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How Leaders Fail (And Why)

How Leaders Fail (And Why)

Von: Nathan Pali
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How Leaders Fail (And Why) is a history and leadership podcast about the moments when leadership breaks down—and the hidden reasons behind it.

Each episode explores real historical cases of leadership failure, bad decision-making, and misused power. Instead of focusing on outcomes alone, the show digs into why leaders failed: flawed incentives, overconfidence, fear, groupthink, bad information, moral shortcuts, and the pressure that distorts judgment at the top.

From military disasters and political collapse to corporate implosions and cultural breakdowns, this podcast examines how leaders fail, why smart people make terrible decisions, and how small leadership errors compound into irreversible consequences.

This is not a podcast about leadership theory or inspirational success stories. It’s a practical, story-driven look at leadership mistakes from history, organizational failure, decision-making under pressure, and the psychology of authority.

If you’re interested in leadership lessons, history podcasts, management failures, power dynamics, and understanding the real causes behind failure—not just the blame—this show is for you.

How Leaders Fail (And Why) Because failure is rarely accidental—and almost never sudden.

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  • The East India Company's Epic Fail

    The East India Company's Epic Fail
    Feb 25 2026

    In this episode, we explore the corporate leadership failures of the British East India Company leading up to the 1857 Sepoy Mutiny. We examine how cultural insensitivity, aggressive administration, and a major communication breakdown over rifle cartridges sparked one of the largest armed uprisings in colonial history.

    Chapters

    00:00 The Gathering Storm

    01:43 The Sepoys and Mounting Resentment

    03:38 The Greased Cartridge Controversy

    09:55 The Outbreak of Rebellion

    15:13 Brutal Retaliation and Sieges

    18:57 Aftermath and Lessons Learned
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    14 Min.
  • When the Referee Refuses to Enter the Game

    When the Referee Refuses to Enter the Game
    Jan 17 2026

    James Buchanan saw himself as a constitutional referee, not a player. In this episode, we unpack how that mindset failed when the country needed leadership—not commentary—during its greatest crisis.
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    10 Min.
  • James K. Polk: The Dark Horse President

    James K. Polk: The Dark Horse President
    Feb 24 2026

    In this episode, we explore the chaotic 1844 Democratic convention, where a political deadlock led to the unexpected nomination of James K. Polk, a "dark horse" candidate not even present at the gathering. We then learn how Polk, driven by a relentless work ethic and a clear vision of Manifest Destiny, dramatically expanded the United States during his single term in office.

    Chapters

    00:00 1844 Baltimore Convention

    00:18 Van Buren's Downfall

    04:46 The Dark Horse Emerges

    08:32 Polk's Presidential Promise

    10:00 Manifest Destiny and War

    16:29 Polk's Legacy and Aftermath
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    14 Min.
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