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[upbeat music] This week's episode of the Rebooting Show is brought to you by Permutive. The rules of advertising are changing. Consumers are concerned about how their data is being used in advertising.

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Regulators across the globe are closing in, and browsers are blocking third-party data. Publishers and advertisers need to develop responsible marketing practices that protect consumers' data.

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Built on the core principles of privacy, consent, and transparency, Permutive's audience platform empowers publishers and advertisers to responsibly activate audiences without any third-party access to personal data, offering insights, modeling, and activation in cookie-restricted environments.

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The data decisions that are made today will impact your ability to continue to effectively execute digital marketing in the future. Join Permutive in the responsible web. Find out more at permutive.com.

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That's P-E-R-M-U-T-I-V-E. But this other side of things, the consumer goods business, like if we do things the right way, and we think we are onto a few products that will disrupt some categories,

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that could be a much bigger business than the media business itself, right? Oh, yeah. So i-if you wanna get to the B word, this is the side where it's gonna come from.

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You know, the bills-the billion-dollar digital media brands- Oh, I was, like, going through all the B words. Are very few and far between. I was like- [laughs] Come on, billion. [laughs] Okay, sorry.

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I gotta think bigger.

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[upbeat music] Welcome to the Rebooting Show.

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I'm Brian Morrissey. Quick thanks to all of you who have left a review and given a rating to this podcast. Um, I appreciate it.

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If you can take the time and head to Apple and leave those, it's always an interesting experience to try to grow something new, particularly podcasts.

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They're totally different dynamics than newsletters, but as always, any tips or feedback, send me a note. I am bmorrissey@gmail.com. This week, I'm joined by Deirdre Lester.

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Deirdre recently left her job as CRO of Barstool to join Outsider, a media brand out of Nashville that aims to occupy the niche of lifestyle around what I think of as a Southern-inflected version of the American lifestyle: outdoors, country music, college sports.

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It's definitely more rural than I'm used to.

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But to me, it's a version of the American brand and lifestyle, and you could just as easily come up with a different flavor of brand, depending on where you come from, that would revolve around hip-hop, basketball, streetwear, and the like.

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I think they're both valid. There's, uh, probably a different, like, West Coast, uh, version of it too. That's what happens when you have a giant country.

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But I think what's important is that Outsider speaks to a specific group of people, not necessarily defined by geography, but by shared interests and a way of looking at the world.

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Some of the takeaways that I had from the conversation, one of them is that high-engagement media has different dynamics than low-engagement pageview media.

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But Barstool is not without its detractors, but I-I've honestly never seen a publishing brand with the kind of connection that it has to its audience.

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This opens up a ton of opportunities to use that connectivity in interesting ways beyond the standard business models of publishing, which tend to boil down to ads and subscriptions, mm, maybe some commerce now.

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But you can make money off, uh, off these audiences a whole bunch of different ways. The other takeaway that I had is that the future of media will definitely put talent first.

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I mean, Outsider is building an institutional brand for sure, and that's still important, but it's also doing so by putting personalities front and center, like Jay Cutler, former NFL star, and, and Marty Smith, who has a very popular podcast with Outsider.

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The third takeaway is that publishers, um, wanna be product companies. P-product companies wanna be publishers. Uh, remind me if you've seen this before.

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But if you have high engagement, you probably, as I said, wanna do more than just ads.

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You know, Deirdre saw this firsthand at Barstool about how that tight tie that it had with its audience could lead to transactions, whether that was betting on sports games, buying merch or co-branded products, or even purchasing a pay-per-view ticket to a backyard boxing match.

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And the fourth takeaway is that operating these different businesses is hard, and we get into the weeds a little bit about how difficult it is operationally to pull off both a publishing business and a product business.

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They have different dynamics and end up presenting different conflicts. I hope you enjoy the episode, and if you do, again, please do recommend it to others.

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I have not figured out all these growth levers, but I, I know that this kind of publishing ends up revolving around personal recommendations, so I really do appreciate it if you can help on that regard.

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Anyway, hope you enjoy the episode. [upbeat music] All right, let's get into it. Deirdre- Yeah. Welcome to the podcast. Was really interested when I saw you were leaving Barstool for Outsider. I'd heard of Outsider.

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I know Chan and Terry, at least by reputation from the various companies he founded. But I, I wanna start with, you know, first, you know, you spent,

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I guess, over four years at, at Barstool as the CRO, and you've had a, a long career in media.

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And, and when I think, you know, with Barstool, and I know, you know, the controversies and stuff aside, you know, what I always noticed is just in, like, Digiday, now I am naming it, whenever we would write about Barstool, the amount of engagement was, like, insane.

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Even for, like, a B2B publication, we got, like, an insane amount of engagement just because we wrote about Barstool, and it was just qualitatively different than other companies. And explain sort of

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seeing that, like, up close, a brand with that kind of resonance with its, its audience, because there's a lot of publishers out there talking about community and having a tight...

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But they really, they're low engagement.Yeah.

