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[upbeat music] Wow, we're breaking news here. Here we go. [laughs] Oh, yeah, yeah. I mean, it, you know, [beep] did that trick where it was like, "Oh-" Tell me how you do everything. Yeah.

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[laughs] I- And I kinda, you know, busted his balls a little bit. Like, maybe, maybe I don't wanna put this on the podcast.

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[upbeat music] Before we get to this week's episode, I wanna remind you of another podcast I'm hosting.

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It's called The People vs. Algorithms podcast, and it's a show about detecting patterns in media, technology, and culture.

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Each week, I am joined by Troy Young, former Hearst Magazines executive, who also writes the People vs. Algorithms newsletter, and Alex Schleifer of Universal Entities.

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This week we discussed how we're living in a transitional era, as well as my own theory about how Silicon Valley is breaking up with the ad industry. You should check out the show. Just look for it on Apple or Spotify.

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So just search for People vs. Algorithms. As Americans go to the polls today for the midterm elections, it's safe to say American politics have never been more divided and divisive, at least in modern times.

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[upbeat music] Conservatives do not trust anything in The New York Times. Progressives do not trust anything from Fox News. Nuance has seemingly been completely lost in the never-ending flame wars that we endure.

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The old struggle to be fair and balanced has given way to preaching to the choir.

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This is something that Isaac saw firsthand as a political journalist at outlets like Huffington Post, where what he wrote would end up being distrusted based on the place it appeared rather than the substance of the story.

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Three years ago, Isaac started Tangle, a newsletter, with the idea that he was gonna present both sides to news stories, as well as his, as, as his own take on them, and that he would find a wide group of people who wanted to hear both sides of issues.

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And that's proven mostly true. Today, Tangle has 8,000 paying subscribers and nearly 70,000 free email subscribers.

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It is currently launching a new ad program to complement the nearly $30,000 in recurring revenue it takes in from its subscriptions.

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Isaac and I discuss the origins of Tangle, his move away from Substack to build his own platform, and his experience in building an independent media business. I hope you enjoy the episode.

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Please do send me your feedback. My email is bmarizy@gmail.com. Big thanks to Jay Sparks of Pob, Podhelpus for producing this podcast. If you are in the market for a podcast of your own, please get in touch with Jay.

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Visit podhelpus at podhelp.us. [upbeat music] Isaac, thanks so, thanks so much for joining me for the podcast. Thank you for having me on. I'm, uh, I'm a big fan of the, the Rebooting newsletter, so it's good to be here.

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Okay, thank you [laughs]. I'm gonna put that on my sales kit. [laughs] I tell that to everyone. So you're, you're three years in and a little bit now.

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First, for those who don't know Tangle, for instance, what, what was the, what was the opportunity that you saw, and what sort of led you to, to create it? And what is it? Yeah, sure.

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So, you know, our, our tagline is that we're a, a nonpartisan subscriber-supported politics newsletter.

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Uh, the general gist of it is that every day we, we try and tackle one big debate that's happening in the political world.

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And I sort of give a breakdown in the most neutral language possible of what the story is, and then I give three takes from the right and three takes from the left, and then I offer my own opinion about it.

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So I go out into the opinion-making machine, the columnists, the podcast hosts, the television hosts, and I try and pull three arguments from each side, from, you know, across the spectrum of the right and the left, and then sorta get them down into some digestible bites and give them to people.

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So theoretically, if you read Tangle, you are getting, I think, the most holistic look on political news that you possibly can anywhere in the space right now.

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And, you know, I, [clears throat] I started it for a few reasons. I mean, two, two big ones.

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One was that as a political reporter and someone who wrote political columns sometimes, I realized that people were ignoring my work based almost entirely on where it was published.

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Uh, so, you know, if I wrote something very critical of the Democratic Party in Fox News, uh, basically nobody who I wanted to hear what I was saying cared because Democrats don't read Fox News.

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And the same is true of, you know, Huffington Post criticizing Republicans, whatever. That was, like, the big... This... I saw the silo, I think, a little early back in the 2014, 2015 days.

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Now everybody knows that we're all living in our own social media bubbles and our curated newsfeeds. That's kinda common knowledge now.

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But, you know, eight or nine years ago I don't think a lot of people were seeing that clearly.

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And, and then the second thing was I am pretty politically incongruent, and I try and go, you know, understand as a politics reporter what's happening in the world.

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And in order to get a balanced view of any single story, I would have to read 10 publications that have clear, diametrically opposed, you know, political leanings. So I, I can't just read The New York Times.

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I have to read The New York Times news section and then go read The Wall Street Journal if I really wanna get this full picture. And so I was like, "There have to be other people like me out there."

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And I figured if I could put all that stuff in one place, a lot of sort of politically open-minded people- Yeah... would read it.

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So it was just sort of a gut feel that you thought that there was a market for this, right? Because, I mean, like, all the evidence I would think- [laughs]...

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if we were to, like, do this McKinsey style, I don't know if we would come up with the conclusion three years ago that there was much of a market for neutrality in, in anything.

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'Cause just the way we live now societally, it seems like, you know, th- society has changed to some degree. I, I, I would say I had two big... things on my side.

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The first one is that independents are the largest voting bloc when you ask people to self-identify in the United States Yeah I think in September it was something like 43% independent, 30% Republican, and 24% Democrat is how Americans are self-identifying right now.

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So I had that going for me. Obviously, there's a ton of research out there that people who say they're independent aren't actually independent, but they're at least saying that.

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You know, they're trying to stake out this middle ground.

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And then the second thing was, you know, I read a lot of business news, and I'm signed up for other newsletters and stuff, and it is the classic, you know, independent creator, entrepreneurial hack is you should create something that you want, that you need.

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Yeah Because if you want it or you need it, then there's a good chance other people need it. And those were sort of like the two things I was putting my faith in was if, if I want it, then there's- Yeah...

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gotta be other people like me. Yeah. I- I've talked about this on this podcast a lot.

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I just think that, like, when you come from the content side, the journalism side, you create a different type of product than if you come from the sort of growth side or, or, or sales side.

