

• 15:43Ryan Holiday?

  But as soon as you take on something like that, like with a kid, it's like, you think, okay, I'm gonna go to this thing at 1 o'clock. But if your kid falls asleep at 12:59, you're going to the thing when your kid wakes up.

• 15:56Tim Ferriss?

  Yeah.

• 15:56Ryan Holiday?

  And I think dogs have an element of that too. Suddenly you're responsible for this thing that is totally dependent on you.

• 16:01Tim Ferriss?

  No.

• 16:02Ryan Holiday?

  And the dog decides what the schedule is, not you, which if you're successful or self-absorbed, and they're kind of the same thing in different ways, it forces you to pivot your reality.

• 16:13Tim Ferriss?

  Yeah.

• 16:13Ryan Holiday?

  In a way that makes you a better person, I think.

• 16:16Tim Ferriss?

  I think so. And you develop, I don't, I don't really want to use the word patience. I think it's something else, maybe greater self-awareness and resilience in the face of the unpredictable.

• 16:31Ryan Holiday?

  Equanimity is what I think it is.

• 16:33Tim Ferriss?

  Equanimity, yeah. Equanimity we could use. Because it's like, all right, Molly gets sick, I'll give you an example, like, I remember one morning, I woke up to like, the most awful stench imaginable at like, 4:00 in the morning.

• 16:47Ryan Holiday?

  Right.

• 16:47Tim Ferriss?

  And I'm very protective of my sleep. Historically, they're, like, one of the best ways to get me really spun up and upset is to like, negatively affect my sleep.

• 16:58Ryan Holiday?

  Okay.

• 16:59Tim Ferriss?

  And it's like, 4:00 in the morning, went to bed at 1:00.

• 17:02Ryan Holiday?

  Yeah.

• 17:03Tim Ferriss?

  And it's the most horrible stench you can imagine. I wake up, I turn on the light, and Molly has just shit everywhere in the bedroom, including on the wall, which I thought was very impressive. I'm like.

• 17:11Ryan Holiday?

  Of course.

• 17:11Tim Ferriss?

  What possesses a dog to shit against the wall? I don't know. Nonetheless, it's like, all right, this is, like, this is what you're dealing with.

• 17:17Ryan Holiday?

  It's unavoidable reality.

• 17:19Tim Ferriss?

  Hour, two hours.

• 17:20Ryan Holiday?

  Right.

• 17:21Tim Ferriss?

  And putting on your hazmat gear and dealing with this. And I think you develop, or I have developed, to some extent, I don't think I'm the best at this, but the ability to put my, better put myself in other people's shoes.

• 17:36Ryan Holiday?

  Sure.

• 17:38Tim Ferriss?

  Because in a situation like that, it's clear to me Molly doesn't want to do what she's doing. Right, right. There's something that is- She's not gonna do this to ruin your sleep. She's not gonna do it to ruin my sleep. And it's not just unhelpful, but it's damaging to lose your, how's I gonna say, lose your shit. But to get really upset in a situation like that. It actually makes it harder to train your dog effectively. So the unavoidable reality piece, I think, is a big part of it. And I think there's something to be said for a phrase I heard recently.

• 18:21Tim Ferriss?

  This scientist I've come to know really well, when he had his first kid, and he had his first kid pretty late, by his standards, right? Yeah. He's a lot older than I am, so I'm like an 80-year-old when it comes to possible procreation these days. But he said, his brother, who had a few kids at that time, said, "Oh, welcome to the human race." When his first kid was born. Sure. And I do think that, it doesn't need to apply to everybody, but there is a certain self-absorption that is encouraged and fostered in modern life that I think is relatively new. Yeah. Does that make sense?

• 19:02Tim Ferriss?

  I mean, because we're, even in a densely populated city, you can be very physically isolated. And you don't have responsibilities or things to care for that for the vast majority of our evolution would have been commonplace. You don't have, like, you're not having kids at like 19 or 18. You don't live with your grandparents. Right, you don't live with your grandparents, you're not- Not hunting together. Hunting and gathering. Yeah. Where dogs would certainly have played a role, and did play a role. So I think that in some way, having a dog, or having a garden, or having kids,

• 19:45Tim Ferriss?

  these are all things we've evolved, sort of co-evolved with.

• 19:50Ryan Holiday?

  Totally.

• 19:50Tim Ferriss?

  And in the absence of that, you develop a lot of neuroses, which I was sort of the poster child for, for a really long time, and probably still am on some level, but less so.

• 19:59Ryan Holiday?

  No, I think that's really interesting. The idea of like, sort of consciously developing empathy is, and how almost you could argue that the way society is set up now consciously stunts the development of empathy. Like, the famous one, you're like, oh, you hear someone, it's like, how was your flight? And they're like, oh, it's terrible. I sat next to this like crying baby the whole time. Then you have kids, and you're like, you get on a plane, you hear a crying baby. You don't go, oh, there's a crying baby, this is bad for me. You go, that baby is upset. Like, it literally never occurred to you that the baby was crying because there's something wrong with the baby, and that this isn't fun for the baby, right? Or, and it's definitely not fun for the parent, like, they don't want it. So it's like, I think with dogs too, you like, you hear dog barking,

• 20:42Ryan Holiday?

  like, you hear about those, you're like, oh, I've been through that, or, oh, that's not fun for you. It sort of forces you, I think that's what they mean by that idea of welcome to the human race, not, welcome to the human race, you now have, like, you know, you're reproducing. It's welcome to the human race, you're no longer like a lone wolf. You like, understand, like, how, you understand what everyone else has been dealing with while you've been self-absorbed this entire time.

• 21:08Tim Ferriss?

  Yeah, it's sort of, like, welcome to the human slash hominid condition that was the norm for

• 21:16Ryan Holiday?

  Right.

• 21:17Tim Ferriss?

  Like, millennia

• 21:18Ryan Holiday?

  Yes.

• 21:19Tim Ferriss?

  Has been the norm. And, like, thank God you've snapped out of your aberrant strange behavior that is really kind of a new luxury.

• 21:28Ryan Holiday?

  Yeah, that's right. Have you felt like moving to Austin has had an impact on you in a similar way? Like, I feel like that there is also something selfish and strange about the New York life, or the San Francisco life, or the LA life. That I've just experienced the South and Texas and being a little bit different.

• 21:50Tim Ferriss?

  Yeah, well, Texas, the South and Austin are all.

• 21:53Ryan Holiday?

  A little different.

• 21:53Tim Ferriss?

  A little different, but I understand what you mean. I think that Austin has been so far, let's call it three years in, three, four years in, however long it is, has been very refreshing and rejuvenating in part. And this is coming back to your point about or observation about New York and LA and so on. In part because there is no one mono conversation.

• 22:21Ryan Holiday?

  Yeah.

• 22:21Tim Ferriss?

  And that could be seen as symptomatic of a huge benefit of living here or a huge drawback. Meaning there's certain, there's certain locations in the world like New York for finance. In New York, you have finance.

• 22:36Ryan Holiday?

  Yeah.

• 22:37Tim Ferriss?

  True in other places too, say London. If you want to be in the NBA All-Star Game of finance, it behooves you to go to one of those places. And as a result, it attracts people who are highly driven in certain fields, whether that's fashion, finance and so on. And as you've mentioned to me before, I think it's, there's a high correlation between self-absorption and professional success.

• 23:07Ryan Holiday?

  Yeah.

• 23:08Tim Ferriss?

  On some level.

• 23:08Ryan Holiday?

  It has to be.

• 23:09Tim Ferriss?

  And if you look at Los Angeles, even though Los Angeles is a huge, in reality, combination of different cities, entertainment is the predominant mono conversation. Whereas here in Austin, you have more of a medley.

• 23:30Ryan Holiday?

  Yeah.

• 23:31Tim Ferriss?

  And for that reason, I find it.

• 23:36Tim Ferriss?

  I find that I don't overtax a single sort of conversational track or part of my brain. Like you can quite easily hop from lily pad to lily pad and maintain some degree of mental dexterity, emotional dexterity. There's just, there's just more to easily dip your toe into here.

• 23:59Ryan Holiday?

  Yeah.

• 23:59Tim Ferriss?

  And it does exist in a place like San Francisco. But it takes more effort to avoid the mono conversations.

• 24:08Ryan Holiday?

  You know, you think one of the downsides of the mono conversation is also, let's call it mono thinking. Right? So I think, I think we have tended these days to define diversity as merely a function of race.

• 24:21Tim Ferriss?

  Yeah.

• 24:21Ryan Holiday?

  Or, or gender. But I think diversity as far as lifestyles, thinking, careers, interests, you know, is, is also super important.

• 24:34Tim Ferriss?

  The main downside of the mono conversation is mono thinking. And a group think that produces an echo chamber that, at least in my experience, doesn't stress test a lot of your own beliefs because you end up succumbing to this preaching to the choir.

• 24:56Ryan Holiday?

  Yeah.

• 24:57Tim Ferriss?

  And that, I think, is, I think is very dangerous.

• 25:05Ryan Holiday?

  Yeah.

• 25:05Tim Ferriss?

  I think it's very dangerous. I think in Silicon Valley where you have so much capital and so much power, so much culture shaping technology that you really want to have, not necessarily a court jester, but someone who can poke fun at the status quo.

• 25:25Ryan Holiday?

  Yeah.

• 25:25Tim Ferriss?

  And challenge deeply held beliefs, or I should say better yet, deeply assumed beliefs.

• 25:32Ryan Holiday?

  Yeah.

• 25:33Tim Ferriss?

  And that is very increasingly difficult to do in the Bay Area.

• 25:39Ryan Holiday?

  Yeah.

• 25:39Tim Ferriss?

  And in much of.

• 25:43Tim Ferriss?

  Certainly, culture in the United States. And we're in Austin, which is jokingly referred to as the blueberry and the tomato soup. Yeah, the blue dot in the red ocean. Yeah. And so it is, one might think that Austin is just a smaller version of San Francisco, but it's not. It's, you do have a mingling of political, artistic, and financial interests. Yes. That I deeply enjoy.

• 26:19Tim Ferriss?

  And the ability to easily, for instance, I mean, we're, we're sitting here right above a restaurant called Jeffries, and next door is Josephine House, and I had dinner at Josephine House with someone, I won't mention my name, most people wouldn't recognize him, but an extremely successful investor, financier, who came in from out of town, came in from elsewhere in Texas, very well educated, extremely smart, and also a sort of staunch Republican on many levels, not all levels, right? It's easy to paint with that broad brush.

• 27:01Tim Ferriss?

  And when you have the ability to sit down with someone like that easily here, it becomes harder to do what is so frequently done in San Francisco, as a place where I spent a lot of time, I mean, almost two decades in the Bay Area, to say, oh, right wingers are all knuckle dragging idiots. It becomes much more difficult to paint. Because you know by direct firsthand experience that that's not true. It's not that. It's not true in many cases, and it's just not that simple. Right. Right? It's just not that simple. And it forces you to contend with, I think, a mess of reality that it behooves all of us to recognize as messy. Yeah.

• 27:46Tim Ferriss?

  It just requires more thought. But I like the fact that it's, it's not as easy to kind of divide this country into like a left-right civil war. Yeah.

• 27:58Tim Ferriss?

  Of smart versus dumb, rich versus poor, this versus that. It's not that, it's not as easy to do here. And I like that.

• 28:06Ryan Holiday?

  Yeah.

• 28:07Tim Ferriss?

  I also think that it would be difficult for me to live in many places outside of Austin in Texas.

• 28:13Ryan Holiday?

  Sure.

• 28:14Tim Ferriss?

  Which is not a slight against Texas. It just means that Austin has a combination of factors. It's the combination of factors that makes it interesting to me. And the fact that it has some of the ingredients, and we'll see if this backfires over time, it might, but that made Silicon Valley Silicon Valley. You have, you have large, famous research universities with world-class talent from dozens of countries around the world. And it attracts a very intellectual crowd.

• 28:52Ryan Holiday?

  Yeah.

• 28:53Tim Ferriss?

  And as you and I know, there is an incredible writing scene here. There's some fantastic writers. And it has a lot of the ingredients I like about Silicon Valley without the sort of smug.

• 29:06Ryan Holiday?

  Yes.

• 29:07Tim Ferriss?

  Self-satisfaction that I find so unappetizing.

• 29:12Ryan Holiday?

  You know what I think's important when I was sort of like thinking about places to live is like, you're naturally a competitive person, the sort of keeping up with the Joneses part of it. Like, it's very easy for life to become an arms race, right? And when you live in a place with more diversity, where you live, where there's not sort of one industry or one scene that dominates all the others.

• 29:34Tim Ferriss?

  Yep.

• 29:34Ryan Holiday?

  You become more inwardly focused on what you want to do and what's important to you, rather than going, oh, did you hear what so-and-so just got?

• 29:42Tim Ferriss?

  Yeah.

• 29:43Ryan Holiday?

  You know, like, and I think that's a healthier way to live also.

• 29:46Tim Ferriss?

  Yeah, that's, I think that's a very good observation. There's no one lead dog to follow.

• 29:52Ryan Holiday?

  Yes.

• 29:53Tim Ferriss?

  Right? And. As a result, you have to make more conscious decisions about who you might want to emulate. It's not an immediate default.

• 30:04Ryan Holiday?

