Doug: Hello, it’s Doug here. Wanted to pop in before I send it to the interview and let you know, I kind of put together a mini series on local newsletters. They’re local brands overall. There might be social media as part of the mix, but mainly they’re email lists targeted at a locality. And the theme. There’s a couple of things that are pretty surprising, right?
Number one, the interviewees that I’ve talked to a lot of times, they’re pretty fresh into it at now. I know local newsletters have been around for a long time. There’s some established players, which I think some of the newcomers are learning from. But the thing is these guys that I’ve talked to so far specifically Jas over at Winnipeg digest.
And today, Michael Kaufman at, uh, the Catskill crew, they are fairly new to the newsletter world overall. And this person that sort of triggered me to look at this stuff a little bit more, uh, two folks good friends, Shauna Newman over at skip blast. So. Talked to her many times and she’s working on her own newsletter, but she hasn’t got the same traction that Jas and Michael have.
And the other person is Brooks Conkle. He has the mobile something. I get confused with all the names out there. We’ll put it in the show notes to make sure we give Brooks a proper, a proper call out here, but it’s been interesting because it sounds like you can get these local newsletters going fairly quickly.
Like many business models, there’s different focuses that you can have and different monetization that you can aim towards and. Like most things, it might not work out how you think, but usually you’re able to pivot and make it work out. And yeah, Michael’s doing awesome overall here. And Jas is doing great.
If you missed that interview a couple of weeks ago, the thing that shocked me with Jas is he’s 23. So he’s, he’s young as an entrepreneur, but he’s doing really well with execution. And I think I even mentioned in the intro of the interview, like Jas and I talked a little bit after the interview ended and he was asking like really smart questions as I’m a, Well, now an elder.
So he was like, ah, what do you think of this? What do you think of that? And it’s cool. Like when you do these interviews, like you get to chat for a little bit afterwards. So anyway, these are cool to learn about. And whenever I talk to someone, like they’re very encouraging for me to start something.
And I am trying not to start new things, but they are so enthusiastic and they’ve Gotten traction really well, and it does make me consider starting a local newsletter, but I have I’ve stuck to my gun so far and I’ve been lazy, which is obviously easier to do. So this is a great interview. Hopefully I’ll be able to chat with Michael again in the future with Jas also, and just hear like maybe every six months or every quarter, like.
Check in and see how it’s going. I think I had, I had a fun time with the conversations and I hope that comes through in the interviews. But usually if we have a good time, like folks are happy to come on back, back on the show and everything. So if you have any specific questions, you know, Michael and Jas have.
You know, mention how you can get in touch with them. But if you want to, if you’re like, I don’t remember, uh, you can shoot me an email feedback at Doug dot show, and I could route it to them for the next interview, usually that’s how it’s going to work. The other thing I hope that is on the horizon is doing more interviews with SAS founders.
So a few weeks ago, I talked to Zach Welchel, who I met at a conference a few months ago at this point. And we, you know, we had a nice time meeting in person is a great way. To establish those relationships. It’s a little bit it’s more fun, more personal, of course. And the fact that, you know, people travel to a conference, like they have some skin in the game and you’re roughly trapped at a hotel.
So you’re just kind of hanging out anyway. And he has a cool company, which he decided to sponsor the show a little bit. So shout out to my budget coach. And I’m not big on. I don’t love following a budget myself, but there’s a lot of different ways to do it in a budget. Honestly, it can set you free as far as setting up a system Moving forward and seeing good consistent results all the time I do have a proper ad read and if you’re wondering where does my money go?
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And I talk about this with, you know, business projects or, or really anything like you can have a plan, but the only thing we know about the plan is it’s not going to be quite right. And you’re going to have to be flexible and adapt. And since my budget coach is both online and an app on your phone, you could budget on the go.
And it can even sync transactions with your bank account. My budget coach is a zero based budget model, which is like a digital envelope system. And if you don’t know what that is, you can listen to the interview with Zach, but overall, this simplifies everything. It makes it very easy to understand, and it’s very straightforward.
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or follow the link in the description here. And it’ll send you right over. So I want to thank my budget coach. And if you’re curious more about hearing the specific interview with Zach, we’ll link up to that. It was just a few weeks ago when we did the full interview. So I think now we can send it to the interview with Michael Kaufman from Catskill crew.
And I mean, he. He shares so, so much. I mean, these have been a masterclass for me and, uh, just marketing and working on a local newsletter. So let’s get to it.
Doug: Hey, what’s going on. Welcome to the Doug show. My name’s Doug Cunnington. And today I’m talking to Michael Kaufman and Michael, welcome today. I think we have like some cool intersecting stories. You actually know sort of the area that I live in, which is the front range here in Colorado. Where are you out of?
Michael: I’m in Catskill mountains. So, probably a little less snow than you have right now, but we still got it. And
Doug: we’re talking local newsletters today and local branding, but as we were doing like pre interview chat, which I kind of like to do, especially we haven’t met before, so this is like within five minutes of us meeting or so just hearing about your history with startups in various industries, your kind of desire.
To just bootstrap and keep things kind of simple. And that’s what led you, I think, to some of the newsletter stuff, but just to get to know you a little bit more, like what, what was your background? Did you go to college? What, what did you study? What were those first couple of years looking like when you got out of school?
If you went.
