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Back to school starts now. Get long lasting battery life on the Dell XPS laptop powered by Series 3 Intel Core, so you can work from anywhere. And now, starting at $699 with exclusive student pricing starting at $599. It's lightweight, portable and packed with enough processing power to make multitasking a breeze. So say goodbye to distractions and hello to more free time. Because you finished your work faster. Complete your setup with savings on select monitors and more. Must have electron and accessories, limited time deals and free shipping on PCs and more await you at Dell.com deals that's Dell.com deals I'm on the road for these Daily Stoic talks I'm doing. I started in Seattle. My family and I drove all the way down. Now I'm in San Francisco. We're in Sacramento tomorrow. I've actually been booking houses on Airbnb all along the way. We stayed in this awesome one in Mendocino. Last night. We stayed in a lovely one on the ocean in Bremerton, Washington. It's been awesome. And that's usually how we stay as a family. When we're traveling, we book houses or apartments on Airbnb. But what a lot of people don't know is that when I first started as a writer, I used to list my house on Airbnb, my first house, this little house in East Austin. We would book it out when we were out of town, which is what Airbnb is so great at. And then when we moved out to the country, I would write at it during the week and book it out on the weekends. And that's how we helped cover the mortgage. That's how I was able to make the transition from a marketing person to a writer. Wherever you live, but especially if you live in a city that's hosting a bunch of events this summer, or you you're traveling, you should think about listing your house or apartment or condo on Airbnb. It might be worth more than you think. And you can find out how much@airbnb.com host welcome to the Daily Stoic podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world. Obviously, there are multiple definitions of what it means to be rich. Seneca talks about how, you know, poverty isn't just having too little. It's also the desire, the need, the quenchless thirst for more. There's very poor rich people and the stoics, when they talk about wealth, they have obviously a more expansive definition than just how much is in your bank account, how much land do you have, how powerful or important you are? Sahil Bloom wrote this book called the Five Types of Wealth. And what he says in the book is that we have different forms of wealth. And so in today's episode, Sahil and I talk about our definitions of wealth, about success, what we can learn from the Stoics about these very things, and much more. You can follow him on Instagram and on Twitter Al hillbloom. I was very excited to have Sahil Hill on the podcast. I've read his writing for a long time. If you want to check out the Daily Stoke Wealth Challenge, I will link to that in today's show notes. Or you can join Daily Stoke Life, where you get it and our other challenges for free. So I think when people think wealthy, their first thought is money. But it strikes me that that's almost the least important or certainly the least meaningful form of wealth. Because I. I would say I've met some very poor rich people.
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I think we all have. We don't have to look far to find examples of the Pyrrhic victory, if you will. You know, the idea of the victory that comes at such a steep cost. It might as well have been a defeat. The. The battle won. We all know or have heard stories of that billionaire or centimillionaire who has made hundreds of millions of dollars, but they have four ex wives and three kids that don't talk to them.
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Yeah.
B
And we live in a society where we pat that person on the back and we write books about that person oftentimes and we ignore the fact that they have suffered these defeats in these other areas of life. And the challenge that I have seen is that culturally, we tell every young person, we indoctrinate them into this idea that that is what a wealthy life looks like, that you go and make a lot of money. And we ignore the fact that there are these clear deficiencies in these other areas. And my call to action around all of this is to ask yourself if that is what winning the game looks like in the traditional definition. Is that actually a game that you care to win?
A
Yeah, because I think obviously money is a means to an end, and if you could get the end without money, that's probably a good way to do it. And if you get the money, but it doesn't actually allow you or facilitate the end that you have envisioned as what you want your life to be. Again, you went about it the wrong way.
B
Yeah. The way that I've always thought about this is it's sort of Like a Maslow's hierarchy of needs question where, yes, money buys happiness in the early days, it very directly allows you to take care of basic needs. Needs, food, shelter, take care of the people around you. Even the early days of like, affording basic pleasures.
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Sure.
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Vacations, those basic things, they clearly do buy happiness. And the science actually proves that out the early part, there is a very clear direct correlation. The challenge is what happens after that.
A
Yeah.
B
And for most people, we get patterned into this understanding of that linear relationship where an incremental unit of money equals an incremental unit of happiness. And then we're convinced that that is going to exist in. In perpetuity. Y and it doesn't. And you learn that at some point, either the hard way or you learn it by understanding it internally so that you avoid the hard way.
A
Yeah, yeah. It's like having a great life without any money is probably not possible. But just because you have a lot of money doesn't mean you're going to have a great life.
B
That's a good way of articulating it. Money isn't nothing. It simply can't be the only thing.
A
Well, it's definitely not everything. And if it's the only thing, I would venture to guess it's a shitty life. Do you know, like. Like one of the things I've been struck by on some of the really wealthy people. I mean, it's not just that they're poor in the sense that they're missing out on happiness or family or, you know, something, some kind of meaning, or they're just not a good person, that form of poverty. But even though they have a lot, they don't feel rich because what they want is more. Seneca talked about how, you know, poverty is. Is obviously having too little, but it's also just wanting more. So you can, by. By this definition, you can be an incredibly impoverished billionaire or millionaire. You can come from incredible wealth. But if it doesn't feel like enough to you, or what you need is more and more and more because you're trying to have more than someone else, or you're trying to have the most, you're always going to feel deficient.
B
That idea of enough, that word enough is so central to this entire concept, Right? It's that the famous story of Kurt Vonnegut and Joseph Heller going to the house of that billionaire in the Hamptons. And Vonnegut says, how does it feel that this guy just yesterday made more money than your most famous book, Catch 22, made in its entire lifetime? And Heller says, I've got something that he'll never have. Vonnegut says, what's that? The knowledge that I've got enough. And that is so important, especially in this day and age, because when they said that, it was a long time ago, that was pre social media. Now you have more awareness of other people's lives and highlight reels than ever before. And that makes the embrace of your present enough or your definition of enough that much harder to actually internalize.