  Yeah.

• 30:05Tim Ferriss?

  And I like that. I also don't know if Austin would be the right place to live. It probably wouldn't for many industries if you are in your twenties and looking to cut your teeth.

• 30:17Ryan Holiday?

  Yeah.

• 30:17Tim Ferriss?

  And make your mark and kind of summit the mountain.

• 30:20Ryan Holiday?

  Sometimes you need that to drive you forward, but that maybe isn't how you want to spend your whole life.

• 30:26Tim Ferriss?

  Yeah, I think that there's a point, at least there was for me, where you've

• 30:34Tim Ferriss?

  you've basically alternated between park and sixth gear. And you're like, oh, wait, there are five other gears.

• 30:40Ryan Holiday?

  Yeah.

• 30:40Tim Ferriss?

  I don't actually need to have this binary lifestyle that is either like rest and recover or full out sprint for the Olympic gold medal. There are actually all of these gears in between that allow you to experience and enrich life in myriad other ways that were I geographically located in one of these no holds barred type A cities, I probably wouldn't give myself the slack in the system to discover. I would like to think it doesn't matter where I am.

• 31:18Ryan Holiday?

  Yeah.

• 31:19Tim Ferriss?

  I can cultivate all these amazing habits and types of awareness that will allow me to blah, blah, blah, blah, blah.

• 31:27Tim Ferriss?

  But the reality is

• 31:31Tim Ferriss?

  I'm highly flawed with all sorts of predispositions and I am, to my benefit and often to my detriment, highly, highly competitive.

• 31:41Ryan Holiday?

  Yeah.

• 31:41Tim Ferriss?

  So if I'm, if I'm thrown into any game, even if it's a stupid game that I shouldn't participate.

• 31:46Ryan Holiday?

  You want to win.

• 31:46Tim Ferriss?

  I'm gonna win. I'm gonna want to win. And recognizing that

• 31:52Tim Ferriss?

  is important. I remember having Peter Thiel on the podcast long ago.

• 31:57Ryan Holiday?

  I've listened, yeah.

• 31:58Tim Ferriss?

  Yeah. And I believe, I don't remember the context exactly, but one of the questions, and I'm paraphrasing here, I believe one of the questions he asks himself is, in what areas of my life can I be less competitive?

• 32:10Ryan Holiday?

  Yeah.

• 32:11Tim Ferriss?

  To be more satisfied or more content?

• 32:13Ryan Holiday?

  Yeah.

• 32:13Tim Ferriss?

  And If your default is competition,

• 32:21Tim Ferriss?

  I think it pays huge dividends to be aware of that and to ask those types of questions.

• 32:26Ryan Holiday?

  My favorite line from him is that competition is for losers.

• 32:28Tim Ferriss?

  Competition is for losers.

• 32:30Ryan Holiday?

  No, but I think what is interesting about you, though, is you are a very competitive person. And yet, and this is something I wrote down to ask you about, you have a habit of walking away from things that you're at the top of, right? So like, correct me if I'm wrong, but I think your decision to sort of stop angel investing or stop actively angel invest coincides with their decision to move to Austin or overlaps?

• 32:53Tim Ferriss?

  Yeah, very, very much an overlap. Yeah, 2015 and then surely thereafter.

• 32:58Ryan Holiday?

  So how much? What I'm curious about your decision to sort of, you know, you're not putting out a book a year, even though you could make a lot of money and sell a lot of copies. You sort of have been disciplined about what you don't do. But how much of that is also related to like designing a life or a day-to-day reality? You know, how much are they connected?

• 33:22Tim Ferriss?

  I think they are all really interrelated. And I'm not going to try to fabricate some grand master plan because I don't have one. But I do think that I tend to pause and try to reflect and ask a lot of questions when I feel that my decisions in any area of my life begin to bleed into fear of missing out or scarcity or fear-based decision-making.

• 33:56Tim Ferriss?

  Not perfect, but in the case of angel investing and the reason I stopped effectively all of it in 2015 or so is...

• 34:09Tim Ferriss?

  That I realized the conditions were becoming more difficult to place effective bets, especially as an individual using their own capital versus a fund with a nice like 2% management fee and 20% carry when you're using other limited partner money, which is a fine model. Sure. I don't have an ethical issue with it, but I realized that to do a good job with an increasingly, increasingly high number of DEX in the blackjack game. Yeah. In the form of bloated terms, higher prices, foreign capital flight from places like China coming into the US and affecting terms, I would either, I could no longer do an effective job part-time.

• 34:54Tim Ferriss?

  Yeah. And that I, if I wanted to continue to compete in that game, I would need to create a fund, do it semi-full-time, and in that world, I would be effectively replaceable. I would be in a long line of people trying to do the same thing. And that my drive to do that would be predominantly driven by fear of missing out and a, I think a sort of cortisol-driven scarcity mentality that is really fostered in the world of startups. Sure. And even if I were to win that game, I felt like the toll it would take would

• 35:36Tim Ferriss?

  not be worth the sort of Faustian bargain. Yeah. In other words, from a mental health perspective, from a physical health perspective, from an emotional health perspective, that, that it would, it would end poorly. And I tried to do, to make a realistic assessment of my track record in angel investing, which has been very good to date, but a lot of it's on paper. Yeah. And I began investing around 2008, 2009. I was like, okay, so if we flash forward, that's about six years. Many of these bets, and the jury's not out until the final. Till the wire transfer comes in. Till the wire transfer comes in.

• 36:17Tim Ferriss?

  And that final outcome for many of the startups that you bet on will take seven to 12 years. Yeah. So looking at that timeline, I thought to myself, well, I've placed between 50 and 70 bets. I'm not yet convinced that I'm good at this. So why would I? Commit to doing this full time if I'm not yet fully satisfied that I am good at this.

• 36:41Ryan Holiday?

  Right.

• 36:41Tim Ferriss?

  Or that things are sufficiently influenced by elements under my control that I can help steer outcomes.

• 36:50Ryan Holiday?

  Yeah.

• 36:50Tim Ferriss?

  Right? You could be the best at picking the initial horses, but by the end of the race, if they're falling apart, it doesn't make a difference. So these were all questions I thought about and that in addition to many other things, a very close friend of mine asking me to please not stop writing.

• 37:08Ryan Holiday?

  Yeah.

• 37:09Tim Ferriss?

  This is Kamal. Kamal Ravikant, great guy.

• 37:13Tim Ferriss?

  Given the feedback that he'd seen at events with readers of mine, he said, you'll never have that impact investing.

• 37:20Ryan Holiday?

  Right.

• 37:20Tim Ferriss?

  So please don't stop writing and those all then coincided when I asked many of those questions, which were uncomfortable because I've done very well financially in investing. I've done better in investing by far than I have in writing.

• 37:34Ryan Holiday?

  Well, certainly fields are more lucrative than other fields.

• 37:36Tim Ferriss?

  Yeah.

• 37:36Ryan Holiday?

  Sure. So not all success is created equal.

• 37:39Tim Ferriss?

  Yeah, for sure. And if you're, if you're trying to get rich, when people are like, I'm just gonna sell a few million copies of books. I'm like, God bless you. Good luck. Cause that is a really, it's difficult to make that math work.

• 37:50Ryan Holiday?

  Yeah.

• 37:51Tim Ferriss?

  There are far easier ways to make money. When I began to ask those questions, I realized that much of my being in the Bay Area was predicated on maintaining and building a competitive advantage in investing. So if you remove the investing.

• 38:06Ryan Holiday?

  Why am I here?

• 38:06Tim Ferriss?

  And you look at your surroundings with fresh eyes, you're like, well, wait a second. A lot of my best friends have left. So my social reasons for being here are few to none.

• 38:17Ryan Holiday?

  Yeah.

• 38:17Tim Ferriss?

  Not none, but a few.

• 38:21Tim Ferriss?

  If I remove the investing, my professional need to be here is non-existent.

• 38:26Ryan Holiday?

  Sure.

• 38:27Tim Ferriss?

  So why am I here?

• 38:28Ryan Holiday?

  Yeah.

• 38:29Tim Ferriss?

  What do I like? What do I dislike? And a lot went into the decision, but

• 38:35Tim Ferriss?

  led me to consider a number of different places, but predominantly Austin, which I'd wanted to move to right after college, just didn't get the job at Trilogy Software.

• 38:45Tim Ferriss?

  And if you look at some of these decisions, they're almost all catalyzed by a breakdown of some type.

• 38:54Ryan Holiday?

  Yeah.

• 38:54Tim Ferriss?

  Wearing out, some type of burnout.

• 38:56Ryan Holiday?

  Yeah.

• 38:56Tim Ferriss?

  That happened with the Four Hour Chef, leading to podcasting.

• 39:01Ryan Holiday?

  Yeah.

• 39:01Tim Ferriss?

  It just flamed out because I tried to do what should have been a three or four year project in a year or a year and a half, which was a suicide mission. And that, that extreme pain and burnout then led to test driving the podcast.

• 39:16Ryan Holiday?

  Right.

• 39:17Tim Ferriss?

  Right. So a lot of my walking away at the top, so to speak, I would like to say is this sort of grand philosophical insight and like balls of steel and.

• 39:28Ryan Holiday?

  You're not looking at the pile of chips and going, I have enough, let's walk away. You're actually going, this is awful and miserable.

• 39:34Tim Ferriss?

  It's often both.

• 39:35Ryan Holiday?

  Yes, right.

• 39:36Tim Ferriss?

  But it starts with this is awful and miserable.

• 39:38Ryan Holiday?

  Right.

• 39:38Tim Ferriss?

  So it's sort of the breakdown equals breakthrough. I'm borrowing that from someone that is catalyzed by wearing out.

• 39:47Ryan Holiday?

  Yeah.

• 39:48Tim Ferriss?

  And I suppose where I've been fortunate or made some good decisions is instead of just plowing through that, sometimes it's physically impossible. I will say I have enough chips where I don't need to race into the next decision. Let me take some time to journal, journal, journal, journal. And I do a lot of journal, journaling, asking questions. I don't find my thinking to be clear at all unless I'm writing.

• 40:12Ryan Holiday?

  Yeah.

• 40:13Tim Ferriss?

  And I think Kevin Kelly was the one who said this to me, amazing guy,

• 40:18Tim Ferriss?

  that he doesn't write to put his ideas down. He writes to think.

• 40:22Ryan Holiday?

  Yeah.

• 40:22Tim Ferriss?

  He writes as a means of thinking. And in doing that, I then have looked at options like stopping all angel investing.

• 40:31Ryan Holiday?

  Yeah.

• 40:32Tim Ferriss?

  I like to ask these absurd questions. What if I left the Bay Area entirely, moved to Austin, Texas? And I think that.

• 40:41Tim Ferriss?

  Another reason I've been comfortable pulling the trigger on a lot of these things, trying the podcast, is that I view them all as, and I don't know why it seems, I don't know why I find this so easy, but a lot of people find it hard. I'm not sure why that is. I think it's practice predominantly. Like, what would, what would a meaningful but reversible experiment look like? That's it.

• 41:06Ryan Holiday?

  Yeah.

• 41:06Tim Ferriss?

  Okay, with the podcast, I committed to, I think it was six episodes.

• 41:09Ryan Holiday?

  Yeah.

• 41:09Tim Ferriss?

  And if I don't like it, I can walk. That's, that's it. And with Austin, it's like, you can always, I can always move back to the Bay Area.

• 41:16Ryan Holiday?

  Yeah.

• 41:16Tim Ferriss?

  If my realization is, oh my God, I didn't realize how much I loved these things I now miss. I can always move back. It's, it's completely reversible.

• 41:25Ryan Holiday?

  I think it's a great, because I remember I was asking you recently for some advice on something. It was like sort of a big purchase. It would be a big lifestyle transition. And you were like, well, how else are you going to find out if you want to do it or not? And you said, like, why don't you just commit to doing it for two years? And, and that's totally right. Because I remember when I dropped out of college, I was, it's like, I'm dropping out of college. This is the biggest decision I've ever made in my life.

• 41:47Tim Ferriss?

  Yeah.

• 41:47Ryan Holiday?

  I remember I went to someone, they're like, you know, you can go back, right? And it like, it didn't even occur, like, even when I went to drop out, I was like, I'm here to drop out. And they were like, you, there's not a form for that. There's a take a semester off form. You know, but we think these lifestyle decisions are irrevocable and life altering. And really, they can start very small.

• 42:09Tim Ferriss?

  They can start really small. And I want to just highlight something you just said, which, which I think gets missed oftentimes in the romanticizing about dropping out

• 42:19Ryan Holiday?

  Yeah.

• 42:20Tim Ferriss?

  of college, that for many of the folks who are like the name brand titans, who have, who have adopted dropping out of college as One of their favorite stories and drums to beat. If you have the Zuckerbergs, the Teals, or whoever it might be, although Teal's not a great example of dropping out himself, but you talk about these incredible icons of entrepreneurship who dropped out of school. It's really important to realize that when you drop out of Harvard or Stanford, those administrations effectively say, "Come back anytime you want."

• 42:59Ryan Holiday?

  Yeah.

• 43:00Tim Ferriss?

  And that is a really important footnote that people need to be.

• 43:07Ryan Holiday?