Michael: Yeah, terrible student. I can’t fake something. You know, I can’t pretend to care if I don’t actually fundamentally care. So I was a history major, which has always been interesting to me. And about junior year in college, I started a beverage company. We were making this thing out of our apartment in, in the North end in Boston.
And we got a call from an investor and he was like, Hey, I tried your product. P. S. We have no idea how he ever got the product. He was in Wisconsin. We still don’t know. And he’s like, send me over a business plan. And pitch decks were not a thing. And it was like 40 page business plan. So I was like, absolutely.
No problem, Tom. I’m on it. Went on Google. I was like, what is the business plan? I was like, holy crap. I need, I need two weeks. And, uh, we raised some money. I was naive which is, Experiences what you get after you need it. We undercapitalized, but we had a killer product partnered with folks behind you know, Sobey and Arizona and Ended up having an opportunity to sell to Bacardi and and realized we got in bed with the wrong people for capital raising learned some tough lessons fast and pigs get fat hogs get slaughtered and Shut it down.
Ended up working for Jay Walker, who’s the founder of Priceline, prolific inventor, 300 patents, and, uh, He just acquired TedMed and affiliated to TED Talks, and This was when Fitbit, Nike, FuelBands, all those fitness trackers were taking off, and, I was like, holy crap, you know, like, I’m gonna have a six pack and be able to run ten miles, finally in no time, and, Within two weeks, no one wore them.
And I was like, what the hell happened there? And my hypothesis was that the hardware is good. The software of tracking 10, 000 steps every day sucks and is pretty subpar. So again, naive enough to start a healthcare company building games on top of health data Ended up consulting for big healthcare, which pays well and is probably the most boring thing you could ever do in your entire life.
And then rapid fire, a bunch of little startups in between back into the beverage industry, recapitalizing, relaunching beverages. But yeah, startups are, are everything. It’s all I know how to do is kind of sit around, think about ideas and try to make them a reality.
Doug: And we’re talking newsletters today, but I do want to backtrack.
So what was the beverage originally?
Michael: The beverage originally was Ember. It was a detox beverage. So it was actually like Look, I was a college kid who experienced terrible hangovers. My hangovers were worse than the normal person’s. So you can imagine what they are like 15 years later. Debilitating.
Send me a doctor and a priest and a rabbi after a glass of wine. And yeah, we, we had the opportunity to partner with some really, really bright people who left traditional pharma and started Holistic Health Company. And we were doing this really just for our own kind of I don’t know, it was like a passion product, project.
Could we solve the hangover? And I always said like, ah, we put a man on the moon, of course we could solve the hangover. And one day, we Concocted this killer beverage. I mean, there’s still nothing on the market that, you know, holds a flame to it. And it was incredible. It’s a really tough industry because you’re you’re fundamentally changing behaviors Especially when someone’s like all they care about is greasy pizza at the end of the night.
You’re like, hey think ahead about tomorrow so it’s a tough industry in terms of behavior change, but Yeah, it was, it was a lot of fun. I learned a lot. And I think the most exciting thing for any entrepreneur still lights me up and charges me is when you have an idea and you see it become a reality, whether it’s a digital website or app or physical product going down the manufacturing line, you’re just like, I can’t believe we’re here.
I can’t believe we did it.
Doug: Very cool. So when did you start the local newsletter? And you can share what it is and we’ll dig into you know, the business model over all in monetization, growing the newsletter, the grind and all that stuff. But what was the origin story here?
Michael: Yeah. Still I was, I was building a startup.
In the outdoor space so, you know, it was an outdoor hospitality company. And it morphed over time. We started partnering with some, some legends in the hospitality space. And I started seeing this thing get more and more complex and capital intensive. I mean, we went from raising 300, 000 to raising 20 million and there was no end in sight for that journey.
And I just felt the headwinds. I wasn’t excited about the direction of the company. Getting on a call every single day to Capital Raise, update pitch decks, it removes you from the product, it removes you from, for me, what passionately lights me up. And I finally got burnt out and I got a bunch of fly rods back there on the wall and I packed my car with fly rods, went out west, Colorado.
Utah, Idaho, Wyoming, Montana. And I was like, I want to build something. I don’t want to have to capital raise ever again. I want it to be community focused and I’d never built a newsletter before, but I knew I could do it. I knew the tools were out there and I knew I could probably create something that had a stickiness factor.
Um, and I kind of was looking at where are the opportunities and they’re infinite. And so I decided to go with local newsletter. I live in the Catskill Mountains. It’s a really interesting place with proximity to Manhattan. A lot of weekenders, a lot of city folks who’ve moved here full time, myself included, and a lot of kind of old school locals.
And the big thing for me is like, I hate social media. Finding events are up here is really, and everywhere, is really hard. And, you know, Zuckerberg’s algorithm has, has really messed with, with small business. They have no conduit to the local community anymore. As I’ve heard a trillion times, they used to be able to post for free and get massive organic traction.
Then they’d have to pay to get them that massive traction. Now they can’t even pay to get what they once got for free. And so I do believe that local newsletters fundamentally play an important part in a community for the local businesses and the community itself. And it does represent kind of this new form of local media as, you know, local newspapers die out.
You know, there still needs to be this backbone. And so, you know, I started Catskill Crew really highlighting the events and then, you know, leaning into what lights me up, which is the history and the culture and the community. And I was like, holy crap, like first newsletter out like 100 subscribers.
