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A podcast Series With Chet Kapoor

Season 2 · Episode 7

Keep your Finger on the Pulse: Problem-Solving & Podcasting with Global CIO of iHeartMedia

Steve Mills, Global CIO at iHeartMedia, discusses the importance of cross-collaboration, how software helps broaden employees’ bandwidth for creativity, and why you should build a strong network early in your career. He also reveals the key element that all the best podcasts have in common.


Published April 27th, 2021  |  14:46 Runtime

Episode Guest

Steve Mills

Steve Mills

Global CIO at iHeartMedia

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Episode Transcript

Narrator: Inspired Execution is a podcast featuring tech leaders from some of the world's largest enterprises and fastest-growing startups. Hosted by DataStax Chairman and CEO Chet Kapoor, each episode follows a leader's journey to scaling a massive business while inspiring their teams. Join us to learn about the experiences that have shaped them, challenges they've overcome, and the advice they'd give to their younger selves.

Narrator: Steve Mills, Global CIO at iHeartMedia, has over three decades of experience in IT, enterprise systems and software engineering. From building his first tic-tac-toe computer game in middle school to constructing complex systems in the defense industry, Steve is a master programmer and problem-solver. In this episode, you’ll learn about the importance of cross-collaboration, how software helps broaden employees’ bandwidth for creativity, and why you should build a strong network early in your career. Steve also reveals the key element that all the best podcasts have in common.

Chet: Steve, welcome to the podcast. It is so great to have you here.

Steve: It's great to be here, Chet. I appreciate your hosting me.

Chet: So you've been at iHeartMedia for over five years, but you've also worked in many different industries and had different roles– Motorola, T-Mobile, Rackspace. Tell us a little bit about your journey.

Steve: Sure. I was always interested in technology, really for as long as I can remember. I actually built a tic-tac-toe computer for a science fair project when I was back in middle school. It just always interested me. But I kind of stumbled into computer science as a major in college. I started out in accounting. I had a friend that was majoring in accounting and he sort of talked me into it. But I was good at programming. And, in the end, it's just puzzles. It's problem solving, and I was pretty good at it. And so that's what I majored in, like I said, kind of accidentally. And then found myself in defense. I had another friend that was majoring in computer science that went into the defense industry and talked to me into joining there as well. And it was a great place to start.

Steve: I did defense for about 10 years and they really taught me to be an engineer. They taught me to think through things systematically. We built really big systems that took a long time. And so everything ran on an overhead projector before anybody wrote a lot of code. And so I learned that systematic engineering discipline, it was a really good fit for my personality. But what I turned out to be good at was fire-fighting and project management and those sorts of not pure programming type activities. And so I really didn't write code for very long. I got sort of pulled into project and program management.

Steve: At one point, we bought a startup, I guess about eight years into my tenure at what's now Raytheon Systems. We bought a startup. That was just electrifying to me. I was part of the team that did that acquisition, and I liked it so much that I went and did a series of them. None of them crazily successful, but I saw a lot of different things. I went through all the sort of birthing pains that you go through in “small-company world,” where everybody washes the dishes, that kind of thing. So great learning experience.

Steve: And then the dot-com crash happened, and I landed at BearingPoint, in a project called TexasOnline, which was the e-government portal for the State of Texas. And that was really my first exposure to web-scale in any form, but really web-scale e-commerce. And that helped me a lot later on, when I landed at Motorola. And I went from there to T-Mobile. I got my first taste of real, big, corporate IT, which is messy and painful, but you get to solve real problems and you get to see the results up-close. And that really appealed to me. I liked that part of the job.

Steve: From there, my first CIO job was at Rackspace, down in San Antonio. I learned a ton there, as well, about how to do that job and how to not do that job, sort of in baptism-by-fire mode. I was there for CIO, it was my first CIO job. And I will tell you, the job is a lot different than it looks from one level down. It's a really different kind of job, but challenging and a ton of fun. I went from Rackspace to CIO jobs at Motorola, and then landed in my current role at iHeart, as you said, a little over five years ago.

Chet: You know, it is so interesting, Steve, that so many of our careers have started because of games: Tic-tac-toe, Tetris, Space Invaders. I know I'm dating ourselves, but it just seems like it starts from something as simple as a game.

Steve: Yeah. That's very true.