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I mean, I think that Barstool is the, you know, bellwether for that and the gold standard of that, and, you know, it's probably not going to be matched by many, but it's envied by all, uh, the media companies or many of the media companies that I kind of encounter and speak to today, particularly in the digital landscape, but just generally.

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I, I think that, you know, I knew going in that Barstool was different. You know?

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Why I knew that was, you know, when I first met with the CEO, Erica Nardini, you know, she was sharing with me the business model, uh, some of the current financials at the time, which was in 2017, you know, far smaller than it is today.

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But what struck me was the size of the e-commerce business.

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And when you look at what that in business was in 2017, it was primarily hats, T-shirts, hoodies, and other wearable merch that carry the School and Stars logo, and that, or other logos of different sub-brands within Barstool, Pardon My Takes, Spit and Chicklets, other brands that [clears throat] had emerged beneath the brand.

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People wanted to wear that, um, because they were part of a community, and they wanted to, you know, represent that. And it's not that different than a sports team, you know.

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We were their, we were their badge of honor, something they were proud to wear. And, and if you start wearing it and you go around, you'll find that people come up to you, people talk to you.

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And like, you know, even in that recruiting phase before I had even joined, I think Erica sent me, like a, a welcome pack of stuff, and I had, uh...

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I was going to a Red Sox game with my family, and I wore a Barstool hat to the ballpark, and I had so many people say things or point to me or wave at me.

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So, and that's in Boston, obviously, the brand was born there, but it's now, it's really, you know, all over the country now. Fans are everywhere and recognize the brand, uh, wherever it goes.

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And they also wanna be part of experiences, which is, is a hard thing in the media business.

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Experiential is something that a lot of companies in the digital landscape, I think, you know, you point to one that has been somewhat successful, Refinery29, for a period of time.

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We're trying to create these experiential events that people would come participate in, either pay to participate or sponsors would pay for, or some combination of those things, and Barstool had that.

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Anywhere we went, anywhere we set up a tent, a table, we went into a sports bar and set up a live show, it was packed all over the country. Mm-hmm.

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So I loved that about Barstool, that we could galvanize our fans to come anywhere we, we show up. So how did that end up informing the business model?

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Because I think you, you build a different business when you have that kind of tight connection.

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Like, the reason why a lot of sort of broader, to me, like, low-engagement, um, publishers, you know, are always like upset- obsessing about programmatic and trying to, like, squeeze yield, uh, here and there, and it's important in stuff like this, is because they don't really have a lot of other, you know, options, right?

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And, but I think, like, when you do have that kind of, like, community and, you know, and I... It's overused, but from everything I saw, it truly existed with Barstool. It, it is, it opens up opportunities.

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I mean, w- let's be clear. Like, I mean, f- part of it is, like, a broad ad business would be difficult to do with Barstool only. But, like, explain how that informs the, the business model decisions. Yeah, absolutely.

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So programmatic, first of all, was one of the things that, like, if I could... I wouldn't take any digs at Barstool, and it was under my purview, so I'm t- only taking a dig at myself.

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But if there's one thing we didn't really do well was programmatic. We just kind of did the bare minimum to keep the lights on, uh, there doing that piece of the business.

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But we were very focused on distributing our media everywhere versus trying to force people back to our website or our mobile app. You know?

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We really wanted people to consume the content on the platforms they were on, whether that be Twitter, YouTube, Instagram, TikTok.

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It was not about trying to arbitrage traffic back to the website and then get the highest yield. Obviously, we did that, but it was not our...

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So therefore, we had to find other ways to monetize all of that inventory, uh, in other ways, and some of the platforms make that easier than others.

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You know, YouTube, Snapchat, uh, they have a publisher model where if you put great content there and it gets consumed, you will earn high yield ad dollars back on the platform that they're actually selling against your inventory.

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And some of them will do that and allow you to sell into that inventory. That's sort of the best case scenario. That said, you know, Instagram, there's no monetization for publishers.

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You know, it's, Facebook, it's very, it was very little. And so we knew that it was, like, on us to, to create ways to create revenue.

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We monetized our shows by integrating the brands into the shows, and I think we did an exceptional job of that.

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One of the first shows that really took off when I was there in terms of growing the business was "The Barstool Rundown."

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It was a daily show, you know, Dave Portnoy, Big Cat, Kevin Clancy, and occasional rotation of other Barstool characters kinda sitting in recliners in the office talking about the topics of the day, sports and pop culture, entertainment, what the internet is talking about, what's trending.

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It was a very straightforward show. It was very popular. It was well distributed, and it was not well monetized.

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And so we said, like, let's make it a studio, but not a behind-the-desk, suits-and-ties kinda studio, but, like, just tweak it a little so that brands can be integrated in a way that's impactful, uh, meaningful, measurable, all those things.

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Um, so we just applied some standard practices from, like, sponsored content to all of the shows.

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The other thing I'd say that we did that from the time I arrived to the time, you know, I departed in four and a half years, was diversification.

