Michael Dell on Calculating Risk and Playing Nice But Winning

Ryan talks to founder and CEO of one of America’s largest technology companies Michael Dell about his new book Play Nice But Win: A CEO's Journey from Founder to Leader, the balance between trusting yourself and trusting the opinions of experts, focusing on what you can control, and more. Michael Dell is chairman and chief executive officer of Dell Technologies, an innovator and technology leader providing the essential infrastructure for organizations to build their digital future, transform IT and protect their most important information. He is ranked 24th richest person in the world by Bloomberg Billionaires Index. He founded Dell Technologies with $1000 in 1984 at the age of 19. In 1992, Michael became the youngest CEO ever to earn a ranking on the Fortune 500. Cometeer partners with the best locally owned roasters in the world and through their breakthrough brewing technology, provides a delicious, high-quality, balanced cup of coffee for a fraction of the price. For a limited time, you can save 20 Dollars off your first order - that’s 10 free cups on your first order, and shipping is always free - but only when you visit cometeer.com/STOICTalkspace is an online and mobile therapy company. Talkspace lets you send and receive unlimited messages with your dedicated therapist in the Talkspace platform 24/7. To match with a licensed therapist today, go to Talkspace.com or download the app. Make sure to use the code STOIC to get $100 off of your first month and show your support for the show. LinkedIn Jobs is the best platform for finding the right candidate to join your business this fall. It’s the largest marketplace for job seekers in the world, and it has great search features so that you can find candidates with any hard or soft skills that you need. And now, you can post a job for free. Just visit linkedin.com/STOIC to post a job for free. Sign up for the Daily Stoic email: https://DailyStoic.com/signupFollow us: Instagram, Twitter, YouTube, TikTok, FacebookFollow Michael Dell: Homepage, TwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:03Ryan Holiday?

  Welcome to the weekend edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring. Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. Let me tell you a story that takes me way back to the first week of March 2020. Obviously, I'd vaguely heard of this pandemic thing, but I was out to dinner with my wife and my kids. And I'm just leaving, I'm walking back to my car to drive to the house, and I noticed I hadn't had my phone on me, and a whole bunch of texts and emails are there. No joke from Michael Dell. "Where are you? Are you coming? What happened? Are you okay?"

• 1:30Ryan Holiday?

  You know, stuff like that. Because I was supposed to have dinner with him that night. Well, not really. So, okay, here's what happened. I thought we were having dinner on the 6th, and I think it was actually on the 5th. I'm trying to remember. I won't say who's to blame. I would say I didn't introduce the mistake, but ultimately, I have to own the mistake, and I missed a dinner, a chance to have dinner, with one of the most successful businessmen in the world, someone whose products I have used for many, many, many, many years. I think my first computer was probably a Dell. And... There I was, not just not going to dinner,

• 2:14Ryan Holiday?

  but flaking and missing a dinner. I was, as you can imagine, completely mortified, so upset and embarrassed, and I didn't know what to do. So this is going to sound like name dropping, but I hope it's just, it is the insane story. So I remembered that Michael Dell and Lance Armstrong know each other, and I know Lance a little bit. And so I said, Lance, I need you to do me a huge favor. You gotta tell Michael Dell that I'm not a piece of crap who just blows off dinner plans. Please reach out to him and tell him that I did not mean to do this, and it was a total accident, and that I am worth giving a second chance to. And then we couldn't have dinner because there we,

• 2:59Ryan Holiday?

  he was like, okay, yeah, we'll reschedule. And of course, we could not reschedule for months and months and months because it was impossible to have dinner because of the COVID-19 pandemic. And I thought there was a chance that I missed my one and only chance to have dinner with someone I really wanted to meet. And anyways, we ended up rescheduling. Many months later, we had an outside dinner at his beautiful home in Austin with his wife Susan and two of his children. And it was just a wonderful experience. I had such a good time. And that leads us where we are today, which is Michael Dell is my guest on the Daily Stoic Podcast. Michael and his son Zach had reached out to me originally

• 3:44Ryan Holiday?

  because they'd read some of my books. And so to hear that Michael had a book coming out, I was very excited to read. If you don't know who Michael Dell is, and this name isn't ringing a bell. Michael Dell is the chairman, chief executive officer, and founder of Dell Technologies, one of the biggest infrastructure and computer companies in the world. He is ranked the 24th richest person in the world by the Bloomberg's Billionaire Index. He founded Dell with a thousand bucks in 1984 at the age of 19, ran it out of his dorm room and college apartment while he went to UT. He was the youngest CEO ever to earn

• 4:24Ryan Holiday?

  a ranking on the Fortune 500. He and his wife Susan, who is a lovely person, established the Michael and Susan Dell Foundation to accelerate opportunities for children growing up in urban poverty in the US, India, and South America. The Dell Foundation also has the Dell Children's Medical Center here in Austin, Texas. He is a wonderful booster and supporter of this town. You can go to dell.org, of course, to read more or follow at Michael Dell on all platforms. But more importantly, he is the author of a new book, Play Nice But Win: A CEO's Journey From Founder to Leader, published also by Portfolio,

• 5:05Ryan Holiday?

  which publishes my books. This idea of playing nice but win is fascinating. I think it's a great way to think about business and life. You want to be successful. You want to do your best. You want to play by a certain set of ethics. But as Mark Suriel says, we can't go around expecting to play to as republic. We've got to play to win as well. And that ties into something that Michael and I talked about at the beginning of the interview, which is another little expression, another little rule that they have over at Dell that we did a daily Stoic email about a few months back, which I won't spoil, but tune in. It's a great philosophical and business conversation between Michael Dell and myself. And Michael, if you're listening, again, I do apologize for blowing that off. That

• 5:49Ryan Holiday?

  never happens. I'm not only don't blow stuff up. I hate being late and I never do it on purpose. And I was so mortified that that happened, but I'm glad we came back around and I appreciate him taking some time out of his very busy schedule to do this interview.

• 6:06Ryan Holiday?

  Hello.

• 6:07Speaker 01

  Hey, Ryan. How you doing?

• 6:09Ryan Holiday?

  I'm doing amazing. How are you?

• 6:10Speaker 01

  Doing great.

