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[upbeat music] A lot of reporting is charm, disarm, get people to tell you stuff that could get them fired, right? Mm-hmm.

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A lot of business is charm, understand their problems, and find a pathway for them to feel like you're gonna help them, right?

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And so [upbeat music]

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Welcome to the Rebooting show. I'm Brian Morrissey. Each week, I have a conversation with those building sustainable media businesses.

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This week's episode is supported by Kerv Interactive, an AI-powered video creative technology that creates shoppable and immersive experiences within any video content.

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Kerv is the only platform that uses machine learning techniques and AI to recognize depth, dimension, and objects within any video in real-time and more accurately than the human eye.

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This allows publishers to use Kerv to monetize their inventory by automating shoppable connections between consumers, content, and commerce.

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Kerv can power shoppability within streaming content, enabling consumers to pause their favorite shows and shop the scene.

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You can check this out, and I'll leave it in the show notes with a activation that Kerv did with NBCU for its Must Shop TV.

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Kerv's technology also provides real-time insights into viewer behavior and engagement, which can empower creative teams with new data to optimize campaigns quickly and easily for maximum impact.

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To learn more, visit kervit.com. That is K-E-R-V-I-T dot com. Thanks so much to Kerv.

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They've been great partners and supporters over the last several weeks, and we're actually doing quite a bit in Cannes that I'll tell you about in a few minutes.

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You know, I regularly talk to people about what they're seeing in the market and who they're impressed with as media businesses.

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I just asked this on a podcast a few weeks ago with Sean Griffey, and that's actually led to this podcast episode.

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You know, there's so much doom and gloom about the future of the media business, and much of it is warranted, let's face it.

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But there are examples of those building and not just growing media businesses, but also ones with resiliency.

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Often, these publications look quite different from the previous era, which was often about big and generalist publications.

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Because when you're optimizing to unique visitors and page views, you're gonna cast as big a net as possible. And I think that was clearly a mistake, at least in retrospect.

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The future of media, in my view, is smaller, it's more focused, and it is more about relentless execution and not big, airy slogans about unbreaking journalism or any of that.

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And I can't think of a publication that's executed as well recently as Punchbowl News.

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Started by veterans of Politico, Punchbowl relentlessly focuses on Capitol Hill and the sausage-making that is the American legislative process. The action during the Trump years shifted inexorably to the White House.

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It was the Trump show, after all. But the Capitol is where the story always turns. Just see the recent debt ceiling crisis. Anna Palmer is a journalist turned startup CEO.

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Along with Jake Sherman and Jon Bresnahan, she founded Punchbowl in January 2021, just in time for the assault on the Capitol.

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Punchbowl's obsessive focus on the Capitol and its business model that combines subscriptions with high-value issue advocacy ads led it to sprint out of the gates with a ten million dollar in revenue mark in its first year.

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Anna's more reticent about its current revenue pace, which is no fun, let's be real here. But by all measures, what Punchbowl is doing is working. Here are some things that stand out to me about Punchbowl.

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One is that it's reporter-focused, and I believe journalists who start media businesses create far different products.

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Punchbowl is very journalism-driven, relying on the daily grind of uncovering new information versus playing SEO and social traffic games. Two, it has a rich niche.

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Issue advocacy ads are a lucrative ad category, and one where you not only don't compete with Google and Facebook, but often they're your biggest clients. If only more of the media business was like this.

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Three, it stayed lean and focused.

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Punchbowl started with funding from LionTree, and it has grown quickly but has also resisted the temptation to expand too quickly by, say, springing up operations in state capitals around the country or joining the fray at the White House.

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Instead, it has focused on high-value areas for expansion, like its recent move into financial services with the vertical The Vault.

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Lastly, it has managed to be a publication about politics without being a political publication. Now, many aspire to nonpartisan news, whatever that means, and that's easier said than done.

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I mean, see the Chris Licht experiment at CNN for evidence.

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Punchbowl has managed to thread the needle for the most part without being pulled into the inevitable political Rorschach test because it's obsessed with the legislative process versus the posturing part of politics that too much of the news focuses on.

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Quick note on the podcast, next week, we'll be bringing to you a series of daily live recorded podcasts from the Cannes Lions Festival.

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We partnered with Kerv to do an event there called The New Attention Economy, and we have something like 30 great speakers over the course of three days. And so if you are in Cannes, please do join us for that.

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You can sign up in the show notes. And some of these conversations, we're gonna bring to you here as podcast episodes.

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I'll have guests like Group M CEO Kirk McDonald, Hearst CRO Lisa Howard, Bloomberg CRO Christine Cook, and Semafor editor-in-chief Ben Smith in conversation with Puck COO Liz Goff.

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And there's many other great ones, and I hope to turn many of them into podcasts that I hope you'll enjoy.But please do send me feedback about this podcast, things you'd like to hear, things you wanna hear less of.

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My email is brian@therebooting.com. Also, please leave a rating and review of this podcast. This is a great way to get people to discover the show, and I really appreciate your help in doing that.

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Now, here's my conversation with Anna. [upbeat music] Anna, thank you so much for joining me. Really appreciate it. Thanks for having me. Looking forward to it.

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So I always try to ask, 'cause people say, "Oh, you're negative," and all this sort of thing, that I'm like, "I'm really not." I just, like, I'm a weather forecaster when, like, it always rains.

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I don't know, I'm a weather forecaster in Seattle, and, you know, it rains a lot. But I actually like sunshine like a- anyone else. And I try to ask people, like, "Well, who are people you think are doing a good job?"

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Or just from the outside 'cause you never know on the inside, are, you know, you think that they're really executing really well, and Punchbowl always comes up, and it just did.

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I was just out in Washington, DC, and I asked this question of Sean Griffey, previous podcast, and he brought, he brought up Punchbowl. We appreciate it. That's always good to hear. [laughs] Okay. Is it true?

