Stephen Ost: [00:00:00] So, something I highly advise is stick to something, and just keep creating more and more value, and you'll start climbing the ladder naturally. 

Andy Molinsky: [00:00:12] Welcome to From the Dorm Room to the Board Room, a podcast where we provide insights, tips, and inspiration for college students and young professionals, so they can make a really successful transition from college life to the professional world and beyond. 

Andy Molinsky: [00:00:30] My name is Andy Molinsky, and I'm your host. I am also a Professor of Organizational Behavior and International Management at Brandeis University's International Business School, where we record and produce this podcast. 

Andy Molinsky: [00:00:50] Today's guest is Stephen Ost, who is the Vice President of Product at Paradox, where he leads the product development of their AI recruiting assistant named Olivia. You've got to check that out. Paradox works with enterprise and mid-market clients to transform their global talent acquisition and candidate experience. Steven got his BS in Computer Science at the University of Arizona, where he was recognized as a College Entrepreneur of the Year by Entrepreneur Magazine. And since then, he's built a bunch of really cool software companies with one leading to an acquisition. He holds two patents. And he's a really interesting guy, very successful guy. And I think people listening are going to really learn a lot from Stephen. So, thanks so much for being on the podcast. 

Stephen Ost: [00:01:39] Thanks so much, Andy. It's awesome to be here. 

Andy Molinsky: [00:01:42] Cool. So tell us about Paradox if—you know, as if you're describing it to someone who knows nothing about it. I've checked it out. It's really cool. But tell us about it. 

Stephen Ost: [00:01:52] Yeah, definitely. So, Paradox starts at the top of the recruiting funnel. So, we make an artificial intelligence recruiting assistant called Olivia, and she screens and captures candidates, auto schedules them for interviews when they're 

qualified for a certain job. She really automates the 80% of busy, repetitive work for recruiters to focus on more human one-to-one interaction. 

Andy Molinsky: [00:02:22] If I'm applying for a job, I would meet Olivia basically? 

Stephen Ost: [00:02:24] Similar, yeah. So, our customers, our clients are business. So, we sell business to business, and they put Olivia on their site, and throughout their recruiting process in order to engage with these candidates. So, they want everyone to have a personalized experience, and Olivia is there to give that to them. So, Olivia talks to those candidates while they're applying. 

Andy Molinsky: [00:02:47] And what does Olivia look like? I've seen her, but for someone- 

Stephen Ost: [00:02:51] Yeah. 

Andy Molinsky: [00:02:52] ... who doesn't know. 

Stephen Ost: [00:02:53] Yeah, definitely. So, she's based off of a real person. She's actually our CEO's wife. Her name's Olivia, and she's a real person. And we chose that name just because there are a few reasons, but you can't misspell it, it's a popular name right now, it's a great name for an AI. 

Andy Molinsky: [00:03:12] It's cool. I would encourage people to check it out. All right. So, let's rewind. You graduated college like five or six years ago, University of Arizona. Tell us about your college experience. What was it like being in college? How did you start to become interested in entrepreneurship? Sort of, give a—paint us a picture of your college experience. 

Stephen Ost: [00:03:31] Yeah, definitely. It's definitely an interesting one and different than most. So, it started similar. I went in to the University of Arizona undecided. I did not know what I wanted to do. I just went there because my friends went there, and I literally followed my friends. I took Intro to Engineering, I took Chemistry, I took Calculus. Nothing really excited me too much. My second semester in, I took Intro to Computer Science because I liked making websites on the side. And that, I got 99% in that class. It was the perfect fit for me. So, I found out that's the direction I wanted to go in my life is Computer Sciences, building software. 

Stephen Ost: [00:04:17] So, once I started that, I started to become aware. I'm really interested in startups and building. And at that time, I never did one. So, I started wondering, how can I come up with some kind of idea that I could start pursuing? So, I started to make a change in my life where everything I did, I started to wonder, is this a repetitive task? Is this something that happens over and over that there should be an easier way to do and something simple as between class, I was in college life. I was a freshman, sophomore? And my sophomore year is when I really started to come up with this idea, called UFree. I started texting all my friends or a bunch of my friends between classes saying like, "Hey, I have an hour. You want to hang out? You want to grab lunch real quick?" Like, "What are you doing now?" So, that kind of stuff. 

