Start-Up City: Inspiring Private and Public Entrepreneurship, Getting Projects Done, and Having Fun

Start-Up City: Inspiring Private and Public Entrepreneurship, Getting Projects Done, and Having Fun


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Product Details

ISBN-13: 9781610916905
Publisher: Island Press
Publication date: 10/15/2015
Pages: 256
Sales rank: 830,302
Product dimensions: 6.00(w) x 5.90(h) x 0.60(d)

About the Author

Gabe Klein is the former DOT director under Mayor Rahm Emanuel’s administration in Chicago and former Director of the District DOT under Mayor Adrian M. Fenty. Before working in local government, Klein worked at a few startups, including Zipcar. In 2015, in addition to his other roles, he joined Fontinalis Partners as an SVP (Special Venture Partner) on their new fund. Klein continues to advise a number of technology and mobility companies, including Transit Screen and Phone2Action, where he provides leadership on strategy. He is on the board of NACTO and Streetsblog. 
David Vega-Barachowitz is the former Director of the Designing Cities initiative at the National Association of City Transportation Officials (NACTO). He is currently pursuing his PhD in urban planning at MIT. 

Read an Excerpt

Start-up City

Inspiring Private & Public Entrepreneurship, Getting Projects Done, and Having Fun

By Gabe Klein, David Vega-Barachowitz


Copyright © 2015 Gabe Klein
All rights reserved.
ISBN: 978-1-61091-690-5


Lesson #1

Don't Be Afraid to Screw Up and Learn

It is necessary to make mistakes. Just make them as quickly as possible, learn from them, and try not to repeat.

When I was announced as director early on New Year's Eve at the DDOT headquarters with the mayor and D.C. press present, it seemed as if the whole of the agency was standing on the balconies overlooking the atrium. Even as I gave my opening speech, I could sense the skepticism amongst some in the crowd of transportation employees. Who was this smart aleck from the private sector they'd brought in to shake things up? Why did things need to change?

When the announcement came to a close and the DDOT ranks began to form a line to shake hands with their new director, a middle-aged woman with a familiar face approached. She held a firm regulatory grip in her role as program manager for public space for DDOT and had proven to be somewhat of a nemesis while my food-truck company, On the Fly, struggled to survive on the streets of Washington.

"Should I just pack up my desk now?" she asked half-jokingly under her breath as she shook my hand.

"Absolutely not," I said. "I'm going to make you my food-truck czar." I smiled, half serious.

This person wasn't the problem, but her approach was symptomatic of an ingrained culture of risk aversion and an antagonistic attitude toward the private sector. I knew that something, probably a lot of things, had to change at DDOT, and that her actions were a partial reflection of issues throughout the agency, and government as a whole.

For the next few years, I worked with this manager and many of the others in the agency to change not only their attitude about their sometimes adversarial role in relation to the public and businesses, but also to set a new open-minded tone internally and externally for their teams, and their teams' teams, as they interacted with the public.

Within the first few weeks, I took stock of a few fundamental problems at DDOT:

• Saying "yes" meant more work, especially in an era of dwindling resources. This meant that there was very little incentive to innovate or to say "yes" when someone within the agency, or a customer of the agency, wanted to do something different from the status quo.

• Stepping out on a limb meant increasing risk of failure. The aversion to failure was unlike anything I had seen before, and, as I learned later, was actually even higher in many other cities.

• There was a prevailing attitude that businesses and the private sector in general were "on the other side" and were exploiting our city resources for personal gain. All businesses — small or large — were seen as the same by many managers.

• Government defaulted to a black box and was often opaque and uncommunicative in general, and especially when project problems became public or convoluted.

I was taught to iterate and fail fast as a survival instinct in business.