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So Punchbowl News is two and a half years old. We benefit from the fact that we are a COVID startup, right? So it wasn't as if it was the Trump sugar high of advertising, and I think most people thought we were crazy.

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And we've been really focused on what we do. I think we're super ambitious, which I think has surprised people about kind of how quickly we've become successful, you know. I mean, we were profitable in our first year.

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And so we continue to be very focused, but also really excited about the future. Yeah, I mean, I don't know if I would've been surprised.

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I mean, both you and Jake Sherman, who had been on this podcast before, were writing Playbook, an incredibly successful franchise at Politico, and you clearly saw how successful [laughs] it was.

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And John Bresnahan obviously has a long, long history. So I mean, you guys had chops and... But I think what was interesting to me when I had Jake on here was h- how the business had gone. Mm-hmm.

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So I always think, you know, people say advertising is a terrible business and so then well, let's, let's define advertising 'cause there's a lot of different types of advertising, and the type of advertising that Punchbowl specializes in is a great area.

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Yeah. E- explain for those who don't know, like, how... And we'll get into the subscriptions. Mm-hmm. But just explain this particular area of advertising. I don't even know if it's advertising anymore.

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Yeah, so I mean, I... So I've been in Washington journalism for almost 20 years, and I always laugh when everyone talks about Sub Stack and the rise of newsletters, and it's, like, the new hot thing.

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I mean, I've literally been doing newsletters for that entire time.

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The only thing that has changed is the news cycle has sped up, so I started in a very niche publication called Influence about the money of lobbying that came out every other week.

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Fast-forward, we now are on a three-times-a-day newsletter. But the reason why there is so much money here in Washington is because the business of Washington never goes away.

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Massive corporations are making huge bets around regulation, right?

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And so even if there is a presidential year, which you'd think, oh, that's a bad time to be in Washington because nothing's happening on the legislative calendar, these are 10, 15, 20-year fights that go on.

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And so there is a kind of a steady stream of just overall corporate wa- you know, industry wanting to influence what happens here. Yeah.

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And so I think we provide the vehicle for which they can get to the most premium audience that they want, which is- Yeah... the leadership on, in Congress and those at the White House.

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Yeah, and there's only so much you can spend on lobbyists, right? And the, the size of the government has...

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I, I gave reference before, I lived in Washington for, like, a couple years out, outs- out of college, and, you know, I was only making, like, $30,000 a year, so I wouldn't have bought a place there.

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But if I did, [laughs] it would be worth a lot more.

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And, you know, that's because the size of the government has gotten quite a bit larger, and it's gonna get even bigger because I think both sides don't agree on much, but, but one of the things they agree on in some ways, in different ways, is that, you know, the government is going to be more involved in the economy in different ways.

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And I think that's... If you look at the bills that are passing, like industrial policy- Mm-hmm... I always thought the US was not a really an industrial policy thing.

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Always seemed a very European approach, but we're there now. I think- So that's a great field to be in.

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Yeah, and I mean, even if you think about, like, you know, Washington used to be a cost center for a lot of these companies.

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Coming out of COVID, coming out of some of these kind of massive, massive packages, all of a sudden I think a lot of companies that maybe were skeptical of Washington now realize that playing there and having a reputation here makes a big difference.

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Yeah, and I can remember just in covering the technology companies, right? And I, I covered the sort of rise of Google, right? And before the IPO, I'm, like, dating myself quite a bit here.

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And, you know, Google got caught flat-footed when- Yeah... Microsoft turned their, like, lobbying apparatus against Google to say, "Hey, you know, they're, they're developing a dominant position."

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And Google's like, "Oh, man," because they were taking the Silicon Valley view of like, you know, we're inventing the future.

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The people who try to influence government are, you know, they're, they're just, like, the old guard. Well, Microsoft had a near-death experience [laughs] in the '90s. Right, right.

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So they had a apparatus up and running. And now I think with AI, it's a totally different game now because w- it is going to be... They're asking to be regulated. And so I don't know.

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I don't, I don't wanna tell you where to expand to. I would get in there. [laughs] First, definitely first time in my, uh, career where you have an industry who's very nascent saying, "Come and regulate us."

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You know, typically much more like Silicon Valley world where they think they're changing the world and, you know, Washington's never gonna come for them. What I always say- Yeah...

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is maybe not today, maybe not tomorrow, but Washington eventually comes. Yeah.

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But it's also, it's a mature, it's a matured industry really, and, you know, anytime anyone asks for regulation, they're just asking to be protected from competition, at least in my view.

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I mean, like-The incumbents always benefit, and particularly with these large language models. Scale, this is one area where scale, it's not like a lot of media, scale is a tremendous advantage. [chuckles] Mm-hmm.

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So you-- We're now like two and a half years in. As I said, you know, from the outside, I think it's been, like, tremendously successful. Mm-hmm. So give me the sort of report card from your standpoint.

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I assume you'll give yourself pretty good grades, but... It's, it's been a good two years. [chuckles] Yeah.

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So I mean, you started and, and I remember talking with Jake, I mean, you'd gotten to a, in year two, I believe it was like ten million in, in revenue.

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I think the mix might have been different than you, than, than you had expected. Probably more upside on, on the ad front.

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I know when you launched, it was more about, at least it was, it was marketed more about the membership and subscription, but the ads have done tremendously.

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Yes, I think we did ten million in our first year of, of, of business. Wow! See, I'm even like, "My God."

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We did significantly more in our second year, and we're on track in our third year to continue to kind of year over year. We're very confident about kind of the future of the business.

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I think partly the programmatic ads came. You know, we were... I think people kind of forget 'cause, you know, it almost feels like we're just in the lifeblood of Washington now. Yeah.

