The former D.C. transportation leader reflects on taking his show on the road.

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 had helped found a local boutique food-truck company. But he had never worked in government. Over the next two years, he rolled out bikesharing, new bike lanes, streetcar plans and next-generation parking infrastructure – and along the way, he created a lot of fans among smart-growth advocates.

Then came the 2010 election, and his boss lost. Incoming Mayor Vincent Gray opted not to keep Klein, who by that time had gained a high enough profile of his own that there was speculation he might run for city council. Ultimately he decided against it.

Now Klein is six months into his second unexpected job in government, as the head of Chicago's Department of Transportation under Mayor Rahm Emanuel. He was back in Washington this week for a few days, and we caught up with him to hear more about what he has planned for the Second City, why he went there in the first place, and what a tech-minded entrepreneur is supposed to do with a town that has already sold off all of its parking meters.

You’ve mentioned that you had only been to Chicago twice before you started working in the administration there last summer. Does that mean that this job is really more about understanding the broad ideas and priorities around livability and accessibility, and that it doesn’t necessarily require that you know the Chicago street grid off the top of your head?

Right. In every job, you have advantages and disadvantages. Not having ever worked in the government before, my advantage here [in D.C.] was knowing the city well. [Former transportation chief and later city administrator] Dan Tangherlini brought me to the job. I had worked with him when I was in the private sector at Zipcar. He knew me, he knew what I was about, he knew I was about private sector innovation, public-private partnerships. He wanted that on the inside looking out. Going to Chicago, the advantage is that I did a tremendous amount of work in less than two years – 23 months to be exact – [in D.C.]. Mayor Fenty liked to say, “I never said I wanted to be mayor for 12 years. There are people before me, and people after me that have and will be mayor for 12 years. I’m more than happy to do 12 years worth of work in four years and move on and do something else at the age of 39.”

In many ways, I feel the same way. I would have gladly stayed had we won, because we would have done some amazing stuff that we had planned. But the fact is, I got so much done in two years building on what Dan had done before me, that directionally we changed things so much that you can’t go back, you can’t stop the progress. So going to Chicago, I know how to do that. My goal is to get a tremendous amount of work done in four years for the people in Chicago. And also on a personal level, to prove to myself that I can do it in two cities. That hasn’t really been done before. Janette Sadik-Khan has done some amazing work in New York, the new guy in San Francisco is doing some great stuff. But I don’t know if anybody has ever really transformed – or started transforming – one place, and then really done it in another city. So I’m very excited to do that.

I never thought I’d be in government at all. I thought this thing in DC was a one-off, it would be a great experience, and I have a lot of things I want to do in the private sector. But when I met Rahm Emanuel and we started talking, and I realized how exciting his vision was for Chicago, and I also realized how important Chicago is to the U.S.

Is it at all strange, or maybe enjoyable, for you to come back here and see the bikeshare stations all over the place that are proliferating, and to see the things that you essentially permanently lodged into the city that did not disappear when you lost your job?

Some of the stuff I’m really proud of. People don’t even know how much work we did. All the new meters and the pay-by-phone parking system, it’s the biggest system in the country, if not the world, and it’s a permit system that we built ourselves from scratch. I’m incredibly proud of the work that we did, and the team here. I think fundamentally what I brought to the table that was different was the ability to say “yes,” and to align people around a vision. There’s a whole lot of nay-saying in government, “it can’t be done, it can’t be done, you can’t do that, we’ve never seen that done before.” Basically, I was ignorant of that. To me, it was a huge opportunity, a billion-dollar budget, a lot of control, the ability communicate directly with the public and build a coalition of support.

That’s the other thing I brought to the table – my ignorance of government. I view it as just a big business. And for me, the only value in business is if you’re working for the greater good, if you’re doing something positive. I was like, “well this is the most positive business you could be in, and it’s an incredible amount of responsibility.” There’s a responsibility to be transparent, there’s also a responsibility to market your services and not to feel like you automatically have a monopoly just because you do. It’s easy to get shitty service, for lack of a better term. We started calling the public our “customers” – there are all these subtle things I tried to institute. We filled potholes in 48 hours. We did live chats with the public once a month to get their live input unrestrained, unrestricted. We started one of the most active twitter accounts in the country for a government agency. What we really did was we put a graphic-user interface on the front of the agency to give people a window in to what we were doing.

Did you think in the hiatus between when you left the government here and when you were offered the job in Chicago that you were done with government?

Yes. I had a couple of state DOTs that made me offers. They were wonderful governors, but at the state level, you’re more of an administrator and less of an innovator. All of the innovation for the most part is happening at the city level. It didn’t really interest me. So I wrote a business plan that I was shopping around, I was also looking at some private-sector opportunities. Then I started working on the transition for Chicago, just trying to help. And I realized over time that there was an interest in me [for the job]. I’d also been here for 15 years, and I’m always up for an adventure. Life is short, and I thought this is going to be an adventure, an opportunity to make real change and continue the work that I did here.

So you’re not following the Gabe Klein Masterplan where you get fired and hired at city DOTs all the way across the continent until everyone has bikeshare and smart meters?

