How Bill Gates spent long weekends at the beach alone with his venture capitalist ex-girlfriend Ann Winblad every year -
May 5, 2021

How Bill Gates spent long weekends at the beach alone with his venture capitalist ex-girlfriend Ann Winblad every year


Bill and Melinda Gates have had a decades-long agreement that the Microsoft boss could vacation for a long weekend at the beach every year with his venture capitalist ex-girlfriend. 

The odd arrangement raises eyebrows now that one of the richest couples in the world are going their separate ways after 27 years together and building a $130billion fortune.   

Bill, 65, and venture capitalist Ann Winblad, 70, dated in the 80s but broke up in 1987, the same year he met future wife Melinda. Ann was reportedly more ready for marriage than Bill as he worked day and night to build his billion-dollar Microsoft empire.

However, the pair maintained a friendship and in a 1997 piece in TIME Magazine, Bill said, ‘When I was off on my own thinking about marrying Melinda, I called Ann and asked for her approval.’

She approved and the former lovers – with Melinda’s blessing – kept their yearly vacation alive, with Bill spending a long weekend with Ann at her beach house on the Outer Banks of North Carolina. 

The pair spend their getaway every spring riding dune buggies, hang-gliding and taking walks on the beach. 

‘We can play putt-putt while discussing biotechnology,’ Bill said in the 1997 interview. 

Ann said, ‘We share our thoughts about the world and ourselves. And we marvel about how, as two young overachievers, we began a great adventure on the fringes of a little-known industry and it landed us at the center of an amazing universe.’ 

Bill and Ann first met in 1984 at a Ben Rosen-Esther Dyson computer conference. 

While in different cities, they began going on ‘virtual dates’ by going to see the same movie at the same time and talking about it on their cell phones. She even convinced him to stop eating meat for a short time. 

They broke up three years later, but in the TIME Magazine piece, Ann was quoted telling Bill that Melinda ‘would be a good match for him because she had intellectual stamina.’

The pair even got into business together and in 1999 Bill partnered with Ann on Hummer Winblad Venture Partners.  

Ann is married to San Francisco private investigator Edward Alex Kline, 63. Kline is the younger brother of actor Kevin Kline.

Bill and Melinda both posted the same joint statement about their divorce on Twitter Monday.


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