Winston, a locally developed smart phone app, plans to change the way Torontonians (and hopefully New Yorkers) hire cars

A small Toronto-based team of entrepreneurs is planning to go global with Winston, a new smart phone app that aims to transform the “archaic end-to-end taxi experience.” The application and a fleet of 20 Winston cars launched in the city on Monday, and we asked CEO Aidan Nulman to fill us in on his future plans and how the venture has gone so far. He said the big draw of the system is total convenience—with the press of a button, a Winston car is dispatched to the user’s location, pinpointed via GPS. In the same way, the user can track their car’s approach, which means at least the user will actually know its coming. Once the passenger gets in, the app keeps a record of the distance travelled and automatically bills the user’s credit card upon arrival.

So far the iPhone app has been downloaded 170 times since Monday, and a BlackBerry version is slated for early December (an Android app is expected to come later). Only 10 to 20 people have actually used the service since its launch, and Winston’s team of four has been contacting most of them for feedback. “One of the findings of the last few days is that the fleet needs to be bigger and offer better coverage,” said Nulman. Some padding may come from Toronto taxi and limo companies, which, according to the fresh-faced CEO, are interested in working Winston into their operations. Winston is also inking deals with four large businesses in Toronto and is in talks with five more (most are, appropriately, awaiting the BlackBerry release). The appeal for them is the electronic receipt system, which quickly and clearly indicates who took what ride and when. Three mid- to high-priced restaurants are signing on—a $5 discount card comes with the bill, suggesting Winston as a safe and easy ride home. “Most of them are overjoyed,” said Nulman, “because this offers them a way to service customers from when they walk in the door to the ride home.”

The company is nothing if not ambitious: without waiting for success at home, Winston is scheduled to expand into New York, Chicago, Los Angeles and San Francisco by year’s end, and in multiple markets in Europe and Asia in 2012. These will be limited launches, with fewer cars, and may come without auto-payment or tracking capabilities at first. Nulman hopes their international presence will appeal to travelling Torontonians, saying, “If they can trust Winston at home, they can trust Winston everywhere.”