Editor’s note: This interview is part of a series I’m doing with interesting builders in the creator economy (see previous Q&As here and here). My conversation with Michael was initially recorded in January so some of the facts/figures mentioned likely will have changed slightly. Michael also no longer shares revenue numbers publicly (because of the grifters, he says).

I’m working on a new series where I’m actively interviewing builders and founders inside the creator economy—and sharing what I learn along the way.

One of the most inspiring conversations I’ve had so far was with Michael Kauffman, founder of Catskill Crew. His energy and enthusiasm was so contagious, I found myself wanting to build out like ten of my different business ideas after the call ended.

I originally interviewed Michael for a piece I was writing for beehiiv about how to build a community through a newsletter—and more specifically, how to approach what he calls creative monetization. That means moving beyond just selling ad slots, and instead building a unique business around your brand and audience.

Michael’s been incredibly thoughtful (and experimental!) with how he’s grown Catskill Crew into a multi-six-figure newsletter, from local products to events to investing in businesses that his audience naturally asks him about.

If you want to go deeper, I’ll link the full beehiiv article here.

And below, I’m sharing the full transcript of our conversation for anyone who wants to dig into his thinking and approach more clearly.

Q: Let’s start with what you’re building. I know you’re doing a lot with Beehiiv and working on creative monetization — how do you think about building playbooks or pillars that other creators can follow?

It’s a funny world — like, I have this creative monetization webinar I’m doing with Beehiiv, and it’s just like, there’s no one playbook per se. The playbook should be modified based on who the creator is, what the niche is — all of these different things.

I’m seeing so often, like with the Newsletter Club — 100+ local newsletter creators — everyone’s just trying to take tactics that have worked for someone else and brute force them into their community. And most of the time, they’re falling flat on their face.

So I’ll say: Take the playbook and modify it to what works for you. Have you grown and built trust with your audience? Does this reflect your brand?

All these things are kind of important as we think about these pillars in the playbook and the structure.

Q: You’ve talked about why ad revenue isn’t your goal — can you share how you think about monetization more broadly?

I never wanted to start a newsletter to be chasing ads. It was never the goal. Look, some people crush it with that — it’s just not a good fit for me.

I run some ads here and there, but I also think who you advertise with is a deep reflection of your brand. For example, Catskill Crew is currently getting 100% of sponsors and ad partners via inbound.

Your best chance for sponsors is not cold calling or cold emailing. It’s creating good content people want to read and building relationships in person.

I think about how I would respond every time I got a Catskill Crew newsletter — if I saw some business that I hate or know is kind of subpar… I’m going to naturally associate that subpar business with the brand, on some level — consciously or subconsciously.

So it was always about building this distribution vehicle and leveraging it over the course of my entire lifetime. I’m not looking to sell this business. It’d be crazy to. It’s about really building and nurturing this trust and authenticity, and building a brand that is synonymous with fun and community — and then leveraging that to promote, validate, sell, drive awareness to any of these products, services, you name it.

CPMs and CPCs are already kind of in flux. When you go into niche audiences, I think there should be a multiplier on that. I don’t even want to say “local newsletter,” right? Because I think that’s not thinking the right way. With newsletters, the more niche you get, the more of a multiplier you should put on those CPMs and CPCs — if that’s where you’re going with ads.

But regardless, think of your revenue as a pie. Ads and sponsorships really do belong on there in some capacity. But if you make it the entire pie, you might be missing out on a lot of opportunity. Keyword might. It’s very individual. And again, there are newsletters that have optimized just a killer ad system and are crushing it — God bless them.

And it’s not even about a funnel. Like, remove the business jargon out of it. Just listen to your audience. And then have fun. Get creative. Start figuring out — hey, does anyone want this thing? Yeah? Cool. I’m gonna go figure out how to build it.

I think if you listen, if you pay attention, if you ask the right questions, if you read between the lines — you will find incredible opportunities to build products, services, to do something more.

Everyone talks about funnels — sure, yes — but also just like: build a community, have conversations. Doesn’t even have to be a “brand.” Just build this platform and pay attention.

