He had some kind of internet company in the late 1990’s and sold out for around $5 billion during the bubble. I forget the details but he got the better of the buyer. Like time warner buying AOL when everyone with a lick of sense knew that dial up services would be obsolete within 5 years.
Easy to say that people were stupid back then. It was a bubble. I guess Cuban made money off it. Unless there’s more to the story that we’re not aware of.
One view is he got lucky by selling broadcast.com for billions when ultimately it would be worthless. Another view is that it is extremely shrewd to sell at a high price.