Betrayal & Greed: How 4 CEOs and 5 Billion Failed Twitter

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Twitter has a new owner and his presence is sinking in. Regardless of whether or not you think Elon Musk can save Twitter, the reality is that Twitter as a private company under Elon can’t get any worse than the Twitter that has existed for the past 9 years. Twitter has struggled with declining users, engagement, turnover, innovation, infighting, losses, and vision. Twitter burned through 4 CEOs and 5 billion dollars in 10 years – regressing further away from being a viable business or attractive product.

Twitter is not just a case study of business mismanagement and poor strategy, but also a story of betrayal, ego, and greed. Since its founding, the company has been like Game of Thrones, plagued with politics and schemes. At the center of Twitter’s story, there is a founder, whose desire to be seen as a spiritual, futuristic genius was so important that he would do everything to achieve this recognition – even if it meant backstabbing friends and undermining his own company to do so.

In this episode, we’ll cover the death of Twitter, how the once-promising social media platform deteriorated to the point of an Elon Musk takeover, the schemes that brought each CEO to power, and an evaluation of their tenures, strategies, successes, and failures that have led Twitter to where it is today.

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🎧 Audio Editing & Mixing: Sonalf

0:00 Fly High, Crash Hard
7:49 There Are No Saints
18:29 The Noose Tightens
21:43 The Plot Thickens
35:25 The Knife Sharpens
41:38 The Straw that Broke the Camel’s Back
46:43 Best Served Cold
54:43 The Prodigal Son

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27 Comments

  1. 🔊Thank you for those who have raised feedback with this episode's audio levels / volume. To help, we have added official subtitles (not the incorrect YouTube auto-generated ones) to improve viewing experience and reduce volume mismatch. We will make sure this doesn't happen again in the future.

    📖The details about Twitter's founder disputes would not have been possible without the investigative reporting from journalist Nick Bilton and captured in his incredible book, Hatching Twitter. Investigative journalism into Silicon Valley is rare and deserves support. If you enjoy this episode and are interested in learning even more about Jack Dorsey and the power struggles at Twitter over the years – or if you liked David Fincher’s The Social Network or Walter Isaacson’s Steve Jobs biography, consider making Hatching Twitter your next read. This episode only provides key abstractions whereas the book serves as a comprehensive and entertaining read.

    0:00 Fly High, Crash Hard
    7:49 There Are No Saints
    18:29 The Noose Tightens
    21:43 The Plot Thickens
    35:25 The Knife Sharpens
    41:38 The Straw that Broke the Camel's Back
    46:43 Best Served Cold
    54:43 The Prodigal Son

  2. Wait..how do YOU know who was telling the truth?? The way you tell the story, seems no one else seemed to know what was up: not the board, not the media, no one. But YOU do somehow know what was REALLY happening behind the scenes. Thats sus dude.

  3. Hi, fascinating video. Please look into your sponsor — the Lord/lady thing is a scam as far as I can tell, the costume exists but the way entitled titles is doing it is not recognized. A few other YouTubers and bloggers have covered this. There's also other red flags — based in Hong Kong but addressed in NY or something, little transparency, some reports that owner may be under investigation for other issues, etc.

  4. Nope the former CEOs did great, they managed to sell the company for 3 times what it was worth… 44 billion dollars.
    Now twitter is sunk in debt that needs to pay at 1.5 billion a years …. Far more than it ever created as revenue… So yeah…

  5. Jack and Elon are both failing to turn Twitter into a relevant social media site. Jack didn’t grow it due to his focus on square, and Elon is equally moronic with his strategies.

  6. Exceptional video as usual. The only thing I'm not sure I agree is the ending. Personally I think Elon himself is as toxic maniac as Dorsey.

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