Chet: One of the things that's interesting about this transition of becoming a CIO at Rackspace and then subsequently being a CIO at Motorola, at iHeartMedia. Do you feel like you are now working on things that take you away from being the technical self that you used to be?

Steve: To some extent, yes. The real difference that I saw when I moved from executive leadership in IT, a VP-level position, to CIO is your focus really has to shift from downward-looking execution to looking across the business. And it's critical, if you're going to be a successful CIO, that you really know how the business works. You really have to go around to the other side of the table and sit beside your business partners and look at their problems. Because a lot of times they don't know they need IT help early enough for you to really be involved in the planning and make a big difference. And so you kind of have to look through their eyes at the business and at their problem set and understand how they're getting measured and what's important to them. And then map that back on the technology. So that's a big part of the job

Steve: But I make it a point to keep my hands in the details of at least one or two projects that are going on, both because I enjoy it–I really like the tech side–but also because it's a really good way to keep your finger on the pulse of what's happening at the front lines, how people are working together, and how effective we are. So I mix it up, but definitely there is more pull toward the business side. I wouldn't really describe the CIO role as a technical role.

Chet: Everybody finds their own way of being involved in projects, right, and making sure they get into the architecture and get into what the future looks like. I think not losing the geeky side of it is really important. Otherwise, you just lose your grounding, you just lose your bearings. Is that fair?

Steve: That is fair. And I try to do some outside things, as well, to sort of keep that part of my tool-set sharp. I participate in several different venture capital, advisory-board type things. And at least a couple of times a year, I sit down with my direct report team and one or two folks from the VC community and just look at portfolios, look at trends, and sort of pick their brains around where they see technology headed and what's at the point of the spear.

Chet: iHeartMedia has gone through many periods of change since you joined, including what's happened over the last year. Tell us a little bit about how you have adjusted, and then, how do you keep your teams motivated and energized through these transitions?

Steve: I have a belief, as I look at technology and the evolution of technology, that low-value, repetitive tasks are eventually going to be done by software. I try to take the lead on finding those and applying AI, data science, machine learning, to do the things that are tedious and the areas where humans tend to make the most mistakes. I read a study back in the nineties, I think, that showed that a team of touch typists mistyped something like 1 in 26 characters. So, you know if the professionals are doing that, then average employees are probably making more mistakes than that. And software doesn't make mistakes unless it's got bugs in it, generally speaking. So I think that's a good thing to do for the company. And it's inevitable. If you don't do it to yourself then someone does it to you. But I think it also frees up our most creative people to be more effective. Software is a real bandwidth amplifier. And so that's probably one of the biggest drivers of change at iHeart in my time here.

Steve: In terms of the team and how to keep folks engaged, that's not as hard as you might think. We're in a really interesting industry. I haven't worked in media and entertainment before, but music is sort of in our DNA, and it's an exciting place to be. I think the types of people that are drawn to IT roles at iHeart, and that tend to come here and stay and prosper, are folks that like to make a difference on the business side. And so the change is part of what they do. It's something that they enjoy and that energizes them, or they probably wouldn't be here. And so it's actually really a cool thing for them to see the effects of the projects that we execute and the way that it's transforming the business, because almost everything that's changing at iHeart in the last five years while I've been here has been fueled by technology in some form.

Chet: Is it part of your selection criteria as people come in? Do you look for their passion in your business, or is it just that you attract people who are passionate about your business?

Steve: I think it's a mix, and we're not really a technology company. I mean, we apply a lot of technology. But if you match us up against a Google or an Amazon, we're not really a tech company in that way. And so people that would be really happy as a Google engineer might not be as happy here. And I try to shake that out of them during the interview process and make sure that they understand what they're getting into because it's a great place to work, but it's IT, and it is a little bit of a dirty, messy process. Business processes are never simple.

Steve: And one of the things that I think is sort of true in the product world, obviously depending on what types of products, but you kind build things in a certain way in isolation. And with IT, nothing's ever that way. Anything you do depends upon a bunch of other things and connects to a bunch of other things. That's part of the fun and the challenge: the orchestration and that sort of an environment. But you either sort of like that stuff or you don't. We've had people come here, joined us, they interviewed well, everything looked great. And then they wound up self-selecting out or being selected out because they just weren't a fit. And it wasn't a thing that was exciting to them. And that's fine.

Chet: My take is that you have to be passionate about the mission. Because, as you know through your experiences, somebody who's passionate about the business is far more productive than somebody who just thinks of it as a job.

Steve: I think that's right. Especially at iHeart, one of the really exciting things for me about the job is to see the impact that we have on the way people work. Radio is an industry that hasn't really changed very much in the last 30 or 40 years, but it is changing now. And I think it's a little bit of a forced march, in a certain way, toward digital. But it's really rewarding to me to be able to take pain out of the ecosystem, and to free up wasted time so that people can be more effective and focus on things that matter.

Chet: So you're in entertainment now. You've got a lot of experience in podcasts. What makes for great entertainment?

Steve: Well, I'll give you my personal perspective, because I'm sort of a podcast addict. That happened really after COVID hit. The best podcasting to me is storytelling. And I hope I don't date myself too much by mentioning Garrison Keillor, but I think he would probably tell you that storytelling is not a new idea. It's been around a while. But the idea that you can download it and carry it around with you is pretty powerful because you spend a lot of your day doing things that don't really allow you to look at a screen, and podcasting slots right into that. And so I find myself doing a lot of it.

Steve: I started with Dan Carlin's Hardcore History. I forget which episodes, but the ones about World War I were just astonishing to me. I had never listened to anything like that. Both of my sons recommended that to me. So that was my first ones. Those episodes to me are like a really good book. They're hard to put down. And it's the storytelling element that really draws me. My favorite podcasters are the ones that can get me excited about something I didn't think I cared about before I listened to them. Their enthusiasm is really contagious.

Chet: My perspective–obviously the storytelling piece is really important–but the one thing that's consistent across all the podcasts we've done with Inspired Execution is the passion by which people talk about diversity, education, leadership, or technology. That makes a massive difference. I love your point.

Chet: Who inspires you?

Steve: Well, I hope this won't sound too corny, but I'm really inspired by stories of people that put others ahead of themselves and their own well-being. And in the moment, what pops into my head is healthcare workers. I was thinking about this, actually, last night, and what it's been like for those folks in COVID times–especially at the beginning, where they were walking into a situation that nobody knew anything about. But they showed up every day, and it's a good thing they did, because otherwise we'd have been in real trouble. It gives me perspective on my job, which is not nearly as hard as that.

Chet: What advice would you give a younger version of yourself?

Steve: I would say, build a strong network early. That's something I didn't really understand or think much about coming out of college, but I would advise my younger self to collect smart people as you run across them and stay in touch with those folks. I was probably 10 years out of college before I started thinking about that. And it actually took getting laid off from a job to make me realize what a big gap I had on the network front. And that's a bad time to find out. As I look back, I think I've had 13 jobs since I left college, and all but one of them came through people that I knew personally. And I can't count the number of times that I've turned to my network for advice or problem-solving help, or that sort of thing. It's just a really invaluable thing. And it's something that I think you have to put conscious thought into. You can't just let it happen.

Chet: Any specific tips and tricks on how one would go about doing it?

Steve: For me, it's generally as simple as when I see somebody or interact with somebody or work with somebody that I think is really smart–and not just smart, but collaborative, someone that I enjoy working with and that sort of thing–I just try to stay in touch. I go through in rotation and ping those folks every year or so, and just say, "How's it going? What's happening in your world?" And just try to keep the relationships going. If I'm traveling, I pay attention to who's in the city, try to catch dinner, and keep those relationships healthy.

Chet: That is awesome. Steve, this has been phenomenal. Thank you very much for your time. I'm sure our listeners will find this to be extremely useful.

Steve: My pleasure, Chet.

Narrator: Successful leaders know how their business operates from all perspectives. So make sure you take time to collaborate with your cross-functional partners and understand the challenges they’re facing. Steve also highlights the importance of adopting new technologies, like AI & ML, to give employees more bandwidth for creativity. Finally, never underestimate the power of networking, and remember to keep the lines of communication open as you progress through your career.

Narrator: Thank you so much for tuning in to today's episode of the Inspired Execution podcast, hosted by Chairman and CEO of DataStax, Chet Kapoor. We have many more guests and amazing stories to come, so stay tuned. If you haven't already done so, subscribe to the series to be notified when a new episode is released. And for Apple podcasts listeners, please rate and review the show to help give it a wider reach to listeners such as yourself. And feel free to drop us any questions or feedback at