The Domestication of the Skateboard: San Francisco Battled Its Skateboarding Community for Decades. Then Silicon Valley Stepped In.

Standing 6 feet, 6 inches tall, with a barrel chest and legs like tree trunks, Colin Sebern almost exceeds the size limit for his electric skateboard. Nonetheless, it's become his primary mode of transportation. He averages about 6 miles a day, mostly riding from his home in Potrero Hill to his girlfriend's house in the outer Richmond, or tooling around the Google campus, where he works as an engineer. He's paraded it for co-workers, supervisors, and a group of cops at a Giants game who asked for a test ride. (Sebern obliged.) He's put his pug on the board and filmed it. Sebern has used the board so much, in fact, that he's had no need for the sleek Audi S4 he purchased in 2011; it's only clocked 60 miles since March.

Sebern is a new breed of skateboarder in San Francisco: someone who's concerned about transportation rather than stunts. And fittingly, the board he rides is a far cry from the wooden, skull-decorated things that glided along Justin Herman Plaza in the '80s and '90s; this iteration, with its wireless speed control and thumb brakes, is a lot closer to a Tesla. It's meticulously engineered, says Sanjay Dastoor, whose company, Boosted Boards, mints these products from a warehouse in Mountain View. The electronic parts resemble those used in drones and hobby airplanes; the battery is strong enough to run for 1,000 kilometers (about 621 miles).

“And you can charge [it] off a normal wall outlet in 15 minutes,” Dastoor told an audience last year during a TED Talk. The audience listened raptly. This was a new, utopian vision for skateboards.

For anyone who's followed skateboarding history, though, this brave new world of TED Talks and self-propelled commuting devices seems counterintuitive.

Skateboards have long represented a feral subculture. They're the preferred vehicle of thrill-seekers and kids whose parents never put them in organized sports. They encourage misuse of the urban landscape — handrails, ledges, plazas, and empty swimming pools all co-opted in the name of technique and adrenaline.

Electric boards, in contrast, fall neatly within the parameters of accepted use of public space. They use roads as roads, rather than as thrill rides. As such, they're a vehicle for the establishment: college students, startup founders, eco-minded commuters. They're powered by onboard computers that obviate the need to kick and push — a rider is, for all intents and purposes, just a passenger. They cost between $1,000 and $1,500, up to 15 times the price of their wooden antecedents. And they enshrine all the values of Silicon Valley: speed, efficiency, scrupulous engineering, and a glossy patina.

Dastoor's line of Boosted Boards has become an emblem in San Francisco's culture war, alternately celebrated and sneered at. TechCrunch writer Josh Constine called them “magical”; local blogger SFCitizen deemed them a toy. (In September, SFCitizen posted a sassy pictorial essay about a “heroic tech bro effortlessly skateboard[ing] all the way through the Twitterloin up Larkin,” thumb-throttle in hand.) To some, electric boards are a fait accompli in a city with a sweet tooth for innovation. And they could, maybe, finally resolve San Francisco's decadeslong battle with its skateboarders.

But, as with so many other disruptions in the city, electric boards could be the next front in a larger and more complicated battle. It partly boils down to how the curbs should be used. More fundamentally, it's about who controls them.

Pro skater Karl Watson tries not to hate on the new technology, even if he's nostalgic for a past era of San Francisco skateboarding — one that propelled him to fame.

Watson began skating in 1987, when he was 11 years old. At that time Justin Herman Plaza was the center of the skateboarding universe, known for a sinuous cement embankment that skateboarders called “The Wave.” In the '90s, local skaters began filming themselves as they pirouetted over the plaza's steep ledges and circular berths, backing their stunt-filled ballet with a hip-hop soundtrack. An iconic 4-minute YouTube clip shows Daly City skater Mike Carroll sailing over benches and cobblestones, coasting through parking structures, and grinding the nose of his board along a concrete step — until he finally falls.

“Oh my God, it was amazing,” 43-year-old Marina-born skater Scott Thompson remembers. “At that time, people might not have liked skateboarding,” he says, “but they didn't know what to do about it.”

