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Get inspired! Real stories, advice, and revenue numbers from the founders of profitable businesses ⚡ by @csallen and @channingallen at @stripe Get inspired! Real stories, advice, and revenue numbers from the founders of profitable businesses ⚡ by @csallen and @channingallen at @stripe

Transcribed podcasts: 277
Time transcribed: 11d 5h 6m 45s

This graph shows how many times the word ______ has been mentioned throughout the history of the program.

What's up, everybody?
This is Cortland from IndieHackers.com, and you're listening to the IndieHackers podcast.
More people than ever are building cool stuff online and making a ton of money in the process.
And on this show, I talk to these IndieHackers to learn about the trends, the ideas, and
the opportunities they're taking advantage of so the rest of us can do the same.
Today I'm sitting down with the founders of Whereby Us, Chris Sofer and Bruce Pinchbeck.
How's it going, guys?
Good.
And we actually...
One founder is not on here, Rebecca.
She's busy building.
We get to go play, but...
Okay.
So it's three of you, and you built a very cool business.
It's actually two different businesses.
So the first is called The New Tropic.
You started this a few years back, and you've grown it to one and a half million dollars
in annual recurring revenue.
And then around the middle of last year, you decided to spin out another business called
Letterhead, which you've grown to $25,000 a month in revenue.
So a lot of progress here.
Yeah.
The New Tropic was the first thing we started under Whereby Us, and it's a local media brand
in Miami that's focused on helping people get to know the city, find cool ways to engage,
find other people to hang out with, and feel like they're part of the city.
The tagline is, live like you live here.
And we actually have four other brands just like The New Tropic in other cities.
The New Tropic's in Miami, Florida, and then we have brands also in Orlando, Pittsburgh,
Portland, and Seattle.
So that makes up our network of newsletters right now.
And then we just launched in December this new software product called Letterhead that's
helping anyone build and monetize an email newsletter built off of all of the stuff we
learned doing this ourselves and technology we built internally to help us make our newsletters
more profitable and so forth.
I think one thing to note that is interesting about our genesis is we weren't setting out
to make a newsletter product at the start.
I met Chris and Rebecca because Chris was running civic workshops on how to make the
city more interesting, and it's super nerdy, but there were hundreds of people showing
up to these things about transportation and housing and affordability, and he would get
them to kind of workshop ideas.
Rebecca and I joined him on that journey and started learning about human-centered design.
And every single time we hosted one of these meetings in the city, people would pitch ideas
that were about, we need a resource that has all the information of what's happening in
the city.
And we were like, well, that's really hard to do and keep updated and probably not exactly
what we need, but we saw this energy and we're like, let's explore that.
So we spent about a year while we were working full-time doing research and just kind of
understanding habits and behaviors and what people were doing.
And the new topic came out of that and it was this experiment.
We had a year of runway and we had to try to figure out how to monetize it and the landscape
now newsletters are everywhere.
You know, there's like a million groups and tons of resources and everyone's talking about
it.
So it was kind of a wildcard idea.
And I think a lot of people were like, you're doing what you're launching email.
And like, they're like, I don't want email.
And so we kind of build our business from that.
And our revenue kind of came in at a different approach as well.
Whereas a lot of people were focused on membership now at the outset, we were focused more on
can we work with sponsors and advertisers right on a local way?
Yeah.
Newsletters are obviously like the hot new thing.
The last year, everybody knows all about newsletters.
Everybody's starting one.
I'm subscribed to like, I don't know, um, 10 million newsletters at this point.
But your stats are super cool.
I mean, you guys have been doing this for years.
We were talking earlier, you said you got profitable within a year of running a new
Tropic and your latest product letterhead has been doubling in revenue every month since
you started it last April.
Let's talk about local news for a second because I am like the prototypical millennial tech
person.
My last memories of reading the local news were like, or watching the local news were
like probably when I was a kid at my grandmother's house and she lived in this tiny town called
Hendersonville, North Carolina.
So she'd watch like Jeopardy wheel of fortune and then local news and she would just like
shake her head at all the crime or like a tear would form in her eye when somebody rescued
a cat from a tree.
It was very quaint, but it's like, I'm a little, I'm like, I don't, I don't care about local
news.
Why did you guys care?
Uh, percentage of local TV news that stabbings is completely disproportionate to, to how
rampant that problem actually is.
Right.
But it's like, it's all stabbings.
Why is it all stabbings?
All stabbings.
And what's so frustrating is that like people at local TV news stations actually do some
awesome journalism on topics that really matter, but the experience of it as the user is not
that right.
It's this other thing and they'll do consumer investigation and they'll track like our restaurants
following the health code and all these other things.
So they're doing some important work, but then it gets marketed in this way that I think
an opposite effect of what the people working at those places want.
And there are actually studies that people have done like Pew and these other organizations,
like the more local news and particularly TV news you consume, the worse you feel about
the city you live in, which it can't be the case that our goal in helping people like
learn about what's going on in their city is like to make them feel bad about the future
of their city.
