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The algorithms have failed tremendously. Local newspapers continue to kinda like die out, and their quality just tanks. There is a massive opportunity here.

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What I am curious about is how big you think this newsletter could be. Who knows what that could become. Is it twenty-five thousand? Is it a hundred thousand? Is it bigger than that?

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Obviously, growth comes from consistency. It comes from authenticity. There is kind of two ways to grow. There's organic and there's paid.

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I always kinda thought, if I can't grow this thing organically, then I can't grow it. Sixty days, a hundred one thousand five hundred dollars in revenue is, is insane. You will succeed. Uh, you just have to be patient.

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Welcome back to the Creator Spotlight podcast.

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[upbeat music] Today, we're speaking with Michael Kaufman, who has, over the past year, built up a thriving local newsletter business serving Upstate New York's Catskill Mountains area.

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His main newsletter, Catskill Crew, is the foundation for a larger business.

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Uh, for example, he recently tweeted that he had a hundred one thousand and five hundred dollars in revenue pipeline for the next sixty days, so very excited to get into all that.

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He's very good at the business side of newsletters.

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Um, he also runs a private membership group called The Newsletter Club, where he and something like fifty other people share tips and stories about largely building local newsletter businesses.

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Michael, thanks for coming on. Pumped to be here, buddy. Let's dive into- Let's do it... all things newsletters. Okay, so all things newsletters. To start, I wanna ask how many newsletters and spinoffs you have. So I...

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Let me... First let me try to get it right. I think I have it.

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So you started Catskill Crew last November 2023, um, but you recently started a spinoff called Catskill Crew Land and Lodge, which is a real estate and hospitality-focused vertical, and then also one eight hundred Fly Fish, which is totally its own thing.

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Is that everything? Yeah, that's correct. Uh, in terms of my own publications, Land and Lodge, I'm still examining the right strategy for that.

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Um, an independent, you know, s- an, an independent publication under the Catskill Crew umbrella or weaving it directly into the existing Catskill Crew. Um, the whole goal here is I'm not trying to guess.

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I let my audience and subscriber base kind of drive the entire publication of what I do. Um, but at the end of the day, it has to be fun and engaging for me, otherwise I can't do it. Yeah.

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[clears throat] I can never fake something I don't really believe in. Mm-hmm.

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Um, so looking at your pretty sparse LinkedIn account, I don't think you've updated it for a couple of years, Catskill Crew isn't even on there, but there are a few things on there.

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I can tell that, you know, for the past decade or so, basically since you were in college, you've been, like, a founder type. You like to start things.

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Um, but before all that, the only other connection I could see to media is you seem to have worked at The Boston Globe when you were in college in some capacity.

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Um, so I'm really interested [chuckles] in, in as much as there is a through line from that, like a decade and a half ago to starting a newsletter now. Is there a through line, and what is it? No, not at all.

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[laughs] There's no through line. Uh- What did you do there?... Boston, Boston Globe, holy heck, what a throwback. Um, yeah, I was basically a scab.

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I came in to, uh, you know, uh, support the, [clears throat] the digitization, um, and specifically around the super boring classifieds side. They, like, just integrated SAP.

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It was a ghost town when, uh, when I started working there. It was more of a ghost town when I left. Um, you know, it was a little way to make some money as a college kid who was kinda tinkering with ideas.

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I worked Friday, Saturday, and Sunday, uh, which was miserable. Uh, but it was a lot of fun at the same time. I had to buy a pair of khakis and, uh, you know, pretend like I was a professional.

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Um, there was no way I pulled that off. [laughs] But it was, it was a great time. And, you know, I really, to be honest, learned nothing that translates- Hmm... to what I do today. Well, I actually...

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I would dispute that in that if, if it was about classifieds, I mean, looking at Catskill Crew as a newsletter, I'll describe kind of the content structure, uh, for the listener.

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Basically, it starts, there's this custom image in every issue. It's a weekly newsletter. I think it's Thursdays right now.

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There's this custom image, some crew news, which might be an event coming up or a piece of local history or something.

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Then there's a moment in time, which is a photo, a historic photo, and then some happenings, which are generally kind of ads, and then event listings for the following week sorted by day.

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So this is like, Catskill Crew, um, the aesthetic, the visual branding kind of represents this too. It's kind of like a, a, a country store, a country general store bulletin board, which is digitized classifieds, right?

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I love that. That's a beautiful way to put it. Um, yes, to some degree. However, it's a massive contrast to traditional media, which is, you know, it's top-down. I'm very much bottom-up.

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Like, whatever my subscribers want, I'm... It's a newsletter by the people, for the people.

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Um, [clears throat] I'm always tinkering with my content buckets, but at the end of the day, it's, you know, the folks who are gonna decide the direction of this thing.

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And so it's, it's really about kind of spotlighting what's happening here, what's happened here, and what's gonna happen here in this area. Um, so yes, perhaps there is something I learned there, but, like,

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I'm boots on the ground with the folks, talking to my subscribers. I'm making fans and, you know, I'm becoming friends with, with these, these individuals.

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And I think that's the most im-important thing, and again, kind of a direct contrast, which is like Boston Globe has no idea who their subscribers are, if they even have any anymore- Yeah. [chuckles]... versus me.

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Like, I'm out there. I wanna know everyone, and I think that kind of personal touch is extremely important and something we could definitely dive into as we discuss, like, hey, is it better to go wider?

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You know, take Catskill Crew and spread it across the nation, or is it better to go deeper? Uh, more publications, um- Mm... you know, more robust in a specific geographic region. Okay, yeah.

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So, um, we were talking a little bit before we started recording that you, you aren't from the Catskills, but you moved up here a few years ago.

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Um, and I bring this up because looking at yourThe, the paid ads that you currently have live for the newsletter, some of the messaging feels more geared towards locals, some feels more g-geared towards tourists, and it's kind of interchangeable.

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Like, one was like struggling to find things to do in the Catskills. To me, that fe-fe- feels geared towards locals, especially new residents like kinda yourself.

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And then Explore the Catskills feels more geared towards tourists, people maybe who are in New York City thinking of coming up to the Catskills for the weekend.

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Um, but my question here is, like, who is the Catskill Crew subscriber?

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And, like, what is the type of person that kind of it reproduces, in that, like, you know, if you start reading it, you become more X type of person. Who is the Catskill Crew audience? Yeah. It's funny.

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Um, when a bunch of businesses started coming to me saying like, "We wanna partner and reach, you know, the Catskill Crew crew," I was like, "How do you guys define that? What is that?" Um, because, like,

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I knew internally, but optically I wanted to understand what other businesses were perceiving from the exterior looking in or trying to peer through kinda this, this foggy glass since no one could really see the metrics or the people who are subscribed.

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So for me, it was always geared towards the locals and the weekenders. Uh, vacationers were last.

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If you don't have the locals, you have nothing, and the locals is kind of a, a pretty broad, uh, uh, broad kind of, uh, uh, statement, um, because you have the folks like myself, I moved up here in 2017.

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Um, I started as a weekender, pretty quickly became a full-timer.

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You have the old-timers who've been here for a very long time, where there's some conflict between, you know, this, this next generation moving up here, raising prices, everything like that.

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[clears throat] So I really tried to gear it towards the authenticity of the region. Uh, speaking... I mean, it's, it's very much the way I speak in the newsletter is how I speak in general.

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I'm not kind of putting on a face or putting on a voice. It's just like, you know, it's very much just kind of something that's applicable and well-rounded for everyone.

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Um, however, you know, based on recent surveys, it...

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I'm right about 75%, uh, locals, weekenders, and then that other kind of percent is starting to bleed into the vacationers, which is, is great overall, and it, it offers kind of a Catskill Crew experience expansion on top of what I've already built.

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Um, but I think, like, if you don't have the locals, uh, you, you got nothing. Yeah. No, totally. And I like that.

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I, I, I know that these kind of events are a big part of what you do, where you do meet people, and you kind of build these relationships. Um, and I, I think the last time I interview...