Stephen Ost: [00:05:11] And every day, occasionally, you know, friends' times would overlap, and we would hang out, but it was a process, and it happened over and over. So, I realized, you know, that's something that we can automate. So, I started a company called UFree to address that need, and I just started building it. My background in computer science allowed me to start building a prototype of it, started using that with friends. It started becoming pretty popular with my friend group. Basically, you open the app, and you see who is free to hang out with, and their distance. So, how close they are. So, you know you can hang out with them, and you could sync your school calendar to it. So, it worked out really, really well. And then, I started building an engineering team for it. I raised funding. We launched at two universities, University of Arizona and Arizona State University. And then, that gained a lot more interest. And then, eventually, it was acquired. 

Andy Molinsky: [00:06:02] And so, how did you raise funding for it? That must have been—I'm imagining you ever raised funding before. Am I right? 

Stephen Ost: [00:06:08] Correct, yeah. It was—all of this stuff was brand new. So, my background in Computer Science did not teach me any of the business. So, I had find out that kind of stuff elsewhere. So, I joined communities like Startup Tucson, which is a local startup community, and they educate you on funding. That's part of it and, also, how to build business. I joined Arizona Center for Innovation, which is out of the University of Arizona, where they gave me a bunch of business skills that I didn't get in school. So, I just went to lots of different networking and educational groups to get that experience. And then, when I started to get myself out there, I started pitching at different events. I started connecting with lots of members of the community. Then, it started gaining interest from investors. So, I met with several investors who were interested, and I finally went with one of them and his partner. 

Andy Molinsky: [00:07:05] So, this is a really interesting story. I imagine people—imagine people would love to do something like that, people listening to this podcast. And I, actually, want to rewind to the point earlier in college where you said you tried out a bunch of stuff, you came in undecided, you weren't sure what you wanted to do. You ended up sort of like falling into a Computer Science class, and you said that—you said something about how you like to build websites on the side, so it was a perfect fit. I just want to highlight that piece. So, were you—tell us about this hobby of yours because I think that's interesting. Sort of, basically, you—that was your—that was the fit, ultimately. That seemed to be the catalyst for all this. What was your hobby? 

Stephen Ost: [00:07:45] Yeah, definitely. So, my hobby, I really enjoyed building websites. I wasn't the best at it, but I did enjoy it, and I got better every time I did it. And I built a few sites for a few friends, few family members, and it just—it was really enjoyable for me. So, I figured, why not try that as Computer Science, as a Computer Science class, and see if that would be easy for me, if it would work out. 

Andy Molinsky: [00:08:14] And it sounds like it did. 

Stephen Ost: [00:08:16] Yeah. 

Andy Molinsky: [00:08:18] So, I know that UFree is not the only company that you started. It sounds like you got the entrepreneurship bug. What happened from there in terms of starting up other things? And also, what do you like about that experience? 

Stephen Ost: [00:08:38] From there—so, during UFree, towards towards the end of it, right before the acquisition, about a year before the acquisition, I started becoming more aware of what problems I see around me. One of them was when I went into a restaurant, I saw people taking a water cup, and dispensing soda with it. And I may have tried that before, not saying, but anyway, that seemed like a problem, and it seemed like something that should be able to be addressed. So, that's when I started The Cup. 

Stephen Ost: [00:09:12] So, The Cup is a hardware cup with an RFID tag and a QR code built into it that communicates to the soda dispensing machines such as Coca-Cola, Pepsi, those machines. And it talks back and forth, and lets the machine know if that cup was a soda cup or not, if it was purchased or not. So, therefore, it enables the soda to be dispensed or if not, just the water can be dispensed. So, I ended up pursuing that one. I met with one of the largest chain restaurants. That went a little bit farther. And then, Paradox came up. So, I kind of set that aside, but I did get a patent on that. So, that's protected. 

