Mark Cuban’s Broadcast.com trade became dot-com legend

Mark Cuban sold Broadcast.com to Yahoo for $5.7B on April Fool’s Day in 1999.
The company had no profits.
The idea was simple: stream out-of-town radio broadcasts over the internet.
At the peak of the dot-com boom, Yahoo was fighting AOL and Microsoft for control of the internet homepage and was willing to pay almost anything for future-looking assets.
Cuban owned a large stake and walked away with roughly $1.4B.
But the truly legendary part was what happened next.
He hedged his Yahoo shares before the crash, paying Wall Street banks to lock in value while the bubble was still alive.
When Yahoo collapsed from hundreds of dollars per share to single digits, Cuban had already protected the bag.
Broadcast.com was shut down three years later.
In 2017, Verizon bought all of Yahoo for less than Yahoo had paid for Broadcast.com alone.
It remains one of the clearest examples of bubble timing, exit discipline, and why paper wealth is not real until it is protected.