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But when we started, you know, we didn't have a list, we didn't have all these things, so we kind of were building really four people, really small, kind of the opposite model that you see so many other media startups do, which is they raise a ton of money, they ra- they hire all these people, and then they, like, kind of try to find the business model.

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I'm not a traditional CEO, and so I had been in kind of this Washington journalism space for a long time, but it was much more of like, "Let's figure out what's gonna work and what isn't."

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And so programmatic ads, we always knew were gonna be, which is like the big ads with all the companies that want to use newsletters to get in front their eyeballs, you know, of, of the really important people.

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And so that started, and we kind of undercut the market in some ways where, you know, I- we knew what everybody else was selling theirs for, and so we said, "Take a chance on us, like we'll, we'll kind of build together."

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And so we benefited, I think, from the fact that Axios had broken off a couple years, you know, obviously five years before we did.

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And so there were companies and consultants who had taken a chance on Axios and had, you know, been proven right on that. And so they were willing to kinda take a flyer on us.

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So I think that always was gonna be the baseline of the revenue. We also knew that we wanted to have a subscription business, right? So we call our audience as members, which I think we really believe.

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We talk about it in every part of our business, right?

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Where we fundamentally believe that there's an ecosystem, particularly in Washington, where a reader might be a source, might come to an event, might be a sponsor, and we wanna foster that, right? Like contact...

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In Washington, I always say, it's such a contact sport. You know, who's talking to who? What's the body language? And so we started with a three hundred dollar individual subscription.

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I think we quickly kind of saw that the way to scale that in a much better way was to have it be more of a B2B, you know, membership. So it's you, Company X has ten slots at three hundred dollars a year, right?

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It's just a much easier business model, sales model in terms of kind of predicting where your, your numbers are gonna be.

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But we did, oh, north of a million in our first year, which we felt like was really strong for us, and we have significantly grown that. And that was, when we started, we didn't even have, like, a salesperson doing that.

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I think the biggest surprise for sure for us 'cu- 'cause again, we're coming out of COVID, right? And we, we launched Punchbowl News three days before January 6th, is the kind of massive growth of our events business.

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I always thought we would do events. Mm. We had done them at, a lot at Politico. I had wa- I had also run their women's leadership platform, which is really a global events business.

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But, you know, we did roughly 40 events last year. Whoa! So that's a lot. Um- But these are why... Like, Washington has a different, like, events- [laughs] It's so funny.

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There's like, Washington is, like, a different universe really from the rest of media in some ways. I mean, there's different people, like for instance, like, I'm gonna be going to Cannes [chuckles] in like a few weeks.

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You were there last year- Yeah... so I can say it to you. Yeah. But, like, literally, they're very different worlds to some degree. Mm. Like, the world of like, right?

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Like, this, there's different ad buyers even in Washington, but then the events are very different because everyone... Like, nobody in New York wants to go to a breakfast event. Like, nobody.

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As far as I can tell, nobody does. Tell me if someone does, but I'll, I'll put one on. Uh, we'll see. We'll have Punchbowl News in New York soon enough. No, I'm just kidding.

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[laughs] [gentle music] Let's actually stick with events.

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Explain, like, the model that you're doing, 'cause 40 is a lot, but I think Politico probably does, like, 400, something. Yeah, I don't know. It's interesting.

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I mean, I think for us, the big thing that we do is we think about all this stuff is, like, what are our margins, right?

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So I think a lot of people do a lot of events, but they don't actually make a lot of money off of them. Yeah. We have kind of reverse engineered it where, you know, we are able to...

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We have one in-house person who does our events. We work with an outside or two kind of different firms that help us, but we do them at a very low, hopefully low cost, and then can make up through it.

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And the other difference, I, I do think you're right that there is a much more of an appetite for convening in Washington, is when we do them, I think we don't think of our events business as separate from our journalism.

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And so the event feeds the newsletter, feeds social media, feeds all of these things. And so especially when we started, there were four of us, like, we couldn't do an event and then, like, not put it somewhere, right?

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[chuckles] Yeah. It wasn't like there's just, you know, all these people just sitting around doing this. Right. But I think it's just much more integrated into what we're doing. Yeah.

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But- And so some of, some of those are those editorial events you're talking about. But we do a lot of, like, parties too. We do a lot of kind of high level.

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We have a townhouse as our headquarters where we do kind of breakfasts and things like that that are a little bit different than the traditional media company.Okay. W-what is the revenue model for these kinds of events?

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Are you selling tickets or is it sponsor-driven? Sponsored. Okay. Yep. So typically, walk me through it.

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'Cause I mean, a lot of the events that I see are like, it's a newsmaker event, and you have a newsmaker interview, and then you have some euphemism for the sponsor interview. View from the top or whatever.

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Like [chuckles] Oh, that's a very Axios. That's [chuckles] I don't know what it is. Everyone has a euphemism. Quoting, quoting the Jim VandeHei of it all. I call that...

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I sometimes mix in sponsor and I call it like- Yeah... spotlight episode. Whatever, we all have euphemisms. Fireside chat is usually how they- [chuckles] Okay. Fire without a fire. Okay...

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they work for, for Pungible News. Yes. So we do that, which is I think really, like that's a typical format that a lot... It has been going on for decades, right, here in town.

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Um, I think the way that we've done them a little bit differently is this idea of smaller convenings where we wanna kind of...

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We think our special sauce is public sector, private sector, nonprofit world, and getting people together in a room that don't typically get together.

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And so a lot of that, whether that's at our townhouse, um, whether that's at White House Correspondents' Dinner, we do a big kind of kickoff lunch for 200 and some people.

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Um, but that's, that's kind of our way of kind of, again, bringing our community together, and then they're always underwritten. Do you sell those, like, as packages with the newsletter sponsorships too?

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Because I mean, you'll...

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I mean, one of the things with events that, and you guys are in a, again, in like a particular area, but sometimes, like, events can take over, like, an organization very easily, depending on the kind of events you're doing, and then you become known a-as, as an events vendor.