This is nuts. My mom was number one. Thanks mom and then it grew to a thousand and two thousand and three thousand pretty organically and we can get into kind of the growth tactics there then, you know, I threw some some fuel on the flames and uh pumped some money into ads and Now we’re sitting above 10, 000 a year after making it.
And you know, that’s really special. Uh, it, it, it lights me up.
Doug: That’s awesome. And so there’s 10, 000 subscribers and you’ve been running this about a year.
Michael: Yeah. Yeah. The seriously less than a year. I really kind of. leaned in in a, you know, around Christmas time last year. So, you know, now I’ve gone from about 5, 000 to 10, 000 in 60 days.
Open rate continues to go higher. Monetization is, is keeping pace there. So, you know, even with the growth, I’m maintaining kind of the consistency the authenticity that I think got me where, where the newsletter is today, rather.
Doug: Got it. Okay. And. Can you share revenue numbers? And you don’t have to, if you don’t want to, but people want me to ask.
So whatever you’re comfortable sharing or not sharing is great.
Michael: Yeah. I mean, you know, I, I am the worst accountant. My, my accountant finally got me on QuickBooks because I’m terrible at tracking this stuff. But for example, I did 10, 000 roughly in the last seven days. You know, I think I’m on track to do about 60, 000.
In the next 45 days, and, you know, I think the big thing here is like, revenue comes in waves. Look, everyone’s kind of journey is different. Everyone kind of has, everyone who has a newsletter or a local newsletter, they have different approaches to monetization. Some are just, you know, an ad each time.
I say no to advertisers non stop because I think it, it actually devalues the experience and my brand, and I’m really trying to build something way more than that. Just a newsletter. I’m trying to build a local brand, a local holding company. And so I spend a lot of time, I kind of bucket revenue in, in, in two different kind of structures, two different buckets.
You have traditional monetization, which is very much just, you know, ads sponsors, and then you have creative monetization, which is, you know, for me, it’s discount cards like my Catskill crew card here, which is just a discount card with 10 local businesses. I sell these for 25 each. The community voted that they wanted them.
The community priced them. I’m doing custom Monopoly boards that are being manufactured right now. So my cost is about 9. 50. I’m selling those for 59. 99. I do merch drops. I do events. I’m kind of all over the place. And I think that’s what keeps it interesting for me. And I think that’s also what keeps Subscribers coming back, they know it’s not going to be just laden with ads.
It’s, you know, this is meaningful, fun stuff that engages the community that highlights this area. So revenues all over the place. You have months where I might make a hundred bucks in months where I’ll make, you know, 25, 000.
Doug: And it’s so early to in, in the growth trajectory too. It’s like in whatever, another quarter, You could have like twice as many subscribers, like who knows the sort of sharing or the growth patterns and that sort of thing.
So it could be like, quote, underpriced currently. And like, yeah, so I understand the waves. It could be pretty crazy.
Michael: A hundred percent. And I think like, this is actually something that’s very interesting because I realized like at some point I’m going to cap out at what I can charge my local community.
So for an ad, let’s say I think CPMs. should be thrown out the window I might be the only person in that camp. I go to every business with, you know, understanding what they’re trying to sell, what their goals are. And then I put together a custom package based on what I think is a fair price. If they come back to me now, Michael, I can’t afford this.
I’m like, cool. What can you afford? Let’s structure something around that. That’s custom because When they sign on with me, it’s an endorsement. I am, you know, that’s why I have to say no all the time because I want, when I partner with a business or a product or a location, I want it to be a full endorsement and partnership.
And I think there’s only so much you could charge. Small businesses now you can lean into the higher higher ltv businesses be that architects be that doctors dentists hvac. Yeah, you could charge them a little bit more But that’s why I think like as your subscriber Numbers grow it’s a really good opportunity to examine that and then see hey How can I actually monetize the subscribers in and i’ll say this to exhaustion in an authentic way?
Like if you’re trying to just like do a money grab You’re not going to win in the long term. You might make some money for sure, but you’re, you’re, you’re leaving a lot kind of on the sideline. And so, you know, I very much focused on subscriber LTV versus, you know, advertiser revenue that might change, but that’s kind of how I’ve gone into it from day one.
Doug: Okay. So let’s back up just a little bit. How big is sort of the community population wise that you’re serving or attempting to?
Michael: Yeah, it’s massive. I think I have a pretty unique challenging geography. So the Catskills people will drive two hours from one side to the other. We have like 450, 000 under the population of the counties that I cover, but I also kind of bleed outside of that.
So, you know, I’ve gotten some feedback in the past. It’s like, Hey, that event’s not in the Catskills. No, it’s not geographically in the boundaries of the Catskill National or the Catskill Forest. But the idea is that, Hey, if you live here. Yeah, you could travel 20 minutes outside and it’s still an exciting event or it’s still something great to do.
So, you know, I think there’s, there’s pros and cons to kind of the expanse of that geography versus, hey, I’m covering a suburb or a city. But yeah, it’s a, it’s a massive region. It can take three hours to drive in, in, from, from east to west and two and a half hours from, uh,
Doug: And you alluded to it earlier, but people go on vacation there.
So it’s even, it’s even bigger than that because people might hop on the newsletter. Maybe they have a vacation home there or they go there, whatever, every, every holiday season with their family or something. Is it that kind of place?
Michael: Yeah, for sure. I mean, even, even less than that. We’re, you know, to get to the Catskills from New York City could be an hour and a half.