So unless you're like a super nihilist in your journalism, which would probably be a
good newsletter.
But anyway, um, I think it's like, how do you change that?
You know, and we heard that a lot from people like I know things are tough.
I don't want people to sugar coat it for me and like only give me the good news cause
that feels saccharine and inauthentic, but help me understand like what we could do or
how things could get better cause otherwise I'm just going to sit in my house and cry
and you know, I could do that for free.
So there's no business there.
Yeah.
It's interesting cause I mean, we've always said if it bleeds, it leads.
That's kind of been like the mantra for media.
And so it's always conflicts, stabbings, robins, disagreements, et cetera.
And you know, not only is that true in local news, but we've also seen that online.
And so the topic to sure, when it comes to social media is that people just tend to share
the most negative, divisive, argumentative stories.
And you know, we're, you know, reportedly all trapped in these filter bubbles, but my
personal experience has been that my filter bubble sort of shields me for that.
I love my filter bubble because I'm not paying attention to random negative news.
I'm just like going on Twitter and following cool people like you and go on an indie hackers
and watch people build cool stuff.
And my filter bubbles, like it's all good things and I'm not sure how possible that
is to do in your space.
Like how much can you really customize and filter local news?
Part of the thing we embraced very early on is that we were not for every single person
in the city.
We knew our user and it was someone that cared about the city enough.
They were invested in it.
They were working on things in the city or, you know, just explore it.
Like the friend who would say, Hey, we're going to go to this new restaurant.
We wanted to make it for that person.
And so we were very, very careful about that.
And I think that helped that we could kind of explore topics based around their needs,
not just the city at large.
And we can also approach explaining topics to those people specifically in that voice
and that tone and not have to try to maybe go too far down that it's not interesting
to someone who knows the basics and also not too far up, but they just get lost in it.
You kind of niche down, you built for a particular customer.
I think a lot of people build apps and products just in general.
They're like, I don't know who this is for, but like, I think it's a cool tool.
So I'm going to build it.
Yeah.
I read this insane CV insights report a couple of years ago, it was about why startups fail.
They do a great job of like tracking this stuff is really interesting.
And a huge percentage of the reason startups fail by self-reporting is like lack of market
need.
And I find that fascinating because it's like, well, how did you even get started if there
wasn't a need for this thing, right?
And then you see people who are totally serving a need that really exists, but they feel this
pressure to make it more generic.
And we tell you, we felt that too, it takes a while to get comfortable, but you feel this
pressure to like, oh, it's for everybody.
Anybody could use this because otherwise my market size is too small or not enough.
And I think it takes a lot of, at least in our case, time and comfort experience to get
comfortable being like it's for this and being okay with that niche because so many people
I think feel this pressure to try and service everybody.
And I think our experience, that's the fastest way to die.
And we've almost died a few times and I think it was always because of that when you boil
it down to that.
So let's go through this, this story.
I want to hear about these near deaths, but maybe let's start at the very beginning.
So you're part of like kind of this civic action group.
People are telling you they want to know more about the city.
They want a resource that just shows them everything that's going on.
And sound particularly realistic because how do you even come up with that resource?
What's the first step you took?
We did an insanely detailed now in hindsight research project about what it was like to
be a local.
And we tried to come at it from the perspective of just learning what it was like to live
in the city without any idea of like, oh, we're going to build a media product or we're
going to build this.
We were just trying to figure out what are people doing?
What do they want help with?
Where are their opportunities to be helpful without an eye toward this is what we want
to make because we didn't want to presuppose or like get confirmation bias.
So we just went out and spent a lot of time with people.
We followed people around on their morning commute.
We went to somebody's house in the morning as they were like getting ready for school
and like watch them put their kid in the car to go to school and like rode in the car with
them as they took their kid to daycare and like followed on their route and went to drinks
with people and just sort of like, we're a weird follow along, you know, attached to
all these people.
Yeah, just watching them.
You probably don't need to go that far, but I was going to say, do you have permission
to do this?
You're just following around random strangers.
Yeah, like lab jackets.
Yeah.
Oh yeah.
We definitely got permission.
So what did you learn by telling all these people?
Because I seem to collecting a ton of information and this is kind of the difficulty of doing
customer research.
It's like you learn a ton of stuff, but like, all right, like, where's the signal and the
noise?
Like, how do you know which thread to follow?
Which information is useless?
We sat in a room for a weekend and put up a couple thousand post-it notes, just every
single thing somebody told us, we put up on the wall as a post-it note and then we tried
to organize them and say like, okay, which things are related to each other?
And so we ended up with stuff about transportation.
We ended up with stuff about food and drink.
We ended up with stuff about taxes and traffic and like all kinds of things that weren't
related.
But then there was a bunch of stuff about information that was related and we got to
email, for example, because there were all these moments where people would roll out
of bed in the morning and check their phone, check their email, you know, I'm standing
on the train and I look at my email, I get into office and I check my email.
Because we had followed and asked people and gotten this research, we saw those little
moments like, okay, that can all tie together.