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Like, we weren't diversifying our shows and content because we needed to for optic reasons from, like, sources criticizing media companies for not being diverse.

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We were diversifying because different perspectives, different personalities, different people bring new audience, right? So the more we diversify the content-The more audience we had, the more money we could make.

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And so, you know, we- I was there when Chicks in the Office, Ria and Fran, were interns sitting in the merch room making an Instagram show, and it's now one of the most successful podcasts that is out there in the female category.

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Call Her Daddy was born in that first year and a half I was there. It's gone on to become the number one female podcast and a top ten podcast, you know, in the world.

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So bringing women to the fray, bringing, you know, people that were sports, but also just general lifestyle all across the spectrum, you know, that was a big part of the business model, and that helped grow advertising, it helped grow merch, uh, and it just kept bringing more people into our universe.

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Yeah. So then explain, what was the opportunity that you saw in Outsider?

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I know you had known, like, Shannon from previous stuffs, but, like, what did you see here that, you know, with that as a back, a backdrop, 'cause I assume that it informed sort of your- Yeah...

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you know, thesis on media. Like, why this particular property and brand, and what do you see as the potential here? Yeah. Well, let's unpack that a little.

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I think, you know, the first and foremost thing, and you mentioned Shannon. Shannon Terry, I worked for Shannon back in 2005 to 2007 at Rivals.com. He and I met...

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I was an account executive at ESPN.com, uh, and we met, and he was looking for someone to come in and run sales for Rivals.

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Uh, he pulled me out of ESPN as a young, kind of hungry and go-getter saleswoman and gave me a job, but put me way over my skis at the time, I'll be honest. Just, like, running- [laughs]... a sales organization that...

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for a company based in Nashville, Tennessee, which is a very different place than it is today. A-and, you know, it was a great experience.

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I, my only regret is that it didn't last long enough, because we were so successful, and Shannon was so successful building that business, that in 2007, uh, he sold it to Yahoo Sports.

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I did not stay very long at Yahoo, but I stayed long enough to get to know that business, and then I moved on, uh, to Major League Baseball, but I stayed in touch with Shannon all these years, and he's been a friend, a business partner, and a mentor to me.

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So when he started talking to me about the things he's working on now, Outsider and a few other companies that, uh, he's standing up, uh, pretty successfully right now, you know, w- number one was, you know, an opportunity to go work with someone who I've known a long time, I respect, and has, you know, a long list of very successful, uh, entrepreneurial, uh, digital media companies that he's founded, and also partnered with big media to, uh, exit on.

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So, uh, 24/7 Sports, PopCulture- Mm-hmm....com, ComicBook.com, uh, and Rivals.

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Then, you know, we started talking about Outsider and, and the different things that we could do with this brand, and I think it, it's a broad brand.

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One of the things I like about it is it means a lot of things to different people. Yeah.

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And we've been working really hard over the last, you know, three months that I've been there now in under, you know, de-determining and defining where we're gonna stake our ground, what we're going to put investment and resources behind from a media standpoint, the types of content lanes we're gonna, you know, try to have some authority in, get some really solid writers, get some personalities to create content and shows.

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That is something that we're actively working on every day, and where we think we can kind of really have a stake in the ground and have an ownership and a, an authoritative- Mm-hmm... position.

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At the same time, you know, I think we're very focused on the business is kinda two parts, and those are seri- cen- essentially media, everything you would think of a digital media company to be, and

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commerce, but commerce in a way that it is, it's, uh, consumer goods. So what I mean by that is it's not just merch that you put out there from a marketing perspective. We're gonna do that. We're already doing it.

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We have a really awesome line of hats, hoodies, T-shirts all in our store that we're selling. They're really popular.

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We're utilizing our core personalities to promote them, and that's helping get the brand out in the wild, so to speak, so that people are wearing our brand. I think we'll continue to see that.

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On the apparel side, we'll collab with other companies, 'cause we don't necessarily wanna be an apparel business, but consumer goods, like actual hard goods that we're creating, developing, manufacturing on our own and will leverage our media, our talent, and our community to promote and help us sell those goods to the community.

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So there's a lot on the horizon. I can't speak specifically to what those will be yet, but we're weeks away from announcing a couple of, um, big developments- Yeah...

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uh, on that front that I'm, I'm really bullish on and I'm excited about because, yes, I think, you know, going back to my previous experience, you know, media companies have long been solely reliant on either subscript- paying subscribers or advertisers.

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So p- getting people to pay for their content or getting advertisers to underwrite that content or the distribution of it or some hybrid of those two things.

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And those are good businesses, but there's another layer, uh, to unlock, which is create your own products and use your media to, to market those products in an effective way.

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I th- uh, we're betting on that in a big way and beyond that. Yeah. So let's unpack further, but I wanna start with the, the brand itself and then move into, you know, the business model.

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So the brand itself, like, who is this for? Give me the person. Like, I, I have it in my m- I can go first, but I have an idea, but I would lo-love to hear your... because you know more than me. Who's it for?

