Top 15+ Million-Dollar Mistakes That Still Make CEOs Cringe

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

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.