Building a 6-Figure Local Newsletter

In this conversation, Michael Kauffman, founder of Catskill Crew, shares insights on building a successful local newsletter, focusing on community engagement, monetization strategies, and the importance of authenticity in content creation.

He discusses the growth of his newsletter, the role of polling and feedback in shaping content and product, and the various revenue streams he has developed, including events and partnerships with local businesses.

Kauffman emphasizes the significance of building a trusted brand and the potential for local newsletters to fill gaps left by traditional media.

00:00 Introduction to Michael Kauffman and Catskill Crew

03:05 The Media Landscape in the Catskills

09:04 Growth Strategies and Content Creation

15:05 Targeting the Right Audience

21:18 Building Trust and Relationships with Advertisers

29:54 Building Community Through Events

36:39 Brand Development and Merchandising

42:18 Exploring Real Estate Opportunities

52:07 The Value of Local Newsletters and Community Engagement

58:16 The Future of Catskill Crew and Community Growth

Links

Visit Catskill Crew

Follow Michael on X (@MikeyPesto)

Start your own local newsletter on Beehiiv

Subscribe to the Monetize Media newsletter

Follow Kyle on X (@KyleScottL)

Kyle's brands

AccessGMT.com

WalkingTheBoards.com

Tip.News

OnPattison.com

Episode Transcript

(00:00):
All right, welcome back toMonetize Media. I'm Kyle Scott. On
this episode I talk to MichaelKaufman, founder, owner and operator
of Catskill Crew, a localnewsletter in the Catskills region
of New York. We get into howhe grew his newsletter, how he creates
his content, but mostimportantly we talk about the monetization

(00:20):
and business aspects of it.How he is forming direct relationships
with local advertisers, hisevents business, how he himself wants
to launch a business on thebacks of building a trusted brand
in the region. There is justsuper fascinating stuff in this show,
both for people who arecreating local newsletters or newsletters

(00:42):
in general as a mediabusiness, but also for business owners,
particularly small and mediumsized local business owners, and
how you can use a contentbased newsletter once a week to become
the most trusted brand in yourarea. Super fascinating conversation.
I learned a lot. So here's myconversation with Michael Kaufman.

(01:08):
All right, wanna welcome onMichael Kaufman, Catskill Crew. Michael,
welcome to the show. Pumped tobe here. Thanks. Thanks for joining.
So people heard a little bitthere in the intro, but why don't
you quick do like a 30 to 90second overview of what you do? Yeah,
you know, I've been buildingstartup companies for about 14 years

(01:30):
now. Started in the beverageindustry, found my way to digital
health, spent a long timefundraising, got a little, got a
little burnt out and decidedto start a new venture. Something
that was playful, fun,community oriented. I launched a
local newsletter calledCatskill Crew about a year ago and
just hit 11,000 subscribers.You know, I really see it as a local

(01:53):
brand more than a newsletterand an opportunity to build a holding
company. In addition to that,I run the Newsletter Club which is
a members only community oflocal newsletter creators. There's
over 60 of us who are startingto cover the entire world. And you
know, my vision for that is toreally kind of be on the forefront
of what local media andjournalism looks like. And then finally,

(02:13):
just most Recently, I'velaunched 1-800-Fly Fish, which is
an outdoor media company andkind of the same model of like how
do I leverage a newsletter tobuild a community to then be a Trojan
horse for a products company?Smart. Smart. Yeah. And full disclosure,
I'm a member of the communityand it's awesome in the couple weeks
I've been a member. How longhave you been doing it? How long

(02:33):
has it been going on? Istarted it while I was on a road
trip out west in August and Iwas firing off invites end of August
while going on the back roadsof of New Mexico and it quickly grew
closed. 20 members. And I waslike, wow, this is. This is really
incredible. There's a lot ofpositive energy here. Like, everyone's

(02:53):
helping everyone. Now it's 64members. And, you know, there's a
nice, healthy wait list. SoI'm slowly bringing people in. I
think with where the magic is,as you're probably coming to see
now, is there's people who arejust getting started. Some folks
have been in the game for 8,10 years, other ones who have exited,
and now we're kind ofreexamining what this space looks

(03:15):
like. Everyone's learning fromeveryone. We're compounding knowledge,
and it's just exciting. Itreally is fun. Agreed. All right,
so why don't you talk a littlebit about specifically what Catskill
crew? You know what, beforeyou do that, dig in a little bit
more. What made you want toget in to this space? The local newsletter
game. You touched on yourbackground, but maybe just sort of

(03:37):
tie together the thread ofwhere you were, how you got to here,
and why you wanted to kind ofbe in. I mean, media in general is
tough. Local media is harder.Yeah, it's a. It's. It's kind of
one of those things where Iwasn't sure what I was trying to
do next. You know, I think Iwas even talking to my therapist
at one point. He's like, youknow, are you really an entrepreneur?
After, you know, I just gottotally burnt out trying to capital

(03:58):
raise for this previousbusiness. I was like, I don't know.
You know, it's a. It's a. It'sa funny question. When you come into
these forks in the road inlife and you're like, what do I want
to do next? And I wanted tobuild something. I knew that it's
what I know how to do. It'swhat I've spent my whole life doing.
But I didn't want to getcaught in the capital raise trap
again. I wanted to have fullautonomy. I wanted to be able to
tap into all the skills that Ihave, which is community building,

(04:21):
which is branding, marketing,product development. And so, you
know, I kind of just startedexamining what my opportunities were.
And I saw just in theCatskills here, a few hours north
of New York City, it's reallyhard to find out what's going on.
I mean, exceptionallydifficult. I always talk about how
the algorithms have failed us.Businesses used to post for free,

(04:44):
get massive organic traffic.Then they had to pay for massive
traffic. Now they can't evenpay for what once they Once got for
free. There's no conduitbetween local business and community
anymore. And so I personallywas just struggling to find what
is there to do this weekend.It's such a vast region. There's
so much exciting stuff, butit's always like, I see the post

(05:05):
three days after it happened.So I started aggregating events that
were taking place in the areaand I called the Catskill Crew. My
mom subscribed and I was like,yeah, thanks, mom. But after about
a week, I had 500 subscribers.It's like, oh, organic. Yes, all
those were organic. I didn'tdo paid for quite a long time, which

(05:25):
is a lesson that I try toshare with everyone. Put money into
the Zuck machine as soon aspossible. It. You can't buy your
way to success orsponsorships, in my opinion, but
it's worth it. And so, yeah,pretty quickly got about 500, then
a thousand. You know, I put alot of effort into the organic and
the creative side of things tomake sure I was riding the coattails

(05:48):
of the established businessesand I just made them look really
good, you know, with theCatskill Crew branding, with their
branding and, you know, Istarted recognizing there's a massive
opportunity to do more.Started looking at other content
buckets. What else can Iintegrate? I'm a, I'm a history nerd.
So I started focusing on therich history of the Catskills. Oh,

(06:08):
my God. That really resonated.Running beehive polls. Do you guys
actually like this? What elsedo you want to see? And so it's,
it's, it's never solidified.You're always being playful with
it. And I think that playfulattitude with the Catskill Crew brand,
with the newsletter, it keepspeople sticking around. It's an authentic
voice. It's not stale orstagnant. It's ever changing. And

(06:33):
yeah, it's, it's, it'sincredible to see what it's grown
into. And 2025 is. It's goingto start off like, you know, it's
going to be pretty crazystart. Yeah. I love that idea of,
of kind of being able to playwith the format and the content.
I've always found in, youknow, I've been in content 15 years,
is that when you try to createa hard template, they can be good,

(06:56):
but they can then force you toeither do things that aren't really
that interesting or, you know,like have something interesting and
have nowhere to put it. Sohaving that flexibility is key. What
does the media look like? Yousaid it's hard to find stuff like,
what is the media situation inCatskills? Like, is there a local

(07:16):
newspaper? I'm not superfamiliar with the area, but, like,
what is. What is yourcompetition? Yeah, it's probably
similar across mostgeographies, right? Like, you have
Instagram, you have Facebookgroups, Instagram. It's a bunch of.
Look, it's, it's. Thealgorithm is add and it's kind of

(07:37):
perpetuating those behaviorswhere you're just scrolling. There's
deep. There's no deepengagement. So, you know, the timeline
screwed up. You're reaching avery small percentage of your overall
following. There's localnewspapers, but unfortunately they're
run like dinosaurs and bydinosaurs, I support them. I buy
every single paper. But I'veseen over the last seven years just

(08:00):
quality, you know, really,really kind of tank. And it's more
ads, the writing and thestories. It's just written for a
very different demographic.And so I wish them the best, but
unfortunately, I feel likethey're going to continue to capitulate,
which actually opens upopportunities for local newsletters
to fill that gap, become thebackbone. There's magazines and print

(08:23):
media out there, but, youknow, I'm an owner and a business
up here and the stack arrivesand, you know, by the time they bring
the next stack the followingmonth, one or two may have moved.
Most people aren't readingdeep diving into them either. The
content is. It might be great,but it's just so long form and no
one needs to read that much.They're to some degree, they're just

(08:46):
writing more to put more adsin. And, you know, so I think there,
there's nothing that offerssuch a direct conduit between community
and local business and reallyties in the history. And I think
first and foremost, this isreally about deepening the connection
with the region. That is mymission. It's about community. It's

(09:10):
about bringing peopletogether. And so it's not just about
getting the news. It's. I'mthrowing events all the time. That's
not about the money. Payspretty well. You know, I've probably
done $15,000 in events in thepast, you know, 60 days, priming
them for 20, 25. I got onethis weekend, one on Monday. But

(09:32):
it's about community. It'sabout the culture here, and the news
is part of it. Yeah. Now it'sinteresting. Sam Parr, obviously
from the Hustle, put out atweet the other day, kind of, I want
to say, dumping on like, kindof current newsletters that they're
maybe a little late to thegame. And he said, you know, he liked
to look at other companies andhistory to get his ideas to kind
of take from other categoriesand verticals and apply them to a

(09:55):
new business. But I actuallythink you could do that within newsletters.
If you look at the techbusiness, kind of news, straight
general news, even politics,maybe even newsletter space has played
out. But taking that playbook,which is what both you and I and
many others have done, andapplying that to local is. There's
so much opportunity there. AndI'm sure it sounds like you've experienced

(10:18):
this. What I've seen firsthandis people are like, this is awesome.
This is cool. Someone everyweek. This is highly engaging. It's
better than a magazine. It'sbetter than a newspaper. I can kind
of quickly.
It's the same playbook thoseguys were.
Running with the Hustle orwith Morning Brew, but applying it
to a local region, and peopleare almost, like, stunned that something

(10:38):
like this exists. They'relike, where has this been my whole
life? Have you had. It soundslike you've probably had that same
experience with people upthere. Like, yeah, why would I not
want this? It's the greatestthing in the world when I throw these
events and people come up tome and it's not just like, man, I've
discovered so many amazingplaces, or I didn't know the history
of, you know, bluestonequarries in the Catskills or bark
tanning leather. But whatreally kind of gets me going is,

(11:01):
like, I've made so manyfriends through Catskill Crew, and
I'm just like, oh, like, thatwarms my heart. And that's what this
is all about and everythingelse. Like, of course I need to make
money off of this. But at theend of the day, your defensive moat
is, are you adding value, notjust news, but value to people's
life? Are you being theconnective tissue to bring people

(11:23):
together to connect with theirneighbors, their friends, their frenemies,
whatever? And I do agree that,like, I think a lot of people have
been using newsletters in apretty generalized way. And I think
there's so many ways we couldtake this format. And through creativity,
you can build something somuch bigger. I always say, like,

(11:45):
my newsletters are Trojanhorses for a much bigger business
plan, a much bigger operationI have. And you don't need to know
exactly what's over thehorizon, but you need to be posturing
it, structuring it, unitingthat community, engaging that community
in a way that builds the Trustand authenticity. So when you go
to execute that plan on a. Ona bigger stage, you know, it's primed

(12:07):
and ready. I mean, you can'tdo surveys and polls and get the
insights you want throughprint media or traditional media.
That is such a superpower. Apoll and a survey is insane. I don't
build anything without runninga survey. Do you run the results
of the survey or poll? Becausewe've actually used that for content

(12:28):
in some cases. About, like, apopular issue in town. Yeah. So 1-800-Fly-Fish
now, it's. It's being veryplayful and fun, and I'm sharing
the results every week. Andthe same with Catskill Crew. You
know, I'm like, hey, do youguys want to, you know. A Monopoly
board completely branded forthe Catskills with reservoirs, rivers,
towns, fire towers? Yeah. Allright, well, 97% of you voted for

(12:51):
this, so I'm going to go burymyself in Alibaba. Working with Chinese
manufacturers for the next 60days to make this a reality for you.
And I think that type ofautonomy, I say it's a newsletter
for the people, by the people.And I mean, it's. If someone doesn't,
if the community votes no forsomething which hasn't happened yet,

(13:13):
I'm fine with just bringingout back, killing it, and never talking
about it again. I love theMonopoly idea. I would steal that
if we weren't like, two milesnext to Atlantic City, where Monopoly
is actually based on. It's agreat idea, and it's going to be
fun. It's designed to beevergreen. It's a journey. It's a
process. I didn't know what Iwas getting into, but I just got

(13:34):
a video of the. The latestproduction run. They ship out on
the 18th, so they should behere early January.
Okay.
So I want. I want to reallydig in on the business side before
we get there. So I just wantto go over kind of the growth in
the content. So you got alittle bit of organic traction. Early
on, you said about 500 people.At what point did you kind of begin

(13:54):
investing in Facebook ads? Isthat the primary form of growth?
And then after that, you know,you kind of mentioned you're a marketing
and business guy, and what Ididn't hear was like, journalist
or content, which, by the way,I found some of the best media businesses
have started by people whoweren't traditionally journalists.
So I think that's actually apositive. But talk about for you,

(14:18):
is there a challenge increating the content? You've focused
mostly on events. Do you do asmuch news or is it more events? So
talk about the growth and thenhow you position the content and.
And then we'll kind of getinto the business side. Yeah, growth.
You kind of have two buckets,right? You have organic or you have
paid. It's not rocket scienceorganic. You know, it's Reddit groups,
it's Facebook groups, it'sInstagram. It's making businesses

(14:41):
look good, riding thecoattails of them. So they're sharing
with their audience andyou're. It's basically a vampire
attack, but not in a negativeway. Let me dig. I want to double
click on a couple of those.The Reddit piece, is it local subreddits?
Because I've looked into this.I'm like, man, sometimes it's tough
because you can't always withlocal newsletter, tap into the scale

(15:02):
of the Internet with somethingthat's local. So talk about the Reddit
and then talk about riding thebusiness coattails. Because sometimes
you want to leverage abusiness, but also you eventually
want them to pay you forsponsorship. So how do you sort of
do that? Like on off dance ofhey, I'll promote you and we'll have
a relationship. But certain,you know, at some point I might want
you to pay for that. Yeah. SoReddit, you know, you go in, you

(15:26):
find subreddits in your areaand you deliver value. Right. So
I post the A list of some ofthe events for the week. Hey, if
you guys want the entire list,sign up here. It's totally free,
unsubscribe anytime. And ifyou want me to get any spots on here
that aren't covered, let meknow. Some mods might boot you out.

(15:46):
Okay. There's nothing youcould do about that. A little bit
of a headache and a pain inthe ass. Spin up your own subreddit.
Catskill Events or CatskillCrew, simple as that. And start bringing
people over. Now you own thatdomain. The same tactic can be used
in Facebook groups. So that'sreally kind of the way to play the
Reddit game. You kind of gottwo approaches. Tap into existing

(16:10):
markets. If you get pushedout, spin up your own. You will be
able to find people and youcan even advertise that quite effectively
on Reddit. It's a fairlysimple advertising platform for writing
the final. Get a lot of subsfrom Reddit. Yeah, and I. From the
ads. From the ads. I don't dotoo many ads. I've done them with
1-800-Fly-Fish because it'svery easy to target a subreddit.

(16:34):
But I found my acquisitioncost was so low on Facebook and I'm
already spending so much timethere that I'm just going to keep
my efforts there until thatCAC gets a little bit higher. And
then I'll shift back over intoReddit and explore kind of this untapped
vein. How low are you going onFacebook? How low can we go? How
low can you go? I would say mylowest was about 38 cents and now

(16:59):
I'm hovering around 42 cents.But every market is different, every
type of copy and media isdifferent. And you have to be playful,
you have to kind of, you know,move. You have to do a little bit
of kung fu. Right. You got tobend with the algorithm and the black
box of, of the meta adplatform and there's some ads you'll
put out there and you'll belike, this thing's gonna crush and

(17:21):
it gets no exposure. You'relike, that doesn't make sense. And
you just kind of have to bevery a B testing and you know, have
a backlog and tinker. It mightbe going from static to video. It
might be totally differentcopy or subtle things. No one really
knows how that that thingworks, but when you find something

(17:41):
that is running, pump somedollars onto it. So the Catskills.
So I imagine there's a lot ofpeople that have second homes there.
Yeah. So this is a challengeI've run into is, you know, you could
zip, zip code target onFacebook, but sometimes you might
want to reach people whoaren't there all the time. So I've,

(18:02):
you know, kind of targetedpeople who are members of groups
or have liked pages related tothe town. What sort of targeting
do you use? Because it's kindof maybe different than someone's
like true local town whereit's like all year round residents.
Yeah. So I'm hitting all thecounties so who are up here. So the
weekenders who are coming up,they'll see it over the weekend,
whether you know, scrollingInstagram or Facebook. But at the
same time I'm targeting kindof the general vacation, the vacationers

(18:26):
location. So that's Longisland, that's New York City, that's
Jersey, that's westernConnecticut. And you know, it's working
right now. And at some pointwhen it starts kind of petering out,
I'll spin up a new campaign,duplicate, you know, make sure that
the audience isn't beingtargeted that I already have and
you know, start playing aroundagain. But in terms of audience itself,

(18:48):
you know, I say 22 plus. Idon't really add too many demographic
requirements there. I letZuckerberg figure out who the right
target is and let him do histhing. You pretty much just roll
22 plus in these areas and,you know, Facebook will figure out
who spends their time in theCatskills. Interesting. In addition
to adding kind of my excludelist, which is downloading my Beehive

(19:11):
subscribers, kind of scrubbingthe list of the inactives, focusing
on the actives, uploading thatwith just the emails and saying,
don't target these people, youcould also do a lookalike and say,
target people like this. Sothere's a bunch of tactics you could
use. Facebook is one of themost complicated systems to really
do right, you could do it, youcould do it. But to really do it

(19:33):
right, you got to be effectivewith it. The interface, too. The
interface gets me for acompany that's like, consumer, you
know, they've probably thoughtabout every pixel on the consumer
facing end to optimize forusability and engagement. And it's
like the back end makes youwant to throw your laptop through
the window. I've done it. I'vedone it. I've drawn it a few times.

(19:54):
What do you view as kind ofyour, like, your tam, like, what's
your address? How many people,theoretically, if you got every single
person subscribed to yournewsletter, could you get? Yeah,
it's funny. And I, I, I won'tBS it, I don't know. And I, I'm not
too worried about thatoverall, because I'm, I really, I've
struggled in the past around,like, you know, before I started

(20:17):
deploying capital into ads, itwas really about like, well, what
do I need here? Is it 10,000true fans, you know, or a thousand
true fans? Sorry, 10,000 wouldbe amazing. It is a quality over
quantity. I am very muchfocused on subscriber ltv. It's,
it's not so much about what ismy open rate, Everything like that.

(20:39):
Like, are people willing tospend money on my products, coming
to my events? That's the mostimportant thing. But this is a massive
region. Three hours east towest, you know, two and a half hours
north to south. That's justthe locals and weekenders. Then you
have New York City folks. Sothere's an opportunity to niche down
into the Catskill Crew brandand create Catskill Crew experiences.

(21:01):
Bringing people up here,unlocking a whole new opportunity
to build a relationshipbetween them and my brand, but also
to monetize. I'm not a big fanof traditional monetization. Overall,
ads and sponsors, I'm lookingat it from a much larger creative
standpoint. Yeah. All right.Yeah, so let's get into that. So
you use Facebook a lot forgrowth. Cost is, you know, under

(21:23):
$0.50 per subscriber, whichis, which is excellent by any metric.
And I think you're probablygoing to explain why your LTV compared
to CAC is excellent. Contentsounds like mostly events, a little
bit of news, a little bit ofhistory. Have that, right? Yeah,
yeah. And I'm always playingaround like I feature charities and
everything like that. And youasked earlier, like, what's my experience

(21:44):
in journalism? I was a collegeintern working at the Boston Globe
doing classifieds. I wouldn'tcall that a journalistic experience,
but I've been telling storiesin marketing for 14 years. How do
you get someone to care abouta brand? How do you get them to understand
something super complicated?And actually, like, I was an intern
for Jay Walker, who was thefounder of Priceline, prolific inventor,

(22:06):
300 plus patents. And he, thefirst day at the office, he introduced
me to his chief story officerand I was like, what? It's a great
title. I was just like, I wasperplexed. I was like, what do you
mean? And we had this longdiscussion around it doesn't matter
how good your team is, howgood your product is, how novel anything

(22:27):
is. If you can't tell thestory and get someone to care, then
it doesn't really make adifference. And so I think part of
that is how I tell thesestories and how I write. It's just,
it's authentically me. Andevery time I write, I'm writing as
if I'm talking to you. And Ikeep it casual, I keep it light.
And so, you know, I thinkthat's, that's very important to

(22:48):
everyone out there. Like, beauthentically yourself, because that's
what people crave. I thinkthat's so important. I think a lot
of people, especially theselast couple of years, have really
sort of tuned out. Maybe theclassic journalism style. You can
still deliver really goodinformation in a professional way.

(23:09):
But everything was. Journalismstyles were rooted in AP style, which
is inverse pyramid. Andthere's a literal reason behind that,
which was in newspapers, theywould have to cut off the least important
part. So you'd have to writein a way that they could just chop
any of the bottom paragraphsand nobody would notice. And it's

(23:30):
not the most engaging format.And to your point about chief story
Officer, humans are narrativedriven people. Everyone likes a story.
And even consuming complexinformation usually Requires putting
it in a narrative so thatpeople can kind of grasp it. So I
love. I love what they weredoing there. I love that title, by
the way. Yeah. And youmentioned, like, which are the content

(23:51):
buckets? Like, yes, it isevents first and foremost for me.
However, I do try to, like,again, kind of highlight the past
and bring it to the future ofthis area. And it's so rich in history.
And so that's everything fromfly fishing to the wildlife to, you
know, the resources fromhemlock and tanning and everything

(24:12):
in this area. And so, like,I'll play with these secondary buckets
and these tertiary buckets.And I think that's also what keeps
it interesting of, like, hey,I don't know what's going to be in
here next time. However, thereis opportunities to niche down, spin
Out Land and Lodge, which isanother publication I'm looking at
launching focused on realestate. There's opportunities to

(24:33):
go to experiences. And so alot of people say, should I go wider?
Should I go wider? Nah, godeeper, in my opinion. But, you know,
everyone has their own kind ofstrategy and approach. Not. No one
is better than the other. Allright, so let's talk about the monetization,
then maybe talk about today.Start with ads. You know, ads is
the obvious spot. So talkabout ads. Talk about different parts

(24:58):
of the pie that you monetizewith and then where you'd like to
go. And focus specifically fornow on Catskill Crew, like, how you
build that brand and where youare today, where it could be in five
or 10 years. And then we'llkind of dig into each of these. I
might kind of pop in along theway and ask you to, like, go deeper
on something. Yeah, please do.I might start going on tangents.

(25:20):
You know, I spend a lot oftime answering questions from folks
of like, hey, I just put a tonof money into my newsletter. I got
5,000 subscribers, but I can'tget a single advertiser. Well, it
takes time. You know, youcan't just pump money into a local
brand and expect there to betrust. You got to kind of be out
there. And the fastest way tobuild trust, in my opinion, is to

(25:41):
give stuff away for free. Showvalue, show goodwill. And so from
day one, I was giving out adspots to my friends and their businesses.
And it was really kind oftwofold. It was to. It was threefold.
One, optically, it made mynewsletter look bigger than it was.
Two, it was. I was able tobuild relationships from a business

(26:03):
standpoint with my friends,businesses showing them metrics showing
them value. And then three, itwas, they were promoting it. Their
competition would see andtheir competition would reach out
to me and be like, hey, Iwould love to advertise. I'm like,
I'm working with the Pinesright now. I can't really. When their
campaign's over, like, I wouldlove to talk to you. I love your
business. Like, here's someinformation. And then I would just

(26:25):
wait it out two weeks and belike, all right, that campaign's
done. Let's get to work. So Ithink right out the gate, give away
free inventory. You know,you're. It's not necessarily. You're
not monetizing in any way, soyou might as well put it in there.
Find partners you want to workwith, start showing them metrics,
start finding, finding. Iwould say challenge yourself to find

(26:45):
advertisers that are value addfor your subscribers as well. So
that's like first andforemost, there's a bunch of different
ways and placements. You havebanner ads for me. I do a lot of
featured events, so I havethis long list of happenings. But
to guarantee your event is inthere, because there's about 200,
300 each week you pay, andthat could be 250 to $500. If it's

(27:07):
a small business. I like them,I know them. Or they've come through
a recommendation, like, I'llcut you a deal, no problem. I'm not
here to maximize my profitfrom each business. If I know their
margins are tight, I'll giveit to them on the house. Like, I
will give favors all day long.And it's not even about like, oh,
they're going to come back tome and pay me on this next round.

(27:27):
It's about building thoserelationships. You're in a small
community and they will spreadgood word for you and are actively
like a organic lead gen onyour behalf. So by the way, dump
into that for a sec. Supersmart. You know, it sounds like you
don't have a rate card, right?And I think so many people in advertising

(27:49):
will always ask, like, well,what's your rate card? Or, you know,
what's the cpm? And I thinkI've seen you say this and I think
I agree with this, especiallywith the local newsletter, you don't
want to be bothered with CPMs.That's for big ad buys where people
need to get a certain numberof eyeballs. In this, it's sponsorship.
How much is worth it for thebusiness to pay you? Because the
CPMs will never really workwhen you have 10 or 20,000 people,

(28:10):
which is kind of the range formost of these. Even a good CPM is
not maybe going to pay enoughfor the amount of value you can generate.
When you can reach like 60% ofa local population with a single
email and half of those peoplewill open it, there is a premium
to pay for that. Even if it'sonly 2, $300, that might still be

(28:32):
3x what a good CPM would be.Absolutely. I mean, if I had one
bumper sticker to put on mycar, it'd be throw your CPMs out
the window. I mean, truly, Ithink it's like, I don't have a rate
card. I'm first to admit thatevery business I go to, I send them
a partnership kit, which justexplains kind of like high level
why, what is my competitiveadvantage? Look, put yourself in

(28:53):
their shoes. They've wasted aton of money advertising, marketing,
with probably very little toshow for it. So you got to kind of
like get on their level,address that pain point, and say,
look, no one else is likeCatskill crew. We are the most direct
way to reach the customers.You want 10,000, 11,000 locals, weekenders
and vacationers. Not a blackbox like print media or an algorithm

(29:14):
like Facebook. This is directto inbox. We have the data to back
the efficacy and mostimportantly, you have the trust and
the authenticity of workingwith my brand. And I mean that in,
like, a really honest way.I've spent a long time saying no
to brands and nurturing thiscommunity. I'm not going to take
money from any business. Soworking with me is really about validation

(29:37):
as a core partner. I actually,like, approve this message. So in
terms of the CPMs, yeah, Idon't use them. I send the partnership
kit and then I set up a call.If they don't follow up with that,
like, they're just like, well,what are the rates? I'm like, can't
do that. I need to understandwho you are, what your goals are.
Like, are you a big businessor a small business? Because I don't

(30:00):
want to like, throw out, hey,it's $700 a week. And they're like,
whoa, we can only do 200. I'llprobably come right back and be like,
you know, there's always thissweet spot you find. I'll go as low
as I can go. But at somepoint, you have to, like, honor what
you've created and people willtry to pull fast ones on you. So
it's kind of like, how do Isupport local. But at the Same time,
you know, make sure that I'mvaluing what I've built and what

(30:23):
I've invested in and what Iknow this can deliver for the business.
So an example is I've donecollaborative events. And, you know,
I did the first one, and, youknow, it was, hey, do you guys want
happy hour together? Like thecatskill crew community? 95% in favor.
Okay, went to a business.Let's do tickets, $20, get a free

(30:47):
drink, 20% off rooms. Theysold out. I think they moved 12 rooms
on a Tuesday night and did$7,000 over the bar. It was their
biggest night ever. And I waslike, holy shit. Like, I probably
won't be able to do thatagain. Did another event, another
event, another event. Everysingle one has been a record breaker.
I never guarantee this, but Iknow these. The chances of a record

(31:08):
breaker are tremendous, letalone just the marketing exposure
of being on Catskill Crew. Thefeet, the foot traffic through the
door. And so are people payingyou, or is the. Is the venue paying
you? Or both? There's a bunchof different ways to cut it up. I
would say the majority of themare the venue pays me. I try to really

(31:30):
simplify it, and I don'tincrease those rates too much. On
average, it's 1500 dollars to2000. But I have some in the pipeline
that are $7000 events. And thereason why I don't charge too much.
So it's like. And I reallypromote it for three weeks leading
up to it. I design posters. Ireally make it feel special because

(31:53):
it's an opportunity, yes, toride the coattails of these other
businesses that I'm workingwith, but to bring the community
together. And at the end ofthe day, that is the most important
thing that could possiblyhappen. It makes me more than just
a newsletter. It makes me, youknow, a best friend. And so, yeah,
I would say there's a bunch ofways to cut it up. You can charge
tickets. There's free eventsthat people attend, and the venue

(32:16):
pays me. It's a marketingeffort, but know your value. And
early on, you might not. Youmight be like, ah, I'm gonna throw
one of these events. Run itthrough your. Run it through your
audience. Let them vote onwhat they want. Do they want bingo
night? Do they want happyhour? Do they want a full foraging
experience out in the woods?Let them guide you and then support
that effort, because you arebasically just executing what they

(32:37):
want. And it kind of removes alot of pressure off the operator
to do that. To be like, youknow, What? Yes. Of course, we're
all nervous every time we hitsend, but, like, I'm doing what you
guys want, and, like, we'regonna have some fun with this and
be light with it. What. Whatwas your audience size when you had
that first event, which is asuccess? Cause I wanna maybe give

(32:59):
people who have a localizedaudience what sense, you know, what
level they need to be at wherethey can think about an event. And
quick aside, 14 years ago withmy sports website, I thought I had
a big website audience. A bigwebsite audience is a lot different
than even a small newsletteraudience. You need very large on
the website. Cause theengagement's not as high through
an event. At a bowling alleyin Center City, Philadelphia, three

(33:22):
people showed up. Two of themwere me and my girlfriend. And it
was like four months in. And Iwas like, all right, we're not ready
for events yet. Now, yearslater, we had hundreds of people
show up. But that will. Thatwill bruise. That will bruise as
well. That will leave somebruises. It has to. That hurts. I
know. And, you know, it'slike, I was probably sub. A thousand.

(33:44):
It was March last year. Maybea thousand subscribers. Maybe. Maybe
1500. Yeah, I think it was,like, early March. And I went to
a place called Urban Cowboy uphere, which is like a trendy Brooklynite
mountain bar, restaurant andhotel. And I was just like, talk
to the gym. I was like, hey,what do you think about doing a happy
hour here? And he's like,yeah, all right. I was like, you

(34:07):
guys definitely don't want topay me. No. No. Okay. So we decided
to do whatever. 40 tickets orsomething like that that we priced
at 20, 25 dollars. Wenegotiated what that got you. And,
you know, again, like, oncethat was set up, I kind of started
asking people, what do youwant to do? Okay, you want to do
a happy hour? Where do youwant to do it in this massive area?

(34:27):
You want to do Ulster County?Okay, here it is. 40 tickets. You
know, X amount of dollars. AndI think I moved one ticket on day
one. And I was like, shit, I'mall alone drinking martinis. Not
the worst thing in the world.And what I realized was, like, I
don't think I announced therewas 40 tickets. So, okay, number

(34:47):
one, scarcity value. Like, allright. So now I started dropping.
All right, there's 30 ticketsleft. Then on social media, 25 tickets.
20 tickets. And then I startedmaking it very friendly. Come hang
out with your friends,neighbors, and, you know, like, let's
have the best time ever in themountains. And I Would say it sold

(35:08):
out. And then I sold probablyan additional six tickets the night
of because there was no.Everyone could still roll in. But
yeah, you could do it at anysize, but make it. I mean that is
like 4% of your audienceshowed up to an event which is, you
know, getting a 4% clickthrough rate is tough. That is insane.
And the GM came over to me inthe middle of the night, the middle

(35:31):
of the party and he wassweating and he's like, we were understaffed
for this because then theystarted inviting friends in and then
it was like, screw it,everyone just comes in. Like, you
don't get free drinks oranything like that. But like the
bar opened up and the bar wasas deep it's ever been. And I think
the magic for me was like whenpeople said like, this is the best
party ever. And it wasn't overengineered, it was just, it wasn't

(35:54):
about like having this livemusic and designing everything. Right.
It was about community. Andthat's the most important thing.
That's awesome. That'sawesome. Okay, so your events are
a big part of the businessnow. 100%. You do them same type
of events? Happy hour typeevents? No, all different. So we've
done foraging walks andbrewery tastings. We've done, you

(36:15):
know, July 4th parties withoyster bars and martini making class.
This weekend we have a holidayparty which is, you know, a special
drinks menu, a live band.We're going to do a, a cooking experience
and fly fishing experience ata campground over the summer. Just
keep it interesting, keep itfun. What is the, what is your range

(36:37):
of demo? Right, so when, youknow, I imagine the first event you
had people show up and you'relike, what does my audience look
like? You know, man, woman,old, young, you know, do you have
sort of a sweet spot or dodifferent events kind of have different
mixes? It is everyone. That'swhat lights me up too. Like, you

(36:57):
know, we just did a boozecruise on the Hudson river on the
oldest passenger vessel outthere. And the oldest people were
probably about 75ish. Theyoungest were probably about 22.
You know, there were localswho've been living up there their
whole life. And there was, youknow, folks from New York City who
are, you know, very wealthywho just moved up here and, you know,
wanted to start meeting somepeople. And I think that's where

(37:19):
things, you know, really areinteresting and exciting for me is
the idea that my voice, mywriting style, how I operate this
business really resonates withthis massive audience. And I Don't.
That's so important to me, isto not kind of exclude anyone. That

(37:40):
is awesome. Okay, so you gotads, you got kind of these direct
sponsorships. You got theevents. You've kind of mentioned
using it to create a brand.You said you have business up there,
so maybe touch on that. Andthen how you plan on using Catskill
to create a brand. I knowwe've kind of talked about, you know,

(38:01):
even these service businessesin town could be really interesting.
Whether that's partnership. Dothat, and then we'll get into the
real estate piece. Because Ithink that's a separate branch off
of the same idea. Yeah. Cool.So I think, like, first and foremost,
you know, you've built abrand. If someone's willing to buy
a hat with your logo on it,you know, if you're running a newsletter

(38:21):
and someone's buying your hatwith a logo on it, you've built a
brand. Congrats. Good work.And that's a good rule of thumb.
I like that, Chief storyOfficer. Buy a hat with your brand.
Buy a hat with your logo, youbuild a brand. Two good takeaways,
you know, and so I started,like, really kind of like, hey, does
anyone want shirts? Yeah.Because I'm going to make one myself.

(38:43):
But if, like, other peoplewant one, cool. I'll make 50 of these.
You're polling along the wayfor all these ideas? Yeah. So smart.
Every single point. Doesanyone want hats? Okay, I'm gonna
get them custom made. You guyslike these? Should we. What colors
should we do? I had everyonevote on every single piece of this
journey because they feelinvested in the outcome and excited

(39:05):
about it. And I've done somethings in the past which have, in
my opinion, failed. I did apiece of art, and I've done some,
like, scratch off posterscalled the Triple Trout. Catskill
Triple Trout, which was reallywell designed. It didn't sell that
well. I did an elder buckprint, and I was kind of like, does
anyone want art? And it was apretty solid response rate, but it

(39:29):
didn't move that well. I stillmade a profit, but there's some things
that just move better thanothers. And, like, don't beat yourself
up. And it's also not aboutselling out instantly. Play the long
game. But, yeah, I was gonnasay, like, it's. It's to build the
brand, I think is the mostimportant thing. And again, I've.
I've thought of Catskill Crewas really the validator and distribution

(39:52):
vehicle for a holding company.So how do I. I'm a Partner in a fly
fishing shop up here. And youknow, I think like when you, when
you have this platform with10,000, 11,000 subscribers, there's
no more effective way. Iunderstand the value and I see the
value it's generated for localbusinesses. Like, man, there's only

(40:13):
so much upside, so muchsubscriber ltv, so much money I can
make off ads and sponsors.Like, the next best piece of that
is to own the advertisingspace and the business that's advertising
in there. Now what businessesdo you move forward with is the biggest
question. Well, that's whereyou let your audience guide you again
so you could start asking keyquestions. Man, I'm having a hard

(40:35):
time finding firewood. I livein the Catskills. It's cold as hell.
We have wood stoves going allwinter. Long cords and cords of wood
are coming in. We're choppingit. Finding a reliable individual
to bring you wood through thewinter, hard to do. And so you could
literally just ask questionslike, man, I'm having a hard time.
Anyone else having a hard timewith this thing? And you could be
playful with it. Oh, shit. Alot of people are having a hard time

(40:57):
with this. Okay, well let meput a, let me spin up a little lead
gen website that's welldesigned. Put an ad in there. I don't
even have to say I own it. Iactually have not done this yet,
but this is how I would runthe playbook and just, okay, Catskill
Firewood company. How manypeople are actually clicking into
it? How many are signing up?Shit. All right, there was 250 clicks

(41:20):
and 150 signups. All right,well, do you want to go acquire a
firewood business? Do you wantto invest in one or do you want to
start one? You have a lot ofopportunities there and obviously
that's firewood. There's housecleaning, there's all different services
businesses, there's softwarebusinesses. But when you own that
validation engine, thedistribution engine, it's just one

(41:41):
of the biggest monetizationavenues you can do. Yeah, I love
that and I love. There'sprobably two arguments that putting
your brand name on it. One isif you know it's good, eventually
you want to tie those thingstogether because your brand carries
value. But you can put up thatfirewall early on that if this doesn't
work or you don't go down thatroute or it just doesn't go well,

(42:03):
like you don't sour the mainbrand. And you could very easily
test. So smart. It's such, Ithink like a cheat Code if you have
an audience. We used to sell alot of apparel at my sports site
and within five minutes youknew if you had a good product and
we would poll people, buteventually you just have to make
it and put it for sale. And Iwould tell you like, if we didn't
get a couple of sales withinfive minutes.

(42:24):
Right.
It was like not a good shirt.And like the quicker you got one,
you get that instantvalidation. And then if it's not
a winner, you know, you buy 25of them and you don't print anymore.
And that's it. Interesting.So, okay, so when you think about
businesses, it's like, okay,how can I use the brand? Maybe spin
up a little bit of lead genand then think about partner, acquire

(42:46):
or launch. Are there any ofthose before you get to the real
estate piece? Are there any ofthose that you've kind of identified
early on and then, you know,maybe as a side question to that,
I imagine, you know, you'relargely a one man show on Catskill
Crew if you're not correct me.But at what point? And this has been
a challenge for me, you know,we're kind of running, you know,

(43:08):
almost a dozen of these localsites now. And there's a. We want
to build some of thesebusinesses on the backs, but like,
you could spread yourselfthin. And being in the firewood business,
for example, is a muchdifferent day than the media business.
And how do you kind of scaleyourself and then at what point do
you sort of hire. You need tohire people to run these businesses.
Yeah. So it's just me runningCatskill Crew and my puppy who's

(43:31):
sleeping down here snoring.Easy life. I have two VAs who helped
me with event identificationand aggregation, but I think you
nailed it. You only have somuch time in the day. So how do you
find your way to executing,let's say, hypothetical? We identify

(43:52):
that the firewood business isactually killer. We have a thousand
people who signed up as leadgen. They're willing to pay, they're
biting tooth and nail to bethe first customer and get cords
delivered. So, you know, thenyou have the question, well, look,
Kyle, it's going to take a tonof money for us to start this thing
to get the gear, to get theknowledge. I don't know how to do
it, you know, so like thatrules it out right there. And do

(44:14):
I want to do that all daylong? Probably not. Do you want to
do a house cleaning business,A roofing company? Probably not.
And so it kind of leaves theOption of do you acquire a business?
Well, if the prices are right.You know, we have an aging population
who wants out of theirbusiness. And you could probably
negotiate fantastic dealsright now. And the other side is,
you know, do you just want toinvest in, you know, a business where

(44:37):
you trust the operators?There's both pros and cons there.
If you trust the operators,great. You're only going to own a
percentage of it if youacquire the business. Well, now you
need to find operators who arereliable. And where I live, that's
a really hard task. And inmany places, people don't like to
work. So, you know, we kind ofhave to be very diligent through

(44:57):
that process. And, you know, Ibelieve in kind of moving fast, breaking
things, you know, that wholephilosophy and not chasing perfection.
But when it comes to thatservices side business, I am happy
to wait all day until thatopportunity arises where I'm like,
that's the one, because I willlean all in on it. So I practice

(45:18):
patience on that front. Yeah,find the signal, you know, kind of
wade your way through thenoise. All right, so you mentioned
real estate. What does thatmean for you? Kind of talk about
the idea as you think aboutreal estate? Because I think a lot
of local newsletter peoplehave kind of identified this as obviously
a high ticket item servicebusiness, inherently localized. What

(45:41):
does it mean for you? Yeah, Italk about this in the newsletter
club quite often. It'sactually my struggle to execute this
new publication concept. So Iwent out there identifying a potential
opportunity which could behighlighting real estate with my
own kind of authentic voiceand under the branding, the Catskill

(46:01):
Crew. And I kind of posed thequestion, hey, does anyone want a
weekly newsletter on realestate? And I was shocked that it
was like 89, 90 in favor. Andthe ones who were against it, most
of them were just like, you'redoing so much already. And I was
like, oh, that's, that'ssweet. Thanks, mom. Yeah, it was
like, there's more caffeine,it's all good. And so I designed

(46:22):
the whole brand land and lodgeI've talked to, which opens up the
opportunity for likehospitality plus real estate. So
kind of thinking biggerpicture. I, you know, negotiated
a couple deals with somerealtors where they wanted to get
involved. I kept it at 3,spread out across the region. However,
I've still yet to pull thetrigger, and that's pretty unlike

(46:45):
me. And I think I'm trying totrust my gut and my instincts here,
where the conversations withrealtors look, they're very much
just Like I need to close asale. I need a sale. I need a sale.
They are hunting. You know,it's not the authenticity I'm looking
for, the relationshipbuilding, it's look, they have a
job to do. I respect thatprocess. But the other part is the

(47:08):
idea that this is a newsletterfor everyone. When you start getting
into real estate, look, youhave folks who are on Zillow porn
scrolling but then you havethe other individuals who are like,
look, everything's sevenfigures now and there's a massive
drop off of quality andeverything like that in this area
as folks have moved up hereduring COVID and spiked prices. So

(47:30):
how do I do that in a waythat's not divisive and diluting
to my, to my subscriber base?I might honestly be overthinking
this like crazy. But I'mthinking about what I want and everything
is through the lens of what Iwould enjoy and I haven't found that
sweet spot now. Yeah, it's amassive opportunity nonetheless.

(47:50):
But I tried to do everythingdifferently as well. So kind of what's
my unique twist on the realestate market up here? Still haven't
figured that out yet. Andit'll come to me or it won't. I think
we're very. You and I may bevery similar in that regard. I always
like to like just be a littlebit different, especially with content.
Like how do you do it? Likeit's different than what's, what's
out there. We've. So I'veexplored this real estate thing and

(48:13):
it's. And we're in like kindof similar spaces at least with,
you know, our walking theboards at the shore, the Jersey Shore,
because it is a vacation.There's a lot of vacation. Home prices
have gone up since COVIDsignificantly and the audience is,
is, you know, in general, verygenerally speaking. And it sounds
like, you know, you're in asimilar boat, one of two buckets.
You have maybe the vacationeror the second homeowner. So you know,

(48:36):
different bucket. And thenmaybe you have, you know, at Jersey
Shore there's a lot of localswho, you know, aren't maybe in that
income bracket, but becausethe real estate's gone up, I mean
their homes might be worthsignificant, substantial life changing
amounts of money.
Right.
So they actually do have a. Alot of locals will complain about

(48:56):
the value of real estate goingup and people getting priced out,
but at the same time they havea large asset as a result. But I've
kind of struggled with thistoo. We've Toyed with this idea,
doing the same thing. Spinoffreal estate brand. So much pull through.
We've promoted it a few timesin our newsletter and the amount

(49:17):
of people who've opted in, wegot 2,000 opt inside. We've only
done. I haven't sent one outin eight months. One piece of content
that worked was looking at theMLS results. And you know, these
MLS results are very messy.And the Redfin's and realtor.com
of the world do a really nicejob of real estate stats and data
and commentary on a nationallevel, but it really breaks down

(49:40):
on the local level. It's justreally not good. It doesn't understand
the local market. So we sortof took some of that data, data,
wrapped a nice contentpackage, put our spin on it localized.
It talked to developers,talked to Realtors, and the content
output was excellent. So thatmight be a spot for you to start,
which is just like contentabout local real estate. Because

(50:01):
one of the things I've noticedis, you know, to your point, Realtors
just want to sell, sell, sell.And oftentimes the only local real
estate content is coming fromeither a Realtor or a mortgage broker
or someone in the transactionchain that has a very vested interest
in selling you a property. Soit's always time is right to buy,
buy this house. Like there'sno, you know, there's no context

(50:25):
ever. And so honest. And thesecould be big asset classes, especially
in an area like you're at orwhere I'm at at the Jersey Shore
and in most towns. I mean,these are big asset classes. And
if you look at like finance orcrypto, there are how many public
publications covering thestock market?
Crypto.
Right. I mean, these arebillion, multibillion dollar, trillion
dollar asset classes that havelots of information and content.

(50:47):
And yet localized real estatereally doesn't have much. Maybe you
find some commercial realestate and like the big investments
in major cities, but like, youdon't find actual good information.
So from a content perspectivecould be an idea for you to consider.
But then it's like themonetization piece. It's like, are
you then do you become abroker? Do you work with a broker?

(51:07):
Do you sell leads? You know,you're in maybe a little bit of a
rental market. Like we have abig rental market. That's an opportunity.
No rentals here. Oh, reallyinteresting. Everything is Airbnb
now. It's. Yeah, so. Sothere's kind of this sour taste that
people have around realestate. I think there's a lot of
ways to do it. I think, youknow, from a content standpoint,

(51:29):
there's a lot of educationalstuff you could put out there. I
think if I ever got into beinga broker, it changes my relationship
with my subscribers. How do Imaximize? How do I move people down
this funnel? And I think thatwould actually be detrimental to
the overall mission of whatI'm trying to create. I don't want
to be having an event andbeing like, hey, if you ever want
to sell your house, like, hitme up. I actually had an acquisition

(51:52):
offer very early on from amajor real estate company in this
area, and their goal was toown this subscriber base in case,
well, when the time comes forsomeone to sell or to buy, this is
the place to do it. And Isaid, no, very quickly, would I ever
sell the business? Maybe. I'mhonestly not even considering that.

(52:14):
But I do think, like, whatwe're talking about from a real estate
standpoint, it's applicable toall the different niche, broader
or rather deeper plays. We canall go with newsletters, and you
have to look at it and say,well, which one's going to be fun
and engaging? Which one'sgoing to actually generate more value
for the subscriber? Which onecan I actually monetize? You know,

(52:37):
you have to be consistent longterm. Now there is another option
of what the future of localmedia looks like. And most of these
newsletters are individuallyowned and operated. Well, what it
looks. What does it look liketo actually have true contributors,
like a local news newspaperdoes? So you find the great voices
in the area that you like,that you think are authentic, and

(52:59):
you bring them on. And now,you know, through Beehive, you can
have, you know, contributorsand everything like that. So you
could actually streamline thecontent creation process. You can
have one focused on politics,one on real estate, everything like
that. And now people have thechoice of, hey, do I want to just
follow Catskill Crew or do Iwant to do Catskill Crew Politics?
You know, you have thesechoices and you're compounding the

(53:22):
ability to create content,bringing on different authentic local
voices and, you know, buildingdeeper relationships. Do you think,
you know, getting intosomething you mentioned a little
bit with real estate, then youinherently want to sell people stuff.
Politics is another one. Doyou feel like if you get into politics,
especially local politics, itcan be polarizing? Like, I think

(53:44):
it's a huge opportunity. Howdo you. How do you balance that part
of it? I'm not touching it.No, I mean, truly, I have no interest
at this point in time. The wayI look at the newsletter is Good
vibes only. Yes. I try to makethis thing very fun. I don't touch
things like, you know, we justhad a ton of forest fires up here
that didn't make nationalnews. I had one a couple miles down
the road. For me, I didn'twant to get into it. Right. Like,

(54:06):
that's not really where I wantto put my effort. People are getting
their news elsewhere now.Could there be a version of Catskill
Crew that's focused on newswhere I really try to focus on the
good stuff that's happening?Yes. I want this to be an oasis for
good vibes. I want this to bea place where people come for community,
for fun. Yes. To learn things.But that's very important to me.

(54:28):
You know, maybe eventually Istart Catskill Crew Bad Vibes, but
that's not a priority rightnow. You could just call it Catskill
Crew Politics and same name.Do you think you mentioned earlier,
like, you know, realtor wantedto maybe buy you guys? I have this
belief that I think a lot ofpeople were starting local newsletters

(54:49):
and this will kind of dovetailinto what you're doing in the community.
But I think a lot of peoplewill have successes building business,
getting ad dollars, hostingevents, and it will become a sustainable
business or side income forthem or turn it into a larger media
company. And then anothergroup of people are going to build
a list of 10 to 20,000 people.Kind of hit that point where, like,
it's a. Either go over thetipping point, you go over the top

(55:09):
of the mountain, or you fallback down. Just you're creating content
for not a lot of return, andthen they wind up selling it to a
local business. Talk about if.If you're a local business, the potential
in that maybe in eitherstarting one of these or acquiring
one of these. Or am I offbase? Like, do you think now that
that's not a world in whichlike, of these get acquired by the

(55:29):
local realtor or the localinsurance company or whatever it
is, the local ice cream shop,for that matter. I think they are
extremely acquirable assets atthis point in time. And I think that's
been validated through everysingle conversation I've had with
local business. You know, thedesperate nature where they have
no way to reach the customers,their customers, existing ones, let

(55:52):
alone new customers. So. Sothere's clearly an opportunity and
a value generated there. Theidea that a realtor came to me, a
bigger realtor, and offeredacquisition very early on was another
validator of oh, shit. Okay.Like, this is valuable. It is about
community. And it's one of thebest ways, you know, you can't just
start a newsletter and expectsuccess. And I'm going to use that

(56:15):
in kind of air quotes and veryumbrella term. But you need to engage.
You get out what you put in ahundred percent. And look, if you're
this kind of boring voicethat's aggregating some events and
there's no branding there,people aren't going to stick around.
You need to kind of find yourvoice. You need to find your niche,
you need to find your secretsauce. And, you know, that could

(56:38):
take so many different forms.But if you're able to do that, you
do create this defensive mode.You do create this further value
of if you do want to continueto grow this launch businesses, you
can. If you want people toshare, you know, and refer you, refer
you to other folks, you can.But if you don't have that, it's
hard to sell. Then you're justa list. And I think, like, the value

(57:02):
probably gets cut 75% there,you know, if it's not an engaged
audience. Yeah, that's. That'sa big part of it. There's a lot of
people with local lists. Andyou'll say, what's the open rate?
And they'll say 12, 15% and 3%click rate. And you're like, that's
not an audience, that's alist. There's a difference. There's
a different, different words.All right, Talk about what you're
doing in the community. Youhave the newsletter club. So when

(57:24):
I, you know, kind of plug thatand talk about that. You've done
some office hours on X. How doyou sort of see yourself? Because
this is one of the nice thingsabout this business is there's not
a lot of overlap. As long asyou don't find the guy who's starting
the oven, the other Catskillcrew. Right. You can kind of share
these learnings with peopleand, you know, kind of like both
you and I are doing, pickingup ideas along the way. And everyone,

(57:47):
like, you know, almost bydefinition has their own territory
and isn't going into somebodyelse's. Yeah. So, you know, basically,
to be pretty concise here, Icalled a friend of mine, Jason, and
I was like, dude, I did 10k.This was back in like July or something
or June. I did 10k this monthwith my local, local newsletter.
He's like, you gotta startselling a course. And I'm like, no

(58:09):
chance. But I did see theopportunity of like, wow, this is
significant opportunities to.It was enough proof that okay, I'm
really building somethingspecial here that I could go on to
do something much larger.Everyone should be doing this. And
so I decided to start thislittle club, you know, end of August
and people started comingtogether and I saw the idea of yeah,

(58:29):
this is not competition,competition. We are compounding this
knowledge. So, you know,every. The price increases in the
club every 10 spots, smallincrements. If you can't afford it,
I always say just hit me up.Anyways, I'm happy to be a resources
because I do want everyone towin. I mean that truthfully. And
I think it's really funengaging with everyone and hearing

(58:50):
their challenges and sharingwhatever I know as well to get them
a little further along. So,you know, the club is 64 of us so
far and you know, long waitlist and we're sharing tips and tricks.
There's mastermind classeswhere we're deep diving specific
topics. From sponsors to metaads to nurturing new leads. We have

(59:12):
a weekly call. We have, youknow, resources and digest. Continue
to grow this thing and thebeauty is everyone's coming at it
from different background,different experience, different different
geographies. However, even ifsomeone does come along, it is inevitable
that as this continues to growand proliferate, other people will
start local newsletters inyour area. As Landon from Wichita

(59:36):
Life says, like, you know,free market. I think it challenges
you to be better, to find yourvoice. And I don't think there's
anything wrong with twonewsletters being in an area per
se. I also believe thatthere's opportunities to coexist
really like in a symbiotic waywhere you're addressing this market.
I'm addressing this market. Ihave this voice. You have that voice.

(59:58):
You're focused on nightlife,I'm focused on parents, you know,
whatever the way it is thatyou guys could kind of work together.
But again these are brands andso naturally different brands are
going to have differentvoices, different personalities,
different end goals. So yeah,that's the newsletter club. It's
incredible. We got a lot ofstuff coming in 20, 20, 25 and yeah,

(01:00:21):
super pumped. If you want toknow more, you just the newsletter
club and how can. Peoplefollow you on X? That's I guess that's
your main platform, right?Yeah, I haven't updated my LinkedIn
in about seven years. MikeyPesto. I make good pesto. So, so
I I for then to plug youfurther, I first come across you
and you put out some of yourRevenue numbers. And I frankly, I

(01:00:42):
didn't believe you. Right. Iwas like, those are, that's crazy.
And then you DM me, you'relike, no, here's how we're doing
it. And then like we weretalking and you sent me the link
to the newsletter club, whichhas been awesome. A lot of, a lot
of good ideas. And I try tolike, try to pop in only a couple
times a day because otherwiselike, you know, then like you don't
leave and it like turns intolike a new Slack chat. So I try to
pop in. I know I'll givemyself like 20 minutes to look around

(01:01:03):
and then otherwise I get, getsidetracked. But there's a lot of
good stuff in there. So you'vedone a really nice job at kind of
building that group. Yeah,it's, it's been great. And you know,
I think like, what the futureof the club looks like is again,
I'm not chasing perfection.We're going to grow, we're going
to hit growing pains. We'regoing to adjust. This is run by everyone.
I'm just kind of likesupporting and facilitating it all.