Q: What do you mean when you talk about community — especially in the context of a newsletter?

That’s an awesome question. Actually, I’ve never been asked that question like that, precisely.

I think it takes many forms. First and foremost, building a community off of a newsletter — the easiest way to think about it is, we’ve been operating in a subscriber-consumption kind of structure so far. I send this newsletter out, you read it, and that’s it. You might vote on a poll — “Hey, five stars, four stars, three stars” — cool. But you’re not participating.

With community, it could take many forms. With Catskill Crew, it’s: you have a voice. You vote on the direction of where this newsletter goes. That’s authentic to me. I don’t want to build this alone. I want to make sure we’re all participating and having fun.

That works for me. It’s about bringing the community together. So we have physical meetups once a month at least — which are monetizable — but I’m happy to not make a penny on that, because it’s important for people to meet up. That’s where you hear the impact this is having — that they’re making friends, they just moved to the area, they had no idea where to go, they bought a Catskillopoly board and are having a blast.

So it’s not just about being a newsletter — it’s about being a person and highlighting other people in that community.

It could be a paid Slack community — totally works for some. But for me, that feels exclusive. That’s not my objective. I currently don’t even have a premium subscription to my newsletter. I think that changes my goals — now I’m just trying to monetize everyone. How many people are going to get through that door?

I would much rather be inclusively exclusive — where it feels like an exclusive club, but everyone’s welcome at the table. There’s always a seat for you.

And community takes many forms. It could be paid. It could be totally inclusive. But give people a voice.

Some people might say, “Hey, I’m going to feature every local artist in the area.” Now it’s community. You’re showcasing them. It’s not about you all the time.

Every newsletter’s different. If we’re talking about B2B niches — what does community look like? It’s going to be different. But it should be one of the pillars.

Q: You’ve mentioned that community can become self-sustaining — where members start forming their own relationships. Can you talk about how you’re seeing that happen?

I think in the early days, you’re going to be pushing that boulder uphill. You’re getting two people in, three people in, you’re setting up calls, you’re trying to basically grease the wheels.

It’s the same thing with Catskill Crew. It’s the same thing with the Newsletter Club. But at some point, you hit escape velocity. That doesn’t mean you step away — because I think if you step away, it already shows your objective for why you started this was flawed.

Like, it should fire you up even more to step away because you had a busy day and come back and be like, “Holy crap. This is unbelievable.”

And you’ll also find opportunities where you can add more momentum to that autonomy — through empowering those community members.

So as an example in Catskill Crew, how this is taking shape is — there can’t be just one newsletter. Even in the Catskills, there are dozens of newsletters. When you run a newsletter, your subscribers are reading that like, “Man, you left so much on the table. I’m going to start a newsletter off that.”

You can’t stop that. You should support them. I reach out to every local newsletter creator to see how I can support them — and local journalists. It’s an inevitability.

This desire to be the only one — I think it’s not inherently flawed, but it’s a defensive mechanism. You can’t appeal to everyone.

So my approach to this is: look, I’m leaving opportunity on the table. I hope someone picks it up, because I can’t cover it all.

What I’ve decided to do is — since I’m all about community and fun with Catskill Crew — how do I empower my subscribers to go create their own “crew clubs,” as I call them?

This past vote passed by 94–96%, and now I’ve run a survey for crew leaders to come on board and run different clubs. Those could look like yoga, fly fishing, hiking, crafting, art, book club, cooking classes — you name it.

My job is basically to support all those folks — through organizing the meetups, sharing the good word. There’s no charge for this.

There are businesses already coming in saying, “Hey, we want to do a ceramics night at our bar — $25 a ticket.” And I’m like — you know, where is the line of, “this is just an event” and “this is a club”?

Well, that’s not really the point.

This is an event for people to get together around a theme — cool. If you want to be a crew club leader, that’s awesome to me. If you’re going to be a conduit within the community to bring people together — whether you’re a business or an individual — hell yeah, you have all my weight behind you.