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I've interviewed a couple people on here who do local newsletters.

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The last person who was kinda more similar to you was probably Ryan Sneddon, um, back in [tsks] it was, like, March or May or something, I interviewed him.

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Um, but he takes a very similar approach in this, like, holding company type of thing and, like, you know, being out there with the people and meeting them.

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Um, with him though, I think it was more, like, definitely just the locals, less of a tourist thing. So where I'm going with this is I'm curious if you think about a cap on the audience size.

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I was trying to find, like, how big is the Catskill region, and I read that it's, like, 500,000 people with maybe up to a million w- in kind of, uh, you know, the, the peak summer season.

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Um, and I'm a big believer that anybody talking about a total addressable market, they're, you know, it's always far larger than what their actual realistic reach could be.

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Um, and I feel like you're probably somebody who thinks about that a lot. So how big do you think... 'Cause you were just talking about a bit too is, like, is this more of a regional vertical?

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Do you go more in national ways with, like, expansions, whatever. Rambling a bit here now, but what I am curious about is how big you think this newsletter, Catskill Crew, could be realistically. You know, I don't know.

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[laughs] Like, you know, realistically. Yeah. Like, who, who knows? And I think the, the goal of how I started this thing remains the same. Like, let's have fun. Let's play around. Let's not take it too seriously.

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Um, and, and let's be authentic. And [clears throat] obviously, growth comes from consistency, uh, it comes from authenticity, and it comes from, yeah, putting some cash into the Zuckerberg machine to get some ads going.

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But, you know, I cover such a vast region, right? It's a couple hours east to west, and it's a couple hours, uh, north to south.

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Um, you know, some of the events are outside of the Catskill forest, uh, which is always funny when someone's like, "Hey, that's not in the Catskills."

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No, but it's a 10-minute drive if you live in this town in the Catskills. And so the whole idea is, like, this is for people who live in the Catskills and the proximity kind of radius around the Catskills.

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So, you know, look, it's, uh, approaching 11,000 subscribers. Who knows what that could become? Uh, is it 25,000? Is it 100,000? Is it bigger than that?

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Now, Catskills are also unique in the sense that, you know, uh, New York City, Long Island, Brooklyn, Queens, all these places are, you know, um, they're, they're a tourism machine for the Catskills themselves.

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And so there is an entire different audience that I could spin off. So Catskill Crew is very much for the experience, land and lodge, very much for the real estate side of things.

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I think that there is ample room to move in different directions, target different audiences, create different revenue streams, but at the end of the day, it's like, don't try to do everything at once, you know?

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And I think, um, one of the biggest things that I hear all the time is like, "Hey, man, I've dumped a ton of money into this, into the, into the ads. I got 3,000 people, but I can't find a single advertiser."

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It's like, well, because you've been in existence for 30 days, no one actually knows who you are.

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And, you know, as a local newsletter, you really do need to be boots on the ground, in my opinion, to, to, to maximize the outcomes, um, and, you know, to build the trust with, with your audience, whether they're here or they're a vacationer.

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So it's, it's all about the long game. And, uh, you know, kind of just-Listen, run surveys, try to extract as many insights as you can, and let- Mm-hmm... those kind of start guiding you in the direction to move forward.

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And some of these things, you... I, I couldn't have imagined some of the things I'm doing now, uh, a year ago. And I think that's like- Like making a Monopoly game?

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[laughs] I was in Taos, New Mexico, and, um, it was like 110 degrees, and we were sitting inside, and my girlfriend and I were playing, uh, some board games.

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And we saw at the Airbnb they had a Taos Monopoly board, and I was like, "Holy crap, man, a Catskills one would be pretty cool." Within 10 minutes, I was talking to manufacturers in the US.

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I come to find out that all of them are manufactured overseas. So I said, "Screw it. Let's go direct to China." Um, cut the cost in half, and it's been a, it's been a process. And that's been an adventure too. Um,

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but they should arrive in, uh, hopefully 30 days. There was a manufacturing, you know, hiccup. Um, but yeah, I mean, that was something where I just ran a survey, "Hey, does anyone want a Catskill version of Monopoly?"

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And it was like 97% in favor, and I was like, "All right, here we go again." Um- I'm sure everybody with an Airbnb at the Catskills is probably gonna buy one. [laughs] Every hotel has put in orders- Yeah... of like 10.

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Airbnbs want multiple. Wow. Um, you know, the businesses offered to pay to be on there, but- Mm... in my opinion, that didn't resonate with the brand.

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Yes, it could have capitalized the initial production run, um, but I wanted something evergreen. I wanted something that highlights- Yeah...

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the nature, the reservoirs, the fire towers, the mountains, the, the rivers here, the towns. Uh, so I kinda went more broad and, and for me, that's, that's again, kinda more on brand with how I think of things.

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I would hate to- That would be... Yeah, that would be more appropriate- Just have-...

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if you were working with all the local diners in the area to make, um, the placemats, which w- I [laughs] it seems like something you would do. [laughs] Probably would. That's a free one for you.

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Yeah, I'll probably run with that later today. Thanks, buddy. Um, okay. I, I do wanna get into the revenue m- more in a bit, but first I, I wanna spend just a little bit more time on, on how you've built this audience.

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You, we talked a little bit about paid ads. Um, I looked, I looked at your all... I read every tweet you've tweeted in the last year.

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Um, and you tweeted on September 1st that you had 3.9 thousand subscribers, so it'd been a little under a year, and then you activated meta ads on October 1st, and then a month after that, you had 7.7 thousand subscribers.

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So in two months you'd doubled it. Um, there was a bit of an implication there that you hadn't been running ads before, but I k- I, I feel like you had been.

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Um, so my question is m- more broadly, like, how have you got to 10,000? And I know it's a lot of ads, but I'm also really interested in more of this kind of boots-on-the-ground stuff you've been talking about.

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Yeah, for sure. Um, I was, I was definitely playing around with some, uh, Instagram boosts, but I wasn't taking ads seriously.

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I'd turn them on while I was having a martini, throw 30 bucks into the machine, and see how it went.

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Um, you know, I, I always kinda thought, "If I can't grow this thing organically, then I can't grow it from a, a paid standpoint."

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And so, you know, I went out, launched the first newsletter, uh, shout-out, my mom was the first subscriber, and pretty quickly it was like 200, 300 subscribers.

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I was like, "Holy hell," like, w- "This is really interesting." And I come from a world of startups where you usually have to put a lot of money into advertising to start seeing some return.

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Um, and so that early traction was validation that, okay, these core content buckets and the, the thesis is correct. Um,

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and so I really spent a lot of time on the branding, making something feel very premium, making something feel right for this region, [clears throat]

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and making something that really was a pedestal for, or a launching pad for a much bigger kind of company, um, which is how I've always thought of things. Um, and so I started very much organically.

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I would just spend a lot of time on Canva, moving into Instagram, showcasing the businesses that are putting on these events, making them look really good, and then they would actually just share the content on my behalf.

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So I was riding the coattails of these existing businesses and, you know, pretty quickly that was 500, 1,000 subscribers. I put on some events, which I had no idea if anyone was gonna show up to.

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Uh, they've all sold out or, you know, we could dive into that in a, a little bit more detail, but that's a, a really fun adventure.

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Um, and that kind of whatever user-generated content or whatever you wanna call it, people basically posting and tagging Catskill Crew, started kind of putting some more fuel on the fire.

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And then, you know, I started this TNC, the newsletter club, and I was talking to a bunch of people who are smarter than me, and they're like, "Yeah, we're 10,000, 15,000, 20,000 subscribers." And I was like, "All right.

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Fine. I'll do it. I'll, I'll, I'll actually spend some time on meta ads." And, um, yeah, it's been... You know, that's kind of a puzzle that's ever ongoing. Had you, had you ever done them before?

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Had you had any experience? No. God, no. Uh- I never wanna do them again. [laughs] Every time I go into it I'm like, "Not again, please, Lord." Um, but they do work. Um, and you know, there is kind of two ways to grow.