This last issue surprised me. If I was going to try to sell change to the public, how could we resist giving information to people? It just wouldn't work. But this was the standard way that things were done at DDOT, and at many government agencies. Right off the bat, I realized that the best effort that I could make would be to lead by example: the director of the agency, like the mayor, sets the tone for embracing change and risk. I personally had to show that I was willing to embrace the future now and take on risk. Otherwise, we would never accomplish anything and would be stuck in a cycle of uninspiring, incremental change.

In the start-up world, "failure is not only invoked, but celebrated."

Coming from the start-up world, the idea that I was supposed to be risk averse and instinctively say "no" made no intuitive sense to me. I was taught to iterate and fail fast as a survival instinct in business. We never would have ended up with convertibles or pickup trucks at Zipcar without this philosophy. In the start-up world, "failure is not only invoked, but celebrated." This has been a basic tenet of technology startups for decades. In Walter Isaacson's book on Steve Jobs, he tells the story of the iPhone launch event, where the thing literally did not work and was sporadic at best, an amalgam of iPod, phone, and computer, with nothing quite functioning as it should, even minutes before the event. Jobs held the unveiling anyway, and miraculously, when he made that first call from the stage, it went through. If he had given up because the product at that time was unreliable and a borderline failure, where would Apple be now?

So I set the expectation that we were going to experiment, make mistakes, and then make more responsible long-term decisions for the taxpayers as a result. This became the new modus operandi and freed up our teams to take risks.

My first week on the job, I went to work meeting with stakeholders inside and outside of local government in D.C., as well as in other big cities. Mayor Fenty had spent time in New York City meeting with Mayor Bloomberg, and emulated quite a few things he learned there. He mimicked Bloomberg's bullpen office layout, in which he sat in an open cubicle with all of the mayoral staff, setting a dramatically different tone for government business (cobwebs literally grew in his sixth-floor official office, he used it so little).

New York City was doing the most interesting public space and active transportation projects in the nation at that time, and had one of the most progressive and energized teams. I met Janette Sadik-Khan, Mayor Bloomberg's transportation commissioner, at the end of 2008. Janette had already made a name for herself as a change agent by making much of Times Square into a pedestrian zone. Janette and I shared a lot of ideas, both during this meeting and after, but perhaps the most important thing she told me was to think of many of our projects as "pilots," if not in name then by approach. This strategy of experimentation and trial-and-error resonated with me. Moreover, it was cost-effective, because we could use cheap materials and fast action by internal teams to show a project's worth and build a constituency, and then find the funds to make it permanent later on. This also meshed perfectly with my "fail fast" start-up philosophy, and also with my life philosophy more broadly: It's okay to make mistakes, just make them as quickly as possible and learn from them. We also discussed the importance of documenting your work and publicly stating your goals in a way that government traditionally shied away from: short-term, milestone-based targets to measure against. Again, this was a perfect fit with the private-sector yearly strategic and budget plans that I was used to.

As a new guy with no experience in government, planning, or engineering, I set about asking a lot of questions, many of them "dumb" questions that would have seemed obvious to anyone who had spent time in municipal transportation. I got different reactions from people. The technical "experts" gave me an eye roll and must have thought, "Who hired this guy who doesn't even understand the federal funding formulas?" Others were delighted at the prospect of a refreshing, energized, and youthful director who didn't mind baring his lack of knowledge about the bureaucracy he had walked into, but was also asking everyone for input on his agenda. I had hundreds of conversations, with my assistants, the heads of the divisions, and everyone in between, asking, "What do you think is important that we do, that we don't currently do?" I gathered small groups that cut across the agency and presented my rapidly growing vision for the next two years. People seemed to really appreciate being heard as well as the idea of increasing the pace of change. When I started talking to people about the detriment of saying "no" to new ideas and instead encouraging staff, and the public, to float any idea they saw as worthwhile, I got a bifurcated response: excitement at this attitude from the planning group and the communications and government relations folks, and then an "ugh" from the engineers and civil technicians. I knew that some of the best ideas were going to come from laypeople, those who live, work, and play in their own neighborhood. We needed to engage and empower them.

