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[upbeat music] Before we get to this week's episode, I wanna tell you about one of my favorite stories in media right now, and that's Just Women's Sports.

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They started simple, podcast, social clips, big mission, and then they started to realize something. If you don't own your audience, you don't own your growth.

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So they built their newsletter on Beehiiv, and it changed everything. Now, their newsletter is the hub that connects their podcast, website, and brand deals all in one place.

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It is proof that when you take control of your audience, you take control of your business. So if you are building anything in media, this is where you need to start.

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Beehiiv helps creators like Just Women's Sports turn attention into recurring revenue, and with their team of newsletter experts helping you handle switching platforms or creating something new, you can have your newsletter ready to go in days, not weeks.

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Learn more at beehiiv/enterprise. That's B-E-E-H-I-I-V.com/enterprise. Thanks a lot, Beehiiv. Welcome to The Rebooting show. I am Brian Morrissey.

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Uh, there is a fork in the road that every creator media business eventually reaches if they find traction, right? The early days, you know, are often powered by personal leverage.

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It can be one person with a clear point of view, a tight relationship with an audience, and a product that hits a nerve. That model works until it stops working or at least becomes a drag.

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You can see this split in the market. You know, some stay small by design. They continue to optimize the engine around the individual, and others follow what I think of as the Bari Weiss path. Yeah.

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They use a personal brand as leverage, and the ambition is to build a more of an institutional publication, but one that is rooted in the heat of a personal brand. This is a very difficult transition.

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It is not a clean one i-in most cases.

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You're basically trying to maintain this direct personal connection to the audience, while at the same time building the infrastructure required to make the brand bigger than, quote unquote, "just you."

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And there's, of course, always risk that the brand will end up becoming diluted, and I think that keeps a lot of creators from going down this path.

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Th-this is a big part of my conversation with Isaac Saul, who I've spoken to on this podcast before. I mean, Isaac began Tangle, which is a nonpartisan news site, back in twenty nineteen as a personal project.

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It was Isaac's voice. It was his structure. You know, it was born out of his commitment to viewpoint diversity.

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But one of the things that I, I, I, I found is that Isaac realized early on that while this enabled him to get traction, he needed to make sure that the Tangle brand was about more than just him.

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So we discussed that tension and how he's navigated using this nonpartisan approach to news to build a four-million-dollar-plus recurring revenue business with a dozen-person team, seventy thousand paying subscribers, and four hundred and fifty thousand overall email newsletter subscribers, and a half million monthly podcast downloads, and did all that without any funding.

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Completely bootstrapped. I really admire that. Really enjoyed this conversation with Isaac. I think he's very thoughtful about how he approaches building a media business, and hope you do too.

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So if you like this conversation, hope you do, leave us a rating and a review on Apple or Spotify or wherever you get your podcasts. And of course, send me your feedback. My email is brian@therebooting.com.

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Now here's my conversation with Isaac. [upbeat music] Isaac, it is great to have you back on the show.

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I think we talked a couple years ago, so I wanna u- I like to revisit these, you know, 'cause you were, you know, you were at a different point. I was... You know, at the time, you were a news...

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It was a newsletter, nonpartisan newsletter, you know, and you're still fighting the good fight, by the way, on X. You're like the last reasonable man left on X. [laughs] And I appreciate it. I don't even weigh in.

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I stay quiet. [chuckles] Thanks, man. Yeah. It's a bit of a cesspool over there.

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I mean, I started realizing that I'm mostly arguing with bots and people copying and pasting trashy clickbait- You're like, "But on the one hand, on the other hand," and like- Yeah. [chuckles]...

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I'm like, "Eh, I don't know if this is a place for you, Isaac." Yeah. But let's, let's...

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For those who didn't catch our first time in this, like, explain, uh, Tangle for, for the audience, because I think it's like, it's a really interesting property.

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There are some others who are, who have gotten into the space since then I wanna talk about, but, you know, we're at a time, obviously, where, where partisan news is, is what sells for all the different reasons, and you took a different path.

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Yeah. So I, I've, I... There are a lot of newcomers, new kids on the block- Yeah... I'd like to say.

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But yeah, I started Tangle in twenty nineteen, so six years ago, during the Democratic primaries in the lead up to the twenty twenty election when, when Biden was elected.

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And the, you know, the fundamental premise is really simple, like, we embrace viewpoint diversity. That's basically the whole ball game for us.

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So we tackle one big political debate that's happening in the news every day, and then we give you that summary of the story in the most neutral terms possible.

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We share a collection of perspectives from the left, we share a collection of perspectives from the right, and then somebody from the team, typically me, but now not always me, shares their own personal take, like a mini op-ed that kind of wraps up the newsletter and the podcast.

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And it's full of other, you know, little quick hits on the daily news and good news stories and re-answering reader questions and things like that.

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But that was the fundamental newsletter offering, which is still our core product. And as you kind of alluded to, I mean, since the last time we spoke, things have definitely evolved.