• 6:12Ryan Holiday?

  Awesome. Well, I'm really excited.

• 6:15Speaker 01

  I'm excited too. Great to be with you.

• 6:17Ryan Holiday?

  Are you in Texas?

• 6:18Speaker 01

  I am.

• 6:19Ryan Holiday?

  Wonderful.

• 6:20Speaker 01

  I'm in Austin. All right. It's a good place to be.

• 6:23Ryan Holiday?

  It is. This is the best part of the year to be in Texas.

• 6:27Speaker 01

  Exactly. Yeah.

• 6:29Ryan Holiday?

  Well, to start, before we get into the book, which I told you I would read and I loved, I wanted to start with, the title is Play Nice But Win, which is a nice little motto. I wanted to start with a little motto you told me you also have, which I thought might be the title of the book when you told me you were working one, PBNS. Will you tell people what that means and how you try to live that too?

• 6:57Speaker 01

  Yeah, so PBNS is pleased but never satisfied, or sometimes pleased but not satisfied. And sort of the idea behind this is, you know, continuous improvement is important and complacency kills. And, you know, when you're succeeding, it can be really intoxicating and also very dangerous because your brain kind of turns off, right? And so, you know, when you're in an industry that's always evolving, you need to be thinking about what are the future problems?

• 7:39Speaker 01

  And, you know, it's just super dangerous to sort of believe your own nonsense, you know? And I have this, I have this, this cover from Fortune Magazine in my office. And it's, and I'm not on the cover. It's a guy named Ken Olson. And he was the CEO of Digital Equipment. And it says, it says basically, "America's Most Successful Entrepreneur." You know, Ken Olson, CEO of Digital Equipment. In 1986, you know, that was the story they wrote. You know, if you were a digital quip and you believed that, right?

• 8:25Speaker 01

  You know, you were not thinking about all the things that were about to happen in the industry.

• 8:29Ryan Holiday?

  Sure.

• 8:30Speaker 01

  And, you know, so, yeah, I just think it's a really important approach.

• 8:34Ryan Holiday?

  What it's an interesting tension, right? Because I think when we think of like champions, when you think of Tom Brady, you think of someone who's never satisfied, right? Who's always trying to get better, always pushing themselves. But that's also can be, I don't know if you saw the Michael Jordan documentary last year, but also a recipe for misery, both for yourself and for other people in a way. So when I heard that, what struck me about it was the emphasis on the first part, which is also being pleased and happy. Those two ideas need to be balanced out.

• 9:06Speaker 01

  Yeah, yeah. And, you know, I think it took me some time to learn how to appreciate and celebrate our successes. And partly because, you know, when people would bring accolades to me, I was generally skeptical that they wanted something from me. Because they often did, right? And so I kind of just never really needed that. But I figured out that other people did. And it's important to celebrate and, you know, to, yeah, to talk about the successes.

• 9:45Ryan Holiday?

  And one of the stoic ideas that I try to work on, and I'm not perfect at it, is this idea of being very strict with yourself, but also tolerant with others. And so where I think this motto makes sense or is important, I have to imagine in management, which is like, you can be never satisfied with your own performance. But if you're never pleased as a boss, you will grind the people that work for you down into dust. They will hate you, they will hate working for you, and you actually won't get better performance out of them because eventually they'll just go, it's impossible to please Michael. He's never satisfied.

• 10:24Speaker 01

  Yeah, that's absolutely true. And so it is important to celebrate and recognize achievement. And also recognize that every person is motivated by something a little bit different. And you know, when you're running a big organization, you kind of need to have a place where anybody can succeed, you know, no matter what their, their, you know, proclivities and background is.

• 10:53Ryan Holiday?

  So when I was reading the book, it's, it's very rare that the first sentence in a book will provoke the reaction, a reaction in me and yours did because my first reaction, and it doesn't, it eventually gets addressed later in the book, but I remember thinking, I'm supposed to believe that Carl Icahn's wife cooks meatloaf.

• 11:13Speaker 01

  Yeah, well, you know, I, I, I struggled whether I should put that, you know, in, in, in, in the book, but you know, it was really the, the definition of, of Carl as a character.

• 11:26Ryan Holiday?

  Yes.

• 11:27Speaker 01

  And, and how he, how he kind of explained his, his life and circumstance to me that, that brought into sharp clarity, sort of what kind of character he, he actually is. And, um, yeah, I mean, it was a pivotal moment in my process of, you know, trying to take the company private and, uh, you know, I confronted him and sort of started the story out, being, being at his house and, and having, having dinner with him over his, his wife's meatloaf.

• 11:59Ryan Holiday?

  But, but actually to go to the idea of pleased but never satisfied, there's this exchange you have at, at that meeting where he's sort of like, I don't want to, it's jealous, but also like impossible to please. He's, he's like upset that at his son's success, right? And it struck me as

• 12:17Speaker 01

  Oh, yeah.

• 12:18Ryan Holiday?

  Interesting embodiment of like pleased but never, uh, sort of never satisfied where, where it, it just struck me like it must not be fun to be Carl Icahn's son or wife, you know, also what you have him say about his wife's cooking doesn't seem, uh, like the nicest dude either.

• 12:36Speaker 01

  Yeah, and I normally wouldn't go there, but, but, you know, he sort of attacked me and eventually I had to sort of respond in some way. But, you know, the, the, the way he, he talked about his son was, was particularly disturbing to me. Because, you know, you know, as, as a father, and I've heard you talk about, you know, being a father and fatherhood. I mean, kind of the, the thing you hope, you know, most for is that your children are successful, right? And then, you know, and even, even more, you'd like to be surrounded by grandchildren, right, that love you, right?

• 13:13Speaker 01

  And so, yeah, it was, it was a pretty striking, um, you know, way in which he kind of dealt with the whole concept of his son actually doing something that, that was working.

• 13:28Ryan Holiday?

  Yeah, it was, it was very, it was very surreal. Well, let's, let's back up, let's talk about the acquisition, because that's how you open the book and talk about it. And I, I thought about this actually a little bit when I was writing my book on ego. There is something, it's kind of an interesting metaphor, the idea of like, taking a company private or, you know, buying back shares of a company on the open market. Obviously, some people do this for financial manipulation reasons, or sometimes it's a sign of a lack of innovation in a company. But it also struck me metaphorically as this idea of like, the market, which is supposed to be this all-knowing, efficient thing, is saying X, right? It's saying that you are worth X.