Stephen Ost: [00:09:58] So, another area that I saw a need was in the courthouse, the way you bring evidence into the courthouse. So, in most cases, pictures that you take, videos that you take, you can edit them. It's not really obvious that it's a real legit picture or a video. So, I was thinking, how can you essentially make the video evidence and the image evidence that you have admissible in court? So, I started a company called Witness. And what Witness did was it linked with the—we prototyped it. We beta tested with Tucson Police Department, and if it was a platform for the police, as well as an app, a consumer app for the public. So, the public, whenever they felt in danger, or anything like that, they open up this app, and they start streaming, and it streams right to the police through the admin port over there. And everything is recorded, and saved, and an evidence report is generated, and that is transferred to the courthouse if you ever need to do so. 

Andy Molinsky: [00:11:05] Yeah. So, it's really interesting as I hear this, and I've talked to a lot of people now for this podcast and, you know, a lot of people in my life. I don't know if I've ever met anyone who just seems to walk around, see problems that are in need of solving, create solutions that can be sort of compartmentalized into a business in a very neat little way, and kind of moves on to the next one. And it's very interesting how you do this. And I guess, I'm curious where this comes from because it sounds like you started your story by saying that you followed your friends to college, you didn't even know what you wanted to do. Where do you think this comes from? Because, you know, not everyone does what you're doing. 

Stephen Ost: [00:11:52] Yeah, that's a really good question. And I honestly don't know the best answer for that. I have a drive. I want to accomplish more than I could ever dream about. And everything I do is always more than I think I can accomplish. And then, once I accomplish that, I just try to push myself to the whole next level. So, literally, daily, weekly, I'm always thinking, what is the next level? What's the next thing I can accomplish that people think I would not be able to accomplish? 

Andy Molinsky: [00:12:22] And it sounds like Paradox was the next thing. And that's what you're doing now. So, tell us about Paradox. What—how did you figure out—how did you figure out Olivia? How did you—or even the system? How did you figure out that this was a problem in need of a solution? Tell us about the origins. 

Stephen Ost: [00:12:42] Definitely. So, after UFree, I joined a company called And at, I partnered with the founder there named Aaron Matos. And he was building this local job board, and it's already huge at that point. They were 15 years in. So, I joined to create the app. So, when I was there, I started prototyping. As well, he was in the recruiting industry for like 15 years or so. So, I was just brainstorming with him, and we kind of thought, "Why does it take so long for a candidate to apply to a job? Like why can't you just apply to a job through texting?" And that's how that idea started for Paradox is we wanted to figure out how we could accomplish a simple application process, and in that case, with an artificial intelligence named Olivia. 

Andy Molinsky: [00:13:42] And it seems to me that there's more to it than efficiency though because you could have created an efficient process that didn't have that personalized, you know, character of Olivia. How did that piece come about? Because I think that creates a different vibe, for sure, when you meet her. 

Stephen Ost: [00:14:02] Yeah, definitely. Her persona is huge. It's what keeps us in front of the market, leaving the competitors for sure. So, the persona, we really wanted to put a persona on it. It's just it's a unique process. When you speak to a human, you enjoy the conversation. It plays a different role in the application. It's completely different. We've seen insane results for it. The capture rate is very high. You're with a human process. You can ask questions, and we can answer them. We can have a dynamic conversation through the process. So, all around it, it automates the process, saves a lot of efficiencies, saves our clients a lot of money. It allows for a better candidate experience. 

Andy Molinsky: [00:14:52] Yeah. 

Stephen Ost: [00:14:53] So, yeah 

Andy Molinsky: [00:14:53] It sounds it. I actually enjoyed seeing it myself. Let's step back a little bit. So, you've brought us through your journey so far. And I imagine that you've got some perspective on, sort of, the college experience in some, you know, insights about college students entering the workforce. What misconceptions do you think college students have, sort of, transitioning into the real world? 

