Building a Premium Local Newsletter: Insights from Geoff Sharpe of Lookout Media

Episode Transcript
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(00:00):
All right, welcome back toMonetize Media. I am Kyle Scott.
On today's episode, I talk toJeff Sharp, founder of Lookout Media,
which has three localnewsletter publications in Canada.
He has Ottawa, Lookout,Capital, Eats, and Vancity in Vancouver.
Just a really goodconversation with Jeff, who is approaching

(00:20):
local media from an entirelydifferent perspective than the way
many people are kind ofcurrently building local newsletters.
Most people right now arefocusing on lifestyle things like
events and restaurants. Andwhile Jeff is certainly looking into
the restaurant side, hispublications focus on civics news,
covering city hall, coveringthe issues that are important to

(00:40):
people. While many upstartlocal media brands have kind of stayed
away from hard news, Jeff isgoing all in. And because of that,
he's able to command premiumsubscribers. In fact, more than 75%
of his revenue comes from frompremium memberships that charge up
to a hundred dollars per year.And he has thousands of subscribers.
Great conversation with Jeffas we get into what premium content

(01:03):
means for local media, thebusiness models behind local newsletters,
and his thoughts on thenewsletter and digital media space
in general. Here now, myconversation with Jeff. Before we
get into it, let me ask you afavor. Go to your podcast player
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(01:24):
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we'll rank us up so morepeople can find monetized media.
Onto the interview with Jeff.All right, want to welcome in Jeff

(01:48):
Sharp from Lookout Media.Welcome to the show.
Great to be here.
So why don't. There was alittle bit of an intro there in the
beginning, but why don't yougive listeners a little bit about
your background and how yousort of found your way to the Lookout?
Yeah, so I'll just sayLookout's a local newsletter network
publication up here in Canada.Been around for just over three years.

(02:12):
My background is in sort ofdigital marketing. Run my own agency
for about eight years now.Worked on agency side stuff lot in
nonprofit charity world too,which I think there's a lot of interesting
applications to the localnewsletter space. A lot of it on
sort of like onlinefundraising, membership engagement,

(02:34):
things like that so dabbledin, you know, one of those digital
people that basically dabblesin a bunch of different stuff. And
you know, 10 years later Ifinally found the one thing I want
to focus on.
So you're local. Talk aboutthe three brands you have of the
lookout and describe theproduct a little bit because it is
a little bit different thanwhat I think a lot of people are

(02:55):
doing in local media.Especially like the newsletter centric
local media we've seen andtalked about a lot lately.
Yeah, it is a bit different.Maybe I'll just talk through where
we are and a little bit of howwe're different. So we're right now
in two cities. We have a localnews publication which covers the
news in the space. Talk moreabout the specifics on that after
then we also have a foodpublication in each city. Kind of

(03:19):
differs. In Ottawa, which is abig city up in Canada, we have a
separate sort of website andfood publication for that that does
very specific, like actualrestaurant reviews, goes and tries
the food. Very different than,you know, this sort of like listicle
summary type stuffintentionally. And then the news
side of stuff is more on the,more on the journalism side than
what you might see with sortof what's happening in the local

(03:41):
newsletter space right now.The way I've approach over the years
and it's changed, which wecan, you know, definitely talk about.
I've had a lot of theories andthat haven't been proven out and
I think we finally found themodel that works. But it's more on
the journalism side andthere's a specific reason for that
on from the revenue side. Butbasically it's a product that goes
out three times a week. It's asummary of what's going on in the

(04:02):
city with exclusive newscoverage as well, specific stories
that are, you know, our teamis going out and finding very similar
to like a local, like atraditional local news publication.
But it brings a lot ofdifferent things together in the
sense of marrying thetraditional journalism stuff with
engaging with an audience, youknow, good email, best practices
for audience engagement. Andso the product itself includes events

(04:26):
like a lot of these otherlocal newsletters are doing. It includes
news summaries and then wehave a very civic product in each
city that's kind of the samewhere it's, you know, you've got
the events, you've got thelocal news summaries, we've called
them like community highlightswhich are essentially just, you know,
what groups are doing littlefun little stuff. We have, you know,
house of the week. A lot ofthe stuff that you find in these
other newsletters, but it isanchored by a more robust journalism

(04:50):
aspect to it. And partiallythat comes from just my experience
in that world and, you know,having worked with journalists in
past jobs and things likethat. Not, you know, not everyone
can do that, obviously. Butthe big reason for that is because,
and this is what we're seeingwith a lot of local newsletters,
it's very hard to driverevenue from individuals. Ads. Great

(05:12):
business, super profitable,but getting people to contribute
or purchase stuff can besometimes a bit of a challenge. And
love to explore that more. Butwhat we found is people are willing
to pay for good journalismthat dives deep into some of these
issues. And so I'll end it bysaying our revenue is quite different
than other platforms. About75% of our revenue comes from membership,

(05:34):
about 25% from ads. And wedon't really have a set like outreach
strategy for advertising. It'skind of a thing we need to work on
in the future. But yeah, a lotof it is membership based. So I'll
leave it there by saying,yeah, we're a little bit different
than some of these other ones.
Yeah, yeah, yeah. So there's alot there and I'll call out a couple
of things that I heard there.So I think first, so many of the

(05:54):
local newsletters that arebuilding on Beehive, which are definitely
having a bit of a moment rightnow, have really keyed, keyed in
on the lifestyle stuff.They've followed a little bit of
the, I think 6am citiesplaybooks, a little bit like this.
They kind of talk about notwanting the ruffle feathers, not
wanting to dig into politics,lifestyle, restaurants, events, things
like that. They move theneedle. It's useful for people and

(06:16):
obviously it's a pretty easybusiness model. I think the downside
of that is it doesn't give youa great moat. You're performing a
service, but it doesn't reallyprevent anybody else from coming
in and doing it. One of thethings we're doing in Philly with
Access Media is we have abunch of traditional websites and
we're kind of building out thenewsletter component, but we cover
everything. The lifestylestuff, but also the, the accident
and the crime. We try tobalance that mix. You guys, you guys

(06:39):
really double down on thecivic stuff. And I, I'm, if I'm hearing
you right, that kind ofconnects. You know, you have a lot
of, I think you said 75% ofyour subscribers, you told me, are
Premium subscribers. I'msorry, 75% of your revenue.
Yes.
Yeah, is, is premiumsubscriber revenue and I'm guessing
that has a lot to do with,with the civics coverage. Each. If

(07:01):
anyone goes to your site,lookout mediaco.com and clicks on
some of your newsletters, Imean, these are long, they're like
meatballs of newsletters withreally in depth, well structured,
easy to read. Even as anoutsider who knows nothing about
what's going on in Ottawa, Ifound it very easy to read. But talk
about why it's important foryou guys to go so in depth on so
many. Like I read a nichetopic about, you know, whether, whether

(07:25):
a city like Ottawa was readyfor snow, which I found kind of humorous
but also really interestingfrom a local politics angle and how
you use that to drive premiumsubscribers, which makes up a majority
of your revenue.
Yeah. So I'll just say quicklyto find it. If you want to see some
of The Stuff, OttawaLookout.com, best place to find it.
Each city has its own sort ofunique URL, whereas our, you know,

(07:46):
our whole company has its own,you know, own URL. But yeah, so getting
membership revenue is prettytough and we definitely have made
the decision to do that. MaybeI'll back up by saying that like
when my business partner who'sno longer with us, he's going off
and doing his own thing now.But when we started it originally
the idea was it would be alittle bit lighter in that sense,

