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The Question That Haunts the World’s Most Successful People | Andrew Ross Sorkin (PT. 2)

The Question That Haunts the World’s Most Successful People | Andrew Ross Sorkin (PT. 2)

The Daily Stoic
Dec 6, 2025 45 min
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About this episode

<p>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.</p><br><p>Andrew Ross Sorkin<strong> </strong>is a financial columnist for <em>The New York Times</em> and a co-anchor of CNBC's <em>Squawk Box.</em> He is also the founder and editor of <a href="https://www.nytimes.com/section/business/dealbook" rel="noopener noreferrer" target="_blank">DealBook</a>, a financial news service published by <em>The New York Times</em>. He wrote the bestselling book <a href="https://www.thepaintedporch.com/products/too-big-to-fail-the-inside-story-of-how-wall-street-and-washington-fought-to-save-the-financial-system-and-themselves?_pos=3&amp;_sid=4d3da5615&amp;_ss=r" rel="noopener noreferrer" target="_blank"><em>Too Big to Fail</em></a> and co-produced a movie adaptation of the book for HBO Films. He is also a co-creator of the Showtime series <em>Billions</em>. His new book is <a href="https://www.thepaintedporch.com/products/1929-the-inside-story-of-the-greatest-crash-in-wall-street-history-1?_pos=1&amp;_sid=4d3da5615&amp;_ss=r" rel="noopener noreferrer" target="_blank"><em>1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation</em></a>.&nbsp;</p><br><p>You can grab signed copies of <a href="https://www.thepaintedporch.com/products/1929-the-inside-story-of-the-greatest-crash-in-wall-street-history-1?_pos=1&amp;_sid=4d3da5615&amp;_ss=r" rel="noopener noreferrer" target="_blank"><em>1929</em></a> by Andrew Ross Sorkin at The Painted Porch: <a href="https://www.thepaintedporch.com/products/1929-the-inside-story-of-the-greatest-crash-in-wall-street-history-1?_pos=1&amp;_sid=4d3da5615&amp;_ss=r" rel="noopener noreferrer" target="_blank">https://www.thepaintedporch.com/</a></p><br><p>Follow Andrew Ross Sorkin on <a href="https://www.instagram.com/sorkinsays/?hl=en" rel="noopener noreferrer" target="_blank">Instagram @SorkinSays</a> and on <a href="https://x.com/andrewrsorkin?lang=en" rel="noopener noreferrer" target="_blank">X @AndrewRSorkin&nbsp;</a></p><br><p>👉 Support the podcast and go deeper into Stoicism by subscribing to<a href="https://dailystoic.supercast.com/" rel="noopener noreferrer" target="_blank"> The Daily Stoic Premium</a> - unlock ad-free listening, early access, and bonus content:<a href="https://dailystoic.supercast.com/" rel="noopener noreferrer" target="_blank"> https://dailystoic.supercast.com/</a></p><br><p>🎥 Watch the video episodes on<a href="https://www.youtube.com/@DailyStoic/videos" rel="noopener noreferrer" target="_blank"> The Daily Stoic YouTube channel</a>:<a href="https://www.youtube.com/@DailyStoic/videos" rel="noopener noreferrer" target="_blank"> https://www.youtube.com/@DailyStoic/videos</a></p><br><p>🎙️ Follow The Daily Stoic Podcast on<a href="https://www.instagram.com/dailystoicpodcast/?hl=en" rel="noopener noreferrer" target="_blank"> Instagram</a>:<a href="https://www.instagram.com/dailystoicpodcast" rel="noopener noreferrer" target="_blank"> https://www.instagram.com/dailystoicpodcast</a></p><br><p>✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at<a href="https://dailystoic.com/dailyemail" rel="noopener noreferrer" target="_blank"> https://dailystoic.com/dailyemail</a></p><br><p>🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store:<a href="https://store.dailystoic.com/" rel="noopener noreferrer" target="_blank"> https://store.dailystoic.com/</a></p><br><p>📱 Follow us:<a href="https://www.instagram.com/dailystoic/" rel="noopener noreferrer" target="_blank"> &nbsp;Instagram</a>,<a href="https://twitter.com/dailystoic" rel="noopener noreferrer" target="_blank"> Twitter</a>,<a href="https://www.youtube.com/@DailyStoic" rel="noopener noreferrer" target="_blank"> YouTube</a>,<a href="https://www.tiktok.com/@daily_stoic?lang=en" rel="noopener noreferrer" target="_blank"> TikTok</a>, and<a href="https://www.facebook.com/dailystoic" rel="noopener noreferrer" target="_blank"> Facebook</a></p><hr><p style='color:grey; font-size:0.75em;'> Hosted on Acast. See <a style='color:grey;' target='_blank' rel='noopener noreferrer' href='https://acast.com/privacy'>acast.com/privacy</a> for more information.</p>

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