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There's organic and there's paid. And, you know, organic looks like posting on Reddit, posting on Facebook groups, you know, having compelling content that is shareable.

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And then from the, uh, paid side, um, it's really just meta ads, Reddit ads, Instagram boosts, stuff like that.

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And, you know, tinker, play around, and, uh, A/B test constantly, examine the data, and just keep fine-tuning, uh, you know, the media and the calls to action. Mm-hmm. Um, I wanna talk about visual branding for a second.

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You, you did bring that up. So for both Catskill Crew and One Eight Hundred Fly Fish, I think it's this very digital retro vibe. For Catskill Crew, it's browns, beiges, kind of the color of old paper and wood.

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Like I said, it really feels like a country general store bulletin board.

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For Fly Fish, it's, um, still some of those browns and beiges, but more of this purple too, and more of a pixelated, feels like '80s, '90s video game, uh, more than kind of that general store feel.

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Um-It's also, I, I, I think you use Midjourney a lot. You use AI to, like, produce those custom images at the top. It's pretty tasteful use of AI.

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I think, one thing I think about a lot with AI, kind of on a tangent here, is that, you know, it collapses that gap between, um, vision and execution ability.

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And I think for you, like, uh, for a lot of people it really shows that gap when they try to use AI. Like, it shows that you don't really have a vision, you just got access to execution.

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I think for you, there's a pretty... There's not much of a gap there between vision and execution. Like, it feels correct. It feels unique. Um, it doesn't, like... It...

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Often when I look at really poorly executed AI things, I get kind of like a taste in my mouth, like a metallic, like, like blood in my mouth or something. I don't get that with you. It's a dirty penny.

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It's a dirty penny. A dirty penny, exactly. Um, okay, so that's kinda my, my little AI rant tangent. But I, I, I think you've done a great job with the visual branding.

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And so tell me about that, and then beyond the looks, kind of the brand identity and the values that, for example, don't allow you to put local businesses on the Monopoly board.

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Kind of a big question, but yeah, start with the visual branding and then bring me into, like, kinda more the brand identity. Yeah. I've always... Again, like, my background is in a world of startups.

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It was always building brands, from beverage companies to digital health companies to hospitality, and so that brand has always been important to me. Um, something that really resonates with that audience.

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It is a personality. The brand identity is a personality. I look at Catskill Crew, 1-800-FLY-FISH as people, basically, and they represent certain things.

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And luckily enough, they are extensions of myself, which is why this is so fun. They're two very different sides of me, but yet kind of cohesive.

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Fly fishing is, you know, uh, the Catskills is the birthplace of American fly fishing. You know, behind me, you have four fly rods on the wall. I'm a nerd and I actually have a fly fishing shirt on.

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Um, and so it, it, it always feels right to me to spend a ton of time thinking about that brand. And it doesn't have to be perfect to start. It's going to be iterative. It's going to evolve.

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It's going to hit growing pains. You're gonna kind of be faced in a corner and be like, "Ah, well, which is the right direction to go in?"

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But I challenge everyone to take their branding extremely seriously, because it will pay dividends. It will open up more doors for revenue and opportunities for expansion of the brand.

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People will take you more seriously. You optically punch above your weight class, so even if you have one subscriber, if you're branding strong, people will take you more seriously than kind of, you know, clip art.

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Um, which clip art's making a comeback, actually.

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Um, and so, you know, I, I kind of went in, it wasn't originally with Midjourney, but I spent a lot of time playing around with that tool, fine-tuning what this looks like, very much vintage illustrations for the Catskills, paying homage to the 1700s, 1800s, early 1900s history.

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I also saw a gap in the market that no one was really addressing it that way. It was very much, eh, just kind of, um, uh, soft, curvy, modern lines designed for influencers, and like, I am not an influencer.

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That doesn't resonate for me. What does resonate for me is the history of this area.

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So I really kinda tried to tap into that and, and pull that kind of past into the present, and then bring that into the future, because I think those types of things are timeless.

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And so, um, yeah, that's how I think of Catskill Crew. With, with 1-800-FLY-FISH,

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uh, fly fishing is very much like a, it's been an old white man in a tweed coat sport, and that is not the future of this sport, and that's not the future of the conservation side of this.

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And so, you know, for me, I was looking at, what is a more youthful, playful brand that doesn't take itself too seriously? Yet kind of it didn't feel right to go with the vintage illustration.

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You needed something way more fresh, way more fun. And I thought, like, kinda this pixelated, um, kind of '80s, '90s look was really interesting.

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I always found kinda the retro style of fly fishing in the '80s and '90s was really fun and, and nostalgic.

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And so I was kind of trying to find that balance of like not too far back, uh, but like how do you kind of pull from the past and bring it again into the future?

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Um, and so yeah, it's, it's very much a, a, a very playful, uh, non-serious attitude I have towards fly fishing geared towards a younger generation.

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And, and again, kind of both of these things are designed not to be newsletters, but to be entire brands. Yeah, no, I like that.

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The, the fly fishing branding, the 1-800-FLY-FISH branding in particular, was really evocative for me of a few things I've seen. Like for one, fly fishing itself is this kind of Zen thing.

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Like a- it's kind of like a, you know, ASMR type of thing.

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And I could see like, I don't know, this, these pixelated little guys, like, just casting the rod and casting the line, um, and like, you know, the sound of a, of a bubbling brook as just like a 10-hour YouTube video, that kinda thing.

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Or like, um, there's this guy I've seen on Instagram. I, I forget his name.

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I don't follow him, but he always comes up on my feed, where I think he lives in like, I don't know, the Midwest in some cabin, and his, his catchphrase is like, "Well, hello, buddy."

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And he's got this mustach- [laughs] You know this guy? He's got this mustache and he's got his dog. Yeah, yeah. He's playing like vintage video games on a vintage TV making these like nostalgic '80s meals.

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And like when I saw the 100, 1-800-FLY-FISH branding, it like immediately was that to me. It's like this kind of, this cozy aesthetic. Um, I don't know, not a question in there, just, just how I saw the...

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It- it's well done. No, it's, it's al- it's always interesting to actually hear how something I spend so much time on resonates with other people, kind of what emotions does it, does it evoke? How do they feel around it?

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Um, because like I go in having my own assumptions in how it speaks to me, and it's gotta click, right? There's... I- it drives me mental if the branding doesn't click. Like, I can't move off go.

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Like mon- Monopoly reference here. Like, I cannot start the business until like the, the, the, the branding feels cohesive. Again, recognizing perfection is impossible.Um, and it will grow.

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But, like, does it click with... And, and that's such a, a visceral feeling for me. Yeah. No, totally. Um,

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you talked a little bit earlier about how you don't think you're an influencer, and I always ask people this question 'cause it's always a slightly different answer.

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What does the term creator mean to you, in this, you know, the internet content sense? Yeah. I think there's probably been a shift from, like, the word, the term influencer into creator.

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Um, influencer for me has always been, like, you know, the other day a hotel came to me and was like, "Hey, we wanna put you up if you put some content in your newsletter." And I was like, "Not, not what I do."

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Um, so you know, I've passed up quite a few stays at nice hotels and good restaurants because I just, I refuse to do that. Um,

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so the creator seems like it's rooted in more of a, uh, like the internal fire of just a desire to create versus an influencer feels like it's more, yes, maybe you have a desire to create, but it's more influence and pulled in the direction of revenue opportunities.

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So yeah, I'm, I'm a creator. Maybe not my person, my face. I don't go out and, you know, share my own content. My Instagram has zero posts. You know, I don't even have a Facebook.

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Uh, but like, no, I do create and, um, that is rooted in kind of that, that deep instinctual desire to, to make stuff. Mm-hmm. I, I like that distinction.

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I think, I think, too, like, I mean, I, I have s- [laughs] I have so many definitions that I, like, kind of cycle through and learn from people.

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But I do agree that, that being a creator is, like, about the craft, whereas being an influencer is more about just marketing a thing. Um, but so Michael, as creator, you used to do a podcast called CT Startup Podcast.