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Like, there's, it's just more of a gut feel. I remember I was talking with Kevin Delaney, who started Charter, which is about the future of work, and he was like... We, we did, like, a Clubhouse. Remember that?

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Remember the Clubhouse days? Those, those two weeks- Yeah. [laughs]... with Clubhouse? It was hard. [laughs] It's very, it's very embarrassing. I did too. Other people did way more.

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Anyway, w- I did one with Kevin, and Kevin was- th- someone asked a question. They came up on stage, I think you raised your hand there, and asked about how he, like, sized the market and understood the...

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And he was like, "Oh, I was just... You know, I've always been trying to figure this out myself as a manager, self-taught, like, sort of manager.

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[laughs] And so I just figured that there was a lot of other people like me out there." And I think you build different products 'cause of that. But what gave you faith to, like, become, to go solo, to go independent?

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'Cause this is something that, you know, it started three years ago. It's a very, it's, it's an i- it's still unusual, and I don't think as many people went down this path as maybe were thought originally.

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But what gave you confidence that you could do it? Yeah.

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So I mean, I did [clears throat] for, for the first eight months that Tangle existed, I was building my mailing list while I was working a full-time job as an editor. Smart. Yeah. So I- [laughs]...

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I, I mean, I, I put my nose down and, I mean, you know, I ate shit for eight months and worked 16-hour days- [laughs]... and didn't sleep and sacrificed my weekends.

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I mean, I, I really went after it, and I got to a point where I think the list was at about maybe 4,000 people or something, and I pressed the button on introducing paid subscriptions, and I, you know, I, I did the opposite of what Substack told me to do at the time, which was I was a daily, and they said, you know, "You should have one of your newsletters free, and paywall 80% of them."

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And I inverted that because it never made sense to me.

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You know, I, I always thought if I have four newsletters that are free, then there's much more opportunity for one of them to catch fire and go viral and be shared widely or whatever, resonate with people.

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And so I just paywalled the Friday edition, and I made those a little bit different, a little more, like, outside the format.

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And about 15% or 20% of my list converted in, in, like, the very first push to go to paid, and I was like, "Okay, you know, that just means I'm here now.

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If I do this, 3X this audience, then I'm making as much money as I am at my current job."

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And, you know, I did it for another month or two, and when I saw that the growth was pretty consistent, I pretty much decided, like, "Okay, I'm gonna pull the plug," and then I started building the off-ramp to kind of get out of the job.

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So there was like a three or four-month period where I knew I was gonna quit, and I was, like, putting money away and building the runway. It was the metrics. I mean, it was seeing the number of people- Yeah...

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that converted. So I- 'cause I remember you emailed me, 'cause, like, I just, like, threw out the five to 10% figure, which I think is pretty legitimate, but, like, you, 'cause you convert way more.

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Why do you think that is? Like, first of all, what was your open rate, like, when... I know open rates are inflated now, but three years ago, they were, they weren't inflated. What, what was your open rate then?

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To get, to convert to 15% is, is really high. Yeah. I was seeing pretty consistently above 55% when I was on Substack, before the iOS update.

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So I, I'm pretty confident that, you know, from a pure metrics standpoint, we were, we were, like, way above the kind of industry average.

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And Substack told me to expect to convert 5% of the readership, so I think your metric of 5% to 10%- Yeah... is pretty in the ballpark. As, as far as I know, I think Matt Yglesias runs Slow Boring.

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He's the only person who I've ever seen share his numbers who was...

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I think he converted, like, 17% of his readership or something, which is, that's the only one I've ever seen publicly that was above mine, which is at 16% now.

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And I think- So you, you, you're, you're currently at 16% conversion of free to paid? Yeah, correct. Okay. Yeah. We have about 50,000, just over 50,000 total mailing list, and 8,000 of them are, are now paid subscribers.

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Over 8,000. I think 8,500 maybe. So, you know, I think it was, I think it was two-pronged.

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I mean, in the beginning, I know we're gonna get to this 'cause, uh, I know this is in your wheelhouse, but I was, you know, I was not running ads, and I was promoting the fact that we were ad-free.

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That was part of my shtick is, like, we're 100% independent. Yeah. We're not affiliated with any political groups, whatever, and I, I hammered that a lot. No investors. It's just me. No ads. I'm not taking money- Yeah...

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from anybody. I think that helped.

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And I think also just, you know, I think a lot of people rely on the kind of gimmicky, you know, uh, cliffhanger previews in newsletters that are then cut off, and you have to get to the, like, pay to read the rest of the article.And the call-out boxes and the tricky...

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You know, there's just, like, a lot of stuff like that. And I would just be like, "If, if people don't subscribe, I'm gonna have to go back to my job. Like, I need to live," [laughs] You know?

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Like, it would just make, I'd just make it personal and say, like, "If you think this project's worthwhile, there's no way it survives unless people subscribe, because you're my only source of revenue," and that seemed to be enough, and I would do it.

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You know, I'd make light of it and stuff, and keep the subscriptions- Yeah... pretty cheap, but yeah. Yeah.

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Well, it's funny, 'cause I think Substack would now give your exact recommendation versus their recommendation that they gave you now or then, if that makes sense. To, to paywall fewer articles, you think? Yeah, yeah.

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Their, their recommendation is actually to, to, to go that path now, because I think what they have, have realized, and, and just the data will end up showing that, is that you...

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The, the impetus for people to subscribe to kind of newsletters that are tied to an individual is different than, quote unquote, "institutional brands." It's a less transactional.

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There's more people who wanna support this existing and, and you not going back to work for HuffPost or, or Fox News than y- y- you have when you're The Washington Post wanting to, someone to subscribe.

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Or, like, Elon Musk- Right... going out there. Like, [laughs] you know? Yeah. Like, the reaction to that is, is gonna be a little different than, than you saying, like, "Hey, I,

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I, I, I, uh, I, I need your support for this." And I think that is why it doesn't necessarily make sense to have too much of the content be behind a paywall. Yeah. No, I mean, that, I, I buy that. I mean, I, m- my,

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I think my attitude in the beginning was just mostly I don't know yet what is gonna really resonate and what, which kind of newsletters are really gonna, you know, get people to forward them and share them on Twitter and stuff like that.