Just kind of like get into there. It’s about two hours and 15 minutes to where I live. So people are coming up here all the time. I have a ski mountain, you know, a quarter mile down the road. So people are coming up here all the time. The only downtime from a, from a vacation or standpoint and tourism standpoint to April, we call that mud season.
It’s the only kind of time you don’t really want to be up here. So yeah, I mean, I think like the, from the vacation or standpoint, it’s a whole other opportunity. And as I kind of think about. And have conversations with local newsletter builders. They’re always talking about, I’m going to take the model and then expand to a different city or different geography.
There’s nothing wrong with that. However, personally, I think it’s better to go deeper into a community. So, okay, you have your local newsletter on events. Now you have one about culture, then history, then for vacationers and tourism, then for parents each one of these, you’re, you’re compounding the brand trust that And you are not starting from scratch in terms of rebuilding an audience and I think if you’re looking at it from a subscriber ltv standpoint as well, like You’re just creating such a massive kind of wormhole for monetization.
Each one of those can, can really produce significant numbers if you understand the subscriber problems. And do not guess what the subscriber problems are. You have tools like polls and surveys. Ask the right questions. Gain the insights. Build stuff they want. Invest in local businesses that you know these people want.
Own a small percent, promote those. Like it’s incredible what’s possible here.
Doug: Let’s go to growth and how you started getting the first subscribers in the beginning and what, then what you’re doing now, of course.
Michael: Yeah. I always kind of think you can, I tell folks that you should be able to get about 500 to a thousand subscribers in 10 days.
And it sounds without spending a penny, it sounds aggressive and it is. But. I think the most important thing is a lot of, in order to grow, you need a brand that resonates and that speaks to that community. And so spend time on the branding because most newsletters have such subpar branding. It’s really not hard to stand out.
You have tools like Canva, mid journey, you name it. It’s never been easier. And so once you lock that in, Start promoting events. For example, I mean, whatever your content niches define that events are always a winner from what I’ve seen and what I did was I would highlight, I don’t know, anywhere from 30 to 100 events per week.
It got crazy at one point and I’ve throttled down since then for my own sanity and probably my subscriber sanity curation is key and what I would do is then post that on instagram I would tag all those businesses that would make them look really good in these posts to the point that they wanted to share it And I grew, you know, over 500 subscribers in 10 days.
And I kept that up for quite some time until, Ah, again, I just hate social media. And so I kind of stepped out of that world a little bit. I dabble and I play there, but I’d rather put my efforts elsewhere. So you can grow organically quite easily through social media. Riding the coattails of the local businesses by making them look good, creating content that’s very shareable.
From there, find communities like, Reddit. A lot of folks have had a great amount of success just posting events or news. And then at the very bottom being honest and just be like, Hey, if you want the entire list, subscribe to my newsletter, it’s totally free. You can unsubscribe anytime. You have apps like the ring neighbors app, same opportunity there.
Facebook groups don’t go in and just be like, subscribe, offer some value. And then just humbly, like kind of put a little nest egg there that says, Hey, if you want to learn more. We’re here. So that’s the easiest way from an organic standpoint. You, you get out what you put in. And, and I, I kind of remind everyone spend time on the brand, make it look good because it’s going to resonate with the subscribers.
You’re going to look more premium. It’s going to attract more advertisers and the businesses you promote are way more willing to promote your newsletter because it looks legitimate.
Doug: So did you have much of a following on Instagram Zero.
Michael: Literally, I have zero posts on my personal Instagram. I’ve never promoted Catskill Crew on my Instagram once, to my own detriment, right?
Like, it’s just not really how I use it. And so I’ve grown this thing organically to a couple thousand subscribers before I kind of turned on the Zuckerberg ad machine, which, It works, you know, and I tell everyone to start earlier cause I started late. You know, and the more money you invest into this, the more growth you have, the quicker you can recoup that investment through charging more for advertisers or again, monetizing your subscribers.
Doug: And I see over on Catskill crew Instagram, you have about 9, 000 followers there. So that’s a respectable number. So if you do, you know, share some. Things now people are like, Oh, like this is a sort of a prominent social profile here in the community, right?
Michael: Yeah, it’s funny because there’s kind of a, when you’re building a local newsletter, you then have social accounts and you’re like, how did these fit in to what I’m building?
And there’s some local newsletter builders who have a higher social following than they do newsletter. Jas as an example, he’s done an incredible job, you know, monetizing his social and then having this additional newsletter. kind of as a tool in his toolbox for, for monetizing. For me, it’s always been about the newsletter growth.
And I think even when you’re small, it feels a little kind of underground. Like if you’re, if you’re following Catskill Crew, like you’re in the know. And then I realized, you know what, I’m not monetizing or promoting any businesses on Catskill Crew’s Instagram, but it is my storefront. It is the numbers that the businesses can see that unfortunately are kind of a vanity metric and legitimizer for the newsletter itself, because they can’t go into my beehive and see what my metrics are.
They just kind of have to trust me. And so I started saying, okay, you know what, Hey. Don’t invest too much time and effort into the social standpoint, but invest enough where you look legitimate.
Doug: Okay. And that’s the perfect way to put it. Our, the way we were introduced is our friend Shauna Newman and she has a brand that she’s working on in the Las Vegas area.
And one thing that Jas pointed out, cause I asked him, Hey, what do you, what do you think her issue is? Cause she’s not, she hasn’t been able to convert as much as she thought. Just, Over the last six months or whatever that she’s been working on it jazz Proposed that it might be just like a low social following So it’s harder for her to like close deals and that sort of thing and it makes sense to me So what you just mentioned sounds just right.