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Yeah, of course.

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It's for people who are sort of your everyday American, who enjoy American lifestyle in a lot of different form, who are not far left and not far right in terms of, you know, what they wanna do, what they wanna consume, and what they enjoy.

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And so, you know, I think a lot of, there is a lot of perception where, look, the company's based in Nashville, Tennessee, uh, which I'm excited about.

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Nashville is a town, a city I should say, that is kind of on fire right now and has been for the last 10 years, but is, is really having its, its renaissance. It's like the new Nashville.

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And I think it's a place, uh, that we can really kinda have some real presence in. So we're excited to be...

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we're scoping out office and studio space right now and some other things that, to help us put our flag in the ground there.

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We've got a big event that's happening coming in-Ah, June in partnership with my friends at NASCAR around...

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They have a race on June twenty six, and we're doing a big pre-party event with them, with Jay Cutler and Marty Smith, who are two of our, you know, founding partners and kind of tip-of-the-spear talent So I'd start with, like, Nashville as the nucleus, right?

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Yeah. But it's, it's a national brand, and it's for people who love sports, love American entertainment, and love the outdoors in varying formats.

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So, you know, some people think outdoors, and they go quickly to, like, hunting, fishing, sportsmen, and we'll have those things and those people. We certainly do. But it's people who love the beach.

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It's people who love to go camping. It's people who love to go hiking. You know, it's get outside. Outsiders, right? So- Yeah... again, I go back to the fact that it is pretty broad, but there, there are niches- Mm...

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within that.

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And so part of the build-out of the community will be to find brands that kinda own some of those niches and maybe are very small publishers and/or influencers on their own, but the collective of them can be very powerful.

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Yeah. I'm gonna compare it to Barstool a little bit 'cause I think when I thou- thought of Barstool, eh, the person who I thought of- That's a compliment.

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[laughs] Well, yeah, because I think there's a lot of similarities, I would think. Like, because, like, to me, Barstool was... Like, I went to college with a lot of the guys [laughs] like in the '90s.

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[laughs] They were all from like Canton, Mass. They're from outside Boston. From my outsider point of view, it was, like, made for those dudes. I know them from New England, right? [laughs] And it was a- Yeah...

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national brand, but it grew from that ethos. It seems to me like Outsider is...

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It's Southern in its, like, cultural thing because, like, as a temporary resident of the South, not really 'cause I'm in Miami, like, it's different.

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Most media companies have a Northeastern sensibility or a West Coast sensibility, and this is, to me... It's like being in the Northeast. It's like college football. Don't get it. Don't get it. Like, it's just not- Yeah.

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Yeah... it's not as big a thing. Now, yes, it's big in the Midwest and stuff, but if you... To me, when I go through Outsider, I'm like, "Okay, country music," as a Northeasterner, don't get it.

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The, the NASCAR- [laughs]... it's gone national and stuff like this. F1 maybe taking over that, that, that sort of... But it's, like, culturally Southern. Like, is that fair that it's like...

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'Cause when I hear, like, America- Yeah... America, America, that's more Southern [laughs] to me than Northeastern. [laughs] Yeah. Yeah, and look, I mean, when I...

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I would say we talked a lot about, you know, the middle of Am- America or the middle of the country not being coastal, but I disagree with that ethos because I think Outsider is a mindset, not a region.

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But I do think you're right. We're born out of Nashville. We're proud of that. We're gonna do a lot in Nashville. We wanna be... When people hear Outsider, we want Nashville to come to mind right out of the gate. Yeah.

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But we don't wanna be ring-fenced as a regional property or a regional brand. No.

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But we might partner with other regional brands that maybe have a really strong niche in, you know, different pockets of the country or different types of, you know, lifestyle, uh, affiliations, and that will help us broaden.

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But yes, I, I love that that's where your mind goes. [laughs] And I would also, like, you, you used the word sensibility, right? Yeah.

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That's a word you just used in terms of media companies, most media companies, and this was part of the outsider as we developed what we were gonna bring to market with the brand.

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I don't think media companies are sensible right now. I think they're either pandering to the far left, pandering to the far right, depending...

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Some of it's based on where they are, whether it's LA or New York, and some of it's just, like, they feel like they have to be far left or far, far right, and it's like people are tuning out. No one wants to...

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Like, yeah, I gotta know what the news of the day is, but I really don't care about certain people's opinions [laughs] about that news of the day, and I don't want that shoved down my throat, whichever side of the politics or whatever- Yeah...

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you're on. We're, we're- You guys are not gonna do... You g- You guys are not doing politics, right? I mean, 'cause, like, let's face it, everyone gets pulled into the politics. You brought it up.

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I wasn't gonna bring it up. But, like, everyone gets pulled into the, "Oh, you're woke. You're not woke. You're, you're right wing. You're not w..." Like- Yeah... everything. Like, and you saw ESPN go through this.