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And try as I might, I could not find any of your original episodes. So CT as in Connecticut. Um, it...

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I think you started this in 2015 with a couple other people and did it for just a couple years, and then you stopped, and they kept going, and then I think they kinda stopped two years ago, too.

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Um, but this was, like, the only other thing I could find that was, like, you kind of actively contributing to the internet in that way. Tell me about that and, like, why you started it, why you stopped. Yeah.

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I, I, I thought, uh, you know, again, I, I started companies living in Boston while in, in college. Moved back home to be with my family, you know, my father, my grandmother.

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Um, and I, I, I stayed involved in the startup scene, and I saw it as, like, not nascent, but it was a fraction of what the energy was in Boston.

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And so I started looking around for who's building stuff because those are the folks I just... I like to be around two types of people, people who build things and people who fly-fish.

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Um, and so, like, I light up around those types of conversations. It's super engaging. And so I actively just sought these folks out.

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I connected with a couple entrepreneurs and a couple attorneys who worked with startups, and we were all just talking about the startup kind of ecosystem in Connecticut, which was there were some startups in general, and there was some capital being injected into these ventures through, uh, CT Innovations.

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But, like, it still didn't seem like there was a hub for it.

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And so yeah, I think it was, like, uh, the attorney Dave Menard's idea of, like, spinning up this podcast and, you know, it was just a fun little adventure and, you know, just kinda shooting the shit around, like, what's happening in the startup scene.

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Um, uh, interviewing different entrepreneurs from across different disciplines and industries.

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And, uh, yeah, at some point I moved down to New York City, and I kind of, like, phased out of that and, and remained in the, in the startup scene down there. Um, but yeah, Connecticut, all these kind of...

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I, I, I think it's a strength to some degree, not a weakness of a, of a smaller scene. Like, yes, there's the big fish in a small pond, but, like, it's tighter-knit community in my opinion. That's how I see it.

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And I think through that more spontaneity and more magic can just happen if you, if you really stay involved.

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And if you could put yourself as a linchpin or put yourself in the center of that, not from, like, an ego-driven way, but just, like, really you're, you're involved in it- To be a participant...

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like, amazing things happen. Yeah. Yeah, be a participant and, and even kind of be a conduit within that space. You know, "Hey, guys, we're meeting up for a couple cold beers to talk about whatever's going on."

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And, you know, it takes time for those things to build, and you have to have patience, but I think, like, that's where the magic is. Yeah.

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Um, I wanna talk one more thing about, like, creators and the creative versus business side. This is something I think about a lot because some people I talk to for this are more traditionally creative driven.

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They're writers or, you know, musicians or whatever. Some people are more traditionally business side, which you kind of come from that.

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Um, and it's, you know, this imperfect Venn diagram, right, of, like, the really creative people versus the really business-driven people, and then in the middle are the people who I think thrive the most in the type of creator economy that I kind of investigate in my work.

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Um, and you're a perfect example of that. Um, but again, you don't come from this traditional creative background.

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I would say the same thing, like, I, you know, I couldn't help when I was researching you but think of Ryan Snedden again, um, 'cause you guys just both run these, like, somewhat similar stru- similarly structured local newsletter businesses.

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Um, and with him too, he was not... He was, like, an engineer. He didn't think of himself as a creative type, more of this business person.

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Um, and I think more and more I'm convinced that, like, people like you who have this understanding of, like, the creative side and, like, you know, I was talk- when I was talking earlier about the way you've used AI, where there's, like, clearly the vision there that isn't failed by the easy access to execution.

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Um, I don't know. It's rare to see. I'm curious if you've thought much about, like, the creative versus business divide in the creator economy, if that's... I don't know.

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Maybe that's just something I think about a lot, but how do you see that? Yeah. I think it's a good question, um, [clears throat] and probably an entire podcast. But I think that if you have an audience, you know...

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It's hard for me just to create. Let me take a step back.

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Like, I can't just create for the fun of it, because I knowIn order to continue on that journey, there needs to be monetization, and you can't just thrust monetization into something without kind of, um,

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the, the cohesiveness of the long-term vision. And so like how do you build something? And I always use the word authentic. If it's not authentic, you ain't going too far in the long run.

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And so like how do you kind of identify those opportunities as a creator and then bring kind of a perspective or bring someone on board who has a perspective of, hey, long term, this is how we can monetize, this is how we could grow this audience.

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How many Instagram accounts have 1.5, 5, 10, 15 million followers and they're making, you know, shekels because, you know, it's, it's, uh, you know, uh, another protein powder that they're advertising?

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You know, but there's so much opportunity there, and it doesn't mean spin up a community or a newsletter. It could be a product. It could be a digital good.

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Um, you gotta kinda think about what can you do, what's unique around, you know, your audience, your skill set, and then what do the people want? And the beauty is once you have that audience, you can really just listen.

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You can ask the right questions, get the, the insights and the data, and then just kinda extract that and think, "Huh, hey, does anyone want this thing?" I don't build anything without my audience saying yes, right?

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Like, it doesn't matter if it's a poster, it doesn't matter if it's a hat, it doesn't matter if it's a Monopoly board. Um,

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and you know, I'm bringing that same perspective now to like, okay, I've proved that I could do something. Long way to go to deem this a success.

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Um, I, you know, I could prove I could do it with local newsletters, now let me try something totally different.

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So 1-800-FLY-FISH is kinda taking that creative element, taking kind of my personality, what I'm passionate about, and bringing my business experience.

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And so like I already am, I'm building this outdoor media company, but the main goal is to turn it into a products company, to turn it into an experience, turn it into a community.

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Um, and that's kinda how I look at all these things. It's, it's really about the, the, the newsletter itself, local, doesn't matter what it's for, it's all a launching pad for a holding company. Yeah.

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This is, th- kinda the way you're talking about this too, um, brings me back to what I was writing about in, uh, as we record, last week's issue of the newsletter where I wrote about this idea of content capital, and I think it's like that's partially why people who come from a business background are so good at this is 'cause like you're kind of already thinking about it in those terms, like content capital being like your reach and your ability to reach an audience.

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But then it's about converting that to financial capital.

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It's about social c- for you, you know, using social capital, creating social capital, converting that back into both content capital and financial capital, and going out and meeting people.

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Um, but I'm struck, my last thought on kind of this like creative business divide is I interviewed this guy Andrew Huang, uh, back in, uh, April or February or something, and he is a longtime YouTuber and, you know, even before YouTube.

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He's a musician. He was like selling his songwriting talents on eBay, um, in like 2002 or something. Crazy. Creator before the, the creators existed.

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Um, but I interviewed him 'cause he'd just published this book, Make Your Own Rules, which is kind of about, it's kind of a bit of a memoir, but also really a kind of educational book about making it in the creator economy.

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And the way it was written, I could tell that the audience it had in mind was like a musician mainly, but really any type of creative who was struggling to think of their work in business terms and translate it into that.

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Hmm. So maybe they had cultural capital, maybe even social capital.

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Um, I'm ch- struggling to think of a word that would represent just pure skill in that capital sense, but they were struggling to think in terms of content capital and financial capital and converting these things, um, among each other.

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So that's kind of, I don't know.

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I've, as I've been thinking about this a lot, I think like the creator economy as it, in as much as it's a thing, is kind of calcifying into any other given economy, where the people who have the business sense have the leg up and are like, you know, quickly eating up space, and that like early vision of like, oh, you can make an Instagram account and go viral and suddenly have this big following and like make money being an influencer.

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Like that dream is dying, is maybe already dead, right? Because it only works if you understand these different types of capital and c- you know, conversion between them. Hmm. Yeah. I, like I have a call with a big, um,

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automobile manufacturer today, and I, it's just, yeah, I got introdu- introduced to this company, and the reason why, yeah, I went into it going like, "What the hell?" Like, I only work with advertisers that are local.

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Now, this car company has a local dealership, and what struck me was the conversation immediately went into they are phasing out of the macro influencers because there's no more trust there.

