The Daily Stoic

It would be nice if we always had smooth sailing. But we don’t.

Wealth can free you—or consume you. Self-made billionaire Robert Rosenkranz joins Ryan to discuss how Stoicism can transform our approach to money, ambition, and identity. Robert shares how Stoicism has shaped his decision-making, honed his intuition, and influenced his mindset on wealth and living a fulfilling life. Robert Rosenkranz became a self-made billionaire as a pioneer in private equity, multi-strategy hedge funds, and the insurance industry. He launched the acclaimed NPR program, Open to Debate, funded Impetus Grants to extend human healthspans, and is founding an innovative cultural institution in New York to showcase immersive work at the intersection of visual art, sound, music, and technology.

Marcus Aurelius was the public face of an empire. Seneca published plays and books. Cato and Cicero ran for office. Epictetus was a slave to a powerful Roman, at his whim and his mercy. In other words, they knew what it was like to be criticized.

Courage calls us and what do we do? We ignore it. We let it ring.

You could say something…you should say something. But…you don’t.

The call for courage keeps returning, over and over. What matters most isn’t what we chose before, but what we choose right now.Listen to the talk that Ryan was supposed to give at The Naval Academy: Apple Podcasts, Spotify, YouTube

If it’s right, if it must be done….do it now.

If wealth meant fulfillment instead of finances, how rich would you be? In today's episode, Sahil Bloom, entrepreneur and author of The 5 Types of Wealth, joins Ryan to unpack how they balance ambition and fulfillment. They discuss the concept of having “enough”, their definitions of being wealthy, what we can learn from the Stoics about living a rich life, and more. Sahil Bloom is the owner of SRB Holdings, the managing partner of SRB Ventures, and author of The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life. He holds a master’s in public policy and a bachelor’s in economics and sociology from Stanford University, where he was also a four-year member of the Stanford baseball team.You can follow Sahil on Instagram and X @SahilBloom Sign up for Sahil's newsletter here: https://www.sahilbloom.com/newsletter

As dark as life can get, there are lovely things out there to cheer you up. 

You will never be secure enough, powerful enough that you won’t be afraid—that’s the whole point of courage.

You might know Ed Helms as Andy Bernard from The Office or Stu Price from The Hangover movies—but did you know he’s also a serious history buff? He’s especially fascinated by history’s biggest screwups, better known as SNAFUs ("Situation Normal: All F**ked Up"). In today’s episode, Ed joins Ryan to unpack some of these epic blunders, explain how history became an escape for him, and share why learning about the past can be surprisingly therapeutic.Ed Helms is an actor, comedian, podcast host, and author. Ed has starred as Andy Bernard in The Office, Stuart Price in The Hangover trilogy, We’re the Millers, The Lorax, and much more. He hosts the podcast SNAFU and just released his book SNAFU: The Definitive Guide to History’s Greatest Screwups. You can follow Ed on Instagram and X @EdHelms

We are all fighting our own battles, we are all besieged by misfortune in our own ways.

By winning the morning, we reduce the power that the rest of the day—much of which lies beyond our control—holds over us.

We tell ourselves that this is all for the future, that someday, in some big moment of significance, we’ll use it. But will we?You can grab the Right Thing, Right Now ebook for just $2.99 right now! If you prefer reading hardcover books like us, we have signed copies available over at the Daily Stoic Store, too!

We often ignore flaws in our body until they demand attention, but flaws in the soul are even harder to see—the deeper the damage, the less aware we are of it.Today’s episode is an excerpt from The Tao Of Seneca produced by Tim Ferriss’ Audio. Get the free PDF at tim.blog/senecaListen to other letters from Seneca:Seneca on Despising DeathSeneca on Conquering the ConquerorSeneca on Philosophy and FriendshipSeneca on Practicing What You PreachSeneca on The Reasons For Withdrawing From The World Seneca on Master and SlaveSeneca on Worldliness and Retirement

Just after 2 a.m. on April 11, the U.S. Senate confirmed retired Air Force Lieutenant General Dan Caine as the 22nd Chairman of the Joint Chiefs of Staff. As it turns out, Ryan had the opportunity to interview Gen. Caine a few years ago as part of The Daily Stoic Leadership Challenge.In honor of his recent confirmation, today’s episode is Ryan and Gen. Caine's powerful conversation. Gen. Caine reflects on being one of the first pilots in the air on 9/11, the core traits every great leader must embody, and how to effectively inspire and guide a team toward a shared mission.General Dan Caine is the 22nd Chairman of the Joint Chiefs of Staff. He has flown more than 100 combat hours in F-16 aircraft. His total flight hours are 2,800. Throughout his career he was awarded the Defense Superior Service Medal, Distinguished Flying Cross, Bronze Star Medal with bronze oak leaf cluster and the Defense Meritorious Service Medal. 

It was a dark world…and Marcus Aurelius desperately needed some light.

The right book at the right time is a powerful thing. In fact, it can change the whole course of your life.

Check out the previous lectures from Ryan Holiday at the U.S. Naval Academy here:Courage: The Power Of Courage Discipline: The Life Changing Art Of Self-DisciplineJustice: Stoic Habits To Help You Live And Be Better

"The body should be treated more rigorously, so that it may not be disobedient to the mind." — Seneca In today’s episode, Ryan sits down with Bonnie Tsui - author, swimmer, surfer - to unpack the deep connection between our muscles and mental resilience. They dive into everything from the intelligence of muscle memory, what the ancient Stoics knew about strength that we’ve forgotten, how exercise can actually bulk up your brain, and much more. Bonnie Tsui is a journalist, New York Times contributor, swimmer, surfer, and the author of American Chinatown: A People’s History of Five Neighborhoods, Why We Swim, and now On Muscle.