Broadcast.com

The world's largest internet radio sold to Yahoo for $5.7B in 1999 at the peak of the dot-com bubble — Yahoo discontinued the service in 2002, but Mark Cuban had already sold all his Yahoo stock before the crash

Fatal mistake: Broadcast.com was the world's largest internet radio and streaming site. Mark Cuban and Todd Wagner sold to Yahoo for $5.7B in stock in April 1999 — Yahoo's second-largest acquisition ever. The Yahoo stock crashed with dot-com bust. Broadband was not yet widespread — streaming was ahead of infrastructure. Yahoo discontinued Broadcast.com services in 2002. Mark Cuban and Todd Wagner received $5.7B in Yahoo stock (later worth much less).