Inside Ryan Holiday’s $250K Reading List

You could spend a lot of time and money earning an MBA, or you could start with these books that will change how you think about business, leadership, and success. Watch this episode on Ryan Holiday's YouTube https://www.youtube.com/watch?v=ZfVwQ1aKiDY channel: https://www.youtube.com/watch?v=ZfVwQ1aKiDY Turn the words into works 👉https://dailystoic.com/readRead to Lead: A Daily Stoic Reading Challenge https://dailystoic.com/read | https://challenge.dailystoic.com/readtolead 📚 Books Mentioned: Trillion Dollar Coach by Eric Schmidt: https://www.thepaintedporch.com/products/trillion-dollar-coach-the-leadership-playbook-of-silicon-valleys-bill-campbell?_pos=1&_sid=11237a736&_ss=r https://www.thepaintedporch.com/products/trillion-dollar-coach-the-leadership-playbook-of-silicon-valleys-bill-campbell?_pos=1&_sid=11237a736&_ss=r What I Learned Losing A Million Dollars by Jim Paul:https://www.thepaintedporch.com/products/business21?_pos=1&_sid=b4255505c&_ss=r https://www.thepaintedporch.com/products/business21?_pos=1&_sid=b4255505c&_ss=r Billion Dollar Lessons by Paul Carroll: https://www.thepaintedporch.com/products/business3?_pos=1&_sid=d2e26d9c3&_ss=r https://www.thepaintedporch.com/products/business3?_pos=1&_sid=d2e26d9c3&_ss=r How I Built This by Guy Raz: https://www.thepaintedporch.com/products/how-i-built-this-the-unexpected-paths-to-success-from-the-worlds-most-inspiring-entrepreneurs?_pos=1&_sid=02d0960d7&_ss=r https://www.thepaintedporch.com/products/how-i-built-this-the-unexpected-paths-to-success-from-the-worlds-most-inspiring-entrepreneurs?_pos=1&_sid=02d0960d7&_ss=r Good to Great by Jim Collins: https://www.thepaintedporch.com/products/business9?_pos=1&_sid=44860c5d9&_ss=r https://www.thepaintedporch.com/products/business9?_pos=1&_sid=44860c5d9&_ss=r Unreasonable Hospitality by Will Guidara: https://www.thepaintedporch.com/products/unreasonable-hospitality-the-remarkable-power-of-giving-people-more-than-they-expect?_pos=1&_sid=3c24601da&_ss=r https://www.thepaintedporch.com/products/unreasonable-hospitality-the-remarkable-power-of-giving-people-more-than-they-expect?_pos=1&_sid=3c24601da&_ss=r Setting The Table by Danny Meyer: https://www.thepaintedporch.com/products/food11?_pos=1&_sid=9e7ea16ad&_ss=r https://www.thepaintedporch.com/products/food11?_pos=1&_sid=9e7ea16ad&_ss=r Conspiracy by Ryan Holiday:https://www.thepaintedporch.com/products/ryan10?_pos=1&_sid=144e67fc9&_ss=r https://www.thepaintedporch.com/products/ryan10?_pos=1&_sid=144e67fc9&_ss=r Zero To One by Peter Thiel: https://www.thepaintedporch.com/products/zero-to-one-notes-on-startups-or-how-to-build-the-future?_pos=1&_sid=996ff7a4f&_ss=r https://www.thepaintedporch.com/products/zero-to-one-notes-on-startups-or-how-to-build-the-future?_pos=1&_sid=996ff7a4f&_ss=r The Personal MBA by Josh Kaufman: https://www.thepaintedporch.com/products/the-personal-mba-10th-anniversary-edition?_pos=1&_sid=29a294c29&_ss=r https://www.thepaintedporch.com/products/the-personal-mba-10th-anniversary-edition?_pos=1&_sid=29a294c29&_ss=r The 22 Immutable Laws Of Marketing by Al Ries and Jack Trout: https://www.thepaintedporch.com/products/22-immutable-laws-of-marketing-exposed-and-explained-by-the-worlds-two?_pos=1&_sid=643131534&_ss=r https://www.thepaintedporch.com/products/22-immutable-laws-of-marketing-exposed-and-explained-by-the-worlds-two?_pos=1&_sid=643131534&_ss=r Blue Ocean Strategy by W. Chan Kim: https://www.thepaintedporch.com/products/business5?_pos=1&_sid=01f8feaf1&_ss=r https://www.thepaintedporch.com/products/business5?_pos=1&_sid=01f8feaf1&_ss=r The $100 Startup by Chris Guillebeau:https://www.thepaintedporch.com/products/rhmoo15?_pos=1&_sid=fc8fc570b&_ss=r https://www.thepaintedporch.com/products/rhmoo15?_pos=1&_sid=fc8fc570b&_ss=r The Lean Startup by Eric Ries: https://www.thepaintedporch.com/products/lean-startup-how-todays-entrepreneurs-use-continuous-innovation-to-create-radically-successful-businesses?_pos=1&_sid=6654e5edd&_ss=r https://www.thepaintedporch.com/products/lean-startup-how-todays-entrepreneurs-use-continuous-innovation-to-create-radically-successful-businesses?_pos=1&_sid=6654e5edd&_ss=r Thinking in Bets by Annie Duke: https://www.thepaintedporch.com/products/business19?_pos=1&_sid=d28793e26&_ss=r https://www.thepaintedporch.com/products/business19?_pos=1&_sid=d28793e26&_ss=r The Hard Thing About Hard Things by Ben Horowitz: https://www.thepaintedporch.com/products/hard-thing-about-hard-things-building-a-business-when-there-are-no-easy-answers?_pos=1&_sid=0b4ef0043&_ss=r https://www.thepaintedporch.com/products/hard-thing-about-hard-things-building-a-business-when-there-are-no-easy-answers?_pos=1&_sid=0b4ef0043&_ss=r Essentialism by Greg McKeown: https://www.thepaintedporch.com/products/rhmoo38?_pos=1&_sid=a012783cc&_ss=r https://www.thepaintedporch.com/products/rhmoo38?_pos=1&_sid=a012783cc&_ss=r 33 Strategies of War by Robert Greene: https://www.thepaintedporch.com/products/33-strategies-of-war-signed-by-robert-greene?_pos=1&_sid=76476b86e&_ss=r https://www.thepaintedporch.com/products/33-strategies-of-war-signed-by-robert-greene?_pos=1&_sid=76476b86e&_ss=r The 48 Laws of Power by Robert Greene: https://www.thepaintedporch.com/products/48-laws-of-power-signed?_pos=1&_sid=eb6bc3ea2&_ss=r https://www.thepaintedporch.com/products/48-laws-of-power-signed?_pos=1&_sid=eb6bc3ea2&_ss=r Art of Seduction by Robert Greene: https://www.thepaintedporch.com/products/art-of-seduction?_pos=10&_sid=360eeb439&_ss=r https://www.thepaintedporch.com/products/art-of-seduction?_pos=10&_sid=360eeb439&_ss=r 🎟️https://www.dailystoiclive.com/DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🎙️AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing toThe Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content:https://dailystoic.supercast.com/ ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://dailystoic.com/dailyemail -- Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are. Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.