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Mm-hmm. And you kinda don't wanna do that if you're in the publishing business. Yeah. I think you can be both though.

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Like, I think, like, listen, our north star is always gonna be having that kind of pulse on what's happening- Yeah... with the leadership in Congress, right? Like, the rest of it doesn't work without that.

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That is always going to be the most center piece of what we do. I think the events business can complement that. Oftentimes, these are lawmaker interviews that we would wanna have otherwise.

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But yes, oftentimes in terms of the, the revenue model, they're sold as part of a bundle, is how I would say. Yeah. And now on the, on the sub/membership- Mm-hmm...

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front, um, it seems like you've, you've moved emphasis from individual to enterprise B2B, however you wanna call it. Mm-hmm. But you're selling, like, groups.

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I mean, you know, running transactions, credit card, you just give Stripe a couple percents. It's like, yeah, it's great. But you're dinking and dunking your way down the field, and, you know, it, it can...

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It's a slow burn. Like, building subscriptions, like, one at a time, you know, like, get a great charge out of, out of getting that, you know, Stripe confirmation.

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But at the same time, you're like, "Oh, my God, can we speed this up?" It's tough. A subscription business is not a glamorous... It's, [chuckles] it's not a glamorous place to be.

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I mean, it is, I think, fundamental, where we spend a ton of our time and focus is making sure that we're supporting that effort because, you know, I'm sure as you talk to folks, I listen to all the time, right?

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Reoccurring revenue is kind of king- Mm-hmm... in this world, right? It's not as, as subjective to the markets or industry, you know, rise or collapse in the same way that so many others are.

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But yes, definitely, I mean, we still have individual subscribers, and that's wonderful, but I think where we kind of focus a lot of our time and attention is getting those, you know, multiple people in through one corporate entity.

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And it definitely is where we see kind of our ability to, to scale on that, to your point that it's just much harder otherwise. Yeah. And that, is that mo- that mostly is, like, a regular sale.

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Like a, a salesperson has to, like, sell that rather than someone takes out, like, a credit card for three different or for 10, 10 seats. It depends. I mean, I think it depends on how comp- some companies...

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I mean, you know, I mean, that's, that's getting really in the weeds, but whether they're, you know, you've got a vendor onboarding, or you have a, a company that's easier to expense 10 slots through one credit card.

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I think we try to be pretty flexible on that. I don't... The, the payment method is, you know, we'll work with you however we can to make it as seamless as possible. Yeah. I was mostly interested just in, like...

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'Cause I think one, one of the things you had said before is getting the size of the organization- Mm-hmm... right, okay? Yeah.

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I mean, like, very different business, but, you know, we've seen, like, The Messenger going out and, like, hiring a ton of people, saying that they're gonna hit a, a really big number in, in some so, uh, media alchemy, I'm not really sure, but it, in their first year, and, and that's, that's a, that's risky.

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And I think we're seeing, like, evidence, at least I'm seeing evidence of people who getting the, the size of the organization right is important.

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And, like, you have to craft your business model in such a way that you're not going to repeat the same problems of the past, which, you know, infrastructure got way ahead of, of where the businesses were in a lot of these companies.

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I don't know how many VPs and SVPs and EVPs Vice had, but it was, like, north of, like, 200. [chuckles] Just an estimate.

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A-and I think, you know, that it m- it matters in some ways, like, because you guys have, have been able to not just grow quickly, but stay pretty lean. Like, how big is the team overall? Yeah, totally. We...

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I mean, I think that's the big argument, right? Profitabil-profitability versus scalability, right? And so for us, profit is king. I think we wanna scale. We are very ambitious.

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We are just under 20 people right now, but we're, we'll probably end up somewhere shy north of, of 20 by the end of the year. Yeah. But that's, I mean, you know- Yeah... that's not that many, I don't think.

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Like, I mean- No. I think for what we're doing in terms of size- Yeah... and scale, for sure not. But I think, like, you know, our culture, we think a lot about... I don't know.

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I've worked at a lot of different places, some of these places that don't exist anymore. Yeah. I worked at Politico for 10 years through a lot of different iterations of what it was, was finally kind of becoming.

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And, you know, we're a company of doers. Like, we always say that, like, like, nobody should just be sitting in... I'm not sitting in meetings all day long, right? Like, I think sometimes when you get to some of these

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bigger companies, you have a bunch of people that are just kind of meeting all day long, right? Everybody should have, s- should be contributing to the bottom line at the end of the day.Yeah, that's true.

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You do have this. So, although some days, you know, as a, as a very small [laughs] I'm like, "You know, I, I could kinda deal with a, a day full of meetings." [laughs] Just kinda zone out a little bit. Exactly.

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Say a few... Yeah, just to build on what Jim is saying. [laughs] But that's not an option. So you're not gonna tell me how much revenue you're expecting to get this year, right? I'm not. No? No.

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Not ne- I don't think- I mean, come on. Jake was fun. He told me. [laughs] I know, but that was a long time ago. That was, that was... We became... We put that o- out. Um, I mean, I mean, listen, I think we've...

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It will, it will, it will be significant. I think we'll probably... We'll know more. You never co- never, uh, count your chickens before they're hatched. You know? Yeah.

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I feel like at our, where we're projected to be, but happy to talk about it once we, we... You know, we're a private company. That's the nice part about it. I know, got it. You don't have to tell anybody anything.

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But also as a private company, you can do whatever you want. You can say the number. [laughs] See, well, I, I've seen that too. [laughs] Yeah. All right. Well, I tried.

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Uh, 'cause people are like, "Hey, you gotta ask," so. Yeah, of course. I'm, I'm doing my, I'm doing my job here.

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[upbeat music] So the...

