Mark Cuban sold Broadcast.com to Yahoo on April 1, 1999, in a $5.7 billion stock deal that turned a late-1990s internet business into one of the era’s defining windfalls. Yahoo agreed to pay $130 per share, a 50% premium to where Broadcast.com had traded just weeks earlier.
The timing mattered because the company was still a fast-rising dot-com story, not a mature business. Broadcast.com was generating $22 million in annual revenue and losing $16 million when Yahoo bought it, but its valuation had become untethered from those numbers.
Cuban’s path to that sale started long before the dot-com boom. In 1990, he sold his software integration company, MicroSolutions, to CompuServe and walked away with $2 million. Four years later, he and Todd Wagner realized there was no good way to listen to out-of-market Indiana University basketball games from Dallas, Texas, and they built AudioNet, which they officially launched in 1995.
By 1998, the company had expanded far beyond that original idea, broadcasting corporate events, radio stations and major sports. It changed its name to Broadcast.com that year and went public in July 1998, with shares initially priced at $18. By the end of the first trading day, they were changing hands at $62.75, giving the company a $1 billion market cap and leaving Cuban with a 25% stake worth about $250 million on paper.
The numbers kept climbing. By March 1999, Broadcast.com’s market cap had reached around $4 billion, and Cuban’s paper net worth had hit $1 billion. Just weeks later, Yahoo stepped in with the all-stock purchase that locked in the peak of the dot-com moment for both the company and its founder.
The deal also sits in a larger arc of Cuban’s early business life. The money from MicroSolutions gave him the capital base before Broadcast.com, and the Yahoo sale turned a Dallas sports workaround into one of the most famous paper fortunes of the internet era. The date also lands in a strange patch of tech history: April 1, 2004, was when Google introduced Gmail, and April 1, 2016, was when Tesla unveiled the Model 3.
What happened after that sale is the part that still defines it. Yahoo paid for a business that was losing money, but it was really buying the market’s faith that the internet would eventually justify almost any price. On April 1, 1999, that faith was worth $5.7 billion, and Cuban walked away at the top of the boom.