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

• 0:00Ryan Holiday?

  We were looking to spruce up our, our front porch. The weather's finally getting better. We wanted to spend some time hanging out outside with the kids. So we got these awesome hammocks and we actually got them from today's sponsor, Wayfair. If you drove by our, our house, you'd see us out there with our kids reading. We've got this new kitten all hanging out in the hammocks. It's been awesome. And that's because on Wayfair, you'll find quality materials that stand up to real life. They sell furniture and decor that's built to last. And when you shop with Wayfair Verified, it's your shortcut to durable pieces that are hand vetted by product specialists using their 10-point quality inspection. They've got thousands of products at every style and budget, whether you're simply replacing an appliance or transforming your home from top to bottom this holiday season. Wayfair's got great

• 0:43Ryan Holiday?

  reviews as well. So you can find more than 20 million verified five-star reviews from real shoppers. Find pieces made for real life and get even more value with Wayfair Rewards. Join Wayfair Rewards today and get 5% back on every purchase. Head over to wayfair.com to shop all things home. W A Y F A I R dot com.

• 1:04Speaker 01

  Wayfair, every style, every home.

• 1:07Ryan Holiday?

  An MBA can cost as much as $250,000. Meanwhile, Warren Buffett's Business Empire, one of the most successful companies and investment runs in human history, was built on the knowledge he got from a book that he paid less than $2 for in the 1960s. My whole life was changed by a copy of Mark Sproul's Meditations that I bought for $9 on Amazon. It changed me personally and also professionally. This bookstore, my books, which has sold millions of copies, none of that would be possible had I not learned what was in between those two covers. So I wanted to give you some book recommendations that even if you buy all of them, even if you bought signed first editions of all of

• 1:50Ryan Holiday?

  them, would be cheaper and better than an MBA.

