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The Worst Business Deals In History

Trust Me Bro | November 9, 2026



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Are you curious about the worst business deals and business decisions ever? Well, you came to the right video! In this video, I dive deep into four business deals that cost companies and individuals BILLIONS in lost revenue. If you love history, business, and finance, this video is for you.

This video is for educational, artistic, and documentary purposes.

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Bookmarks:

0:02 – Blockbuster Bust
10:02 – Yahoo!s Whoopsie
14:57 – Microsoft Mega-loss
22:37 – The Apple Accident

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*Copyright Disclaimer Under Section 107 of the Copyright Act 1976, allowance is made for “fair use” for purposes such as criticism, comment, news reporting, teaching, scholarship, and research. Fair use is a use permitted by copyright statute that might otherwise be infringing. Non-profit, educational or personal use tips the balance in favor of fair use. No copyright infringement intended. ALL RIGHTS BELONG TO THEIR RESPECTIVE OWNERS.

For entertainment purposes only. Based on actual events.

Source: Trust Me bro

Video inspired by & other references:
https://youtu.be/M7SqQnKuZOQ?si=Ai6jZxR6ExseDoG6
https://youtu.be/dPyr5RB2Ilw?si=2ZSiObg4P4Y20uEJ
https://youtu.be/dTZkL3bmDN0?si=F0j5Mp3bM_2NGfGB
https://youtu.be/ndEwcp_HG34?si=a4-AWxdH_uz6VwVZ
https://youtu.be/6ghRStVJA28?si=4i66uV9IRZ06LIGD
https://youtu.be/89YZXIGOAB0?si=szZhDsZtp6Cq3VEv

Written by Trust Me Bro

Comments

This post currently has 41 comments.

  1. @cheyjackson909

    November 9, 2026 at 12:36 am

    There is a blockbuster building 15 min from my house, idk if they are open , but it's cool to look at it every time I pass by, still has the old sign on top , like a time capsule.
    I might try to walk in one day to see if they are locked. 9:12

  2. @MisterTim-b9w

    November 9, 2026 at 12:36 am

    Not to be an ass but how old are you? When I was 17 Blockbuster was going out the door and suddenly when I was 19 it was gone or not hiring. Given how young you sound I don't believe you experienced any of that and are going off 90s hype. To be clear the 90s weren't that cool we had less things and the Internet wasn't there. Calling some one on they payphone without a cell phone was regular for me till 2009 when I got a cell phone and it wasn't smart.

  3. @conn13b01

    November 9, 2026 at 12:36 am

    Is it just me or are TMB's videos quieter than others? I'll be at work listening and I can hear other videos fine over workplace noise but I struggle to hear this dudes. Sucks cause I love his shit

  4. @jonathanpate3799

    November 9, 2026 at 12:36 am

    Lol, it's crazy to think if Blockbuster at their peak would have bought or partnered with Netflix, Netbusters would be like the king of streaming and renting movies. Also, if they were making 20M a day, basically 50M investment would have been a drop in the bucket. Just dumb. The Yahoo and FB hold out was smart too. Knowing what you have and it's worth very important in business. The Skype deal I wasn't really interested in just because that's not something I used. Guess I'm more of a traditionalist, lol. Now, the Apple deal is just bonkers, lol.

  5. @infin1ty850

    November 9, 2026 at 12:36 am

    16:05 that wasn't really the best comparison. Skype became the direct predecessor to Teams after Microsoft bought them. Skype never really disappeared, Microsoft basically just evolved it and renamed it Teams.

  6. @joseville

    November 9, 2026 at 12:36 am

    Hmm, so Netflix was only doing the DVD rental via mail business at the time? If so, there's no guaranteed that Netflix under Blockbuster would have evolved into a streaming service tech company which is where all its value is and has been for a long time.

  7. @conqc20

    November 9, 2026 at 12:36 am

    I did that mail dvd service, but im sure it was Amazon? I think it was called "Lovefilm" though that could have been a separate company that Amazon bought up. It was a pretty good service.

  8. @Alois_from_Vienna_in_Austria

    November 9, 2026 at 12:36 am

    When Blockbuster declined too buy Netflix it was a company that send DVDs by mail, lost 50 millions $ last year and never made a $ profit. It was not a streaming service yet at all and it is not very probable that they would ever have changed into streaming if bought by Blockbuster. They did not pitch the idea of streaming too Blockbuster but sending DVDs by mail, which is a venture as dead today as Blockbuster.

  9. @cidiracing7481

    November 9, 2026 at 12:36 am

    19:00 Skype went exactly how Microsoft wanted. Buy up the competition, extract what they can for their own stuff and throw the remaining parts into the trash. It's been like that since the 90s. They could have reverse engineered Skype for their own app, but that doesn't remove Skype from the market and free up it's market share.

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