Pulitzer Prize Historian: You Won't Notice Until It’s Too Late

ℹ️ EPISODE INFO

Released

May 11, 2026

Duration

1h 48m

Channel

The Diary of a CEO

Watch on YouTube

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📝 EPISODE DESCRIPTION

Anne Applebaum has spent decades studying how democracies collapse, how authoritarian systems rise, and why the warning signs are often ignored until it’s too late. She reveals why America is entering a dangerous new phase, and what happens next! Anne Applebaum is a staff writer at The Atlantic and has hosted its Autocracy in America podcast. She is also a senior fellow at the SNF Agora Institute at Johns Hopkins University and the School of Advanced International Studies. She is also the bestselling author of books such as, ‘Autocracy, Inc.: The Dictators Who Want to Run the World’. She explains:

• Why democracies rarely collapse overnight
• Why America may be closer to autocracy than people think
• How elected leaders can slowly take apart the system from within
• Why corruption is one of the clearest warning signs of authoritarianism
• Why Big Tech leaders are bending toward political power
• How America’s allies are already preparing for U.S. betrayal
• Why Russia, China, and Iran are challenging the democratic world order
• Why America may never fully go back to normal after Trump

00:00 Intro 02:10 Why History Keeps Repeating 03:33 Democracy’s Biggest Warning Sign 05:12 Why Democracy Feels So Broken 07:41 The Biggest Threats Right Now 08:52 Why Democracy Is Rapidly Shifting 10:18 Could America Become An Autocracy? 12:05 What A Trump Third Term Means 14:56 Why Autocracy Appeals To People 19:12 Trump’s Wealth Changes Everything 21:27 Why Global Stability Is Collapsing 26:26 Democracy Vs Dictatorship: What Lasts? 27:38 Who’s Happier: Democracies Or Autocracies? 29:04 Would Informed People Choose Democracy? 30:45 How Putin Stays In Power 32:40 5 Tactics Autocrats Use 34:19 Are Tech CEOs Enabling This? 38:11 Can America Ever Return To Normal? 39:27 Why Nations Are Turning Inward 43:57 What This Means For Americans 45:39 The Most Dangerous Part Of Dictatorship 48:49 Why Trump’s Ratings Are Falling 50:48 Ads 52:50 The 2nd Tactic Autocrats Use 57:39 The 3rd Tactic Autocrats Use 59:40 The 4th Tactic Autocrats Use 1:05:58 Should Social Media Have Legal Power? 1:12:58 Can Citizens Really Leave China? 1:14:15 The 5th Tactic Autocrats Use 1:14:48 Why ICE Is Breaking Down 1:17:00 Ads 1:17:32 Is The American Empire Declining? 1:21:32 Is Politics Just Human Nature? 1:24:20 Does Democracy Create Extreme Capitalism? 1:26:27 How Democracies Defend Themselves 1:28:01 Is Mainstream Media Politically Biased? 1:31:42 Why Journalism Matters More Than Ever 1:33:11 How Algorithms Control Your Reality 1:34:19 Anne’s Personal Political Journey 1:40:48 What Regime Change Really Feels Like 1:44:18 Anne’s Toughest Setback Follow Anne: Youtube - https://link.thediaryofaceo.com/4pTtMb1 Instagram - https://link.thediaryofaceo.com/1GOn8p5 X - https://link.thediaryofaceo.com/8M5yUMK Website - https://link.thediaryofaceo.com/GGmhcYf You can purchase Anne’s book, ‘Autocracy, Inc.: The Dictators Who Want to Run the World’, here: https://link.thediaryofaceo.com/D07471h Sponsors: Stan - Visit https://coach.stan.store/?ref=stevenbartlett&utm_source=youtube&utm_medium=podcast&utm_campaign=episode5 Wispr - Get 14 days of Wispr Flow for free at https://wisprflow.ai/steven

🎤 SPEAKERS

• Steven Bartlett

  host

  Host of The Diary Of A CEO and entrepreneur who interviews guests on business, society, and culture.

• Anne Applebaum

  guest

  Pulitzer Prize–winning historian and journalist known for books on the Soviet Union, the Gulag, and threats to democracy.

🧾 EPISODE SUMMARY

In this episode of The Diary of a CEO, featuring Steven Bartlett and Anne Applebaum, Pulitzer Prize Historian: You Won't Notice Until It’s Too Late explores anne Applebaum warns democracy erodes quietly through corruption and control Applebaum argues modern democracies usually don’t end with coups but with elected leaders slowly dismantling neutral institutions needed for fair elections, like courts, media, and the professional civil service.

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