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You know, they're much more focused on like how do they find those authentic voices that maybe the, the audience is a fraction the size, but the potency and the, the punching power is so much more significant.

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Uh, and so, you know, I'm gonna kind of riff and ramble a little bit, but like I think at the end of the day, those authentic voices are all that matters, um, where whatever your platform is.

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And I think like in many ways the newsletters are experiencing that same thing, which is like the biggest newsletters, yeah, they're gonna continue to crush it.

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They're gonna continue to bring on big advertisers on a CPM basis. I don't work with CPMs. I think they're trash. Um, personal opinion.

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I go to every different type of advertiser and I'm like, "Okay, this is what you want. This is what you need. This is what I think is fair." They're like, "Whoa, that's ridiculous." I don't apologize.

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I try to work with them because I believe in the value of, of what I'm doing, because working with me is not, uh, an advertisement. It's a, it's a partnership.

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It's a, um, it's a true promotion of me giving you my blessing and then opening up my door to subscribers.

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And so-Yeah, I, I probably didn't answer that directly, but I think at the end of the day, it's just very important to, to examine all of these things with a business eye, um, to move patiently.

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And you talked a lot about, like, okay, you have one million, whatever, someone dumps a ton of money into, into ads. You have 10,000 subscribers, great, but there's a cap on how much advertising revenue you can bring in.

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I think the focus is on what is your subscriber LTV? How do you monetize those subscribers? I don't mean, like, in a cash grab way. I mean in a meaningful way, where those people are going, "Please take our money."

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They are pre-ordering the products, and I think that takes a form of, like, creator creativity.

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You need to be a creator to create this thing, this platform, this audience, your unique voice, but you also need to be a creator and creative to then figure out what they want.

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I, I think, like, the idea of, like, business is a little stale, and creator doesn't necessarily give enough respect to, like, oh, they j- can just create.

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So I do think you're right about, like, when you do combine these two worlds, and you are thinking effectively about, like, how do you create this audience in the right way, and how do we monetize it appropriately?

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Like, the fun thing for me is every audience and every newsletter has a... it's a different puzzle to solve. It's a different opportunity to monetize, and I think, like, I, I...

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again, I've been building startups for 14, 15 years. Doing a newsletter is the most fun I've ever had in my entire career. Um, and, and I think everyone should do it. Yeah. No- You all have an authentic voice.

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I, s- I love, I, I love, I love everything you said there.

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I think, um, my last takeaway, last thing I'll say is that, like, really more and more to participate in the internet, like, which I think, the creator economy, you could say it's just, like, the, the internet economy at this point.

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Whatever. Th- maybe we don't need to get so into that [laughs]. But it's just kind of like a baseline that you have to be able to speak some of the basic language of marketing and business.

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You have to know terms like LTV. You have to know terms like CPM if you're gonna participate. Um, I wanna get though now into revenue. Um, so you tweeted a couple...

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Y- it is a bunch of tweets I could reference, but this one you tweeted a month ago, November 5th, um, that you had, like I referenced in the intro, $101,500 in the revenue pipeline for the next 60 days, and you broke this down by $48,000, so about half in sponsors.

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Um, merchant products was $42,500, a little less than half, and then the rest was $7,000 in events and $4,000 in partnerships. So I was very impressed.

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You know, obviously, the next 60 day- 60 days, $101,500 in revenue is, is insane.

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Um, break down for me kind of the business structure and your holding, your holding comp- local holding company model that kind of frames all this. Yeah. So the holding co is actually, like, a, a longer term play.

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Like, I'm a partner in a fly fishing business locally. Like, I'm paying close attention.

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I'm, I'm, I, I have an offer in on a commercial building, which I'm looking at doing a general store and a, a little tap room, um, prime location, and like I know that- General store makes so much sense.

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Dude, exactly, and the name is... The branding is insane. I'm not giving it away yet, 'cause I haven't bought the domain. Um, and I'm too lazy to do it after this, or I probably won't remember.

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Uh, but, you know, I also wanna make sure that deal goes through. We've been working on it for a few months.

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Um, and I know the reason why I'm gonna do that is because I know that through promoting events, I can drive revenue-beating days. Every event we've thrown is a record-beating revenue day, um, [clears throat] by far.

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And so I know, you know, owning this business and promoting my own business, yes, like, everyone's gonna have a blast, and we're gonna make a ton of money through this location, and guess what?

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I could extend the Catskill Crew brand by selling merch right there, and it's super high traffic area.

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Um, you know, I'm looking at other services, businesses, like firewood business, which is so boring, so unsexy, but, like, it's snowing outside, my wood stove's going, everyone needs firewood.

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Um, and so, like, you know, what kind of, like, sexy and non-sexy businesses can I, can I start, or can I, um, uh, acquire or own a percentage of?

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And I think the beauty is, like, one of the things I've been thinking about, and we've been talking about in the newsletter club, is, like, don't guess either. Like, spin up a landing page that does lead gen.

253
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Say, "Hey, you know, Catskill Hardwood, you know, do you need firewood?" And it's like, cool. They go to that website, it feels premium.

254
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They put in their information, and it's like, oh, shit, you know, okay, I got 72 leads in, in one post. All right. You know what?

255
00:41:23.070 --> 00:41:37.650
I'm gonna go start this business, or I'm gonna go and invest 25,000, 50, 100,000 into a local firewood business. So, like, you know, you don't have to actually spend more than $20 to test this thing, this thing out.

256
00:41:37.750 --> 00:41:49.930
Um, so that's how I've always thought of the, the local holding company. As for kind of, like, the way I've structured, um, I guess, is it best to, like, break down, uh, how I've structured that 100K plus?

257
00:41:49.970 --> 00:41:56.370
Or- Yeah, yeah, yeah. Whether, whether it's, you know, it could go y- I mean, we listed on that tweet sponsors, merchant products, events, and partnerships.

258
00:41:56.590 --> 00:42:03.650
Um, maybe at the top level, like, why the revenue is broken down into these four buckets and by the percentages it is.

259
00:42:04.230 --> 00:42:10.890
Um, and then maybe after that we can go through, and you can tell me a little bit about each specific part of the business. Yeah.

260
00:42:10.950 --> 00:42:20.810
I mean, you know, look, I think the most important thing is not every month is like that, right? There's been months where I say no to advertisers for two months straight. There's been...

261
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I said no to most advertisers for three months early on because I thought it would dilute the brand.

262
00:42:25.350 --> 00:42:35.170
So I'm happy to kinda go through a, a famished phase where, you know, I'm just walking through the desert because I know kind of there's going to be these peaks and these troughs.

263
00:42:35.230 --> 00:42:46.990
And so, yeah, there's some, some good money coming in right now. Um, who knows if that's gonna sustain, but, like, I think if you are patient and you are protective of your brand, it's almost inevitable.

264
00:42:47.130 --> 00:42:56.690
Um, so the sponsorships are mainly partnering with tourism agencies, um, working with local businesses. Now, what I recognized was there's a cap I could charge local businesses.

265
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I do not try to charge max amount whatsoever. It'sWhat can they afford in a respectful way? Um, because I do know the value of, of direct inbox. This is not an algorithm. This is not a black box like print.

266
00:43:11.522 --> 00:43:27.842
So I- Well, I, I should say, just to interject, it's like, I mean, when you, when you're working with local businesses to advertise, it goes back to, like, you are being a participant in the community, and it's not about, like, maximizing your revenue opportunity and thinking of it in these kind of, like, really harsh, you know, competitive business terms.

267
00:43:27.862 --> 00:43:34.022
It's about being a participant in the local community and, like, allowing that to thrive. I give ads away all day.

268
00:43:34.342 --> 00:43:44.962
You know, if a, if a business can't afford it or if I'm trying to build a relationship with them, I'll just plug them, no problem. Follow up, "Hey, guys, love what you do, loved your spot. I was in there the other day.

269
00:43:45.502 --> 00:43:55.242
Here's some data, you know, 12,000 opens. You got X amount of clicks. Like, if you ever wanna talk, I'm, I'm here." And I, I'm not doing that just to build a relationship.