In the Newsletter Club, we’re seeing the same thing — people are connecting through DMs, meeting up in real life, starting to work together, building tools. We have some great folks doing amazing things together.

It just takes some effort to start building that. And again, it all comes back to — do you actually care? If you actually care, you’ll find a way to make it work.

Q: Let’s talk about revenue. A lot of people assume you need a huge list to be profitable. But you’ve shown that’s not necessarily the case. What does your model look like?

I completely agree that it’s quality, not quantity.

When you’re purely ad-driven, it’s quantity. When you’re looking at it from a creative monetization standpoint — like, “Hey, I want to create things and use this newsletter as a launching pad to monetize in different ways” — then it’s all quality.

Give me 100 engaged subscribers over 10,000 that don’t care what you say.

So first and foremost — are you building a quality audience, regardless of what your niche is? Are you empowering them with a voice? Are you connecting them? Do you care?

Let’s say all those boxes are ticked. You have an audience of 1,000 subscribers who are diehards. They open every single email you send. You’re listening and paying attention to them.

Now we get into the nitty gritty.

Coming back to Catskill Crew — which is the only one I can speak definitively about — last month was like, I don’t know, $57,000 in revenue. Something like that. I’ve got a bookkeeper now. I hate numbers. I like the creative side.

I went months without really monetizing early on — saying no to advertisers, taking $100 here, a couple hundred bucks there, but giving away ads to businesses I really liked.

Look, I understand some people need to make a penny here — they need that $100 to support growth. Totally respect that.

But if you’re looking at the long-term plan — like, “I’m really trying to build this newsletter, not flip it or just get to 100,000 subscribers to turn on the ad engine” — then nurture that audience. Really care for it. Protect it. Protect that brand you’re creating.

Once you get to the point where you’ve asked enough questions — now it’s time to put on the creative spectacles and start f*cking around. Playing with different ideas.

You have no idea what might work.

Like for me, the Catskillopoly board game? That was a joke. I was sitting in Taos, New Mexico, drinking red wine during a storm after fly fishing all day. They had a Taos-opoly board, and I was like, “This is horrendous.” It was covered in businesses I didn’t know. Very Monopoly.

So I was like, all right — let’s see how this goes. I asked the audience, they voted approval. Sold 500 units in like 17 days.

All right. I pulled the trigger on 1,000 units. Might bump it to 2,000. It’ll take a while for those to get here, but I have wholesale distribution now through local businesses. I have the trust of my subscribers — if they’re going to spend $60 on a product, they know it’s going to be super high quality.

I said no three times to my manufacturer until they got it right. I’m not after the quick buck — I’m after the trust.

I’ve got three other board games in R&D right now. It’s the silliest way I’ve ever made money — but it’s fun, and it’s community-oriented, and it’s on brand with the Catskill Crew identity.

There’s discount cards — those were a decent business, but really, that was marketing exposure. Some days I get negative CAC as a result.

I get messages from subscribers all day long — especially when it’s warmer — “Where can I go fly fishing? Do you have any good guides?” So I invested in a fly shop because of that. When I promote that business, I’m monetizing it — but I know those are good guides.

People ask me, “Where’s a good Airbnb I can stay at?” Makes sense for me to just buy a piece of property and build a beautiful Airbnb right there — that I can use and market within the newsletter.

Everyone’s business is going to be different — geography, brand, audience, niche — all these things. When you start doing like a multi-layered Venn diagram with four circles, you’ll start finding some opportunities within all of them.

Then it’s about: which ones can I actually deliver on?

It doesn’t matter if it’s an opportunity — if you can’t deliver on it or don’t care, then just leave it. Do the things you think you can actually deliver on.

Q: Who else do you see doing this kind of creative, community-first newsletter model really well?

I think everyone’s doing it a little bit differently.

What you’re seeing is: the majority of people have been very ad-driven. And they’re looking at local newsletters with news.

I’m really trying to build a local brand.

I don’t have any news in my newsletter. Okay, yeah, I have astrology. Or what’s happening in the night sky. That’s my version of news. You know, “The Seven Sisters are next to the moon this week.” That’s my breaking news.

