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Ryan Holiday
Foreign welcome to the weekend edition of the Daily Stoic Podcast. On Sundays, we take a deeper dive into these ancient topics with excerpts from the Stoic texts, audiobooks that we like, hear or recommend here at Daily Stoic, and other long form wisdom that you can chew on on this relaxing weekend. We hope this helps shape your understanding of this philosophy and most importantly, that you're able to apply it to your actual life. Thank you for listening. Hey, it's Ryan. Welcome to a Sunday episode of the Daily Stoic Podcast. Can a Stoic be rich? Is Stoicism pro or anti capitalism? Pro or anti big business? What would the Stoics think about the modern economy? What would they think about income inequality? What would they think about entrepreneurship? I don't know exactly. I mean, the Stoics have always been in the mix in these things. Seneca was quite wealthy. Zeno was a merchant. He is introduced to philosophy when he loses everything. His quip was, I made a great fortune when I suffered a shipwreck. I've had a number of very wealthy, very successful people on the podcast, but very few of them have explicitly been Stoics or fans of the Stoics. We talked about Stoic themes, but not Stoicism explicitly. So I was really interested when I heard about this book coming out called the Stoic Capitalist by Robert Rosenkrans, who is a self made billionaire, one of the pioneers of private equity, hedge funds and insurance. He's also a patron of the arts and medicine, sort of a patron of like the ideas of civil discourse and free speech. He's launched an acclaimed NPR program called Open to Debate. He's a funder of what's called the Impetus Grants, which are designed to extend human health spans. And he is a big fan of the Stoics. He wrote this book about Stoicism and capitalism and I wanted to bring you an excerpt of that. My favorite chapter in the book, which has a very Stoic idea based on Seneca. The chapter is called you can make more money, you can't make more time. We had a great episode with Robert on the podcast. I will link to that in today's show notes. And then after you read the Stoic Capitalist, you might want to check out something we did over at Daily Stoic called the Wealthy Stoic, which is a guide or a course on the Stoic definitions of being rich and happy and free. My argument is that Seneca is actually not the richest of the Stoics, but that Epictetus is. That's because one needed the money and the other sort of freed himself of the need for the money. Anyway, these are all themes I think Robert touches on in the book, I think we touch on in the conversation and I think you will enjoy. Remember, you can get the wealthy Stoic and all the Daily Stoic courses for free when you join Daily Stoic Life. And do check out the Stoic Capitalist. It was the book club pick for this month for Daily Stoic Life. The audiobook's great. You'll listen to that now. Thanks to him and his publisher for bringing it out. I hope you enjoy it.
Robert Rosenkrans
You can make more money, you cannot make more time. Continue. Dear Lucilius, to set yourself free for your own sake, gather and save your time, which till lately has merely slipped through your hands. This admonition from the very first of Seneca's Letters to Lucilius, a foundational text of Stoic philosophy, advises that to live a better life we must be constantly vigilant of our time. Earlier, when Seneca was at the height of his influence as Emperor Nero's top advisor, he wrote a little book on the Shortness of Life in which he advises, life, if you know how to use it, is long. It's not that we have a short time to live, but that we waste so much of it. Life is long enough to accomplish even the greatest things if it is well invested. But when life melts away through carelessness and the pursuit of luxury, and when death finally presses down on us, we realize that life passed us by before we even know it was passing. Seneca and Marcus Aurelius both posit that having a consistent goal is key to using one's limited time. Well, the Stoics speak of a consistent goal as an organizing principle for a well lived life. But this does not mean living primarily for something in the future. Seneca cautions against expectation, which depends on tomorrow and wastes today. I would add that it is vitally important that the pursuit of that goal be as much a source of personal growth and satisfaction as the goal itself. The launch of Rosencrans & Co. And the decade or so following was the most purposeful period in my own life and in many ways the most rewarding. Here are precepts that helped me use time well, or at least efficiently. Prioritize. It is easy to prioritize in business. Just count the zeros. If the financial consequences are large, focus your attention fully. If they are small, don't clutter your calendar or your mind. Decide in your own situation what constitutes a meaningful building block of value and and simply say no to anything beneath that threshold. If a meeting doesn't have a clear and important purpose, try to avoid it. Being busy is the enemy of being thoughtful. As Marcus Aurelius says, if you seek tranquility, do less. Or more precisely, do only what is essential and do it with greater concentration.