• 1:57Ryan Holiday?

  Let's start with some of my favorite business books. Not that business books are the end all be all. In fact, I think philosophy and psychology and books about history and human nature are more important, but we'll start with some business ones. Here is Trillion Dollar Coach. This is written by Eric Schmidt, one of the most successful business CEOs of all time. But this is about one of the greatest leadership coaches of all time who mentored and coached Steve Jobs, Larry Page, and some of the biggest CEOs in the history of Silicon Valley. This one is great. Everyone should read. What I Learned: Losing $1 Million is about a trader on the Chicago Stock Exchange who blows it in the eighties and loses over $1 million. Obviously today, they're playing with slightly larger amounts of money, but

• 2:38Ryan Holiday?

  this one is really good. I would also pair it with another book about failure, which we should have here somewhere. Billion Dollar Lessons. Again, you can learn as much from people's very expensive failures than you can from their successes. Guy Raz has interviewed basically every CEO of a big or new company of the last generation or so. This book, How I Built This, is incredible. Actually, funny story. We have a hardcover of How I Built This up there in the book tower. Can't have that one. I don't think it's coming out anytime soon. Jim Collins, Good to Great. This one's very important. Unreasonable Hospitality, one of the great restaurateurs and hospitality experts. This book is great.

• 3:23Ryan Holiday?

  Pair that with Danny Meyer. Peter Thiel, who I wrote a book about, Zero to One. Obviously controversial guy, but his thinking here is incredible. Everyone should read this. And then maybe let's do personal MBA, since we're talking about how to get an MBA. As far as marketing goes, I'd also throw in the 22 Immutable Laws of Marketing. This is both a marketing and a business and a life strategy, blue ocean strategy. The best businesses, the most successful businesses, the most successful entrepreneurs, most successful artists, they're not better than the people that are doing what they do. Usually they got there because they were the only one doing what they do. You want to go to where you have a monopoly. Peter Thiel talks about that in Zero to One. And you don't

• 4:04Ryan Holiday?

  do that by kicking out all the competitors. You do that by going to where there are no competitors. Be a one of one. Be the only one doing your thing. We're all unique. We are all different. Don't try to be like everyone else. Go to the blue ocean. This book is very important. It's very instrumental in my career and my business strategy. Again, when you're thinking about an MBA, it's costing $250,000. People think starting a business is so, so expensive. And some of them are. Some businesses are really capital intensive. But I do like the $100 startup. Noah Kagan's also written some interesting stuff on how it is much cheaper and easier to start a company if you start really small. Eric Ries talks about this in Lean Startup. Very good. Andy Duke talking about this, Thinking in

• 4:48Ryan Holiday?

  Bets. Shrinking the, the risks that you're taking is really important. Ben Horowitz, Hard Thing About Hard Things. You will have to make hard decisions in life and in leadership. Very important. McCowen's Essentialism, also really good. As Mark Sproul says, when you eliminate the inessential, get the double benefit of doing the essential things better. I'd also throw in Robert Greene's stuff. Thirty-Three Strategy of War. This is an incredibly powerful book for anyone launching a campaign or in the midst of a battle of some kind, literal or figuratively. I would also add in the 48 Laws of Power. You don't have to be one of the people in the book, but you want to be able to protect against the people who operate like that in the book. And then I would, I could see this book being

• 5:31Ryan Holiday?

  on the desk of any student or future CEO. It's one lesson a day from all of his books. Thirty-Three Strategy of War, Laws of Human Nature, Forty Laws of Power, Art of Seduction Mastery. So this is power, seduction, mastery, strategy, and human nature. These are all things that hopefully you would learn in an MBA program, but clearly most people don't. Let's go over here to leadership, because that's what ultimately you are being primed to do. Blue McRaven's stuff. Guy Gitts, Bin Laden. I really like Admiral James Stavridis' his book, Sailing True North and To Risk It All. These are about great naval leaders,

• 6:13Ryan Holiday?

  for the most part. People who had to do some incredibly dangerous or scary things. This is journeys and how character develops and shapes a leader. Highly recommend. I put Charles Duhigg's Super Communicators on this list as well. If you can't communicate, if you can't listen, if you can't connect with people, you're going to have a lot of trouble. Look, hiring is make or break for a business, especially if you're a small business. You can't just hope that you find the right people. Hope is never a strategy, but when it comes to recruitment, it's not going to work. So when the pressure's on and you need the right hire, this is a job for sponsored jobs. Indeed Sponsored Jobs gets you the quality candidates

• 6:56Ryan Holiday?