Even before its waterfront architecture was immortalized in videos, San Francisco had already established itself as a subject of skateboard lore. It was the home of Thrasher magazine, which launched in 1981 and became the periodical of note in the skateboard world. It was a land of switchback streets and hills and plazas that were reimagined as obstacle courses; Justin Herman was more commonly known as “EMB,” which served both as shorthand for “Embarcadero” and as an abbreviation for the local skate crew “Embarcadero's Most Blunted.” It was a land where skaters crested the hills of Lombard Street and rattled through the brick-paved gullies of North Beach, and where, in 1986, a teenager named Mark Gonzales sprang from a platform at the Embarcadero, soared over a formidable concrete gulf, and magically landed on a staircase below. (That gulf was thence rechristened “the Gonz Gap.”)

Gradually, though, San Francisco cops began encroaching on the various back alleys and benches where skateboarders plied their trade. In 1992, police parked a patrol car next to Justin Herman to ward skaters off, Thompson says. By 1994, a beat cop was hanging out there every day.

“We called him 'Officer Squirrel' because he'd try and ambush you,” Thompson says. “He was like the worst, awful, cliche-looking cop — this white ginger guy with a little mustache and glasses. Such an asshole. He took so much joy in taking our skateboards.”

Watson only has vague recollections of Officer Squirrel, but says he vividly remembers the day he got arrested for squabbling with a cop at the plaza. “He had me handcuffed to a bench with one hand, and I was telling him like it is in a teenage way, and the cop came over and popped me in the face,” Watson says. Another veteran skater, Ando Caulfield, remembers going to juvenile court to pay a raft of citations and retrieve 10 or so boards confiscated at EMB.

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As the exchanges got testier, skaters began migrating to other spots, such as a row of stairs with steep bannisters that connected the Embarcadero to the city's downtown corridor. Built as a pedestrian walkway, it became a hangout for homeless people, skaters, and bike messengers; according to Watson. The stairs' nickname, “Hubba Hideout,” originated from the crack that some vagrants would smoke there. “We called the rocks 'hubbas,'” he explains, adding that ''hubba” ultimately became skate-slang for any ledge that ran alongside a row of stairs.

Skaters also moved over to Pier 7, a low, two-step platform with squat benches, which lent itself to a grittier skating style. Since the obstacles weren't nearly as intricate, skaters focused on manual tricks like balancing on the nose or tail of the board, scraping their wheels along the ledges, and leaving scrub marks on the concrete. Then the police encroached on that spot, too, pushing the skaters to yet another part of the city — a pedestrian overpass at Third and Army streets, flanked by a Muni bus yard and a creek clotted with garbage and wood pilings. Thus far, it's the only place remote enough to stave off law enforcement, Thompson says.

Nonetheless, the cat-and-mouse game persisted, and skateboarders soon found themselves banished from anywhere the city was interested in filling with tourists or new development. They had little choice but to move. Skateboarding had been illegal since the 1970s, per an often-overlooked section of the municipal traffic code. But during the skateboard renaissance of the '90s, police began bullishly enforcing it. As San Francisco started transforming in the wake of the first dot-com boom, real estate developers conceived a new urban design that would keep skateboards out. Instead, they'd be shunted to fenced-in facilities that Watson compares to “reservations,” or to industrial zones on the periphery of the city. Those iconic spots that dotted the Embarcadero would quietly disappear.

Union Square, with its zig-zag bannisters, ridged granite steps, and strategically placed flower beds, is an artfully designed bulwark against skateboards. Most of these architectural features were introduced during a $25 million remodel in 2000, right at the end of the dot-com boom. Downtown merchants were coalescing to form business-improvement districts, which in turn would fund street-cleaning and landscape improvements; then-Mayor Willie Brown had a European vision for the city, with a piazza as its centerpiece.

That vision didn't include San Francisco's less-desirable elements. Rails in the middle of benches served the dual purpose of inhibiting skaters and preventing homeless people from lying there; wood installed on the seating area of Pier 7 constituted a similarly effective barrier. Cobblestones were laid on the band shell at Golden Gate Park, which was once a prime skate spot; metal edges were nailed to the concrete embankments of Embarcadero. The city screwed studs into the bannisters at Hubba Hideout and laid gravel at the ends of its staircases. In 2011, it ripped out the ledges.

To an increasing degree, San Francisco's animus toward skaters became embedded in its architecture.

