San Patricio, March 1st, 2025 — Darra Winston didn’t start with heavy machinery.



Sure, her company Roadbed Solutions owns heavy machinery now — a lot of it, as you might imagine for a plan-build civil engineering firm doing $93 million a year in business. But those backhoes, bulldozers and asphalt de-millers were not the first step.



Her first step involved a pickax and a bicycle.



“I was living up in Portland, back in the mid-1990s,” she begins. “I ended up dating this guy who was in a group that used to do ‘guerrilla depaving.’ They used to go find old parking strips and other bits of land that had been asphalted over and abandoned, then they’d rip out some pavement, scratch some native plant seeds into the soil and bike off into the night.” She laughs. “It all seemed so cool and romantic, when I was 22.”



“So, I started going along. And one night, we were sitting there trying to depave the back of a vacant lot. We were hammering away with hand tools and pry bars. I was trying to swing this pickax. Every time I hit the asphalt, I’d scatter a tiny little spray of aggregate gravel, and the blacktop was still there, barely dented. My hands were blistering. My back was sore. I looked at that vacant lot and I thought, ‘It’d take a month to rip this up.’ And I thought about the square miles of asphalt poured over the surface city. That was the end of that relationship but the beginning of my obsession with civil engineering.”

Winston went back to school, getting a planning degree at Portland State University. She worked for Portland’s Metro regional government on transportation and neighborhood planning. She married. Her husband was offered a job working for Google in 2007, so they moved to Menlo Park. She worked for a private consulting firm for a couple years, but found the work unsatisfying. “We’d been talking about starting a family, and after my first was born, I quit. Three kids and dozen year later, I woke up and it hit me: Boom! You’re a housewife!”



Like many women who spend an extended time outside the workforce, Winston found it hard to get back in. Feeling the need to network, she began volunteering on local commissions, serving on nonprofit boards, going to lectures and conferences. “It was a crash course in urbanism, and I met scads of interesting people, but I still couldn’t find the right job fit.”



Then, in 2017, she went to an engineering panel lecture at Stanford on the state of Bay Area infrastructure. She was stunned to hear that 28% of the roads in Bay Area cities were in “poor” or “failing” condition. She was even more intrigued to learn that a “wave of old roads” whose maintenance had been deferred for years, would be headed into crisis in the 2020s, pushing the share of poor-or-failing roads perhaps as high as 50%.

What’s more, because of the design of modern asphalt roads, roadbeds themselves — the stuff on which the asphalt sits — have a lifespan of about 40 years. The work that needs to be done on road that has been left un-maintained for thirty or forty years is generally much more expensive than bringing a well-maintained road back up to grade.

How expensive? Replacing failing roads with newly re-engineered roads can cost more than one million dollars per “lane-mile” (a strip of land one traffic-lane wide, and one mile long). The panel’s estimate that bringing all of the Bay Area’s roads up to date by 2030 would cost somewhere north of 45 billion dollars, and almost all that spending was the responsibility of local governments.



“I think most of the students in the room were trying to not pass out from boredom, but I was gobsmacked,” she says. “I’d worked in local government, I’d studied local transportation and I knew there was no way — no way! — that local governments were going to find 45 billion dollars to repair their roads. Except maybe San Francisco itself, none had that kind of tax base, even here. Most don’t have the bonding capacity and all cities have competing needs for the money they can borrow.”



“So, I asked myself, ‘If cities can’t repair their roads, what can they do instead?’”



Here’s the part where, in a thriller, we’d see our hero running through a montage of late nights, dusty books, and doors being slammed in her face. Winston began to research the question, staying up late nights and reading; sending email to experts; going to more and more obscure talks and lectures.



What would local government do? The short answer: No one knew.



The default plan across the region — across the United States — as far as Winston could tell, was to put off talking about it for as long as possible, then let future politicians and planners face the tough reality: their roads were not assets, they were liabilities.



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There was, however, another reality that also went undiscussed: American cities have too many roads.



For years, experts have noted that most streets — in all but the densest urban neighborhoods — are built to handle more traffic than they’ll ever see.



“It’s common to see residential streets with low-density, single-family homes that are 40 feet wide — or wider,” explains University of California urban economist Steven Whitstanley, “when maybe 100 vehicles a day travel that route. If asphalt was distributed according to need — rather than aesthetics — most neighborhoods could get rid of half, three-quarters (or more) of their paved surfaces.”



“In many neighborhoods, residents argue that road-space is needed, especially for on-street parking,” Whitstanley continues. “But in almost every American city, we grossly overbuilt parking beginning in the 1970s.” Whitstanley points to the “parking crater” studies that started being done in the mid-2010s, showing how much area of a given metro was given over to parking. (The most famous example being Los Angeles County where more than 200 square miles were covered with parking in 2015 — around 18.6 million parking spaces, or about 3.3 spaces for each car.)