• 14:11Ryan Holiday?

  And there require either a delusional amount of ego or a very evidence-based form of confidence that is able to say, actually, we're worth X plus 20%. Or that, that in the future, we're going to be worth 3X, or whatever, whatever it happens to be. Walk me through how you get to a place where you feel like you know more about something than the, all the smartest people in the world, ostensibly, like, and then, and then are willing to, to take that bet. And in this case, one of the biggest bets, or I think at the time, the biggest bet in the history of tech.

• 14:53Speaker 01

  Well, first of all, you have to say you never know for sure, right? You just kind of have an idea or a hunch. And what was happening then, and I think this has happened a couple of times during my career, the popular narrative had kind of swung too far. And the popular narrative at the time was that smartphones were everything. And the smartphone and the tablet were on the rise and the PC was dead. And we're never going to use PCs anymore. We'll just use smartphones.

• 15:33Speaker 01

  And while it's true that there are 5 billion smartphones in the world, we're actually shipping way more PCs than we've ever shipped. And people continue to use PCs as part of their productivity. But more than that, we were investing in lots of areas way beyond the PC, in software and services and security and all these things. And the market sort of didn't really buy it or understand it. And we wanted to transform the company. And when you're a public company, you're kind of on this 90-day shot clock, right?

• 16:14Speaker 01

  And so by going private, we were able to free ourselves from that 90-day shot clock and accelerate the transformation. Our public shareholders got a significant premium to the price of the stock without having to take any of the risk. And we got the chance to roll the dice, as it were, and get very aggressive and hire thousands of additional engineers and salespeople. And then a couple of years later, we did the biggest merger acquisition ever in technology and come out a transformed company.

• 16:53Ryan Holiday?

  Yeah, it's not obviously the courage of running into a burning building or something, but that must have been a deeply scary thing to do, to essentially go all in. I mean, as you say a couple of times in the book, where you're actually negotiating this from your house in Hawaii, you must have thought, I could just hang out here. I don't have to do any of this. Instead, you're going all in and yeah, one of the biggest transactions in history, which no one can guarantee you is going to succeed. In fact, it may end disastrously.

• 17:25Speaker 01

  Yeah, I mean, I wouldn't have done it if I thought it was going to fail. And I thought the downside was actually pretty limited. I mean, just being objective, I mean, this is a company that had for a long time generated very strong cash flows and tons of revenue. And while it was true that the smartphone was, you know, playing a bigger role in technology, you know, I just thought the popular narrative had run too far. So even if we hadn't grown, you know, we could have done quite well, paid off a lot of debt, had a lot of flexibility.

• 18:06Speaker 01

  You know, it turns out we did way better than we thought and, and, you know, it all worked out, you know, really well. And actually, the, there was another popular narrative that came, which was that everything was going to the public cloud. And while it's true the public cloud was growing, you know, things like the edge, where everything in the physical world is becoming intelligent, and this idea of multi-cloud have emerged. And, you know, that was kind of what enabled us to combine with EMC and VMware and You know, create even more opportunities. So kind of made a bit of a career in going against,

• 18:50Speaker 01

  you know, popular narratives that have swung too far.

• 18:54Ryan Holiday?

  I remember when I was talking to Peter Thiel, he said something about his investing strategy, which was like, what do I know that they don't know? Right? And so maybe it's like, the narrative is this, and if the narrative is true, obviously you listen to the narrative. But if you have some sort of, it's not the same as inside knowledge, but you have some sense or deeper experience that lets you know that there is something wrong with the narrative, then you feel confident making the bet that you're making because you know something that the people who believe in the narrative don't know, or have willed themselves not to see.

• 19:29Speaker 01

  And it's not as if we were acting with secret information either, right? I mean, you know, if you go back, you know, I was giving speeches in public in 2012 and talking about everything we were doing and why it was important, why I believed it would work. But, you know, market didn't, didn't agree with me. So, you know.

• 19:49Ryan Holiday?

  Right. Yeah. What's that, that thing like, don't worry about people stealing your ideas. You'll have to ram it down their throats. Like you, you were public about it and then people still doubted you. And then I think about that as a writer, like, because you know, you, and you probably went through with your, your book and we're both at Portfolio is like, you do the book and then you get a bunch of notes and how do you decide what notes to listen to and what notes not to listen to? Right? And, and I think this is true in life. You get feedback. How do you know if the market is, sometimes the market is saying X and it's true. Sometimes the market is saying Y and it's, it's actually X. And so how do you know what to listen to if it's just, I always trust myself, you know, you're going to be right

• 20:33Ryan Holiday?

  sometimes and then terribly wrong other times. And then also, if you always listen to what other people say, you're probably going to be far too conservative and risk averse and, and wrong in a lot of other ways.

• 20:45Speaker 01

  Yeah, and in the market, it's never binary. There's always like degrees of of all these things. And, you know, I think having big years and listening and being reflective and spending a lot of time with our customers, you know, you you know, you feel like you you have some some understanding of what's what the situation is.

• 21:09Ryan Holiday?

  And then maybe that's where you get to the title, which is, okay, you're right, you're you think you're right. And then you put out what you think is a fair you try to do it. And then, of course, life is much more complicated than just simply being correct. Then you then you get in a street fight about it. And the one who emerges victorious is is the one who is who is right.

• 21:33Speaker 01

  Yeah, I wasn't expecting all that to happen. And it turned out to be way more complicated than than I thought. But, you know, in the end, it all it all turned out well.

• 21:42Ryan Holiday?

  Well, so don't you find that people and maybe this is why you have the motto is people sometimes think that being right is enough, or that having a good idea is enough, or that, you know, having a good product is enough. It also is that street fight like you do have to go toe to toe with the Carl icons, or you do have to buck a bunch of people telling you you're wrong, or any of that. It's always more complicated and more difficult than it probably should be.