Meanwhile, the ongoing spats between cops and skaters had become a political issue in City Hall. By 1997, skaters had formed their own political bloc, enlisting then-Supervisor Tom Ammiano to override the 1976 law banning skateboards from public roadways. That campaign ultimately failed, but it did pique the interest of Supervisor Gavin Newsom, who decided to create a citywide Skateboarding Task Force in 2002. The idea was to help city officials design new skate parks and push for legislative changes, in the hope that skaters, cops, and pedestrians could one day coexist peacefully.

In 2005, skaters and their City Hall allies managed to repeal a small section of the 1976 law that barred skateboards from Terra Vista Avenue; otherwise it remained largely intact. But then a 2007 charter amendment shifted transportation authority from the Board of Supervisors to the SFMTA, at which point seven years of task-forcing were essentially rendered moot. Now, it's illegal to ride a skateboard on any street or sidewalk within a business district, or on any residential sidewalk during the day. The last change, ratified in 2008, forbids skateboarding on MTA platforms.

But even as the city banished skaters from their former haunts, it spent millions to construct six skate parks in the past 14 years. Bryan Hornbeck, who heads the San Francisco Skateboarding Association (an offshoot of the aborted task force), sees these city-designated skate parks as the only solution to the cat-and-mouse game.

“My thing is that, if 8- or 9-year-old kids start skating in the parks, they're not going to be out on the street as much, they're not going to be accosted as much, they're not going to come across homeless people as much,” Hornbeck says. “These things are going to save lives.”

But even after he got the city on board, Hornbeck says he faced staunch opposition from homeowners who insist that the parks bring noise and graffiti into their neighborhoods. “They go to these city meetings and bitch and complain, and then I bitch and complain about their bitching and complaining,” he says. “And then the city has to overcome the bitching and complaining, so that's how they [decide] what gets done.”

The sound of polyurethane wheels grinding over concrete creates a stark, percussive harmony with the cars whooshing overhead at Duboce and Mission Streets on an otherwise quiet Sunday night. Two lone skaters are circling the ramps and pillars of SOMA West skate park, which opened on a patch of ground beneath Highway 101 in July. A large bowl in the center is dappled by headlights and the waxen beams of street lamps. Except for a couple of homeless guys leaning against the fence with a shopping cart, the adjacent streets are empty.

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This triangular parcel is one of several skate parks that San Francisco unveiled in an effort to pacify its thrasher subculture. The first, Crocker-Amazon Skate Park, opened in 2000. It was followed by Hilltop Skate Park in the Bayview (just a big cement dish, though it's slated for a remodel next year), Potrero del Sol in the Mission, Waller Street Skate Park in the Haight (a temporary installation that rankled neighbors), and Balboa Skate Park, which transformed a section of Mission Terrace parkland into a jigsaw puzzle of wood ramps and platforms. Each of these facilities is a multimillion-dollar olive branch from the city to its skaters, in the hope that they'll cause less trouble if they're kept inside a fence.

Many skateboarders embrace them; others are wary. To Watson, municipal parks strip away a key element of the '90s skate culture he remembers: that pack-hunter tradition of roaming the city in search of ledges, curbs, or scrapyards to commandeer. To city officials, they're a tool with which to domesticate an outlaw population.

To some nearby residents, they're a blight.

Wolfram Arnold helms the home owners association for a condo complex on Stevenson Street, just north of SOMA West. He says the sound of skateboard wheels rattling down the cobblestone street rousts his family at all hours of the night.

“The freeway, it's more of a 'whoosh,' just white noise,” he says. “But these skateboards hit the pavement and they sound like gunshots.” Not to mention that skaters pee on his front stoop and his garage, because SOMA West has no restrooms.

“We've just started calling the police,” Arnold says. “But they're annoyed because they have other things to do.”

He believes the axis of power has shifted in San Francisco: Skateboarders now have their own lobby at City Hall, and officials are so eager to pacify them that they'll overlook the concerns of business owners and residents. Cops don't issue tickets any more because they get thrown out in court.

It's a far cry from the days when Officer Squirrel besieged unsuspecting skaters by the Embarcadero. Yet Arnold also suggests that the new crop of skate parks has failed to resolve a long and acrimonious conflict.

Adding a motor might, in fact, be the only thing that shifts public perception.