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And when I didn't know that, I was like, I don't wanna limit the pool of how many opportunities I get to get sort of that organic group. But yeah, that makes a lot of sense to me.

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I mean, I definitely, I, I think I benefit a lot from the fact that I have this opinion section in every newsletter, which makes it really personal, and a lot of readers feel a connection with that, and I answer a lot of emails and, and do all the kinda little stuff that I think- Yeah...

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builds up the relationship with the reader.

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[gentle music] So how did you end up thinking about, about the brand and then you?

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Like, I, I, I hate the word personal brand, but, like, a lot of the newsletters, and, and you've written a lot about this, because I think you've probably found it that, 'cause I certainly have, the, the amount of interaction you get through email is, is just far different than, than at least I've experienced writing for all sorts of different media formats.

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But, and I think it's because it's a personal... You know, the inbox is a personal place.

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It usually, you know, this is where you get messages from people you know, colleagues, friends, et cetera, and so I think it, it is different than a, a webpage dynamic.

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But how did you end up thinking about balancing building, like, a brand, Tangle, versus, like, y- it being tied to you as a person? Yeah, it's a really good question. I mean, when I was...

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Early on, my initial idea was to just have the sort of Vox-type explainer section that's like, here's, you know, here's what you need to know about this story, and then the right and the left's take, and that just be it.

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And early on in, like, you know, when I sent the newsletter out to 100 friends and family and, like, tested it, the overwhelming response I got was people being like, "Well, what do you think?" Yeah.

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I'm like, "I'm int-" Like, "You're a political reporter. Like, tell me what you think." And so the idea of introducing the whole My Take section was something that happened pre-launch but was a result of that.

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And so sort of on the fly, I started having my opinion there. And, you know, I mean, I, I think of, I think of Tangle's brand as obviously being intertwined with me, but I, I do try and keep it separate.

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I mean, we feature some other writers sometimes. Obviously, every newsletter has a ton of other people's opinions in it.

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Whenever Tangle the brand is being, you know, if, if I'm getting criticism, like, "I thought this was supposed to be an independent newsletter.

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I thought it was supposed to be balanced, but today in your take, you're, you know, you're explicitly picking one side over the other," and my response is always, like, "I, I don't see another way to be really transparent about the news we're delivering than being honest about how I'm actually viewing this event or what I think."

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So Tangle is balanced because we're giving complete equal space to, you know, a spectrum of political views, but I am a person who is being explicit about, you know, what my view is here in this one three or 500-word section.

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You can take my opinion or leave it, but, you know, I, I'm trying to be really clear about that it's in this vacuum. Yeah. And it's a hard thing to do. It's a really...

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I'm, I don't know that I've totally figured that out yet. So I think there, there's a lot of focus on the lack of trust, right, in journalism. And, and it's, it's interesting to read, and times, like, of course, Twitter.

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Like, I'm a journalist, so, like, we're, we are, we spend too much time on Twitter.

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But I think people are being more explicit about, like, their beliefs that there's this giant conspiracy among, quote unquote, "the media."

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I, I mean, I read a lot about it from, like, the Silicon Valley people, 'cause I think maybe I'm in that bubble a little bit.

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And, like, I read the stuff, and, like, I read these threads, and it's, like, very involved, this conspiracy of the media and stuff like this. And I'm like, wow.

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Like, I either I don't get invited to these cabal meetings [laughs] or they don't exist.

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But the fact that, that th- this distrust e- exists, it, it, not just in this bubble, but y- you know, you've, I, I'm sure you've exper- I can't even imagine writing about politics, by the way. What...

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That [laughs] you- [laughs]... you must have, like, the thickest skin in the world, Isaac. [laughs] But like- Yeah, definitely. I've developed it over time, yeah.

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But, like-So much, let's leave aside le- like, there's a serious societal, I mean, we've got major divides in society.

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If, if you were to sort of do, like, the, the, the prosecutor's take on what, on how quote unquote the media is, is, uh, did wrong in, in this e- era of, you know, com- complete polarization and distrust in the products that many journalism organizations are creating, what would be your top points?

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Or do you think that, like, you know, journalism is blameless in this? No. No, I definitely don't think that.

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And, and I mean, I, I, to be clear, I think I benefit tremendously from the distrust in journalism, and journalists in particular, and I'm not shy- You should be out there stoking it. This is, like- Yeah. [laughs]...

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a great business. Yeah. [laughs] One of my favorite, just a quick aside, one of my favorite, like, businesses from, I used to cover, like,.com businesses, like, in the early days, and, like,

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e- email marketing was a total mess back then. They used to do these things like one bite of the apple. You could basically just spam anyone in the world, and they ended up- [laughs]...

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having to have, like, a law against it. But they, uh, there was this company, uh, uh, that made these high-powered email servers that all the spammers loved to use.

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They were all, like, based in, like, Daytona, Florida, and, like, spamming people nonstop because they couldn't take away your home. And this, you know, they knew that this was happening, so what did they do?

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They started a, a, a spam-detecting software company on the side. [laughs] So this is just an idea. This is just- Yeah. Yeah.

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I mean, look, I, I, you know, I try not to partake in too much of the kind of journalism navel-gazing that goes on.

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I definitely have some, you know, there are some pieces in the Tangle archive, you'll find some, some pretty explicit media criticisms in there from me.

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I mean, look, I, I think first of all, the biggest one, the most obvious one to me is that a lot of major newsrooms don't have ideological diversity among the staff.

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I mean, I, I, to me, that's the number one thing that's a problem.

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I, you know, the, the experiment that I put to readers a lot of times is, you know, there, there are basic events that happen that are The Wal- uh, The Wall Street Journal and The New York Times, two tremendous papers.

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I think they're both great newspapers. You know, objectively, they have the best, most experienced, most highest-paid reporters in the game, with The Washington Post maybe.