The combination of trying new ideas, failing fast, and doing low-cost pilot projects was a lot for some people to stomach, even for me as I tried to learn all of the government protocols. In my first few months, I bungled a few things (following my own philosophy as much as possible). At one point, shortly after starting, I accidentally contradicted the mayor in the Washington Post regarding the funding of late-night Metro subway service from the Washington Nationals stadium. In hindsight, this mistake wasn't that big a deal, but at the time, it felt like a critical error. The mayor called me. I apologized profusely for not paying attention to his stated policy and told him it would not happen again. He responded, "All that matters is that you are willing to take responsibility for a mistake and move forward." When your boss has your back, it gives you the freedom to take risks and experiment more boldly. My boss's great example reinforced my own resolve to experiment.

Richard Branson, in his autobiography, Losing My Virginity, tells a great story about the redesign of the interior of the Virgin Atlantic fleet in the 1990s. When Virgin started installing the new interiors on the planes, a host of design problems surfaced, the sum of which cost Virgin millions of dollars as they struggled to salvage the overhaul. However, instead of firing the designer responsible for the snafu, Branson did just the opposite. He asked the same person to design the interior again, and this time, to succeed and prove himself. The designer did just that, and the resulting interior proved to be a seminal, award-winning design, as well as one that could have been carried out only by an eternally grateful, loyal employee hell-bent on salvaging his own reputation.

I knew that some of the best ideas were going to come from laypeople ... We needed to engage and empower them.

Learning the hard way: The Pennsylvania Avenue bike lanes snafu

There are, unfortunately, times in management when you must assert your leadership by altering a design, critiquing a plan, or prodding your staff to do more by elevating expectations. Yet most often, whether you are the manager or the managed, such errors and misgivings provide opportunities for teachable moments.

Shortly into the first year of my tenure as DDOT director, I heeded a challenge put forth to me by Rep. Earl Blumenauer of Portland, Oregon. A stalwart of the sustainable transportation field for decades, Blumenauer had long fantasized about a bike lane on Pennsylvania Avenue in Washington, D.C., between the White House and the U.S. Capitol, and the national and local statement that it would make about the importance of active transportation.

As a student of history who was also working on the streetcar system vision and plan for Washington, D.C., I knew that the middle of Pennsylvania Avenue had once carried a streetcar line. This was, in fact, the last streetcar to run in Washington, D.C., before it shut down in 1962. In the original 1791 plan for the District by Pierre L'Enfant, the avenue had been designed as a grand boulevard with a park running along its center. This and many other proposals had gone unrealized (or been erased), leaving, in the wake of the streetcar's removal, an asphalt expanse commonly used as a staging ground for government vehicles.

Pennsylvania Avenue wasn't ideal for conventional bike lanes. There were constant right turns and poor sight lines, and the overall width of the street made cyclists along the curb feel exposed. Although traditional bike lanes proved inadequate in concept, the center median presented an intriguing possibility for experimentation. Not one of the engineers said, "It can't be done." So we went forward with the project full speed.

I consulted Mayor Fenty on the project early on. He said that he was fine with the lanes in concept as long as they were safe and aesthetically suited Pennsylvania Avenue's stature as a grand boulevard. He embraced the idea of using the empty space in the middle that once housed the streetcar. Over the course of several months, we met internally with our bike lane task force that crosscut the agency and had planners and engineers working together to further develop this and other bike lane projects. I made regular appearances at these weekly meetings to reinforce the importance of Pennsylvania Avenue, monitor progress, and make sure that the engineers were saying "how" instead of "no."

With my broad portfolio of projects, including the 11th Street bridges, myriad streetscapes, and a new D.C. streetcar, I took my eye off the ball for a month or so as the bike lanes reached final design. Our staff and consultants had finalized the engineering and were ready to go into construction. The last I had looked at the schematic, we were 80 percent of the way there and everything looked fine.