(08:08):
it would be more. Here's aquick summary of the news. Like,
yes, we have news stuff, butyou know, 40, 30% of the stuff will
be a little bit lighter. It'llbe more of a fun experience for people
to engage with. I think, youknow, I had seen 6am City, I had
seen Axios and was trying tomarry a little bit of the two together
to create something different.And you know, just generally speaking

(08:28):
in Canada there's not a lot ofnewsletter based publications, a
lot of traditional stuff. Andso you see what goes on in the US
and you think, oh, this is,you know, very easy to apply up here
in Canada. What we found overtime is that, you know, my experience
has been in driving andturning, you know, readers and stuff
into members and payingpeople. Pretty hard to do with lifestyle

(08:51):
content. There's a lot ofbenefits to focusing on that, obviously.
One being not everyone can dohard news journalism analysis, things
like that. That's just thenature of it and totally understand
why people do, you know, focusmore on the lifestyle content. And
then in a lot of placesthere's not a lot of actual lifestyle
content in the sense thatthere's no competitors. And so it
makes total sense to focus onthat as a main product. You know,

(09:15):
hard to find events in some ofthese communities. So you're meeting
a real need there. For a lotof places in Canada, in a lot of
the cities, they do have apretty robust lifestyle coverage.
You know, we have our, I don'tknow what the comparison would be
down the US but you have yoursort of listicle sites, the ones
pulling together events,things like that. But what you find
is that a lot of times that'snot high quality enough content to

(09:37):
push people along in anengagement type way of like from
just a reader to actuallydoing something. Now I do see a lot
of examples and you'veinterviewed a few people and others
who are able to take some ofthis lifestyle stuff and turn it
into people attending eventsand things like that. And that's
awesome and huge there. Kudosto them because that's still something
we're working on from acapacity standpoint.

(10:00):
It's a different lifestyletoo. You have to a be really creative
about it. But you also theeditorial team in a lot of these
are one or two person shops.You have to be willing to be in the
events business so it canwork. But it's also, if you want
to be a reporter, those tendto be two different hats. The people
who want to report and thepeople who want to go to happy hours.
Frankly, totally, totallydifferent thing. And that's I guess

(10:21):
where we, we came from. Justhaving a bit of experience working
with journalists and thingslike that where it's like, okay,
we know how to work with thesepeople, we know what gets people
going. And I think wedefinitely started out thinking with
being more lifestyle and likeon the food side too. We were like,
we'll just do listicles. Like,you know, we'll summarize that. And
what we found over time isthat people are just willing to engage.

(10:42):
And this is not anything new,but people are willing to engage
more with like very in depthjournalism and stories that help
them understand their city andexplore issues that they just aren't
aware of. What that does is itreally moves people farther down
the engagement ladder ofbuilding that trust and seeing the
things that are happening andbuilding that relationship with reporters

(11:03):
and you know, people writingthe newsletter in a way that you
just can't do as a traditionalpublication. So the way it kind of
has evolved is taking the bestparts of news gathering and journalism
and marrying that with sort oflike the, the newsletter piece where
you can build thatrelationship, you can have that consistent
habit with people and it turnsit into a product that is just so

(11:24):
effective at taking peoplefrom being subscribers to being someone
who's willing to pay, youknow, a yearly or monthly membership
to support the work becausethey're seeing what type of stuff
you're doing. I think thechallenge with turning readers into,
into paying members, you know,I see this a few times with some
of these local people and notmeant to be criticism at all, but
doing these sort of likediscount cards and other things and

(11:47):
it's, you know, sometimes theywork. I've seen a few times where
they haven't sold out oncertain things. And it just goes
to the fact that it's reallydifficult to monetize the payment
from people on the lifestyletype stuff versus on the ads, which
is a great, you know, greatbusiness. But taking it from that
to that is really challenging.And I've talked to a few people about
this and how they're thinkingabout it. It is a challenge to do

(12:11):
and, you know, I think peopleare starting to figure it out. But
there is something to be saidfor sort of like an older model of
doing things. And that's notto say that everyone can just spool
up a local journalismpublication. Like, like I said, you
know, there's certain thingsyou have to do. But I think there
are some lessons here aroundlike flight to quality being really
important. And your pointabout a moat as well is just critically

(12:32):
important. The only thingstopping someone else from starting
another local newsletter inyour space if you're just summarizing
events, is having more moneyto run on ads. Right. Because it's
cheap, it's easy to do. Somaybe that's a motive in and of itself
that no one has those skills,but it's a, it's a. Certainly a challenge.
And I think some of the localpeople in the space on Beehive especially
some of them are starting tofigure it out and do really well

(12:54):
from like a brandingperspective, sort of differentiating
it that way, making the personsort of central to that. I think
a good example of someonewho's done that really well marrying
a lot of that is like the Lifeof Scoot or the Ryan Sneddon. Yeah,
Ryan Sneddon, exactly. I thinkhe's done a good job there of sort
of marrying the different things.
Yeah. So I've talked to. Ithink I've talked to Ryan once or

(13:16):
twice, but I followed himonline and my sense is he enjoys
that he, he thrives on that.He likes being the guy and you know,
for the certain type ofpersonality that works. But there's
also a lot of people who, whodon't want to be out impressing the
flesh. You know, some of usare digital media people because
we like sitting at home behinda desk 20, 28 hours a day. Let me.

(13:41):
There's a. So there's a bunchthere. I want to kind of talk about
the growth aspect of thisbecause I agree with you that you
got this premium contentreally in depth. And I want to kind
of talk about the kind ofjournalistic angle you guys take.
But to get people to pay for asubscription, there is some level
of marketing, some education,a bit of a sign up flow. So talk.

(14:08):
I'm sure a good number ofpeople listening to this either have
newsletters or online brandsand will be interested in how you
sort of nurture that personfrom the first touch point the Lookout
has or Ottawa Lookout has andthen how you sort of funnel them
down into a paid subscriberand then even into the, you know,

(14:28):
do you lead with the lifestylestuff or you lead with the news brand?
Just talk through that whole process.
Yeah, so maybe I'll start atthe 100 foot level and then work
down to sort of the tacticalpiece that supports that. I think
the way like obviously you'retrying to solve a problem for people.
So like on a lot of our adsthat we acquire people on, it's like,
you know, do you struggle tofollow local news and events? You
know, sign up. That's the veryfirst, you know, touch point. It's

(14:50):
a transaction, it's verysimple. You're solving a little bit
of a problem. What then yousort of get into. And I like to think
of it as sort of like it'salmost like you're telling a story,
right. Like if anyone can goand just search for local events
or if there's other local newscompetitors, you kind of have to
try to differentiate yourself.Right. That's through format. But
a lot of it is sort of thestorytelling aspect. So the story

(15:12):
that we're telling people isthat local news is broken. There's
a lot of pop ups on websites.It's a really annoying experience.
It's brutal to find stuff. Youknow, there's always paywalls stopping
you from seeing stuff. And wewant to try to make it as easy as
possible. And we also reallyemphasize sort of the mission aspect
of it too. And I think that'smaybe an under emphasize peace. So,

(15:33):
you know, we're talking abouthow we want to fix local news, make
it, you know, help uncoverthose issues that people aren't finding.
And the storytelling takesplace throughout sort of the entire
duration of the experience. Soin the introduction of the newsletter,
we talk about, oh, somestories that we're pursuing, you
know, maybe you want tocontribute, you know, what do you
think about this? And youknow, we just saw this local newsletter,

(15:55):
local news publication, Fire50 People. You know, that's we're
not about that, we'redifferent. And so it's kind of you
need to figure out what yourstory that you're trying to tell
people about, who yourpublication is, what you're trying
to solve, how that helpspeople. And then, you know, it really
is sort of a narrative drivenpiece. I know it's kind of like pie
in the sky thing, but ifyou're in marketing or anything like