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So you would expect them to be, you know, the most careful, the most balanced, the most trusted by their readership.

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You can watch them, you know, put side by side a straight news article from The Wall Street Journal and The New York Times covering a speech that Biden made, and they're all there at the same event, sitting in the same seats, watching the exact same speech, and when you read them next to each other, they're different, and they're really different.

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They're not a little different. They're really different. You know?

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There, there might be a quote or two that they both hang onto, but the first people they go to to reflect on the piece are sources that are kind of, like, in their circle and of a certain ideological slant, and readers are keen on that now.

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And, and I, I think that that is sort of like the fundamental thing is, you know, a lot of people at The New York Times have left-leaning politics, and a lot of people at The Wall Street Journal have right-leaning politics, and they kind of hire each other, and they network with each other, and they bring each other into these circles.

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And those are, like, the best of the best. So when you get to The Huffington Post, and you get to the New York Post, and you get to, you know, Fox News, whatever, it's just more extreme. That, that's number one.

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I think the big thing is just a lack of ideological diversity in these newsrooms.

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And then, you know, from my perspective, I think the other thing is y- you know, the drive for traffic and, and clicks and shares that started 10 years ago in sort of the Facebook era, and then obviously the 24-hour news cycle which started way before that.

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But they, you have to keep, you know, it's, it's, news is entertainment at a lot of these places, and you have to keep people interested and engaged, and they have to click, and it's like, and that makes, you know, I mean, everybody knows the feeling of clicking the headline of some story like, "Holy shit, the world's ending," and then you read the first, the lead and the nut graph, and you're like, "Oh, wait, this isn't exactly what the headline said".

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[laughs] And then you keep reading and you're like, "Oh, no, this actually isn't that at all." And you know, uh, we can debate all day about what the motivations are behind that.

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I think, to me, it's pretty clear that a lot of them are economic forces. But, uh, you know, that, I think newsrooms are responsible for that in a big way. Yeah. Yeah. It's...

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I, I always joke about The Atlantic 'cause, like, you, you open The Atlantic [laughs] and it's like the world is truly ending, like- Yeah. [laughs]... tomorrow. Yeah. [laughs] I was joking the other day. It's very funny.

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They're having a Progress Summit. I was like, I'm like, "Well, I don't know if that really matches up with what you guys are-" [laughs] "... regularly producing." Yeah. We do need a Progress, um, uh, Summit.

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But what I find is very interesting too that what you've done is, is try to bake it in on the product level, right?

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Because I think one of the reasons why there's a lack of, of trust in a lot of quarters of journalism products is because it's a whole mix of things.

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And, and you make choices when you, like you were saying, when y- when you're covering a Biden speech, you make choices that are not, um, transparent. And is that bias?

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Well, yeah, I guess, because we're, like, humans and stuff like this, and any time you make choices, they're a choice.

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It's just the same way as Silicon Valley, it's bullshit when they say algorithms are completely neutral. No. Like, humans made, like, made these algorithms. Yeah. And they end up having biases within them.

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And it's the same way obviously with humans. And I think what you did, and maybe it was copied by Semafor, but maybe they didn't see it before [laughs] which is, is try to delineate what is what.

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Because usually a news article is, you know, to, you know, Justin Smith was on here before. It, it is a black box to a degree. Yeah. I mean, look, uh, I guess full transparency, I, I s- I spoke to the Semafor guys.

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Uh, actually, Ben s- inquired about, uh, acquiring Tangle, or... Thing, I mean, I think what they're doing, especially on the global scale, is really necessary.And people want it. Readers want it.

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They want that, you know, I, I think, uh, yeah, how Justin puts it, the black box of it. They wanna know how the sauce is just made. They want that untangled a little bit. Yes. And we felt- Untangled.

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I feel really- I see what you did there. Yeah.

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[laughs] I feel really good about the, the format because it's sort of unimpeachable in a lot of ways, where it's just like I'm giving this space in a really even-handed way and in a really clear, transparent way.

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And, you know, if people are upset about how I write, you know, the neutral section, then that's, like, a, a good gripe to have and we can have that conversation. Yeah. And oftentimes that's the hardest part to write.

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But when you get to what the left's saying or what the right's saying or my take, it's pretty rare, you know, people might argue with my opinion, but they're never like... They never feel like they were cheated- Yeah...

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somehow, you know? So, um, which helps. So do you find, do you find you get, like, less unhinged feedback?

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I mean, unhinged is a qualitative term, but I'm sure, like [laughs] having written, you have gotten a lot of, like, what you would qualify as unhinged, uh, feedback.

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But do you find that people, like, step back from the ledge a little bit more because it's both transparent and because, like, it's you, like, at the end of the day? Yeah.

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I, I, I think it's, I mean, comparatively to places like Twitter and Facebook, definitely much less unhinged.

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Uh, when I get really kinda what I view as over-the-top responses, which happens every day, obviously- [laughs]... I, I also find that replying to them without sort of taking the bait- Yeah...

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usually diffuses it pretty quickly, because a lot of people just aren't used to somebody reading what they're saying, you know? They leave the Facebook comment, there's 2,000 others.

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They leave the comment on The New York Times, there's 10,000 others, and they reply to some verified Twitter account and the person never replies back.

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So when they hear from me, you know, I'd, I'd gotten that response of like, "Oh my God, sorry, I didn't think you actually read this." [laughs] You know, "I'm an asshole," you...

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A- and, like, and, like, that's really happened.

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And, uh, so I think, I think it, it helps to sort of turn the temperature down to just answer, but because most people are gonna feel represented in some place in the newsletter if they read the whole thing, you know, there will be one opinion they come across that closely resembles their own, uh, it's less often that I get, like, the unadulterated rage.

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[gentle music] So let's talk about the business.

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So you got 8,000 paying subscribers, right? And you're dropping the no ad thing. We'll talk about that in a little bit.

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But talk to me about how you decided on pricing, because I think you can look at, like, your, like, s- really high conversion rate two ways. It's like one is, amazing job, Isaac, and I believe that.

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Number two is, maybe you should be charging more than 50 bucks. [laughs] Yeah. No, for sure.