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I mean, A, the newsletter grew a ton. We have, you know, four hundred and fifty thousand people on our mailing list now. Wow. And B-W- as a larger audience came in, there was demand for new kinds of products.

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So, you know, we stood up a podcast, and then, you know, once we had the daily podcast, we started a talk show podcast, and then we stood up a YouTube channel.

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And now just recently, last week actually, we launched a texting service, which has been really interesting, an SMS service. I saw you experimenting with some subtext.

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Yeah, no, I'm gonna, yeah, like, when this comes out, I'll have... I'm doing, I'm doing a texting service- Yeah, yeah... with subtext.

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And, and I've been real- You know, we're only a couple of weeks into that, but, um- What, how are you using it?

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You know, w- I'm really, really dedicated to not using it as like, "Click this link and read this piece," or promote whatever. I mean, the, the, the reason that I- Twenty-five percent off. Yeah, exactly.

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Like, I've, I've subscribed to a few text services, only a handful, and I like them either 'cause they're like punch bowl news, breaking news stuff, or they are news outlets or independent influencers, whatever, who are just, like, almost using it like we used to use Twitter.

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They're, they, they use it as like a place to kind of experiment with some ideas and thoughts and get feedback. And so I've been trying to do that. I mean, we've been sending...

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You know, I, I'm, I feel the urge to tweet something, and instead of tweeting, I'll draft up a subtext and send it to the audience. And, like, you know, we've sent something two days ago.

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The, we probably have about 15,000 or 18,000 people, something in that range now on the, on the texting service, which is crazy.

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I mean, it took me two years to get that many people on my newsletter, so to collect those, that amount of phone numbers in a week is mind-boggling. Yeah. And you got all these phone numbers. Yeah.

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I, I don't know why, but I'm like, "I want phone numbers." Yeah. I, I'm, it's like I have no idea what the future of email or media holds, but I know people will have cell phones in 10 years. Yeah.

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This is like the newsletter, the newsletter people's, like, prepper sort of thing. Yeah. Yeah. [chuckles] It's like our prepper kit. It's totally true.

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And you know, we got, I got 4,000 responses to a text that we sent last week. Like, it's insane to me. People are enga- And they're really interesting. We're reading...

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There's something about that's so, it's like the inbox, it's so personal, so I, I'm really enjoying it so far. Yeah. I, I, I think so too. I just did, like, an experiment with it in Cannes.

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I just noticed, I, I, I'm not sure whether it was the novelty, I hope it's not the novelty, and, and we'll find out. I think it was easier around an event.

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But I, I do think that there's, there's something, it's, it is more personal place, and that's why it's like, "Oh no, people are gonna flood to this." But, but let's get in...

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'Cause it's really interesting to me because you really began this, it was kind of like a personal brand project in that, like, you were the brand, right?

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And I think there's a lot of people who have, you know, reached some kind of, like, creator market fit or something, [chuckles] and, and then they're faced with this, you know, a good dilemma, right?

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In that are they gonna continue f- to make it, you know, the, about them, or how do they expand, you know, beyond, you know, it, it being just them. And I, I always felt like you've been on that journey, right?

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Like, it's not just, like, Isaac now. Yeah. I mean, there are two things I think that have kind of made what's happened to me unique with regards to Tangle.

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I mean, the first one is, like, when I started Tangle, I was a nobody. So unlike a lot of what these creators are doing- You were somebody to someone... are like, you know, j- Well, you know, I was barely someone.

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But these journalists who are, like, l- leaving well-known publications- Yeah. Okay... and they have a huge following, and then they stand up a newsletter, everybody's like, "Wow, that looks so easy."

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Like, it's easy when you're famous already or you're really well-known already, but it's a lot harder when you're sort of making your way with the piece of content or with the idea that you're kind of executing.

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Like, I genuinely went from zero to 13 to 100 to 150 to 400. You know, like, I had those early days for the first year. So I think that is part of what made it unique.

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And then to your point, like, I recognized really early that it couldn't just be me, that, like, once I had the resources, I had to introduce some other personalities and some other people because, A, I would burn out, and B, you know, like, I don't want this to be the only thing I ever do.

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Like, I would love at some point to take a little bit more of a backseat role or, you know, go write a book or whatever. Like, do stuff that will require me not being locked in 12 hours a day every day.

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And so when we started getting the growth that

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I wanted to see and bringing in new writers and whatever, I, I was really intentional about giving them some platform and making sure that, like, we were developing a few different voices or personalities.

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You know, we're doing that on our podcast, we do it in the newsletter.

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Just today as, uh, you know, an hour before we hopped on this recording, I published a piece from a staff writer who just wrote a story criticizing something, an essay criticizing something I wrote last week.

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And, like, I'm introducing her to the audience as, like, "This is Audrey.

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Here are some of her views," and she gets to pen this essay, like, you know, taking a shot at the founder of this news company, which is a really cool thing, I think, and pretty unique.

