Inside Ryan Holiday’s $250K Reading List

0:00Ryan Holiday: So I have a bunch of traveling I'm doing through the end of the year on Daily Stoic Live Tour. I just got back from San Diego. I like to stay in the places that I'm staying. I like to book places on Airbnb so I can be like a local. I not only do some of my best writing, but I learn about things that I wouldn't have known otherwise. When I was just in San Diego, I took a walk along the water. I bumped into someone who recognized me and they told me about their favorite local bookstore, which was like two blocks from where I was staying. And I never would have known about it if it wasn't for that encounter.

0:30Ryan Holiday: It was cool to me to think that I have helped facilitate that experience for many, many people coming to Austin over the years. The first house that I bought in Austin when my wife and I first moved here, we would list it on Airbnb and it helped me make the transition from my corporate life to being a full-time writer. So if you're going to be away, you should maybe think about listing your place on Airbnb. It can be a great way to earn extra cash while you travel. It can offset the cost of your trip or maybe even go towards whatever you're doing next. If you've got travel coming up, check out Airbnb.

1:01Ryan Holiday: Your home might be worth more than you think. And you can find out how much at Airbnb.com slash host. 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 Spurius' Meditations that I bought for$9 on Amazon. It changed me personally and also professionally. This bookstore, my books, which have sold millions of copies, none of that would be possible had I not learned what was in between those two covers.

1:42Ryan Holiday: 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 them, would be cheaper and better than an MBA.

1:57Let's start with some of my favorite business books.

2:00Ryan Holiday: 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 a Million Dollars. It's about a trader on the Chicago Stock Exchange who blows it in the 80s and loses over a million dollars.

2:35Ryan Holiday: Obviously today they're playing with slightly larger amounts of money, but this one is really good. I would also pair it with another book about failure, which we should have here somewhere. Ah, 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.

3:13Ryan Holiday: Jim Collins, Good to Great. This one's very important. Unreasonable Hospitality, one of the great restaurateurs and hospitality experts. This book is great. 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 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.

4:13Ryan Holiday: 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 the lean startup. Very good. Andy Duke talking about this thinking in bets.

4:49Ryan Holiday: Shrinking 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. McAllen's essentialism, also really good. As Mark Scurula 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 33 Strategies 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 on the desk of any student or future CEO it's one lesson a day from all of his books uh 33 strategies war laws of human nature 48 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 william mcraven's stuff guy who gets bin laden i really like Admiral James Stavridis, his book Sailing True North and To Risk It All.

6:10Ryan Holiday: These are about great naval leaders 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. We were looking to spruce up 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.

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8:00Ryan Holiday: NetSuite Next surfaces insights exactly when you need them, puts agents to work on routine tasks and problems, and lets you ask complex questions in plain language like talking to a knowledgeable colleague. But technology is only part of the story. AI is also shaping how people and teams work together. That shift is underway. And that's why there is a new expert created business guide for you. It's called Aligning for the Agentic Era, how AI is changing everyday work. And right now it's totally free. It can explain how AI can reshape work across your entire organization and how businesses like yours can prosper from it.

8:37Ryan Holiday: If your revenues are at least in the seven figures, get this free business guide aligning for the agentic era at netsuite.com slash stoic. The guide is free to you at netsuite.com slash stoic. Now let's go a little bit back in time here. Glutarch'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 like this book. I would throw in Seneca's How to Keep Your Cool 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.

9:21Ryan Holiday: 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 John Robertson's book on Mark Shereus. And then, of course, every leader should read Mark Shereus' 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 mark surrealist writing notes to himself about what he's thinking about what he needs to know maybe in your mba you're reading adam smith wealth of nations obviously important 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.

10:08Ryan Holiday: 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. 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.

10:55Ryan Holiday: Incredibly powerful book. And of course, biography is the best way to learn about how to lead, how not to lead. Chernow'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. 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?

11:33Ryan Holiday: I should have read about it in an interview 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 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 just absolutely incredible and then let's wrap up with some memoirs of great leaders.

12:45Ryan Holiday: Jerry Weintraub, producer, tour manager, etc. for Elvis, Sinatra, producer of Nashville, Karate Kid movies, Diner, Oceans 11, Oceans 12. 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 Zemuri, 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.

13:25Ryan Holiday: Samuel Zemuri 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. 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 minutiae 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 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.

14:58Ryan Holiday: There's nothing wrong with you. 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.

15:37Ryan Holiday: This is what Truman was getting at when he said that not all readers are leaders, but every leader has to be a reader. Okay, so how can you be a better reader? Well, that's what we built the 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, a college dropout, I'm pretty sure it will work for you too. Actually, 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 Surrealist, 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.

16:51Ryan Holiday: So that's what we're doing. And we'd love to have you join us. You can sign up right now, dailystoic.com slash read to lead.