• 22:15Speaker 01

  Yeah, that's right. And, and, you know, you know, when when I was going through it, and you know, it's kind of reminded of the Winston Churchill, you know, if you're going through hell, just keep going, right? It's like, you don't really have any choice. I mean, you know, you could you could give up or stop, but that wouldn't be the right answer or outcome. So you just keep going. And every day you wake up and figure out what's the most right next step to be taking to get to where you want to go.

• 22:53Ryan Holiday?

  But so how do you manage that when you are against someone or in some industry where either it's rigged or people are fighting quite unfairly? Like it seemed like just from the way you talk about it, it really bothered you, the way people could just sort of go on television and lie about things. And then you were forced to both respond and address that as if it was the same as playing fairly. Like, how have you found over the years that you navigate sort of tricky terrain like that?

• 23:27Speaker 01

  Well, and of course, the reason for it was he was a magnet for the media, right? And he was entertaining. It's not that they actually agreed with what he was saying.

• 23:35Ryan Holiday?

  Sure.

• 23:36Speaker 01

  People watched him because, you know, it was like a dumpster fire or something. It's like really interesting to watch him just mouth off about all this stuff.

• 23:46Speaker 01

  You know, which is why I ultimately decided to confront him face to face because I wanted to, you know, understand, you know, what was he really thinking? It turns out he wasn't really thinking much of anything. And so then, you know, I knew it would still be a grind, but, you know, I knew, you know, he wasn't going to make good on any of the ridiculous, you know, promises or claims that he'd thrown out there. So it was kind of just, just, you know, letting the truth ultimately, you know, bubble itself up and,

• 24:24Speaker 01

  and, you know, persevering, outlasting him, and also, you know, kind of calling his bluff and telling him, okay, you know, hey, if you want to do it, go right ahead. You're going to screw it up, by the way, and then I'll come back and buy it from you at a lower price. And, you know, that was when I saw he was, he was truly terrified. And, and, you know, that gave me a better understanding of what I was dealing with.

• 24:53Ryan Holiday?

  Yeah, some of these characters that maybe we hear about on television or we see, you know, We read about or we think live these sort of glamorous or interesting lives. I'm sure you've met your fair share of them. And then you sort of you get to peek behind the curtain and you kind of go, oh, it's probably not actually fun to be that person or that they're almost acting under a kind of compulsion or addiction, or they just like they can't stop. They just sort of are who they are. And what you see, there's that that expression that character is fate. It just sort of this is who they are. This is how they'll always be. And you sort of just have to leave them as they are.

• 25:33Speaker 01

  Yeah, I mean, this is kind of a sad human being. And, you know, I think I think his, his, his challenges not to psychoanalyze probably came from the way his father treated him, based on what he told me. But, you know, at this stage in his life, he probably should be doing other things to to help others, but that's not what he's generally doing.

• 25:58Ryan Holiday?

  But that but that also goes back to the idea of pleased but never satisfied is that often the person who is like, let's say, early on, you pick up some idea that like, to to to make my dad proud, I just always have to do X, Y, or Z. Or that like, if if I ever stop trying to get better, you know, people will laugh. And we can pick up these sort of early compulsions that can be quite adaptive as far as making us deeply specialized and talented at a singular thing. And then they sort of get us there, they get us to the top of a certain mountain. But at what cost?

• 26:36Speaker 01

  Yeah, yeah. Can't can't argue with that.

• 26:40Ryan Holiday?

  But you but I mean, I don't know you super well. You you do seem to be for one of the richest, most successful people in the world who employs hundreds of thousands of people. You do seem to be fairly well adjusted.

• 26:57Speaker 01

  I hope so, you know, um, yeah, I mean, you know, I, I've, you know, don't, I, I don't think I've, I've changed, uh, you know, a lot of my super core beliefs, uh, you know, from, from, from when I was, you know, let's say in a, in a, in a, in a less fortunate position. Um, and yeah, I continued to learn and, and grow, but, but yeah, I think I've kept my feet on the ground and, and focus on, on the right things.

• 27:31Ryan Holiday?

  How much of that is your wife? I mean, you've been married for what 30, 32 years, something like that?

• 27:35Speaker 01

  32 years. Yeah. I think it's, I think it's a, I think it's a big part of it, you know, having that,

• 27:43Speaker 01

  actually tomorrow's our 30, 32nd anniversary.

• 27:46Ryan Holiday?

  Congratulations.

• 27:46Speaker 01

  Thank you. Uh, having that strength of relationship and having her as a thought partner and a sounding board, you know, against all the things that are going on in not just my life, but our collective life together, uh, has been, has been incredibly important. And, you know, she, she has tons of unique insights and perspectives that, that, you know, I don't have.

• 28:12Ryan Holiday?

  I imagine it's also the continuity and the consistency that helps keep a person grounded. You know, it's like as one becomes more and more successful, you can sort of cast off certain things or level up in certain things, but you become untethered as a result because you are, you, you've lost sort of who you once were, or what was once important to you. I'm sure you've seen that many times with people that you know.

• 28:39Speaker 01

  I've seen that happen with, with others and, and, uh, you know, I, fortunately I don't think I've, that's not the path I've taken.

• 28:48Ryan Holiday?

  Yeah. Well, and, and then, you know, when you're with someone for a very long time, they have the ability, no matter who you are, what you've done, to call you out on your bullshit.

• 28:58Speaker 01

  Yeah, and you know, I'd say the same for some of my other family members, right? You know, my, my brothers, my, my dad, other, other, other family members, you know, that, that, you know, have known, known me pretty much my whole life. So I, I think that's, that's, that's super important.

• 29:15Ryan Holiday?

  Well, how much is staying in one spot also done that, right? Like, I'm sure you could be based anywhere in the world, but you're still sort of right where you started.

• 29:28Speaker 01

  Yeah. Um, you know, it's, it's, it's, it's home. I, I love, I love Austin. Uh, it's, you know, I came here when I was a freshman at UT and fell, fell in love with the place and never, never thought of really leaving.

• 29:46Ryan Holiday?

  Yeah, yeah. Um, I, I liked the story in the book about, you know, your sort of, your parents and they're struggling to understand just what the hell you were doing in your, in your dorm room.

• 29:59Ryan Holiday?

  Why do you think, and now that you're, you're a parent, um, and all, all your kids are out of college now, right?