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So, you know, I'm trying to do more of that to get the audience used to seeing people that aren't me. 'Cause I am, I don't want it to be the Isaac show. Like, I'm worried about that.

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It, I think it's bad business strategy, and it's not sustainable in terms of, like, the scale that we hope to get to. Yeah. So tell me about the scale you want to get to.

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'Cause I think this is, like, something, again, good problems to have, but you get traction, you know, particularly with recurring revenue because, you know, recurring revenue, I think the last time we talked, it was almost all of your revenue.

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I know you have advertising now, but recurring revenue as a base gives you a lot of optionality, right? So tell me about, like, what the ambitions are now for, for what you ti- want Tangle to become. Yeah.

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I mean, I have, I have a kind of theory of the case that I'm, I'm sort of just starting to turn over in my head and play with a little bit, and we just had a big team retreat in Vermont where I kind of articulated this to everybody, and I think it looks a little something like this, which isEverybody in the media space is kind of bundling and adding.

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That seems to just be the m- where the momentum is right now. Like, we're seeing media properties get bought up, you know, and like maybe the Free Press type, type style, but- Mm-hmm... in a smaller way.

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Or we're seeing this sort of puck, like find people who are doing really good work and bring them into your umbrella and like, you know, s- the Argument just launched on Substack with all these different writers who are kinda like contributors, but also part owners, and there's like...

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I'm, I'm not totally sure how that structure works, but there, there's just a lot of bundling happening, and with the bundling always seems to come this like, here's more content, new podcast, new newsletter.

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I am sort of... Like, my mindset is that I think we're about to hit a point where people want less, if we're not already there right now.

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And I actually don't think it's like a super smart strategy for us to roll out like, you know, different offshoots of Tangle in this moment, and all these little different newsletters and, you know, new podcast shows or whatever.

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I have like news outlets I'm a huge fan of, or personalities I'm a huge fan of.

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When I get like those emails or the promotions for new stuff, a new show they've launched, a new newsletter, like my initial reaction is just like, "Oh my God, I have so much already."

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Like, I love what you guys are doing- Yeah... but I can't subscribe to another newsletter. I can't subscribe to another podcast.

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And I think that audience fatigue, it's showing up in the numbers, in the open rates, like for us across the industry, website traffic.

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So I'm thinking about ways to actually create a little bit of scarcity of content and like- Mm...

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desire from audiences for more, which like, you know, we're kicking around a few ideas, like maybe doing one fewer newsletter a week or something like that, that gives us kind of a break in the middle of the week and gives us a little more time to work on some of the premium content and just make it better basically overall.

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Or like maybe in the middle of the week we publish a reader essay every week or something our audience contributes to us, so it just takes kind of like a work day off our plate and gives everybody like a moment to breathe.

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Yeah. Something like that that's just like a change of pace and not hitting people with the same thing over and over again back to back, back to back. I mean, you've, you've expanded into a lot of things.

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Like you're now, like you, you... Like when we first talked, you didn't have podcasts. You got podcasts. Right. You've got... You're doing YouTube.

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You got the, you got the YouTube thumbnail game going now too- [laughs]... I noticed. Like, you know, you got the surprise guy face and whatnot. You're doing the texting service.

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I don't know, you haven't gotten into events yet, have you? We, we've had a few events ever since we were, I mean, 2023. I think we've done three, four now. And like, you know, we're talking about it.

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I think it'd be stupid not to talk about it, like what could we stand up? Yeah.

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But it's another thing where it's like, again, you know, this isn't like my official position quite yet, but it's sort of this idea that I'm wrestling with that like- And I get it...

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maybe the more isn't actually the answer. Right.

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But the, here's, here's the point I was, I was sort of setting up was that I've always felt like there, there's periods of expansion and then there's periods of, you know, where you need to consolidate the gains.

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Like in that, like you, you need to... You end up having these periods where you, you roll out like new things, and then you have to have periods where, you know, you digest and you make them like better.

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Because I think the, the risk is always, you know, it's like the old saying, it's like if you wait for things to be perfect, like you'll be waiting forever. Right. [laughs] And so you have to like...

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And, and we were talking about this before. Like I think, you know, we probably both feel this way. It's like we gotta be doing more.

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We gotta do m- Now there's these other things that are going on, and you, you want the momentum, but at the same time, you know, you wanna take a step back and probably also just coming from, you know, journalism background, you wanna do better, right?

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Like, not just like more. Yeah. Usually the business side people are telling you to do more. I mean, I... And I, and I think about that. Yeah, I mean, I think about that in my day-to-day, just, you know...

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I, I put this to my team, like as a thought experiment, what would it look like if we just published one newsletter a week? Like, how would we monetize it? What, what would the content look like?

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What direction would we go? Like, just, just to like think it through and like we're not gonna do that. We can't do that. We want the audience habit, whatever.

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But like, you know, what, what sort of doors would having four days a week, Monday through Friday, open for us? And a lot of the answers were like, "Oh, we could do more long form journalism.

