15 Times Business Moguls And Megacorps Made God-Awful Financial Decisions

Microsoft: 8 Billion Reasons to Cry.
15 Times Business Moguls And Megacorps Made God-Awful Financial Decisions

Ahhh, the age-old story of hubris and financial folly. We’ve all heard it before, and it never fails to entertain. From the world’s wealthiest billionaires to the biggest and most powerful companies, it seems that no one is immune to the pitfalls of bad investments and costly mistakes. 

This list is no exception. It’s a collection of some of the most spectacularly expensive blunders in recent history, from Elon Musk’s $9 billion Twitter purchase to Warren Buffett’s “most gruesome mistake” to Yahoo’s $4 billion Geocities blunder. In many cases, the losses were so great that it shook the foundations of the companies involved.

So if you’re looking for a cautionary tale, or simply want to read about some of the most spectacularly expensive mistakes ever made by people rich enough to not care, then look no further. This list is sure to leave you shaking your head in disbelief at the sheer magnitude of these financial blunders.

Billion-dollar blunder: Yahoo’s Tumblr investment gone wrong.

CRACKED Search Tumblr-Home t of Fandom Memes Walpapers tumblr. OPEN 4.0 No75 17+ ***** Heiden Perfort What's New Version History Vection 15 Thanks kcal choosing Tumblr a place Dr connect - others over shared interests Preview YAHOO! In 2013, Yahoo acquired Tumblr for $1.1 billion, but the platform struggled to become profitable and was eventually sold to Automattic for $3 million in 2019.

CNBC / Scripps Voice 

Myspace: From $580 Million to $35 Million.

CRACKED NECK SOUTH its AX #News Corporation today NEWS CORP. News Corp. sold Myspace for $35 million, a huge loss compared to the $580 million they paid for it in 2005.

NPR / Fortune 

Excite: The Company That Said ‘No’ to Google.

CRACKED Google eXcite EXCITE In 1999, Google offered to sell to Excite for under $1 million, but Excite rejected the offer.

Tech Crunch 

Amazon-funded failure: Pets.com’s demise.

CRACKED JEFF BEZOS Pets.com was an ambitious online pet store that was funded by Amazon and had a sock puppet mascot, but it failed miserably due to its high advertising costs and inability to generate revenue.

Vice / IMDB 

Warren Buffett’s “most gruesome mistake” – a $8.7 billion blunder.

CRACKED WARREN BUFFETT Warren Buffett's most gruesome mistake was buying Dexter Shoe in 1993, which eventually collapsed due to cheap foreign imports, costing him 25,203 Class A shares in Berkshire Hathaway, worth about $8.7 billion today.

Business Insider 

DaimlerChrysler cashes out: $7.4 billion and goodbye Chrysler.

CRACKED DAIMLER DaimlerChrysler agreed to sell an 80% stake in its struggling U.S. brand Chrysler to Cerberus Capital Management for $7.4 billion, with Daimler expecting to pay out about $650 million to close the deal and take a $4-5.4 billion profit hit. The sale allowed Daimler to end its exposure to billions in ongoing losses and health care costs.

CNN / Auto News 

CEO resigns after financial regulator punishes $105 billion “ghost stock” mistake.

CRACKED SAMSUNG Samsung Securities Co CEO Koo Sung-hoon resigned after the company was punished by South Korea's financial regulator for an employee's error that sparked a $105 billion ghost stock blunder. The company was handed a six month partial suspension of its operations and its chief was suspended for three months.

Reuters / The Investor 

Citibank’s blunder: $900 million gone in an instant.

CRACKED CITIBANK Citibank made a mistake and accidentally sent $900 million to the wrong people, and the lenders refused to return the money. The lenders were taking advantage of the situation due to a longer running saga between them and Revlon, the company that borrowed the money.


Twitter Purchase: Elon Musk’s $9 Billion Mistake.

CRACKED ELON MUSK Elon Musk's net worth has dropped $9 billion since buying Twitter, and he is now facing a number of financial challenges in owning the company.

Time / NY Times 

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