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10 of the Most Expensive Mistakes in History

By the Rabbit Hole Daily team·Sep 22, 2026·2 min read
10 of the Most Expensive Mistakes in History

Everybody makes mistakes. Most of us don’t make mistakes worth hundreds of millions — or even billions — of dollars. These people and companies did.

1The $100 million pizzas

On May 22, 2010, programmer Laszlo Hanyecz paid 10,000 Bitcoin for two Papa John’s pizzas — one of the first real-world Bitcoin purchases. At Bitcoin’s later prices, those coins have been worth hundreds of millions of dollars. May 22 is now celebrated as “Bitcoin Pizza Day.”

2The Beatles rejection

In 1962, Decca Records auditioned the Beatles and passed. The band signed with EMI instead and became the best-selling music act of all time.

3NASA’s metric mix-up

In 1999, NASA lost its Mars Climate Orbiter because one team used imperial units and another used metric. The $125 million spacecraft flew too close to Mars and was destroyed.

4Selling Apple for $800

Ronald Wayne co-founded Apple in 1976 with Steve Jobs and Steve Wozniak and owned 10% of the company. Less than two weeks later, he sold his stake for $800.

5Blockbuster says no to Netflix

In 2000, Netflix’s founders reportedly offered to sell the company to Blockbuster for $50 million. Blockbuster passed. You know how that ended.

6Excite passes on Google

In 1999, Google’s founders offered to sell their search engine to Excite for under $1 million. Excite said no.

7The 45-minute meltdown

In 2012, a software glitch at trading firm Knight Capital sent out millions of unintended stock orders. In about 45 minutes, the company lost around $440 million.

8The rocket that blew up over one number

In 1996, Europe’s brand-new Ariane 5 rocket exploded about 40 seconds after launch. The cause: a piece of reused software tried to cram a number that was too big into a space that was too small.

9Hubble’s blurry vision

After the Hubble Space Telescope launched in 1990, its first images were blurry. Its main mirror had been ground to the wrong shape — off by about 2 micrometers, a fraction of the width of a human hair. Astronauts had to fly up and install corrective optics in 1993.

10The Bitcoin in the landfill

In 2013, James Howells of Wales accidentally threw away a hard drive containing thousands of Bitcoin. He spent years trying to get permission to dig through the local landfill to find it.

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