Brandeis International Business School

036: Looking For Problems & Finding Solutions

Stephen Ost is the vice president of product at Paradox, where he leads the product development for their AI recruiting assistant named Olivia. Paradox works with enterprise and mid-market clients to transform their global talent acquisition and candidate experience. Steven got his bachelor degree in Computer Science at the University of Arizona, where he was recognized as a College Entrepreneur of the Year by Entrepreneur Magazine.

While at college, Stephen developed an interest in startups and began looking around his world for problems that needed solving. This led to multiple apps and businesses, two patents, and one company acquisition. All of this from asking bigger questions and looking for the next level.

From the Dorm Room

Stephen went in to the University of Arizona undecided, with no idea of what he was going to do. He was just following some of his friends. He took intro to engineering, chemistry and calculus classes, experimenting in all sorts of subjects, but nothing really excited him. In his second semester, he took intro to computer ccience because he liked making websites on the side. It was the perfect fit. That's the direction he wanted to go in life: computer sciences, building software.

Once he started down that path, he became really interested in startups and building businesses. He started wondering, “How can I come up with some kind of idea that I could start pursuing?” He started to look at everything he did through this lens, asking “Is this a repetitive task? Is this something that happens over and over that there should be an easier way to do?”

During his sophomore year Stephen came up with an idea called Ufree. He was texting his friends between classes asking, "You want to hang out? You want to grab lunch real quick?" Occasionally, their free time would overlap and they would hang out, but it was a process that happened again and again. He realized, that's something that we can automate, and he created a company called Ufree to address that problem.

Stephen’s background in computer science allowed him to quickly build a prototype and start using that with friends. It became pretty popular with his friend group. The app would sync with your school schedule, and show you who of your friends were available and how close they were. At a glance, in seconds, you could see who had free time to spend between classes.

As its popularity grew, Stephen started building an engineering team for the platform, raised funding and then launched the app at two more universities, University of Arizona and Arizona State University. That led to a rapid growth of interest, and eventually, acquisition.

To the Boardroom

Raising funding was entirely brand new to Stephen. His background in computer science did not teach him about the business side of things. He joined communities like Startup Tucson, a local startup community, and the Arizona Center for Innovation out of the University of Arizona, where he gained many business skills that he didn't get in school.

He started pitching at different events, connecting with members of the community. Then, he started gaining interest from investors. He met with several investors who were interested, and he finally went with one.

But UFree was not the end of his entrepreneurial journey — he had caught the entrepreneurship bug. About a year before the acquisition, Stephen started becoming more aware of the problems around him.

One problem he noticed was, in restaurants, people would ask for a free water cup, and they would fill it with soda that they didn’t pay for. Sneaky! This seemed like a problem for the restaurants, and one that would be solvable, so Stephen started work on The Cup.

The Cup is a hardware cup with an RFID tag and a QR code built into it that communicates with the soda dispensing machines. It lets the machine know if that cup was a soda cup or not, and whether or not it was purchased. He met with one of the largest chain restaurants, but before he could pursue it further, Paradox came up. He set it aside, but before that, he did manage to get a patent.

After Ufree, Stephen joined a company called He partnered with the founder there named Aaron Matos to create the app. He started brainstorming with Aaron, and they wondered, "Why does it take so long for a candidate to apply for a job? Why can't you just apply for a job through texting?" That was how the idea for Paradox started: they wanted to figure out how to accomplish a simple application process, and in that case, with an artificial intelligence named Olivia.

The common thread through all of these companies and ventures is simply looking at the world, identifying problems, and asking how you can solve them. This process led Stephen through all of his pursuits to where he is now.

The Entrepreneurial Edge

Every week, we highlight one piece of advice for aspiring, struggling and successful-but-want-to-be-even-more-successful entrepreneurs:

Mentors are incredibly important. The first time you're doing something, you won’t have the knowledge and experience necessary to move forward and you need to find it somewhere. And typically, you have to seek it out. It won’t necessarily be in your college courses.

Every university will have a startup community. There's always people trying to build startups on campus, so learn to connect with those. If you’re out of college, you can also spend time at coworking spaces to meet other entrepreneurs and see what they're doing. And these people can become your mentors, or they'll know people that they could introduce you to. Don’t underestimate the importance of networking.


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