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• 7:38Ryan Holiday?

  right now and support the show by saying you heard about Indeed on this podcast. Indeed.com/podcast. Terms and conditions apply. If you're hiring now, then this is a job for Indeed Sponsored Jobs. Benjamin Franklin said, "Time is money" in 1748. That was his advice to a young man. 278 years later, some of us, depending on what you do, are still spending part of every month typing receipts into a form. It's bad use of your time. That's bad use of company time. Expense reports are tedious. It's not what I want my employees doing. Well, Ramp makes collecting and submitting expenses super simple. With Ramp, expenses submit themselves. You just text or email your receipt and Ramp categorizes codes and submits

• 8:22Ryan Holiday?

  it. And when you book business travel with Ramp, they find the best flights and hotels you're actually allowed to book. You don't find out later that your company's only partially going to cover it. Ramp is the only finance platform that employees and finance teams both rave about, and companies have saved over $12 billion with Ramp. Time is money. Save both with Ramp. New customers get $250 off at ramp.com/dailystoic. That's ramp.com/dailystoic. Now let's go a little bit back in time here. Plutarch's How to Be a Leader. He's speaking about this not just as a scholar and a biographer, but he is a leader in Greece and Rome. Really

• 9:06Ryan Holiday?

  like this book. I would throw in Seneca's How to Keep Your Cool.

• 9:12Ryan Holiday?

  And this little collection of Diogenes the Cynic, How to Say No. Diogenes the Cynic manages to say no to Alexander the Great, the most powerful man in the world. How to Think Like a Roman Emperor. We had more leaders and business people who would think like a Roman emperor. They'd be more successful. This is Donald Robinson's book on Marcus Aurelius. And then, of course, every leader should read Marcus Aurelius's Meditations, The Private Thoughts of the Most Powerful Man in the World. Unlike, you know, your typical business memoir, which is performative, which is about the CEO trying to transition to be a speaker or a consultant or caring about their legacy. This is just Marcus Aurelius writing notes to himself about what he's thinking about, what he needs to know.

• 9:55Ryan Holiday?

  Maybe in your MBA, you're reading Adam Smith's Wealth of Nations. Obviously important, the bedrock of modern capitalism. But here is the moral philosophy of Adam Smith, which I think is really important, by a great economist named Russ Roberts, who really liked that book. In 1962, the Navy sends Commander James Stockdale, a fighter pilot, back to college to get not an MBA, but a master's nevertheless. And he ends up studying philosophy at Stanford. And that shapes what becomes not just this book, Thoughts of a Philosophical Fighter Pilot, which is some of the best essays and articles on leadership and adversity and difficulty that you'll ever read. I mentioned Jim Collins' Good to Great. Stockdale Paradox is in that book.

• 10:38Ryan Holiday?

  But when Stockdale is shot down and has to lead 500 or so aviators through imprisonment, torture, deprivation, isolation, he's drawing on what he learned there at Stanford and from the Stoics. Incredibly powerful book. And of course, biography is the best way to learn about how to lead, how not to lead. Chernel's Titan, incredible. Weirdly, a lot of business lessons here of what not to do in his biography of Mark Twain. Mark Twain was a great writer, a great thinker, but he wanted to be an entrepreneur. He's always falling for schemes, always thought he had the next big company. Lost most of the money he made writing as a result.

• 11:21Ryan Holiday?

  This, Howard Hughes, His Life in Madness. Cautionary Tale, genius, disruptive entrepreneur, brilliant guy, also insane, also an egomaniac. How did I learn about this cautionary tale? Actually, I read about it in an interview that Elon Musk gave. So he clearly read it and then forgot most of the lessons. Walter Isaacson's Steve Jobs. Elon Musk, great. His book on Benjamin Franklin, also incredibly successful and brilliant business person. I liked this book on the Wright Brothers as a type of creative, the power of creativity to make something new and how much powerful it is even than incentives. And then I would give you these two moral biographies,

• 12:06Ryan Holiday?

  is what they're called, of President Lincoln. Lincoln's Virtues and President Lincoln. Again, it's not just about how good you are at the thing, but what is the thing you are trying to do? I think that's very powerful. I would recommend those. And then Team of Rivals, absolute must read. Lincoln's genius as a wielder of an unwieldy cabinet. His ability to use people he disagreed with, people who had divergent interests from him. But his ability to bring people together and manage that is just absolutely incredible. And then let's wrap up with some memoirs of great leaders. Jerry Weintraub, producer, tour manager, et cetera, for Elvis.