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You saw it, like, with Barstool. Like, it, it seems like it's culturally we're going through a weird moment, and maybe it's forever moment, but I don't think so. Yeah. Um- I would say you're right.

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We, we are not a politics brand, and we are de- de- decidedly not doing politics.

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At the same time, I will say we will be unapologetically proud of being American, and you will see the American flag on a lot of our products and on our hats and on our hoodies because this is an American brand, and we are proud of the fact that we carry that flag.

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So we aren't going to sit around and create shows debating politics or sharing our opinions, our personal politics, but we, we won't shy away from being proud of the country- Mm... we are all proud to live in.

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And, you know, you mentioned college and the South, like, you know, uh, think about, you know, our founders' past businesses that has, have been successful. So many of them are surrounding college sports.

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So it says something that, uh, the most successful businesses in college sports today, a lot of them were born out of the South or out of Nashville, Tennessee. Yeah. Well, it's funny.

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Like, America's, like, three, 300 or 40 million people now, so, like, the... What America means is very different to, to... It's just such a massive brand, if you will. [laughs] So, like- Yeah...

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to me, it's like there's, this is, like, a particular flavor of that. Doesn't mean it's the only one, but it's definitely, you know, the outdoors life and probably freedom. But, like, I would guess, like...

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But then again, and, you know, with hunting and stuff like this, it ends up getting tied up in, into, into the politics of gun control and stuff like this.

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So it'll be interesting to see how you navigate this 'cause, again, you've seen how, like, brand publishers [laughs] get pulled into a lot of the political debates pretty easily. Yeah. Yeah.

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I mean, it's hard, it's hard not to, and I think, you know, again, there will be probably moments where people's different...

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We're gonna bring in a lot of different personalities, and I mentioned today our current-Roster is really a handful of people you've never heard of, and Marty Smith from ESPN and Jay Cutler. Two- Yeah...

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you know, awesome people with very different audiences, very different backgrounds, and, you know, potentially very different politics. For all I know they could have the same. I, we don't really wanna get into that.

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You know- Yeah...

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Marty is, his podcast, he's talking about, he's showing the other side of himself, the side you don't see on the sidelines when he's covering SEC football or other, uh, big sporting events or the, you know, the Masters.

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And Jay is doing the same. It's like everybody knows Jay for being a superstar QB in the NFL and then being on a reality show on E! for a number of years.

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But, you know, the side of him now is he's an interesting guy with, you know, a lot of intellectual curiosity, and he's interviewing folks like Tony Robbins and other notable personalities from all walks- Yeah...

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of life and getting their stories told. So we're in the process of bringing out a bunch of other personalities, and I would say they're not all gonna share the same views.

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But if w- if we stay out of the politics, then it shouldn't matter. Yeah. I think Barstool did a really good job of staying out of politics as well, but a few times you got pulled in, right?

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Dave got invited to the White House to interview Donald Trump. Yeah. Well, his viewpoint on that was, "I don't care who's the president, if I, if the White House calls, I have an invitation, I'm gonna go."

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And he kept the interview fairly, you know, not overly political, but it, that caused a ruckus inside of Barstool, because not everybody- Yeah... agreed that he should do that. Yeah.

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So it just shows that, like, companies b- a- as we get bigger, a company will reflect society to a degree. Sure. Different people inside the company have different viewpoints.

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Look at Joe Rogan at Spotify, like, there was like a... They had, like, a mutiny on their hands of employees that were freaking out that, you know, Spotify brought Joe Rogan into the fold. Well,

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Joe Rogan's one of the most popular podcasts in the country, if not the most popular podcast, I believe. And, um, for those people, that small group inside the company to think- Yeah... how could we support this?

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It's like, well, what about all the millions of people that listen and, and- Right... care about what he has to say? So I don't know, it's an interesting point- Yeah...

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you make and I think, um- Although that died down, right? Like, Spotify just, it died down. Like, you don't hear about it anymore. Netflix kinda like that. I know. Well, you know what? They got bigger problems.

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When, uh, when those deals expire, it will be interesting to see what happens, uh, with that. Do they cont- do they continue to invest in that?

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Uh, so the other thing that's like, and then I wanna get into the monetization stuff is, you know, Barstool, I think, was one of the first exam- not a, well, it was a prime example of a media company that was, that really put the talent at the forefront, right?

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Like, so, you know, usually the sort of, you know, the people, it's the brand is, like...

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And I think what's interesting is the most powerful brands are gonna be collections probably of people, because people have more connections to other people than they do to some, you know, faceless entity.

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And y- ideally, you want both, right? 'Cause I think it's overdone, the sort of, you know, influencers and creator stuff, like, is gonna be, to me, like, a little bit of a niche phenomenon in most areas.

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But I think when you can take the best of, of that connection that people feel with individuals, but you can marry it with an institutional brand, it's the most powerful, um, combination.

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So explain how you're thinking about that with Outsider, 'cause it's pretty clear you're trying to put, you know, personalities, whether it's, like, Jay Cutler or, or others, at the forefront of an institutional brand.

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Yeah. I do, uh, I think from a business model standpoint, I think we wanna create IP, and we wanna own that IP. And it's hard to own IP when the IP contains an individual's name.

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And I'm sitting here right now with two major shows, the Marty Smith podcast and Uncut by Jay Cutler, so, you know, we haven't exactly succeeded at this yet. But, you know, we will create our own IP, but we need talent.

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Everything is riding on talent today, you know, and it, you know, there is such a democratization of media hap- that has happened and is not going, the toothpaste is not going back in the tube, right?

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You can become a up-and-coming rising country music star today by putting your music on TikTok.

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It was a phenomenon during the pandemic when all of the tra- touring and, and, and travel and concerts got canceled, that some of these young artists that had maybe been moving to Nashville, trying to make it, just going to the, all the different bars and honky-tonks in Nashville to perform to try to get discovered, and all of that shut down.

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So what did they do?

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Well, some of them probably just threw in the towel and are never gonna be, you know, make it, and others turned to TikTok and created songs and trended, started trending on TikTok, and those are some of the rising stars.

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It's where we're looking at, 'cause we're doing this, like, lunchtime live show where we did it yesterday, actually. We go live from Outsider HQ. Uh, we have some of our people there. Jay hosts it.

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Uh, it- it's kinda the Outside lifestyle. We're, we're barbecuing, we're drinking beers, and we have an up-and-coming Nashville country music star there playing acoustic guitar on our porch.

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Where are we sourcing those people? We got a list of TikTok stars that we're going after, and they're all local to Nashville, so it's easy to get them to come by the office and play with us for 40 minutes.

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So I think, like, talent is crucial and, but those talent need support. They need the support of a bigger media entity, so, you know, the production.

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You mentioned as we got on here, like, your producer isn't here today, so you're doing all the things yourself.

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[laughs] But I'm sure you like it a lot better when your producer is here, and can make this- Yes, I miss you, Jay... you know. I miss you. But it, it's a collective too.

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Like, you know, you, you bring in new talent, you know, we can help them by giving them resources, by giving them, you know, support from a business perspective.

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We can have, you know, some of the more established talent help nurture the younger up-and-comer talent or the newer talent that has not been used to having resources around them.

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So I think that model applies here, and it's something, you know, I did see work really well at Barstool.Yeah. So how, how does that end up informing the business model?

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How are you thinking about the multiple revenue streams that all sort of sustainable media companies need? Yeah. Yeah. Well, you mentioned it, it at, at the top of the mee- uh, conversation was programmatic.

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I mean- Yeah... one of the things that I'm fortunate coming into Outsider is, you know, Outsider, uh,

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did, you know, reach 60 million unique visitors last year and had a multi-million dollar revenue stream from programmatic, no direct sales.

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So, you know, that's a flywheel or apparatus that Shannon has built for all of his companies, uh, currently operating a college sports brand called On3.com, and I'm sharing a lot of the resources for Outsider across that business.

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So, you know, I don't have to go hire a head of ad ops right now to build a programmatic stack. It's already there when I got there. Okay. So we're building on top of that. So that's a base layer, right?

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But then we need to build IP and sellable assets that we can take to mar- and get sponsors on board, uh, which is already starting to happen. We've got a few things going on there already.

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I mentioned NASCAR, they're a partner.

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And then I do think that all those things that you do to build a media company, there may not be a subscription business, at least not for the foreseeable future, although On3 is entirely a subscription business, so there's probably a play down the line.

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But this other side of things, the consumer goods business, like, if we do things the right way and we think we are onto a few products that will disrupt some categories,

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that could be a much bigger business than the media business itself. Oh, yeah. Right? So y- if you wanna get to the B word, this is the side where it's gonna come from.

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You know, the bill- the billion-dollar digital media brands are- Oh, I was, like, going through all the B words. I was like [laughs] Come on, billions. Okay, sorry. I gotta think bigger.

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Okay, so- But that- The- That is it. I, I do think that side of the business, and I guess it's not tangible for you today because it hasn't started- No, I get it... happening. I get it. But it's coming.

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No, I, I think what's interesting in that is it's like we've been talking about content and commerce probably [laughs] since, like, I don't know, I, I think I first, like, heard it from, like, Bolt.com in, like, uh, 2000.

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But, like, uh, it's actually a, a reality now. And I think what's interesting is you come at it from different directions.

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You've got some people who are coming from the commerce direction and are trying to build media because it's a more efficient, you know, customer acquisition tool. And then you have people- Yeah...

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from the media side who, who wanna add the commerce because it's a much more efficient than, scalable business model than selling ads. You know, programmatic is great. It's...

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But, like, you know, that is how you get to the B word, and people come at it from different, from different directions really. Yeah, I think it, it, it's easy to say content and commerce and then sell- Mm...

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a bunch of hats and T-shirts, right? Yeah. It's easy to say that.