Stephen Ost: [00:15:24] Yeah, definitely. So, the thing I see most - and this is when I review, resumes, I really think about this one - a lot of candidates are hopping jobs these days. They start a job. They don't really like it. They hop to another. They don't really like it. They hop to another. They don't really like it. Sometimes, they hop for different reasons. So, maybe they get a 5K salary increase, and maybe they're hopping to increase their salary short term, and every hop increases your salary. However, it's really hard to progress, to climb up the ladder at a company, and get up to a high level 

management if you are hopping. The longer you're there, the more valuable you are at the company, the more people come to you for questions and advice, and just the more responsibility you get over time. So, something I highly advise is stick to something, and just keep creating more and more value, and you'll start climbing the ladder naturally. 

Andy Molinsky: [00:16:28] How do you create value? What would you say if someone said, you know, "I get it, but what do you mean creating value?" 

Stephen Ost: [00:16:37] Yeah. Different companies create value different ways. The same with employees. So, different employees create value in different ways. And to create value, you really need to have an impact on the organization. So, whether you're on the product team, you have to create sprint decks, you have to create product requirements to create value. If you're on sales, you have to generate sales leads. If you're on marketing, you have to figure out how to market the product, get more clicks. You know, that kind of stuff. So, it really—it highly depends on your position. 

Andy Molinsky: [00:17:12] I see. So, become indispensable, become a critical resource for a company, and you can't do that by hopping all around, in a sense. 

Stephen Ost: [00:17:21] Definitely, yeah. It's a lot harder to do when you hop around. 

Andy Molinsky: [00:17:26] Yeah. No, interesting. Now, how about from—you studied Computer Science in college. Was there anything else aside from just simple Computer Science—not simple but simply computer science skills themselves that has ended up being useful for your career? Because, in a sense, you're not just—you haven't just been doing Computer Science. You yourself said that you've been kind of building and running a business. Anything else from college end up being useful, maybe even that you didn't expect? 

Stephen Ost: [00:17:54] Yeah, definitely. So, when I started college, I did not expect to start a company. So, that just kind of came to me from my drive. And that is the greatest learning experience I've ever had in my life. That taught me everything I did not know from computer science because I had to figure it out, or it would fail. So, I figured out 

how to sell the product, how to market the product, how to build a team. I had a team of 19 interns at one point, like literally only school credit, not even paying. So, it was me with 20 student interns building this out at the University of Arizona. And it's just all those things add up, different educational experiences that you bring to your future employers or the future company you create. And it's honestly the reason why I'm where I'm at today, UFree. 

Andy Molinsky: [00:18:46] So, you didn't take—so, it wasn't—you didn't take a Marketing class or Business Management class, and use some of the theories you learned from that class. It was more, sort of, the experience of starting things up and learning from it. Is that what you're saying? 

Stephen Ost: [00:19:00] Correct. Exactly. Yeah. 

Andy Molinsky: [00:19:02] Interesting. So, we're nearing the end of our chat. Often, I'd like to ask a few, sort of, quick questions. You must—as a tech person, you must have some productivity tips, like some something that you—what's something that you do, or you use, an app, or whatever it might be, it could be even a routine you have to stay super productive. 

Stephen Ost: [00:19:25] Definitely. My calendar is fully booked every day. As a product person, I need to figure out how to build literally everything in our artificial intelligence system. And the best way for me to do that is I try to limit the length of our meetings. So, rather than having an hour meeting, I'll have a 30-minute meeting or a 15-minute meeting. Doing that allows for the team to be more efficient. They only bring up the things that are the highest priority and things that need to get done now. So, that's definitely a productive trick I've learned over time, shorten meetings and focus on the things that are most important. 

Andy Molinsky: [00:20:11] That's interesting. So, shorter meetings, more productive, more efficient. How about mentoring? Have you had some? It sounds like you did have some mentors in, sort of, the community as you started to learn about entrepreneurship. 

Can you say anything about the role of mentoring in, sort of, fast tracking your career so far? 