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Talk about... 'Cause I mean, this is w- it's working. Like, from everything I can, we can see, it's working, right? And then you end up, like you said, coming to, you know, how much gas do you wanna pour on?

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How do you want to expand? Yeah. How much are you going to emphasize profitability? 'Cause you're gonna end up... Inevitably to grow a business, you gotta get ahead o- of revenue sometimes. I mean, like, it's great to...

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You know, when I, when I talked with Sean, you know, he talked about expanding to new markets and getting an advertiser to basically de-risk it by- Mm... covering the launch of it for, like, six months.

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And I'm like, wow, you know, I, I would like to do that personally and if any advertisers wanna do that- [laughs]... with me. How are you thinking about expansion? 'Cause I mean, you've moved into financial services.

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I think you guys have benefited quite a bit by your laser focus on Capitol Hill and not getting even, even going towards the White House. Yeah. Listen, I mean, yeah, I think a couple things.

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I think Sean, I mean, he's built a tremendous business in some areas that are not necessarily, you know, the sexiest to some people. But I think the, again, having that focus.

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I think for us, I think he's smart, and I kind of agree with this, the strategy, right? Which is to, to de-risk, right?

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Like, if, if we're gonna go and make a big bet on something, I have to believe that there's advertising revenue. I have to believe that there's subscription revenue around it.

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It can't just be like, we're gonna just try it out, right? I think that maybe bigger companies have the benefit of, of making, you know, a two-year play into video, for example, without an advertiser.

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Like, we would never do that. Mm-hmm. And so I think when you look at The Vault, which is our financial services coverage, I think you'll see us double down on that.

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We have The Canvas, which is our kind of proprietary anonymous polling that we do of senior Capitol Hill staff that's verified, unlike anything that anybody else does. It isn't like an influencer poll.

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It's like actual verified staff directors, comms directors, you know, the people that are actually the, making the decisions behind the principals themselves.

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And I think you will see us go into other special edition areas as well, but I think to your point, like, if you've looked at our coverage, we don't have 20 reporters on the ground, somebody covering Trump every day and DeSantis, and, and you're not gonna see us do that.

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We don't think... Commodity journalism isn't for us. Like, we're not, we're not making money based on 29 million people looking at a story 'cause it hits Drudge.

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We care about the really, really most important people right in that bullseye- Mm-hmm...

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that that is why our advertisers or our, our readers, frankly, our members wanna read it because they know that Mitch McConnell and they know that Hakeem Jeffries is reading this, and they need to know what they, they're reading as well.

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Yeah. But like, an obvious, like, area would be going, d- doing the same thing for capitals in each state. That's a tough business model. I mean, you- Yeah... if you look at, uh, Politico, for example, right? Mm-hmm.

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Or others, I think, I think basing publications on just areas of, of having bodies on the ground is a really expensive proposition and probably unnecessary at this point. To me, I'm much more interested in power centers.

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So, you know, where are those people that maybe there's 50 of them in the round, the country, but they are gathering together? How can we get tho- their mind share?

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So a good example of that is the US Conference of Mayors was in Washington for their big annual conference. They'd never had an outside media partner come in.

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We worked them through kind of the process of it and how that could work, and we did an event there that was sponsored that also...

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So we were in front of a new audience that we would otherwise never get to be in front of. They got to have exposure to our audience that they would otherwise not necessarily have exposure to.

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And, you know, we were able to make, you know, have, have it underwritten by a corporate entity.

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So those are kind of the places where I think you'll see us play more in, versus let's have somebody in California or Texas or New York covering state capitals. I mean, could we... You could make an argument, right?

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I mean, you don't have to, like, do, like, North Dakota, but I mean, like- Right... California sets the, you know, they set a lot of regulations for this country at the end of the day.

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So I would guess that your clients are all devoting money to influence what happens in Sacramento or whenever, whenever Austin meets, whatever those two weeks a year that they, [laughs] they meet.

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I mean, that's the problem. I mean- I don't know what this person... Maybe you just need a freelancer. Just in terms of [laughs] Part of it is the person that, you know, problem there.

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I think the, the market size is so much smaller, right? So I think it depends on how you... I mean, what's interesting what Axis is doing on the local level- Yeah...

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'cause they're kind of trying to centralize things, so they only have to have a cr- couple people.

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I think unless you really can be indispensable, like for us, that focus and being indispensable to our audience, I think is the biggest differentiator. Yeah.

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So I think ultimately with expansion, it's like, are you gonna go broader, or are you gonna go deeper?Right? Like, I mean, you have...

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You can eas- I mean, not easily, everything is hard, but there's, there's a clear pathway to go deeper.

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'Cause I mean, you talk about, like, memberships being incredibly important, and three hundred dollars you're gonna have, you know, discount or whatever for, you know, bulk buys and stuff.

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That's great, but like five thousand dollars is way better. And, you know, and there's tons of products in Washington that have proven out this model. I mean, Politico Pro is, is obvious- Sure... is an obvious example.

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But I remember when I was down there just like, you know, hearing what like National Journal, I think it was, like, was charging. I'm like, "What? No way. No way. Nobody would actually pay that, right?"

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People do, and it's a good business. Um, I just had on Bob Cotterman from The China Project, and they've got like a five-thousand-dollar subscription. So how, how are you thinking about

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narrow versus wider or deeper, I guess, versus wider? I would say definitely more, I think deep, right? Mm-hmm. I think for us, w- why people come to us is because we're experts at what we do, right? I think unlike...

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So we felt like there was so much white space in the capital because so few reporters really wanna be there for their whole career, right?

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They're there as a stepping stone to go to the White House or to go be a national political correspondent or go do something else, right?

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Whereas you look at the core of our team, it is all about what happens in the capital.

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I think what we are doing with financial services is a really good example of where we felt like if you turn on, you know, a lot of business cable news, or you read some of the, you know, financial services industry kind of publications, it's all from a New York perspective and very little from a Washington perspective, right?