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To start developing your own products, you know, sourcing materials, whether it be apparel, whether it be hard goods, whatever it might be, whether it be a beverage brand. You know, a lot of...

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You see a lot, Barstool that was very involved in the, you know, created Pink Whitney, which is massive success, has a big partnership- Yeah... with High Noon, but they're not making that product.

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They're partnering with people who have the manufacturing capability. To actually manufacture your own goods, there's a lot more money to be made there. It's a lot more margin, but it is a lot harder. It takes more work.

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It's very time, uh, consuming, and it... You have to have a lot of patience because the lead times- Mm-hmm... are not three to six months, they're 12 to 24.

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So, um- And it's operationally different- We'll see, you know... they're different businesses. I think where a lot of people, I think, like, get screwed up is that they're, they're...

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And I think where, you know, I've heard some of the hiccups, uh, at some of these publishers that have, that have, you know, gone hard into commerce and, like, real commerce, not affiliate or merch, because it's a really different business.

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And, and, you know, I think that's the hard part. It's, it... On the same token, if you're a product company, you know, publishing and media looks easier than it is, I'll be honest [laughs] with you.

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And, like, they realize that it's harder. That's right. Uh, but it's a totally different skill set. But is that, like, the sort of...

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You know, 'cause a lot, in some ways, like, this reminds me of, maybe this is a comparison you won't like, but it kinda reminds me a little bit of, like, MeatEater to some degree.

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I mean, they're a little bit more, like, you guys are a little bit more lifestyle and culture sort of thing, I feel like.

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But, like, you know, MeatEater has their own, like, you know, whiskey or bourbon or something like this, and they, they bought, like, a technical apparel maker or something.

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I don't know a lot about them, so I can't really comment- [laughs]... on the business. But yeah, I think, you know, we're...

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Like I said, we will do all of the things over time, and it takes a lot of time, but we will, in some cases, partner because it just makes more sense to partner in certain categories than to go through the pain and process of trying to be in a business that you can't necessarily be in, particularly low margin businesses like apparel.

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And then there's other places where we're gonna go at it on our own. So we'll see if we, we can do better than MeatEater. [laughs] I think MeatEater's doing pretty well. I don't know.

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I haven't checked in on them, uh, in a little while. But a lot of the Chernin Group, you know, companies are this way. Like, Food52 went down this path, you know. And Hodinkee, to a degree, was well.

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I mean, these are completely different categories, but to me, like, there is some- Yeah, yeah... commonality there, right? Definitely. You know, we...

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It's funny 'cause Chernin, early in the process, I felt like early in my time they were more present and involved in Barstool but, you know, as time went on, you know, at least I was further and further removed from them.

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But often they would say, "Hey, you know, we just invested in Food52. Can you meet with, you know, their-CEO or CRO, whomever, just to give them some perspective and share resources.

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I thought that was a very, y- you know, very interesting brand, very interesting company. I saw their CEO just recently, now she's leaving, but I, I haven't checked in- Yeah... to know how they're doing. Yeah.

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But you're right, there was a more of an emphasis on, in fact, she I think came from, I wanna say Walmart. I, I could be- Yeah... could be Target, but it's one of those places.

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A- and it was because they- Yeah, I don't, I don't know what's going on at Food52 or any like that, but I do know it is difficult to ma- to do both. Like, right? It's just reality.

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Like, you know, I've definitely, you know, heard def- different things about different companies where it's just, it's tough to operate both businesses. Yeah. Yeah.

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And particularly when they come into con- c- conflict with, like, brand partnership businesses. Like, sometimes it's just, they're just different.

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So that, that's a, a good one, uh, to tap into, 'cause I was very close to that at Barstool.

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Obviously, I ran the whole brand partnerships business, and I also led a lot of the early licensing partnerships, like the ones with Pink Whitney and High Noon.

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You know, we were big enough as a company, and we had enough audience and enough div- diver- diversified audience that we could create these swim lanes, as I call them.

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So we could partner with multiple brands in the same category and even create our own licensing product brand. But we had to really ring-fence it so that we didn't have...

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Because you still have to main some- maintain some level of competitive separation. I'd say in the alcohol and spirits category, we probably pushed it to its limits. Mm-hmm. We'll see.

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I don't know what they're working on right now over there, but I know that when I was there, we felt like we had pushed it to its limits, and we really needed to start diversifying categories of brand partners and licensing partners.

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Because you're right, it's hard to extract millions of dollars from brand partners when you're also competing with those partners. Yes. Yes. That's it. [laughs] A very difficult thing. Yeah. And, and frankly- I, so-...

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you know, there was a hypothesis of, like, well, we're so successful in this category with advertising. It was by far and away our largest advertising category, so then let's go into that category.

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But then all of a sudden, you better be able to make up for the lost ad revenue when [coughs] Anheuser-Busch pulls out, because they don't- Yeah... like how you're competing with them.

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So I think that is something that stopped a lot of other established media companies from doing this for years, you know?

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Could ESPN have had their own beer and put it on SportsCenter and College GameDay and been hugely successful?