• 30:05Speaker 01

  Yes.

• 30:06Ryan Holiday?

  So did it give you more empathy for your parents and their struggles to understand, uh, you wanting to leave college or not taking college seriously?

• 30:19Speaker 01

  Oh, yeah. I mean, no, I totally understood how my parents thought about it. I mean, you know, they were the first, you know, of their generation to, to go to college. Right? And, and so the idea of giving up this opportunity for an education just was a total anathema to them. And so they, they're like, you gotta be out of your mind, right? To, to be thinking about it that way. So I, I totally understood that.

• 30:50Ryan Holiday?

  Yeah, it's just, it's the irony of like, you're making hundreds of thousands of dollars a month. And they're like, but why aren't you going to chemistry class? Or whatever it is, right? Like, there's this sort of, I think as a parent, you probably just want your kid to be safe as opposed to maximize their potential or fulfill their dreams.

• 31:11Speaker 01

  Yeah, and ultimately, what I figured out was that you could take a semester off and go back to college.

• 31:17Ryan Holiday?

  Yeah.

• 31:18Speaker 01

  With no academic penalty. And so I kind of convinced them that that was okay. We sort of, you know, developed a bit of a compromise.

• 31:26Ryan Holiday?

  Yeah, I remember when I decided to drop out of college, I went into the registrar's office to drop out. I went to the University of California, Riverside, so similar to UT. And, and, and I remember going and being like, I'm here to drop out. And they were like, you don't have to do that. You can just, you can just take a break and come back whenever you want. So this sort of decision that was so terrifying to me and sort of so life altering, it was like, I only had to do 10% of the, the risk. You know what I mean? It, you, you, I think you often think these things, it's like, hey, I'm going to end up living under a bridge somewhere if I make this decision. But in fact, when you really get up and close with those risks, and maybe this is what you were saying about buying Dell back,

• 32:10Ryan Holiday?

  that it's not actually as potentially catastrophic as it might feel when you haven't really kicked the tires.

• 32:17Speaker 01

  Yeah, and, and for me, you know, I mean, if I had, if I had not started anything and didn't have this business sort of thriving in my dorm room, then dropping out of college might have been a pretty big risk, right? But, but, you know, I had derisked it pretty significantly and I felt confident, you know, I could 10x the business, you know, just by sort of moving from my little tiny dorm room, you know, into a, a little tiny office.

• 32:44Ryan Holiday?

  Well, that's kind of the weird mythology about dropouts, whether it's like Steve Jobs or... Well, Steve Jobs actually kind of was a dropout. But when you look at like a Bill Gates or a Mark Zuckerberg, they weren't just dropping out to go find themselves. They had businesses that in some cases were making millions of dollars. Like, they had employees and they were like, I can't go sit in a classroom. I have, I have staff meetings all day.

• 33:08Speaker 01

  Exactly. Yeah.

• 33:10Ryan Holiday?

  So I think people think dropping out is this hugely risky thing, which as you said, it is if you don't know what you can do instead. But if you know what you can do instead, it's a very different thing.

• 33:21Speaker 01

  Yep, precisely.

• 33:25Ryan Holiday?

  When you think about, because again, to go back to Icon, it seemed like it was also the way you were sort of setting it up is a sort of a contrast of approaches to life. Sort of like you're a builder and then there is also a type of person who is very successful, but doesn't actually make or do anything. It seemed like maybe what you really objected to was the sort of financial engineering of it as opposed like it seemed like he was utterly indifferent. And this may be what you talked about in that meeting. It's like, like, what's your plan? And he's like, I don't know, I have people like the idea that Dell was a company comprised of human beings who make things seemed to be more

• 34:08Ryan Holiday?

  your style and not the style of the people you were up against.

• 34:12Speaker 01

  Yeah, to him, it was a poker game, sort of a form of entertainment, you know, and something that he kind of had fun doing. And to me, it was much more, right? It was like people's lives and what we're doing really matters in the world. You know, I carry, you know, in my conscious, you know, this pretty heavy burden of all the people that I'm in some way responsible for. And it's not a poker game, right? This is like super important stuff. And, and, you know, you can't just go on TV

• 34:55Speaker 01

  and lie about things. And, you know, the negative impact that that has on people's psyche and on, you know, actual real outcomes, you know, just didn't really appreciate, you know, his, his, his approach at all.

• 35:14Ryan Holiday?

  Yeah, like we're obviously in the middle of some, some discussions as a country about taxation, for instance, and it does strike me that we do a bad job distinguishing between sort of people who make things and people who make lots of money. And that those, those are obviously different, but both can be paths to wealth, but that like...

• 35:36Ryan Holiday?

  We obviously, and we saw this during the pandemic, and we're seeing it now with these logistical issues and all that. It's like, we really do need people who make things, who know how to do things, who can solve hard problems. And that that is, that is different than just, say, people who are good at moving numbers around on spreadsheets, or are good at, you know, playing poker. But, but that builders are a really important part of making the world work.

• 36:04Speaker 01

  Yeah, and maybe I'm biased, but I think we need more of that in the future. You know, and if you think about all the sort of big challenges that are out there in decarbonization, energy, you know, environment, you know, healthcare, you know, et cetera. You know, these are some pretty big challenges to go after. And you're going to have to have some bold, risk-taking entrepreneurs and, and capital to fund them, to be able to, to go solve those problems. And we should be kind of proud that we have a fair number of those

• 36:44Speaker 01

  here in this country. I'm not looking for accolades, but, but I do think, I do think a lot of countries would really crave to have more of them. You know, not, not, not, not, not less of them.

• 37:01Ryan Holiday?

  Yeah, I'm not the, the world's biggest Ayn Rand fan, but the, the premise of Atlas Shrugged is I don't think you want to live in a world where all those people go away.

• 37:10Speaker 01

  Yes.

• 37:11Ryan Holiday?

  But, but why do you think we struggle, why, why do we struggle to solve tough problems? Marc Andreessen wrote that essay at the beginning of the pandemic about building things. Why do you think the, the most successful, sort of most naturally risk-rich in resources country in the world seems to, it's not that we have an innovation problem, because we're brilliantly innovative in some ways, but we seem to lack the ability to solve tough problems. Obviously, the vaccines are a great example of what it looks like when it goes right. But then we also seem to be able to not solve the, the tough psychosocial issue

• 37:54Ryan Holiday?

  of like, getting people to take them, right? But why do you think we're struggling to solve these tough problems, whether it's climate change, or whatever?