It’s like invest some time. It helps you get that quick start As well. And of course the, I mean, the businesses are out there trying to share stuff, trying to get traction. So even if you have no followers, if it pops up on their feed, they’re like, Oh, wow, someone’s paying attention to us. Right. So simple.
Michael: Absolutely. Absolutely. And I think every demographic, every geography, you know, who are you targeting, who are you speaking to? Are you going for a younger audience? Are you going for an older audience? Are you going for, you know, parents? You want to define that and. And then just kind of let destiny take the wheel.
So I was targeting a younger audience. I don’t really have any Facebook presence because I don’t have a Facebook. I don’t want a Facebook. And you know, I do run meta ads, which has attracted an older demo. So I do get the AOL emails now flowing in. I’m like, right on. But you know, who are those folks?
So I was targeting, targeting a very young demo in terms of like, I’d say 25 to about 45. And then it just started naturally kind of attracting other people, especially as I highlight the history of this area, which really resonates with people. The history of the Catskills is so rich and deep. And you know, it’s funny because like, I don’t really cover news.
I cover like the history, the culture, and the people. And then the events. That’s my primary bucket. And so all of these kind of resonate with different people. Some people aren’t really looking for things to do. They just kind of want to know a little bit of history. Like this week, I have some of the ghost slopes of the Catskill mountains, the first ski mountains, which have just kind of eroded away.
They shut down and have been consumed by the mountains again. And like, That’s really exciting. The history of fly fishing in the area the history of hunting, the old hotels that were kind of the original vacationing places of, of, of America. And so, yeah, I could go into a tangent on that, but to, to focus back.
I think it’s very important to understand your demo and then how to speak to them. What is that voice? Some for me, I’m just myself, which is makes life pretty easy. But you know, if you have a different demo, you might have to kind of, you know, Bob and weave till you figure out what resonates with them.
Doug: One thing I noticed with my audience over time is you tend to attract people that have a similar background because you use a certain vocabulary. Your perspective is a certain way. So I came from like the I. T. world and, you know, tech and that sort of thing. So a lot of the audience. You know, fits that sort of background, not everyone, but I mean, the majority, it makes it much easier, like you said, because then I could just do whatever I want.
And then the audience kind of picks itself instead of me trying to force what I want. It sounds like. You just talk about stuff you want to talk about. You’re an outdoorsman, right? So fly fishing, travel, the history, like it all comes together. Um, what do you, do you sort of like check yourself? Like, Hey, am I just being too self indulgent or do you just like, if I’m interested, other people are interested.
How do you set that bar? Right.
Michael: It’s a funny thing, man. It’s really I could go kind of in a couple different directions here. People respond very positively to just me in terms of like how I write. It’s a very friendly, it’s how I speak to everyone. It’s friendly, it’s approachable, it’s not too serious.
It’s hopefully rich in value. Not all the time. And so I think like, one, it’s that tone of voice, and it’s kind of, it stands out in a sea of kind of just crappy inbox inbox kind of spam. Two, You know, I kind of ebb and flow. Every newsletter is a little different. Again, I have this primary bucket, which is events.
But before you get to events, I have kind of, whatever speaking my interest, I’ll tell a story about how I went out four days straight trying to catch this one rainbow trout and got skunked. And people love that. Or I’ll talk about, you know, deer season is opening up and what that means. And, you know, wear your blaze orange so you don’t accidentally look like a buck.
I’ll talk about the history, I’ll talk about, you know, some of the famous artists in the area, alive or dead. And I think like that kind of playfulness and adventure is kind of part of how I live life and how I kind of write my newsletter. I run surveys all the time to understand which Which content buckets resonate?
What do you want to see more of? What do you want to see less of? And people love kind of the outdoor stories of you know Me getting lost in the woods or hiking up this mountain and not bringing it off water or you know, whatever it may be And I think it’s also kind of a gateway for them to experience these areas to understand what fly fishing is like to understand You know what hiking giant ledge is like in the middle of winter and oh, you know what?
I never hiked 45 minute drive. Let’s go check that out so I think it’s it’s holding someone’s hand and bringing them into my world And you don’t have to be an angler to like appreciate Fly fishing. There’s a reason why I think the the most quantity the richest quantity The heaviest quantity, I haven’t had enough coffee of of, of literature has been written about fly fishing because it just resonates with people.
It’s not about catching the fish. It’s about getting outside. It’s the least efficient way to catch fish. Use a worm. Don’t use a fly. It’s harder.
Doug: You know, I, I never got into, uh, well, fishing in general, like my family just, we, we didn’t fish. But I lived in Bozeman for four years, which is one of the, I mean, that’s like a world class place, right?
You got the Madison, Madison,
Michael: East Gallatin, the Gallatin, the stone. You’re you guys are set the highlight. Highlight Creek, which are, yeah, I’ve fished at all, buddy. It’s amazing.
Doug: It’s a beautiful area, but I would get out and like, take some photos and stuff, but I would see, yeah, see guys in the water. And I mean, they’re just having a blast.
There’s no one around. There’s like a elk, a buck right behind. I mean, it’s just absolutely beautiful. And I’m like, I don’t know why I didn’t get it, but it was, it was never about the fish, right? It was like, you’re out about
Michael: the fish. It’s hard to remember the problems we all have when you’re standing in a river.