No. Absolutely not. This will be my last city DOT director job. I was only going to do one. Sort of like Michelle Rhee said in Waiting for Superman, “I could do whatever I want!” The interviewer is like, “why?” “Because this is the only chancellorship I’m ever going to have, I’m not worried about setting myself up for the next job.”

Does the job feel fundamentally the same in Chicago? Or are there substantially different issues there? For example, freight is a huge deal in Chicago, and now that’s part of your job.

Freight is huge. It’s very important. These projects move slower, but they’re really, really crucial. So I’ve learned a lot about the freight industry. The public space situation is different because Mayor Daley did a long-term lease on the [parking] meters, for like 75 years. And when you lose control of your meters, you lose control of a lot of your public space. We still are going to do some amazing stuff with public space, but it’s different. Transportation departments are really public space departments, and transportation. And a lot of people don’t realize that.

Chicago is also a huge city, it’s 225 square miles, and it’s 60 [in D.C.]. So it’s immense. We have marshland on the South Side, and a Ford factory. We have some of the densest land in the country in the Loop, and sleepy bungalow neighborhoods. It’s amazingly diverse.

You brought an entrepreneur’s background to the job. But are there things that you learned in Washington about the political reality of the job that’s helping you in Chicago? One of the things you faced in D.C. was that there was hostility toward your livability and walkability projects because there’s this perception that they’re only meant for young, yuppie professionals.

It’s like “We don’t want to be Europe, we don’t want to be Canada.” Heaven forbid we’re Canada, right? Canada is second in the world for education, we’re now 22nd. They have free health care, they have a wonderful transportation system that they invest in. So heaven forbid! By the way, they watch the same crappy television, and eat the same crappy food. They look like us and talk like us. But they have a very different fiscal situation, they don’t have an army. So it’s interesting to look at the choices they made versus the choices we’ve made. And for some reason there are people in this country that are hell-bent on this “American exceptionalism” argument, and I think there are people out there having a hard time reconciling that when you make bad decisions, there are bad consequences. We as Americans sometimes think that no matter what we do, we’re Americans! Well, yeah. But if we don’t invest in our transit systems, they’re going to break down, and more professional jobs are going to go overseas. What I love about working for our mayor in Chicago is that he gets the connection between innovation, seamless transportation and having the best job force in the world.

Does that mean that you’ve learned how to talk about, say, why we need bike lanes in a way that doesn’t conjure in peoples’ imaginations that everyone here should act like they live in Denmark?

The mayor actually does a great job of that, the mayor talks about it. Adrian Fenty was all about innovation, but like most mayors he wasn’t focused on transportation as a key part of his platform. But he got it and he let me do what I wanted to do. In Chicago, from the get-go, [Emanuel] wants to do this stuff because he understands that to be a world-class city, you have to do this stuff. It’s not optional any more.

Were there any projects or ideas that you wanted to get to in D.C. that you didn’t, that you think you'll be able to try out in Chicago?

Yes and no. One of the things I was very passionate about here is parking innovation, and we were leading the country along with San Francisco in piloting different solutions for public space and parking. We innovated a lot, incrementally, because we didn’t have money for it. Now they’ve replaced almost every meter in the city with digital smart meters that talk to each other. In the old days, you put a quarter in and it gets stuck, the meter’s out for days. In the new system, we know before the customer does. Then we layered pay-by-phone on top of it, so that anybody can pay with a cell phone, and revenue like doubled. And we were testing sensors in the streets. What we were heading toward was a dynamically priced parking system, where the price of parking would depend on the utilization rate, and we could feed information to your phone or your car. So when you’re getting ready to leave and drive into the city, you can see that parking is a total nightmare in Adams Morgan, and you’ll probably take the Metro in. Or hey, you’re in the city and you want to park on U Street, it’s going to cost $4 or $5 an hour, but if you go two blocks back, it’s only $1.50. Managing congestion with pricing, that was something we were going to do this year. And we were going to launch a ton of bike facilities. That has slowed down with the new mayor.

Would you have to stay in the job in Chicago 75 years if you wanted to play with any of these kinds of parking ideas there? Are you going to be able to touch that at all?

I don’t know. I haven’t read the whole contract, I don’t interface with the parking vendor too much, they really deal with the revenue office. I’d like to think that they’re going to want to innovate and work with us, but I don’t know that. When you don’t control anything, it’s hard to put a lot of effort into that. As a business person, you look at where you can have the most impact and get the most return on an investment. And with the parking situation there, it’s probably not the best use of my time, but I’d like to make some inroads.

Public spaces, though, I think we can still do some pretty interesting stuff. We have about 56 plazas around the city that we’d like to find a way to activate.

Meaning turn them into places where there are amenities like cafés?

Yes, like people places. So we’re going to work on that. I worked on streetcars [in D.C.], [in Chicago] we’re going to do bus rapid transit, which is cost effective and we can do it more quickly. And the mayor is very focused on a lot of bike facilities. He wants it to be the bike-friendliest city in America, and it’s perfect for biking. It’s flat, it’s a grid, and you can get from one end to the other without going uphill at all. So we’re going to do that, and the bikesharing is going to be huge. And lots of other stuff.

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