Some people like Naptown Scoop, of course — he’s working on it. He’s an incredible ad machine, right? Crushing it. I can’t do that. I don’t have any interest in doing that. Deep respect for that.

Then you have Jazz at Winnipeg Digest — he’s doing a great job of leveraging Instagram content plus his newsletter, and now leaning into being more of an event and marketing partner for things. Love it. Fantastic.

I think the whole idea is: find what works for your skill set and your market. Don’t try to jump to conclusions. Build that audience. Nurture it. Listen. Pay attention. See what opportunities come to you — and which ones you actually care about.

If you start chasing in every direction, you’re gonna be a dog chasing its tail, and you’re going to stand for nothing.

Don’t try to get over the horizon. Just take it one step at a time.

Q: You tweeted recently that original reporting and community are a “moat” against AI. Can you expand on that a bit?

AI is coming for everyone. It’s an inevitability.

These things are going to be spun up. You’re going to have agentic systems running swarm agents working together to source news and duplicate your voice — and chip away at your market share on big markets and small markets.

In my opinion, I don’t think content is your defensive moat anymore. I think it hasn’t been for quite some time, actually.

You need to do everything you can to figure out: how do you build brand loyalty?

I think news-forward is always going to be the most susceptible.

If you look at newsletters already, the majority are looking at news websites and simplifying. They’re taking 10 articles from across the internet — from local publications — and aggregating. Fantastic. But an AI agent can do that faster and easier than you.

So you need to add your voice and your personality — layer it in there. So when they get a message from Taylor, even if it’s the same articles, they like that you’re local. They like the connection to you. They like your take.

So from a content standpoint, it’s about brand voice.

But I think you can go deeper. AI can’t compete against building community.

So for the ones out there interested in building community — prioritize that at all costs. Because those agents aren’t going to be able to do that.

Q: Yeah — I think about this all the time. Do I even have a job in five years? It keeps me up at night.

I think it’s about the voice, though. Right?

Traditional reporting — how do you stay relevant when content is so… not even plentiful, but easily duplicated. Stolen. When reach is made easier. When you spend a week writing this beautiful article, and an AI agent — or a swarm of them — takes it, modifies it, ships it out to a million places, maybe doesn’t even give you credit.

So it’s like — how do you build not even a moat, but a magnet that brings people in?

That’s kind of the flip of the script. We’re always talking about keeping people out. But I think it’s: how do you keep people in? How do you attract and keep them coming?

Q: I love that. I’ve been thinking about creators as curators — and you’re kind of curating what your community needs to know. That seems like a future-proof approach.

I agree.

And I think you combine that with…

I heard this from a subscriber the other day, which was just the fact that when they get an email from Catskill Crew, they know it’s nothing but good vibes. They know it’s going to be very positive.

And they actually recognized how much effort that takes.

Negativity is easy — especially in the world we live in today. Those gravitational forces are so significant. And I protect my community and that voice at all costs.

There’s more than enough to talk about from a negative standpoint. That’s not what this is about.

I want this to be a very positive interaction space.

In the Catskills, there are real challenges between locals and wealthy weekenders. Mountains are getting bought out by the ultra-rich. They’re putting in helipads. It is very charged.

And many people have asked me to cover that. Many people have offered to pay me a lot of money to put in good words about a new development that’s going in.

And I’m like — no.

I don’t want to touch that. That’s a toxic topic. And it’s just not what I represent.

So yeah — positive vibes go a long way.

Q: So what’s next for Catskill Crew?

Crew — purchasing commercial real estate, investing and supporting in local entrepreneurs via my local hold co. Working on product line and local wholesale distribution. Writing a book on history / nature. Testing a premium subscription model that is physical versus unlock newsletter content. More events. More community. Exploring unique local software.

Club — relaunching the newsletter club site and continue to slowly grow the largest community of local newsletter operators.

Other — testing new newsletters, some local franchise models. Aka screwing around :)

Here’s where you can find Michael: