Worst financial decisions of all-time

[Discordant Resonance]

The story of the Decca executive turning down the Beatles because he considered guitar bands to be out of fashion is well-known at this stage, but consider the case of Ron Wayne, who decided to co-found a small smart-up in the mid-Seventies, got cold feet about his 10% stake eleven days later, and withdrew all interests for a few thousand dollars - just as well that Apple never amounted to anything ...

[Stumpy Pepys]

The story of the Decca executive turning down the Beatles because he considered guitar bands to be out of fashion is well-known at this stage

It's also something of a myth.

[Ginger Yellow]

I mean, for a single decision it's going to be hard to top buying Twitter as an unforced error. Though AOL/Time Warner was bigger.

[Stumpy Pepys]

Not on the magnitude of Twitter, but Lionel Bart selling all the rights to Oliver! to Max Bygraves--for £350--was really not the wisest decision.

[anton pulisov]

Twitter shut down the short video platform Vine to save money.

Now TikTok has taken over the world.

[Sean of the Shed]

The Truss/Kwarteng budget proved to be costly and still is.

[Sits]

AOL/Time Warner was bigger.

Damn right. Nobody seems to mention that catastrophe.

[Muukalainen]

Nokia's decision to divest itself of its core ASIC business, thereby robbing itself of its ability to control the full hardware design, certainly didn't go as planned.

EDIT: for clarity, the Nokia here is the mobile phones division.

[Guy Profumo]

The story of the Decca executive turning down the Beatles because he considered guitar bands to be out of fashion is well-known at this stage, but consider the case of Ron Wayne, who decided to co-found a small smart-up in the mid-Seventies, got cold feet about his 10% stake eleven days later, and withdrew all interests for a few thousand dollars - just as well that Apple never amounted to anything ...

Because he had a home and a mortgage - which would have been at risk had it gone pear

The Steves had no such exposure to risk

[Foot of Astaire's]

Wasn't there an actor who took a flat fee rather than percentage box office profits for something incredibly successful like Gone with the wind or similar? A quick search suggests Alec Guinness chose wisely for taking the percentage route after Star Wars.

[Rogin the Armchair fan]

The Beatles demo tapes must have sounded shit, to be fair. At that point they were mostly rubbish covers of Chuck Berry and Buddy Holly songs <grabs coat and runs before G-Man comes in>

[Tactical Genius]

Bah, this is nothing compared to Xerox who invented modern computing but thought all this geeky shit wouldn't catch on.

Many of their staff left Joined Apple, Microsoft and IBM and the rest is history.

[Discordant Resonance]

Well, they came up with the first GUI, but they lacked the real innovative expertise to capitalise on their discovery - apparently they did launch a computer before the Mac, but it was so expensive and clunky in design that virtually none were sold.

[Patrick Thistle]

Tom Brady putting all his wealth into crypto was a bad move.

[Nocturnal Submission]

The misconceived Darien Scheme had far-reaching ramifications: https://en.wikipedia.org/wiki/Darien_scheme

[WOM]

In the Rourke / Joyce lawsuit with The Smiths, Andy Rourke took the quick settlement offer of 83,000 GBP and 10% of royalties. Mike Joyce took his chances in court and left with 1,000,000 GBP and 25% of royalties.

[ursus arctos]

Would have been had Brady done that.

Even after the FTX debacle, his net worth is estimated as more than USD 300 million and he is about to start a USD 375 million broadcasting contract with Fox.

[caja-dglh]

Also - if his whole wealth were simply crypto and not FTX (which as noted it wasn’t) he would be pretty fine right now

[ursus arctos]

Also true

[Stumpy Pepys]

Well, they came up with the first GUI, but they lacked the real innovative expertise to capitalise on their discovery - apparently they did launch a computer before the Mac, but it was so expensive and clunky in design that virtually none were sold.

Apple launched a GUI-based computer before the Mac (the Lisa), which was also expensive and didn't sell well.

[Snake Plissken]

Wasn't there an actor who took a flat fee rather than percentage box office profits for something incredibly successful like Gone with the wind or similar? A quick search suggests Alec Guinness chose wisely for taking the percentage route after Star Wars.

Similar to this (and the opposite of the thread) is Bob Hoskins, who signed up to play Al Capone in The Untouchables if De Palma's original choice of Robert De Niro fell through. When De Niro signed and Hoskins received a cheque for $250,000 as compensation he rang De Palma and asked "are there any more movies that you don't want me to be in?"

[ursus arctos]

Napoleon's embrace of the Louisiana Purchase and the Russian sale of Alaska both deserve a mention, though it is true that either colonial power would have struggled mightily to defend the territory at issue.

The purported sale of Manhattan was an outright fraud.

[Snake Plissken]

ITV bought Friends Reunited and News International bought MySpace and then spectacularly failed to do anything about Facebook. Similar with Yahoo / Geocities, which had the self-service website thing a decade before Wix/SquareSpace/WordPress.

Oh, and Microsoft, with Pocket PC had a huge advantage over Apple in mobile devices but didn't see iPhone coming. (Neither did Google, but they had the chance to reengineer Android for a non-stylus interface in time.)

[blameless]

I still miss Geocities.

In a UK context, Gerald Ratner deciding to give a cocky speech in 1991 remains an all-time howler.

[Tactical Genius]

Well, they came up with the first GUI, but they lacked the real innovative expertise to capitalise on their discovery - apparently they did launch a computer before the Mac, but it was so expensive and clunky in design that virtually none were sold.

It was much more than the GUI, it was also the mouse, what would become Windows, Ethernet as well as many programming languages.

Part of the problem is the Xerox were making way too much money selling photocopiers and the didn't see the value in diversifying. Also the location where they stuck the Geeks in Paolo Alto was the other side of the country from the corporate headquarters.

The first PC they put out was well ahead of the competition and as you said was clunky but was released a decade before the Apple Mac which was basically a rip-off made for a fraction of the price.