• 38:04Speaker 01

  Well, first I'd say I don't know. But I think there are parts of society where there's more government involvement and more regulation, and I think those are areas where you tend to have less innovation. So if you take education and healthcare as two obvious examples. These are areas where the government's very involved and there's a lot of regulation and you don't have a lot of innovation. So just an observation.

• 38:39Speaker 01

  So I think, as a full red-blooded capitalist, I'm more in the camp of let's let innovation solve a lot of these challenges. I don't think government is going to address many of these challenges. There's a role for government to play, but if I look at the things that we're doing and thousands of companies are voluntarily doing in some of the big challenging areas

• 39:19Speaker 01

  like in decarbonization, I think that's actually going to move the needle much more than government regulation.

• 39:29Ryan Holiday?

  Yeah, I had R.C. Buford on a few weeks ago and we were talking about Adam Silver, so the idea of government versus private. I was like, why can't Adam Silver be in charge of everything? He seems like he's done a hell of a job.

• 39:43Speaker 01

  He has done a great job and dealt with many crises and geopolitical issues. And yeah, it's complex and...

• 40:02Ryan Holiday?

  Well, it's like, it's like we're not sending our best, right? We clearly have the talent. We clearly have the capital. I was just thinking about this because so my, my oldest turns five in two weeks. So he'll just right. So basically right when he turns five, then he'll be eligible for the vaccines, which are just about to roll out for kids. And so obviously I've been following the news on it and it was like, you know, like this was at the beginning of October. It's like, you know, FDA is set to meet about the approval of vaccines for kids and blah, blah, blah. Pfizer turns in the data in, you know, late September and the FDA is like, okay, we'll meet about it on October 26th. And, you know, just like, who sets a meeting four months, you know, four weeks from now in the middle of a, in the middle of a pandemic?

• 40:46Ryan Holiday?

  And it did strike me as a contrast between sort of the private and the public approach of like, uh, what makes you think you can afford to take four weeks, right? And sort of the play nice, but win. Obviously you gotta be accommodating the people's schedule, but also get your ass in gear, kind of a thing.

• 41:07Speaker 01

  Yeah, and, and I, I had the same frustration, you know? Unfortunately, I don't know what we could do about it.

• 41:15Ryan Holiday?

  Yeah.

• 41:16Speaker 01

  You know, given, given the democratic system that we have, um, which, which, uh, as much as we might say it could be better, um, you know, uh, people still want to come to this country and I still think it's the greatest country in the world, you know, by, by, by a lot. But you can certainly see some other systems out there where, you know, they have, uh, a deterministic strategy. They're, uh, investing in strategic industries in, in aggressive ways and they're advancing quite rapidly. And, you know, I think it's, I think it's good that you're starting to see, you know,

• 41:58Speaker 01

  the, the, the American government start to focus on things like semiconductors, like Duh, hello. You know, these are important things. These strategic industries that play a role in so many aspects of the future. And if we just give up on those and we get hollowed out by other nation states that have a more deterministic, you know, strategy around those, that's a super dangerous thing, you know, over, over a long period of time.

• 42:32Ryan Holiday?

  Yeah, it's, yeah, playing nice, but, but, but trying to win also that you can't just expect these things to take care of themselves or problems to resolve themselves. You do have to, to sort of fight for the important things. And bureaucratically, we seem to struggle with, yeah, what deterministic thing, it was sort of what is, what is the outcome that we're trying to achieve and let's back it out from there, not simply follow the process that we have always followed.

• 43:04Speaker 01

  And, and there are also things that have a duration which is well outside the boundaries of the next election or cycle or two. And so they require a, you know, a level of, of thought and planning that, you know, we don't seem to be really great at.

• 43:24Ryan Holiday?

  Well, so actually, let's, let's take that back to Dell then, because you have experienced it in all the different ways. You were, you were talking if the election is a sort of shot clock, right? And you were saying you were stuck on a 90 day shot clock, then you went private, now you're public again. How have you thought about managing this shot clock, which is a real constraint, just as the ways midterms are a constraint and presidential elections are a constraint. And then in politics, they're all overlapping with each other. But how, how do you, how do you think about it? And how could we do a better job? Thinking long term within these short term constraints.

• 44:05Speaker 01

  Yeah, I think as for companies, you know, there are times in various market cycles and in the life of a company where the market may or may not give it permission to think with a longer term time horizon.

• 44:23Speaker 01

  We're in a better place now and we're able to do that and you know, it's, it's working well.

• 44:30Speaker 01

  But you know, there's no guarantee that'll continue and, and the market definitely goes through cycles. We, we, we had a, we had a tough time, you know, 2012, 2013.

• 44:43Speaker 01

  You know, there, there is, there is a lot of risk capital out there that is, that are funding big hard tech problems and that's, that's certainly a reason to be very optimistic about the future of not just, you know, the US but, but the world.

• 45:01Speaker 01

  But you know, this, this question of, of how does the, how does the system of democracy, you know, address those kinds of challenges? I think, I think first, first of all, it, it takes, it takes bipartisanship, right? Which, which isn't a ton of. I think one of the things that happened in the, in the, you know, the last five years or so was a greater understanding of the threats, you know, of, of China specifically, you know, to, to, to America's continued growth and success.

• 45:43Speaker 01

  And that I think is leading to, you know, some of the investments around semiconductors, which are a good thing and hopefully we'll see more of that. And it, and it's been a much more bipartisan agreement that it's a national priority. It's not, you know, sort of a, a, you know, a blue party or a red party kind of a thing.

• 46:06Ryan Holiday?

  Well, maybe it's just, yeah, what do we decide to focus on, right? You look at some countries, a lot less innovative than America. And you know, you can get a COVID test for a dollar at a grocery store in Germany. Meanwhile, to get your results back on a PCR test in America, it takes three days. You know, two years into the pandemic. And it's because, you know, we decided to get bogged down in this mask discussion instead of innovating our way out of the, not that masks are not important, obviously they are. But you know, we, it's like, we seem to get locked in on these intractable like issues where 50% thinks this and 20% thinks this. And you know, 30% doesn't care.

