When Gabe Klein started his job as the transportation commissioner of Chicago, he put a sign on his door that he hoped would set the tone for his time in office.

“Chicago: Getting Shit Done.”

The sign served a dual purpose: first, it was meant to elicit the tone of Mayor Rahm Emanuel the no-nonsense politico who – to put it mildly – isn’t known to mince words.

But it was also designed to remind Klein as well as the transportation department’s employees of their goal: “to serve the people of Chicago – and fast,” Klein writes in his new book, Start-Up City.

The book isn’t so much an autobiography as it is a statement about how and why governments must do more to embrace an entrepreneurial approach. Klein’s unusual background makes him the perfect person to tell that story.

For starters, Klein, 44, is quite possibly the only person who has ever headed two big city transportation agencies. He led the transportation agency in Washington, D.C. from 2008 to 2010 and then Chicago from 2011 to 2013. Despite his relatively short time in each city, he made a mark on both places.

From a 2013 Governing profile of Klein:

During his short time in Chicago, Klein oversaw the launch of Divvy, a 300-station bike share program that dovetailed on the success he had with Capital Bikeshare in Washington, one of the biggest and most successful bike share programs in the country. Under Klein, Chicago also got its first protected bike lanes, began construction of the Bloomingdale Trail, started work developing bus rapid transit, and launched speed cameras for traffic enforcement in school zones.

His time leading two transportation departments is unusual enough, but how Klein got there is even more peculiar. Before taking over D.C.’s transportation agency, he had never worked a day in the public sector.

Typically, transportation directors are longtime civil servants, engineers or political players. Before getting the D.C. gig, though, Klein had worked as an executive at Zipcar, a co-founder of a food truck/catering business and director of stores for a major bike retailer. His degree is in marketing management.

“‘This is either going to be a disaster, or Gabe is going to be the best person we’ve ever hired for the job,’” Klein said in an interview with Urban Edge, repeating what then-D.C. councilmember Jim Graham told him before he was offered the gig. “I have to admit, I thought the same thing. When they recruited me for it, I thought it was a bizarre fit.”

But Klein says the mayors who appointment him – Emanuel in Chicago and Adrian Fenty in D.C. – were known for their unorthodox approach and desire to see results quickly. In other words, he wasn’t picked in spite of his business background. He was picked because of it.

As Klein sees it, government agencies have often been too afraid to take risks and too worried about screwing up. He hopes that by adopting the ethos of high-tech start-up – focusing on the customer, deviating from the status quo and not being afraid to fail – governments can innovate and serve citizens more effectively.

Start-Up City, Klein says, grew out of the frequent questions he received after leaving Chicago. How can you work quickly in a bureaucracy? How do you find money when funding is tight? And how can you convince governments to market their successes? “It’s a handbook for change, but it’s fun to read,” Klein said.

Klein also discusses the future of urban transportation, focusing on the advent of autonomous vehicles as well as connected vehicles that communicate with each other. Those two technologies, he believes, will be the most significant changes to the way people move around cities in our lifetimes.

As long as governments don’t mess it up.

“I hope transit agencies and governments become the arbiters and coordinators of all these services instead of actually trying to run one mode themselves, then protecting it at all costs,” Klein says.

He also worries that if city governments aren’t careful, they could undermine the progress they’ve made it developing pedestrian-friendly communities if they come to rely too heavily on automated vehicle technology.

“What we need is a very balanced approach,” Klein says. “We don’t need to prioritize technology for the sake of technology. We need to prioritize people. That’s why I … and lots of others have focused on pedestrians, first and foremost, as the indicator species for a healthy, happy, well-rounded city.”

Check out Episode 3 of the Urban Edge Podcast featuring an interview with Gabe Klein