270
00:43:55.342 --> 00:44:05.722
Like, I want my subscribers to know about that place as well. So I'm coming from a, from a place of like, yeah, I'd love to monetize it, I'd love to support them, and I want my subscribers to know about them.

271
00:44:05.822 --> 00:44:16.802
So, um, but, like, for this area, the high LTV businesses are where the biggest money's at, you know. Uh, some of the folks in the newsletter club have done a great job targeting those.

272
00:44:17.142 --> 00:44:26.222
I live in a weird area in the middle of the woods. Like, high LTV businesses are, like, HVAC, dentists, you know, and the guy who does the HVAC is probably the dentist.

273
00:44:26.422 --> 00:44:33.102
Um, but, like, you know, it's, it's, it's the hospitality companies, it's the tourism boards that have been great partners for me.

274
00:44:33.182 --> 00:44:43.302
So I'm spinning up a lot of the, a lot of the drive for this revenue right now has been, "Hey, lock in these prices. We're growing, you know, 50, 100 subscribers a day.

275
00:44:43.702 --> 00:44:56.682
If you wanna work in 2025 because your 2024 allocation's already kind of eaten up, lock in these prices." That's why kind of this is looking like the start of 2025's gonna be significant. I do a lot of events.

276
00:44:56.762 --> 00:45:09.422
I think I have three, four events in the pipeline right now. Each of those is $1,500, $4,000, $5,000. The next one I'm gonna do is about $6,000 just through the way I'm structuring it a little differently.

277
00:45:10.042 --> 00:45:17.622
Um, [lips smack] there's ways where you can lower that price and then capture, you know, a percentage of revenue if they cross the threshold.

278
00:45:18.162 --> 00:45:31.062
Um, a lot of my, uh, uh, revenue coming in has been pushed back, like, 30 days off that projection because of a manufacturing error. I'm gonna sell 500 Monopoly boards. Um, you know, my cost is about $10.

279
00:45:31.102 --> 00:45:44.642
I'm gonna sell them for about $60. There's well in excess of 500 in pre-orders, um, or signaled pre-orders. I have not charged these folks yet. So I'm considering upping that initial production order to 1,000.

280
00:45:45.382 --> 00:45:58.022
Uh, but those ship out, I think December 18th. It's December 5th today. Um, I do discount cards. Each one of those cost me a dollar. Uh, I sell them for $25. I didn't price them. My subscribers priced them.

281
00:45:58.142 --> 00:46:02.651
Um, I didn't say, "Do you guys want..." I, I didn't say, "I'm gonna make these." I said, "Do you guys want these?"

282
00:46:03.142 --> 00:46:11.662
Uh, partnered with 10 amazing restaurants in the area, so it's very much like, um, it's a, it's like our little Mission Star guide in the area, right?

283
00:46:11.702 --> 00:46:19.542
And you get a discount, it supports local business, and the beauty there is these 10 businesses that I love are going to be promoting Catskill Crew.

284
00:46:19.562 --> 00:46:30.382
And I always find that incredible that, you know, and that's how I've kind of been able to grow this thing is making them look really good. Uh, they will then showcase that and bring their audience to me.

285
00:46:30.702 --> 00:46:41.522
And, you know, I wanna honor that and respect that and support them how I can. And so, yeah, it's a, it's a, it's a big couple months, and you gotta be kind of explorative and patient with this thing.

286
00:46:41.602 --> 00:46:51.302
I mean, I went months without any revenue, um, and gave ads away to kind of build those relationships with local businesses, and now is the time that you can really monetize them.

287
00:46:51.662 --> 00:47:00.142
I'll advise anyone who's looking at starting a local newsletter to partner with tourism boards because they're very much the gatekeeper to all the businesses in that area.

288
00:47:00.151 --> 00:47:11.042
And look, if they don't have the money to partner with you, give it to them for free. Start showing some kind of goodwill. Uh, it, it, it will pay dividends. Yeah. One thing I wanna

289
00:47:12.002 --> 00:47:14.902
just talk about briefly is, like, the financial reality, right?

290
00:47:14.962 --> 00:47:25.882
Like, a couple months ago, I interviewed this woman, Swapna Krishna, who was a journalist who'd quit her full-time job to start a newsletter and was able to do so because her husband has a full-time job, and she gets health insurance through that.

291
00:47:25.932 --> 00:47:31.822
And while she builds up the business, he has enough income to make the gap, right? So I understand with you, we've talked a bit about crypto.

292
00:47:31.902 --> 00:47:40.322
I imagine, like, when you started this, you weren't, like, in a rush to monetize. 'Cause the way you're talking about this, like, I agree. It's like, you be patient, you, like, work on these things.

293
00:47:40.362 --> 00:47:45.922
You don't, like, you know, build up an audience of 3,000 and sell these ads right away when you've only been around for 30 days.

294
00:47:46.402 --> 00:47:55.862
Um, so I'm always interested when I talk to people, it's like, well, the financial reality of starting a business like this or, like, being a creator and, like, starting to build a thing is like, you do kinda need to have a cushion, right?

295
00:47:55.962 --> 00:48:06.462
So, so my question to you is, like, could you have started this project or would you have started it in a different way if you weren't already feeling safe financially? I'm curious how that affects it.

296
00:48:07.302 --> 00:48:12.602
I, I don't think you can just start anything. Uh, look, there's exceptions, right?

297
00:48:13.492 --> 00:48:21.902
And, you know, I, I'm not absolute about anything, but I'll say it's really hard to just, like, if we're gonna talk newsletters, it's really hard to start a newsletter and start monetizing on day one.

298
00:48:21.942 --> 00:48:28.382
Like, n- near to impossible, at least at scale where you could live off of it. Uh, if you have an existing audience, sure.

299
00:48:28.402 --> 00:48:37.622
But if you're starting from scratch, you know, even if you dump a bunch of money into ads like we've talked about, and no one trusts you, no one knows who you are, you have two newsletters out.

300
00:48:37.682 --> 00:48:39.342
You know, you're still finding your voice.

301
00:48:39.682 --> 00:48:52.962
Just 'cause you got 10,000 subscribers, I would probably actually advise to, like, flip the script, go organic until you can really figure out who you're talking to, what your voice is, build that trust. Um, so

302
00:48:54.022 --> 00:49:06.618
no, I, I, I think you should kind of, you have to be patient with this thing, and you can't expect to just kinda, like, step in a pile of gold dog crap, um, because-It's just not the right way to do it.

303
00:49:06.698 --> 00:49:15.378
If you have the patience and you do deeply understand who you're speaking to and how to monetize this thing. Now, I will say

304
00:49:16.938 --> 00:49:23.978
after spending a year building a local newsletter, yeah, I guarantee you I could spin One Eight Hundred Fly Fish up and, and start monetizing.

305
00:49:24.018 --> 00:49:36.258
I'm already talking to now four different potential advertisers, but the reality is, is I have 400 subscribers. Like, I'm not gonna charge them a lot. I'm not even really looking to, like, maximize the outcome there.

306
00:49:36.378 --> 00:49:49.758
I'm trying to partner with them in a way that, okay, they see the value in this, they're willing to put skin in the game, and again, kind of optically it legitimizes my brand by having these core partners, and these core partners I'm very specific with.

307
00:49:49.798 --> 00:49:58.418
I'm only looking at these four because these are the four that represent the future of fly fishing in my eyes, and that's what I'm trying to represent with my brand.

308
00:49:58.478 --> 00:50:09.498
So, you know, I think it becomes even more challenging when you protect your brand so much that it actually shrinks your monetization opportunities, especially early on.

309
00:50:09.578 --> 00:50:20.958
So yeah, probably keep your full-time job, um, until you figure it out. Uh, but you know, I think, like, if you have some business experiences and you are creative and you know who you're speaking to,

310
00:50:21.958 --> 00:50:32.038
yeah, you're, you're-- you will succeed. Uh, you just have to be patient with it, and you... It, it sucks, you know, when you're starting this thing out and you have one subscriber, then 10, you know?