  Yeah, although what I would add to that is I actually think the Zuckerbergs and the Gates are proof of the experimenting thing, right? Because I hear from people who want to drop out of college all the time. They're like, "I'd like to be an entrepreneur. I want to drop out of college." Mark Zuckerberg left college because Facebook was successful.

• 43:22Tim Ferriss?

  Right.

• 43:23Ryan Holiday?

  Right? He wasn't dropping out of college to then go start the Facebook.

• 43:26Tim Ferriss?

  Yeah.

• 43:27Ryan Holiday?

  And so you can do the thing now, and then if it's working, you can transition away. You can decide to go, "Hey, what would it look like if I committed full-time to this for six months? What would come of that?" And I think it's not like you've never been to Austin before and you sold everything you own and you were like, "I'm gonna see if I like it." Like, you can experiment. You dip your toe in these things in a bunch of different ways. And then, yeah, you are jumping off a cliff, but there's also an exit strategy.

• 43:55Tim Ferriss?

  Yeah, I almost never burn the ships.

• 43:59Ryan Holiday?

  Yeah.

• 44:00Tim Ferriss?

  I can't think of offhand a single example of me burning the ships and throwing caution to the wind and just leaping into the unknown. That's just not how I do things.

• 44:08Ryan Holiday?

  It's also because you don't need to do them. Like, I think you don't need to do that.

• 44:13Tim Ferriss?

  And by you, I think that means most people. Like, most people should not sort of jump headfirst into the shallow end and hope that they figure it out. I think that's a terrible idea. And if you look at some of the entrepreneurs who are thought of as these swashbuckling risk-takers, Richard Branson, Sir Richard Branson, I've had on the podcast.

• 44:34Tim Ferriss?

  As one example, they're actually, when you peek under the hood and start looking at the details, they are better called experts in risk mitigation and capping the downside.

• 44:46Ryan Holiday?

  Yeah.

• 44:46Tim Ferriss?

  Like, he figured out how to lease planes, I think from Boeing, might have been Airbus, for Virgin Atlantic.

• 44:52Ryan Holiday?

  Yeah.

• 44:52Tim Ferriss?

  And set up a structure such that the financial risks usually associated with airlines were dramatically mitigated.

• 45:00Ryan Holiday?

  Yes.

• 45:01Tim Ferriss?

  And he made a lot of exciting, unusual bets, most of which were survivable bets.

• 45:09Ryan Holiday?

  Yeah.

• 45:10Tim Ferriss?

  Right?

• 45:10Ryan Holiday?

  Yeah, Jeff Bezos says, "I don't believe in bet the company bets."

• 45:14Tim Ferriss?

  Yeah.

• 45:14Ryan Holiday?

  He's like, "I want to be constantly taking risks, small risks, that are survivable. I don't want the, if this doesn't work, we go out of business risk." He's like, "You've waited too long if you have to take those risks."

• 45:26Tim Ferriss?

  Yeah. And as you mentioned with Austin, I mean, I'd been to Austin 15 times.

• 45:32Ryan Holiday?

  Yeah.

• 45:32Tim Ferriss?

  I had spent increasingly long periods of time here, each trip to South by Southwest. So I had already done more than dipped my toe in the water.

• 45:41Ryan Holiday?

  Yeah.

• 45:42Tim Ferriss?

  And it was really a question of whether I would enjoy living here. I knew I enjoyed being here.

• 45:45Ryan Holiday?

  Yeah, right.

• 45:46Tim Ferriss?

  For short periods of time. Would I enjoy living here, which is a whole separate question. And there are ways to test.

• 45:52Ryan Holiday?

  Yes.

• 45:52Tim Ferriss?

  So I think my comfort with walking away at the top is a result of a high degree of comfort with and a large amount of practice in thinking about my life as a series of experiments.

• 46:11Ryan Holiday?

  Yeah.

• 46:12Tim Ferriss?

  And it's, it's also just being a student of recent history, right? Look at Dave Chappelle. He's like, "He's crazy. He walked away from 50 million or whatever." And then he comes back and he does, I don't know what the numbers are exactly, what, 100 million dollars with Netflix?

• 46:29Ryan Holiday?

  Yeah.

• 46:29Tim Ferriss?

  Dave Chappelle's fine.

• 46:30Ryan Holiday?

  Yeah, sure.

• 46:31Tim Ferriss?

  And people who really focus on being good at their craft can almost always come back. No one, I can't remember who said this, this was in Tribe Mentors, but someone said, you know, "If Will Smith doesn't do a movie for two years, people aren't like, 'Whatever happened to Will Smith?'"

• 46:48Ryan Holiday?

  Right, sure.

• 46:48Tim Ferriss?

  Like, Will Smith can take all the time he wants.

• 46:50Ryan Holiday?

  Yeah.

• 46:51Tim Ferriss?

  And I think that underscores...

• 46:57Tim Ferriss?

  The importance of just focusing on being as good as possible at your craft.

• 47:04Ryan Holiday?

  Yeah, that's the Cal Newport thing. Like, if you're so good, they can't ignore you. You get to dictate your terms.

• 47:09Tim Ferriss?

  Yeah, yeah. And I am extremely risk averse. Risk defined as something with a with a high likelihood of an irreversible outcome.

• 47:22Ryan Holiday?

  Yeah.

• 47:24Tim Ferriss?

  The bet the farm.

• 47:26Ryan Holiday?

  Yeah. So do you have any strategies for mitigating? Like, if you're thinking about doing something, what do you look at to sort of separate good risk and bad risk?

• 47:35Tim Ferriss?

  Good risk for me has a few characteristics. Two of the key characteristics would be

• 47:45Tim Ferriss?

  high, high 90 plus percent likelihood of developing, developing or deepening skills that will transfer to other things.

• 47:53Ryan Holiday?

  Okay.

• 47:54Tim Ferriss?

  Whether now or in the future, even if this project fails.

• 48:00Tim Ferriss?

  Another characteristic of good risk would be developing relationships that can transcend this project.

• 48:09Ryan Holiday?

  Yeah.

• 48:10Tim Ferriss?

  Even if it fails. And this is borrowing from Scott Adams quite a bit, the creator of Dilbert, who talks a lot about this type of thing. How to win even if a project fails. Another characteristic of good stress would be something that will help me to develop attributes or emotional resilience.

• 48:29Tim Ferriss?

  Or to take things less seriously, which I think often go together.

• 48:33Ryan Holiday?

  Yeah.

• 48:34Tim Ferriss?

  To try something that is scary to me or to most people that I can demystify in such a way that it's less intimidating.

• 48:42Ryan Holiday?

  Yeah.

• 48:42Tim Ferriss?

  Right? The podcasting and doing six episodes is a great example.

• 48:44Ryan Holiday?

  Yeah.

• 48:45Tim Ferriss?

  So in the beginning, the idea of podcasting in my head was having this big studio and all this equipment. And it's This American Life with a staff of 40 people. And no, it's not. After doing six episodes, like, oh, all right, actually, I'm not scared.

• 48:57Ryan Holiday?

  Sure.

• 48:57Tim Ferriss?

  By audio at all.

• 48:58Ryan Holiday?

  Yeah.

• 49:00Tim Ferriss?

  These mics, these cables and the recorder that's on this chair.

• 49:03Ryan Holiday?

  Yeah.

• 49:03Tim Ferriss?

  Like 500 bucks and you're

• 49:05Ryan Holiday?

  Right.

• 49:05Tim Ferriss?

  Locked and loaded. And the editing is actually pretty straightforward. So those are three characters of of good risk. And then

• 49:15Tim Ferriss?

  Bad risk, I think, is largely a function of allowing unknowns that don't need to be unknowns. And so I do a lot of homework for many of my bets. If I'm looking at, say, Austin, I want to understand what the landscape, political, legal, and so on, looks like in Austin. I want to look at population growth. I want to look at employment growth.

• 49:41Ryan Holiday?

  Yeah.

• 49:41Tim Ferriss?

  I want to look at median home costs.

• 49:44Ryan Holiday?

  Yeah.

• 49:45Tim Ferriss?

  And how prices are moving, not just in Austin, but compared to my other options on the table.

• 49:52Ryan Holiday?

  So the opportunity cost of the decision.

• 49:54Tim Ferriss?

  It's a relative decision. It's not an absolute decision.

• 49:56Ryan Holiday?

  Yeah.

• 49:57Tim Ferriss?

  Because, and I'm also going to look at, let's say, if I stay in San Francisco, what are, what are the risks of the status quo?

• 50:09Ryan Holiday?

  Yeah.

• 50:09Tim Ferriss?

  Like, what are the knowns that I dislike? And then what are the possible changes that I might dislike? So not just looking at the, the potential upside and downside and pros and cons of the new option, but comparing it to the current option. That sounds so self-evident, but it is not common practice, right? Most people just assume, all right, this is my known, and I'm going to look at the risks and pros and cons of this new option. I'm always looking at relative. I'm looking at not just opportunity cost, but the sort of relative attractiveness, right? And that can apply to just about anything. I mean, it can, it can apply to startups, certainly.

• 50:51Tim Ferriss?

  And the, in terms of bad risk, I, I do look at financial risk. I look at reputational risk. I look at legal liability risk and

• 51:11Tim Ferriss?

  I do, I do, I do more comprehensive risk assessment than I do opportunity assessment. In part because I want to look for asymmetric

• 51:24Ryan Holiday?

  Sure.

• 51:24Tim Ferriss?

  bets in the sense that if I know I can cap my downside, that there is little or I can manage or completely eliminate reputational legal risk by asking for, let's say, an indemnity clause and having a written record of what we agree my responsibilities will or will not be, and I'm putting in $50,000.

• 51:47Ryan Holiday?

  Yeah.

• 51:48Tim Ferriss?

  In a sense, if I can control my time that is allocated to this, my max downside risk is 50%.

• 51:54Ryan Holiday?

  Right.

• 51:54Tim Ferriss?

  But if I'm investing in software as a service.

• 51:57Ryan Holiday?

  It's 50,000.

• 51:58Tim Ferriss?

  Sorry, $50,000. If though, I'm investing in a sector, in a vertical, in a type of company like software as a service or whatever, that has comparables which show 100x returns, 1,000x returns, I'll take that bet all day long.

• 52:15Ryan Holiday?

  Yeah.

• 52:16Tim Ferriss?

  Right? If the team and so on.

• 52:18Ryan Holiday?

  Sure.

• 52:18Tim Ferriss?

  Give it a reasonable likelihood of success, that is a great asymmetric bet. And I think you can do that outside of investing in startups. I think investing helps to hone the questions you ask and the types of lens through which you look at things and how you might consider arbitrage and so on. But Austin for me is a very, it's a very simple bet where it's easy to cap the downside.

• 52:49Ryan Holiday?

  It seems to me that's the main strategy in your life is capping downside. So it's like, okay, you put $50,000 in the startup, the most you can lose is 50,000. You spend $500,000 on a real estate investment, you're responsible for the cost of maintaining the property, like it's a totally different. And so, and I think that that explains your experiment thing. So it's not, I'm starting a podcast, now I have to have a podcast forever. You're thinking, I'm committing to six. So the most, if I don't like it, the most I have to do is six episodes of something I don't like.

• 53:27Tim Ferriss?

  Yeah.

• 53:27Ryan Holiday?

  Do you know what I mean? You're, you're capping, you're capping, so it's not endless amounts of losses, whether that's time, resources, happiness, money.

• 53:36Tim Ferriss?

  Yeah. And I always try to cultivate walkaway power with my own projects.

• 53:48Ryan Holiday?

  How do you do that?

• 53:50Tim Ferriss?

  I'll explain or try to explain why I think it's important first. If if I feel like I have to do something, you lose your optionality.

• 54:00Ryan Holiday?

  Yeah.

• 54:01Tim Ferriss?

  And furthermore, you begin to make decisions out of fear or guilt, which in my experience, turn out, almost always turn out poorly.

• 54:10Ryan Holiday?

  Yeah.

• 54:12Tim Ferriss?

  Similar, if you're making decisions out of prestige, can turn out very poorly. I think I borrowed that from Maria Popova and what she said once on the podcast. But cultivating walkaway power is a function for me of

• 54:29Tim Ferriss?

  A, revisiting how little you actually need frequently.

• 54:35Ryan Holiday?

  Yep. This is Seneca.

• 54:38Tim Ferriss?

  Yeah, Seneca, not Timor's paupers huts, but you know, I will set aside a certain number of days each month or whatever it is to get by with the scantest, scantest or scantiest, I always mess that up, affair. But practicing periods of poverty or

• 54:58Ryan Holiday?

  It's like being okay with a rock bottom.

• 55:00Tim Ferriss?

  Yeah, making do, I just did this last week, a making do for a while with just like instant coffee and oatmeal in a bag that you cook with boiling water.

• 55:11Ryan Holiday?

  Yeah.

• 55:12Tim Ferriss?

  And everything's great. And granted, it's different when you do it for an extended period of time. It's different if that's your only option. But nonetheless, constantly revisiting and confirming how little is actually needed is number one. Number two is doing fear setting, this exercise that I talk quite a lot about, which is of course borrowed directly from stoicism and cognitive behavioral therapy, which is also largely based on Stoic philosophy of

• 55:45Tim Ferriss?

  What is the term in Latin? It is meditate.