• 12:50Ryan Holiday?

  Sinatra, producer of Nashville. Karate Kid movies, Diner, Ocean's Eleven, Ocean's Twelve. Fascinating guy. This is actually written with Rich Cohen, who's one of my favorite writers, who did this book, Fish That Ate the Whale, about the Samuel Zemurray, who starts as the little guy, ends up being acquired by United Fruit, takes over United Fruit. That's how he's known as the fish that ate the whale. He has a line in this book, basically, you could ignore, forget everything you learned in business school. But if you read the story of Sam the Banana Man, you could go pretty far in life. Samuel Zemurray is lacking a moral compass in many ways. So this has to be balanced out with some of the leadership and the philosophy stuff we're talking about.

• 13:32Ryan Holiday?

  But as far as being a genius businessman and a crafty entrepreneur, that is an incredible memoir that everyone should read. Of course, Shoe Dog, about Phil Knight, also very incredible. What I thought was great about that book, if you read most business books, one of the problems with it is that they sort of skip over the early days. They just go to when it became huge and successful. This book is about the early days, the grind. When he's the shoe dog selling shoes out of the trunk of his car. It really goes into the minutia of the early days of Nike, which I think is really, really important and rounds out a part of the entrepreneur and business and leadership perspective that is not told often enough.

• 14:15Ryan Holiday?

  Let's do some quick things here. Thinking Fast and Slow. You're making decisions. As a business person, you need to know your cognitive biases. Cognitive dissonance being one of the biggest ones. So this book on cognitive dissonance, Mistakes Were Made But Not By Me, very important, highly recommend. As far as persuasion goes, I might put words that work up there with some of the ones we were talking about earlier, as well as mindset. Do you ever feel like other people are getting more out of their books than you are? You finish a book that everyone's been raving about and you're like, I don't get it. Did I miss something? Or there's this book that you've always wanted to read, that you heard is important, that you heard has great stuff in it, and you can't seem to get through it? There's nothing wrong with you.

• 15:00Ryan Holiday?

  It's just that really great readers, all the great readers that I've met in my life, they're not just winging it. They have a system. There are practices. I myself was taught how to read, how to break down a book, how to take everything I need to get out of it from the great Robert Greene. Great readers know which books to pick. They know what to look for. They know how to process, retain. They know how to do the most important thing there is to do with a great book, which, as Seneca said, is to turn those words into works. We're trying to read to become better people. This is what Truman was getting at when he said that not all readers are leaders,

• 15:42Ryan Holiday?

  but every leader has to be a reader. Okay, so how can you be a better reader? Well, that's what we built a Daily Stoic Read to Lead course around. I'm going to show you the system that I have developed over the years to read books in all different kinds of genres, all different lengths, all different styles. If it works for me at a college dropout, I'm pretty sure it will work for you too. Actually, let me, let me show you my system.

• 16:15Ryan Holiday?

  Like when I read something difficult, I take notes. I transfer those notes onto note cards. I break books down, talk about the ideas, work on them. I put them into practice. This isn't just the system that I use. This isn't just the things that I was taught by people like Robert Greene and others. But it's also how the ancients read, how the Stoics read, Marcus Aurelius, Seneca, Epictetus, thousands of years of wisdom extracted from books in the centuries since. And we're going to share it with all of you. We've had this course for a really long time. People have loved it. They asked us to bring it back. So that's what we're doing. And we'd love to have you join us. You can sign up right now, dailystoic.com/readtolead.

• 17:04Speaker 02

  Talking about guns with others might not always feel comfortable, but it could save a life. Here's a way to start a conversation. Your family is going over to your neighbor's home for dinner for the first time. How would you ask if there are any unlocked guns in the home?

• 17:17Speaker 03

  Hey.

• 17:18Speaker 02

  Hey, we're so excited for tonight. Before we come over, though, may I ask if there are any unlocked guns in your home?

• 17:23Speaker 03

  Our guns are stored securely, locked in a safe that the kids can't access.

• 17:28Speaker 02

  Awesome. Learn how to have the conversation at agree to agree.org. Brought to you by the Ad Council.