311
00:50:32.078 --> 00:50:44.258
It, it's hard to show up every time. But, like, if you really love what you do, then whatever. Patience and consistency. It, it will... It's, it's 100% what it comes down to. Yeah. Uh, I wanna talk- And creativity. Yeah.

312
00:50:44.278 --> 00:50:50.558
Well, that's kind of the big rule, the big, uh, [chuckles] ingredient you can't forget. Um, I wanna talk about the, the Newsletter Club a bit.

313
00:50:50.638 --> 00:50:59.958
So I understand it's a private community for local newsletter operators specifically, that I, I don't know if everybody in there is just that. Um, and you started it this August.

314
00:51:00.018 --> 00:51:08.458
I think you kinda led it, but you started it maybe with some other people. I don't know. Tell me about how this came about and, uh, who you started it with. Yeah.

315
00:51:08.558 --> 00:51:16.438
Well, uh, I called my buddy Jason up, who's a great human, and I was like, "Yeah, man," like we're playing catch-up. He's like, "What have you been doing?"

316
00:51:16.478 --> 00:51:26.178
I'm like, "Yeah, I run this little local newsletter, you know, having a lot of fun. I did, like, 10K last month on it." He's like, "Holy crap. Dude, you gotta start a course and start selling that."

317
00:51:26.218 --> 00:51:34.238
I was like, "Absolutely not. Like, no way." He's like, "At least start tweeting about it." And I was like, "Eh, publicly building, like, eh, it's not really what I do."

318
00:51:34.838 --> 00:51:40.618
Um, but you know, he did kind of over a few weeks start pushing me in a direction of, like, sharing the story and...

319
00:51:40.658 --> 00:51:49.318
You know, the reason I'm sharing this is because I do want everyone to win, and I think it's really fun when you're building stuff with other people, where especially it's non-competitive.

320
00:51:49.358 --> 00:51:55.698
You know, like, we're all in our own different markets, and I think, like, that kind of compound learning is important.

321
00:51:55.738 --> 00:52:04.878
And so, you know, I started kinda talking to some people on Twitter, and then going back to Jason and, you know, I ended up saying, "Screw it, I think I'm gonna do just community." You know?

322
00:52:04.938 --> 00:52:10.618
And it was, uh, $100 to join and the reason I priced it is because I want you to have skin in the game.

323
00:52:10.698 --> 00:52:19.038
I want you to take it seriously, otherwise we're gonna dilute the entire community and it's, it's gonna be zero value. And so 20 members joined in August.

324
00:52:19.158 --> 00:52:29.238
I was on a road trip out in Colorado, and I was firing off tweets and trying to spin up a Slack, and it's like, holy crap, like, some of these people are way bigger audiences than me.

325
00:52:29.318 --> 00:52:34.278
And you know, I think, like, what I started learning quite quickly is we all have different skill sets.

326
00:52:34.478 --> 00:52:43.638
Some people know how to s- speak to sponsors, some people know branding, some people know meta ads like it's a science. Shout out to Philip. Like, [smacks lips] automations.

327
00:52:43.798 --> 00:52:54.698
Everyone kinda has this nuance and different backgrounds, and we can all learn this. Even though we're in different areas, it's relatively the same playbook. Um, and now we're at 60 members.

328
00:52:54.818 --> 00:53:01.518
Uh, I'm not really sure what the future of it is, but I, what I've come to recognize is it does represent kinda the future of local media and journalism.

329
00:53:02.018 --> 00:53:09.458
You know, we're all kind of playing around with events-based newsletters and, you know, we have our different voices and our secondary and tertiary content buckets.

330
00:53:09.538 --> 00:53:23.918
But, like, I do think that as newspapers, local newspapers continue to kinda, like, die out, um, and their quality just tanks, it opens up a gap in the market for local newsletters.

331
00:53:23.938 --> 00:53:35.098
But most importantly, it actually creates a need, because local businesses no longer have any way to communicate with the local community. Uh, th- the algorithms have failed, uh, tremendously.

332
00:53:35.718 --> 00:53:41.638
Um, and so it, there is a massive opportunity here, and I, I really wanna support anyone who's, who's building in this space. Well, wait.

333
00:53:41.718 --> 00:53:46.938
So, so something I wanna get into here, so I fully agree, and I think it's like, like you think about even large media businesses, right?

334
00:53:46.998 --> 00:54:01.478
Like, The New York Times is the one really big success story where they figured out how to digitize really well, and obviously, you know, the thousands of smaller local newspapers, news organizations, et cetera, across the country didn't and failed to do that, and that's what you're talking about there.

335
00:54:01.558 --> 00:54:09.638
Um, and so I'm interested in, like, the, then the news side about it, the journalism side. So, like, your, the bulk of your newsletter is events, right?

336
00:54:09.688 --> 00:54:13.158
And I, when I talked to Ryan Sneddon too, it's events, because that's, that's how this starts.

337
00:54:13.198 --> 00:54:24.518
And, like, with, you know, uh, news- newspapers that have died out, it's like they made money on classifieds and, like, this kind of culture reporting. Like, that's how local journalism has always made money.

338
00:54:24.938 --> 00:54:35.958
Um, so I'm curious if, like, you have a sense of how many operators in your community have, like, you know, built on that, like they've built the foundation, the monetized product, like with events and stuff.

339
00:54:36.558 --> 00:54:41.178
Are many people introducing more, like, hard-nosed, boots-on-the-ground journalism into that?

340
00:54:41.298 --> 00:54:53.518
Like, I, I imagine it's probably less people than, you know, the majority, but is that something you're seeing in your community? Yeah. So I would say out of all 60, uh, 60 have started with events.

341
00:54:53.598 --> 00:55:05.898
It's, it's, it's an easy way to drive max value for, or early value for subscribers, and the curation is key here. Like, uh, okay, we all have community calendars. They're, they're garbage, right?

342
00:55:06.018 --> 00:55:18.250
Like-Um, show me some sort of quality control, some sort of curation, and you can niche down. Okay, the Catskills. Okay, the Catskills in this county. Okay, the Catskills in this county for parents, you know.

343
00:55:18.290 --> 00:55:22.170
You could find where the opportunities are, even if there is competition.

344
00:55:22.210 --> 00:55:38.430
[clears throat] So I think everyone has started in the event space, but I think we'll continue to just kinda see, um, some folks have websites as well, and what they're figuring out is, okay, I have this website where maybe there's deeper, richer, uh, content, but actually how does that compete against my newsletter?

345
00:55:38.670 --> 00:55:51.970
One of them might start actually cannibalizing the value of the other one. Um, so but to, to be more precise about, uh, the question here, I think we will see an expansion of content buckets.

346
00:55:52.710 --> 00:56:04.610
I'm looking at opportunities to partner with local journalists to basically have another version of, like, proper crew news, um, which is not necessarily written by me, but I wanna have contributors.

347
00:56:04.730 --> 00:56:19.350
You know, I, I do see this as a, yes, I wanna protect this, this brand and this voice. It's nothing but good vibes only, but, like, how do we kind of start establishing and expanding within this market to add more value?

348
00:56:19.550 --> 00:56:27.590
And, you know, most of the news here is how many ads do you have to read through or, like, sift through? How much distrust is there?

349
00:56:27.630 --> 00:56:36.110
So, like, how do you kinda create a trustful, um, authentic voice in this region that actually drives real value? Um, and it's not just about the clicks.

350
00:56:36.250 --> 00:56:47.430
It's not just about, um, you know, some sort of, like, attention-grabbing clickbait. But, you know, it's, it's trust. And again, that's a, a whole different world. But- Yeah...

351
00:56:47.490 --> 00:56:53.910
I think it's inevitable that some of us, if not all of us, start moving in that direction. Yeah. I mean, it's so much harder, right?

