Winblad isn't the only woman to ever date Gates, but the gregarious, outgoing, and refreshingly frank 5-foot-something blonde is the one who never hesitated to discuss the association with candor, including the Microsoft captain's lax personal grooming habits.
 
In the Silicon Valley smog of double-talk and superstitious marketingspeak, Winblad's incisiveness is her trademark. The software engineer started her own business in 1976 with 500 borrowed dollars, then sold it in 1983 for over $15 million. After consulting with Apple, Microsoft, and others for several years, she was finally persuaded by ex-NBA basketball player and then venture capitalist John Hummer to bring her know-how to an exclusively software investment fund. Located across the San Francisco Bay in Emeryville, California, and worlds apart from the Ivy League boys club of shady venture capital enclaves in Palo Alto, Winblad and her partner were outsiders in more than one way. At first derided as "Goldilocks and Lurch," the team have become respected, if not insiders.