• 46:45Ryan Holiday?

  Instead of focusing on sort of alternative solutions to the whole discussion entirely. It seems weird how we get stuck in these, in these quagmires.

• 47:00Speaker 01

  Yeah, again, you know, I'm not really sure what to do about that. And, and, you know, we, we try to, try to stay out of things that, that we can't do, do, you know, do a whole lot about.

• 47:17Ryan Holiday?

  Yeah, yeah, I just mean, to me, the lesson from that is like, what are you going to choose to focus your attention on? Is it going to be on something you don't control? Or is it going to be something that you, you might have some, some, some, as, as our mutual friend Matthew McConaughey says, where you have some green lights, right? Like, are you going to focus on, on where you can get some momentum going? And I think strategically is we get stuck on like, what's right, you know, or what I want as opposed to, well, what are the most, what are the actual possible solutions to this problem that would allow us to move forward in some way?

• 47:56Speaker 01

  Yeah, and we focus on the things we can control and where we can, where we can make a difference and, you know, where we think. Technology, specifically our technology can help, you know, democratizing access and, you know, opening up the, the, the opportunity set. I mean, there's a lot of work going on, on 5G and broadband. And we kind of saw during the pandemic, you know, the kind of fault lines in our society where some people weren't connected, they didn't have the right devices, and they couldn't access education or healthcare or, you know, their jobs or entertainment or

• 48:39Speaker 01

  anything else. And, you know, that's something we can actually help with, right? And, and so, you know, we're, we're focused on that.

• 48:48Ryan Holiday?

  Yeah, I mean, I'm, I'm at my bookstore right now, but, but where I live, which is like 30 minutes from you, I, I have broadband, satellite broadband that downloads at like 10 kilobytes a second. I could barely stream Netflix. I, I could almost see downtown Austin from my place, and I am, you know, buffering on reruns of The Office because the, the digital divide is still literally, you know, you know, divided in some cases. People just don't have access to these, these basic things, which again goes to the point of like, how can we not innovate our way out of these problems? These seem like if any country could solve it, it should be us.

• 49:31Speaker 01

  Yeah, I think we can innovate our way out, out of these. And, you know, I think, I think the government can play a role in catalyzing, you know, you know, some of that.

• 49:43Ryan Holiday?

  Yeah, I think about that. Have you read the Robert Caro series on Lyndon Johnson?

• 49:47Speaker 01

  No.

• 49:48Ryan Holiday?

  Oh, it's, it's epic. It's obviously, I think, some of the best books ever written about Texas. But this is where Johnson makes his name as a politician, is that like, the Texas Hill country just didn't have electricity until like the 40s. And because they basically, both government and business was sort of like, we don't care about these people, right? Like, they, they don't vote, they don't have any money. What do they matter? And, and Johnson uses... His bureaucratic competence to wield the levers of power to solve an intractable problem. And so, you know, he becomes this sort of political hero in Texas because he brought lights to and and electric power to people, you know, well after everyone

• 50:33Ryan Holiday?

  thought this was solved. But of course, it wasn't solved. And, and, uh, yeah, we, we were just driving across the country. We visited that we drove over the Hoover Dam. And you're just like, man, we used to do some crazy things as a country. We don't do that much of that anymore.

• 50:49Speaker 01

  And we did them a lot faster too than than than we do them now. Um, so yeah, I mean, I think, I think there, there, there are a lot of protections in place. There's a lot of friction and not all of it is helping us, you know, build the future that we need.

• 51:09Ryan Holiday?

  But do you think part of it is also that it's just so much easier to build an app or a website? And in many cases, so lucrative that some of the best talent of a generation has been misallocated towards maybe superficial problems? Like, like instead of having engineers who are designing the next Hoover Dam, they're designing algorithms that make you more angry at your neighbor at Facebook, you know, on Facebook?

• 51:41Speaker 01

  Yeah, the confirmation bias reinforcement algorithms. Yes. I mean, I think that the that's been very lucrative. And certainly whatever is lucrative often attracts, you know, uh, you know, a number of the top talent and top graduates. But, uh, you know, I think there's also another thing going on, which is more and more people are looking for more meaning in their life and more purpose. And, you know, they are attracted to these more noble and and meaningful, you know, endeavors. And so, yeah, I guess I remain optimistic that we won't have a problem.

• 52:25Speaker 01

  Attracting the best and brightest if the necessary conditions are there to allow them to succeed. And again, I go back to, there is an enormous amount, you know, there's never been as much funding as there is now for huge, complicated problems to be solved, even with all the, you know, challenges and obstacles that are out there.

• 52:53Ryan Holiday?

  So how do you think about that philanthropically as you decide where you're going to direct time or resources? What, what problems excite you as being problems? One, that you think can be solved and two, you think you can contribute or your foundations can contribute to solve it?

• 53:16Speaker 01

  Yeah, we, we focus a lot on children in urban poverty, which takes us to education and improving the education system, you know, bit by bit, you know, and, and piece by piece. And also in healthcare and, you know, healthcare outcomes, family economic stability. And, you know, how do you, how do you change the life trajectory that somebody's on and help them get on a, on a completely new path? And, um, you know, I think, I think, I think philanthropy can play a big role there and we're, we're, we're doing a lot there.

• 53:59Speaker 01

  I also think what's interesting is you're seeing a lot more for-profit businesses that have a social, you know, purpose as their, as their underlying, you know, objective. And in many cases, those for-profit organizations are moving the needle even more than the philanthropic ones. And so it's a combination of, of, of, of factors that, that, you know, I think will, will, you know, will ultimately drive, drive progress.

• 54:33Ryan Holiday?

  Yeah. So something like the Dell Children's Hospital, what do you think about when you decide to endow something like that? What, what is, when you, let's say flash forward 20 years and it's a success, what does that success look like to you?

• 54:50Speaker 01

  Well, in that case, it was it was pretty straightforward, right? Um, you know, the the city has been doubling in size every decade for four decades.

• 54:59Ryan Holiday?

  Yeah.

