Sometimes, going big means going broke faster. These companies went all-in on bold visions, expensive rollouts, or wild pivots—only to end up as cautionary tales in the business history books.
Whether they underestimated the competition or caught a case of corporate overconfidence, these once-promising ventures learned the hard way. Here are 20 businesses that bet big and lost everything.
20. MoviePass
Unlimited movies for ten bucks a month sounded too good to be true—and it was. MoviePass tried to change the moviegoing game but torched a pile of investor cash instead.
19. Theranos
Elizabeth Holmes promised to revolutionize blood testing with just a drop. Instead, Theranos delivered one of the most infamous collapses in Silicon Valley history.
18. Blockbuster
They had the chance to buy Netflix and laughed it off. It turns out that streaming wasn’t a fad—it was their funeral.
17. Quibi
With nearly $2 billion in backing, Quibi thought people wanted “quick bites” of premium content on their phones. Turns out, people just wanted TikTok.
16. Borders
Instead of embracing e-books and digital retail, Borders doubled on physical locations. That slow pivot turned into a permanent shutdown.
15. Juicero
A Wi-Fi-enabled juicer that only worked with pre-packaged bags? Juicero overengineered itself into oblivion.
14. WeWork (the first time)
WeWork was supposed to redefine the future of workspaces. Instead, it redefined what happens when hype outpaces business fundamentals.
13. Kodak
Kodak invented the digital camera and buried it to protect its film business. That refusal to adapt cost them everything.
12. Pets.com
A sock puppet, a Super Bowl ad, and zero profits. Pets.com burned through investor money faster than it could deliver dog food.
11. Pan Am
Once the gold standard of air travel, Pan Am couldn’t keep up with deregulation and mounting losses, and its global empire crashed.
10. Sears
They had the infrastructure to become Amazon before Amazon existed. Instead, Sears became a masterclass in missed opportunities.
9. Beepi
Beepi tried to disrupt used car sales with a sleek online platform. Investors poured in millions, only for the company to sputter out before hitting the highway.
8. RadioShack
Even as tech boomed, RadioShack clung to outdated inventory and mall locations. It became the go-to store for stuff no one needed anymore.
7. Jawbone
Once a pioneer in wearable tech, Jawbone ran into hardware problems, legal battles, and fierce competition. They gambled on innovation and lost the race.
6. Vine
Vine had the internet in its hands but failed to evolve with creators’ needs. Then TikTok came along and showed everyone how it’s done.
5. Enron
Enron went all-in on complex accounting tricks and energy trading schemes. The implosion wasn’t just massive—it was criminal.
4. Toys “R” Us
Nostalgia couldn’t save a company that failed to modernize. They loaded up on debt and got steamrolled by online competitors.
3. BlackBerry
They dominated the mobile market until they didn’t. BlackBerry bet the world would never give up physical keyboards—and lost.
Read More: The 20 Dumbest Ways Companies Have Gone Broke
2. FTX
The crypto exchange grew fast, got flashy, and collapsed spectacularly. FTX proved that even billion-dollar bets can vanish overnight.
Read More: 20 CEO Blunders That Turned Into Full-Blown Nightmares
1. Lehman Brothers
Lehman Brothers helped fuel the 2008 financial crisis by taking reckless risks with mortgage-backed securities. Their bankruptcy was the biggest in U.S. history—and a painful lesson in corporate overreach.
Read More: 15 Times Greed Took Down an Entire Company