• 55:50Ryan Holiday?

  Oh, premeditatio malorum.

• 55:52Tim Ferriss?

  Yeah, meditatio malorum. Meditating on the possible evils or risks. So I have a written format, fear setting. People can check out tim.blog forward slash TED if you want to see what that looks like. It's all free. I do that routinely. So we're recording this in January 2020. And I did a lot of fear setting around.

• 56:14Ryan Holiday?

  Us talking, how poorly this could go.

• 56:16Tim Ferriss?

  How poorly this conversation with Ryan could go and how I would possibly repair the incredible reputational damage. Around stopping just about everything. So even though I'm not seriously considering, or do I feel compelled to say, stop? Stopping the podcast. I would write down like, stop the podcast? Question mark. What if I stop this? What if I stop all involvement with real estate? What if I stopped all travel?

• 56:42Ryan Holiday?

  Sure.

• 56:42Tim Ferriss?

  What if I stopped? And now I will go through the thought experiment of what if I completely stopped these various things categorically? And when you run through the kind of so what, so what, so what, so what? For each of those, ultimately you realize you're going to be fucking fine.

• 57:02Ryan Holiday?

  Yeah.

• 57:02Tim Ferriss?

  With all of them.

• 57:03Ryan Holiday?

  Sure.

• 57:03Tim Ferriss?

  And to that extent, I think that making good decisions is often negotiating with yourself. And that the person you want to have win that negotiation, and this is advice I got a long time ago, is the person who cares the least. And that's not a value judgment. If you have two people negotiating against each other and one feels like they have to do the deal.

• 57:35Ryan Holiday?

  Yeah.

• 57:36Tim Ferriss?

  And the other person has a, has 20 different battness, right? Best alternative to negotiated agreement. And they don't give two shits whether the deal happens or not, or at the very least, they're very comfortable walking away.

• 57:49Ryan Holiday?

  Yeah.

• 57:50Tim Ferriss?

  He or she who cares the least wins.

• 57:51Ryan Holiday?

  Yeah.

• 57:52Tim Ferriss?

  And I like to cultivate the side of me that can see how little.

• 58:02Tim Ferriss?

  A lot of the glossy veneer aspects of life add at the end of the day to like the core of what you need to feel content on a regular basis. So that might be a lot of word salad at once, but those are at least some of the ways that I think about it.

• 58:21Ryan Holiday?

  No, I think that ties into, we were just talking about the Stoics, Marcus really says this thing. He says like, ask yourself at every moment, is this necessary? Like what you're thinking, what you're doing, what you're desiring, is this necessary? And that seems, you used to have a sign in your house that said like, simplify.

• 58:37Tim Ferriss?

  Still have it.

• 58:37Ryan Holiday?

  Yeah, that seems like you guys are in alignment. You're like, do I need this? Do I want this? What would happen if I didn't have it? Why does everyone else want it? It seems like you're constantly questioning that.

• 58:49Tim Ferriss?

  I am, or I try to do it at regular intervals. I mean, I get caught up in the slow stream and start swimming against the riptide all the time. I mean, I get sucked into stuff all the time, but I do very frequently take plane rides and so on to journal. And to also try to identify, this is relatively new, I mean, in the last few years, but especially crossing 2020 and looking at not just 2019, but the last decade.

• 59:25Ryan Holiday?

  Yeah.

• 59:26Tim Ferriss?

  And the better decisions that I had made and the poorer decisions that I'd made, which are different from good and bad outcomes.

• 59:40Ryan Holiday?

  Yeah, right.

• 59:41Tim Ferriss?

  But just the, so where I made mistakes in decision making and some of the catastrophes and things that really caused me a lot of angst and upset. One of the corollaries to the bad decisions is that

• 1:00:06Tim Ferriss?

  Or correlations or others that I wasn't paying attention to energetic management or like energy management and I'll explain what I mean by that.

• 1:00:17Ryan Holiday?

  Managing your own energy?

• 1:00:19Tim Ferriss?

  Yeah, it's pretty simple. I mean, as I get older, I'm still feel like I'm in good shape. But if I don't sleep well for two or three nights, life is not good.

• 1:00:29Ryan Holiday?

  Right.

• 1:00:29Tim Ferriss?

  Generally.

• 1:00:30Ryan Holiday?

  Right.

• 1:00:30Tim Ferriss?

  And that's a really simple example, but the, the point being when I'm considering doing a project, partnering with someone, embarking on some type of creative endeavor. The, the question that I'm trying to ask myself now is over the intermediate or long term, which to me could be three months.

• 1:00:52Ryan Holiday?

  Yeah.

• 1:00:53Tim Ferriss?

  Will this give me more energy or take away or deplete me of more energy?

• 1:00:58Ryan Holiday?

  Sure.

• 1:00:59Tim Ferriss?

  And.

• 1:01:00Ryan Holiday?

  So it's not like the hell yes or hell no. It's like, what does this do to my energy levels?

• 1:01:05Tim Ferriss?

  Yeah, which are, which are closely related, but it's, but some of, some of the things that give me a lot of energy are not necessarily a hell yes.

• 1:01:14Ryan Holiday?

  Right.

• 1:01:15Tim Ferriss?

  They're a yes, like swimming regularly.

• 1:01:17Ryan Holiday?

  Yeah. This is a great town for that.

• 1:01:19Tim Ferriss?

  It is a great town for that. Yeah. Yeah. You love Barton Springs.

• 1:01:22Ryan Holiday?

  Yeah.

• 1:01:23Tim Ferriss?

  It's a great, great location. There are a lot of pools here. So swimming regularly, I always feel better and I always feel more energized. I feel more emotionally resilient.

• 1:01:33Ryan Holiday?

  Sure.

• 1:01:34Tim Ferriss?

  After swimming.

• 1:01:35Ryan Holiday?

  Yeah.

• 1:01:36Tim Ferriss?

  And it's not a hell yes, like for some people going to Burning Man for the first time or something. It's not that.

• 1:01:43Ryan Holiday?

  It's not like chocolate cake, hell yes.

• 1:01:45Tim Ferriss?

  No, it's not that, it's not that volume of like jump up and down on the table. Hell yes. But it is a great investment for building up energy reserves.

• 1:01:58Ryan Holiday?

  Yeah.

• 1:01:59Tim Ferriss?

  And so I've tried to make more and more decisions, keeping that in mind.

• 1:02:04Ryan Holiday?

  Yeah.

• 1:02:04Tim Ferriss?

  And turned down a lot of what on paper would look like fantastic opportunities because it will involve dealing with a huge bureaucracy, which I know is going to drain my batteries and historically has always drained my batteries. And it's like, you know, it's, it's, it is on paper a great opportunity, but this is going to take 10 times longer than it's spec'd out to take. And it's gonna be draining. And I would much rather do something smaller that doesn't have that effect on my energy, even though one could argue that this would be better for my career, whatever the hell that happens to be. I still don't know what the.

• 1:02:40Ryan Holiday?

  I think that's, I think a lot of, you were talking about the difference between good and bad decisions is not the same as good or bad outcomes. And so I think a lot of people make decisions, and I do this, but I have to counteract it. But we go like, is this gonna make me more or less money? Is this going to make me more or less famous? Is this gonna make me more or less successful? Is this gonna make me more or less interesting? We think about the outcomes. And, and often that outcome is very far in the future and very much, the, the decision isn't, it isn't like, if you do this, you are guaranteed X, you know? Or if you do this, you're guaranteed X. It's like, hey, if you continue to do this over and over again, you might get this thing in 20 years.

• 1:03:19Tim Ferriss?

  Yeah.

• 1:03:20Ryan Holiday?

  And I think one of the things I took from the four hour work week, and that I've gotten from you regularly, is you tend to think more about like, quality of life right now. So don't work a crappy job that you hate so in 50 years, you can retire and go to the beach. Think about what decisions you can make now that give you the access to the beach in the, in the intermediate or short, short term. So I tend to think more like.

• 1:03:44Tim Ferriss?

  As an experiment, right?

• 1:03:45Ryan Holiday?

  Yes.

• 1:03:45Tim Ferriss?

  Specifically.

• 1:03:46Ryan Holiday?

  Yes.

• 1:03:47Tim Ferriss?

  Because you may get.

• 1:03:47Ryan Holiday?

  You may hate the beach.

• 1:03:48Tim Ferriss?

  To the end of the line, you're like, oh shit, I actually don't like sailing.

• 1:03:51Ryan Holiday?

  Totally.

• 1:03:51Tim Ferriss?

  And this was my made up dream for 50 years, for which I sacrificed all these other things.

• 1:03:55Ryan Holiday?

  Yeah, so I think it's like, is this giving me like day to day, what I like more or less, you know? So that you're, you're, that's my version of the energy thing is like, am I having the time and the life that I want? Not, am I doing this so maybe I get that in the future? And it seems like, as a person who popularizes lifestyle design, that's kind of your core message. It's like, are you designing a life you actually like living in?

• 1:04:20Tim Ferriss?

  That is, that is a, I think, a huge piece of it. And if we wanted to parse that out even further, it's, it's really trying to cultivate an acute awareness of knowns and unknowns. And if you look at lifestyle design.

• 1:04:44Tim Ferriss?

  For people who aren't familiar with the term, so lifestyle design would effectively be a contrasting sort of philosophical lens through which to look at career and personal development that is juxtaposed with the kind of slave, save, retire, I am going to cash in my chips in 20, 30, 40 years that will then redeem this period of doing many things that I dislike doing. Right. Which is not to say you're always going to enjoy doing everything. Yeah. Right? Like, I don't know many people who love doing their taxes. Yeah. There are things that you need to do, but outside-

• 1:05:28Tim Ferriss?

  And no one gets exactly what they want when they're 20 years old. Right. You know what I mean? Like, you have to earn and build and invest. Yeah, there is a period of testing that goes on to determine where you are particularly adept, looking at, we don't have to rehash of the book, but suffice to say, there are ways that you can test the, and should test, the hypothesis that in X period of time, when I do Y, it is going to give me Z amount of pleasure that will make up for these decisions I'm making in the interim. That is a very, that is a theory that is contingent on many things being accurate.

• 1:06:13Tim Ferriss?

  Yeah. And in my experience, effective lifestyle design is effective testing and awareness. Investing is, for me at least, has been effective testing and developing keen awareness of things that most people don't pay attention to, or a lot of people don't pay attention to. So if we're looking at, for instance-

• 1:06:39Tim Ferriss?

  Living in New York City versus living in Austin. Someone might say, well, I'm just going to live here for another 10 years. I'm going to have these following promotions in my investment banking job. And then I'm going to move to Hudson Valley. I'm going to move to Santa Barbara. I'm going to move to and then live the good life.

• 1:06:56Ryan Holiday?

  Sure you will.

• 1:06:57Tim Ferriss?

  Right, yeah. So you that if that is your life plan, like let's spend some time

• 1:07:06Tim Ferriss?

  developing experiments to prove or disprove that before you dedicate the next 20 years to it. But people will very often spend more time planning their Memorial Day weekend than they will specking out tests.

• 1:07:19Ryan Holiday?

  Right.

• 1:07:19Tim Ferriss?

  So if you look at so A, is there anything in your historical record to suggest that you will be able to walk away from something like that?

• 1:07:28Ryan Holiday?

  Right.

• 1:07:28Tim Ferriss?

  Anything?

• 1:07:28Ryan Holiday?

  Yeah.

• 1:07:29Tim Ferriss?

  If you are type A, right? And by definition, in that circumstance, you're probably type A.

• 1:07:36Ryan Holiday?

  Yeah.

• 1:07:36Tim Ferriss?

  And

• 1:07:39Tim Ferriss?

  there are many, many, many, many faulty assumptions.

• 1:07:41Ryan Holiday?

  Yeah.

• 1:07:42Tim Ferriss?

  So I think that I

• 1:07:48Tim Ferriss?

  I am very, very accepting of the fact that there are many things I don't know. And there are many things that I take for granted. And there are many things that I don't see.

• 1:07:59Ryan Holiday?

  Yeah.

• 1:07:59Tim Ferriss?

  Therefore, I try, I spend a lot of my time developing experiments. And that's, that's my constant framework. Like, how can I be sure that I know X?

• 1:08:11Ryan Holiday?

  Yeah.

• 1:08:12Tim Ferriss?

  Which, you know, relates to in 2015, walking away from startup investing. So I was like, all right, if I look at the track record of these various companies, not only in my portfolio, but others, for the biggest wins, it's taking, if we're looking at, say, Shopify, Uber, et cetera, it's taken seven to 12 years to come to fruition. And your final tally is not known until you've liquidated all of your holdings effectively. I mean, it's a little more complicated than that, but not by much. So even though on paper and also in exits, it would, I could convince myself that I am good at this. And people tell me I'm good at this.

• 1:08:50Tim Ferriss?

  That remains to be seen.

• 1:08:53Ryan Holiday?

  Yeah.

• 1:08:53Tim Ferriss?

  Right? And so I stopped.

• 1:08:56Ryan Holiday?

  And the larger assumption, just because you're good at something does not mean you have to keep doing it for the rest of your life.

• 1:09:02Tim Ferriss?

  Yeah, there are many things I'm good at that I shouldn't do at all.

• 1:09:05Ryan Holiday?

  Yeah.