(01:01:25):
And in terms of the revenuenumbers, you know, I think a lot
of people saw those numbersand were like, bullshit. And I would
probably say the same thing.However, there is a caveat here which
is like, look, that there's alot of stuff in the pipeline that
I've been building towards andit's not always consistent. Consistent.
I say no to advertisers allday long. I'll say no to like, you

(01:01:47):
know, I'd rather say no to abad advertiser and give, you know,
a small business or a nonprofit a plug because I'm playing
the long game. And there'sbeen months where I'm like, I made
a thousand bucks this monthand January, I have a lot in the
pipeline. There's Monopolyboards coming, there's a bunch of
events, there's a bunch ofsponsors who, you know, their budget

(01:02:07):
was allocated for 2024, sothey've lined up, you know, sponsorship
spots for 2025. There's moreproducts, there's more merch coming
down the pipeline. I'm reallyleaning into that. And that's been
validated through customersubscriber surveys that they want
more drops. So, you know,everything is a limited edition drop.
I think that's special. It'sfun for me. It's what I would like

(01:02:29):
to participate in. But youknow, I, I'm the first to admit,
like, I don't put much effortinto trad monetization. I know it
is there and I could pursue itdown the line. But like, you know,
I connect with tourism boards.I'm waiting for probably about $30,000
in ads, you know, sponsorshipmoney to be secured by tomorrow.

(01:02:51):
So, you know, I kind of ebband flow with that. And you got to
kind of find where yourstrengths are, where your weaknesses
are. And for me, it's reallyabout monetizing the community in
fun ways. And then do you guysknow anyone who'd like to sponsor?
Don't waste your time withsponsors who aren't serious. You
know, if they don't follow upon two emails, forget them. Just

(01:03:11):
move forward. You don't haveto chase them. There's enough small
businesses and high LTVbusinesses in the area. Be confident
in what you're building andmagic will happen. Yeah, I think
it's a good point to end on,especially building the brand. You
know, if you get the brandstrong enough and you have enough
reach and engagement, there'salways the opportunity. So you don't
need to chase it all the time.Awesome. Mike. Mike or Michael, I

(01:03:35):
don't care. I haven't figuredit out yet. Michael, thanks for.
Thanks for joining and yeah,we'll talk soon. Awesome conversation.
All right, so that was MichaelKaufman and pretty fascinating conversation.
I want to pull out a few itemsthat to me really stood out and are,
if you made it to this pointin the podcast, important for just

(01:03:57):
about anybody listening. Firstand foremost, the engagement on Catskill
Crew is absolutely insane. Thenumbers he gave when he had a thousand
subscribers and something like40 people show up to an event that
is 4% of the subscribers cameto a physical event. There are digital

(01:04:21):
marketing efforts out therethat get 10 to 12% open rates. Those
are just people opening anemail and maybe 2 or 3% clicks and
maybe one out of a thousandpeople might actually take an action
online. For him to get 4% ofhis existing base and maybe some

(01:04:43):
people brought friends. Soit's a little less than 4%, but the
point definitely still standsto a physical event in an area that's
kind of large, it's not asmall town, the Catskills. He described
how many, forget how manymiles wide. It was super impressive.
This is the importance ofbuilding an audience that is hyper

(01:05:04):
targeted, whether that's abusiness niche or location like the
Catskills. Because when youhave something for them to do an
action, you want them to takea place you want them to go, a product
you want them to buy or anadvertiser you want them to support,
you want to be able to havehigh pull through. And that is just
outrageous. The other thinghe's doing along the way, he's doing

(01:05:26):
this very smartly. He didn'tarrive at that event number by accident.
He polled people along theway. What do you want to do? When
should we do it? Where do youwant to go? And this is so easy to
do, you know, anywhere online,but particularly with newsletters.
Because you constantly canpoll people using the poll function
on Beehive. And then you couldbuild profiles and you could segment

(01:05:49):
the people who respond to yourpolls. And then you can not only
see the data, but contact themspecifically and ask them follow
up questions if you reallywant to get strategic about it. So,
point being is, he didn't luckinto these engagement numbers. He
is polled. He filtered out thenoise, he got the signal. And with
an audience even of athousand, usually poll results are

(01:06:11):
kind of statistically relevantenough to give you a pretty good
idea, especially for this,where it's just sort of back of the
napkin estimation, whereshould we have it? What day is best
really smart use of that? Andhe's continuing to do that with products
and services. He wants alaunch. He's asking people, do you
like this hat? What colorshould we use? And now the risk for
him when he goes to printthose or stamp a T shirt, um, it's

(01:06:38):
just, it's almost zero. Causehe's already had the audience to
find the product along theway. And sometimes you need to be
careful about listening to anaudience too much. Cause there is
a lot of noise there andyou're always gonna have people who
complain. So I would neverlook too far into any one individual
comment or response. If youstart getting quote, unquote haters,

(01:06:58):
that usually means you'rereaching enough people. And you may
see one person out of athousand say something truly terrible
or why an idea or product istruly bad, you can often ignore that.
And polling is a great way tokind of filter that out and aggregate
those results. And if you have20 people who are kind of saying
the same thing, then maybe youhave some signal there. But the engagement,

(01:07:18):
the polling, super cool. Thebusiness side of it, obviously there's
a number of directions hecould take this. And maybe he's a
little bit paralyzed as towhere he wants to go, but at the
same time, there's no rush.There's a quote, I think it's from
Warren Buffett or CharlieMunger about with investing. And
I would say in this case, whenyou're building a brand and launching

(01:07:39):
a new product. You don't needto swing at every pitch that comes
down the plate. You don't needto try every idea. You don't need
to invest in every stock thatcomes your way. You just need to
swing at the one that youreally like. And if it's a home run,
it can make up for three orfour missed opportunities in the
past. So what Michael is doingis he's thinking of these ideas.

(01:08:02):
He's polling his audience.He's finding ones that he thinks
would work, whether it's alocal business or a product or hat
or the Monopoly game that hewants to launch. And then he's finding
ones that have the mostupside. And he's saying, okay, I'm
going to swing at that one,and I know it's going to be a home
run, and it doesn't matter ifI passed on another one. So really

(01:08:23):
smart and obviously a numberof different ways he can go. And
I'm sure we'll follow up andtalk a lot more on the show about
what you can do building, youknow, whether it's a service business,
a product business, andprobably most importantly, and where
I'll leave this is how abusiness can launch one of these
local newsletters to growtheir own brand. Michael described

(01:08:43):
it perfectly. At the end ofthe day, he's just building a local
brand. And it's maybe startingoff as a newsletter because it's
kind of cheap and easy and canreach a lot of people. But if you're
smart, you could turn thatinto an established holding company
backed by your brand. And thiscan apply, you know, listen to his
background. He's not a writer,he's not a journalist. If you are

(01:09:05):
a financial advisor, if you'rea lawyer, a realtor, if you own a
flower shop, if you own apizza place, it really doesn't matter.
You could do this. The digitalchops to start one of these and to
write the content. The bar ispretty low. Doesn't mean it's zero.
You have to be good, you have.
To be engaging, you have to bewilling to stick with it. Because

(01:09:28):
it takes months, maybe six to12 months to build up an audience
like this. But once you haveit, you are now a brand. And I always
say you want to be the mosttrusted brand in town. So the lessons
here apply. If you have abusiness in an area or even in a
topic, and this specificallytalks to local media, just create

(01:09:51):
this weekly events newsletterand do it over and over again and
be friendly and Engage yourcommunity and then after a little
while, this newsletter issponsored by your pizza place, by
your insurance company. Andit's a soft sell. It's in every newsletter
at the top, in partnershipwith you, subtly let people know
that you operate thatbusiness, you develop trust with

(01:10:13):
them and don't treat it likedirect response. Don't expect that
every newsletter people willclick to have you advise on their
finances or buy insurance fromyou. That's not the way these things
work. Or even buy a pizza.It's just brand advertising. And
then when people are in themarket for insurance or just they're

(01:10:33):
hungry for a pizza, they'regoing to think of you and nowhere
to go. And they'll have seenyour brand so much that they don't
even need to open the email.They'll just know where to call.
They'll know which pizza placeto go to. Things like services like
legal, accounting, insurance,most people don't want to think about
those. That's where I thinkthere's a huge opportunity here.

(01:10:55):
And if they just trustsomebody, insurance looks the same
to most people. So they'rejust going to go to the agent they
trust or the lawyer that theytrust. It's really difficult to know
what's better and who's betterthan somebody else. And it's all
about trust. And you couldbuild that up with these local newsletters.
So really fascinatingconversation with Michael. If you

(01:11:15):
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(01:11:39):
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(01:12:01):
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