Yeah. Um, and it’s impossible to remember them when you have a fish on the other line. Impossible. It’s, it’s an amazing thing. So I think, you know, highlighting the culture, I think what, I don’t want to say like I represent the Catskills. No, that’s crazy. But I just live a life that’s very much harmonious to the Catskill mountains.
And I think that resonates with a lot of people. And, you know, if you think you, your lifestyle and your voice will resonate with people in your area, lean into that. If you don’t think so. Don’t or or test it. It’s it’s risk free. Worst comes to worst. You lose a couple subscribers You’re not gonna have a mass exodus unless you do something really unholy but Yeah, I I would advise to stay away from like just having ai or a virtual assistant write your content.
Look It can help you it can help kind of fine tune some of the content you’re, you’re trying to put out in the world, and, but you’re gonna lose that special touch. Like, I, I write every newsletter as if I’m talking directly to one of my subscribers. How I write is how I speak, and I think that’s a big reason why I’ve been able to kind of sustain this growth, and, you know, really reduce the churn as, as, as it grows.
Doug: How many emails do you send out?
Michael: One a week every Tuesday and goes out usually around 3 p. m. Eastern, you know, 50 percent open rate in the first hour. So like, you know, I want it to be like, Oh, Catskill crew email. Let’s check out what’s going on. I don’t think there’s anything wrong with sending more.
There’s folks in the newsletter club, which is the community I run for local newsletters that send out four newsletters a week. For me, it just doesn’t work. That cadence is always open to be reconsidered. I’ve looked at writing another local newsletter based on the feedback from subscribers around real estate.
So I was going to add that on Thursdays and I’ve been hesitant to pull the trigger on it because I think in real estate, You start entering into the world of money and you know, okay, you have a property that’s worth 300, 000. That’s not that great. 600, 000 nice. And then a 2. 5 million house. And it’s like, okay, this is real estate porn, but I think it, it, it can erode at kind of the good vibes only.
And you know, working with realtors has its own challenges. I think, in general, there’s a misalignment between me and them, which is, yes, everyone needs to make money, but, you know, you’re just looking for the next sale. You want your advertisers, you want, as an advertiser, to just be front and center and to find that next sale or, um, you know, new client.
I get it. But It’s just a little abrasive to kind of my, my, my likeness that I’m able to have fun with.
Doug: You don’t have any real estate agents in the family. Do you? No, no, but I got some friends who are them. Okay. Don’t tell them. Yeah. And I have a lot of friends. Yeah. It’s the worst. Yeah, the, the incentives are all misaligned or horrible to work with.
It’s like a used car salesman. They just sell houses, you know,
Michael: when I, when I bought this house, I 2022. I’ve been up here for longer. I put in an offer and the realtor responded back to my realtor and was like, can you please tell your client we’re only accepting serious offers? And I was like, Ooh, no, same offer.
I’m doing the same offer. And he was like, congratulations. You got the house. And I was like, I was like, I respect the hustle, but that is a dirty tactic. And so, you know, I think like. In terms of like my good vibes only, I don’t touch politics. I don’t really touch anything that is, is really negative. So, you know, we had forest fires up here very recently that didn’t make much news and I didn’t really want to get into it because look, people are going to get that news elsewhere.
I want this to kind of be an oasis of, of, of community, of bringing people together. And I think that that maintains kind of precedent as I move forward.
Doug: So, uh, Going back in your, your story here, you, you’re a good communicator. You, you raised money, like you had to sell. You were in, you know, a few different startups, different world.
Did you have any experience like sort of working online? Like a lot of people are looking to get started with this as a side hustle. Did you have any websites in the past or did you do any marketing writing? Aside from the, like I said, of course you’re raising money. So all that’s marketing, but it’s different.
It’s totally different.
Michael: It is very different. I would say in general, no, I’ve been playful with Instagram accounts that were supposed to be community oriented that I wanted to launch and build stuff off of, but it’s completely different than the written word or, you know, really building a website that is You know, in this kind of domain, I think anyone could do it.
I think some people are probably better at others, but then others. But I do think I come back to the idea of like experiences, what you get after you eat it, like just fricking start, we all want perfection or some of us I think it’s about like, I still, you know, I just launched one 800 fly fish, which is a newsletter for fly fishing and my goal is to launch an outdoor media company.
Use that as a platform to then launch a products business. Only once I understand what the core problems are and if this product resonates with them. Okay, so part of me was like, you know, I proved I could grow this local newsletter, you know, the tactics are relatively the same, but also radically different.
I sat there with, again, I send a weekly newsletter out. I haven’t missed a week in 56 weeks or something. I sat there looking at this template like, all right, I’ll come back to it another day because like there’s still that fear. It’s still very personal. You’re still sharing something that reflects you and Look, no one likes getting the door slammed on their face but like it is part of the journey and failure gets you one step closer to success and all that stuff, but it’s still like Primitively you’re like i’m not ready to hit send tomorrow tomorrow and you know I still experience that and I think the best thing in the world is just that Smash and send, closing your laptop, walking away, and then trying not to look at your phone in the metrics or whatever it is, the results, for, give yourself some time.
Sometimes we can’t do that. Sometimes you’re like, ah, let me just check. It’s been two minutes. Seven opens. Nice. You know, no one subscribes. But I think, There’s something very freeing in just creating something and putting it out in the world and seeing what resonates and look it might fall Flat on its face good.