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It seemed very divorced from reality when you see what they were saying on a lot of... The debt limit and so many other things.

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And so we felt like there was gonna be regulation, there was gonna be an interest in what was happening, and we could kind of better tell that story than anyone else.

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I think you'll see that in potentially other areas, but also just where do we see some of the, the action and, and how can we, you know, of course, you know, either raise subscription rates or think about what, how does our...

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Do we have a different level? How do we kind of g- bring more value to our members? You know, they're really bought in in a way that I don't think I ever experienced in journalism before.

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I think they feel like they have, you know, they're part of a truly a community in a way that... You know, we also, we survey them, we ask them all the time, "What are you looking for? How..."

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We started texting, for example. I don't know if you've seen that- Yes... but for our, for our premium community, which is something that... I'm not saying that's revolutionary.

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You gotta, you gotta be really hardcore, right?

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'Cause [laughs] if you're getting, if you're getting the email three times a day and then you're just like jonesing for a text too, I mean, you gotta be really, really hardcore. But it's the most popular.

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I'm telling you, we, you know, and we, and I think we, we try to take a couple big swings a year, right? Like, we, we tried Slack channels, and that was, like, a little bit too crazy to do.

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And so I think s- texting has actually really been s- another way where they feel like there's a lot of value. We do brown bag lunches once a month where people- Yeah... can ask us direct questions, you know?

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I mean, there's a p- a sense of that you're really part of something, and that's something that we, we never wanna lose sight of. Yeah.

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And so, I mean, you started with newsletters and also podcasts too, but you're clearly... I mean, I think that's the fate of everyone. Like, you might start...

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To me, like, newsletters are great minimally viable product, and they're amazing as a base, but inevitably, you know, you end up expanding beyond that. H- how do you end up thinking about that?

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'Cause there's more going on on the site. I'm seeing more... I was just watching a video that you did with Google. Oh, yeah. Yeah. I was creeping on your LinkedIn and, and saw.

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I mean, we're, we're a newsletter first company. We're like- Yeah... unabashed about it. If you look at our homepage, Punchbowl.news, you can sign up for our free morning newsletter.

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That's my, [laughs] my plug for all of your listeners. But, you know, when you, when you look at it, it isn't a site that's meant to be drawing people in and, and having them kinda come back.

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I think that model is really tough to make work right now, right? We've seen that with so many different news organizations. So- Don't tell the messenger this. [laughs] I, you know, I- [laughs] We'll s- we'll see.

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I, you know, I'm, I'm, I'm... I want everyone in journalism to do well 'cause I feel like competition is great for us, [laughs] honestly. Got you in the doubter bucket. [laughs] I just try to be positive, Ryan.

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But I do think we do longer form, so I think one of the things we've done is these custom products. 'Cause we don't do paid just, you know, kind of custom content in the way that traditional news organizations do.

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We really try to find pro- projects that we as an editorial team are also excited about.

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And so we do about, you know, one to four of those a year, and I, our editorial team really likes it 'cause it's a way, instead of just having, to your point, the constraints of a newsletter of give me what you can in two hundred and fifty words, to be able to do long form, to be able to do video, and to experiment in that way.

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But again, in the same way that Sean Griffey said, those are all underwritten by a corporate entity, so we're not kind of just taking a flyer that people are gonna all of a sudden like this kind of content. Okay.

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And so with the, with the financial services coverage, I mean, when I saw that, I thought, "Okay, verticalizing makes a ton of sense," and you already have,

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you already have, you know, your clients are telling you which direction to go to some degree with the business if you're focused on margins, which I hope a lot of [laughs] people are these days. Yeah.

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And obviously I could see AI, I could see different...

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I mean, is verticalizing, is, is using that as a template at, like, one of the ideas for growth is, like, okay, if we can nail this, we can bring this to, like, five high-value areas where we can already see in Salesforce or whatever CRM, like, where our clients are sort of pointing us to some degree, and where the action is, you, you know, at the end of the day.

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I think that's right. I mean, listen, I don't- Journals... the idea is not to have... I, I w- I think the thing you won't see us do is have twenty-five newsletters coming out every single day, right? Like- Yeah...

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no one, to your point, is looking for a, a thousand more emails to go through. We already give people our cr- you know, kind of core audience three emails a day, which is a lot.

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And what's fascinating to me is Friday PM performs, like, just as well as, as Monday AM, right? I would've thought that over two and a half years you'd see a huge dip in those people that are obsessed, and they aren't.

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So that's kinda been really gratifying to see and to say, like, "Okay, like, there, there is an appetite to do more coverage." So yes, I think-The Vault, which is financial services for us, is our- Mm-hmm...

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was our first kind of dipping the toe in, let's figure out how to do this, do it really well, do it in a way that works for our audience and our voice.

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You know, but finding talent that, that is good at this kind of stuff and wants to do it in the way that we do it, I think is one of our challenges. Yeah. And, and Canvas, I always thought Canvas was really interesting.

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Is, is that, is that trying to get at a proprietary data product of some kind? I mean, it is a proprietary data product. I know, but when I say proprietary, I, I'm basically using a euphemism for, like, $5,000 a year.

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[laughs] You know, it, that's, it, it's, it's not out of the realm of possibility. I think for us, the Canvas was really born out of the idea of polling kind of being broken, and that the fact that...

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L- A lot of people came to us when we started, saying, like, 'cause we had b- been at Politico, which has a big polling partnership with Morning Consult, which makes a ton of sense for them.

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And people were saying, "Oh, well, like, you could do that with this." And for us, we were like, "The, our value prop isn't a national poll," right? Like- Mm-hmm...

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our value prop is, what do the actual people that are kind of influencing what's happening in this town, what do they think? And no one could do that.