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We could like really edit a piece for three days in a row and get opportunities to like, you know, stress test it more versus this like insane publishing schedule we have now where we're like turning stuff around in 24 hours.

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Do more exclusive interviews, sell more premium ads," things like that. I'm like, okay, so like I love that. These are all great. Like I think we should do all those things. We want more premium content.

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We want more time with the pieces we're publishing.

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Like how do we free up the team we have to do that or like take a step towards that without, you know, crushing this awesome audience habit we've made where people are sitting around at 12:00 PM Eastern waiting for our newsletter to come out every day.

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So like to, to answer your question, the original question about like scale, goals long-term, I mean, for me, I, we, we've doubled the size of our team in the last year, so we have 12, 12 full-time employees now.

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Oh, wow. Yeah, and I, I really wanna see what I can do with this group. So like for the most part, I'm...

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Th- maybe there's a chance like on the video side, we, we have another hire pretty soon, but I think like generally speaking, I wanna kinda press pause there and just like see what this group can do over the next year.

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And I am like way more interested in scaling our audience than I am scaling our team. Like I don't wanna have a 200-person newsroom. I have no interest in building the next CNN or Fox News or whatever. Yeah.

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I, I want like a small, nimble team where we have tons of revenue per employee and everybody's paid really well, and we have a bunch of dogs, like the best of the best we can find in the industry.

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And we have- That's D-A-W-G-S, right? Yeah, D-A-W-G, yeah. Okay. And we have a bunch of, you know, a, a huge audience. Like i- the dream for me, you know, now after we get...

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I mean, I could've never dreamt of 400,000 subscribers or whatever, but now that I'm here, it's like I want five million, you know?

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I, I wanna be in a place where-People are waiting for our take or our newsletter to come out, and it has a meaningful impact on the dialogue and, and, and makes some waves, you know?

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Like, I'm, I'm jealous of the sort of, I, I guess, influence that places like The Dispatch or the Free Press have that aren't much bigger than us, yet I feel like their brand is more well-known and the- Yeah...

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the sort of impact them publishing something is, has is bigger and, and, like, I want to get us to that point to be- Well, they also have, like-... kind of movement players... insider brand name people. I feel...

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Don't, don't take it the wrong way. No, no. 100%. But, like, you know, that's their, that's their model- Yes... is more, like, inside Washington, you know, Jonah and- Absolutely... and Steve.

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And so yeah, so I, I wonder if that it just makes it... I don't know. That probably ends up helping. I mean, the... You are probably. How many, how many paying subscribers do you have? We have over 70,000 now.

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Okay, so yeah. Like, you're... That, that's the thing. It's like, I think people probably think, uh, of The Dispatch and them, like, as being, you know, far bigger. But, like- Right... that's not the case. They're not.

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And that, and that's sort of like, somebody said something to our COO at a newsletter conference, something like, "You're, like, the biggest newsletter nobody knows about." And I was like, "Ah, shit."

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Like, she's- No, that's a good thing... that's kind of true. Yeah, yeah. It's like- It's better, it's better. I, I used to ride my bike around Miami and see, and see, like, Azi ads on, on the buses. So [laughs] Oh, God.

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[laughs] Like... Yeah. Yeah, no. I mean, it's... So it's, it's something that, like, I'm thinking about is just... A- and to your point, like, I think that Dispatch Free Press model is really good.

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It's why it's effective. And maybe long-term, like, bringing in those kinds of contributors, even if they're not full-time staffers, is, like, a way to sort of raise the profile.

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But I also just think it's like we have to raise awareness about what we're doing.

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Like, when we get people in the door, w- we're really good at turning them into loyal readers who love our work and are curious to hear where we land- Mm...

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on stuff, 'cause I think we're doing s- I think the product's really good. I think it's fair, and it's honest, and transparent, and it's human, and people like those elements of it.

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But, like, the perpetual battle for me has been, like, making it kind of a mainstream household-type name without, you know, the splashy hires or y- the, the big acquisitions or whatever else. Yeah.

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So you've kept this, like, incredible conversion rate. 'Cause I mean, when we, when we talked before- Yeah... you know, you had, like, a, like, a, a 16%, I think it was, like, conversion rate.

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And I was like, "Wow, that's, like, really impressive." I mean- Yeah, I think it's gone up, actually. I think it's a little over 17% now. Yeah. So what is the... I don't know, what's the secret other than being amazing?

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Like, what is, uh- [laughs] Yeah... are you underpriced? Like, what's going on here? [laughs] Yeah. I mean- This is very suspicious. I ask, I- It's like, you know, like Europeans?

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Like, Eur- Europeans when they- [laughs]... when someone is, like, a, is a philanthropist, they look at it very suspiciously [laughs] I think. Yeah. Yeah. I mean- They're like, "What are you hiding?" [laughs] Yeah.

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I ask... I, I've asked the pricing question. I mean, we were initially five bucks a month, $50 a year as the main offering, and we bumped that up to $59 a year, six bucks a month.

