Reilly Brennan is an early stage investor in the transportation industry and a lecturer at Stanford’s School of Engineering. As cofounder of Trucks, a venture capital group that funds the future of transportation, he has played a crucial role in the development of self driving car technology and other advances that will modernize the way we move from place to place. In this conversation, he explains to Payson how transportation touches every part of life, the thousands of decisions that go into evaluating young entrepreneurs, why he invests in the person over the idea, and how he uses the principles of cultural anthropology to assess the potential of the teams that pitch to him. As an avid sports fan, Reilly also has thoughts on the changing landscape of the industry, including the ways in which social media is making athletes more powerful than their sanctioning bodies, why young athletes shouldn’t wait to secure sponsors or results to start creating a personal brand, and what the NBA is doing right. Early in his career, Reilly was a member of the Le Mans-winning Corvette C5-R program, and watches car racing closely. He talks about why NASCAR isn’t what it used to be, why Dale Earnhardt, Sr. was the last of the great NASCAR drivers, and why the commoditization of the sport deliberately robs drivers of their personalities. 

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