You learned something now if you have the the the wherewithal the endurance the The you know, just the the passion and persistence get back up. Try again switch it up. Hey, I heard you I I understand you guys didn’t like this. I’m changing up the tactics. Let me know what you think below Wow, most people really like this.
Okay, i’m starting to fine tune the approach here and so Just get out there. You don’t need to have experience building this type of stuff. There’s enough content online, like what you’re creating. There’s enough tools out there that are low code, literally no code, and you can get going in an afternoon.
Do not expect to go to 10, 000 subscribers on day one. Like that’s, that’s craziness. It’s gonna take time. Because you’re building trust. You’re building a voice that resonates with people. And I think the amazing thing is once you keep hitting send, consistently people build trust with you. Opportunities, you know, open up.
The universe smacks you on the ass and goes, hell yeah. Like, things happen. And I think that’s the most amazing thing. Like, I have no idea where Catskill Crew will take me. No idea where 1 800 fly fly fishing will take me. Or the newsletter club. But just consistently show up, add value for other people, have fun with it.
If it’s not fun for you, you’re in trouble. Uh, you won’t, you won’t stay the course. Life’s too short not to have fun.
Doug: So we got to start wrapping up. I know you have a hard stop, so you’ve shared so much. I’m curious if you’ve had any missteps, any mistakes along the way, cause it sounds like everything’s kind of working out really well and good growth.
Excellent monetization numbers. What are some mistakes you made along the way?
Michael: Specifically in the world of newsletters, I would say some mistakes I’ve made have been not to put money on growth. You know, I, I reached this point where I was like, ah, you know what? I’m getting a hundred subscribers, you know, every two weeks, or, you know, this month I grew 400 subscribers.
It’s yeah, there’s only so much upside I can charge for these businesses. I now advise everyone to take whatever you can, if it’s 5 a day, pump it into ads. If it’s 20, 50, get creative with it because that audience is how you are going to make money. And it’s not all about money, but look, this is a business and you need to be able to monetize it.
So you can monetize that audience through traditional and creative monetization. So the bigger the audience, the better, but also make sure you’re spending time. On that click through rate and creating content that people actually resonate with because if you’re not doing that It doesn’t matter how big your vanity metrics are.
It’s worth nothing So start your ads earlier. I would say connect with other people. I was building this alone not on twitter not sharing this with anyone for a very long time and I told a friend of mine that I did 10k in revenue and he’s like, gotta start a class. And I was like, not starting a course, dude, like absolutely not.
But I did decide to start building publicly with this. And then I just started, decided to launch the newsletter club, which is members only community of local newsletter builders. And that just lights me up. We’re all sharing tactics. We’re all compounding knowledge. We’re all trying new things. Someone in Israel tries out this tactic.
Then someone in Colorado is using that and going, holy crap, I just reduced my customer acquisition costs by, you know, three quarters. Now everyone’s doing. We are not competing with one another. So there’s some real beauty in, you know, building the future of, of, of local journalism. Together and, and this is not competition.
So start teaming up. It doesn’t matter if it’s just getting on Twitter, talking to other people who are building or joining the newsletter club, talk to other people, building whatever you’re building. I would say, don’t be afraid to start reaching out, uh, and, and, you know, reaching out to businesses, start building relationships.
A mistake I made was assuming I needed to hit a certain number of subscribers, 2, 500, 3, 000 to begin monetizing. No way go out there, take a local business. You like, give them a free ad, follow up with them and say, Hey, I just want to introduce myself. My name is Michael Kaufman. I run Catskill crew, the best local newsletter in the area.
We’re growing quickly. I want to give you a free ad spot because I’m just a big fan of your business. Here’s the data to show how significant, you know, the traction is, how much that resonated with our subscribers. If you’re ever interested in, you know, being an advertiser, we’d love to have a conversation.
When they come knocking on your door, which they will, negotiate on a non CPM basis. Be like, hey, would you guys be willing to do 200 bucks? No? How about 150? Great. Sign that deal. Take that money. Dump it into further growth. And guess what? Their competitor is now going to see the ad. Because they’re going to start promoting it and then they’re going to knock on your door and the snowball is going to start ripping So get out there.
Don’t be afraid of perfection Start marketing this thing Get off, go connect with other people. Don’t be afraid of failure. Easier said than done, but you are not your business. You know, look forward to failure.
Doug: Do you go to like in person events? I know, you know, these, these events happen all the time.
If you go look, you know, there’s entrepreneurs in your community meeting to have coffee a couple of times a week. So do you, have you gotten out there shaking hands and all that kind of stuff?
Michael: I think naturally I’m just out there, not necessarily attending the events. I used to do that in the city, in New York City and in Boston when I was doing more tech startups.
You know, now this is very much like mayor vibes. Just show up, wear your hat that says Catskill Crew. People are going to come up to you. Hey, subscribe to the newsletter. I love it. Awesome. What do you love? What do you hate? Get feedback. I think one of the best things I’ve done is not attend the events.
I put on the events now and I get paid to do that, which is nice. So, you know, the events I put on with Catskill Crew, I’ve done everything from happy hours to booze cruises, to holiday parties, to barbecues, to foraging walks. Those businesses pay me to promote their, their, their, their business. All of them have had you know, revenue breaking days.
Thanks. Which is fantastic. And I can lean into that, but I’m meeting the businesses, the business owners, other business owners, community members, subscribers, that type of thing. I would do that without even getting paid. I think it’s really incredible to kind of position yourself as, I don’t want to say a linchpin, but deeply rooted in your own community.