(Image:Wikimedia)

In 2017, many entrepreneurs and investors were already looking to take advantage of another big trend: what business consultants were calling the “de-auto-mobilization of America.”



Whitstanley says, “It could also easily be argued, even then, that Americans had too many cars. The average U.S. car in 2017 was only being driven 75 minutes a day. And already you could see that ride-sharing services were taking a bite out of the need to own cars. And we knew autonomous vehicles would send ride-sharing into hyperdrive. Not to mention that the Baby Boomers were all about to lose their licenses — not at once, of course, but a steadily aging population means a steady less car-owning population. We built our transportation models on the idea that every adult owned their own car and drove it whenever possible. By 2017, we knew that model was dead.”



So, in 2017, the Bay Area faced a road maintenance crisis, the reality of overpaying, and the decline of the private car. Add that together and you come up with a pretty obvious solution: get rid of asphalt.



The only problem was, no one knew how to pay for it.



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“Leaving aside the politics of depaving — of how residents feel about you taking away their road — removing asphalt is expensive,” says noted VC-guru Max O’Hanrahan. “Sure, it costs less than rebuilding a road, but who’s going to pay for it? Where’s the business model?”



But Winston realized three things that others seemed to have missed.



The first was that though the asphalt needed to go, the right-of-way remained public property. “Under the roadbed, there’s real estate,” as Winston puts it now, “and valuable real estate at that.” While cities were short on cash, they had more roads than they knew what to do with.



The second was that once you had the big equipment on site, turning depaving into amenity creation was comparatively cheap. “You want a shared-use plaza with green infrastructure? We can do that. You want a linear park with bike lanes? We can do that? You want to prepare that ground for rebuilding, perhaps put a row of small cottages down the middle of the street? We can do that. We can put in whatever you need to sell depaving to the community.”



But Winston’s real breakthrough was her business model: local governments could pay her company in development rights. In exchange for the rights to develop a certain portion of failing roadbed into mixed-use buildings, Roadbed Solutions would finance the work itself. It would then turn around and outsource the development — from the landscape architecture and gardening to the building of new mixed-use buildings. “If we could get the money to launch these projects,” Winston says, “they’d turn a profit every time.”



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Where, though, would they get that money? Real estate development capital can be tough to raise for completely conventional projects. For complex, untried deals like this, Roadbed Solutions would need access to private capital that was willing to take some risks.



At one meeting with about a dozen investors, Winston recalls, an older man who’d made a fortune in software asked, “What’s the upside here? How much money are we talking?”



“45 billion,” she said, “In the Bay Area alone.”



Everyone in the room got it, at once. Max O’Hanrahan says he got it first.



“We’re talking” O’Hanrahan says, “about a gold mine: buying services without spending money is every elected official’s dream; and since the land was leased not bought, it wasn’t even a road vacation. All it took in most cities was a council meeting, and here’s how that went: ‘Yeah, we either can raise your taxes or give you a free park if we let this company build something on a surplus parking lot.’ Especially in struggling communities, that’s a no-brainer. The minute I heard Darra’s pitch I was like, ’Stop pitching and take my investment.’”



Officially, Roadbed Solutions’ business mission is to “harvest the value of underused real estate in exchange for solving automotive transportation maintenance problems and providing community-empowering amenities.”



Unofficially, O’Hanrahan jokes, it’s “Plow-up pavement. Plant parks. Harvest condos.”

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Winston started with one deal in East Oakland, in 2018. There, Roadbed Solutions repaired one eight-block stretch, put in a linear park, and got a 99-year lease to a road-end that backed-up against the highway. “Its major use was as a site before that was for torching stolen cars.” She then sold that right to a developer, who put in a four-story apartment building. “That was my proof of concept.”



It was in San Patricio that Winston turned her concept into success. City of San Patricio Mayor Jerry Gutierrez’s plan for that city is reducing its maintenance overhead while greening the city to make increased density more livable. In 2020, the City and Roadbed Solutions cut an initial deal on a five-year plan for a total of 600 lane-miles of depaving and parks. Winston’s company, in return, got leases on a downtown parking lot locals had long considered an eye-sore and on a large dead mall on San Patricio Island.



“I gotta tell you, meeting Darra Winston was like I’d made a prayer without knowing it and then had that prayer answered,” says Gutierrez now. “When this work finishes next year, we’ll have almost doubled our public park space, added 50 miles of bike lanes, and brought in needed housing to our community — all without a dime coming out of our operating budget. That’s huge for a town like us.”



With Roadbed Solutions about to celebrate its 5,000th land-mile of depaving and launching franchises in five other states (with a goal of “upgrading” 100,000 lane-miles by 2030), it’s about to be huge for a lot of other cities, as well.

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This is the fifth short story in the San Patricio series, which is journalism from the future about a California suburban struggling with rapid social change and disruptive sustainability.