Jonathan Rivers, Fortune

Trac Bannon: 

I’m noticing a few core traits in the many guests I’ve hosted for the Real Technologist podcast. Authenticity and a willingness to say yes. This rings true for guest Jonathan Rivers. He was recommended to me as somebody who absolutely is passionate about making opportunities for others. 

Talking with each guest is filled with surprises and challenges my own preconceived notions. Jonathan Rivers is the CTO of Fortune Media which includes Fortune Magazine. In doing some research, I came across Jonathan’s headshot. Sometimes his photos show a mild smirk though often the photos have an intensity that you feel. This looks like the kind of person that you want on your side, especially when the chips are down.

Interestingly, my expectations for the Zoom call were that I would see an opulent executive office in a high rise overlooking a spectacular view. Perhaps with some modern art chandelier. What I encountered was an average guy in what looked to be like an average cube spot or office touchdown spot. The lighting was less than average, though it doesn’t really matter for audio. Over his shoulder was the only discernible decoration: a whiteboard with an architectural diagram scribbled in marker. 

He doesn’t smile often, though when he does, you feel a sense of satisfaction that he is human. I would not say that he’s a big old teddy bear like my close friend Bryan Finster. Instead, I would say that this is a super intense and intelligent human.

As we discussed his origin story, and going from a kid in Texas to the CTO of Fortune Media, we touched on myriad topics including his philosophy on diversity. I was very curious what I was going to hear from this white, middle aged biker dude. 

Jonathan Rivers: 

It’s incredibly near and dear to my heart. For so many reasons. One, I’m really proud of the team that I’ve built here at Fortune.

I built it with that in mind. And I’ll tell you why… One, ’cause it’s the right fucking thing to do. But more importantly , you look at this from a tech industry perspective, the moment that you establish a bro culture in tech, if you hire a bunch of white nerds out of suburbia that all wanna talk about Fortnite, you are sunk, right?

 If I hire me, me number two is gonna have all the same blind spots that I have.

And I want a team of really different people that see things from different backgrounds, that see problems from different angles, that want different things out of life. Frankly, they all behave better. Everybody behaves better when you’re in mixed company than when you do when you’re with your buddies.

 

Trac Bannon: 

You are listening to Real Technologists. I’m your host, Trac Bannon, coming to you from Camp Hill, Pennsylvania. Each week we choose a unique guest behind leading Edge Tech innovation to explore their genuine stories, their true journeys. Technology touches nearly every aspect of our lives. It’s being driven by diverse perspectives and experiences of real humans.

You’re in the right spot to hear about the real technologists reshaping our world. Stay tuned for stories that will give you something to noodle on.

This guy says what he thinks and is unapologetic. Like two other Texan natives that I know, Lani Rosalis and Bryan Finster, being authentic and stating your opinion and supporting it with clear logic seems to be a Texas trait.

Jonathan is Texas born and raised, growing up in Dallas, mostly in the suburbs, though he has lived much of his adult life on the east coast. Jonathan grew up as a chubby kid who was a bit of an outsider. Like many of us, when asked if we’d go back to high school, nearly everybody says, hell no! 

Jonathan Rivers: 

High school was not kind to me. I was a fat kid and a nerd and… you know, look… this is the late eighties, early nineties. like, being a nerd wasn’t cool back then. Right? You know, like now nerd chic is like the total thing and, back then it just wasn’t good.

I was never like, particularly popular or cool or any of that… so it was all fine, but I struggled in high school because of the education system dictating how you learn and, it was a lot of regurgitation of things.

Trac Bannon: 

Playing computer games and building computers was always interesting to Jonathan Rivers. Remember 1980s with a computer is not like it is today. You had to install hardware drivers to run a joystick, fiddle with the jumper settings when you installed the graphic cards. It was his dad who threw a challenge to Jonathan that acted as a catalyst moment. 

Jonathan Rivers: 

You know, back then you had to deal with memory management.

You really had to load drivers for a joystick, for a sound card, do all this. And I told my dad I wanted to play video games, and he was like, you will learn to program before I let you play a video game on that computer. And so I wrote a program in basic that flipped a coin 50 times.

He took that as sufficient diligence and went on from there. 

Trac Bannon: 

When he had issues with high school math, Jonathan’s Marine Corps recruiter stepped in, intervened, and they rescheduled him to take consumer math. During his junior year of high school, it was possible to enlist in the military at 17 years old on a deferment until high school graduation. His parents supported him enlisting in the Marines, a decision that he jokingly says was perhaps their worst decision ever for this alternate pather. This Texas boy shipped off to Marine Corps boot camp just seven days after walking across the high school graduation stage.

Jonathan Rivers: 

They were supportive because they all had the worst idea ever. It goes like this… they thought that taking a kid with problems, with authority and letting him join the Marine Corps was gonna straighten him out.

What it did is it made a kid with problems, with authority, tougher, stronger, and have even larger problems with authority. It went spectacularly well for all of us. Now, I will say I love my beloved core. If they called me to this very day, I would go serve again.

 I was not the world’s best Marine, but I love the core. I credit it with everything that I am and everything that I have accomplished. The military teaches you in hell in 13 weeks of bootcamp. You know, just the resilience, of that experience, let alone learning, leadership, organizational structures, frankly how to accomplish the mission, is invaluable.

 it’s kind of interesting when you think about where I am today. I barely graduated high school and I never went to college. I’m completely self-taught and you don’t necessarily hear that out of a lot of CTOs. 

Trac Bannon: 

He would stay in the Marine Corps for three years and it’s clear that non military folks don’t understand the military mindset. 

Jonathan Rivers: 

You don’t understand the experience, you don’t understand the mindset, we are all trained to run towards fire, right. We are taught and trained to run towards gunfire. 

Trac Bannon: 

Running towards live fire? Wow. Jonathan is right that I would never have thought about that difference. When I thanked him for his service, he was quick to add “Do you know people didn’t start saying that until 9-11?”

To be honest, I had never thought of it. And like most Americans, I am sincere in my appreciation. 

Jonathan Rivers: 

When I got out of the corps in the mid nineties, it was like… screw you warmonger. Right. There was still that hangover from Vietnam at the time.

Trac Bannon: 

We navigated his experience in the corps, and he shared that it is getting more and more difficult to attract people to the services. Most are impacted by having a bit of life of convenience and there being other paths to easier income. Easier than running towards live gunfire, so to speak. During our chat, Jonathan shared what seems to be his one and only regret, looking back at his entire career. It was during his entry testing at Marine Boot Camp. Those with the highest scores were given opportunities to go into certain training specialties.

Jonathan wanted to be an engineer, in his words, because, “I thought it meant I got to blow stuff up” 

Jonathan Rivers: 

I got to fix bulldozers and forklifts and cranes.

So it was like I was playing with giant Tonka toys. But there’s a fun story there about the sort of greatest opportunity that I missed. It’s funny how my career got to where it is, and I missed a shot by one point, and I always feel like this is the story of my life where I missed something by like one point. it was me and this other dude. And we both qualified for Signals, Intel and Eighth… and he scored one point higher than me, got first choice, took signals – intel.

Trac Bannon: 

When he was discharged in 1995, he went back to Texas. His first stop was his father’s house, though that did not last long. His father took him out for apartment hunting nearly immediately. Jonathan Rivers struggled. With a single day of discharge training and a few general statements about him needing to start paying his bills. He didn’t realize the oncoming stress of not being able to continue to be a mechanic. 

Jonathan Rivers: 

I had a tough time getting out and if I fault the US military for anything, they do a great job of teaching you how to be a Marine.

They do a very bad job of teaching you not or how not to be one. I couldn’t apply my trade in the Marine Corps… because you need $10,000 worth of tools to be a mechanic

Trac Bannon: 

He took on a string of different jobs, including being a bouncer at a bar. It was during this period of his life that he met his future wife, Kerri. He actually gushes when he talks about her. He considers himself lucky… lucky to meet her and to settle down with her. It’s clear that Kerri is as unique and insightful as Jonathan. 