Stephen Ost: [00:20:30] Yeah. Thanks for bringing that up. Mentors are insanely important. So, starting UFree specifically, my first startup, I had probably a team of 10 mentors I could go to for different purposes. There was someone that I could go to, to figure out how to advertise at the [UA Bay] campus. There was someone I could go to, to learn how to raise funding. There was someone I could go to to figure out how to price the product. It's insanely important because this is the first time you're doing it, you don't have that knowledge, you don't have that experience, and you need to find it somewhere. And typically, it's found out elsewhere, not necessarily in your college courses. 

Andy Molinsky: [00:21:10] And how do you find a mentor? I mean, you don't Google "find a mentor." Like, how do you do that? 

Stephen Ost: [00:21:19] Yeah. So, every university will have a startup community. There's always people trying to build startups on campus and get connected with those. There's also a bunch of coworking spaces around. So, if you're out of college, that's a great place to meet other entrepreneurs and see what they're doing. And typically, they are mentors. You can use them as mentors that they've done it before, or they'll know people that they could introduce you to. So, it's really about networking and knowing where to network. 

Andy Molinsky: [00:21:51] So, I guess, one last question I have for you is, if you could, sort of, go back in time to that version of yourself that was following your friends to college, and it sounds like you've ended up in a pretty cool place, that was about, what, eight years ago or so, is there any advice that, sort of, the current you would give to that previous you in terms of like life lessons, in terms of what to do in college, how to take advantage of your experience? 

Stephen Ost: [00:22:23] Definitely. I would suggest taking as many risks as possible. A balance is needed, of course. But in college, you're pretty much in a safe zone on a 

campus. You could take those risks. You can create a startup, and fail, and get an insanely amazing educational experience that will help you forever. You can join a startup and learn similar type of experiences. You could do projects on the side. It's really important to take those risks while you can. And college is definitely the safest place to take those risks from what I found. 

Andy Molinsky: [00:22:58] And what do you mean by safe? Can you just articulate that? 

Stephen Ost: [00:23:02] Safe, yeah. So, if you tried something, and you fail, you can always try something else. You're not restricted by where you're going to live or family. You typically don't have a family at that time. There's always people around you to help. So, if you do fail, you can get up and talk to a breadth of amount of people to get some support. It's really a great place to create your career, at least, the seed of it. 

Andy Molinsky: [00:23:34] I imagine also, and I would be curious to hear you think about this, it just occurs to me as you're talking that, you know, by and large, college is a learning environment; whereas the "real world" is more of a performance environment. Is that kind of what you mean by safe too that it's a learning center? 

Stephen Ost: [00:23:51] Definitely. Yes, definitely. 

Andy Molinsky: [00:23:54] Yeah, interesting. All right. Well, your story has been really interesting to hear. And I know it's even just really at the beginning. So, maybe if this podcast continues for another six years, we'll have you back. 

Stephen Ost: [00:24:08] Yeah, that would be great. 

Andy Molinsky: [00:24:09] But until then, thank you so much for coming on. And if people want to learn more about you or your company, where can they go? 

Stephen Ost: [00:24:17] Yeah, you could learn about me at You could learn about our company at You could find my contact information over there as well. And feel free to reach out, I'm always here to help. 

Andy Molinsky: [00:24:31] All right. We'll have that information on the show notes as well. Thank you so much, Stephen, for joining us. 

Stephen Ost: [00:24:35] Thank you. 

Andy Molinsky: [00:24:38] Thank you for listening to From the Dorm Room to the Board Room. If you're interested in learning more about the work that I do in helping people step outside their comfort zones and transition successfully into the professional world, please visit my website, That's A-N-D-Y-M-O-L-I-N-S-K-Y dot com. And also feel free to email me directly at with any feedback or ideas for guests for future podcasts. 

Andy Molinsky: [00:25:09] This podcast is brought to you by Brandeis University's International Business School. By teaching rigorous business, finance and economics, connecting students to best practices, and immersing them in international experiences, Brandeis International Business School prepares exceptional individuals from around the globe to become principled professionals in companies and public institutions worldwide. Thank you so much for listening.