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And we also now have a bundle which is 99 bucks a year, which gets you, like, ad-free podcasts and the premium podcast content too.

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And then we have this thank you tier, which is basically $199 a year, and you don't get a whole ton other than some sorta insidery business updates.

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And it's framed as, like, this is just a way to, like, throw some extra support behind our work. And quite a few people take that. I haven't looked at the numbers recently, but it's a couple thousand or something.

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That's great. Yeah, so I, I think it's two things. I think the reason we're really good at it is twofold. One is we have really good premium content, and we always send previews of it to people.

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I used to be really scared. I used to send maybe one paywalled Friday edition out to our whole mailing list, where they'd run into a paywall in the email, like a month. Yeah.

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Because I, I'd see the 50 emails come in, pissed off about the paywall, and it s- Right... it, like, scared me. And then we did an experiment where we just sent the paywall every Friday.

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And, you know, you can get the angry emails, but if you look at the actual people leaving the free mailing list, it would be, like, a couple hundred each time we sent it. But we would get two, three- Yeah...

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four, 500 paid subscribers. So I'm like, "Oh, this is, like, a really easy calculation. We need to be showing-" Yeah "... like, people this paid work." I feel like the journalist in you probably works against you there.

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Yeah. Yeah. [laughs] Because, like, the business type person's like, they don't care. They're like, "I don't know. Whatever." Yeah, exactly. I mean, it's like- You'll always get people who complain. [laughs] It's...

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Yeah. I'm... I... And it's the same way we ended up doing advertisements was I had this, like, high-minded- Yeah... sort of journalistic integrity view. Like, "We'll, we'll always be independent. We'll never do ads."

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And then I asked our audience, and it was, like, 95% of them were like, "No, you should do ads. Make as much money as possible." And I was like- [laughs]... "Oh, I'm, like, a total fucking idiot.

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Like, why didn't I do this?" [laughs] So yeah. I mean, the, the... So that's one, is I think...

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I just think the content's good, and we're sending people articles they wanna read, and the free list is getting these sort of, like, generous previews with strategically placed paywalls.

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And then the second thing is I, I, I think I have a really good upsell email that I send every one to two months to the entire free mailing list.

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And I don't know why more people don't do this, and I'm, you know, I'm, I'm almost hesitant to just, like, give it away for free.

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But I think I've already talked about it on a few podcasts, but it's just being really direct with people. Like, the subject line of the email literally says, "Yes, I'm asking for your money."

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And the opening paragraph of the email is like, "I know many news organizations send you these kinds of emails in, like, a clickbait, concili- like, concealed fashion. But I'm gonna be really direct with you.

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I'm about to ask you to subscribe to Tangle. If you love our work and wanna support us, you can just subscribe here. You don't have to read any further. If you need some convincing, here's my argument."

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And then I frame it in, like, very human terms, not like, "Oh, what are we gonna do with all your money?" And I'm like, "Here's what you get.

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Like, here are the really awesome additions you get when you subscribe."And also, like, here's how much money we made last year compared to what Sean Hannity and Rachel Maddow make.

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And if you want journalism like this to compete with the big news organizations, like, we need more revenue, and 90% of our revenue comes from subscriptions, or now it's, like, 80, 85% with the ads we have. So subscribe.

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And people respond really well to that. I mean, I-- we just sent one of those emails maybe two months ago to, like, 300,000 people, and we got almost 1,000 paid subscribers out of it in one email blast.

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And, like, on the one hand, it's like, oh, one in 300, that kind of sucks.

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But on the other hand, it's like $1,000 at 59 bucks a year is we just added $59,000 to our annual recurring revenue, which is- Yeah, that's, that's a great email to hit send on. Yeah. [laughs] Yeah, totally.

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That's a success. You don't need to- Yeah... like, do, to do too much econom-ec- econometric analysis there because of the LTV off that is, like, even, even, like, higher, so...

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And I think it's interesting 'cause it's, it's, like, not r- but it's like you put it in human terms, right? Yeah.

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Like, 'cause I always think with a lot of these upsell emails, like, they're clearly done from the marketing department, and that's fine. But the really good ones, like, you know, Defector does really good.

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You know, they have their... You know, and it's in their style, right? Because- There's personality, yeah. Yeah. And it, and it's, it's, you know, it's organic, for lack of a better word.

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But I think a lot of times, you know, people overthink it. So tell me about the expansion into, like, to be multimodal. Like [chuckles] you know, to go into video and podcasts.

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Because, like, I've always been a little bit skeptical of, quote unquote, "newsletter businesses."

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I think you can make it work, but I think if you're gonna build a real sustainable media business, you need to, you need, you need a foot in a, in a few different areas. Yeah. I mean, I...

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First of all, I'll say upfront, I was really nervous about it. I mean, I think most media organizations I've seen fail have failed because they chase the new shiny object- Yeah...

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and they get distracted by something, and they stop doing what they're really good at.