Jonathan Rivers: 

And she said when we first dated, she was like, look, I’m not gonna tell you how to live your life, but I’m not gonna bail you outta jail.

So you go make your choices.

Trac Bannon: 

That naked honesty completely intertwined with her wanting what was best for Jonathan is her MO. While waiting tables in the mid 90s, Jonathan landed his first role in tech through a friend who was selling video games at a computer store. He interviewed and was hired to man the help desk phones for Compaq computers. That grew into a second job doing desktop support for a speech recognition company. This is where he learned telephone systems and hardware. Consider we are all just now in the 2020s really able to use speech to text. This was the late 1990s.

 It was his wife that would create the next stepping stone opportunity, drawing him to move to the East Coast. He ended up in consulting roles doing Y2K migrations, replacing all the networks at a large law firm. It was his work for the Loudoun County Schools and a 16 year old kid that would act as the next catalyst moment.

Jonathan Rivers: 

I got tired of the Windows world.when I was a consultant… you talk about these serendipitous moments, I was replacing all of the networks in the Loudoun County schools in the DC area. I met this 16 year old kid who was the network admin at this high school. And he was really into Linux. I was a Windows consultant at the time, he turned me on to Linux and it was something that I’d never seen before and it was just the most amazing operating system and how the operating system was decoupled from the desktop manager.

 I decided I wanted to go do Linux stuff for a living.

Trac Bannon: 

The next step was to take on the role of system administrator at a firm called Ad Juggler. This would be yet another Catalyst moment in the life of Jonathan Rivers. 

Jonathan Rivers: 

In 2003, I was at Ad Juggler, and I got fired. I was young and talented, very talented, and very egotistical, and very full of myself. I ended up getting fired and I deserved it. Absolutely deserved it. I go home and I look at my wife and I tell her I got fired. And she does something that no wife does ever. She looks at me and she goes… two things. One, you should go buy a motorcycle. You haven’t had one since we’ve been married, and I know that’s a huge part of your soul that is missing. Two, this is the opportunity for you to finally live your dream, go to Motorcycle Mechanics Institute and become a motorcycle mechanic. 

Trac Bannon: 

Together they moved to Phoenix where he spent a year getting his Harley factory certifications and then worked as a mechanic for a year. He was really living a fulfilling life when fate decided to throw yet another catalyst moment in his path. 

Jonathan Rivers: 

And then the fun thing happened. I was so fulfilled at a spiritual level where I would go in and ride motorcycles and fix motorcycles, but I was intellectually bankrupt because motorcycles are very good.

They don’t actually break… really what you do is change tires and oil. Right? And I was craving the intellectual challenge that technology got. And I called ad juggler… I called one of my friends who was there. And I said, look, I’m thinking about getting back in the game. Can I get a reference?

And he goes, we need you. Come back.

Trac Bannon: 

The corporation was in leadership shambles and the tech was falling apart. He parachuted in and went from fixing motorcycles one day to turning around and redesigning the entire software architecture of the platform.

 He eventually rose to the level of executive VP. Funny thing though, Jonathan was still side hustling as a motorcycle mechanic on the weekends. It gave him nourishment. 

Jonathan Rivers: 

So five days a week I’m running an ad serving startup doing software architecture, network engineering, all of this. And on Saturdays I put on my work shirt and I went and changed oil at the Harley deal shop.

Trac Bannon: 

Sometimes we call that a boomerang moment. Jonathan Rivers would stay with Ad Juggler for nearly 12 years through 2011. By late 2011, Jonathan would begin a somewhat predictable 2-3 year cycle that he describes as his late career trajectory.

His next stop was the influential Public Broadcasting System, PBS, in the role of senior director for web operations and customer support. 

Jonathan Rivers: 

I went to PBS where I had the opportunity to build out all of the cloud infrastructure forPBS. I gotta give mad props to Paula Kerger, the CEO of PBS. In 2012, she invested in digital and let the digital team build in isolation. We built a video portal that in 2012 that rivals what Max is today, right? We beat HBO to streaming video.