• 1:09:05Tim Ferriss?

  And it's, I think it's, it's, it's challenging for anyone, myself included, to shift gears. If you, if you're good at something, being rewarded for something, and yet you have this creeping dread that you no longer want to do it, that, that, that is a challenging situation for, I think, just about anyone, and certainly has been challenging for me, but the, the, the parachute, right? The, the safety net is realizing that for almost anything, you can leave and come back.

• 1:09:41Ryan Holiday?

  Yeah.

• 1:09:42Tim Ferriss?

  Almost anything. And I'm sure there are exceptions, but if we're talking about businesses and professional capacities and careers, if you are really good, that's a big.

• 1:09:59Ryan Holiday?

  That's the ultimate leverage.

• 1:10:00Tim Ferriss?

  That's, that is, that is a huge hurdle that you need to be able to pass. But if you are really good and dedicated to your craft or crafts, it could be a combination of, of unusual crafts, right?

• 1:10:13Ryan Holiday?

  Right.

• 1:10:13Tim Ferriss?

  You might be a quant who's also really good at writing, and then you have a newsletter.

• 1:10:16Ryan Holiday?

  Sure.

• 1:10:16Tim Ferriss?

  It could be an unusual combination of trades, like Warren Buffett in public speaking, a writer, or Jeff Bezos in writing, entrepreneurship, et cetera.

• 1:10:25Tim Ferriss?

  You can always come back.

• 1:10:26Ryan Holiday?

  Right.

• 1:10:27Tim Ferriss?

  Right. It's, so I try to keep that in mind in making a lot of my decisions.

• 1:10:32Ryan Holiday?

  You know what's interesting? It's like, you're taking it all very seriously, but then you're also not taking it that serious. So like, I, I was thinking, because we were talking about the Stokes more, like, one of the things that sort of weaves its way through, I think, the thinking you're, you're giving, and I know I gave you one of these, but the, the momentum more, like, like, part, one of the reasons you shouldn't do the thing for the rest of your life just because you're good at it, is that you only get one life. And one of the reasons I think you're always questioning the, it, it seems like part of your fear setting thing is like.

• 1:11:01Tim Ferriss?

  What if I die? Like, does any of this matter? Do you know what I mean? Yeah, the costs of inaction. Yeah. I think that thinking very carefully about the costs of inaction and telescoping out six months, 12 months, 18 months, you know, what effect does continuing to do what you do have on you and your loved ones from a financial, emotional, physical perspective? Right? Yeah. And I think about death all the time, and it's not a morbid, sullen exercise for me. It's, this becomes easier the older you get because friends start dying, family

• 1:11:44Tim Ferriss?

  members die, and you realize this is not an indefinite lease. Yes. You have... Or that it is a lease. You don't own it. Yeah, it is a lease. Yes. And that, having the, I don't want to call it time pressure, but awareness of that impermanence, for me, I find, this might sound strange, but like greatly encouraging because it drives a sense of urgency. Yeah. Or at least time sensitivity to a lot of my decisions. And so that's on one

• 1:12:25Tim Ferriss?

  hand, sort of prizing this fleeting, non-renewable resource that is time, and realizing that it doesn't matter how much money you're willing to pay on your deathbed, you're not going to be able to buy back more time. Right. And then simultaneously, I guess meditating is the best way to put it, or contemplating how little a lot of this matters, or all of it matters. Yeah. In so much as, you know, as Naval Ravikant once said to me, he's like, "Yeah, we're just a bunch of monkeys on a spinning rock." Mm-hmm.

• 1:13:00Tim Ferriss?

  Spending time, this is gonna sound so highfalutin', but whatever, reading about the cosmos or contemplating as, I believe it was Ed Cook, an incredible memory competitive champion and entrepreneur, memorizes his company, M E M R I S E, and coach, also writer, had said to me, and BJ Miller, who's a hospice care physician, I think, did something very similar, but they would look at, say, the stars and imagine that it's possible, and I'm not an astrophysicist, so maybe this isn't possible, but that it's

• 1:13:43Tim Ferriss?

  possible that the star you are seeing is in fact light that is hitting your eye from a star that no longer exists.

• 1:13:51Ryan Holiday?

  Yeah, right.

• 1:13:52Tim Ferriss?

  And to just sort of contemplate that when you're freaking out because you have some problem with AMEX.

• 1:13:58Ryan Holiday?

  Right.

• 1:13:59Tim Ferriss?

  Or there's some disagreement and it's like somebody bad mouthed you at work or whatever it is, you're like, okay.

• 1:14:09Ryan Holiday?

  Number one or number two on the New York Times Bestseller List, or, you know, all the things that we-

• 1:14:15Tim Ferriss?

  Who cares? All dust. As our friend Marcus would say, like, all dust. Nobody gives a shit.

• 1:14:21Ryan Holiday?

  Not even you in the future will give a shit.

• 1:14:24Tim Ferriss?

  Yeah, it's all going to be, it's just completely irrelevant. And so, holding those two in my mind has been a practice. And I do think about death a lot. And there was a person featured in, I think it was Tribe Mentors, Muneeb Ali, who's involved, very heavily involved with cryptocurrency, very, very smart guy, maybe better put blockchain, very smart guy. And- It's funny to me how certain things stick and certain things don't stick.

• 1:15:05Ryan Holiday?

  Yeah.

• 1:15:06Tim Ferriss?

  Or certain things have like a time release, right? So I read this and I was like, oh, that's interesting.

• 1:15:10Ryan Holiday?

  Yeah.

• 1:15:10Tim Ferriss?

  And then months later it resurfaced and I've thought about it a lot since, which was, he'll, he will routinely ask himself when he's overwhelmed or feeling scattered, how much would I pay to relive this experience like 20 years from now, 30 years from now, 40 years from now? And I'm paraphrasing, so it's not, not, not perfectly stated, but, and I think about that where I'll be, if I think about the experiences that I would pay the most for,

• 1:15:40Tim Ferriss?

  and I'm being honest with myself, it's, it's not the professional successes or the glamour shots. It's usually something very simple, like.

• 1:15:52Ryan Holiday?

  It's the moments of stillness and quiet and peace and relationships.

• 1:15:56Tim Ferriss?

  Waking up in bed with my girlfriend on a, like a beautiful sunny day and like patting the, patting the bed and having my dog jump up.

• 1:16:03Ryan Holiday?

  Right.

• 1:16:04Tim Ferriss?

  Having a little snuggle fest. It's very, it sounds so cheesy, like the 20-year-old Tim would just be vomiting all over himself right now. But nonetheless, 20-year-old Tim is a pretty miserable fuck. So I feel like I've improved on that front. And asking yourself like, all right, if I were 80 and like Molly has long since passed away, maybe my wife has passed away, how much would I pay for that?

• 1:16:30Ryan Holiday?

  Yeah.

• 1:16:30Tim Ferriss?

  Right? And that really, to me, is part and parcel of the valuing of time, these slivers of experience as more valuable than making a speculative decision about earning more in the future based on doing something that takes you away from those people.

• 1:16:52Ryan Holiday?

  Right. Or agreeing to something because you might get some honor or.

• 1:16:56Tim Ferriss?

  Mm-hmm. You know? I'll just add one more thing, which is I really think that even if you keep all your money in a mattress, studying good investors is worth a lot.

• 1:17:10Ryan Holiday?

  Yeah.

• 1:17:10Tim Ferriss?

  Not necessarily in financial return, but in temporal return, right? And like in, in, in how you think about time.

• 1:17:17Ryan Holiday?

  Yeah.

• 1:17:18Tim Ferriss?

  Because.

• 1:17:21Tim Ferriss?

  Humans overall are very sloppy. I'm no mathematician, so I'll put myself in the same category. When it comes to thinking about probabilities.

• 1:17:30Ryan Holiday?

  Yeah.

• 1:17:30Tim Ferriss?

  Like probabilistic thinking is not, it's not a strong suit for humans. And so you might hear like, oh my God, there's a room of 300 people and like, these two people have the same birthday. That's crazy.

• 1:17:43Ryan Holiday?

  Yeah.

• 1:17:43Tim Ferriss?

  But like mathematically speaking, it's not that crazy.

• 1:17:45Ryan Holiday?

  Right.

• 1:17:46Tim Ferriss?

  And in fact, at some point it becomes totally expected.

• 1:17:49Ryan Holiday?

  Yeah.

• 1:17:49Tim Ferriss?

  And similarly, developing a basic sort of mathematical literacy with respect to investing. So I think most people watching and listening to this will have, as I did, I mean, I stopped taking math in high school because I had one bad math teacher, even though I was good at it. I became totally turned off. My brother went on to get a PhD in stats. So and it was the same year. He had a good math teacher and I had one who was just a ballbuster. And you can see how we split in different directions, but I've, I have a deep seated insecurity when it comes to math. Nonetheless, studying, investing has helped me to develop

• 1:18:28Tim Ferriss?

  my understanding of certain concepts like expected value. So if you think that you are going to, you could make a hundred thousand dollars or a million dollars or $10,000 at what point in time?

• 1:18:44Tim Ferriss?

  Is making that decision in your mind actually worth 10, 100,000 or whatever it might be?

• 1:18:49Ryan Holiday?

  Yeah.

• 1:18:50Tim Ferriss?

  Well, it depends a lot on the probability of that happening.

• 1:18:53Ryan Holiday?

  Right.

• 1:18:53Tim Ferriss?

  And then you can do some basic multiplication and be like, all right, actually the expected value of that, given that it's low probability or 50% or 30% is instead of a hundred thousand dollars, it's actually worth $25,000.

• 1:19:05Ryan Holiday?

  Right.

• 1:19:06Tim Ferriss?

  That could very, very deeply influence how you make that decision.

• 1:19:10Ryan Holiday?

  Right.

• 1:19:10Tim Ferriss?

  About how you're going to spend your time over the next six to 12 months.

• 1:19:12Ryan Holiday?

  Right.

• 1:19:13Tim Ferriss?

  Right?

• 1:19:13Ryan Holiday?

  Sure.

• 1:19:13Tim Ferriss?

  Because if there's a sure bet, it's a $50,000 return, but it's 80, 90% likely to happen.

• 1:19:19Ryan Holiday?

  It's worth more.

• 1:19:20Tim Ferriss?

  It's worth more, right? If you're thinking about it in a structured way. And there are some really fun books on investing that don't necessarily touch on this exactly. One is called More Money Than God. It's about hedge fund investors. It's a super fun book. It's kind of like liar's poker, but instead of purely bonds, it's,

• 1:19:40Ryan Holiday?

  Yeah.

• 1:19:40Tim Ferriss?

  It's all sorts of different characters and types of investing. There are other books. I think there's one called How to Measure Anything. Which is worth taking a look at. That was recommended by co-founder of Zocdoc named Nick Ganju, who is a fantastic teacher, really, really good teacher. He's taught me a lot about music and math. Math is too scary. Just like how to think probabilistically. Because life is probabilities.

• 1:20:08Ryan Holiday?

  Yeah.

• 1:20:08Tim Ferriss?

  And whenever, for instance, and I'm dragging myself into the deep end a little bit here because I'm not a scientist, but if you if you look at science and studies, you will very this is another reason to become sort of probabilistically literate, is you'll be better able to separate fact from fiction and fact from hyperbole in medicine and science. People get so confused about these things and people end up dying and making bad decisions.

• 1:20:41Ryan Holiday?

  Right.

• 1:20:41Tim Ferriss?

  Choosing quacky doctors without this basic literacy. There's a great book called Bad Science.

• 1:20:47Ryan Holiday?

  Yeah.

• 1:20:48Tim Ferriss?

  By Ben Goldacre, that I recommend to everybody. I excerpted some of those chapters in the appendix of The Four Hour Body, because I think it's so important. But suffice to say, if someone says, "These studies prove X", it's not really true.

• 1:21:05Ryan Holiday?

  Right.

• 1:21:06Tim Ferriss?

  They suggest at a high probability.

• 1:21:08Ryan Holiday?

  They suggest for a very small sample size, it had a slightly greater than average probability that X, yeah.

• 1:21:17Tim Ferriss?

  And it could be an incredibly strong signal, but it is not 100% certainty. So.

• 1:21:23Ryan Holiday?

  It might never have been replicated.

• 1:21:24Tim Ferriss?

  It might never have been replicated. There could be experimenter bias. Who knows how tight the design was? And it changes how you relate to the world and decisions and opportunities and risks when you start thinking in terms of probabilities. Right? Because to remove all risk.

• 1:21:43Tim Ferriss?

  Is a fool's errand.

• 1:21:44Ryan Holiday?

  Yeah.

• 1:21:44Tim Ferriss?

  I spent a lot of time trying to do that and chasing that tail end of like the last, let's just call it 10% of risk, you could spend all your time 24 hours a day, every day, trying to do that and you would still not succeed, right? You just have to lock yourself in solitary confinement in the box.

• 1:22:00Ryan Holiday?

  Right.

• 1:22:01Tim Ferriss?

  It would be no life worth living, but this has been a real game changer for me, even though I don't, I don't do, I mean, I invest. Anyone who's alive invests. I think that's it. You are investing time, energy, capital, like you're choosing where to allocate resources.

• 1:22:19Tim Ferriss?

  But I read all these books on investing, or Think Twice is another one that's good, related to cognitive biases, not because I'm playing the stock market.