352
00:56:53.990 --> 00:57:05.790
Like, we could go into all the reasons of, like, you know, then the ethics and, like, the conflict with certain advertisers and whatever and, you know, it, it just [chuckles] it inevitably is like this community service, but creates all these, all these complications.

353
00:57:06.310 --> 00:57:11.250
Um, are there any people, any other, or specific,

354
00:57:12.390 --> 00:57:20.270
you know, projects, newsletters in your community that you would wanna, like, call out for, for whatever reason, that they're just, like, doing really compelling or unique, uh, work?

355
00:57:21.870 --> 00:57:30.410
I mean, I think Jas, who runs Winnipeg Digest, is doing a fantastic job. A young cat who's built out this brand, um, and he's doing it in a different way, right?

356
00:57:30.630 --> 00:57:41.030
Uh, I'm always kinda inspired after my conversations with him. He has his Instagram account and his social accounts, and it's, it's another monetization vehicle in addition to the newsletter.

357
00:57:41.110 --> 00:57:51.970
He is the face of his business, which, you know, is really significant. Um, what I've kinda discovered through my conversations with him is, look, like, all of our metrics are hidden behind.

358
00:57:52.030 --> 00:57:53.130
You know, for me, it's Beehiiv.

359
00:57:53.550 --> 00:58:05.250
No one knows how many subscribers I have, but the vanity metrics of social media are actually kinda the, the val- the validator that, oh, crap, okay, he's got nine thousand followers on Instagram.

360
00:58:05.310 --> 00:58:10.690
Like, yeah, that's pretty big. So it's also, like, how do you kind of start investing in one?

361
00:58:10.790 --> 00:58:21.370
For me, I, I, I put a little bit of money into, like, driving some, some followers there because it is an attractor for local businesses as well.

362
00:58:21.470 --> 00:58:32.000
Um, but yeah, Jas has done a great job in kind of running these two parallel paths, um, that kind of butt up against each other with different sponsors every so often. Um,

363
00:58:32.930 --> 00:58:36.780
you know, Philip with Orlando Signal, the- these were both early members.

364
00:58:37.210 --> 00:58:49.860
Philip's done an incredible job, you know, running our master classes on meta ads, really kinda changing the game for a lot of us to, to not just run meta ads, but to optimize these meta ads, to have the data to back these things.

365
00:58:50.430 --> 00:59:01.070
Um, Landon at Wichita, he's been Wichita Life. He's been, you know, a G in the space, twenty thousand plus, uh, subscribers. He just switched over to Beehiiv.

366
00:59:01.710 --> 00:59:07.490
Um, and, uh, you know, he's, like, one of the OGs and, you know, it's, it's really incredible to see.

367
00:59:07.550 --> 00:59:15.550
And honestly, there's so many folks in the club that are just starting out, and they're finding their voice, and, like, I'm learning from them all the time too.

368
00:59:15.710 --> 00:59:23.750
I think that's, like, kind of the magic of it all, is we're-- it doesn't really matter where you're on-- where we all are on the journey, we're gonna learn together. That's awesome.

369
00:59:24.150 --> 00:59:34.210
Um, how much time would you say you spend on the n-- It's hard to-- Like, is it just the newsletter? Is it the business as a whole? How much time are you spending-- Whichever makes the most sense to you.

370
00:59:34.250 --> 00:59:43.180
How much time are you spending on this each week? And then do you have any help? I think you have tweeted that you work with some VAs, but yeah, how much time are you spending, and, uh, do you have any help?

371
00:59:44.150 --> 00:59:48.910
Uh, event aggregation was the most soul-sucking experience I've ever had.

372
00:59:49.030 --> 01:00:04.810
Um, just, you know, as someone who hates social media, I had to go on Instagram and comb through all these Instagram accounts, and I did it for probably, like, geez, seven, eight months or something like that, uh, before I brought on VAs to help optimize and streamline that process.

373
01:00:05.230 --> 01:00:11.570
So I have two awesome VAs. They're fantastic. I couldn't really do this without them. Um, so whatever.

374
01:00:11.670 --> 01:00:17.510
Say it was ten hours of just kinda hunting down events all week, saving them in an Instagram folder, going on the websites.

375
01:00:17.630 --> 01:00:26.569
Yeah, you could have some AI to, to do some scraping, but I think early on you really wanna know who these businesses are, what they represent. Do you wanna partner with them?

376
01:00:27.150 --> 01:00:35.590
Um, do you wanna showcase what they're doing? So that was the biggest thing. Now, I'd say I'm probably down to, like, four hours a week just on content creation.

377
01:00:35.790 --> 01:00:46.170
You know, really kind of deep diving into a history topic, consuming a lot around it. Um, you know, we have charity of the week, you know, dogs and cats up for adoption.

378
01:00:46.230 --> 01:00:50.030
I do stuff around the astrology or astronomy, I suppose.

379
01:00:50.130 --> 01:01:02.170
Um, the history side I take really seriously and have a lot of fun with it, and it's, it's a challenge to take super deep topics and refine them into two paragraphs. Um, and then it's the branding itself.

380
01:01:02.230 --> 01:01:11.670
It's like, okay, I'm just like, "Ah, let me pop in, make this one quick graphic," and then I'm like, "Holy crap, it's been four hours." But, like, for me, that's, that's partly fun.

381
01:01:11.990 --> 01:01:21.822
Um, but, you know, I think, like, four or five hours a week all in on the content creation. The, the business side of itIt's different every week.

382
01:01:21.882 --> 01:01:37.761
You know, if I'm starting to do a, an event with a business or I'm designing a Monopoly board or making sweatshirts or working on new crew cards, which are the discount cards, it-- that's gonna be kind of a, a big kind of, uh, time-consuming, uh, practice.

383
01:01:38.602 --> 01:01:54.302
Yeah. Um, last question. So I think you've probably achieved beyond even what you expected in twenty twenty-four. What are kind of your big hopes, dreams, goals for twenty twenty-five? Honestly, nothing different.

384
01:01:54.382 --> 01:02:00.512
Just stay the path. Uh, I just wanna keep having fun. If I'm not having fun, this thing's gonna shut down.

385
01:02:00.622 --> 01:02:07.962
Um, keep kind of thinking about what's important to the community, um, and I'm talking about Catskill Crew and one eight hundred Fly Fish now.

386
01:02:08.022 --> 01:02:16.182
Start really thinking about, you know, how, how do I expand this, this holding company locally, and then what does that start looking like from a product standpoint?

387
01:02:16.282 --> 01:02:24.142
Start kind of like building the bricks to, to the yellow brick road, or I guess purple since that's the color for one eight hundred.

388
01:02:24.782 --> 01:02:34.682
Um, so laying the roadmaps for really expanding these brands beyond a newsletter, uh, outside of an inbox, you know, into something totally different.

389
01:02:35.482 --> 01:02:44.802
With, uh, The Newsletter Club, I think it's, it's really about continuing to grow, um, in a, in a sustainable way. There's a wait list right now.

390
01:02:44.842 --> 01:02:53.942
I'm slowly bringing people in, and then figuring out the best way to support all these builders and, and how I can support them, uh, rather how we can all support each other.

391
01:02:54.642 --> 01:03:05.261
Um, but I do think there's opportunities to kind of productize things from a niche SaaS play. Um, there's ways to improve kinda some of the pain points we're all experiencing collectively.

392
01:03:05.362 --> 01:03:16.262
Um, so paying attention, having fun, and looking for meaningful ways to, to monetize that are, they're really creative and, and value-adding. Love it. Uh, well, that's it. Thank you for coming on.

393
01:03:16.342 --> 01:03:28.282
Is there anything you wanna plug? You wanna plug the newsletter, the, the community, anything? Check out catskillcrew.com, one eight hundred flyfish.com, thenewsletter.club. Perfect.

394
01:03:28.322 --> 01:03:40.242
And if anyone's building local newsletters, hit me up, DM's open, happy to jam anytime. Awesome. Well, thank you for coming on, and, uh, listeners, I will see you next week. This has been the Creator Spotlight Podcast.

395
01:03:41.882 --> 01:03:55.271
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