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When I launched the $5 and $50 thing, I mean, I had a lot of instincts about my readership, but I didn't take them, you know, I, I didn't take them on, on my own gut.

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That part, the business part, I didn't take on my own gut. I, I polled my readers actually, and I said straight up, "I'm thinking about introducing paid subscriptions. What would you pay?"

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And I offered, you know, multiple choice tiered sections where people could choose more than one. Yeah. And then I just sort of punched the numbers based on that and- But they always pick- The five-...

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the lowest one, don't they? Yeah, maybe. I mean, I- I'm hoping this- What I did-... 'cause I just sent one out and I'm like, "Mm, that, I, I didn't mean for you to choose that one." Yeah.

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[laughs] I hate when people don't choose the one I want. [laughs] Yeah. When I, when I did, uh, did this on Substack, they also had the founding membership tier. Oh, yeah.

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So I was able to do the $5 or $50, and then there was also the $199 a year tier, which maybe, you know, I don't know, 5% of the people who went paid picked. Okay. It was more than I thought.

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And yeah, and that, and I still have that on the website now on the current version of Tangle, and it's just listed as a thank you tier, which is, like, you know, you're not actually getting anything extra.

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Every now and then I try and send that group of people a specific email that's, you know, really tied to the business and the financials of things, just to keep them sort of appraised of that- Yeah...

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and, and treat them like founders. But really I just asked, and I, and I did the math and tried to pick the one that I thought would convert the most people. Yeah.

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So you started on Substack, but then you, you left Substack. Yeah, I left Substack. Uh, I have nothing but great things to say about Substack and the, the people there. I mean, it was a purely business decision.

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When, when did you leave? I left, uh, oh, just over a year ago. Okay. So October of last year.

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And, you know, we got to, Tangle got to a point where we were doing $200,000 in revenue, and I was paying them $20,000 for a newsletter service a year, and- Yeah...

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you know, I, I could make the jump to Ghost and save 18 grand, and that was basically- Yeah, and that was also-... the part-time employee...

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I mean, to, to, not to, like, talk Sub- Substack's side, but that was before they, they rolled out their most important product features, and recommendations is their first really good and interesting product feature to me, beyond being a basic, like, email provider and integration to Stripe.

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And- Yeah, there, I mean, there are things that I'm missing out on from Substack, for sure, and, uh, I'm actually, o- one of the products that we're thinking about rolling out, uh, through Tangle is a, a Tangle roundup that's just a recap of the week, because that's, like, the number one complaint I get from people, is the newsletter's a little long or they pile up in their inbox.

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Yeah.

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And I'm, I'm actually thinking about doing that on Substack to sort of see if I can benefit a little bit from the recommendations tool they have and, and see what that looks like, and maybe just have this little offshoot there because, uh, yeah, I, I do think, I mean, I, my, the old Tangle URL is still live.And I get something like 20 or 50 new subscribers every week from just people in the Substack ecosystem who accidentally come across it, even though it's totally inactive.

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And so I'm just, like, exporting those subscribers and bringing them, uh, over to my Ghost account. So yeah. I mean, S- Substack's a really good platform.

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And, you know, the only thing, the only other gripe I ever had aside from the fee was just that there was that period of time where, like, their brand was being very associated with a certain kind of political flamethrowing- Oh, yeah.

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[laughs]... type. Yeah. And, and for me, as somebody who was really trying to... My whole shtick was being independent. It, I started to get a few emails here and there like, "Why are you on Substack- Yeah...

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with Glenn Greenwald?" Or whatever. And I'm like, "Uh, it's not really like that." But, you know, it... I got tired of explaining that too. Yeah. But that was much less important than the 10% cut. Yeah.

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I, the, yeah, there's, it's an interesting thing of, of what direction they're gonna go. I won't, like, keep talking about Substack, but they, they're...

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You know, I, this idea that they're kinda like OnlyFans but for minds is like... It's like, okay, that's a nice tagline, but it's also like, eh, that's kinda creepy. Like, I don't wanna...

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Like, I always hate when people say, like, "Oh, y- you have a Substack." Like, I'm like a, "No. Like, I do a podcast, I have a newsletter, I do events."

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Like, it's just, that, that's not, to me, that's not very attractive. But I guess it is for other people. But y- y- you did it, you've been doing it, like, independently. Like, how...

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And, and you get to a point where you're like, "This is working."

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Like, it's like, you know, I'm making more money than I made before, and maybe not, but, like, probably, and I can see a path to making way more money than I was making before, and I'm enjoying what I'm doing, and stuff like this.

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But you have to decide, what is the future gonna be? Is it going to continue to be, like, a, a, a solo business?

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And you, you, you gotta grind through those, like, early [laughs] years, right, of, like, doing it, like, solo. And how did you end up thinking about where you wanted Tangle to go?

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Yeah, so I mean, I, I, from the start, w- once I saw that I was sort of, in my eyes, sitting on kind of a golden egg, like something I think could be my career, uh, you know, I was pretty sure in the beginning that I had no interest in building out a big newsroom, and that's still true, you know.

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I'm not trying to be the next CNN or something.

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My dream for Tangle is to have a really small, super well-paid, nimble team that is, you know, taking the format that we have and kinda the flavor we have, and, and maybe playing with it on other platforms, you know.

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I'm looking into launching a YouTube channel. I have the podcast already. I think there's, there's, you know, who knows what's gonna exist in 10 years?

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There's always gonna be some kinda new platform that pops up, and I wanna be ready to sort of, you know, expand the audience.

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I, I, uh, there is a kind of mission-oriented element of this where I believe it's good for American voters to be consuming the content we're producing. Mm-hmm. And so I want the biggest audience possible.

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I'm, you know, I've no, I'm not, I'm not shy about that, and, and I'm, I'm open to getting there however I can get there. So that, that's definitely part of it.

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But, you know, I learned pretty quickly that I really liked being my own boss, and I don't wanna work for anybody again or anymore.

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And so having a team around me that's, you know, kind of under me, quote, unquote, and, and working for me and with me is really attractive.

