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Startup: The HireWinston app makes scheduling cabs easier than ever

For some, inspiration comes from a random spark. For others, it comes from an inspiring environment. The latter was the case for Krista Caldwell when she was selected to join an experimental program in high school called Design 44. 

It was a bunch of designers and programmers and art students mashed together, says Krista. They gave us access to a decent amount of funding and gave us a period to build whatever we wanted for the whole year. It was the first time we had a super unstructured environment to create something. It was kind of scary at first, since in high school [you're usually told] what to do. But in the end, we created a really awesome magazine, one we never thought we could have done.

I think it inspired me, Krista added, because it showed me what we could do when we weren't told what to do. And we didn't need anyone to tell us to create something.

Now Krista, 21, is a forth year student at Quest University and the founder of HireWinston, a smartphone app that takes the headache out of hiring a cab. HireWinston, now on Blackberry and iOS, has been getting a hell of a lot of buzz. 

Krista's core team met while participating in The Next 36, a national entrepreneurship program. That's where they came up with the idea of building software that makes taking cabs and limos super simple. It lets you book a car for now or later from your smartphone with a couple of touches, says Krista. You then pay for the ride automatically and get an accurate record of the transaction that makes it much easier to expense a ride and for your employer to see exactly what the transaction is.

When planning out the marketing and sales strategy for HireWinston, Krista knew that for this app to succeed, it would need to serve a specific niche. At first, we wanted to build it for everyone who takes taxis. But we realized the people who have the biggest problem with taxis are professionals who take taxis every day. Lawyers and accountants, for example, who are in cabs all the time and are expected to expense all of their rides at the end of the month. It's a big hassle many professionals would love to avoid. 

Krista believes her focus sets her apart from her competitors. We know exactly who we're solving a problem for. And we're making all of our decisions for that person. So we listen to all of our customers, but when someone asks for a feature, we're always thinking about the consultant, the lawyer travelling to work. For example, we added a pre-scheduling feature which adds a little complexity on our end, but when someone's booking their airport flight for Monday morning, they don't want to wait twenty minutes before their taxi arrives.

But as all entrepreneurs know, starting a business doesn't come without its rough patches. There comes a time when you have to make the tough call. When we first got started, says Krista, we had this one idea that was a little different than what we're doing now. To go ahead with it, we had to make this decision: ÔÇÿDo we do this? Or do we not want to do this?' After we took a vote, we had a half-buy in from one person on our team. That's when we stepped back.

When everyone on your team isn't bought in to something, you really can't go forward. At a small company, everyone needs to be working and a hundred percent engaged. So we ended up stopping at that point and changing course, eventually ending up with HireWinston. It was a good lesson. I think really believing in your idea is unbelievably important. 

When asked what excites her most about being an entrepreneur, Krista lights up. I really like the challenge of it, and the creativity. In school, I was really interested in studying the public and the private interactions in making change. And I think governments, they can change things really slow, and they need lots of support, time, and research before they do something. But as an entrepreneur, I can see a change I want to make and just go ahead and do it.