• 1:22:34Ryan Holiday?

  Yeah.

• 1:22:34Tim Ferriss?

  At all. That's not why I'm reading these books. I'm reading it because it helps me to think in a more structured way about

• 1:22:43Tim Ferriss?

  good decision making.

• 1:22:46Ryan Holiday?

  Yeah, I want to come back to the studying thing because I had a question for you, but I was, when we were talking about sort of happiness, money, young, old, Sep Kambar, who we both know.

• 1:22:57Tim Ferriss?

  Yeah, brilliant guy.

• 1:22:58Ryan Holiday?

  He did this massive study where he scraped all these blog posts about, like in social media posts about what people were saying. I think the book is I Feel Fine. This is like the result of the findings, but he was talking about how young people, when they say like, I feel happy, it tends to be followed with statements about accomplishments or activity. And as you get older, the statements drift steadily towards feelings of contentment or connectedness. And so we can make a lot of decisions. It's like, we know objectively that's where we're going to end up. That's what we're going to care about, but then we spend most of our lives focusing on piling up accomplishments. Do you know what I mean?

• 1:23:41Tim Ferriss?

  Yeah.

• 1:23:41Ryan Holiday?

  And sort of knowing, I think that idea of thinking about what you're going to care about, if you are lucky enough to be old, get old, is really important because it puts the things that feel important in perspective.

• 1:23:54Tim Ferriss?

  Yeah, it, Sep's an amazing computer scientist.

• 1:23:59Ryan Holiday?

  Yeah.

• 1:23:59Tim Ferriss?

  And just a sweet heart of mine.

• 1:24:03Tim Ferriss?

  And this, this.

• 1:24:07Tim Ferriss?

  Observation that you just made, that in younger years, let's just call it twenties and maybe thirties, or early thirties, I am happy, I'm doing great because, and then accomplishment. Yeah. Versus the contrast with connectedness and so on when older, raises a lot of interesting questions for me, right? So is it that, independent of how well someone does professionally, that that shift exists? Yeah. Or is it that those people who are being polled, happen to be at, say, Stanford, where Sepp has spent a lot of time? No, people aren't being polled, this is unsolicited statements that you make on social media.

• 1:24:52Tim Ferriss?

  Okay, I got it. So that answers that. But these, to me, the... It's important to me at least, to immediately not be a cynic, but to ask a lot of questions so I understand the nature of what is being implied, right? Yeah. Because could it be that the people who experience, or value connectedness in later years, sort of paid their dues, cut their teeth, and therefore they're like, alright, I'm on my second home, I have checked off all these wrongs on Maslow's hierarchy of needs. Sure. Great, now I can focus on self-actualization.

• 1:25:37Tim Ferriss?

  Or does it happen independently? I think, if I had to place a bet, I would imagine that it probably happens somewhat independently as you become more aware of your mortality. Yes, I think that's what it is. But, this is another facet that I think underscores how beneficial it is to study good investors, and that is, or good scientists, but it's, I think that investing has more sex appeal for a lot of people. The distinction between correlation and causation. Yeah. Right? And, or is there a third, is it possible there's a third or fourth factor? Yeah. That could be causal, or at least highly correlated, right?

• 1:26:20Tim Ferriss?

  So you might see an observational study of some type where...

• 1:26:26Tim Ferriss?

  Women who do yoga between the ages of this and this report a higher level of well-being and Yeah. lower blood pressure. Therefore, the headline in some Huffington Post is Yeah, wherever, right? Therefore, yoga decreases blood pressure. Right. Wait a second. Where was this done? Yeah. It's like, oh, San Diego. Okay. What's the median household income? Okay, what else are they doing? Oh, they're seeing, they have PPO instead of HMO and they're seeing some of the best doctors in the country. Oh, okay. All right. And you begin to realize how tricky it can be to establish a causation, right? Yeah.

• 1:27:06Tim Ferriss?

  But I don't find, at least the more I dig into this stuff, I find that more enriching and exciting than anything else. I know that it's frustrating because it means you can't rely on say, most media reports of scientific findings or studies to be accurate and the claims that are extrapolated, but at the same time, to me, what it highlights is how much there is in plain sight that is really misunderstood. Yeah. And that's exciting for me because to me, that says, that spells opportunity. If it's possible, for instance, and there's some pretty good examples of this. I think that if you

• 1:27:49Tim Ferriss?

  even look at, for instance, before we started recording, we were talking about the big short. Yeah. If we look at some of these mortgage-backed securities, short bets that ended up producing these multi-billion dollar windfalls. Right.

• 1:28:05Tim Ferriss?

  Some of those positions were based on looking at publicly available data and drawing some pretty common sense conclusions. Right. Right? It wasn't Well, we think AI, proprietary AI from the Chinese government that was cracking this code. It was looking at

• 1:28:29Tim Ferriss?

  What's right in front of certain people and seeing something different and also asking a lot of questions about incentives.

• 1:28:36Ryan Holiday?

  Right.

• 1:28:37Tim Ferriss?

  Right? Like if you ask a venture capitalist if things are going to turn south, it's they're highly, highly, highly, highly, highly, subconsciously or consciously disincentivized from saying things are going to go south.

• 1:28:49Ryan Holiday?

  Unless they have a large bet that things are going to go south.

• 1:28:51Tim Ferriss?

  Which they would have to have either outside of venture capital.

• 1:28:55Ryan Holiday?

  Right, sure.

• 1:28:56Tim Ferriss?

  So it wouldn't be, it wouldn't be associated with their fund, or they'd have to have some like counter cyclical startup bet, which they may or may not, right? Conversely, if you're looking at, say, hedge fund investors, and that's a term that's fallen out of favor, but nonetheless, people who can place both long bets, we think this is going up or growing, and short bets, we think this is going down or decreasing in value, their view of the world's going to be very different than what they're willing to talk about.

• 1:29:26Ryan Holiday?

  Yeah.

• 1:29:27Tim Ferriss?

  So I find it incredibly, both really exciting and entirely terrifying that there are so many blind spots.

• 1:29:36Ryan Holiday?

  Well, Tyler Cowen talks about this with the three-point revolution in the NBA. Like, three-pointer has always been worth more than two-pointers.

• 1:29:45Tim Ferriss?

  Right.

• 1:29:46Ryan Holiday?

  And so you can miss a higher percentage of them and still score more points, right? Like, so, you know, percentage making of a, of a three-pointer is on average worth more than a, than a field goal, right? And he's like, literally, people were paid millions of dollars, million, billions of fans watched this game, and no one was like, hey, why don't we shoot more three-pointers?

• 1:30:06Tim Ferriss?

  Right.

• 1:30:07Ryan Holiday?

  You know, and, and then somebody did it, and the entire game changes.

• 1:30:10Tim Ferriss?

  Yeah. I wonder who that was, Steph Curry or someone comes in and just...

• 1:30:13Ryan Holiday?

  But like, that was even, not just like within our lifetime, like it was within the last half decade.

• 1:30:18Tim Ferriss?

  Yeah, yeah.

• 1:30:19Ryan Holiday?

  That, that the game fundamentally changed. And it's not like, it's not like they figured out the physics of shooting a three-pointer better, like.

• 1:30:26Tim Ferriss?

  Yeah.

• 1:30:27Ryan Holiday?

  Just now there's incentives, and so people shoot more three-pointers, and they make more, and that, a game literally that millions of people watched, just nobody noticed this thing right in front of them.

• 1:30:35Tim Ferriss?

  Yeah, yeah. Or like, you look at certain inventions, right? Wheels on luggage.

• 1:30:40Ryan Holiday?

  Yeah, I've heard you talk about this.

• 1:30:41Tim Ferriss?

  For God's sake, you know?

• 1:30:42Ryan Holiday?

  Yeah, right.

• 1:30:43Tim Ferriss?

  How long did that take? And it's, it's, it's sitting there right in plain sight.

• 1:30:46Ryan Holiday?

  Yeah.

• 1:30:47Tim Ferriss?

  And I think there are still... Practically infinite number of opportunities like that. And for me, at least, it all comes from just a better set of questions. And if you look at the process behind or that has been developed at places like IDEO or Frog Design or these different product development industrial design firms. A lot of it's asking questions, right? And trying to not just test the assumptions, but find the assumptions, identify the assumptions in something like grocery cart design. Yeah. Right? Like, what if we just completely take it for granted? Because this is the way it is and this is the way it's always been. Yeah.

• 1:31:31Tim Ferriss?

  And I find that really exciting when it comes to and I like to try to ask a lot of those questions. There's a great doc documentary called Objectified. Yeah. Which is about a lot of this. And I saw it a long time ago, made by the same filmmakers, I believe, who did a film called Helvetica. Such a good documentary. Yes, such a great doc. That brings up a lot of this. And when I see something that doesn't make sense or doesn't feel good, doesn't work well, I like to ask a lot of questions

• 1:32:14Tim Ferriss?

  and also combine that with studying incentives. Like, is there any reason, besides a design blind spot, that there weren't wheels on luggage earlier? Like, is there some, is someone incentivized Sure. in such a way that would make that? Like, did that idea exist 30 years earlier, but it never came to fruition? And if so, why might that be the case? Okay, let's do that as a thought exercise. Yeah. And for instance, I remember when Uber's a great example of this, right? I mean, I was involved with Uber before it was called Uber. It was Uber Cab LLC way back in the day, in like 2008. And we'll just refer to it as Uber for simplicity,

• 1:32:58Tim Ferriss?

  was widely mocked. I mean, it was put on Angel List, which is another company I'm involved with, angel.co, if people want to check it out. It was offered to investors and turned down, I want to say by hundreds of investors, as ludicrous. Yeah. And the math behind some of the ridicule looked at the existing market for, I want to say, black sedan car services. Right. And limousines. And in that analysis, in retrospect, we can see there are a bunch of false assumptions. Right. Right? They thought it was always going to be high-priced. Yeah. Where many things start out being prototyped among the privileged. Yeah.

• 1:33:43Tim Ferriss?

  Recycling, another great example of that. But then with scale, prices go down. It also assumed a relatively fixed market size. It's like, here's the existing market of black sedan use. We only see X percent of single-digit growth. Yeah. This is a shitty business because they'll never capture more than Y percent. Right. Missing the possibility, and ultimately the reality, which was that ride-sharing would create, expand that market exponentially and create its own market. Sure. Right?

• 1:34:26Tim Ferriss?

  And then you look at, let's just say, incentives of media coverage. Yeah. Right? Okay. At the time, and even more so now, it's very much in fashion to sort of attack anything that seems like it's catering to the 1%, right? Even though it's really critical to prototype with people who are price insensitive in the early stages of a lot of product development, because... Sure, they can subsidize it. If you're making one-offs, they're going to be fucking expensive. And if you're testing things and it's very rough around the edges, you can have these rich people, exactly, subsidize the product development that will ultimately lead to mass adoption. Yeah. So...

• 1:35:12Tim Ferriss?

  I find the whole thing just endlessly fascinating.

• 1:35:14Ryan Holiday?

  Yeah.

• 1:35:15Tim Ferriss?

  And I think it's also safe to assume that at almost any given point in time that almost everybody is getting it wrong.

• 1:35:22Ryan Holiday?

  Yeah.

• 1:35:23Tim Ferriss?

  With many, many, many, many, many things. And that to me says that if you just have, because this is not an intrinsic capability that I have. This has been, if we're talking about it from an investment perspective or opportunity spotting perspective, it is absolutely something that I have honed over time. And there are many people much better than I am. But when I've found questions I like, I borrow those questions and I put them into an Evernote notebook.

• 1:35:54Ryan Holiday?

  Yeah.

• 1:35:55Tim Ferriss?

  Under investing. I have these questions. When people point out misperceptions to me, and I'm like, holy shit, I totally missed that. How could I have missed that? I write those down. I'm like, wow, I completely, this never would have occurred to me now that they've said it. It's entirely self-evident. Like, how did I miss that? And why did they not? Wait, why did they not miss it?

• 1:36:16Ryan Holiday?

  Yeah.

• 1:36:17Tim Ferriss?

  I really think about these things. And over time, you can develop this

• 1:36:25Tim Ferriss?

  this very learnable skill of seeing things that other people don't see, which for me is mostly a byproduct of asking a lot of questions.

• 1:36:37Ryan Holiday?

  Well, that actually ties into what I was going to talk to you about next. There's a quote in Ego's Enemy, I have a quote from Bismarck where he says like, "Any fool can learn by experience. I prefer to learn by the experience of others." And it seems like, so you're doing experiments, you're doing trials, but you're also,

• 1:36:58Ryan Holiday?

  it seems like that's one bucket of learning for you. Then the other bucket is like a network of smart people you ask lots of questions of. And then the third one is like you read widely and deeply from different kinds of books, from history, from philosophy, from psychology. So you're not.

• 1:37:16Ryan Holiday?

  Spending 30 years of your life learning a lesson you could have learned on a $3 used Amazon purchase?

• 1:37:22Tim Ferriss?

  Oh, yeah. I much prefer to not make my own mistakes if I can avoid it, recognizing that of course I'm going to make all sorts of terrible mistakes. And to give an example of the second category, learning from other people and how I might approach that, we can talk about something we were discussing very briefly before we started recording, which is right now, I've noticed, and my team has noticed, some kind of odd behavior when it comes to email deliverability and open rates. And we have, by most measures, a large list, 1.5 million or something like that, for Five Bullet Friday and these various newsletters.

