What happens when a tech-minded entrepreneur is unexpectedly chosen to lead a big city government bureaucracy? Gabe Klein was an unconventional pick to head the District of Columbia’s Department of Transportation when he was hired back in 2008, by then-mayor Adrian Fenty. He’d been a Zipcar executive. He helped found a local boutique food-truck company. He grew up in a Virginia ashram called Yogaville. But he had never worked in government. Over the next 23 months Klein implemented a program of transformative innovation, rapidly rolling out bike-sharing, new bike lanes, streetcar plans and next-generation parking infrastructure. Now Klein is a year-and-a-half into his second unexpected job in government, as the head of Chicago’s Department of Transportation under Mayor Rahm Emanuel. Join MIT Visiting Scholar Aaron Naparstek in conversation with one of America’s most visionary and inspiring new urban leaders.