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Maybe, but they had a lot of stake in that category, and they weren't going to do anything to jeopardize advertising, was their, their bread and butter, right?

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So I, I think that a challenger brand like Barstool has gotta do what it's gotta do to grow and is unafraid of kind of some of those, uh, potential consequences. Yeah.

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So I mean, product is obviously a big one, but also, I would guess experiential is going to be a big part of the model. Yeah, I think it's going to be a big part. It's actually one of the first things we're doing.

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I mentioned we're doing a big event in Nashville. Uh, we're partnered with NASCAR on it, so there's already a... I don't know if you've been to Nashville, Brian, but there's these buses- I have...

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that go up and down Broadway. Yes, with the- We've already wrapped one... bachelorette party central in Nashville- Yes... I believe. [laughs] Yeah.

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We've already got our bus wrapped outsider in NASCAR, and we'll start any day now going up and down Broadway, so hopefully we'll get some, you know, social media cred out of that.

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We partnered with a group called Whiskey Jam, which is a big, uh, country music, uh, concert that happens at a bar called Losers, uh, which is a popular place in Nashville. Um- I've been there... it's a big a- I know it.

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Oh, you've been to Losers? Great. Yeah, yeah, I've been there. Well, so you can envision the big Whiskey Jam parking lot. So we're doing a big takeover of that on June 23rd.

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We're gonna do live shows for, uh, Jake Cutler.

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Uh, he's bringing on a, a guest host and some, uh, drivers from NASCAR, and then also Marty Smith will be there and doing a live show as well, and then that'll lead right into Whiskey Jam.

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So we're excited about sort of our first, but that's just a ti- you know, that's just a starting point. I think there's a lot we can do in the experiential category.

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Our, our demographic are people who like to get off screens and go outdoors, and there's so much we can do with that.

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It's just a matter of, you know, getting the right people and practice to be able to pull those things off. Okay. And how big is the company right now? How many people? We're about 35 altogether. Good.

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How is it going back to a small company? Barstool was a lot bigger [laughs] when you left.

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Oh, it's, it's refreshing in a lot of ways, but it's also, you know, like, I, I love that I wake up and I don't have a stack of back-to-back Zoom meetings from 9:00 AM to 7:00 PM.

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[laughs] That lifestyle was, you know, m- mind-numbing at Barstool. Yeah. And it was only because we had so many balls in the air at all times, and we were innovating at all times. So we just had so much happening.

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Now it's like, okay, I have some meetings on the calendar. What am I doing with all this other time? What am I prioritizing?

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'Cause it already feels like you could become overwhelmed with all the things we wanna do, but what are the near-in opportunities that we have to get done so that we can create momentum?

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Because you've got to create momentum to get anything to happen, right? So who are the priority? Do I hire, you know, or the chicken and the egg. Do you hire the producer before you hire the talent?

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We hire the talent, now we're scrambling to find for a producer. So, you know, those are the, the problems I have today, and they're good problems.

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The one thing I would say is, you know, at Barstool, we always felt like we were flying the pl- building the plane while we were taking off.

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It just always felt like a startup culture, and I think that's something that they will try to maintain but also do a better job operationalizing the business.

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I, Erica has her podcast, and I listen to snippets of it every day, and it seems like- [laughs]... she's trying to figure out how to do things more efficiently, but not lose that- Yeah, yeah... entrepreneurial spirit.

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And I think that's a, a shadow- That's, that's the hardest thing. Yeah. It's like you, you need the process and systems to, like, truly... And because it's just, like, it gets so chaotic and, and, and crazy. Yeah. Yeah.

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But at the same time, a lot of brands and companies, their DNA is to, like, reject process and systems and stuff like this. And so, like, figuring out- Yes...

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how to implement them so they won't be just, like, rejected by the organism [laughs] is, like, really difficult. Yes. And I would say, I mean,

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I look back and at all the, at all times, we felt strapped for resources, and now sitting where I am at, I'm like, "Man, we had so many resources" [laughs] I see.... that I just didn't appreciate.

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So, but I look at all of the things I've been able to, been fortunate to do in my career- Mm-hmm...

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and all the people I've worked with and the companies that I have found the most personal gratification working at, and this is the environment I thrive in, is the beginning and the building and the getting it- Yeah...

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from nothing to something big versus trying to figure out what to do with 400 employees and an operational system. You know, there's people that are really good at that, and- Yeah... I am not one of them. Okay.

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[laughs] Awesome. Well, you're good at many other things, Deirdre. Thank you. [laughs] Thank you.

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Well, thank you so much for, uh, joining me again, and, uh, it was great to talk, and I look forward to checking in a year or so. Thank you for listening this week. We will be back next week with a new episode.

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The Rebooting show is produced by Podhelpus. Podcasts are a great way to expand your client base.

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Podhelpus lets you focus on having engaging conversations, giving your brand the full stack of services needed for a professional look and sound. Start your podcast today at podhelp.us.

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