Nobody Cares About Your Career with Erika Ayers Badan & Michele Romanow

Hello. Thank you, thank you. All right. As CEO, our next guest scaled Barstool Sports from a niche blog into a digital media giant valued at more than half a billion dollars. For a candid conversation about leadership, the essential lessons, and the harsh truths about what it takes to really grow your business and career, please join me in welcoming from CBC's Dragon's Den, Michele Romanow. And CEO of Food52, Erika Ayers Badan. A big warm welcome.

Great to be here.

I did, yeah. From San Diego, which is a lot different than Canada.

Oh, it was long. I mean, who here—are there Barstool Sports fans in the room? Nice. Okay. There's got to be Spittin' Chiclets people here, I would think. I had gotten to be the CMO of AOL, and I was working in New York, and I hated it. It was all I had ever wanted, was to be a CMO, and I finally got the job, and I was like, "This job sucks. I can't stand this job." It was really bad.

So, I left to go launch a startup in music, which was about connecting music artists to fans. What I saw in my time at AOL was that when you looked at social, which was fairly nascent at the time, all that mattered was like the Kardashians and music artists. And I was working with Justin Bieber, and he was about to launch the Purpose album, and I was trying to figure out how he could create more business for himself based on how people felt about him and his music.

And I modeled it on this little blog from Boston called Barstool Sports. I was from Boston. I read it when Dave Portnoy handed it out at the train station; I would read it in the morning. And I was a Patriots fan, and so I was reading about Deflategate, which was happening in the NFL with Tom Brady, and at the bottom was this ad to buy "Free Brady" t-shirts. And I bought five. And I was like, this is a brilliant business model where you can make people feel something, and then you can create a commerce experience, and it actually feels like you're getting closer to the thing you care about. You're not feeling transacted.

And I really believe that that could happen in music. Long story short, we had gone to raise money, and the investors behind Barstool had said, "Hey, you've never heard of this company, but we just invested, you know, $12 million in Barstool Sports." And I pulled out the app. I was like, "It's the jankiest piece of technology you've ever seen, but this is a brilliant company, and blah blah blah." And long story short, three months later, I wasn't even hired at Barstool—I was already working at Barstool. And then we had a pretty big run from there.

2023 was a big sales summer.

We had the tiger by the tail. When I got to Barstool in 2016, the brand had been around since 2004, and Dave likes to say he invented the internet, which is so arrogant and also so great. But what he had was a fandom that you can't build anymore because there's so much fragmentation. Within 10 years, there will be over a billion influencers on this planet. So if you just think about the fragmentation, there will be over a billion influencers; there's 50 million influencers now.

Yeah, this like really vibrant fan base. It's very hard in the media business where you start every day with a blank page, and the only thing we had to propel us was really how much opinion we had, how loud we could be, how great the reaction was.

And that's what made people pay attention. What I really did was to build a business architecture around that, which was to say, "Hey, let's make podcasts." Podcasting was just starting. "Let's do live video." Live video was just starting. I found that they got into trouble if they were bored, so I really wanted them very busy.

And so I just kept them making content constantly, and then the money followed. We probably grew from 5 million uniques in 2016 to, I think, Barstool just passed 250 million uniques. So the growth in audience was really fairly crazy.

I think most people don't like controversy, which is why it's hard to grow a media empire. If you don't care what people have to say about you—which is why I wrote a book called Nobody Cares About Your Career—if you don't care what people have to say about you, you can accomplish a whole lot. The thing about Barstool was it wasn't that it was so much controversial; it's that it was highly, highly opinionated, and they really did not care who they offended. It was like equal opportunity offense. That was important. When we looked at talent, we went from probably 12 people in 2016 to, when I left, there was probably 400 people. When we would look at talent, there would be the people who you could tell were ready to be a talent at Barstool Sports, and the people who weren't. And the people who weren't were like, "Hey, I like my nights and weekends, and I'll respond when I feel like responding." The thing with Barstool is something happened, and someone had an off-the-cuff opinion immediately, which is a lot of things to chase and a lot of things to say. That's where you end up in controversy, because the internet is very polar; there's any kind of Twitter or X imaginable, so any reaction you have has an opposite reaction.

I'm much harder now than I was when I got to Barstool. I was really surprised by it. When I was starting to hire women—when I got to Barstool, I was the only woman—when I was starting to hire women, I would be like, "Hey, just make sure you don't have any nude pictures of yourself on the internet. People are going to go looking for those." They will be found. When you have a rabid fan base, they want to know everything about you. One of the things that we did very well as a company was we made a reality show; the cameras were always on.

I had no intention of being public. I'm not nearly as interesting as 99% of the people at Barstool, but because the camera was always on, you just got used to being more public. And then, by virtue of being public, when things happened, how you reacted to it mattered.

And you kind of just have to go with it.

Before I got to Barstool, there was one woman who had been at Barstool Sports, which was Jenna Marbles, who went on to be a pretty fantastic YouTuber and big success of her own right.

Yeah, she was at Barstool. She worked in a tanning salon in Boston, I think.

Yep. They created a brand called, I think, Stool La La. Anyways, I still think sports media is very male-dominated. When I worked in sports and when I worked at Barstool, I was usually the only woman in the room. I was actually around more women at Barstool than I was if we were at Sirius or we went to ESPN or we were talking to the big broadcast companies. It's changing. You look at what's happening around the WNBA and you look at the energy around women's sports, and I do think it's changing. But the reality is that to really affect change, it's going to require men to give women a chance. That's how I got into sports, which is Dave and Peter Chernin gave me a chance. But I think it's something that women in those positions have to be highly, highly visible, because there is still a lot of change that needs to be made.

I always wanted to put my gender out there and then take it away. For me, I sit on the board of a company called Axon, and the CEO was reminding me the other day that the first time I met him, I had a sweatshirt with a pair of boobs on it because I was doing Breast Cancer Awareness Month. He was like, "You were wearing a sweatshirt with a pair of tits on it." And I was like, "I was, but then I wanted to have a conversation about your international rollout strategy." So I think putting your gender out there, being unapologetically who you are, is a big piece of it. I was never afraid that I was a woman, though I did recognize that I was different. It did piss me off when people would cut me off when I was trying to speak or being mansplained, but so long as you're willing to call that out, I think you're fine.

100%.

Yeah.

Yeah, I totally agree with that. I hate the "girl boss" thing. I just think it's gross. And I hate when people are like, "the first female CEO of Barstool Sports." I was like, "No, I was the first CEO of Barstool Sports. I just happened to be a woman." So, your gender gets in the way or matters as much as you feel it matters. And for me, I didn't really want to think about my gender at work. I didn't care to think about my gender at work.