• 1:38:04Tim Ferriss?

  And we have already looked on Google, we've already talked to some of the parties involved, but these parties have various incentives that may or may not be totally aligned with ours. Not to say they're in any way malicious or nefarious, it's just different companies, different people, different parties in a different collaboration or transaction have different incentives. So, I and my team have been putting together an email, a draft email, to send to people like yourself, and it's really five or six people I know already who have large lists to ask a handful of questions. But if I simply email all of you with a handful of questions, it's a very one-sided interaction, right?

• 1:38:48Tim Ferriss?

  I'm asking someone to take time out of their day to help me with nothing in return. So what we've done is underneath each question, we are adding what we've tried, right? Like, here are the three things we've already tried to address this, here are the results. But we're still looking for more. What have you done or what would you do? Right? Step one, or question one, question two, question three, question four. And that could, at some point, turn into, we were joking earlier, the conversion cabal, registered trademark, I am funnel, here we go. I'm not going to do that. But that could turn into some type of brain trust.

• 1:39:29Ryan Holiday?

  Sure.

• 1:39:29Tim Ferriss?

  With a handful of people who then exchange best practices. Right? Where everyone is currently, or most people are very siloed.

• 1:39:38Ryan Holiday?

  Yeah.

• 1:39:38Tim Ferriss?

  So they're all trying to solve similar problems and have similar aspirations. Yet, even though all the newsletters that I'm thinking of, which are owned by people like yourself and these other folks, they're all non-competitive. They're all in different areas with different demographics. And it would make a lot of sense to have some information exchange. And that will start, the initial volley will be this email. Right? Where I'll share a bunch of stuff and we may or may not get replies. I hope we get replies. That would be an example of trying not to just make our own mistakes.

• 1:40:14Ryan Holiday?

  No, I'm going tomorrow, I'm flying to Arizona, and I'm meeting with five or six authors who you know. We go to this house in Sedona. They've all sold, each one of us sold hundreds of thousands of books, bestselling authors, and we just shoot the shit about stuff that's going on. We ask each other questions. And you could even argue that some of us are competitive. I don't think books are competitive. But like, the point is, like, why would we compete where we don't need to compete? Let's compete on, like, making great stuff. And let's get the other, you know what I mean? Like, that's what's been amazing for me with sports. Watching these, like, coaches give book recommendations to each other. Like, you'd think they would be competitive, but it's like, actually, they're getting the easy stuff out of the way, and then on Sunday, they're competing.

• 1:40:58Tim Ferriss?

  Yeah.

• 1:40:58Ryan Holiday?

  And so just, I think people can be really precious with information, when actually, you're almost always better sharing information.

• 1:41:06Tim Ferriss?

  Yeah. And on top of that,

• 1:41:11Tim Ferriss?

  I can very safely give my playbook for almost anything

• 1:41:17Ryan Holiday?

  Right.

• 1:41:17Tim Ferriss?

  to thousands of people.

• 1:41:19Ryan Holiday?

  Yeah.

• 1:41:20Tim Ferriss?

  And

• 1:41:23Tim Ferriss?

  almost no one's gonna implement any of it. And that's not to say that prescriptive how to stuff doesn't get used. It does.

• 1:41:30Ryan Holiday?

  Right.

• 1:41:31Tim Ferriss?

  Particularly when it's simple, right? Like slow carb diet, four hour body. Hundreds of thousands of people, maybe millions have used this diet successfully. It's simple, it's easy to follow. Everyone is following a diet.

• 1:41:43Ryan Holiday?

  Yeah.

• 1:41:43Tim Ferriss?

  Whether they choose to or not.

• 1:41:45Ryan Holiday?

  Sure.

• 1:41:46Tim Ferriss?

  But when it comes to, say, launching a book.

• 1:41:49Ryan Holiday?

  Yeah.

• 1:41:49Tim Ferriss?

  Right, and I lay out this monstrous post because I got tired of answering these questions as one offs. How to, I think it's called how to publish a bestseller? How to, how to publish a bestselling book this year? Or something like that. How to write a bestselling book this year? I can't remember the exact title. But it's this monster compilation post of like everything you can imagine related to writing, prepping, titling, publishing versus self-publishing, marketing, PR, all of it.

• 1:42:19Ryan Holiday?

  Yeah.

• 1:42:19Tim Ferriss?

  Blurb's, you name it. Every stone is turned. And people don't do it.

• 1:42:27Ryan Holiday?

  Yeah.

• 1:42:28Tim Ferriss?

  They're just like, no, I want the, I want the silver bullet easy answer.

• 1:42:31Ryan Holiday?

  Yeah, like, can I hire someone to do that for me?

• 1:42:33Tim Ferriss?

  Yeah, I was like, yeah, no. This is, I mean, maybe you can, but like, this is my blueprint.

• 1:42:39Ryan Holiday?

  Right.

• 1:42:40Tim Ferriss?

  I've used it repeatedly. It works. But guess what? You still have to write a fucking good book.

• 1:42:44Ryan Holiday?

  Right.

• 1:42:45Tim Ferriss?

  And not to say my books are the best in the world. They're not. I mean, I would like to see, I would like to think they're very useful, but I'm not Tolstoy. I recognize there are better writers out there. Nonetheless, I take the vast majority of energy and it goes into the writing.

• 1:43:02Ryan Holiday?

  Yeah.

• 1:43:05Tim Ferriss?

  But man. Yeah, it's, it's, it's pretty wild how, how little adherence there is.

• 1:43:13Ryan Holiday?

  Well, to go to that last bucket, maybe that's a place to wind up. What do you think about reading? Like, how do you find what you read? What's your methodology for breaking down books? Like, do you? Where do you get the knowledge that saves you painful trial and error?

• 1:43:30Tim Ferriss?

  I very rarely read anything that isn't recommended to me by either someone I know is very selective and snobby about book choice.

• 1:43:42Ryan Holiday?

  Yeah.

• 1:43:43Tim Ferriss?

  Uh, like, uh, say Naval Ravikant or my brother.

• 1:43:48Ryan Holiday?

  Yeah.

• 1:43:49Tim Ferriss?

  Uh, there are certain people who already have such a tight filter that anything, anything they read has passed a very high bar.

• 1:43:59Ryan Holiday?

  Yeah.

• 1:43:59Tim Ferriss?

  And anything they recommend has passed an even higher bar.

• 1:44:02Ryan Holiday?

  Yeah.

• 1:44:04Tim Ferriss?

  Uh, that is one way I get books referred to me that I take seriously. Another would, would be triangulating multiple points of recommendation. And then, uh, very often what I'll do is, let's just say I get a book recommended from, uh, people on social media or leaders or listeners. And I will prompt recommendations quite often by asking for

• 1:44:31Ryan Holiday?

  Yeah.

• 1:44:31Tim Ferriss?

  the best books on a certain topic. And, uh, perhaps a year ago or two years ago, I was very interested in learning more about the contemporary art world, not just the artists, but the gallerists and

• 1:44:46Ryan Holiday?

  Yeah, the whole industry.

• 1:44:47Tim Ferriss?

  the entire industry, the market, the black box, all the craziness that, that goes into that. And this book called The $12 Million Stuffed Shark popped up repeatedly.

• 1:44:58Ryan Holiday?

  Yeah.

• 1:44:58Tim Ferriss?

  I'm like, okay, let me take a look at that. And I looked at it, seemingly written by an economist. I go down then on Amazon, in this case, to the reviews. I don't read the one star reviews because they're like, I thought this was an Instapot. This is stupid.

• 1:45:15Ryan Holiday?

  Well, you know. My, my, mine came damaged in the mail.

• 1:45:17Tim Ferriss?

  Yeah, or it's just, they, they clearly didn't read the description. They're like, this wasn't a novel at all. It's like, yeah, dummy, it's not a novel. So I, I, I, I don't read the one star.

• 1:45:27Ryan Holiday?

  Yeah.

• 1:45:27Tim Ferriss?

  I don't read the, uh, what is the highest, five stars?

• 1:45:30Ryan Holiday?

  Yeah.

• 1:45:31Tim Ferriss?

  I don't read the five stars. I will read the most helpful three and four star.

• 1:45:36Ryan Holiday?

  Right.

• 1:45:37Tim Ferriss?

  Because I already have the gestalt. If the reviews are more than a few hundred reviews, I make the assumption that it is more or less reflective of the reality of the book.

• 1:45:49Ryan Holiday?

  Yeah.

• 1:45:51Tim Ferriss?

  Amazon reviews can very easily be gamed on a smaller level, but most authors are not going to be motivated enough to do it over a long period of time. So I assume if there are hundreds of reviews, or even a hundred plus, and I look at them and there are substantive reviews, that the overall star ranking is a broad indicator

• 1:46:18Ryan Holiday?

  Yeah.

• 1:46:18Tim Ferriss?

  of how much people have liked the book. Then I look at the most helpful three and four star reviews, because they will very often be, say, three paragraphs to two pages long, and they will really accurately lay out the structure of the book and like the strengths and weaknesses.

• 1:46:38Ryan Holiday?

  Sometimes they make you read the book better because you... Sometimes it spoils what's in the book, but then you actually understand it when you're reading it.

• 1:46:45Tim Ferriss?

  Yeah, absolutely. So I do that. And if at that point I'm interested, I download it on Kindle.

• 1:46:52Ryan Holiday?

  Yeah.

• 1:46:53Tim Ferriss?

  I try to do almost all of my reading on Kindle, which gives me the ability to highlight very easily. And then I can go to Notebook on Amazon or use any number of other services to grab those highlights and look at them on laptop, put them into Evernote, whatever it might be. But before I get there, I will look at the most popular highlights. I will also look at Goodreads. I like looking at Goodreads for quotes from given books. If you don't like, if you don't love

• 1:47:25Ryan Holiday?

  Yeah.

• 1:47:25Tim Ferriss?

  some of the quotes from the books, that's like hating the movie trailer and then going to see a three hour movie.

• 1:47:30Ryan Holiday?

  Right.

• 1:47:31Tim Ferriss?

  You're not going to like the movie.

• 1:47:32Ryan Holiday?

  Yeah.

• 1:47:32Tim Ferriss?

  So I look at Goodreads, and let's just say then I have the Kindle version. I will... I'll read two chapters, three chapters, and if I don't, if I'm not really grabbed, if I don't want to take a photograph of some of the highlights and send it to a friend, I will consider stopping reading.

• 1:47:52Ryan Holiday?

  Because life's too short?

• 1:47:53Tim Ferriss?

  Life's too fucking short. And Tim Urban of Wait But Why has so many great pieces, and one is called The Tail End, and he talks about the number of books he's likely to read in the rest of his life. And it's a shockingly, frighteningly low number.

• 1:48:08Ryan Holiday?

  Low number, yeah.

• 1:48:08Tim Ferriss?

  So I don't have enough time left in my life if we're assuming I'm gonna die. And I've looked at the, the, the death ages of my grandparents, great grandparents, et cetera. Then I've like isolated the males I've looked at. So there's a pretty decent chance I'll die somewhere between 80 and 85. I'm 43. There's not that much time left, especially if you consider sort of cognitive decline and so on. Right? So I've got, let's just call it, who knows, 20 to 30 years left of like good book reading.

• 1:48:44Ryan Holiday?

  Could also get hit by a bus.

• 1:48:45Tim Ferriss?

  I could get hit by a bus. So all that is to say, I don't have enough time to even read the classics I know the titles of.

• 1:48:53Ryan Holiday?

  Right.

• 1:48:53Tim Ferriss?

  Right, that I've heard of. I don't have time for that.

• 1:48:55Ryan Holiday?

  Right.

• 1:48:55Tim Ferriss?

  I don't have time to read all of those. So the idea that I would pick up a book and, and think to myself, this is pretty mediocre, and dedicate a week to reading it, is pure insanity. So I, I drop a lot of books. When I looked at, and I put up a blog post recently, looking at everything I read in 2019, all the books and favorite articles. And I included all the books I bought from Amazon. And I ended up completing somewhere between 30 and 40% of all the books that already made the cut to the point that I bought them.

• 1:49:33Ryan Holiday?

  Sure, sure.

• 1:49:34Tim Ferriss?

  And some of those I simply just never got around to, but a lot of them I, I stopped.

• 1:49:38Ryan Holiday?

  I like the rule of 100 pages minus your age.

• 1:49:43Tim Ferriss?

  That's, that's the, the taste test?

• 1:49:45Ryan Holiday?

  Yeah, that's when you quit.

• 1:49:46Tim Ferriss?

  Oh, okay.

• 1:49:47Ryan Holiday?

  So, so as you get older, you become more ruthless. As you're younger, you have to give it, because you don't know what the fuck you're talking about.

• 1:49:53Tim Ferriss?

  Yeah, yeah, yeah.

• 1:49:54Ryan Holiday?

  I like that.

• 1:49:55Tim Ferriss?

  I like that.

• 1:49:56Ryan Holiday?

  Yeah.

• 1:49:56Tim Ferriss?

  I like that.

• 1:49:57Ryan Holiday?