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And so we, it was a big risk because I don't think anybody in the news business had really tried it. But again, like, I think that the people that do it really appreciate it. You know, I think that it also was...

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it's super predictive.

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If you look back over two years even o- of where the, especially on the Hill, those people thought, the, those senior staffers thought was gonna happen, whether it was infrastructure or others, that e- everybody in the media business was like, "Oh, this is never gonna happen," they were, like, steadfast and strong on both the R and D side on a lot of these issues.

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And it's pretty interesting to look back over the year.

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[upbeat music] So a couple quick questions on the coverage area is the debt ceiling thing, I, like, tried to avoid it.

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If there was, like, a block, so I was like, I know they're just gonna compromise in the end. I know that you guys have to, like, be obsessed about it and everything like this.

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I'm just telling you from, like, the rest of the world- Mm-hmm... I'm like, this is all just kabuki theater, and ultimately we're not gonna go into default- Mm-hmm... and there's gonna be some messy compromise.

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Nobody's gonna be happy, et cetera, et cetera, et cetera. But I kinda feel like, you know, this is one of the last ones before, like, the campaign comes.

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And, like, you guys have been on a real roll, but you also started, you know, with January 6th, right? Yeah. And the action literally was at the Capitol when you started.

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The action is gonna increasingly move to the presidential election, and that usually, I think, sucks a lot of the oxygen out of the room. And you're kind of not gonna be in that, right?

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Or, or you're just gonna try to be covering it from a congressional viewpoint? I mean, listen, I think in two and a half years we keep thinking there's gonna be a slow period, and there hasn't been.

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[laughs] So let's say we get through this debt limit, which I think we will.

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Like, if you listen, if anybody listens to, uh, the, the Daily Punch, which is our podcast, I've kind of been in your camp of, I mean, we pay attention to a lot, but I've been, like, I've been through the 2011...

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I mean, it's like we've seen- Yeah... this kind of before. But I think it depends on what happens with government funding.

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If they're gonna try to do 12 spending bills like they say they are now, that's a huge area of coverage for us. Yeah. FAA reau- the resoi- isation.

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Like, you have to remember there's things that our audience cares about- Okay... that maybe wouldn't be the front page of The New York Times, right?

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I always say, like, if we're writing the same story that Times or that the Post or the Journal or Politico even to some degree is writing, then, like, we've kind of lost our reason to exist. Okay.

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So the, the sausage factory keeps operating no matter [laughs] what. Exactly. Okay.

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And then I do think you will see, we did, you know, we had s- a, a product called The Tally, which was around the midterm election, that was all about kind of what was happening on the ground there, and I think you'll see that come back in a, in a big way in the sense of, like,

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where are the ad spending, you know, what are congressional leaders doing in terms of either endorsing Trump or not, or DeSantis.

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I mean, I think there's a huge congressional story of where money goes, as well as kind of who gets into what camp, who's going to visit, you know, is, is Biden going to these kind of key Senate Democratic states or not?

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I mean, those kinds of storylines are, there's a lot for us there.

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But I, yeah, I mean, there's no doubt that, you know, in, in '24 it'll be a different time, and I think, again, then there's a lot of preparation in terms of what's the next Washington like? Is there changes in power?

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And I think there's a lot for us to cover there as well. Yeah. How are you seeing increased competition in this area? Because, as I said before, you know, corporate affairs, what, what is, what is the title?

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What do, what do, what do you call it? You know the things where people are like, "Regulate us, but no, don't regulate us totally." [laughs] You mean government affairs? Is it government affairs? Corporate affairs?

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It's what I... I mean, that's usually what most offices in town are.

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Again, it's a nice area because it's, like, one of the areas of advertising where you're not only not competing with Google and Facebook, you're actually [laughs] taking their money oftentimes.

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It's like they, you can't, they can't compete for it. It's like, wow, shouldn't all advertising be like this? [laughs] If only.

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It's kind of, in some ways I'm reminded, it's much smaller, but the four-year consideration ads in Hollywood is another very lucrative...

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Jay, Jay Penske knows that this is a [laughs] very little lucrative area that he's, he's cornered to some degree. And this hasn't escaped others' attention.

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Obviously Politico, Axios, but now Semafor is, you know, they've really launched. To me, that's really the locus of the business. I would assume The Messenger wants it.

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I see, I talk with people who are starting different [clears throat] newsletters in this area. And it seems like there's a lot of people who wanna get at that trough. Yeah.

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Talk to me about, like, the increased competition that you're seeing. Yeah. I mean, it's really interesting. This is, Washington hasn't, you know, uh, uh, for a long time has been a super competitive space, right?

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Like, I remember being at Roll Call, and when Politico came in and we were like, "There's no way," you know? [laughs] And then the, kind of the pie got bigger. More newspapers- Exactly... at every office.

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[laughs] Exactly, right?

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And then I was at Politico for a long time, and we left, and I think we launched, and a lot of people were very skeptical that, not of us as, as the, the news was gonna be good, but that, like, there was gonna be a business model that would follow.

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I think that unlike Semafor or The Messenger, we are not trying to be aYou know, especially the messenger trying to get millions and millions and millions and millions of hits every day and kind of drive traffic and ads through that.

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And to some extent, I think Semafor has this kind of global lens with which it's trying to create a, a space. You know, I think for us,

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we are extremely focused, and I think we benefit from it because our audience, I think, trusts us in a way that they don't trust either the legacy media or some of these other players who haven't been part of the ecosystem for a long time.

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We just did an event, and a member of Congress said, "You know, I wake up and read you all because now I know... then I know what's actually gonna be happening," right? Right.

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I mean, I was like, "Can I record this, actually?" [laughs] This could be our advertisement. But like, this is the kind of... You just have a buy-in.

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And, and, and I would say the other thing that is a huge differentiator, and we s- we pay extremely close attention to it, which is we are read by just as many Republicans as we are Democrats.