And through that, you know, again, my goal here is to build a holding company specifically based in the Catskills. Okay. I know so many local business owners when the time is right, you know, knock on their door. Hey, I would love to buy you out. I’d love to own a little piece of this business. This is why you want me on your board.
This is why you want me involved. You know, I’m a partner in a fly fishing business. I’m trying to secure a commercial real estate space, uh, commercial space right down the road here. It’s, it’s really, Amazing to be a part of a community in a world where we’re so connected yet so far apart, man, it’s, it’s good for your body and your brain to know who your neighbors are.
Doug: And that’s so insightful about being the hub, like the organizer of stuff because people are bad at it. They don’t like organizing things. So even if you pull together sort of a small event, like you’re the person putting it on. Everyone knows who you are. You could even be kind of behind the scenes, but they still know who you are.
Very cool. All right.
Michael: Yeah. You don’t have to be an introvert either. Like just get out there, sit at the table with your hat on, let people come to you. Just do it. It’s, it’s worth it.
Doug: So as we’re wrapping up here I think I have like two to three more questions. Number one, a lot of the interviews that I’ve done around local newsletters, they are the first newsletter in their community, but I feel like it’s okay if there’s competition because you have your own personal perspective and if you’re writing it yourself, do you have any thoughts on competition or what, if there’s already a couple of newsletters in your community?
Michael: Yeah, I think like inevitably, whether you’re first or third, you know, there is going to be competition in some, in some standpoint, like you have publications who are already out there who might have a newsletter as well, who are, you know, print, um, work together. You know, I know that’s probably harder said than done to some degree to knock on someone’s door who has 10, 000 subscribers and be like, Hey, I just want to introduce myself.
I’m starting a local newsletter as well. But, you know, and be honest, just be like, look, I’m a huge fan of what you’ve built. I’ve gotten a ton of value. I’m looking to build a local newsletter. This is my angle. Don’t go direct. It’s not necessary. You know, again, kind of find the gaps in the market. It might not be, you know, it might not even be the biggest audience is the most monetizable, you know, it might be parents with kids.
So often I get emails from folks saying, you know, can you put more events in for, you know, parents would get, uh, events in with, for parents with kids. Yeah. Yeah, but I don’t really have enough space and I don’t have kids. I got, you know, 70 pound dog right here. So I do think like find what speaks to you, find what excites you and lean into that.
It could be the art and culture. It could be the music scene. It could be the outdoor scene. It could be experiences. It could be for the parents. It could be for the young folks going to nightclubs. There’s nothing wrong with niche, , niche down you know, niche all the way down, baby.
Doug: Perfect. All right. The newsletter club is that that’s what it’s called. Tell me a little bit more about it. Who’s it for and does it, does it cost anything? Do people just join up? What’s the story?
Michael: Yeah. So it started as a, you know. a place to bring serious builders who are creating local newsletters and In order to be serious, you need to have some skin in the game So it started at a hundred dollars for the first, you know, 20 members sold out really quickly now we’re at 53 54 members It’s 300.
That’s flat rate for life. I think there’s ways to monetize that more in the future. That is not my goal right now. Right now it’s to support local journalism to support newsletter creators, for all of us to share and learn together. I am not the person pulling all the strings, sharing all the knowledge.
There are brilliant people. We all have different strengths. We all have different weaknesses. We’re all learning together. And I believe fundamentally, if we work together, we’re going to go further together. You know, I’m starting to explore different micro niche kind of SAS tools to ease my pain. And just as a result, we’re all usually experiencing the same pain specifically around growth and monetization.
So yeah, right now it costs 300 to join for life. You do not have to be. Building a newsletter. But you, you sure should start soon. And there’s folks who have 20, 000 plus subscribers and some who are launching their first newsletter today. And you know, we’re all kind of hopping on calls every Wednesday.
We have masterclasses on Friday where we deep dive topics from monetization to growth strategies, to technology stacks we could use. It’s a, it’s an awesome place. Couldn’t, I couldn’t have gotten to where I am without the help I’ve gotten there as well.
Doug: That’s cool. So it’s like community led sessions and stuff.
So someone like really learned a tool and they’re like, Hey, I want to share this, that kind of thing.
Michael: We’re deep diving Apollo on Friday. We did meta ad breakdowns the other day we did, you know, how to structure and charge for events. And we’ll continue to do more. It’s possible that, you know, a lot of other folks have other newsletters as well, like myself that aren’t local newsletters.
So these strategies do work elsewhere, but, you know, being able to be super fine tuned and focused allows us to kind of like, Again, compound that knowledge and experience at a far more rapid pace.
Doug: If people are interested, where do they go to check it out?
Michael: Uh, you can check me out on Twitter. Mikey Pesto long name behind long story behind that name or the newsletter dot club.
Doug: All right, cool. Well, we’ll link up to that and people could check out Catskill crew. Is, is there a website at all with it? Or is it just like the landing page to sign up for the newsletter?
Michael: Just the landing page. I think that’s probably a whole different conversation, but you know, if you do have the website.
Make sure it doesn’t cannibalize the value of the newsletter and vice versa. So think ahead about how those two dance tango.
Doug: Got it. All right, Michael, this has been amazing. I’m going to link up so people can find all your stuff really easily. And it was great to meet you. Great to talk to you today.
Michael: Thanks for having me. Hope people learned something.