Trac Bannon: 

When asked, Jonathan initially said he really didn’t have any mentors. In his word choices and in his actions, he is driven to prove himself. Perhaps this dates back to his high school days.

 He has a full set of sleeves saying his next tattoo will say “may my enemies live long so they can see me progress”. 

In his own words, most of his career has been fueled by the doubters, the naysayers, and the number of friends that have turned on him or morphed to be enemies. 

His next series of career opportunities all manifested the same way. He would prove himself to a client or to a boss. During an honest conversation, he would give his insights and somehow a new opportunity would manifest. This is not a guy who went searching online for his next role. 

Each role would be more difficult and more complex a digital transformation. When the PBS vice president of digital got recruited to be the editor in chief of the prestigious Telegraph news organization in London, who did they call?

He and his wife would pick up and move to London to lead digital transformation at one of the most storied newspapers in the world. Jonathan Rivers would initially start as the Director of Service Delivery and Operations, though eventually he became the interim CTO through 2016. 

The job was the hardest and most grueling he had had up to that moment. He and Kerri tried to move back home, but the CTO at the time fell ill with a heart condition. 

Jonathan Rivers: 

They were in the middle of a $10 million replatforming of the website. You’re talking about seven different development teams working in a code base to do a full replatforming. And the CTO like out open heart surgery out for three to six months. They asked me if I would stay, so I finished that, launched their first e-commerce product.

Trac Bannon: 

Jonathan is consistently pulled by his relationships and network of humans. The alliances pull him forward. This is how he got to be CTO of 3 Pillar Group in 2016. Another 3 year role kicked off by his network of client relationships and C suite leaders.

Having tasted what it was like to be in the C suite, and knowing his time with the Telegraph was growing short, he stopped by to talk to the CEO of 3 Pillar. He had been their client in his roles at PBS and at the Telegraph. 

Jonathan Rivers: 

I have had immense success while being absolutely terrible at networking.

I now had an interim CTO job, right…

And I wanted to go into the C-suite. And I realized something at that moment that had not occurred to me… that probably everybody who wants to be a CTO should know those jobs are not posted on LinkedIn or monster.com.

I stopped to talk to the CEO and he and I were, were talking and he’s like… well, I kind of need a CTO. 

Trac Bannon: 

About three months in, his CEO called and asked how it was going, to which he replied, I just quit. Oh, to have been in the room to see the CEO’s face. The CEO asked him to come back and solve the real problems facing the company and Jonathan did. The thing about being a CTO at a professional services company is that you’re living vicariously through all of your teams and talking about what they did. When the next serendipity conversation took him to fortune, he saw the opportunity to create the right environment for people to build. This is where he sees his sweet spot. 

There actually is someone in Jonathan’s life he considers to be his mentor, Stephanie Michko Beale. She’s the former CTO and Executive VP of Charter Communications.

They met when he was still at 3 Pillar. The account between 3 Pillar and Charter Communications was essentially on autopilot with not much effort being put in. 

Jonathan Rivers: 

I got my ass kicked that day. It was bad. It was a customer that we had been taking for granted that account that’s been auto-renewing year after year.

They decide they’re gonna go up and do this big presentation about all the new capabilities that I’ve been building out for them.

 we go up and there’s this meeting, there are four or five people in there. And we do this presentation about, these are all these new capabilities that we’re deploying for our customers and all these great things that we can do… and we finish… and she looks at everybody and she’s like, I had no idea that you guys had those capabilities.

She looked at everybody and it’s like… uh, Could you all step out? I’d like to talk to Jonathan, please. 

Trac Bannon: 

She would go on to talk to him one on one on the importance and impact of relationship building. Through this catalyst moment, Stephanie would take on a prominent mentoring role for Jonathan, so much so that I was truly touched by him sharing some self reflection.

Jonathan Rivers: 

I sometimes when I’m being egotistical oryou know, I got in trouble for this before I joke that I’m either the smartest or most accomplished person in the room. And I realized when I was with her, I was neither. I could listen to her forever because I know that sooner or later, she’s gonna say something that sort of really inspires me. 

Trac Bannon: 

For a man who says he can’t network, he is natural and organic and is as non traditional in his tenacity as he has been throughout his remarkable career. There’s a certain loyalty and alliance that comes improving yourself. I got the feeling that if I truly proved myself to Jonathan Rivers, he would pick up the phone and call me. That said, he is very intense and I can imagine being my younger self and possibly being intimidated by his intensity. Or, perhaps I would have been inspired. 

Jonathan Rivers: 

The British would say, I’m Marmite, I’m a bit of an acquired taste. I have the sort of the good fortune to be charming enough to get away with some of the rough edges… right. I can be a little mean sometimes and I’m not always my highest self, but I go through life with great deal of integrity and sort of warmth and charm for those that I respect and I love.

Trac Bannon: 

It is that spunk, that same vin and vinegar that would land him his most recent role, the CTO of Fortune Media. He was attending a conference and was introduced to Fortune’s chief revenue officer and the chief publisher at the time. As fate would have it, Fortune was being sold out of Meredith and Time Inc. into the hands of a private investor. 

Jonathan Rivers: 

I was like, oh, you know, I am fortune, I love media, and he’s kind of sarcastic And he’s like, oh, yeah, you love media. Like, how? And I looked at him and I’m like, well, so I spent a decade in online advertising. I’ve done digital transformations at PBS and The Telegraph in London, and now 50% of my portfolio is media. And he looks at me and goes… we need to talk. It sort of took a lot to get there. But here’s the thing… I am fortune’s first ever CTO, I am first of my name.

Trac Bannon: 

This is a beautiful and dynamic human both inside and out. Remember me mentioning a new tattoo he was thinking about? That would add to his amazing body art and the full sleeves. He is bald and wears gauged earrings. From early childhood he wanted to look like a biker. While he had a few onesie twosie tats as a young man, it was not until 2006 and he was promoted to EVP that he got his first half sleeve. Tattoos in business are acceptable now, but in 2006, not as much. He is who he wants to be, though he is very very cognizant of his position. He is strategic in not having his authenticity. Become a distraction. This is the same advice I gave to my kids as they got old enough to decide on tats, hair color, and piercings. 

Jonathan Rivers: 

I am very good at being me and very bad at being not me. I learned over the years that it is vastly easier to be me than not.

 I think it’s really important for people when they talk about authenticity, sometimes being authentically yourself or unapologetically yourself means that sometimes you’re gonna need to apologize.

I wanted to make sure that I had a resume and set of credentials that was unassailable before I would sort of put myself in harm’s way by really doing the visible tattoos. And I still do this to an extent.

They stop here… not because I’m ashamed of them and I would love to have my hands done. I’d love to have my neck done, but I’ve chosen to be an executive and I’m not ashamed of any of it, but it’s a distraction. And this is why my neck isn’t done. My hands aren’t done. When I walk into a boardroom, I want to be taken seriously. I want them listening to what I’m saying and the message I’m conveying. Not looking at a giant skull or dragon on my neck wondering how much that hurt. It makes doing my job more difficult and it’s just unnecessary. I call my earrings and my tattoos job security, keep me from ever having a job I don’t want, right? Because if I walk in… if I’m applying for a C-suite job or talking to somebody about a C-suite job, and if somebody cares that I have earrings, Oh, dear Lord, they’re not gonna like what I do.

Right. 

Trac Bannon: 

See what I mean about being wicked smart? Kind of interesting that Jonathan self describes himself to me as decently smart. I’d say he’s so smart that he knows the best way to deal with authority. 

Jonathan Rivers: 

You know, that kid that had huge problems with authority, he realized the best way to deal with it is to become authority and have less people who could tell him what to do. 

Trac Bannon: 

Jonathan has plenty of folks in his network, and they are just as deep technically as he is. Like Jennifer Ives of Watering Hole AI. They recently had lunch and discussed the digital disruptions on the horizon. Of course, it was generative AI.

