You may remember a controversy a couple of months ago about MonkeyParking, an iPhone app that allows users to buy and sell street parking spaces. The concept was evidently too innovative even for San Francisco. The city attorney ordered the company to shut down on the grounds that auctioning public spaces is both dangerous and illegal.

Well, MonkeyParking is back. The company has made few tweaks to the app, and is almost ready to launch in a new city: Santa Monica.

CEO Paolo Dobrowolny is trying to make sure things go more smoothly this time, and has set up meetings with local regulators. But it doesn't look like Santa Monica officials like this idea much either.


“They do not have ownership of the space,” says Frank Ching, the city's parking administrator. “That's unlawful. That's immoral. It's no different from a street bum [who] stands on a space, waves someone in and asks for a tip.”

Harsh. But like any good entrepreneur, Dobrowolny isn't taking no for an answer.

“We want to be regulated, not banned,” he tells the Weekly. “The status quo of parking is so inadequate. Everyone complains about it. We thought it could be a benefit to the city and the citizens to try a different approach.”

Dobrowolny is from Rome, Italy. He has an engineering background, and worked for a while for a high-speed rail company. A couple of years ago, he and two friends began working on an app that would make it easier to find parking spaces.

The idea is that someone who's about to leave a parking spot can put that spot up for auction. Whoever bids the most wins the spot. The typical space sells for $5-7. MonkeyParking takes a 20 percent commission.

They started out in Rome, but eventually they decided it would work better in the U.S. In a bit of irony, they wanted to come here because parking is better regulated in the U.S. In Italy, Dobrowolny says, drivers might sooner park illegally and risk getting a ticket than pay for a legal space.

Dobrowolny arrived in San Francisco in January on a temporary visa. Within three months, he and his co-founders had launched a beta version of the app in the iTunes store. The company is self-financed, so they did not have a big marketing budget. In May, they began spending about $2 per day on Facebook ads targeting San Francisco.

The idea took off from there.

“It was generating a few users a day downloading the app,” Dobrowolny says. “There was also a big amount of people tweeting on Twitter their concerns about it. From the tweets, it went to the blogs, from blogs to online media, and from online media to nationwide newscasts.”

Within a month, about 10,000 people downloaded the app.

In some tweets, people were tagging the office of San Francisco City Attorney Dennis Herrera, and complaining that the app was illegal. On June 23, Herrera issued a cease-and-desist letter, threatening to fine the company $2,500 per transaction.

“Monkey Parking is facilitating and encouraging its users to enter unlawful agreements with each other, and misleading them into believing that their transactions are lawful,” Herrera wrote. “Also, Monkey Parking is facilitating and encouraging drivers to use cellphones and other wireless communication devices in a manner that distracts them, posing a safety hazard to the public and violating state laws that prohibit using cellphones and such other devices while driving.”

By that point, Dobrowolny had been forced to return to Italy to renew his visa, leaving him unable to meet in person with regulators to tell his side of the story.

“It was really frustrating to be in Rome,” he says. “One of the concerns was that Monkey Parking was a band of hackers from nowhere with fake identities.”

Worried about the fines, Dobrowolny quickly disabled the app in San Francisco. Since returning to the U.S., he has met with San Francisco officials to try to address some — if not all — of the concerns.

One of the worries is that people might use MonkeyParking as a part-time job, staking out and auctioning off one space after another. In response, the new version of the app limits users to one sale every six hours. Another issue is “spot-holding” — when a user camps out in a spot waiting for a sale. Dobrowolny plans to use the GPS system to prevent that behavior, while adding a “Monkey Reputation” system to flag malicious users.

Dobrowolny also wants to explore some sort of revenue-sharing model with local jurisdictions, to address the concerns about selling public spaces.

Meanwhile, MonkeyParking asked its users which city it should try next. L.A. was the second-highest vote-getter, so he decided to give it a shot. The system needs a critical mass of buyers and sellers to work, so Dobrowolny wants to start in a small geographic area where parking is difficult. He decided to focus on Santa Monica and Beverly Hills.

“L.A. is really wide and a big market, but if it's too spread, it's not gonna work,” he says. “Hollywood, maybe.”

Santa Monica is already home to ParkMe, an app that provides real-time information on parking garages, lots and some street spaces. Mark Braibanti, the marketing director at ParkMe, said that even if MonkeyParking navigates the legal hurdles, it could have trouble providing adequate supply.

“I love the concept but I think it's going to be really hard for them to penetrate any market,” Braibanti said. “They need to completely change the way people look for parking and then have enough customers logged in and updating the parking info to make the app usable.”

Since the controversy died down, Dobrowolny has taken meetings with venture capitalists who may yet want to invest. He said that the company will soon be looking to raise a seed round of financing.

But at some point, he's going to need some municipality to grant him permission to operate. So far, that hasn't happened. Even L.A. Mayor Eric Garcetti — a tech enthusiast — doesn't seem too jazzed about MonkeyParking.

“We do not support this kind of use of our public assets,” said Vicki Curry, a mayoral spokeswoman.

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