(16:15):
that, you know how powerfulstories are and you kind of need
to apply that to what you'redoing locally. Now ours is very mission
driven. You know, we're tryingto solve a big problem, but you can
apply that to anythinglocally. Right? Like there's different
ways to tweak that message.Maybe it's more of a personal thing
where, you know, you found aproblem and you're trying to fix
it for people locally or helpthem do that. You're trying to bring

(16:36):
people along. So it's morethan just a utility product. It's
obviously lifestyle is not theright word, but it's something that
people care about beyond justthe transactional utility element.
I'm a big believer that therehas to be some sort of story, emotional
connection to what you'redoing on how do you turn actual people
into members and stuff likethat. For us it's, it's. We offer

(16:58):
extra, extra stories that areunpaywalled. That's not a lot of
time. It's not a big reasonpeople join. They sort of, again,
it goes back to seeing themission and what we're doing. But
the way I sort of describe itis like you're taking a campaign
approach to asking people tobecome members. So what you find
with a lot of publications isthey'll just send a one off email
and be like, hey, you know,I'd love if you could like, you know,

(17:20):
buy me a coffee or contribute$5 to help with our mission and our
journalism. That can work fora little bit. But really you have
to start thinking about it assort of like a multi touch point,
essentially marketingcampaign. And so the way that we
approach that is like we havea goal that we're trying to achieve.
We've built that relationshipand that sort of mission with our
readers so they understandwhat we're doing. We have that relationship.

(17:43):
So when we go to them and saywe need 20 new members at the end
of the month to write this newstory on this, they trust us to do
it. They know we're going todeliver and they see the value of
what we're trying toaccomplish. And so we use the introduction
to do that over a month. We'llinclude like ad, not ads, but the
messages, like the ads inthere. We'll send one off emails

(18:05):
to do it. And so yes, thepiece of content that people are
getting is important. Yes, thepaywall is good because they're seeing
the stuff that they might bemissing. But I think with the local
news stuff there has to bethat mission oriented piece. And
that works really well with along term, multi week campaign where
they're constantly seeingthese things and seeing the progression
of this going. And that's whyI say my experience in like nonprofit

(18:28):
and charity fundraising hasbeen very useful because that stuff
really applies nicely totrying to get people to actually
do something and move themfrom just being, you know, an engaged
reader to someone who'swilling to become a member.
So yeah. So your initialoutreach, are you guys doing Facebook
ads to kind of get them infree subs? And then they get a certain
amount of issues andeventually it's like, you know, you

(18:48):
just gotta, you gotta pay toread this.
Yeah. So just how that workstechnically, like I would say 95%
of our audience comes fromsocial media ads. I think kudos to
the people that have solvedthe referrals and stuff like that.
We haven't had a lot ofsuccess, success with it and just
frankly it's a lot of paidads. But we know that they're incredibly
engaged audience beehives, youknow, very useful for that from a

(19:09):
audience engagementstandpoint. And so they're just acquired,
they go through an onboardingjourney. But a lot of it is like
the content they're gettingeach week. Right.
And so eventually get anewsletter that's like, you know,
they'll get the first coupleof paragraphs and then now you gotta
pay.
So the way, the way that worksand we're experimenting with the
model and that's sort of stillwhat we're figuring out. But basically
they get three freenewsletters a week. There's content

(19:32):
in there that is sometimespaywalled. So if we're re upping
old stories that arepaywalled, we'll include that. But
each sort of two to threetimes a week we'll do a really long
form story that is partiallypaywalled. So about 75% of it is
free and then the last 25% ispaywalled. And so to get the whole
story, to get it later, youhave to become a member. But a lot

(19:53):
of it is like, oh, I, youknow, these people are doing really
important work, therefore I'mgoing to contribute. I think when
we first started out we hadthis idea that like, hey, people
will pay for restaurantreviews. They'll pay for, you know,
extra of the same content. Andthat is a big mistake I think, is
that one, the lifestyle stuffdoesn't convert well on members.
Like we found that from evenlike in depth restaurant reviews.

(20:15):
And then two, yeah, lifestylecontent is tough to convert on. So
having the longer content isreally, is really useful. How would
that apply for like a localnewsletter that's just doing events
and other things? I don'tknow, maybe it's like a deep dive
on history or something likethat. If you're a decent writer,
there's, there's other ways todo it. But yeah, it's, I would say
about 90, 85% of the contentis free and then about 10 to 15%

(20:39):
is paywall. That's going tochange over time as we bring on more
reporters and do morepaywalled stuff. But for right now,
yeah, a lot of it is free.
Yeah, you mentioned sort oflike who's cracked recommendations
and I mean it certainly seemslike everyone in local who's trying
to build a local audience useFacebook, it's where the local people

(20:59):
are. And the zip codetargeting is obviously really good.
I think some of the tools thatexist for newsletters now, Sparkloop,
Beehive, Boost, these things,they can be good, but they don't
really work on the local levelbecause they only work because you
can tap into an ecosystem ofhundreds of thousands, millions of

(21:19):
people across the network onthese platforms. But that doesn't
really apply to local. Andit's hard to get, you know, it doesn't
make sense to refer someone toa, from a local to a very general
newsletter. And it's almostimpossible to have another newsletter
that has enough people in yourarea where it makes sense for them
to refer to you. And it's atough nut to crack.
And it's a good point. Likethe tools of growth that are really

(21:42):
advancing on the newsletterside are not great for local. But
I would Say the monetizationtools are quite good. So like you're
almost dealing with a onesided marketplace in the sense that
you're not acquiring frompeople, but you can send them out.
So I use Sparkloop, I'll useBeehive Boost to send people. The
thing that's reallyinteresting is like the local audience

(22:04):
you're acquiring is veryengaged and so you can send them
to the Sparkloop referralwidget and get, you know, some revenue
from there. We get a decentamount from that on the post signup
process just because it's moreengaged. And the really nice thing
is you're not competing withother people. So if you're an AI
newsletter and you're runningSparkloop stuff and you're sending
people to other AInewsletters, like that's a, that's

(22:24):
a brutal process to try tostay the top, you know, newsletter
and product in that space. Butif you're just a local newsletter,
you're not going to becompeting against other Sparkloop
local newsletters in yourspace. Right. So it's a great monetization
tool without, potentiallywithout some of the downsides that
come from. And there aredownsides to those sort of recommendation
engines.

(22:45):
Yeah, no, no, agreed. A lotof, I think local newspaper or local
newsletter operators and I'veheard them talk about it, I've heard,
I think Ryan Heaphy did awebinar with Beehive and I love what
they built and I think it'ssuper interesting guy, but he said
specifically he's like, wedon't want to kind of poke the bear
on these more important topicsand you know, look, you could build

(23:08):
a, it's, it's the old, I put atweet about referencing this yesterday,
but it's the old inch deepmile wide vs inch wide mile deep
thing. And you can go muchwider with the lifestyle stuff, the
light and breezy stuff. Youcan get a big audience and if you're
good at ads, you're good atevents, you can actually build a
pretty scalable business.Difficult, but it definitely can
be done. 6am Cities, a goodexample. But on the flip side, our

(23:30):
biggest local newsletter, wehave one in Ocean City, New Jersey,
Walking the Boards. Kind ofour, you know, flagship model we
use for, for the rest of ournetwork. And I put out an end of
year survey and we got about18,000 subs and it's been going out
for almost two years. Sothere's a lot of, you know, it's
pretty well establishedaudience. And I said, which sections
do you enjoy the most? And wegot pretty, you know, heavy response

