So you’re new to Toronto. It really doesn’t take long to realize just how overwhelming a city it can be; the people, the places and of course the sites. The last thing you want to worry about, in a rush or not, is getting to where you need to be in a hurry and having sufficient funds to cover the trip (If you’ve ever tried to hail down a cab during rush hour, you know EXACTLY what I’m talking about). Then the team at Winston, Inc. had an idea: “What if people could order, track it, and pay for their rides all from the comfort of their trusted iPhone?” Voila! Winston was conceived.

Now fast forward four grueling months of blood, sweat, and lack of sleep in a quaint King St. West loft, the App has finally hit Apple’s prestigious App Store; the team all glowing with excitement to show off their child to the world. TCG had the chance to sit down with Winston CEO Aidan Nulman to talk about the app, the service, and what really makes Winston the perfect suitor for Siri.

TCG: Why should the people of Toronto use Winston over the many many Taxi services available to them?

AN: What Winston stands for, at its core, is that transportation ought to be simple and comfortable. Right now, there are some good taxi services in the city, but most of them are neither simple to book nor are they a comfortable experience. The process is tedious and long and we are looking to make it as “magically invisible” as possible.

TCG: Do you think people will be swayed by the cost of the service? Money is tight for many right now….

AN: Absolutely. Winston isn’t positioned to everyone. We accept and relish the fact that we are a premium service geared towards people with disposable income. In an ideal world, we would serve everyone; as a start-up, however, we need to focus.

TCG: What are your plans to introduce Winston to Siri (when the service fully launches in Canada) and how do you think she will react to a male sidekick?

AN: First things first, due to my Jewish decent, I need to get her fathers blessing before we even approach; my parents raised me well. Assuming the first few dates go well, maybe things will get serious and allow a ring to become part of the picture. Until then, we are emailing Facebook everyday to get pokes back.

TCG: What do you see the future of Winston being?

AN: We see ourselves as two things: a global company AND a transportation company. If you don’t see us expanding along those lines in the next 6 months, we have simply failed.

TCG: What is the most luxurious car a user can expect to be picked up in?

AN: Our entire fleet right now consists of Lincoln Towncars, but we are also trying to mix in some sports cars to add a “wild side” to the service.

We’d like to thank Aidan and the whole Winston team for sitting down with us and spilling the goods on the newly launched service - we’re excited for what’s to come with it.

If you’re interested in giving it a whirl, you can download Winston for free from the App Store here.

You can also check out the website and learn more about Winston here