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And that's a huge impact, especially as companies are, and advertisers are looking to make a bet about who's reading your content. So many legacy publications in the post-Trump and kind of through Trump world- Mm-hmm...

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you know, fair or not fair, I, I'm not saying that it is fair, but I think have been perceived by a lot on the right as being, you know, unfair and kind of in the bag for Democrats.

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And I think we benefit from the fact that, like, that just hasn't been our ethos. I think we call balls and strikes, and, you know, we have to face those people every single day up on the Hill.

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And when you do that, it's real- it's... You don't just kind of spout off for, for no reason at all. Yeah. So final thing is, is what's it been like being a journalist turned CEO?

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It's a totally different gig, [laughs] I'll tell you that much. [laughs] I think being a journalist is, is at least my career, has been very entrepreneurial. Yeah.

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So building a beat, building a source, taking on different products, particularly at Politico, I think was the training ground for a lot of what I do now. But, you know- Well, which parts? What, which parts of it?

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'Cause I do think there are some- some things that, that carry over. Yeah. Oh, in terms of carrying over in terms of journalism to entrepreneurship? Yeah.

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I mean, I think that a lot of reporting is charm, disarm, get people to tell you stuff that could get them fired, right? Mm-hmm.

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A lot of business is charm, understand their problems, and find a pathway for them to feel like you're gonna help them with their problems, right? And so in a lot of ways it's, it's pretty similar in terms of that.

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But I think in terms of leading an organization, you know, it's a... I mean, I'm, you know, had never looked at a P&L. I had... We have investors. We have, you know, I'm the fiduciary of our 401[k]. We have healthcare.

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We have, I mean, [laughs] there's just a lot of things that I feel like my kind of just whole focus has, has shifted a lot. But it's exciting, and I love the product part of it. I love coming up with products.

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I love thinking about what's the best way to launch things, really feeling like I f- I feel like I have a real sense of our audience in a way that that's really exciting, is the idea of being small and saying, "I have an idea.

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All right, is it a good idea? Then how do we get to yes in a pretty quick way?" Versus being in a larger organization, it's just much harder.

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You know, it's six months of meetings and middle management and people, and then ultimately, like, is it... Does it meet someone's KPIs or not? Like, we don't have to think about that. Yeah.

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But like, I mean, you talk about, like, being entrepreneurial, but then being a CEO is, like, different, right? Yeah.

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So, like, what, what's surprised you about that part, like, that's either, you know, been positive or like- Mm-hmm... wow, this is a lot harder [laughs] than I would've thought of? Motivating people.

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Like, I think I had always had a lot of- Yeah... dotted lines to people, but I think I enjoy the concept of, like, how do you get people to their best possible outcomes in terms of work, which is exciting.

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I think what's hard is when you go from four to 20 is I can't be making all of... You can't be doing all the things, and so learning how to delegate is, I think, crucial.

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And also understanding some things aren't gonna be done the way that you would necessarily do them, and that's also okay, you know? Yeah.

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But I think the best and the thing that I'm the most proud of, especially on the editorial side, is bringing in some of the folks that we've brought in, either, you know, you look at a Max Cohn who came in basically right out of college or Andrew Desiderio, who's come over from Politico and is, like, really creating this next generation of talent.

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You know, Jake and John and I have, like, we've... I've, I've done all the things that I need to do to, like, feel like I've been, you know, a, a star reporter. Mm-hmm.

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And so if we can instill in them and also elevate them, it's kind of exciting to, to be a part of. Yeah. And, and also building a brand that's beyond, like...

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You know, 'cause I think that a lot is made out of, like, quote-unquote, "personal brands" and stuff like that, and, you know, I think they can be a, a good impetus to, to building, you know, regular institutional brands.

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But, you know, having it tied to, like, a couple of individuals is, you know, it's risky. It is. Hopefully, I mean, the goal is we're building something much bigger though, right?

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And I think if you look at even just the, the, the branding of, of the colors and the events and the... that kind of stuff I also really like.

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Like, I think what we're trying to do is create something certainly bigger than, you know, the three of us plus Rachel Schindler, our other- Yeah... you know, co-founder. I mean, I think is, you know, this is...

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We're here to last. Like, this isn't just a let's try to have this as a vanity project, you know?

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I think we feel like we've kind of been able to build something really thoughtfully and hopefully are looking at the next, you know, three, five, 10 years about what that looks like. Okay.

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Well, let's come back in a year when you're ready to divulge the numbers- All the numbers. I'll be-... in the future. [laughs] I love it. All right, Anna. Thank you. Thank you so much. Really appreciate it.

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Thanks so much. Thanks so much for listening to this episode. I hope you enjoyed this conversation with Anna. This podcast was produced by Jay Sparks at Podhelpus. You too can get a podcast. Just visit podhelp.us.

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Again, we'll be back on Monday with a series of podcasts. It's gonna be Monday through Friday with these podcasts. By, by Friday, my voice is gonna be hoarse, and so the episodes will probably be shorter.

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But really looking forward to Cannes. Again, if you're going, please do join us. We've got three days of programming at the Curve Café, Monday through Wednesday from noon until three PM.

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We're also doing a cocktail party at the very same Curve Café on Monday between three and five. And we also have a cocktails and conversation event we are doing in partnership with Dotdash Meredith at their villa.

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The Rebooting does not have a villa this year, at least. That is on Thursday from four until six.

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I'm gonna be interviewing Neil Vogel, fellow Philadelphia sports fan, about, like, about all sorts of different topics, but in particular, I wanna hone in on AI and how it's not a threat to a business like Dotdash Meredith's.

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Anyway, it's gonna be a great conversation. I always like talking with Neil.

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So if you are going to Cannes, again, you can find out more information about all these events on therebooting.com, and I'll leave links in the show notes if you don't wanna go to the site.

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