Die-hard skaters like Thompson and Caulfield bristle when asked to opine on electric skateboards, and perhaps that's understandable. The new boards are, after all, intended for a more mainstream population. But they're also the end of an evolutionary line. Wood boards that were traditionally used for stunts led to longboards, which are really a form of suburban transit; their big wheels and long decks keep a rider from popping onto rails and grinding away at property. (In some cities, skateboard laws have exceptions for longboards, because they're not perceived as a bad element.) Those, in turn, begat the latest transformation, in which boards are converted into economical, ecologically friendly, self-powered vehicles.

In skateboarding, as in other things, cultural forces pivot in relation to technology. The sport was once dubbed a nuisance, and the city tried to push it out. Then it gained mainstream acceptance, and the city tried to make space for it. Now it's a viable form of transportation, and the city embraces it: Supervisor David Chiu tested one of the Boosted Boards in August, at a Hayes Valley neighborhood event sponsored by The Bold Italic. He rode wearing an immaculate suit and tie.

People who might revile the old wooden boards see these motorized things on the street and think, My, how far we've come.

Sanjay Dastoor had little interest in skateboarding before he helped conceive the idea for Boosted Boards with two other Stanford grad students in 2011. Co-founder Matt Tran had finished his master's degree in mechanical engineering and gone to work for Lockheed Martin; in his spare time Tran was trying to develop a “snowboard for the street” that operated as cleanly as a Segway electric two-wheeler, but didn't look as big and dorky. The other co-founder, John Ulmen, had purchased his first longboard during grad school. He used it to get around campus, but had a hard time pumping with one foot and balancing with the other while carrying all his things.

Dastoor was friends with both of them. He and Tran spent weekends snowboarding in Tahoe or riding motorcycles in the Palo Alto hills; after meeting Ulmen, they eagerly tackled his problem.

“We looked at everything that had a motor,” Dastoor says, adding that the team found electric and gas-powered skateboards dating back to the 1950s and '60s, though most were bulky things with monster wheels and lead acid batteries in their motors. They decided to refine the idea and improve the form, adding brushless motors (which are controlled by a computer instead of by mechanical brushes, making them lighter and more precise), jaunty orange wheels, and bamboo decks with grip tape. They worked on the first two prototypes at night and during weekends, using their savings to buy materials from a local hobby airplane store. Tran was still at Lockheed Martin; Dastoor and Ulmen were still pursuing Ph.D.s. They'd ride early iterations of the board around campus and through downtown Palo Alto.

“People would chase us and say they wanted one,” Dastoor recalls.

The following spring Boosted Boards was accepted to two startup incubators, Y Combinator in Mountain View and StartX at Stanford University. Dastoor and Ulmen decided to put their degrees on hold. They launched a Kickstarter campaign in the fall of 2012, with a video that showed young, preppy, flannel-shirted commuters hoisting the 4-pound boards onto their backpacks, sitting with them on Caltrain, and steering them up the steep hills of San Francisco or along the suburban boulevards of Palo Alto. They raised $467,167.

The idea was to serve a niche market of longboarders and tech junkies who fetishize elegant machinery. Carefully engineered, electric boards bear the same high-energy lithium-ion batteries that power smartphones, laptops, or electric vehicles. They're equipped with onboard sensors and processors. Their motors can glide up a hill at 20 mph. And, Dastoor says, they have the “dynamic” look and feel of a skateboard, because riders help steer by leaning from one side to the other.

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“Think of the way people are portrayed riding on a magic carpet in a Disney movie,” he says. And then, he adds, compare that to a mall cop riding a Segway — “not very cool.”

Not surprisingly, Boosted Boards earned gushing reviews from tech bloggers, and sold so well among the 25- to 35-year-old male population in Silicon Valley that the founders turned their Kickstarter setup into a bona fide cottage industry. (They now have a 10-worker assembly line, and an ever-expanding engineering team).

There are, of course, other iterations. In January, another Stanford engineer named Kyle Doerksen launched a Kickstarter campaign for Onewheel, a self-balancing, motorized board with a giant tire in the center. Its software algorithms allow riders to carve the pavement as though they're surfing a wave, Doerksen says in promotional videos. He's also based in Mountain View, where new board gadgetry is apparently a growth industry.