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We're really good at sending a good newsletter, and, like, I, I beat this into my team all the time, like, this is the engine that drives everything. And whatever we do, we can't sacrifice, like, the attention- Yeah...

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that this product gets. That being said, the p- the podcast was first, and it came almost entirely out of reader demand.

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We just had so many emails a week of people saying, like, "Hey, I love this newsletter, but I don't have time to sit down and read it for 15 minutes.

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I wish I could just listen while I did the dishes or drove to work or whatever. Like, I would totally listen to a podcast if you guys had it."

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And so we started that, the podcast, and we got enough listenership on it that I was able to hire an editor and monetize it with programmatic ads and basically break even out of the gate.

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And so from a business perspective, it was pretty low risk in the early days. Today, we get something...

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I mean, we, since we produce six podcasts a week now, I mean, we're, we're turning basically every newsletter into some kind of podcast content.

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We, we get a half million downloads in a month, which when you monetize just on the ad side, can turn in anywhere from, like, 250 to 3 or $400,000 a year in ad revenue, plus the people who subscribe to a membership to get ad-free podcasts and unlock the premium stuff.

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So, you know, that's enough to hire a couple editors and also make a good profit off the podcast. And that's what we've done.

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Like, it's not, you know, the, the memberships that we have through the newsletter are generating, like, $4 million a year in recurring revenue.

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So that compared to maybe $300,000 or $400,000 from the podcast, it's like, it's obvious where the main engine is, but it's a nice little revenue bump. It gives us additional- Okay...

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you know, a- and, and we get to meet people where they're at. I mean, the truth is there are a lot, especially younger audiences, are way, way, way more keen to subscribe to a new podcast than they are to- Yeah...

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open an email every morning. I mean, I'm sure you worry about it. I worry about those, like, email fatigue. I know, like, they keep saying, like, "Oh, no, no email. Peak email's been predicted forever."

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I'm like, "I don't know." Yeah. [laughs] There's a lot of email. I'm [chuckles] I'm beginning to, like, worry about that. Yeah. We're, we're... It's a, it, it, it is, like, so saturated. My inbox is a total mess.

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Even my most curated inbox, which is my work email, I'm just marking, like, 300 emails as read every day- Yeah... 'cause I'm like, "I'm never gonna get to this stuff."

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And I think, like, podcasts are like, they're interesting because they're... Obviously, this is a podcast, you know, I have to talk about podcasts. But a lot of it is ambient, you know?

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And I think in some ways, like, we're sort of, you know, drilled into this like, "Oh, we gotta get people full attention, engagement and stuff."

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There's actually a lot of power to ambient in that I've noticed that when people always ask, tell me what they're doing while they're listening, you know? Which in some ways- Yeah...

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I'm like, they're distract- But then you become, like, attached to, I don't know, dog walking or like [laughs] Yeah... something else in their lives. It's a habit. It, it creates, like, a habit. I mean, I, I do the same.

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Like, every morning when I walk to work, I have a 20-minute walk to work.

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I open up The New York Times and, daily, and I listen to the daily podcast 'cause I'm, like, curious what The Times is framing as the story of the day and how they're covering it, and it's almost exactly 20, 25 minutes every day.

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So it's like the perfectly timed show, and, and that just becomes- Yeah... part of my routine. The YouTube stuff is different, I would say. Like, A, we haven't quite cracked the code yet. We haven't monetized it.

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B, it's m- our motivation is almost entirely out of capturing a different audience. I mean, our, our newsletter audience is a little bit older. The podcast audience is kinda all over the place.

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The YouTube audience, I think, is, A, younger, and B, from a political perspective, there's just, like, way more kind of heterodox independent stuff happening in the YouTube space in the political world.

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For good and bad, I gotta say. Yeah, for good. Yeah, yeah, no kidding. But we wanna get those peopleYou know, i-in the door. I've never been, like, a video guy.

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I mean, I've done, throughout my career as a journalist, I've done tons of on-camera stuff, but I've never, like, run a video operation or, like- Yeah... you know, figured out how to make that side of the business work.

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So right now it's mostly an expense, and we hope that it's a top funnel eventually. You know, we're, we're really close to standing up our podcast in video format, which everybody's doing now.

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But I do think it works, like clipping the podcast and getting it up on YouTube- Yeah... or having full, full videos up there. So that, that's the goal long term.

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So you mentioned, like, four million in ARR, so that would put you at, at, like, five million in revenue. Yeah, a little shy of that total. Okay. Yeah. Good. I mean, that's a good...

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And you're nicely profitable, I assume, with, with, with 12 people. Yeah, I'm, we're, we're really pro- I mean, our margins are, like, 30% or something- Yeah... or they were in 2024.

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I mean, we'll see how it comes out with the expansion of the team and everything. But yeah, we've had, we had phenomenal growth around the election last year. Yeah. So how do you end up thinking about, like, resilience?

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Like, you know, because, like, I did a podcast, like, the other week with, with Josh Marshall from Talking Points Memo.

