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Sky joined Joby Aviation as a board member and investor in 2016. He is focused on anticipating technological paradigm shifts and builds private and public companies that use technology to enrich society. Sky founded internet service provider EarthLink, which he took public in the late nineties. In 2005, he founded Boingo serving as CEO and then as chairman, again taking the company public. Sky is also an investor and board member of Age of Learning, Swarm, Diffbot, Arty, and co-founded City Storage Systems. A venture partner at Craft Ventures, he is also a turbine-rated pilot.