There are many lessons to be learned from this project, and the first is to regularly check in on major milestones with your team. I failed to see the design decisions at 90 percent and 100 percent completion, and I paid the price for my mistake.

As the crews started scraping up the old markings and setting down the new ones along the first three-block segment, I received an urgent call from the city administrator. Something didn't look right with the new bike lanes. He told me to come down to see it ASAP. Then Mayor Fenty called me and said, "Director, I don't think this is what we talked about, you need to come down here and see what they are doing." I called the team, told them to stop, and went down to the site, the United States' "Champs Élysées," and the center of the universe for American politics.

To my horror, the design being applied to the street looked completely different than what I had last seen, and instead of taking the center median as had been agreed upon, the engineers left this space empty, and instead took one travel lane on either side of the median space. I was mortified. I had unintentionally deceived my boss and all of our other stakeholders, including those at the federal level. Worse, these bike lanes were completely unsafe and obtrusive. Why? Drivers were instinctively driving down the auto lane–width bike lanes, which could hardly be differentiated from the travel lanes that were there beforehand. How could this have possibly happened!?

By the time I called the crews to stop working, they had already striped three blocks of the avenue and the blowback was coming. Taxi drivers, AAA, reporters, and council members in the Wilson Building were all asking, "What the hell is this, Gabe?" They had caught me with my pants so far down that I broke a cardinal rule: I tried to defend DDOT and the current design to the mayor, the city administrator, and others, rather than admit my lack of oversight and move on right away.

So what had happened? As best as I can tell, the consultant designer/engineers, our planners, and our traffic engineers had a massive groupthink lapse. While I had been preoccupied with other projects, they had reverted back to an earlier idea, and what they knew versus what was possible, convincing themselves and each other that this was the better way to do the project. I failed as a leader by neglecting to check their work when I knew I should have on such a highly visible and symbolic project. As built, the design was politically untenable, aesthetically inadequate, and to the average rider, patently unsafe, even though this was the primary objective of the project.

Sometimes things look one way on paper, or work from a technical standpoint, but prove disastrous when implemented. Laypeople, those without the credentials or the signatures or the jargon, often catch these fatal flaws immediately on sight. In this case, our team, fearing the unprecedented, had taken two travel lanes and turned them into bike lanes at close to the same width, rather than reusing the median as a center path. Cars didn't know what to do, bicyclists were overexposed, and the median — the ingenious centerpiece of the project — remained conspicuously empty, still as hollow as the day the streetcars had been removed in the early sixties.


Excerpted from Start-up City by Gabe Klein, David Vega-Barachowitz. Copyright © 2015 Gabe Klein. Excerpted by permission of ISLAND PRESS.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
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Table of Contents

Why Should You Care About Getting S*it Done in Cities?
Chapter 1. Lesson #1: Don’t Be Afraid to Screw Up and Learn
It is necessary to make mistakes. Just make them as quickly as possible, learn from them, and try not to repeat.
Chapter 2. Lesson #2: Manage S.M.A.R.T.
On managing others, empowering your team, and shamelessly promoting their accomplishments
Chapter 3. Lesson #3: Where there’s a will, there’s a way
On how to evaluate your budget quickly, assess and align your stakeholders, and build beautiful cities (in no time)
Chapter 4. Lesson #4: Sell Your City 
On marketing your projects, communicating with the public, and celebrating the dastardly
Chapter 5. Lesson #5: Fund Creatively
On how to find funding where none seemingly exists, making the most of a slim budget, and getting creative with the basics
Chapter 6. Lesson #6: Bridge the Public-Private Divide
On forging a proactive bureaucracy, and making life better for everyone in the process
Chapter 7. Lesson #7: Prepare for Disruption
On the present and anticipated technological shifts and business models that are transforming urban life and challenging the status quo 
Chapter 8. Lesson #8: Drive Change
Understanding the implications of autonomous, connected mobility, what it means for cities, and how government can make sure they are driving change, rather than reacting to it
Conclusion: The Big Picture and You

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