Even the brightest CEOs have those “what were we thinking?” moments that still haunt them in the middle of the night. Whether it was a botched product launch, a marketing campaign gone off the rails, or a deal that aged like milk, million-dollar mistakes have a way of sticking around — especially when the world keeps reminding you.
Some of these blunders cost companies fortunes, some tarnished reputations for years, and a few are still taught in business classes as cautionary tales. So grab some popcorn and enjoy these high-stakes disasters that probably still make a few top executives break out in a cold sweat.
15. Juicero’s $400 Wi-Fi Juicer Disaster
Spending over $100 million to build a juicer that people realized they could just squeeze by hand might be the definition of corporate regret. Juicero became a punchline overnight and a painful lesson in building a product no one actually needed.
14. New Coke’s Public Meltdown
In a move that still baffles marketing experts, Coca-Cola decided to fix a formula that wasn’t broken. The backlash was so fierce that they had to scramble and bring back the original — basically admitting the world hated “New Coke.”
13. Blockbuster Laughing Off Netflix
Blockbuster had the chance to buy Netflix for a measly $50 million but decided to pass because they thought people would always prefer physical rentals. Fast forward a few years, and one company is a global streaming giant, and the other is a trivia question.
12. Yahoo Passing on Buying Google
Yahoo had multiple opportunities to acquire Google for what now seems like couch-cushion money. Instead, they hesitated, fumbled, and ultimately watched Google grow into a multi-trillion-dollar empire.
11. Target’s Catastrophic Canada Expansion
Target thought it could waltz into Canada and dominate, but instead, they opened stores that were half-stocked and way overpriced. In less than two years, they pulled out, losing over $2 billion and their international dreams along with it.
10. Quibi’s Blink-and-You-Missed-It Crash
Quibi raised nearly $2 billion to revolutionize short-form video content, but nobody really wanted what they were selling. After six months, it was game over, and the whole thing became a cautionary tale for overhyping untested ideas.
9. MySpace Losing to Facebook
MySpace had the social media game in the palm of its hand before Facebook casually walked in and stole the show. Bad management, cluttered design, and a failure to evolve turned them into a digital ghost town.
8. Kodak Ignoring Digital Photography
Kodak literally invented digital photography — and then sat on it because they didn’t want to hurt their film business. Meanwhile, the world went digital, and Kodak went bankrupt trying to play catch-up.
7. Microsoft’s $7 Billion Nokia Mistake
Microsoft thought buying Nokia would give them a fighting chance in the smartphone wars. Instead, it burned a giant hole in their pockets and left them waving a white flag to Apple and Android.
6. DeLorean’s Dream Crashing and Burning
![DeLOREAN DMC-12 [SPORTS CAR]](https://thequickreport.com/wp-content/uploads/2025/05/Untitled-design-2025-04-30T210521.312-1024x658.png)
The DeLorean car looked cool enough to star in movies, but the actual business was a financial disaster from the start. Between production issues and legal problems, the company flamed out faster than a time-traveling flux capacitor.
5. Google Glass Fizzling Out
Google Glass seemed like the future — until people decided they didn’t want to look like cyborgs in public. Millions were poured into a product that mostly ended up as a punchline and a museum piece.
4. Toys “R” Us Missing E-Commerce
Toys “R” Us made the tragic mistake of outsourcing its online sales to Amazon in the early days of e-commerce. By the time they realized their mistake, Amazon had eaten their lunch, and the toy giant was headed for bankruptcy.
3. Peloton’s Cringey Holiday Commercial
Peloton thought it was promoting fitness inspiration, but instead, it sparked backlash for being tone-deaf and out of touch. Even though sales stayed strong, that commercial became an awkward meme nobody at HQ wanted to be reminded of.
Read More: 30 Companies That Lost Money in Shockingly Stupid Ways
2. Exxon Buying XTO Energy at the Wrong Time
Exxon dropped $41 billion on XTO Energy, betting big on natural gas right before prices tanked. Years later, it’s still considered one of the worst-timed deals in corporate history.
Read More: Scandal in the Corner Office: 10 CEOs Who Totally Blew It
1. WeWork’s Spectacular Implosion
WeWork was once valued at $47 billion before reality — and some brutal IPO documents — came crashing down. The company’s freefall was so messy that Hollywood is still making shows about it, while investors are still trying to forget it.
Read More: 10 Rising Power Players Who Could Be the Next Billionaires