That's rattled people in the skateboarding scene, who, as Watson notes, have long been wary of “other wheeled activities.” Thompson views the new inventions as an affront.

“I was on Van Ness one morning, and I saw this guy coming up McAllister on one of those things,” he says. “And you know, I can just tell when someone looks uncomfortable on a skateboard. His legs were super spread apart, he had this really stiff stance. I was like, 'How do you go from like, not riding a skateboard, to riding an electric skateboard? You're out of your mind, man. You're gonna kill yourself.'”

He pauses bitterly. “You have to learn to ride around the block, pay your dues, then take it to the streets — like what kids do.”

It irks him that someone could bypass that learning curve with a piece of technology. And it suggests that a gritty street culture could ultimately be supplanted by something sleek, expensive, and new.

“When I saw that,” Thompson says, “it freaked me out, kind of.”

It gets weirder. In October, a husband-and-wife team from Los Altos launched a Kickstarter campaign to make their own line of hoverboards — like the floating decks that first appeared in 1989's Back to the Future Part II. Hendo Hoverboard inventors, Jill and Greg Henderson, built a prototype that flies an inch off the ground, owing to its deftly crafted magnetic levitation system. Their marketing pitch — tailored to the same audience of technology-obsessed pragmatists who made the Boosted Board so popular — promises “a vehicle with all the freedom of a car, and all the efficiency of a high-speed train.”

Within days of launching the campaign, they'd garnered $416,764 in donations, well over their $100,000 goal.

“It's definitely cool,” Boosted Board enthusiast Colin Sebern says, “but it's not in any way a competitor to Boosted.” To him, the difference is stark. Hendo is a toy. Boosted is a transportation solution.

Thompson is the owner of Mission Skateboards, a tiny storefront on 24th Street with graffitied votive candles and chipped skate decks in the display windows — one of them is decorated with old Muni bus transfers. The shop itself enshrines an older era of skateboard culture; Thompson is an unapologetic purist. At 43, he still can't cotton to the longboards that overtook suburban streets and college campuses in the early aughts (“It's a different customer — older white guys,” he says) and he can't envision ever piggybacking on the electric skateboard trend. When people call to ask if he carries Boosted Boards, he gets insulted.

Granted, his business is still chugging along, as are other shops, like FTC Skateboarding on Haight Street. Thrasher magazine still prints monthly issues from its headquarters in the Bayview, and there are at least as many wood skateboards along Market Street as electric versions. Despite the law, cops seem disinclined to stop them. Perhaps skateboards are thriving as a nostalgia-based trend. Perhaps they've lost their outlaw appeal, but remained viable as a form of smog-free transportation. And maybe the designer products from Silicon Valley helped facilitate that change.

What has deteriorated, though, is the once-sacred, resolutely uncivilized culture of skateboarding. Hubba Hideout is gone; skaters at the Embarcadero are now relegated to a small plaza in front of the ferry building. There's a security guard permanently on watch at Union Square, so the only time to skate there is between midnight and 5 a.m. (Longtime local skater Ando Caulfield says that despite the city's best efforts, Union Square remains “an amazing place for skateboarding.”) Skaters who once congregated at EMB are now drifting out to the avenues or into the Bayview. By the mid-aughts, they'd become the stuff of museum dioramas.

That's no overstatement. In 2004, Yerba Buena Center for the Arts mounted “Beautiful Losers,” an exhibit featuring street art that had once lived on the margins of society. It included an installation of hand-drawn skate decks by original Dogtown board designer Wes Humpston, and a 7-foot wooden bowl sculpture that looked like an empty swimming pool; museum curators invited local skaters in to give it a test run. Pianist Jason Moran tried a similar experiment when he appeared at the SFJAZZ Center last year, transforming his stage into a 36-by-20-foot half-pipe and enlisting 10 skateboarders to ride it while his quartet played in the background.

But that's what happens. San Francisco is abstractly interested in its skateboard history, but only to the extent that it can be distilled in an art exhibit, or circumscribed in a stage performance, or remembered in a wistful essay.

And, with the rise of electric boards, the skateboard follows so many other facets of San Francisco's culture into assimilation. It's a clean, efficient way to get around a city with its own powerful urge to go somewhere, even if it's not entirely clear where.

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