(23:53):
from people who've beenreading a long time. And Hard News
was like far and away numberone. And I was surprised because
I see interaction. I see a tonof interaction and link clicks on
events, like a ton. The realestate stuff is interesting, new
restaurant stuff always getsshared. But everyone was like, hard
news, hard news, hard news.And it's. And sure enough, we're

(24:15):
in a town that doesn't havereally the only other coverage is
our sister site. So there'snot a lot of coverage news. And when
stuff happens, it's kind of asleepy town. So when stuff does happen,
people want to know about itand they want to know about it and
they can't go anywhere. And Iwas surprised to see that. So I do
think to your point, overtime, that does help kind of build

(24:37):
a moat. Because if you'rebringing people quality reporting,
you seem to take it a stepfurther, though. From the few articles
I read through, you guys seemto interject some opinion there,
some analysis, somecommentary, which I love. I can't
write anything on the Internetwithout letting my opinion come through.
But a lot of news publicationsare not only afraid to touch this

(24:59):
stuff, they're afraid to putany sort of opinion. You guys do
that and I'm guessing, buildup a lot of influence and talent,
talk about that aspect of it.
Yeah. So the one thing I dojust before I jump into that, I do
want to say one thing that'sreally been on my mind a lot is that
I do think there is a tendencyfor places to go 100% on what the
audience says they want. A lotof times it's like, we want events,

(25:22):
we want this, we want that.I've seen a few places make pivots
from doing journalism stuff todoing only events. And they've lost,
lost members and they've lostengagement. And there's something
to be said for you as afounder or a person running a media
publication, to take your ownideas and editorial approach irregardless
of necessarily what theaudience says they want. Because

(25:42):
the audience will a lot oftimes say they want more events,
they want more restaurantopenings, but for us, that doesn't
turn into paying members.Right. So as a person who's running
a local newsletter, the mostvaluable thing you can trust sometimes
is, is your intuition and yourbelief and what you're bringing into
the newsletter rather thanjust what your audience says. So
I would say, like, be aware ofthat. In our case, everyone always

(26:04):
says they want More events.But if we only did events or mostly
the events, we would not have2,500 paying members or almost 100,000
email subscribers. We just wouldn't.
And you have to have tastewhen you build an audience. You typically
build an audience because youhave some taste. You're able to interest
them in some way. And yougotta, you got to assume that out
of all the people readingthere is some wisdom in the crowd.

(26:26):
But like you're, you are theexpert at this and like you know,
go with your instinctssometimes you probably often know
better than sum total of thecomments to put it nicely.
And we'll get, we'll get backto that opinion analysis. But just
a point on that. I do thinkthe taste in and of itself is a differentiator.
Especially in this world of AIwhere you know, you can produce so

(26:46):
much of this stuff if you'vegot a unique view viewpoint. And
I think that'll tie into theopinion analysis stuff that we're
talking about and a uniquesort of taste and appreciation for
things that comes through inthe content. That is going to be
the easiest way to beat back alot of the AI stuff that we're finding.
You know that's going to betough if you're just a local newsletter
that just does a summary ofevents when I can go on chat GPT

(27:07):
and get the next 15 events.Right. So thinking about that's really
important. But you know, toyour point about editor has his.
Do you have photos in thethere right? You guys have your photos
almost like column style whichI love. Ryan Sneddon does that too.
I like that.
It's a great hack. We actuallylike started doing it in the last
four months and the number ofpeople coming up to our team is just
much bigger. So your point onopinion and analysis is a really

(27:30):
important one because I thinknot to get too high minded but I
think one of the biggestproblems with journalism is lack
of trust. And you build trustthrough good journalism, but you
also build trust throughpeople. Right? There's this whole
discussion about brands versussubstack people versus how you do
that. I think the combinationof all of them is what works best.

(27:51):
And so with the opinionanalysis like we. One interesting
thing is you do say opinionbut most of our audience doesn't
think of what or even notethat a lot of it and almost none
of it is opinion. But it'sinteresting that you noted that it
seems like opinion becausewhat it in fact what it actually
is is just an attitude or asort of like I think the better word

(28:12):
is personality. Thepersonality comes through and that's
what builds the trust beyondjust the good news and content that
you're doing. So if you'rejust doing local events, how do you
add personality to that? Howdo you add sort of. That's a way
to break down some of that andbuild that trust. Right. So, but
what I would say is that likewith Lookout, what we tried to do
is bring that analysis andsort of like journalistic thought

(28:35):
and sort of thinking aboutwhat the future holds and trying
to bridge that gap with like,what, you know, like an Axios is
doing or what a Puck news isdoing, where it's beyond just here's
the issue. It's what thisissue means to you. Because that
sort of analysis and insightis harder to get from just someone
writing a, you know, a trafficsummary story. Right. And that helps

(28:56):
us differentiate between whatwe're doing, doing. And it's totally
hard for some journalists todo that, like, totally get it. Like,
they've operated in a certainway, but that sort of an analysis,
and especially in theintroduction piece too. And like,
you know, at the end of thesestories, we do. It's a way to build
a connection with readers andbuild that trust because they know
who you are, they know whoyou're coming from. Rather than just

(29:17):
a faceless journalist writinga story. Maybe it's a good story,
but a faceless journalistwriting a story at a faceless branch.
Right. So I think your pointabout opinion and analysis is really
spot on. It's taking it beyondthe story and building that personal
connection through insightsthat you can't really find anywhere
else or these other placeswon't do because they just, you know,
that's how they've operatedfor a long time.

(29:38):
Yeah, yeah. And I've comeacross, you know, journalists, good
ones, who I like and workwith, but, you know, they're very
rigid on. It's not necessarilyboth sides. Ism. Some people try
to get exactly 50, 50, whichI. It can be good and bad. Right.
There are sometimes issuesthat deserve a 9 to 10. Right. And
you can pick your examples.But if you look back, people always

(30:02):
want to hearken back to thegood old days of journalism. They'll
cite on tv, like Cronkite orMarrow. Right. But those guys, they
would, I don't want to saythey had their own. They would interject
their opinion, but they would,I would say, charitably contextualize
the news. And I thinkcertainly in a world of AI, which

(30:24):
I actually do think localnewsletter Local media is a little
bit Teflon for that for alittle while, because AI needs source
material and a story about thepresident or the White House or the
stock market, there's going tobe enough source material for AI
to do a really good factualjob. Both local news, especially
the type you guys are doingwhere you're actually doing hard

(30:44):
reporting. The AI today can'tshow up with a notebook. It might
be able to listen to a citycouncil meeting live, but it's never
going to do that good of ajob. But then you guys are going
the extra mile and kind ofcontextualizing it. And I think the
average person doesn't evenhave that strong of an opinion on
some local news matters. Andthey're actually looking to someone
who's like, well, darn, you'recovering this. You must be an expert.

(31:07):
So what do you think thecontext this needs is? Do you guys
find that people actuallyappreciate the fact that, all right,
you guys probably know moreabout it than they do, so help me
contextualize this so how Ishould understand it and how it may
or may not impact me?
Yeah, People are screaming tohelp to understand what this stuff
means. Right. People are busy.They've got family to take care of,

(31:29):
they've got jobs they have togo to.
And it can be wonky. Like,very wonky.
Yeah, Like, I don't know, someof our stuff goes really deep on
this stuff, but because it's aconsistent product, it takes five
to seven minutes to read. Someof our longer stuff's a little bit
longer, but it's sort ofconsistent that way. The trust is
built up there. Theyappreciate and see that sort of like
analysis and rigor that'staken to these things and is just

(31:50):
different than what others doit. And I think to your point on
AI too, just, I mean, AI andother stuff is not going to tell
you how good a meal was at arestaurant and the type of ingredients
that they did. They're notgoing to be able to tell you that
the local.
Not yet.
Not yet. That's true. Not yet.They're not going to be able to tell
you. Like, was that localopera actually that I visited recently?
Was that actually really good?Maybe we'll get there eventually.

(32:14):
But I think what, what helpswith that and ties into the analysis
and that type of stuff is thatthere's a person there and there's
a person that's trust has beenbuilt up through this habit that
they're. That they'reexperiencing. And so I think that
the person is the way to breakdown that sort of, like, you know,
stuff that might come from AI.Right. And so, yeah, I mean, lots

(32:35):
you could talk about that. ButI do think your point on the. On
the. On the traditionaljournalism stuff is it's tough. And
that's why I think a lot ofthese bigger publications are really
struggling, because, one, theycan't pivot to doing some of this
stuff. They've just done, youknow, the traditional things. Two,
they don't have the team orthe younger people who are in positions
of authority to be able tosay, hey, like, this is what actually
people want. And the otherthing is like, they just never really

(32:58):
had to care what an audiencethought. Again, to my point, you
shouldn't follow 100% whatyour audience wants. But the product
that we're delivering is muchbetter than just a newsletter full
of links. Right? Just whatmost of these places are doing.
Yeah. All right, so we talkeda lot about the content. Dig a little
harder on the business side.So why don't you talk about. Listen,

(33:18):
I'll take as many numbers asyou want to give. I think would be
great and helpful for people.But, you know, feel free to stop
yourself where you want to.But what do you guys charge monthly,
yearly, and then what's kindof the breakdown of monthly to annual
subscriptions? And maybe start there?
I think it's like 85% annual.So the annual is the best way to
do it. There's been lots ofstuff on this, but you see from some

(33:40):
of these, like Jacob Donnelly,Simon Owens, some of these other
people are reporting on this.Annual stuff is a lot better from
a churn perspective thanmonthly. Every month you're seeing
$9 on your card, and you havebasically 28 days to prove every
single time that this is worththe value. And that's really hard.
Annual is really great forthat. We charge different pricing

(34:05):
per city. It's about $125 ayear at Ottawa. It's $99 in Vancouver.
And that's just because thelocal media markets there are very
different Ottawa. There's alot less independent news, a lot
more competition in Vancouver.So our ability to sort of like charge
higher is less. And we've justseen that from running it for a couple.
Couple years in terms of, youknow, the nice thing about having

(34:27):
a network of local news sites.And by network, I mean two. Right
now, though, we're hoping toexpand. We're planning, lots of planning
to expand more. You can seethe differences in each city. So
what the churn rate Is therehow long people are staying, audience
engagement, how do theycompare? So you can make those decisions
in each city about how muchyou should charge or shouldn't charge.

(34:48):
We do a lot of discountdiscounting. Not too much in the
sense like I've never done a$1 a year subscription or $1 every
six months, whatever. I wouldlike to try that at some point. But
we don't produce enoughpaywalled content, I think to warrant
that based on the places thathave seen success with it. What we
do is like, you know, 10%, 20%end of year we'll do a bigger discount.

(35:12):
A lot of our revenue. I saythis in a lot of our fundraising
emails, about 25% of ourrevenue comes in December because
we're running our year endmembership drive then and we again,
going back to what I talkedabout before, you're framing that
around sort of a mission ofhiring another journalist or the
plans for the new year. And soeveryone's primed to make donations
then. It's a big. Forcharities and nonprofits, it's the

(35:33):
biggest time of the year. Soyeah, we'll do discounts. Churn rate
is like quite a bit higherthan what I want and that's more
of a function of just, youknow, figuring out what's going to
make people stay and havingchanged the model a little bit. So,
you know, our churn is kind ofbetween like 10 to 20% per. Sorry,
no, like 15 to 15 to 20% peryear in terms of members churning,

(35:56):
which to me is too high, butis pretty standard for the industry,
it seems like based on whatI've read. So, yeah, I mean, we're
growing pretty consistently,but there's more that needs to be
done on that front in terms ofkeeping people, keeping people subscribed.
Have you guys thought about.I've seen some people talk about
lifetime subscriptions. Thelonger, you know, the longer you
can get people, the lesschance, to your point, they have

(36:17):
to cancel annual is the bestway. But if you thought about lifetime
or any idea what you wouldcharge, it's a. I don't.
So I think that is a goodopportunity to do it. I think the
challenge is I don't thinkwe're producing enough exclusive
stuff to make it valuable yet.I've got a very like long, long term
view about these things. Andso like to be totally transparent,

(36:39):
like, you know, we don't haveany investors, like no outside funding.
We just did it off the side ofour desk. So we can grow as quickly
or as slowly as we want. Sothere's not an impetus to try to
get as many, get as muchrevenue, get as many, turn as many
members as possible within acertain amount of time. Obviously
we, we've got a lot ofplanning, but it means that we can
be a bit more slow about whatwe do and build that up so that when

(37:01):
we get to, you know, we'reproducing like maybe an exclusive
story every single day thatchanges the dynamic a little bit
about what we could charge andyou know how we might add it. So
no, like roundabout way. Wehaven't done lifetime subscriptions
yet and I don't think I woulduntil we have more content there
to warrant it.
I guess that's fair. Now yourwebsite says join 1700 Ottawa Lookout

(37:22):
members. Is that a roughlyaccurate kind of paid metric?
No, that was before we did ourend of year campaign. So we're at
between the two publications,we're at 2500 paying members.
Okay, so all right, so you guys.
Are well, 93, 94,000 emailsubscribers between the two of them.

(37:42):
So you guys are well, well inthe six, six figures with the paid.
Yes. Yeah.
And then so you said that'smajority of the revenue, maybe 25%.
20, 25% is other things adsupported. So talk about the rest
of that mix. I know it'ssmaller. Obviously you would like
to grow all revenue over time.Do you think about trying to balance
those mix? You have the foodvertical which feels like maybe it's

(38:06):
a little bit more leans intothe ad side. So maybe talk about
that side of it. The morelifestyle stuff versus the in depth
premium stuff.
Yeah, we don't do any outboundad sales and that's just a function
of we just don't have aperson. And my time is spent generating
membership revenue which inthe long term is a consistent, you
know, if we're losing 20% ayear, that's a great spot to be in

(38:26):
for recurring revenue. Right.So 25% is ads about, I don't know,
30, 40% of that is likeSparkloop, beehive ads, referrals,
things like that. The rest isjust inbound organizations asking
to run ads basically. And so Iwould be the first to admit that
there's more we can do on thead side. I think in the long term
I'd love to. Not that I wantto flip it to 75% ads, but you know,

(38:51):
the way I think about it islike the memberships and again, this
is just unique to us in thislocal newsletter space. You know,
the memberships are what Payall the bills and keep the lights
on and allow us to besustainable. Whereas ads is sort
of the icing on the cake andwould be the big growth lever to
drive the organization forwardto like real, like really, really

(39:11):
big revenue. That stuff you'reseeing in some of these other places.
So you know, we're in theprocess of hiring an ads person.
Our hope is that that's goingto be sort of a main driver in the
future. But I would never,just because of the way we work,
all of that is sort of. Yeah.Icing on the cake versus where membership
is very consistent. I know howmany. We need things like that and
we can maintain the structurethat way. So ads are a big one in

(39:32):
the future for sure.
Yeah, yeah. It's like theopposite of the 80, 80, 20 rule.
I mean your editorial effortgives you 80% of your revenue and
you probably going to spend alot of effort. I mean we have some
salespeople in Philly and Iwill tell you it is a. For the type
of advertisers that make sensefor a newsletter of these sizes and
yours is quite a bit bigger.You know, there's a, there's a level

(39:55):
of education that's required.I would conclude small and medium
sized local or even regionalbusinesses are slower on the uptake
on trends and I think they,their brains break a little on like
the content newsletter. Youknow, they're just kind of coming
around the social and thingslike that and it's like, hey, here's
a newsletter, here's why youshould pay me five grand a month.

(40:16):
And it's a, it's a very hardsell. It's a, you got to get very
creative. We've thought a lotabout partnerships, referrals, but
then there's tracking thosereferrals and there's value to be
had there. I think the servicebusinesses are perfect. The realtors,
the insurance agents, thelawyers where a single customer could
pay for their ad. But again,there's education required.

(40:36):
It's a really good point. Thelocal newsletter space is probably
one of the mostunsophisticated. And I don't mean
unsophisticated as in likepeople are dumb. I mean unsophisticated
in terms of the differenttypes of ads you're doing and media
buying and stuff like that. Sosometimes when I see people posting
online being like, oh yeah,I'm going to do this much revenue
this year. Local ad sales aregoing to totally unlock it. It is

(40:58):
some of the hardest ad salesto do in the business. I would say
based on my experience sellingstuff, because I'm the one selling
the ads, based on mydiscussions with people, based on
just how difficult, likethere's a reason local news is struggling.
Like it's not because they'renot creating an event list and running
it and not selling ads right.It is just difficult. And then you
tack on the newsletter space,which is totally foreign to a lot

(41:21):
of these people, obviously amillion times better in terms of
audience engagement. And onceyou, once you get people in, like
it's pretty clear. But it ishard to sell. And anyone who says
it's, it's maybe they've got areally good team and it's different.
But if you're just startingout, it's a challenge for sure and
good on the people that have,that have figured it out, please
contact me.
Yeah, I mean it woulddefinitely work. I feel like education

(41:45):
is the biggest part and yougot to stay away from CPMs because
CPMs will be outrageously highcompared to what people are used
to. But the results with thegood ad in a highly engaged newsletter,
the results will be also offthe charts. So I think they have
to keep that in mind. And Ihave a little bit of a. You kind

(42:07):
of mentioned people talkingabout how easy it is. Here's the
Playbook. And I don't want topoke anybody here. I have a little
bit of a bone to pick with theway it's been marketed to kind of
startupy type people,entrepreneurial type people online.
I think the growth folks inthe newsletter space and they're
very good and I'm not going toname anybody name because I all think

(42:29):
they're super, I think they'reall super talented and you need growth.
You know, you got to startwith growth. Right? So. And Beehive
is happy to amplify thosepeople. And again, I love Beehive.
I think it's an amazingplatform. There's so much good. But
you know, it is also in theirinterest to get people to sign up
and use the service. Ofcourse, yeah, there's. And again,

(42:51):
it's an excellent service.However, there's a lot of stuff out
there about, hey, here's whatyou do, here's the playbook, here's
how you get to 10, 15, 20,000people. And you know, you're not
the first person I've spokento that has that many people and
we have them as well. And itis, it can be done, but it is hard

(43:11):
and they kind of a lot of themessaging online is it's here's the
playbook. Here's how you getthe people. And now you could charge
$5,000 for ads a month. And Ilistened to Jesse Eisenberg on the
Startup Ideas podcast, and heread Matthew McGarry's kind of like
10, 10 newsletter ideas tostart in 2025. Excellent ideas. And
like it does, it gets thewheels going. And a lot of these

(43:33):
would absolutely work, but itkind of ends with a single bullet
point. Is the here much?Here's how much you could charge
for ads. And you have a$250,000 business and it's like,
no, no, you forget that.
It'S 10 hours a day hustling.
The hardest part, that is sixto 12 months of cultivating the audience
and, you know, not jumping offa bridge because it's not working.
And then you gotta. You gottamonetize it again. Can be done, but

(43:54):
harder. Easier said than done.
I think we've moved into a newworld on the email newsletter space
and even, you know, in themedia space, too. I'd say maybe more
on the newsletter side, wherewe solved the growth problem. The
growth problem is pretty easyto build your audience. Like, the
tools are out there. If youhave any little bit of capital to
invest, you can acquire anaudience. There's. There's people

(44:16):
talking about it, there'speople doing it. It's very easy to
do. The next step is thechallenging part. And I mean, that
is sort of like every fiveyears or seven years, there's like
a new trend where, you know,people are trying to sell something.
And I totally get it. Like,there's great businesses being built
off this. But yes, it is aabsolute slog. And I think the challenge
on the local newsletter side,if we're just focusing on that, is

(44:36):
it's going to take a longtime. Time. The revenue is not going
to be these, you know, forsome of these smaller newsletters
in these smaller cities,you're looking at, like, maybe max,
like 150, $300,000 a year thatyou could probably do if you're just
doing a local newsletter.Like, is that enough for some of
these people and what theywant? I'm not convinced. I think

(44:58):
that it's a slog. Like, ittakes a long time. Like, we've been
doing this for three years andit's only been the last, I would
say six months, where I. WhereI feel very, very confident about
sort of the future of whatwe're doing and stuff like that.
Not that I didn't feel goodabout it before, but we're in that
position now where we can domore. But it. It took a long time.
And so, especially with thelocal newsletter stuff like, you

(45:20):
got to be in it for the longhaul here. Like this sort of quick
churn and burn is not going towork. And frankly, like, it's a great
little life, like you said,great business to be in, of community
connections. And if you'replanning on living in your city forever.
Oh, hell, yeah, I wouldabsolutely start a local newsletter.
It's great. But if you'retrying to become a millionaire off
it, I would not. Unless you'regonna do like a network of local
newsletters and that type ofthing and you're in a city that's

(45:42):
big enough and other piecesthere. It's tough, for sure. No doubt
about it.
Yeah. Yeah. It's almost likethe continuum kind of on one end
is. Yeah, you want to. Ithink, I think Ryan Sneddon in Annapolis,
just seeing him, I think heloves being the Annapolis guy. And
there's probably a path forhim. There's to, you know, I mean,
listen, this is a greatlifestyle. He can maybe pocket half

(46:03):
a million dollars a year inthe long run, consistently own his
audience control. His everyhour in his day is not owned by anybody
else. And he can, I think hesaid it, you know, become the most
popular guy in town. Right.That's a fantastic lifestyle. Right.
I think a lot of people whowere kind of in the kind of Internet
marketing content game, youknow, have grander ambitions or,

(46:25):
you know, they see, hey, Iwant to build the next hustle or
I want to have the next $30million hustle sale or something
like that. And it's like,that's tough with local. Unless you're
piecing it together or you're.You're going vertical. And I do think
there's an opportunity I'vetalked about sporting to if you want
to own a business or really,like, think about the business side,
these things are excellentlead gen. But you are now in another

(46:47):
business which is not sittingbehind your computer. You, you know,
even if you're not operatingthat business, you're still spending
time working on it.
I did not. Yeah. Not to gettoo deep into it, too, but I do think
there is a. Like, a lot ofpeople are entrepreneurs. Like, I'm
an entrepreneur, that type ofthing. Moving from an online business
to running an H VAC businessor running a, you know, one of these

(47:07):
cleaning companies or thingslike that. Like, there's a reason
that, like, small businesspeople are so stressed out and they're
so busy all the time. Like,these are hard businesses, right?
And like, just because yousolve the audience problem doesn't
mean you're going to be ableto solve that other piece. I actually
think the better path in thelong run is just partnering with
someone who has that expertisewhere you're getting a benefit of
that business without havingto, oh, this person didn't show up

(47:30):
at the cleaning place, so Igot to go clean it up. There's an
element there of staying. AndI think this is the problem that
I myself have run into and alot of other people, which is that
you kind of want to doeverything. The sky's the limit.
There's so many things do. Andif there's one thing I've learned,
it's like saying no to certainthings is really valuable. And so
I, you know, I look at some ofthese people that are planning on
launching businesses off theside of their newsletter stuff, and

(47:53):
that's awesome. Like, all thepower to you. But thinking about
the time that it takes to dothis stuff and, you know, it's not
easy and again, it does takework. Right. I think there is a huge
opportunity for that verticalstuff, but thinking about it in a
structured way is reallyimportant. And just to the point
about Ryan too, you know, whenhe first started out, he was talking
a lot about wanting to expandto other cities and things like that.

(48:13):
Right. And I, I actually thinkhe's made the right call, which is
like staying focused on thatone city, maybe doing the consulting
on the side, running your ownbusiness there, like, that's awesome.
Doing, like I will say,expanding to other cities and growing
stuff is, is a real challengeand you have to have processes in
place and things like that.And running a media business is not
easy, but if you can, youknow, add the verticals stuff, absolutely.

(48:34):
He's in a perfect size cityfor it too. And to your point, I
think it's 10 no's for every.Yes is good in lots of things. You
know, you want to try a lot ofthings, but focus usually works.
You know, I was in local mediawith sports for a decade and it literally
took me eight years of alifestyle business before it kind
of turned into somethingscalable. But it was eight years
of content. I mean, literallysix days a week, usually seven, but

(48:58):
you know, sometimes six.Right. And you know, you gotta be
willing to kind of like livein the weeds for a while. Media can
be very good business becausethese are very low overhead businesses.
And you do it long enough andyou build up a good enough audience,
you can get an excellentlifestyle business or you can bolt
something on, you have enoughinfluence to bolt something really
impressive on. And I thinkmaybe we've kind of circled our way

(49:18):
around kind of the two avenuesthat these could go. I think you're
on one side, you're goingsuper premium. We're going to make
people pay, right? Liketraditional media model, we're going
to sell some ads, but we'regoing to rely on supporters and subscriptions
and we're going to be a reallygood media company. And then the
other end of this is a littlebit more surface level, maybe go
a little bit wider events,lifestyle stuff. And, you know, the

(49:40):
content. The thing that's niceabout that is obviously the content
is quite a bit easier. Thoseare the ones that I think are the
most ripe for a business. Notonly to buy a business, but again,
the other way around. Ifsomeone's savvy enough at a business,
they can start one of these.You know, if I am the, you know,
the local lawyer, you know,like a professional, the mortgage
broker, right? You could dothese in three hours a week of work,

(50:03):
right? You can invest $10,000,have 15,000 subscribers, three hours
a week of work. And you just,you know, you just bring them events.
And you don't need to be agreat media business. You just need
every single time to remindthem that, hey, this is brought to
you by your friendlyneighborhood mortgage broker. And,
you know, you'll vacuum up alot of leads that way. And that's
a, you know, I think that'swhere that side of the continuum

(50:26):
may have some success long term.
I think so too. And that'slike the great spot about building
your personality around it tooand infusing it within that. Because
then you become a trustedperson in a scalable way. That's
just impossible with anyother, you know, maybe you run a
TikTok account or somethinglike that locally. But like that
is the true way to sort ofscale yourself and into, you know,

(50:47):
people knowing who you are andleveraging that in other businesses.
So I think if you're goingthat route, that's a great way to
do it. It's just more a matterof managing all of it right and doing
that. But I think, yeah,there's. I'd say that that's a good
way to look at it, the twoways to go about it. I'm going one
way, but I think there's a lotof opportunity that other way. It's
just again, not thinking thatit's going to make You a millionaire

(51:08):
and in one day. Right. It's.It's a, it's a little bit different
than running an Inc. Internetbusiness. For sure. Yeah.
What do you think about. Yougot a couple more minutes?
Yeah, yeah, I got, I got. Ican go for another 30, so. Good.
Okay. What do you think about.I was looking through your LinkedIn.
You've kind of, it seems liketinkered with some other newsletter
types over the last few years.I know you've been in the media space
and the nonprofit space for abit. What do you think about some

(51:31):
of the newsletter space ingeneral? And then niching, you know,
niching down. Like you guyshave kind of niched down into food,
you know, in one way, in bothfrom a general newsletter perspective.
And also can local newslettersniche down even further into local
real estate? I'm bullish onthat. It's a different, different
game you'd be playing. Butwhat do you think about just.

(51:53):
Yeah, I would say thelimitation is not the opportunities.
The limitation is capacity. Ithink the niche down ability of local
newsletters is massive. Foodstuff. We're quickly in Ottawa. We're
quickly becoming the numberone place to find trusted review.
We are the number one place tofind trusted reviews for food in
the city. You know, housingcontent is our most popular content

(52:14):
in the newsletter by far. Not.Not even close. So there's a huge
opportunity around that forus. It's just managing it properly.
I've had opportunities comealong but to do it well and right,
it's really hard. So growingslowly is an important one for us
without taking on, you know,too much. I've seen a lot of places
fail because of that. But theability to niche down I think is
a huge opportunity for localnews because you're already in a

(52:37):
niche down product that are,you know, newsletter that is going
to get huge engagement numbersalready. And if you can find any
ancillary piece that ties intothe local aspect of living in your
city, there's no, there's noreason you can't. You can't focus
on that. So real estate, youknow, maybe some. If you're live
near like a mountain ornature, maybe it's like you know,

(52:58):
a nature newsletter related togoing hiking or skiing or things
like that. Housing stuffobviously even like a sub event newsletter
might make sense. There's alot of different avenues to go. So
I think like the one nicething about local newsletters is
there's no, there's so manydifferent things that you can do.
It's just picking the Right.One that makes sense with what you're

(53:19):
doing. So I see, yeah, hugepotential to niche down. It's more
a matter of like, can youcreate something that people are
going to want to engage with?And it's not, frankly, it's not just
selling something becausethat's not obviously doesn't work.
Funny, I've been big oncommunities and as you're kind of
describing like maybe thelocal hiking club or a fishing club
or something like that. Likeeventually you are so down your community,
like your newsletter mighthave 90 people, but they're 90 people

(53:42):
who show up and go running atthe same place every day. And you
know, now you're, you're not anewsletter, you're a community. You're
sending your community anemail. But it's a, you know, again,
it's of all ends up in thesame space having an engaged group
of people doing something.
And just to that point toolike creating a community too from
nothing. So like for example,our food guy writes a lot about wine
and those like wine reviewsand stuff. And so those are really

(54:02):
popular. So we're thinkingabout spinning out like a wine newsletter
that works with both citiesand all the other cities that we're
operating in. Right. So youcan almost, in some ways you can
almost create your own if youdo it right. You can take topics
that might not necessarilymake sense by itself launching, but
niche down into that becauseyou have the trust of the community.
And you've been pushing thatfrom an editorial strategy. Like

(54:25):
the thinking about youreditorial stuff is really important
because it can drive a lot ofdownstream benefits that you might
not even think about currently.
And you get centralized.That's the big one. And I've kind
of worked on some of thesemodels and we're currently working
on where you can centralize alittle bit of the content which as
you grow horizontally. We haveabout 15 hyperlocal sites and fewer

(54:47):
newsletters in and aroundPhilly. But the one thing that's
relevant to everybody issports in a big sports city. So we
have our sports brand. Well,the sports brand's content gets tentacled
out into all the locals. Nowit doesn't build the whole newsletter
obviously, but it gives ussomething to pull from. And then
all the stuff that surroundsthe central content can always push
towards it and it helps toprop it up to too. And that could

(55:09):
work with wine or frankly anytopic that isn't necessarily geographically
limited.
Totally. Yeah, we've beenthinking a lot about that too. And
one thing we try not to dothough Is we've tried experimenting
with that where it's like, oh,some sort of city building thing
that might apply to allplaces. And sometimes it works, but
then it's also like, is thatgetting too far away from the local

(55:29):
side of stuff? There'sdefinitely ways to do it, but it's
just, you do see a lot oftimes going to these big news sites
where it's like, why is therestuff about the national government
here? When it's just, I wantto know what the traffic is today,
like what we're trying to stayaway from. But a lot of places do
that, so. But there isopportunities for that specific topic
stuff, I think. For sure.

(55:49):
Yeah, yeah. They're grabbingthe AP feed and filling up, filling
up space. A lot of it. A lotof things in media, I find will come
back to needing to fill acertain amount of space in a newspaper
or fill eight minutes of tv.And what's nice about the Internet
is obviously you're outside ofthat paradigm, but so many things
from that paradigm stilltrickle down. If you look at mainstream,

(56:10):
even websites, they're,they're still in that mindset. Well,
we could fill the homepagewith AP stuff about, you know, what
happened in Washington this week.
They need, they need to drivean extra 2,500 page views so they
post an AP thing. Like, Imean, that's the great thing about
newsletters, right? Like, Icould not tell you how many page
views we're getting on ourwebsite right now because I don't
care. Like, it doesn't impactour business at all. Maybe one day

(56:32):
we'll do display ads, butlike, it doesn't matter to us. We
don't, we don't care. We'refocused on that other stuff. And
that is a really nice thingabout having a newsletter based business.
You don't have to worry aboutsome of that ancillary stuff.
Yeah. All right, listen, Iappreciate your time. This was a
really good conversationbecause I think what you guys are
doing is so interesting. It'sdifferent than what a lot of people
are doing. The content isreally good. I love I, again, opinion

(56:56):
is the wrong word and I don'twant to use that. But the context,
the way you guys frame whatcan, what can be. I didn't mean your
content was wonky, by the way,but like wonky local content, the
way you guys frame it andpresent it is in a very modern and
approachable way. And that is,that is a skill and an art to do
that. So I, I think everybodyshould go check out, you know, should

(57:18):
they go Ottawa Lookouts atprobably the best example of what
you guys do.
Ottawalookout.com is the bestway. And I just, you know, for readers,
I think, like, you know,thinking about the stuff that you're
writing in your newsletter,trying to reframe it in a way that's
interesting or different, canjust go a long way to help. Like
you talked about building thatmoat that might sometimes not exist,
but with a personality, withsort of like a unique content structure.

(57:40):
Like, a lot of our stuff is,we're just taking links from other
places and showcasing it, butdoing it in a different way. Right.
So there's an element there ofjust being creative with what you're
doing that can go a long way.
I always like to ask peoplethis, what's one tool that you guys
use in your workflow? Youknow, not a beehive, not an obvious
one, not Google Analytics. Youknow, something like, what's a workflow

(58:03):
thing you guys love to use,can't live without or would recommend
to people?
You know, we probably use alot less tool. Maybe I'll go a different
route and just be contrarianhere and say be careful of trying
to take. Take on too manytools and trying to add too many
things, because if yourorganization's growing, that's just
another thing that everyonehas to learn. I think the mistake
we've made has been trying totack on too many things and it just

(58:25):
can add a lot morecumbersomeness to an organization.
But I'll. I guess I'll closeby saying we use notion a lot. It's.
It's a nice internal wiki formanaging things.
No, that's perfect. That'sperfect. And I agree, you get lots
of logins and then you evercome to sell it, and then somebody's
got to pick up these 17bespoke processes you guys have built
by all your zaps, connectingX, Y and Z. All right, Tell people

(58:49):
where they can find you. Personally.
Yeah, I mean, I don't publishmyself a lot, but jeffsharp on Twitter,
I.
Think Sharp with an E, Sharp with.
An E, Sharp with an E and Jeffwith a G. I think I have a personal
website, but I honestlyhaven't checked in a while. You can
reach me on Twitter, though,or on LinkedIn and if you want to
check out the stuff, ottawa,lookout.com and yeah, feel free to

(59:10):
message me. I'm alwaysinterested in chatting about this
stuff.
Jeff, thanks for your time.
Yeah, thank you.
All right, so that was myinterview with Jeff Sharp of Lookout
Media. So I found a lot there.He is certainly going about this
in a way that is muchdifferent than I think most of the
people building in the Beehiveecosystem, if that's the right way

(59:32):
to phrase it. He is goingsuper deep on news rather than that
sort of digest or lifestyleformat that so many people building
on beehive approach with. AndI think, and I mentioned the show,
this really does kind of helpyou build. I hate to keep using the
word moat but I think it's agood one. It really just helps build
a brand is probably the betterword to use. You know, when you put

(59:54):
out digest style content, youknow, a that could very easily be
disrupted by AI if not now,very soon. But also it doesn't make
you memorable to people. Ifyou think about some of the most,
I want to say successful mediapeople currently or over the last
five to 10 years, some namesthat come to mind and you know, I
mean some people may like loveor hate these people but they're,

(01:00:15):
they're popular and they'vedone well. You look at Dave Portnoy
at Barstool Sports, you lookat Joe Rogan, you look at the all
in podcast, you look at myfirst million. All of these folks
you look at call her daddy andthings like that. All of these folks
have gone about thingsdifferently and they have a very
unique style and tone to theircontent and they stand out. The more

(01:00:39):
you do something that could beeasily co opted by either AI or a
ghostwriter or by somebodyelse and no one would even know the
difference, the less kind of amedia brand that you have. So I think
what they are doing in Ottawaand what frankly what we try to do
at Access, particularly withour brand walking the boards down
in Ocean City is I, you know,I put my face a little bit in that

(01:01:00):
I try to put a spin on some ofthe news stories and sometimes we'll
even give a my take sectionwhich is generally done well as long
as you try not to inflame toomany people. So I think people building
local shouldn't necessarilysteer away from hard news. Yes, it
can actually be more work tocreate and cover hard news because
you have to be a reporter. AndI understand a lot of people kind

(01:01:22):
of building in this spacedon't necessarily want to be reporters
and I get that. However, themore unique information, the more
context, observations, spin,personality and even humor you can
bring to any content product,the better you want to stand out.
You don't need to beridiculous. You don't need to do

(01:01:43):
things that are crazy the way,you know, maybe barstool sports does
and places like that. Butanything to be unique and different
makes you memorable and itmakes you harder to replace. And,
and in the case of Jeff, itmakes people willing to pay for your
content. And that is certainlya business model worth pursuing.
It's probably the hardest oneto crack, but he has hundreds of
thousands of dollars in annualrecurring revenue now, and as long

(01:02:06):
as he's able to make up thechurn, at the very least he's built
a nice lifestyle business forhimself and he has a base to start
from, to grow out from. Great.I really enjoy talking to him, going
about things a different way.And you should definitely check out
all thebrands@lookoutmediaco.com Ottawa
Lookout is their main one.It's really good. Be sure to follow
him. Check him out on Twitterand social media. If you like what

(01:02:29):
you hear from this show, makesure you follow me. I'm Kyle Scott
L All one word on X. You canalso look for me on LinkedIn. You
can type Kyle Scott Laskowskimy full name. I'll come up and then
leave a review and five stars.Make sure you subscribe. Tell your
friends all that fun stuff.Thanks for listening. See you next
week.

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