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And, um, that's, that's sort of like, I wanna bring in people who I really trust and believe, believe in our mission, and kinda grow it from there. And I see a lot of avenues. I mean, one of the things

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I joke about, or at least, you know, try to put out into the world just to see what comes back to me is, I think what we're doing is kind of, you know, it's almost franchisable.

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I could, I could take Tangle to France and find $100,000 of seed money, hire a really good French reporter to do Tangle in French, and launch it there in a really divided country.

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I have readers who are French who are, you know, expats or just French people interested in the US who write in and are like, "Hey, does, do you guys have a Tangle France?" Yeah. And I'm like, "No, but we could."

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And we could also jump verticals. I mean, we could go to sports. There's debates in sports that are happening every single day that I think we could break down in a similar way we do now, and I'm a big sports fan.

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I would read a newsletter that was, like, kind of the written version of, uh, PTI or something every day, you know? Yeah. So I think there are some opportunities out there that go beyond just US politics.

208
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That's pretty far down the road for me. Yeah. But... [upbeat music] Well, what I think is interesting is that it's kind of like a bet.

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Like, and it's, like, a, an optimistic bet that, like, we're gonna pull back from the brink, right? It's, like, kinda the anti-Atlantic homepage bet, right?

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[laughs] Like, 'cause if you go to The Atlantic homepage- Yeah... it's like, "Oh, we're doomed." Like, "Get your affairs in order, 'cause this, this is ending."

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But I, I'm of the mind that, like, I, maybe it's just having, like, walked the earth for 49 years, is that, like, you know, [laughs] there's always overcorrections.

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And, like, we'll get to the point where it's like, it's untenable to continue, like, the flamethrower wars on Twitter and whatnot. And usually, usually things end up...

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I, I had, like, uh, like, Steve Hayes from The Dispatch on here, and, and, like, I, I joked with Steve that, like, other than my parents, he was my favorite Republican in my life.

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[laughs] And, but, like, you know, yeah, The Dispatch operates between the 40-yard lines to me. Like, I don't agree with all their, like, politics and stuff, but they're, like, a normal, uh, party.

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And, like, I feel like things will end up s- end up back closer to, like, the 40-yard lines on either side. Yeah, I mean, look, I, you know, I was joking earlier about the Ben Smith stuff.

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But when we talked, I mean, what he said to me, which I thought was really interesting, because, you know, t- in my eyes, he's, like, a big media bigwig who's going out, and, you know, they're collecting $25 million to launch this new media company.

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And he was like-There is a lot of interest.

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Like, he, he, he firmly believes the market is going in this direction, where his opening in his eyes is CNN, New York Times, Washington Post, Wall Street Journal, their brands are cooked. Nobody...

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Like, it's, it's over for them. They're never gonna be able to redeem what they've done in the last 10 years. And so there's, like, a wide open door for people like us to kind of walk through.

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And as someone who's, you know, on this path on my own in a lot of ways, it was really encouraging to hear that from somebody who I think- Yeah... is, has a much better 30,000-foot view on things.

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I, I think that's probably correct, right? Like, 'cause I, I know CNN is trying to, like, pull, pull itself back to, to middle, and I think it has... It already...

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You know, I think we, we end up thinking about CNN mostly from an, a US context, but it's a global brand, and it- its brand is different in, in international markets really than it is here.

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It's only here that it's the sort of Jim Acosta, like, "How dare you?" Yeah. Kind of approach. [laughs] I tell people all the time that CNN's international coverage is still some of the best in the world, in my opinion.

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Yeah. I mean, I follow them for international news. But, like, with The New York Times, it's like... So I mean, you, you mentioned Maddie Iglesias. I think he, like, came... I think he was the one.

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Uh, I forget sometimes who, who I read stuff.

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But it was basically about the, the coverage of Silicon Valley, and how the, the Times decided to cover it from an investigative lens and holding power to account versus from a business or, like, a consumer technology service-y lens, and that all stories- Hmm...

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ended up being viewed through a, "We have to hold these people to an ac- account." And that, that's impossible to come back from with...

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Like, I, 'cause I see what the, the sort of Silicon Valley people end up, like, thinking about this, and it's so conspiratorial, and it's so...

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Like, there's no coming back from that, and I, I think that that is, it's a brand problem because a lot of, particularly in politics, my own view is the short-termism in a lot of, um, a lot of news sites was to try to surf the anti-Trump wave because it was good for business reasons.

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And this is not just... And w- I wanna get into advertising 'cause, like, misaligned incentives are, are rife in lots of different business models, not just advertising that misaligns incentives.

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You can argue that subscriptions misaligned incentives to be truly down the middle for a lot of these publications, I think. Yeah, for sure. I mean, I, I, I...

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There are so many reasons why I think news outlets sort of cross lines that they shouldn't. But, you know, to, to that point, I just...

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The Trump era really burned a lot of people, uh, and, and I think showed a lot of true colors, and there will be really long-term repercussions until, you know, the, the people who are politically engaged right now kind of age out of that, which is, you know, decades down the road.

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And I think for, as it's relevant to all those sort of big media outlets, you know, I love what CNN's doing, and I, I think they're making a lot of decisions that are good for their brand and good for journalism, but they're not gonna get a single Trump voter back.

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No. [laughs] I mean, that's not happening. I'll tell you that right now.

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So, you know, the, their whole course correct, you know, it might work for people who are just entering politics now, but it's not gonna work for anybody- Yeah... who lived through the last four years.

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I've, I have, like, 10 metaphors I use and just keep recycling them. And, and this one, [laughs] it's, like, you ever see Into the Void?

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It's, like, where the hiker, like, he ended up falling into a crevasse somewhere in the middle of nowhere. He was by himself.

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And, like, he injured his leg, and he realized he was, he was so far in, he couldn't possibly climb out, so he just had to keep going deeper, and I think that was sort of, like, their choice. They had to just- Yeah.

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[laughs]... "We're in too deep. Let's just keep going completely deeper," [laughs] like... Yeah, and now they're trying to come out on the other end, but I don't... [gentle music] All right.