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Man, I'm, like, very impressed by anyone, like, who's, who's kept at it for 25 years and has come acro- come through multiple, like- Yeah. [laughs]...

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you know, periods of, of upheaval and, you know, to made it to the end. I don't know if you think about building for resilience and, and longevity really. Yeah, I-- for sure.

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I mean, look, I think one of the things- 'Cause I think you have the luxury of doing that now, right? Like, I think when you're in the... Probably the last time we were talking, you know, I didn't know it.

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Like, I'm still in that. It's like, it- things are more precarious. I don't know. Or maybe they just... Do they still feel precarious to you?

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I think I definitely have a little bit of imposter syndrome on, like, the, you know, the success part of it, where it's like I, I also candidly grew up kind of financially insecure, and so I'm just, like, always sort of stashing money under the bed- [laughs]...

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like, worried about what the future could be.

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And I do think, I, I will say a-actually, part of the resilience for me is, like, w-when we have months where we're just, like, really crushing it and s- there's tons of growth, and the growth of the subscriptions are outpacing the team, like, I am putting money, like...

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We have a rainy day slush fund because I know, I've been in the media world long enough to know- Yeah... that, like, those days come.

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So, you know, we have a year of runway if, like, our revenue stopped, you know, Stripe- Right... does something insane and all of a sudden a-all our subscriptions disappear.

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Like, that-- so that's part of the resilience to me. And the other side is, I mean, it, it's, A, making sure you own 100% of your audience, like, that mailing list, the texting service.

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Having ways to contact your readers across multiple platforms is really, really important.

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We have a big Instagram following too, which has been really helpful as kind of like a top funnel and also communicating with readers.

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And B, the obvious one is just, like, starting to diversify the revenue, which we've done a little bit with the podcast, and we've done a little bit with the ads that exist in the newsletter.

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But I am thinking about, like, you know, what, what does that look like to not be solely reliant on the membership revenue, or what would happen if our membership revenue halved for some reason, or, you know, whatever else.

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I don't have a great answer for that right now, but I think it probably looks like, you know, a successful YouTube channel or podcast with really, with really premium host-read ads.

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It probably looks like another kind of premium-type revenue stream, like events or, like- Yeah... the texting service actually being paid or something like that. But I don't know.

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I mean, it's, it's really hard to do what Josh did. I mean, I share your admiration. Like, it's crazy to me that he's still going.

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So how do you end up thinking about, like, w- like, when, when you talk about diversifying revenue, it's interesting because, like, you're in a great position.

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Like, you- if you wanna diversify revenue, diversifying it from, you know, 80% plus ARR is, is the [laughs] is where you wanna diversify. Yeah.

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Most people in media are in the other part, where they're, they're, they're stuck in the, the, the ads treadmill, particularly, you know, it's get the traffic and then get the, you know, the programmatic going, and that, that is very precarious m- versus, versus diversifying from a subscription base.

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What have you found? 'Cause you were early on the, the s- the advertising road when we had spoken a couple years ago. What have you found with that? Like, I mean, it's a different, it's a different business line.

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It can be very frustrating. You're not in a category that, like, is, is, has a bunch of endemic advertisers. Yeah. I mean, I would say all the things you just said. It's very [laughs] frustrating. It's less predictable.

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Yeah, I've been reminded of all the reasons I focused on memberships in the beginning.

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You know, like, our sales team will come to me and say, "Hey, we, we have X amount of sales this month, and, like, this is the biggest month we've ever had." And I'm like, "Oh my God, amazing." Like, up and to the right.

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Yeah, yeah, yeah. We just, like, we're gonna quadruple our ARR. Fill right on XL. Yeah. This is gonna be massive. Yeah, and then, like, the next- Yeah...

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month we're back to where we were 12 months ago, and I'm just like, "How did this happen?" And they're just like, "I have no idea. Things just dri-" Like, the headwinds are unpredictable.

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I, I, I literally can't imagine running a business, what it would be like to run this business entirely on aver- It's just so much less predictable and less reliable.

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So, you know, we do internally, we have all sorts of projections and budgeting, and what I ultimately decided was we do literally all of that without taking the ad revenue into account. And then when that money- Yeah...

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comes in, it's like this huge bonus and cushion for some rounding error we made or, like, a budget that went over or whatever. We're like, "All right, it's not a big stress.

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We have this, you know, 200 grand of ad revenue from last year," or whatever.

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But I lit- I literally just don't include it in the budget because I find it so precarious and hard to predict in, like, a forward-looking sense. It's, it feels, like, nonsensical to me to do that. Yeah.

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So finally, it's just in-In your lens on this, because it's like saying, it's like a very practical... Like, I like it because it's like it's very practical.

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It's like, "Here's what the left's saying, here's what the right's saying." [laughs] "Here's the..." And, you know, and we've gone through a period where, you know, that is a...

