39. The Time Yahoo Passed on Buying Google for a Million
Year: 1998
Location: California
Company: Yahoo
Estimated Damage Value: $990 billion*
In 1998, Sergei Brin and Larry Page considered selling Google, now worth nearly one trillion dollars, to Yahoo for just $1 million. Yahoo’s refusal marked a pivotal moment in tech history, saving Google from a potentially undervalued sale.

Yahoo’s current $10 billion value pales in comparison to Google’s success, highlighting a significant missed opportunity. This decision led to Sergei Brin and Larry Page amassing fortunes of $49 billion and $51 billion, respectively, illustrating the profound impact of strategic business choices.