The Question That Haunts the World’s Most Successful People | Andrew Ross Sorkin (PT. 2)
Even the giants of history couldn’t outrun insecurity, comparison, or the feeling of not having enough. In today’s episode, Ryan continues his conversation with Andrew Ross Sorkin to talk about why success rarely feels satisfying in the way you expect, why the goalposts always seem to move, and how Andrew has seen this pattern play out in some of the wealthiest and most accomplished people in the world.Andrew Ross Sorkin is a financial columnist for The New York Times and a co-anchor of CNBC's Squawk Box. He is also the founder and editor of DealBook, a financial news service published by The New York Times. He wrote the bestselling book Too Big to Fail and co-produced a movie adaptation of the book for HBO Films. He is also a co-creator of the Showtime series Billions. His new book is 1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation. You can grab signed copies of 1929 by Andrew Ross Sorkin at The Painted Porch: https://www.thepaintedporch.com/Follow Andrew Ross Sorkin on Instagram @SorkinSays and on X @AndrewRSorkin 👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
6 Dec 202544min
No One is Truly “Self-Made” | The Philosophy Behind High Achievers
The myth of the self-made man is just that, a myth. There has never been such a thing.🎥 Check out the Arnold Schwarzenegger episode: https://www.youtube.com/watch?v=PBQlSMOVTAg📚 Pick up a copy of Arnold Schwarzenegger's book Be Useful: Seven Tools For Life at The Painted Porch: https://www.thepaintedporch.com/👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
5 Dec 202515min
This Will Make You Stupid | Ask Daily Stoic
It doesn’t matter how smart you are. In the moment, if you can’t control your emotions, you will be stupid.🪙 Carry The Daily Stoic Pause & Reflect Medallion as a reminder to pause. A pause creates space. A pause creates clarity. A pause can change everything. | Grab The Daily Stoic Pause & Reflect Medallion at dailystoic.com/pause👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
4 Dec 202511min
It’s Not That Complicated
Power is corruptive and corrosive no matter your age. To the young and inexperienced, it is even worse.📕 Book Mentioned: Wisdom Takes Work by Ryan Holiday 👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
3 Dec 20252min
Why Andrew Ross Sorkin Spent 8 Years Chasing One Story
How do you stay locked in on one project for eight years? Andrew Ross Sorkin shares what he learned while writing his bestselling book 1929: Inside the Greatest Crash in Wall Street History and How It Shattered a Nation in today’s conversation with Ryan. They talk about what it really takes to write a massive, deeply researched book while juggling a demanding career and family life. Andrew opens up about the fear, insecurity, and obsession that fueled his eight year journey into the world of 1929. Ryan and Andrew get into why writing still feels hard for him, the surprising reality of how much of history comes down to human behavior, and the strange process of trying to understand people who lived a century ago.Andrew Ross Sorkin is a financial columnist for The New York Times and a co-anchor of CNBC's Squawk Box. He is also the founder and editor of DealBook, a financial news service published by The New York Times. He wrote the bestselling book Too Big to Fail and co-produced a movie adaptation of the book for HBO Films. He is also a co-creator of the Showtime series Billions. His new book is 1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation. You can grab signed copies of 1929 by Andrew Ross Sorkin at The Painted Porch: https://www.thepaintedporch.com/Follow Andrew Ross Sorkin on Instagram @SorkinSays and on X @AndrewRSorkin 🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
3 Dec 202538min
We Can Give This to Each Other | Be Stingy With Time
We have to illustrate those virtues of courage and justice toward and for and through others. To help people from going hungry. To alleviate someone’s worry and fear. To put food on their table.Feeding America | We donated the first $30,000 and would love your help in getting to our goal of $300,000—which would provide over 3 million meals for families across the country! Just head over to dailystoic.com/feeding—every dollar provides 10 meals, even a small donation makes a big difference.📚 Books mentioned: On the Shortness of Life: Life Is Long If You Know How to Use It by SenecaThe Daily Stoic Journal: 366 Days of Writing and Reflection on The Art of Living by Ryan Holiday👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
2 Dec 202512min
This is What’s Really Important | Pretend Today Is The End
Let us be good Stoics today and prove that we don’t just talk about this philosophy—we live it.Feeding America | We donated the first $30,000 and would love your help in getting to our goal of $300,000—which would provide over 3 million meals for families across the country! Just head over to dailystoic.com/feeding—every dollar provides 10 meals, even a small donation makes a big difference.Resources Mentioned:- Action Against Hunger: https://www.actionagainsthunger.org/📘 Grab the hardcover edition of The Daily Stoic here: https://store.dailystoic.com/👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
1 Dec 202510min
BONUS | The #1 Way To IMMEDIATELY Feel Better
There’s so much happening in the world, and so much of it feels terrible. There is dysfunction. There is conflict. There is outright lawlessness. There is corruption. There is cruelty. But there’s a really easy way to feel better. Feeding America | We donated the first $30,000 and would love your help in getting to our goal of $300,000—which would provide over 3 million meals for families across the country! Just head over to dailystoic.com/feeding—every dollar provides 10 meals, even a small donation makes a big difference.🎟️ Come see Ryan Holiday LIVE: https://www.dailystoiclive.com/Seattle, WA - December 3, 2025 San Diego, CA - February 5, 2026 Phoenix, AZ - February 27, 2026 👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
30 Nov 202511min