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It's, there's a market for it, but sometimes I wonder about how large the market can be for, for that, for that kind of approach because we're in a very tribal era, and it seems like we're almost, like, losing...

230
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We all have our different versions of reality, it seems like now. Yeah. [laughs] It's like I'm starting to wonder what is, like, real.

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Like, I was, I was at dinner with, like, a family member, you know, very, you know, well educated, he runs a company and everything, and he was just like, "Well, these protesters are getting paid anyway.

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I mean, that's why they're out there." I'm like, "Are they?" I was like, "Uh, really?" Yeah, right. I'm like, "I don't... Like, I didn't, I didn't know that," and I didn't think... I'm like, "How would that even work?"

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Like, I mean, the, the, the W-9s? Like, I don't know. I don't even understand that. How do you... Give me the case that this is a growth market. Yeah, sure.

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First of all, it's something we ask our- First of all, were they paid? Are they paid? Yeah. [laughs] No, no, I don't think most of the, the No Kings protesters were paid. Okay. Um, maybe there were some.

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I, I'm sure you could find some organization that offered a few bucks to get people out there, but- Yeah... I know plenty of unpaid family members who attended, I'll put it that way.

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F- first of all, it's a question we ask ourselves all the time, like, you know, when our mailing list is stagnant for a week, it doesn't seem to grow.

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And then the thing that we see is, like, what's actually happening is there are a lot of people unsubscribing or leaving because of news fatigue, and, like, w- we've pretty consistently always been able to bring in new and new members.

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It's just sometimes they don't outpace the amount of people who are like, "I need a break from the news." Which, by the way, when we survey people, unsubscribe is now the number one reason for unsubscribing.

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It used to be accusations that we were biased left or right, but now it's- Hmm... I just need a break from the news. So, um- But wait, do you offer, like, take a break?

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We, we have a way to turn off the weekly and keep on the once-a-week Sunday roundups- Okay... which a lot of people take. That mailing list is now almost 50,000 bigger than the daily. So that's working.

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You should, you should start, like, a little, like, shoulder business with, like, the, just as, like, like, puppy photos or something, and be like, "I need a break." Yeah.

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[laughs] And then we're just gonna send you, like, dog of the day. Funnel... Yeah, funnel all the unsubscribes into that. That's a good idea. So I mean, look, m- the...

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I guess the direct way to answer the question is independence, self-described independents in America politically are now the number one group.

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They're larger than conservatives and liberals, which hasn't always been true. Not everybody who self-identifies as independent is actually independent. A lot of them- Yeah...

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vote typically one way or the other, of course. But that is, you know, 40% of the country who thinks of themselves as being independent-minded enough to engage with the kinds of content that we offer.

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I, I, I definitely don't think 450,000 is the ceiling for us. I, I, I don't think it's 40 million either, but I think it's probably somewhere in that sort of, like, seven, mid seven-figure mailing list size.

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Like, I, I genuinely believe that we could get to three, four, five, six, seven million people on this mailing list, and that's just because, not, not just because of the product and the political bipartisanship- Hmm...

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and whatever, but just because, like, of email is not gonna be something that's a fit for everybody. I think YouTube and podcasts could be equally as big- Yeah... if we played it right.

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But your thing is, like, you guys are for independents, r- not centrists. Right, exactly.

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Right, that, and that is different, 'cause I think a lot of times people, like, confuse the two, or they can meld the two, where centrists- They, we, they confuse it all the time.

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[laughs] You know, centrists are trying to find, like, a path that's really difficult sometimes. And we're not saying that. We're, we're saying viewpoint diversity. Yeah.

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It's sort of like this is the, the free market of ideas. It's that kind of ethos, I think, which, you know, a- appeals to, I think- Right... m- most often the kind of independent-minded voter.

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Well, because the chances are, like, everyone eats at the ideological buffet to some degree. Right. Right? Like, I mean, the idea that, like, some political grouping could, like, literally every single possible topic.

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Like, what are the chances that me and, like, Nancy Pelosi would agree on every single thing? [laughs] Right. It just seems unlikely to me. [laughs] Yeah, 100%.

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And I mean, the, the exercise I give readers often is, like, the really partisan ones who come in, is, you know, what are the odds that the Democratic Party's right about everything?

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Like, how can you just live in that delusion? It's, it's a total fantasy that one side would be right on every issue.

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And, like, our proposition is, over time, if we show you a bunch of different arguments from across the political spectrum on all these issues, you'll realize that there's, like, a lot to learn, and there's a lot of nuance- Yeah...

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and the really big debates that are happening. I always end up asking, I'm like, "What was Trump right about?" Yeah. [laughs] And if you can't name one thing, then I'm like, "Okay, you're not, like- Yeah, that's it.

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Yeah... you're not really thinking too hard." [laughs] Because you can't... If you can't name one thing, like, that's tough. Awesome. Yeah. Isaac, thank you for doing this. I really appreciate it.

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It was great to catch up. Of course. Thanks for having me, Brian. Huge fan, and appreciate you coming on. [outro music]