• 55:00Speaker 01

  Which is kind of amazing, you know?

• 55:02Ryan Holiday?

  It doesn't seem like it's slowing down.

• 55:03Speaker 01

  Yeah, 250,000, 500, a million, 2 million, 4 million, just kind of keeps going. And so the the capacity for the healthcare system, you know, wasn't keeping up. And certainly, if a child or an adult had any serious medical condition, they're going to Houston or Dallas. That's just the way it was.

• 55:26Ryan Holiday?

  Sure.

• 55:27Speaker 01

  And um, that wasn't great. And, you know, uh, so it it was kind of an obvious place where there was a need. And we also felt that, you know, I mean, Austin was kind of the biggest city in the country that didn't have a medical school also.

• 55:46Ryan Holiday?

  Really? Okay.

• 55:47Speaker 01

  And and it also had this great university, University of Texas at Austin. Uh, and and so, you know, the the Children's Hospital and the Pediatric Research Institute that that we helped create, in some ways, were precursors to ultimately creating a residency program and then ultimately a a medical school. So this has been kind of like a like a 20-year-plus plan to improve the the healthcare infrastructure and attract, you know, world-class academics and and, you know, care providers, uh, and and also create this ecosystem of biotech companies that's starting to spring up.

• 56:30Speaker 01

  So, um, yeah, it's been it's been fun and and it's, you know, certainly something that, you know, the the the community has needed. Uh, and and I'll tell you, um, Every so often, Susan and I will get a letter from a parent. And these are like the most meaningful letters you ever get. You know, when you understand how a place like a children's hospital affects you know, a single child's life. You know, it's just, it's just super touching.

• 57:07Ryan Holiday?

  I do think that's one hopefully good outcome that comes out of the pandemic. I was reading an article that was basically saying that sort of post the Second World War, America especially took a very individualistic approach to healthcare. You have your doctor, you take care of yourself, you do what you want to do. Because we'd solved a lot of the big sort of public health issues. And the pandemic is sort of serving as a reminder that that health is also public health and vice versa. Right. And that the way that we are tied up together, even though we maybe live very different lives or in very different socioeconomic brackets,

• 57:52Ryan Holiday?

  that, you know, the position of the most vulnerable or the least affluent parts of society expose everyone else to risk, that our fates are all tied up with each other. And I do hope we take from this, we carry that energy forward. Because when everyone's in their silo, it might seem like you're taking care of yourself. But you're, you're also putting yourself at risk as a result.

• 58:23Speaker 01

  Yeah, I think, I think one thing we can, we can hope for is that, you know, there's been a, you know, an outbreak of empathy, you know, among, among humans, as we've kind of seen, seen the challenges that everyone has faced. And how can we, how can we, you know, help each other and, and, you know, create, create a, you know, create a better world?

• 58:48Ryan Holiday?

  Well, just how interdependent we all are with each other when suddenly.

• 58:55Ryan Holiday?

  People, you are reliant on people to do things either because you can't do them yourself or you don't want to do them yourself. And you go, oh yeah, somebody has to do this. And it's probably not fun to be them. And it's probably hard, you know, not to have these things that I take for granted, whether that's healthcare or, you know, childcare or any of these things that we just assume everyone has, you know, they, they don't. And it makes their life very hard. And as a result, you know, puts potentially everyone at some kind of a risk.

• 59:29Speaker 01

  Yep. Agreed.

• 59:32Ryan Holiday?

  Well, this was so awesome. I was really glad to talk. I loved the book. I particularly loved, maybe that's the last thing, I love the appendix, the things I believe. What made you decide to, to put the, this, what is it, 21 commandments at the end? Do you, did you have to think of these for the book? Or is this something that you have organizationally or in your office? Like, how do you think about that?

• 59:58Speaker 01

  You know, as, as I was working on the book, um, you know, it, it occurred, it occurred to me that it'd be a good idea to, to have something like this, you know, toward, toward the end of the book. Um, and so I just kind of refined it and honed it. I mean, anybody who's worked at our company could probably recite all of these in one form or another. Um, and, you know, uh, but they, they're, they're definitely, you know, as I said, I think the kind of principles, things I believe, ideals. And, uh, yeah, they've worked well for me. Your mileage may vary, but, but, uh, um, you know, uh, those are,

• 1:00:40Speaker 01

  those are the things that, that, you know, that, that, that, that, you know, I believe are, are super important.

• 1:00:47Ryan Holiday?

  Yeah. My favorite was 13, confidence, not arrogance, humility, not ego, which sort of goes to the, the betting on yourself thing that we were talking about. If you're betting on yourself out of ego, it's probably not going to go well. But if you're betting on yourself because you have a strong sense of both the strengths and weaknesses of your position, that's maybe a good place to be.

• 1:01:07Speaker 01

  Yep. Agreed.

• 1:01:09Ryan Holiday?

  Love it. Well, I hope to see you soon.

• 1:01:11Speaker 01

  Absolutely, Ryan. Hey, great to be with you. Stay well.

• 1:01:14Ryan Holiday?

  That's awesome. All right. I'll let you go.

• 1:01:16Speaker 01

  Okay. Thanks. Take care.

• 1:01:19Ryan Holiday?

  Hey, it's Ryan. You know, the Stoics in real life met at what was called the Stoa, the Stoa Pochyle, the Painted Porch in ancient Athens. Obviously, we can't all get together in one place. First off, because this community is like hundreds of thousands of people and we couldn't fit in one space. But we have made a special digital version of the Stoa. We're calling it Daily Stoic Life. It's an awesome community. You could talk about, like today's episode, you could talk about the emails, ask questions. That's one of my favorite parts, is interacting with all these people who are using Stoicism to be better in their actual, real lives. You get more Daily Stoic meditations over the weekend, just for the Daily Stoic Life members. You get quarterly Q and As with me. You get a

• 1:02:04Ryan Holiday?

  cloth-bound edition of our Best of meditations, plus a whole bunch of other stuff, including discounts. And, this is the best part, all our Daily Stoic courses and challenges totally for free, hundreds of dollars of value every single year, including our New Year, New You Challenge. We'd love to have you join us. There's a two-week trial, totally for free. Check it out at DailyStoicLife.com.