A
Well, I also imagine so that, let's say that story is in the 50s or 60s, right? I imagine if you looked at what income inequality looked like then, or you looked at, like, let's say that's. That Guy's probably some CEO of some big company. You know, back then, a CEO probably made 20 times more than the average employee, and today the CEO might make 200 times more than the other employee. So it's not just like, there's something timeless about, like, hey, you gotta have enough. But there's also something that I think modern technology and globalism, all these things have unlocked, which is the potential to be, like, unimaginably wealthy. Like, what is enough or what is a lot even, right? Like, maybe it's impossible for humans to ever fully have enough from, like, a biological standpoint, having enough. But can you just get to a place where you comprehend that you have a lot? That's a huge victory, and that is the understanding that you are wealthy. Like, hey, I have a lot. I have. I have so much that other people are jealous of what I have. And then again, we can expand this definition to not just be my. Like, how many people wake up every day and are sad or depressed that they're. They're not married or they don't have children or they don't have a house? Like, we have things that people would be profoundly jealous of, and yet people wake up every day and think they don't have a lot.
B
It's funny, even in hearing you articulate that, so much of the way that we articulate these things is impressing other people. It's like, oh, I want other people to be jealous or envious of the thing that I have. And I often think about that in the context of, like, mental time travel in your own life. How many things that you have today are things that your younger self would have dreamed of or more than, like.
A
Like, I. I sometimes go, like, the goal is to write one book. So I did that and I did a bunch more. But I don't. There's. There's something about the Diminishing returns, but also just about the way that we sort of do this accounting in our head. It doesn't feel like you are way past the mark that you aimed for. And so it's all, you know, like, yeah, it's all more than you would have dreamed of originally. But you don't, you're not waking up and actually feeling every day, hey, I'm playing with house money. Because what the mind does is immediately go to, well, other people have more. Oh, it's possible to do more. And then you're.
B
And you have changed, you are more proficient, you are more skilled, you are better. And so you naturally say, like, the thing that your previous self wanted is, is now undershooting what my capability is because I have grown. I do think that, look, I've experienced this very recently in a pretty visceral way in my own life that like I was in my office a few weeks ago just before the launch of this book, and I was working on something very focused, locked in on something for the launch. And my son, who's two and a half years old, came barging into my office and started doing two and a half year old things. He was like jumping up on the desk, throwing things around, making a mess. And I started having this very negative train of thought of, why is he doing this? This is so annoying. Doesn't he know I'm trying to focus? Shouldn't he be out of here?
A
All these things gonna prevent me from doing what I'm doing.
B
Yeah, the negative, you know, the spiral. And in that moment, I caught myself because there was a little picture on my desk of the two of us. And I took myself back in my own mind to four years ago when my wife and I were in the middle of a two year struggle with infertility. I had prayed every single night for two years that we would one day have a healthy child. And there I was in that moment complaining about the exact thing that I had prayed for. And it was a reminder to me of that fact that sometimes in life, the things that you pray for become the things that you complain about if you let them. If you aren't able to catch yourself in those moments and say, I am literally living out the prayers of my younger self. Catch yourself and pull yourself back into that moment. You are actually living out what your younger self prayed for. But we can create that awareness and take action against it. We're not incapable of doing that. It may be that our natural human disposition is to continue to experience that hedonic treadmill that desire for growth. It just needs to be grounded in something more meaningful than money.
A
Yeah. And I'm not saying, like, the goal is to appreciate all the ways that you have things that make other people jealous. Like, that's the goal. But it can be so easy to. To take things for granted and to think that something is nothing. Right? Like that your health. Like, how many people who are in a hospital are jealous of the people out the window just walking around living their normal lives? Right. Or someone in prison is jealous of someone who has freedom. Someone who works for themselves is maybe jealous of someone who has the security of a job. Conversely, someone who has the security of a job is jealous of someone who has a freedom of working for themselves. And. And you just can diminish what you have as not being a lot to. To say nothing of not being enough. And you don't realize that there are people who are waking up every day praying for that thing or, like, grinding it out for a shot at one of those things. And you're like, oh, I feel poor because I don't have this or that. You know what I mean?
B
Yeah, I do. I totally resonates. And I think that it's why I go back to the importance of the things that you measure in. Like, Peter Drucker has this famous quote, what gets measured gets managed. The idea that the thing that you can measure ends up being the thing that you myopically focus on, narrowly hone in on. And money historically, has been the only thing that we measured. Money's measurability is so clear. It was a feature, not a bug. Right. It's what allowed capitalists, free markets to grow, all these things, commerce. But unfortunately, it is clearly not the sole measurement of building a good life.
A
Sam.
Guest: Sahil Bloom
Host: Ryan Holiday
Date: July 27, 2026
Ryan Holiday sits down with Sahil Bloom, investor and author of The Five Types of Wealth, to dissect how we define and measure wealth—both as individuals and as a society. Drawing on wisdom from Stoic philosophy and personal experience, the conversation challenges the narrow focus on financial success and explores broader, more meaningful dimensions of a rich life.
The conversation is reflective, candid, and philosophical—both speakers blend personal anecdotes with Stoic lessons and practical wisdom for modern life. The tone is thoughtful and challenges listeners to re-examine their assumptions on wealth and success, encouraging gratitude, mindful measurement, and a broader definition of a truly “rich” life.
For further exploration:
Sahil Bloom’s book The Five Types of Wealth, The Daily Stoic Wealth Challenge, and additional resources linked in the show notes.