How One San Francisco-area City Found the Road to “Cool”

“You have to ask who the city’s for.”

Ted Cuzzillo
The Startup
6 min readSep 13, 2019

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Imagine the moment your boss makes it clear why he hired you, and it’s not the reason he once gave you. You’re three months into your new job as chief innovation officer in a decidedly uncool suburban city near San Francisco. You’d been told the job was all about a new fiber-optic loop. Now, you hear, it’s all about making the place “cool.”

The moment comes at a city council meeting. The mayor bangs his fist on the dais and says to council members and staff, “Look, I just want this city to be cool. Could somebody tell me please how do we get this city to be cool?”

CIO Deborah Acosta recalls, “I said to myself, ‘OK, I got it.’” She knew even before that that no one was going to move there for infrastructure alone. But they would move there if they thought [the city] was cool and innovative. She says, “So that’s what I set out to do.”

What’s it take to lead a city to cool? What is a “smart city”? Today, looking back at just over five years on the job, Acosta⁠ has some answers.

Cool comes from underground

For longer than most locals can recall, San Leandro has seemed anything but cool or smart. In the decades I’ve driven past it, I’ve known it only as a long, drab stretch on the 880 freeway. It’s hard to tell where it begins and ends, but generally it lies a few minutes south of Oakland’s rail yards and far north of Silicon Valley’s heart. It commands two stops on the regional rail transit system, one to serve a mall built in 1957.

Even as Acosta set out on the way to “cool and innovative,” she knew a large part of that aura rose from the stuff that ran underground.

“I’m an absolute infrastructure freak,” says Acosta. If the city can’t provide a fiber connection, your businesses and residents won’t have the speed needed to send and receive audio files, video files, and vast tranches of data. “The latency would kill us.”⁠

When she arrived on the job, the city had just started rolling out the fiber-optic loop. One company that immediately benefited worked with the Oakland Raiders football franchise. Over copper wires, its New York-bound video files took nine hours to upload. On fiber, it took five minutes.

But any technology project is risky, and many projects are a gamble that’s tilted toward the downside risk. Projects with potentially useful outcomes can easily fail and leave the city with precious time wasted and ghosts under the streets. One company proposed to the city of San Leandro a pilot project in which software would be embedded into the street surface. The city would have had to find suitable intersections, then endure the weeks of construction. “What would we gain if it failed?” Acosta wondered. “Just the knowledge that this kind of technology wouldn’t work for us?” It’s hardly worth the city’s time.

Some elements are simply beyond a city’s control. For one thing, their ability to monetize assets is under increasing pressure. A recent FCC ruling, for example, puts a severe limit on fees for leasing street poles — even as the cost to cities rises for planning and implementation.

The plan

A critical part of the road to “cool,” Acosta knew, was a plan. It has to be informed by research, by other people’s experience. It has to describe in detail not just what you’re building and why and but also who you’re building it for. And it must be available for anyone to read it and comment on it.

A plan comes in handy when vendors approach, and they do. “Solar companies just hear that you’ve got an energy project going on,” she says, “and suddenly they’re your best friend.” Transportation vendors want to put their equipment in your boxes. Companies that build trash-to-energy plants envision one in your immediate future. They all say some version of this: “Let us help you with this. No, we don’t know what else you have going on in the rest of the city, but all you need to do is focus on this one little thing over here.”

It’s all free, at first. The vendors promise to provide the city with the data they collect — except, of course, the proprietary stuff they collect with their own software. At this point, a background in intellectual property law comes in handy.

When vendors come calling, it’s a good time to hand them the plan. You say, “Read this first. Then let me know if there’s some reason for us to meet, if you think there’s a part of our plan that you can address.”

I imagine a scenario of undisciplined, scattered, and an ineffectual scattershot of tools and systems, a landscape of grand-scale apps. It all does a little bit of this and a little bit of that.

Such a scenario is especially hard for city staffs that may have fallen behind on tech trends.

It’s especially hard, as she says, for city staffs who learned their craft with slide rules and pencils. They need experts to guide them, but such consulting “This technology stuff is not easy to learn,” she says.

Consultants are waiting to help, of course. But how does staff wrestle old procurement rules, which require defined outcomes, to contract for undetermined outcomes? Acosta says, “The problem with innovation is it’s innovative.”

Homegrown

For all of vendor-made technology’s elan, the quality of genuine coolness may have to be homegrown — such some strategies Acosta used to good effect.

She says, “You invite people in to show them what a good time where you wouldn’t think you’d want to have a party.” One such place was the top of the Bayfair Center shopping center. You take them up to an unused parking lot with a view of the beautiful San Leandro Hills. They say, “‘Oh, this is very nice. What else do you have?’”

Another strategy came from Derek Lee, a recent Cal Polytechnic graduate who was trying to figure out what he wanted to do. One thing he did know was that he wanted San Leandro to be part of something cool. He was concerned, says Acosta, that his young friends from high school were going off to college and vowing they’d never return to San Leandro. They said, “It’s too boring. There’s nothing going on here. There’s no technology.”

She recalls Lee urging her to tap the city’s own entrepreneurship and innovative spirit that’s already there. Part of the program that resulted started “maker labs”⁠3 for high schoolers in automotive hardware, and they’re starting to integrate that with internet-of-things systems. It’s what some call “civic tech.”

It takes an ecosystem

The key to a smart city, she says, is that all of the important elements are integrated. Citizens and business people have to be aware of the thing you’re trying to do. They have to feel empowered. They have to feel part of what you’re trying to create.

If you’re not engaging citizens and businesses to help them feel empowered, then, she says, “You have to ask what you’re doing it for.”

In the next week or two, I’m actually going to exit off the freeway into San Leandro. A foodie friend of mine told me out of the blue the other day that San Leandro has “a whole bunch of really cool places to eat.” We’ve set a date to go try one of them.

FOLLOW DEBORAH ACOSTA

After just over five years in San Leandro, Acosta decided she could do better work outside. She’s teamed up with other thinkers and “other very smart people” to create a documentary series. They’ll travel to 10 different smart cities around the globe, beginning with San Leandro to find the critical elements between “smart cities” and the people who live and play there. Acosta⁠4 is the CEO and founder of WeAccel⁠.“ Its Linkedin page, while the organization’s own site is under construction, describes it as “a women-owned consulting firm that helps cities create sustainably strong economies and works with employers to improve their ability to attract, retain and advance women in their workplace.”

This article was published originally on my weblog, Datadoodle. That’s data for data and doodle for life. Founded 2007.

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Ted Cuzzillo
The Startup

A hybrid-journalist-industry analyst at datadoodle.substack.com. Traversing the faultline separating, people, technology, and narratives.