Jonathan Rivers: 

I don’t even want to talk about it. I’m so tired of talking about AI to sort of everybody, but it’s funny and I’m gonna paraphrase Jennifer, because I actually, I had lunch with her last week and she was talking about big AI versus little AI.

And I think everybody is distracted by little AI which is this generative stuff, and I was doing speech rec back in the nineties. Generative AI is just natural language search. I feel like LLMs and generative AI is kind of like Apache, the software.

 It is going to be the vehicle that drives excitement and adoption. The internet would not exist if it were up to Oracle and Microsoft. It was open source software, you would not have the internet if you did not have Apache, GNU and Linux. 

Trac Bannon: 

For someone who said he had no mentors, it turned out that he did have one. And for someone who said he had no real regrets, he also has one. 

Jonathan Rivers: 

I feel like… it’s funny how my career got to where it is, and I missed a shot by one point, and I always feel like this is the story of my life where I missed something by like one point. I wouldn’t want to be 18 again, but I would want to score two points higher on that test. So I could have gotten into signals intel. I think knowing where I’ve landed now and my propensity for computers and my, understanding of technology, I would’ve loved to do that.

Because I mean, you look at the DC area and, all the cyber, like everybody’s outta signals, Intel. And I just, and I’m like one, one point. He beat me by one point.

Trac Bannon: 

What would Jonathan say to his younger self? The same thing that he says to peers and his team. And he doesn’t just rest with his story, but shares the story of Henry Rawlings, the lead singer of Black Flag. Henry Rawlings was working at HagenDas making minimum wage when he said yes to an opportunity. It was 1981 and his fave band, Black Flag, was looking for a new lead singer. They called him after they saw him jump on stage a few days earlier to sing along. Jonathan was so adamant that I understand the point that he emailed me the link to Henry Rollins YouTube video and this statement… ” While our experience isn’t exactly one to one, I think you can see the connection and tie in of mentality. Too many people are scared by opportunity. They don’t realize that by the time somebody calls you, they already think you can do it.” 

Like Henry Rollins, Jonathan Rivers says yes. 

Jonathan Rivers: 

When that one knocks on your door, you say Yes. Doors open and all you gotta do is be looking for them. I have the chance to create opportunity for people. I’m a giant shithead. I have fought my way here. I have brawled, scraped, bruised, and just like fought the system because I thought it was fun, right? And ’cause I’m wired that way. Not everybody is. And dudes like me don’t get here. And now my job is to open the floodgates for as many people as I can who don’t have the shot.

Trac Bannon: 

What will Jonathan Rivers do next? He admitted he’s not sure. He will wait for the next opportunity to present itself, and the whole time, he’ll keep in mind some very wise words from Stephanie.

Jonathan Rivers: 

It’s actually a struggle, I don’t know there’s going to be anything hard enough yet that hasn’t sort of come to me. I’m waiting for that next opportunity to present itself because when it’s time to move… doors open, people call me… things happen. It just does. What I’m really aware of at that same time is something that Stephanie said to me, which is, you can only breathe the air at the summit for so long.

Trac Bannon: 

And that’s a wrap for today’s episode of Real Technologists. I want to thank my guest, Jonathan Rivers for sharing his story. Your insights and experiences are truly inspiring. I’m grateful for the opportunity to share them with the audience. This podcast is a Sourced Network production and updates are available weekly on your favorite audio streaming platform. Just search for real technologists and consider subscribing. Special thanks to our executive producer, Mark Miller, for making this show possible. Our editor and sound engineer, Pokie Huang has done an amazing job bringing this story to life. Thank you both. The music for today’s episode was provided by Blue Dot Sessions, and we use Descript for spoken text editing and audacity for the soundscaping. The show distribution platform is provided by CaptivateFM making it easy for our listeners to find and enjoy the show. 

That’s all for today, folks. This is Trac Bannon. Don’t forget to tune in next week for another intriguing episode of Real Technologists and something new to noodle on.