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So, like, let's talk about the ads, you know? I always... I was joking when you, you had, like, uh, you had sent me a note, you know, like this.

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I knew that it was gonna come, that you were gonna run ads, 'cause I, I joke that, like, the first step to running ads is saying you'll never run ads. I mean, The Athletic did this. Everyone does.

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Or they just call them something different. Yeah. It's like, "We're not running ads. We're running, like, branded, you know, partnership engagement units." [laughs] Partnerships. Yeah. [laughs] Yeah.

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Talk to us about that because- Yeah... I mean, like, I, I always think with business models, like, uh, a- and editorial, like, you just, you have to match the two.

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And, and your editorial mission is, like, as you said, is to reach as many people as possible. Like, having, you know, having fair coverage of l- of politics shouldn't be a luxury good and stuff like this.

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I would assume you would think that, right? If you wanna have an impact. So you gotta match up. A, a pure subscription model doesn't totally work with that.

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On the other hand, just using your, your, quote-unquote, "free list" to, as a lead gen is sort of selling the value short. That's my basic belief. Yeah. No, I, I think that's right. I mean, look, I,

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the biggest reality that I ran into was that all my competitors...

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A- and to be clear, I don't, there's, I don't think there's really anybody doing exactly what we're doing, but there's enough places doing stuff that's sort of similar, either from the independent creator, kind of heterodox Substack writers to the flip side, which, like, does the left and the right but doesn't have any kind of, like, personality, in my opinion.

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They all have these m- more diverse revenue streams with ads and subscribers.

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And so I'm on my phone on Instagram or reading other newsletters, and I'm seeing ads for those newsletters pop up, and I'm just like, "Damn it."

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Like, they just have an advantage because they have more cash coming in, and they can spend more on spreading the word about their product.

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And th- that was, like, the original realization was like, I'm just handicapping myself, and I, I'm doing it based on something that's like-More my feeling of, you know, ads ruined all these other media companies I worked for and wrote for, and so I have- Yeah...

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this big beef with them because programmatic ads and pop-up ads suck, and all this stuff, but I never actually knew if my readers cared at all or if they had that kind of attachment.

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And then I asked, and then I found out that they actually didn't really care that much. Um- I think it's the most overrated- Which-... like thing that like...

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'Cause people, if you ask people, a lot of people, they hate ads, they hate ads and stuff like this.

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But like the reality is like tell me why then that like the, one of the most popular homepages on the internet is the Daily Mail. Explain that to me. Because- Yeah. [laughs]... it is a horror show.

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It is like a rogue's gallery of the long tail of ad tech, and like [laughs] it like literally every worst practice is going on there.

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But like they've got like really, really compelling content, and like people like don't necessarily care as much. I, I, I do not like adversarial business models, and I think there are too many out there.

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But I do think that like advertising can be perfectly fine, and particularly within like a newsletter context.

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I think what the best part of like newsletters is that they're, you don't have the capability to do a lot of the grotesque stuff that you do on [laughs] on a desktop. Yeah.

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[laughs] You can't do autoplay video on newsletters. And someone is probably cooking up like a autoplay video newsletter ad network right now. Yeah, I'm sure. Yeah. And, and, and that was, you know,

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another, the other thing that happened was I, I read 1440, which is just a, you know, pretty standard aggregating newsletter.

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They give you, you know, 10 things that happened, whatever, and I really like them 'cause they are very neutral and non-partisan, down the middle language in a- everything they do.

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And I've run ads in their newsletter, and I realized I kinda like the ads they had. They're just these text-based ads, and they're usually interesting products, and I'm clicking around on a lot of stuff.

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I bought like some shoes they advertised.

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And so when I started, this started working in my head, I reached out to the, one of the founders who I was booking ads through for Tangle in their newsletter, and we just hopped on the phone and talked for a bit.

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And, you know, I talked to him about how they do it and his model and how they think about it, and it was all just very benign.

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And I was like, "Maybe this just isn't, you know, may- maybe this is just kind of like a silly hill to die on." Yeah.

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And, you know, I w- we wanted to keep kind of the Tangle ethos in doing it because we do emphasize our independence a lot, and we do emphasize the fact that like we didn't take investors and we're not tied to any, like, political groups or whatever.

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And I want that brand, again, you know, to be a, kind of that unimpeachable feeling. And so we just said like, "Look, we're gonna do this. We got feedback on it.

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Like 10% of my readers said they cared, and of that 10%, like 5% of those said they would actually do anything about caring, like unsubscribing or whatever."

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I mean, it was a minuscule number of people who really objected in a way- Right. Yeah... where they like said, "Okay, I'm out." Um- I, yeah, the, people went into- And-...

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like the athletics comments were like, "This is, we're taking the..." Guess what? They just like reported, like the results and like people didn't cancel. [laughs] Yeah. And, and so,

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you know, I, the way we did it was we made some really clear guardrails, you know. Like we're not gonna, we're not gonna take advertising money from any political groups or any, like, overtly...

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You know, I read the Axios, I read Axios' AM newsletter, and I see an ad, a political ad during the elections from Michael Bloomberg. Like that doesn't sit well with me, to be totally honest. Mm.

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I'm like, I, like I would never do that in Tangle.

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I'm like, "This guy is a subject of your coverage," and the way Axios runs their ads is really clean and, like, easy on the eyes, but it's also easy to mistake that stuff for content.

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And so, like, there are certain lines that I was like, "I'm not gonna cross." We published a little page that's like, "Here's our ad policy."

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If we're, you know, if I'm advertising a shoe company, my guarantee is I will try the shoes before I advertise them. And so far, you know, we've gotten like some inbound stuff.

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You know, like I just got an email from some, I forget what it, maybe like a mimosa in a can or something company.

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[laughs] And I was like, "Hey, funny story, like funny thing about our ad policy is I have to try- I got it... the product first. So if you guys send me a case of your mimosa in a can, then I'll tell you if I like it.

