Why you should care

Because who likes looking for parking?

Spencer Richardson wants to spare you the aggravation of looking for a parking spot — and offer you the luxury of having your car delivered to you — with a startup he thinks will shape the very future of how we use cars to tool around our cities. But DropCar is not a ride-hailing app or a car-sharing platform or even a self-driving technology company. It’s tackling a set of more immediate, yet often more hidden, problems plaguing car owners worldwide: parking, maintenance, even personalized delivery — in short, “an entire support layer to the car that is missing today,” Richardson says.

The New York tech scene veteran started the venture in the car-clogged Big Apple. He plans to expand to a second city this year and has his near-term sights set on Chicago, Miami and San Francisco — three of America’s most infuriating metropolises for motorists. Since its 2015 launch, close to 10,000 New Yorkers have used the company’s services (leaving a long way to go: nearly half of the city’s 3 million households own a car). As garages struggle to charge enough to pay for premium real estate locations throughout the city — with many selling out to developers — DropCar caters to car owners with its team of valets deployed across six parking structures near the perimeter of the city, ready to deliver your car whenever you request it via the app. Fees start at $349 per month, cheaper than most garage memberships; for $15 an hour, you can hire a chauffeur to do pretty much anything you need, from waiting while you run errands to driving you to the airport to just moving your car across the street to satisfy New York’s maddening alternate-side parking rules.

Richardson doesn’t see automation as a threat, but as an opportunity for DropCar.

The on-demand valet parking idea isn’t new — West Coast darlings such as Luxe, Zirx and Carbon have been there and done that, but Carbon folded, Zirx ended its consumer-facing model and Luxe has “temporarily” suspended its services, all having learned the hard way that maintaining parking-on-demand services is incredibly labor- and capital-intensive. Richardson is hoping his entrepreneurial track record in New York City’s adolescent startup scene will help DropCar succeed where others have failed.

Richardson, 32, was born in Arizona and raised in Minnesota and California by his travel agent mother and tech inventor father. A New Yorker for 15 years, having first moved there to study at NYU’s Stern School of Business, he has long been driven by an entrepreneurial instinct. “I always had some business going,” he says, recalling a childhood lawn-mowing business and working with friends to run and then franchise a lemonade stand model.

Richardson’s first real startup, launched from a college dorm room, was a marketing platform to connect independent musicians and other content producers with fans. FanBridge grew to a database of more than 20 million fans — enough to land Richardson on Forbes’ “30 Under 30” list for the music industry in 2012, right alongside Rihanna and Taylor Swift. Tall and fit, wearing a tailored suit with no tie when we meet near Union Square, he’s every bit the confident CEO — now married to an Argentine he met on a business trip, and the father of two sons. Richardson left FanBridge after seven years to focus on DropCar full time.

Having successfully built out FanBridge, at a time when the city’s startup culture was in its infancy, Richardson is “one of the veterans of the [New York] space and pretty well known,” says fellow entrepreneur Sean Black, formerly of Trulia and now co-founder of home-selling platform Knock, as well as a prominent NYC angel investor. The city’s startup infrastructure has grown significantly in recent years, but it still lacks “the halo that San Francisco has,” says Black, referring to the ease of attracting investment and attention in Silicon Valley. In the case of DropCar, though, New York’s silver lining is that Richardson can “build a real business … without all the fuss” that attaches to some struggling Silicon Valley competitors, says Black, explaining that the New York startup culture places greater emphasis on revenue and avoids excessive hype that can fuel overambitious expansion plans.

For its part, DropCar has moved beyond the consumer-facing product to include a number of lucrative contracts with corporate clients. Whether it’s ferrying cars between auto dealerships, collecting and delivering cars for servicing, or partnering with housing associations to offer parking services to apartment building residents, Richardson points to supporting revenue streams as the crucial ingredient in the company’s long-term survival.

Even so, DropCar’s model has its critics. Providing a full range of services to car owners is “definitely a gap in the market,” says Adela Spulber, a transportation systems analyst at the Center for Automotive Research, but she spots two competing trends in the automotive industry that could be a drag on its success: a move toward alternative forms of transport, such as private shuttle services like San Francisco-based Chariot, and models for consumers looking for shared automotive resources instead of ownership, such as Zipcar and Uber. Spulber doesn’t believe any one of these trends will “win” outright; rather, each city or region will develop its own unique car culture — which means replicating a particular model outside of, say, New York isn’t a done deal.

And what about automation? Richardson sees it as less of a threat than as an opportunity for DropCar to be the company providing the software and infrastructural support that will bridge the gap between consumer and computer. After all, Google’s going to need somewhere to park its fleet of self-driving pods.

Tracy Moran contributed reporting.

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