Jerry Yang is giving a quick tour of the conference room at his private investment firm in Palo Alto, Calif. It’s dotted with gifts and photos from his 20 years in Silicon Valley. Yahoo’s 45-year-old billionaire co-founder stops before a glass deal toy on a low table.
“Um, I have no idea what that is.” He peers more closely, checks the date: September 2012. “That is… that was after I’d gone. I think that was the last deal I worked on at Yahoo.”
The plaque commemorates what may have been one of the dumbest business decisions of all time. Yahoo’s board agreed to sell 523 million Alibaba shares, half of its stake, back to Alibaba at $13 apiece. Yang hadn’t been so keen to sell. They did anyway. By then he’d quit the board. Sure enough, Alibaba’s IPO last month rocked global markets. Shares of the Chinese e-commerce giant are now worth around $90. Yahoo still has a 16% stake worth $36 billion, but it left almost as much money on the table–some $35.5 billion–as its entire current market capitalization.