Tyler Winklevoss competed in the coxless pairs at Beijing in 2008 with his twin brother, Cameron. They had begun rowing together in high school, and later rowed at Harvard College, where, in their senior year, they led the Crimson eight to an undefeated domestic record, winning the Eastern Sprints, the IRA Championship, and the Harvard-Yale race. In 2004 the Harvard eight also finished second at Henley. At the 2007 Pan-American Games the Winklevosses won a gold in the eights and a silver in the coxless fours.

While at Harvard, the twins, assisted by classmate Divya Narendra, started a college social networking internet site, originally called Harvard Connection, later known as ConnectU. They asked Mark Zuckerberg to join them and help expand the site to other colleges. Zuckerberg made this wildly successful, as ConnectU was the forerunner of Facebook. The four had an oral agreement about how they would split the profits. The Winklevosses were eventually bought out by Zuckerberg for $59 million, after they sued him for breaking their oral contract. But they filed a further suit seeking more money. In March 2011 that suit came to trial with the judge finding against the Winklevosses in April 2011.