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And if I do- Well-... maybe I'll advertise it. Like- We'll see if that continue. I think that, that, that- Yeah. Yeah. [laughs] That's like re- Who knows? It reminds me of like, you know, Instagram, like early Instagram.

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Hopefully it'll go in that direction. But like, uh, when like Kevin Systrom was like- [laughs]... personally like approving each and every, every ad.

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And I'm sure like [laughs] it was like- Oh, is that what I never heard. I mean, that's really funny... "Oh, yeah, that'll scale. That'll be great." Like, yeah, you're gonna... Yeah. [laughs] Yeah.

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Uh, that, that sort of- Yeah... went by the wayside. But, uh, yeah, I mean, I think that'll be... So are you gonna do direct sales, or are, are you looking to do some backfill with networks or...

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Our idea is to just go, I mean, we...

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First of all, we, in our launch, when we announced to readers we were gonna do this, we just set up a form for people to, because I know I have a lot of, like, entrepreneurs and stuff who read, and said like, "You know, here's a way to fill out if you're interested in advertising for us."

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And yeah, we're just gonna sell, you know, 70 to 100 word space in the newsletter.

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And I think probably right now our, our idea, right now what we're entering the market with is just charging on like a CPO so we can guarantee that, you know, our newsletters are getting 20 or 30,000 opens, 'cause we have a 55 open rate, you know, on our, on our free mailing list.

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And I've handed that over to somebody on my team, Magdalena, who does, had been doing all of our social media stuff and wants to get more into like a growth advertising role. And I'm trying to stay uninvolved with it.

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It's basically like she- Yeah... books the stuff. She sends me the copy for the ad, and I like say, "All right, great," or, "I'm gonna change this." Yeah. "Let me know if that works for you." I, I think ads are great.

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I think the one thing that I would always counsel people is, like, you have to realize, like, it's, it's, it's, nothing is easy, like, and particularly with making money.

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Like, and it always becomes more complicated, and it's one thing to sell ads. It's another thing to service it and do the client service and do the trafficking- Yeah... and do the reporting.

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And there's no easy ways to making money. I mean, just the same way, like I feel like with subscriptions sometimesPeople don't realize that, you know, it's great to have five thousand customers. Yeah.

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That's, that's great. The bad part is you have five thousand customers. [laughs] Yeah, exactly. You have five thousand people who have a chance of forgetting their password.

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You have five thousand people who could mistype their own name. And, like, [laughs]

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that's real, and it becomes y- once you start taking people's money, there, there, there, uh, there's obligations with that too, and that's reality. Yeah.

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My, my new favorite thing that happens to me with my mailing list of, now that we're at over fifty thousand, I think it happens every single day, is I get an email from somebody demanding to know why they've stopped getting my emails, and ninety-nine percent of the time it's because they've unsubscribed- Oh, yeah...

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from the mailing list. So I have to say, "Well, actually-" [laughs] "... you unsubscribed. That's why you're not getting them, so you gotta turn your emails back on."

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So yeah, I feel, I feel that pain pretty acutely for sure. Okay. So what is the... wh- what are you gonna end up this year at? Yeah, you've been admirably, uh, open with your, your statistics. Yeah.

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So, I, right now we're doing about thirty-six thousand dollars in monthly recurring revenue.

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I think we launched this ad stuff probably a little less than a month ago, and we've brought in something like, you know, five or six thousand dollars of ad revenue so far.

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So my hope is, you know, we could do that f- in November and maybe December and add another, you know, technically another, I don't know, s- I guess it'd be five thousand dollars of monthly recurring revenue.

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I'm hoping that the subscription business will hit forty thousand dollars in monthly recurring revenue. Typically, we grow at about a thousand to two thousand dollars a month in, in our monthly recurring revenue.

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So that's, that's my target, is to hit 40 before the year is out.

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We have a couple big advertising pushes that are gonna come up and some spends that I hope give us the returns to get there, 'cause the organic growth has definitely flattened a little bit.

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I think that would imply the mailing list is, you know, dancing around sixty thousand people, and we'll see if we can get there.

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But, you know, going into the new year, I'm really unsure about what's gonna happen Q1, Q2 next year. Yeah. Because I...

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Ev- all the signs are on the wall that the advertising revenue's gonna dry up, and if we get into real panic mode with inflation or a recession, I don't know if people are gonna keep buying subscriptions to newsletters.

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So I'm kinda- Yeah... gritting my teeth and, and holding on to see what happens. Well, I mean, that's the good part. Well, first of all, it's, it's better to have the recurring revenue of, of subscriptions.

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And, and then it's also better to be at a price point that it's not gonna... I mean, like, it depends on, on the person's, like, situation.

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But like, the, that's, the fifty dollars or, or five dollars a month i- is not gonna... I mean, I, I just paid, like, twelve dollars for an egg and cheese sandwich, but that's New York City. But like- [laughs] Yeah...

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it's not gonna, it's not gonna make or break [laughs] a lot of people's budgets, like.

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And I'll say too, I mean, one thing actually I don't talk about very much, but I just checked this morning, 80, 83% of our subscriptions- Okay... are annual. Yeah.

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Which is like, you know, the, that reduces the churn so much, and it, it makes the, the money that's coming in a lot more stable.

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So that, that's a really big kind of, you know, saving grace for me is once a year, 83% of my subscribers have to decide they're not gonna bail, and, uh, that lowers that, that kinda churn rate pretty significantly.

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Yeah. Okay. Cool. Well, Isaac, thank you so much. Uh, really appreciate you taking the time. Fascinating what you're building. Always a fan. Yeah. Thank you for having me.

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I'm, uh, I'm, I really appreciate what you guys are doing at the Rebooting. It's one of my go-to reads. Awesome. So- We're gonna clip that... I'll be- J, get that one... I'll be stoked to get some space in there.

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[laughs] Yeah. [laughs] Yeah. Awesome. That's right. Thank you so much, Isaac. And thank you all for listening. We'll be back next week with a new episode. Thank you for listening this week.

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We will be back next week with a new episode. The Rebooting show is produced by Podhelpus. Podcasts are a great way to expand your client base.

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

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