That was the problem in the 1990s. In the early days of the Internet, dozens of startups tried to sell new cars online, only to find that the marketplace wasn't mature enough for the task and that state franchise laws restricted their options.
A few of these startups survived, including Autobytel.com and CarsDirect.com, but by selling leads to dealerships instead of selling cars to customers.
Even the most successful car-shopping startup of the 2000s, TrueCar, has struggled to regain its footing since 2012, when disgruntled dealers ditched the service in droves, claiming TrueCar eroded transaction prices and margins. The company lost $65 million on $260 million in revenue in 2015 as founder Scott Painter stepped aside as CEO and AutoNation Inc., investing heavily in its own digital storefronts, stopped buying TrueCar's leads.
Roadster's strategy is different: to be a 21st-century broker.
Since the early days of the automobile, when entrepreneurs such as Henry Ford wooed wealthy families with the promise of a vehicle better than a horse-drawn carriage, there have been brokers like Christopher Gross.
Gross, a corporate finance veteran with an MBA from Harvard Business School, ran a company called BuySide Auto in San Francisco's posh Pacific Heights neighborhood, home to much of the city's political and business elite. Nancy Pelosi, the longtime Democratic leader of the U.S. House of Representatives, has a red brick mansion there. Larry Ellison, co-founder of Oracle Corp. and the third-richest man in America with a net worth of $47.5 billion, lives nearby on a block called Billionaires' Row.
His customers, mostly well-off professionals with more money than time, would pick out a car, and Gross would do the work. He would scan dealer inventories, run the numbers on a loan or a lease, and use his dealer contacts to get a good deal. Customers would pick up the car in Pacific Heights, or pay extra for delivery.
It was e-commerce without a website: You ordered a car from your house, and it showed up there, as if by magic. Gross was selling 25 cars a month and charging up to $795 for each car he sold -- a "great little one-man business," he said.
Yet the success of the business relied on Gross' finance skills, and his relationships with dealerships. It relied on his knack for reassuring his customers, many of them friends and friends of friends, who were worried about getting the best deal.
"It doesn't scale well," Gross says. "It's a very high-touch business."
At the end of 2014, Gross tried something new. He sold his business to Roadster, which set off on a mission: to turn Christopher Gross into a product.
Since then, Roadster has aggregated dealer inventories across California, refined its pricing methods by collecting data from third-party sites such as Kelley Blue Book and developed a way for customers to find a car with an exact set of features.
Roadster charges a $295 flat fee for a service called Concierge offered only in the Bay Area. It's a digital broker business -- behind the Web page, there are people like Gross making calls and making the deal happen.
"That is not the business we want to be in," Gross says. "That's the business I wanted to be in [with BuySide Auto]. But that's not the business where you're going to grow and do transactions across the country at a rate of thousands a week."
Laws for brokers vary from state to state, which could slow or impede the spread of Roadster's business model. California, for instance, requires brokers to be licensed, to have a physical place of business and to make delivery through a licensed dealership, says Brian Maas, president of the California New Car Dealers Association.