  But no, I think people are, they're like, I paid for this. That's, that's the sunk cost fallacy. They're like, I paid for this, I should finish it. It's like, you hate this book, so you're gonna give it hours of your life, weeks of your life?

• 1:50:07Tim Ferriss?

  Yeah.

• 1:50:07Ryan Holiday?

  Just to prove that you could finish a David Foster Wallace book? I mean, like, come on.

• 1:50:12Tim Ferriss?

  Yeah, and I was just thinking, one way you could maybe trick yourself into making better decisions with books is to imagine that the book you're reading is someone you're having dinner with.

• 1:50:22Ryan Holiday?

  Yeah.

• 1:50:22Tim Ferriss?

  And it's like, would you really sign up for like, five more dinners with this person?

• 1:50:26Ryan Holiday?

  Right.

• 1:50:27Tim Ferriss?

  If this is how you felt while you're reading it?

• 1:50:28Ryan Holiday?

  Sure.

• 1:50:29Tim Ferriss?

  No, you wouldn't.

• 1:50:30Ryan Holiday?

  Right.

• 1:50:30Tim Ferriss?

  And the call that-

• 1:50:32Ryan Holiday?

  You'd make up an excuse and you'd leave the dinner you're already at.

• 1:50:34Tim Ferriss?

  Yeah, exactly. So, uh, books are also a great way to procrastinate. Sort of a socially validated way to procrastinate. So I try to be ruthlessly honest with myself about that.

• 1:50:56Ryan Holiday?

  Interesting.

• 1:50:57Tim Ferriss?

  I will, there are a lot of great books out there.

• 1:51:01Ryan Holiday?

  Yeah.

• 1:51:01Tim Ferriss?

  I could spend all day, every day, reading great books.

• 1:51:04Ryan Holiday?

  Yeah.

• 1:51:04Tim Ferriss?

  And produce absolutely nothing of value.

• 1:51:07Ryan Holiday?

  Yeah.

• 1:51:07Tim Ferriss?

  So, I have increasingly tried to block out time. I have less, I would say, less and less time I dedicate to reading. And I'm going to be publishing a post this week, which is a public pronouncement, which helps with setting policies for saying no,

• 1:51:30Tim Ferriss?

  describing why I'm not gonna read any new books in, in 2020. So, anything that is published in 2020?

• 1:51:36Ryan Holiday?

  Oh, that's, my, my general rule is I almost always go towards older books.

• 1:51:41Tim Ferriss?

  Yeah. Can I say one thing?

• 1:51:43Ryan Holiday?

  Yeah.

• 1:51:44Tim Ferriss?

  So I'm gonna put out that post also to hold myself accountable.

• 1:51:46Ryan Holiday?

  Right.

• 1:51:47Tim Ferriss?

  Right?

• 1:51:47Ryan Holiday?

  Right.

• 1:51:48Tim Ferriss?

  Because if I get caught then reading something new, makes me look like a liar or hypocrite. And I use public

• 1:51:55Ryan Holiday?

  I won't have to do any book nerds.

• 1:51:57Tim Ferriss?

  I, oh, I definitely don't, don't, won't want to do those and don't want to do those. So this is a, this is a single decision that makes as Greg McKeown of Essentialism, which is a great book I recommend, would say.

• 1:52:10Ryan Holiday?

  Not new anymore, so.

• 1:52:12Tim Ferriss?

  Not new, yeah.

• 1:52:12Ryan Holiday?

  People can read it.

• 1:52:13Tim Ferriss?

  Oh, yeah, yeah, it's a fantastic book.

• 1:52:17Tim Ferriss?

  Looking for the single decisions that remove hundreds of decisions, right? So not reading any books in 2020 removes a lot of decisions. Someone says, oh, my God, you should read this book. It's new, sorry, I can't do it.

• 1:52:28Ryan Holiday?

  Right.

• 1:52:29Tim Ferriss?

  Right, it, it preserves so much of my cognitive decision-making bandwidth and energy for other things to make that one public. And for me, public is to a large audience, but for, in other areas of my life, I make public commitments to one or two or three friends or to my girlfriend so that they can hold me accountable.

• 1:52:52Ryan Holiday?

  Sure.

• 1:52:52Tim Ferriss?

  And I, I find great value in that. If you're trying to guard against your lesser self, I find that really useful.

• 1:52:58Ryan Holiday?

  No, and I think, I think with, it's like, so the, the cost of a book is financial, primarily time, and then what you're gonna put in your brain. I don't want to read things that are gonna be subsequently or very quickly proven irrelevant or proven, you know, incorrect or out of fashion. Like, you'd be better off sitting down and reading Shakespeare's plays because that is, that has not only had 500 years of cultural impact, but will probably have 500 more years of cultural impact. So like, I think, looking at the half-life of information and deciding to consume information

• 1:53:40Ryan Holiday?

  that's likely to remain true over time, it forces you to be both more general, but also more timeless. Meanwhile, if you read a book about the first year of the Trump presidency. Or how many books like, like a couple of years ago, or a year or so ago, somebody wrote a book about Uber and then like, the founder was fired shortly after the book came. It's like, that book is, the guy who finished that book wasted his time because it's already irrelevant by subsequent events. And I think we have a newness bias that prevents us from accumulating wisdom where we could be finding it.

• 1:54:14Tim Ferriss?

  Yeah. I, I'm more interested these days in the pieces of the puzzle. And by the puzzle, we could be talking about anything, right?

• 1:54:29Ryan Holiday?

  Sure.

• 1:54:30Tim Ferriss?

  We could be talking about human behavior. We could be talking about the, the rise and fall of nations that are kind of like the tectonic plates.

• 1:54:38Ryan Holiday?

  Sure.

• 1:54:38Tim Ferriss?

  I'm more interested in those because there's a bit more certainty and a higher degree of confidence in identifying and understanding some of those elements, right? If they've been shown over and over again throughout history, or proven, or I suppose, based on what I said earlier, shown to be very likely repeatedly in, in science.

• 1:55:05Ryan Holiday?

  Yeah.

• 1:55:06Tim Ferriss?

  So, this all makes me think of this quote by, I'm thinking of getting the name right, Donald Knuth, K-N-U-T-H, who was at, I want to say IBM, might be IBM, but doesn't really matter. The point being, he stopped using email at one point.

• 1:55:27Ryan Holiday?

  Yeah.

• 1:55:28Tim Ferriss?

  Completely stopped. And he said, for, for people who want to stay on top of things, email is great. He's like, but, but I want to get to the bottom of things.

• 1:55:37Ryan Holiday?

  Ooh.

• 1:55:38Tim Ferriss?

  And I've thought about that a lot.

• 1:55:39Ryan Holiday?

  Yeah.

• 1:55:40Tim Ferriss?

  Because keeping on top of things is a losing game.

• 1:55:43Ryan Holiday?

  Yeah.

• 1:55:44Tim Ferriss?

  It's just...

• 1:55:45Ryan Holiday?

  By definition.

• 1:55:46Tim Ferriss?

  Yeah.

• 1:55:46Ryan Holiday?

  New stuff's happening.

• 1:55:47Tim Ferriss?

  It's a losing game and there are people who are going to be more dedicated and obsessive with current affairs. I have no competitive advantage. I have no information advantage. I actually have a lot of information advantage, but I have no desire or behavioral advantage with current events.

• 1:56:06Ryan Holiday?

  Right.

• 1:56:06Tim Ferriss?

  And it also breeds sort of emotionally and physically.

• 1:56:12Tim Ferriss?

  A life driven by cortisol and FOMO and so on. Whereas if I'm able to discipline myself enough, which I partially do through this public accountability, to focus on studying things that have endured, I just feel much better in life in general, and I make better decisions.

• 1:56:37Ryan Holiday?

  Yeah, look, they didn't have the news 250 years ago. Do you know what I mean? They did fine.

• 1:56:43Tim Ferriss?

  Yeah, yeah, yeah.

• 1:56:44Ryan Holiday?

  They did fine.

• 1:56:45Tim Ferriss?

  Yeah, they did just fine. So, ah, man.

• 1:56:50Tim Ferriss?

  Yeah, the news. Happy to miss the news.

• 1:56:53Ryan Holiday?

  Yeah, of course, of course. I'd rather have truth than trivia.

• 1:56:57Tim Ferriss?

  Yeah. So, Ryan, I suppose this is the time when we say goodbye?

• 1:57:01Ryan Holiday?

  Yep.

• 1:57:02Tim Ferriss?

  Tearful, tearful, stoic, holiday goodbye.

• 1:57:05Ryan Holiday?

  Yeah.

• 1:57:06Tim Ferriss?

  Where can people find you online? Learn more about you? What would you like to tell people about your current projects?

• 1:57:13Ryan Holiday?

  Yeah, maybe check out Daily Stoic, which is a Stoicism-inspired email each morning. Also @DailyStoic on most platforms. And then I'm Ryan Holiday pretty much any bookstore.

• 1:57:26Tim Ferriss?

  Across the socials and across the bookstores?

• 1:57:28Ryan Holiday?

  Yes.

• 1:57:29Tim Ferriss?

  So, if people look at your selection of books and think to themselves, "I don't know where to start", where would you suggest people start with your writing?

• 1:57:37Ryan Holiday?

  It's a good question.

• 1:57:40Ryan Holiday?

  I'd start with "The Obstacle is the Way", or "Stillness is the Key", depending, it's like if you're going through something tough, I'd start with "The Obstacle is the Way". If you're maybe dealing with some of the stuff we're talking about, which is sort of life optimization, what do I want, how do I manage? Maybe I'd do Stillness.

• 1:57:56Tim Ferriss?

  All right.

• 1:57:56Ryan Holiday?

  Yeah.

• 1:57:58Tim Ferriss?

  And there you have it, folks. Thank you, Ryan.

• 1:58:00Ryan Holiday?

  Yeah.

• 1:58:01Tim Ferriss?

  And as those listening probably know, this is Tim Ferriss, signing off for now. Thank you for listening. And until next time, experiment well, experiment widely, and test those assumptions.

• 1:58:14Tim Ferriss?

  Hey guys, this is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday? That provides a little morsel of fun before the weekend. And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric, as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short.

• 1:58:56Tim Ferriss?

  It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to fourhourworkweek.com. That's fourhourworkweek.com all spelled out. And just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by 99designs, the global creative platform that makes it easy for you to find and work with amazing graphic designers online. Longtime listeners of this podcast know how much attention I pay to detail, how obsessively I approach nearly all elements of my work, because the small things often end up being the big things. So whether it's your logo, your business cards, website design, even your email templates,

• 1:59:38Tim Ferriss?

  all of these visual elements tell your customers, tell your users who you are and what you're about. So I think it's worth sweating the details. I've been using 99designs for years now to ensure that many of my creative projects, whether big or small, are as cohesive, professional, and beautiful as possible. I've worked on draft mockups of book covers. I've worked on all sorts of things. Most recently, I've been working with a designer at 99designs to update the illustrations and layouts for all of my downloadable ebooks. I've developed a really great working relationship with a designer who goes by the username Spoonlancer, and I intend to continue working with him to bring ideas to life, one project at a time. I've also used 99designs for all sorts of high-end illustration for different books, like the

• 2:00:23Tim Ferriss?

  You can see a bunch of examples on my Instagram that I've put up and they've turned out better than I possibly could have hoped. So from logos to websites, packaging to books, 99designs is the go-to creative resource to build your brand on any budget. So check them out. Right now, my listeners, that's you guys, can get $20 off plus a free $99 upgrade on their first design contest. A contest is a great way to get started and find the right designer for long-term work. You can also book a free design consultation with a brand expert at 99designs to receive personalized branding advice over the phone. Their hands-on team has helped thousands of business owners at this point. It's a great way to get the most out of your experience with 99designs. So, take a look. Head to

• 2:01:07Tim Ferriss?

  99designs.com/tim for your discount and to sign up for design consultation today. That's 99designs.com/tim. This episode is brought to you by LinkedIn Jobs. Hiring can be hard, can be super, super expensive and very painful if you get it wrong. I certainly have had that experience multiple times, have made a lot of mistakes. I am not eager to repeat any of them. So, I try to do as much vetting as possible now on the front end. Today, with more qualified candidates than ever, but certainly more noise than ever, employers need a hiring solution that helps them find the right people for their businesses without wasting time, without wasting money. LinkedIn Jobs provides just that. LinkedIn Jobs screens

• 2:01:50Tim Ferriss?

  candidates with the hard and soft skills that you specify that you're looking for so you can quickly find and hire the right person. They also look beyond work skills, so collaboration, creativity, adaptability to connect you with candidates who match your business perfectly. They have endless business-specific data points that help them to massage this and that which can help you to find the best fit. LinkedIn can make sure your job post gets in front of people you want to hire, people with the skills, qualifications and other insights that help LinkedIn paint a better picture of potential candidates. It's no wonder that great candidates are hired every eight seconds on average on LinkedIn. That's pretty wild, every eight seconds. So, find the right person meant for your business today with LinkedIn Jobs.

• 2:02:34Tim Ferriss?

  You can pay what you want and the first $50 is on LinkedIn. Just visit LinkedIn.com/Tim for more details. Again, that's LinkedIn.com/Tim to get $50 off your first job post. Let's check it out. LinkedIn.com/Tim. Terms and conditions do apply.