Running a company is tough, but sometimes the people at the top make decisions so baffling that you almost have to respect the audacity. From misguided launches to straight-up denial about the obvious, these CEO moves started as small mistakes and snowballed into full-on disasters.
Some of these leaders thought they were bold visionaries, while others ignored every flashing warning light. Either way, they ended up with some of the most cringeworthy cautionary tales in corporate history.
20. J.C. Penney’s Price Tag Problem
When J.C. Penney’s CEO decided to eliminate sales and coupons, he forgot that customers actually loved the feeling of getting a deal. The company’s revenue fell off a cliff, and shoppers never really came back.
19. Kodak Ignoring Digital Cameras
Kodak literally invented the digital camera but stuck with film because it thought digital would hurt its business. Spoiler alert: Pretending new technology doesn’t exist is not a winning strategy.
18. Blockbuster Laughing Off Netflix
Blockbuster had the chance to buy Netflix for cheap and said, “Nah, we’re good.” A few years later, Blockbuster stores were basically ghost towns while Netflix ruled the world.
17. WeWork’s Chaotic Crash
WeWork’s CEO thought the company was a tech startup when it was really just fancy coworking spaces. After burning through billions and trying to go public, the whole thing collapsed like a Jenga tower.
16. BlackBerry’s Keyboard Obsession
BlackBerry executives clung to physical keyboards like they were life rafts, even as touchscreens took over. By the time they tried to catch up, it was already game over.
15. Quibi’s “You’re Watching It Wrong” Approach
Quibi spent nearly $2 billion creating short-form video content that nobody actually wanted. Instead of adapting, leadership doubled down and blamed the audience.
14. Yahoo: Saying No to Google
Yahoo had multiple chances to buy Google for peanuts and failed every time. Eventually, Yahoo was sold for a fraction of its former worth.
13. Juicero’s Wi-Fi Connected Disaster
Juicero raised millions for a $400 juice machine that squeezed pre-packaged bags—something you could literally do with your hands. People weren’t about to pay that much for something so ridiculous.
12. Sears Missing the Online Boat
Sears had everything it needed to dominate online shopping, but somehow missed the internet entirely. By the time they woke up, Amazon had eaten their lunch, dinner, and dessert.
11. Uber’s Toxic Culture Crisis
Uber’s former CEO thought scaling fast meant ignoring a pile of workplace scandals. Instead of world domination, the company spent years doing damage control.
10. MySpace Failing to Evolve
MySpace was the king of social media until it tried to become everything to everyone. Users bailed for the cleaner, faster experience of Facebook, leaving MySpace a digital relic.
9. Theranos and the Big Lie
Elizabeth Holmes promised blood tests that could change the world, but the tech never actually worked. Once the truth came out, Theranos crashed and burned spectacularly.
8. Toys “R” Us Drowning in Debt
Toys “R” Us took on massive debt instead of adapting to new shopping trends. Saddled with unsustainable payments, the company filed for bankruptcy and closed hundreds of stores.
7. Twitter’s Leadership Revolving Door
Twitter kept swapping out CEOs and changing strategies like a game of corporate musical chairs. Unsurprisingly, it struggled to grow consistently for years.
6. Juul’s Youth Marketing Nightmare
Juul became wildly popular but didn’t foresee (or ignore) the massive backlash for its appeal to teens. Lawsuits, regulations, and public outrage sent the company into a tailspin.
5. Peloton’s Treadmill Tragedy
Peloton rushed to launch a treadmill without enough safety features and ended up recalling thousands of units after accidents and a tragic death. The fallout torched their reputation and stock price.
4. RadioShack’s Identity Crisis
RadioShack never figured out if it wanted to be a tech store, a cell phone store, or just a weird collection of cables and batteries. Customers left confused, and eventually, they left altogether.
3. MoviePass’s Insane Business Model
MoviePass thought offering unlimited movie tickets for $10 a month would somehow generate revenue. It did not, and the company melted down under the sheer weight of its unsustainable idea.
Read More: 10 Brands That Used To Be Great—But Lost Their Value
2. FTX’s Complete Meltdown
FTX’s CEO looked like the golden boy of crypto until billions of dollars mysteriously disappeared. It turned out to be one of the biggest financial disasters in recent memory.
Read More: 15 Websites We Used to Love (Until They Died)
1. Enron’s Historic Implosion
Enron’s executives built a house of cards based on fake profits and shady deals. When it all came crashing down, it didn’t just destroy a company—it wrecked lives, savings, and trust in corporations.