Ryan Holiday
Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastow County, I drove my car about halfway down the dirt road that we live on, thought this isn't going to work. Stopped, parked it walked the rest of the way home, borrowed my wife's car, drove into Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields and on the unpaved roads like the one that I lived in. We got to go deep into the Hill Country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we I mean not just my wife, but both my kids, who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course, because you never know when you'll end up on a Toyota adventure detour. And of course, this is stoicism too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you, discover your uncharted territory. Learn more@toyota.com Trucks Adventure detours.
Robert Rosenkrans
An approach that has worked for me is to take an occasional yellow pad day. These are full days with no other appointments or distractions. I go off to someplace unfamiliar where I am unlikely to be interrupted a rare book library, for example, and turn off my phone. I make notes on a yellow pad. I start with people and consider who I would like to see more of or less. I think about relationships that might have outlived their usefulness or that might need repair. I consider opportunities for self improvement activities I would like to do more of or less. Bad habits I may have fallen into, areas I might want to learn more about or skills I might want to develop. I move on to review changes in the world to which I might need to adapt. Big opportunities I might be missing small projects that might be bogging me down, risks I may not be thinking about or preparing for. This sounds more formulaic than it is. Each yellow pad day is different and reflects my biggest concerns at the time. By the end of the day, I often understand better what is essential to me. A more thoughtful basis to prioritize in life Delegate Another precept is to delegate wherever possible. In general, if someone else can do it, they should. If they can do it as well or better than you would, great. If they can do it reasonably well, that's probably fine. And if they cannot do it adequately or need more of your time to supervise than you think appropriate, you need to find someone stronger for that role. But don't fall into the time trap of doing things that should be delegated. In my view, delegating is necessary but not sufficient. Be sure the people with important roles in your business or in your philanthropic initiatives have incentives that are well aligned with your goals and objectives. And once you have done that, don't micromanage. If you have given them responsibility, give them the authority to match in thinking about leisure and personal consumption, I try to be conscious of how my choices impact the way I spend time. I certainly live well and creating our homes has been satisfying, but for me the real luxury is the ability to control how I use my time. In my personal life as in my business life, I want to delegate as much as possible. I don't want to spend my time on scheduling or logistics. I don't like to shop or in the language of business, I want to hire a purchasing agent, not become one. I want more life enhancing experiences, not a bigger inventory of stuff. I want other people to maintain the household, supervise the staff and do the cooking. As in business, this means hiring the best talent one can find, delegating responsibility and authority, and not micromanaging. Ideally, I want to spend 100% of my time in purposeful activity and meaningful pursuits. As a modern reader of Seneca, Stephen Fidler puts the key phrase here is free yourself for yourself. 300 years before Seneca, the Greek Stoics developed the idea that in addition to being enslaved physically, it is also possible to be enslaved psychologically. Stoicism as a philosophy was designed to free its practitioners from the slavery of false judgments and opinions that lead to negative emotions like fear, anxiety, greed, anger and resentment. The Stoic concept of freedom is not license to do whatever you like, but self possession of learning how to value and experience the fullness of time.
Ryan Holiday
Thanks so much for listening. If you could rate this podcast and leave a review on itunes. That would mean so much to us and would really help the show. We appreciate it. I'll see you next episode.
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Ryan Holiday
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Podcast Summary: The Daily Stoic
Episode: You're Wasting The One Thing You Can’t Get Back
Host: Ryan Holiday
Guest (excerpt): Robert Rosenkrans
Date: June 15, 2025
This episode of The Daily Stoic centers around the Stoic conception of wealth, time, and what it really means to live a rich, fulfilled life. Host Ryan Holiday introduces the topic by framing Stoicism’s relationship to capitalism, success, and the value of time, drawing on historical examples (like Seneca, Marcus Aurelius, and Epictetus) and modern interpretations. The episode’s highlight is an excerpt from Robert Rosenkrans’ new book, “The Stoic Capitalist,” particularly the chapter “You Can Make More Money, You Can’t Make More Time,” where Rosenkrans shares practical Stoic-inspired principles for using time well. Throughout, the message is clear: while money can be earned and lost, time is the irreplaceable resource that must be fiercely guarded.
Timestamps: 00:37 – 03:28
Timestamps: 03:28 – 06:44
Timestamps: 05:15 – 06:44
Timestamps: 08:20 – 10:34
Timestamps: 10:34 – 12:12
For further exploration: Listeners are encouraged to check out Rosenkrans’ “The Stoic Capitalist” and the Daily Stoic’s “Wealthy Stoic” guide for deeper dives into these themes.