T.A. McCann, serial entrepreneur and Managing Director of Pioneer Square Labs, has sailed in two America’s Cups. How are sailing and startups alike? T.A. explains.

David Cohen was super excited when he realized that T.A. McCann—founder and CEO of Senosis (acquired by Google), Gist (acquired by Blackberry) and Rival IQ, a leader in marketing analytics, as well as Managing Director of Pioneer Square Labs — was the same guy he was reading about in The Proving Ground: The Inside Story of the 1998 Sydney to Hobart Race.

T.A. tells tales of his sailing adventures—including one harrowing anecdote involving Rupert Murdoch’s finger—and applies the knowledge he gained competing in two America’s Cups to running and growing startups.