But it also led us in weird directions.
I mean, our initial business plan had a bar and restaurant in it that we were going to
open.
It was going to be like an underground jazz club.
I think largely because I was obsessed with that idea and Bruce and Rebecca talked me
out of it.
But, you know, it led us in weird directions because we saw people also like, I want a
place to get together and gather with people and we're like, cool, we can run a bar, knowing
nothing about that.
So it led us in some directions that we didn't follow probably for the best also.
We essentially, you know, you get the feedback, we prototyped, we had it on paper and then
we got a lot of feedback and people were like, that is an entirely other business on top
of this other business that you want to do and you should not do that.
And we're like, okay, and I think now we're very glad we didn't, but maybe someday we'll
get to open that bar.
I wrote a blog post actually last year about how to come up with great profitable business
ideas and kind of the central thesis, if you boil the whole thing down is that you want
to start with a problem first and then you want to experiment with different solutions
to that problem.
I think very commonly people pick a solution, they're like, I want to open a bar or I want
to build this type of app and they're just so centered on that solution and it prevents
them from really understanding, okay, who's going to use this?
What's their problem?
And if that's not the right solution, like it doesn't matter now because they're stuck
doing that.
Whereas you guys are like trying all these different zany things because you were more
obsessed with the problem.
You know, how do we help our local community?
And it's obvious that there's like lots of different possibilities for that.
So I like that approach because you can kind of explore different opportunities, pick one
and then exploit that one by doubling down and going really hard on it, which for you
guys it seemed to be that newsletters were really caught on and seemed to be the thing.
Yeah, we got advice from one of our early investors who said, when you're trying to
solve a problem that you don't necessarily know the answer to or that there hasn't been
a ton of experimentation around, which at the time local news totally fell in that bucket,
you got to be willing to try everything once.
And when you do that thing once, you're like, do we like doing this?
Is it profitable?
How's it going?
And we embraced that, which also led us to doing things that I don't know if we ever
thought we would do.
We opened a little event space where our offices were and Bruce had to scrub the toilets.
We had rats.
Turmites also.
We ran an event series, you know, all kinds of weird event series, some of which were
great, some of which were horrendous.
We organized press releases and we did press conferences that we organized for one customer
and it went horribly wrong and we did a terrible job.
Like there's just all kinds of stuff like that, we'll try it once and, you know, and
then Bruce would come back and be like, this sucks.
Like we cannot do this again.
Don't do that to me again.
Yeah.
When you started the newsletter, did you think of it as local news?
Cause none of this other stuff, it doesn't seem like local news.
It's like events, you know, it's community type stuff, but local news is a very specific
thing and it has existed for many decades, centuries really.
And the last, I guess, couple of decades, it hasn't really done very well.
It's not the most inspiring line of business to get into you.
I think it's a hard for us to necessarily jump into like the news machine and say, we're
going to publish this much stuff and we're going to cover all these topics and we're
going to have all these layers of, of editing.
We just didn't have that scale.
And so it was like, what, where can we fit in this ecosystem?
And I think at first when we launched a lot of local news, we're like, who are these new
players they're encroaching on our territory.
And quickly they realized, Hey, we actually are driving traffic to your site and we're
complimentary to you and we want to push people to understand your stories better.
I think that kind of attention eased a bit and we found our place is just kind of, I
think the word we use a lot now is community, which is probably overused, but it's really
just about, you know, how are you serving this group of people, these users?
And that comes across obviously in the product we're making now, but you know, we weren't
sitting at city hall meetings and trying to get the breaking story.
It was more of like, let's just help people navigate the city.
Oh man.
You got to tell me about these other newspapers who were looking at you as a threat and we're
talking shit about you.
Weirdly, journalists, despite being in the publication business are actually pretty good
at much more subtle shade than that.
So it enters the rumor mill and you got to hear things in the back room or out for drinks
or Hey, so-and-so said such-and-such, there's a lot of that going on.
I think, you know, pre no tea, no shade, but it was very much that kind of moment where
you would hear a lot of stuff in the back channel that way.
But I think as Bruce is saying, it became evident really quickly to people that the
mentality was just different and that there didn't have to be a scarcity mindset, which
I think exists in a lot of these, particularly if I'm independent creators and smaller folks,
like it's really easy to get sucked into scarcity and particularly when there's big players
in town, in our case, like a newspaper, well, it's already a newspaper.
So like, what are we going to do?
But the reality I think in most of these areas is that there's actually room for a lot more
of those instances and they actually kind of help each other out.
I used to do research on young people, media stuff, and there was this through line of
like, oh, all these young people are getting their news from the daily show and not reading
the actual news.
This was like a thing in like, you know, the mid aughts or whatever.
And the research showed like that wasn't the case at all, that most people who watch the
daily show also read other news and that if you watch the daily show, you're actually
more likely to start reading additional news because it would feed you back into the loop.
And so we saw the same thing at the local level.
And we would get people coming and saying, I just went to the county commission meeting
for the first time in my life to talk about X, Y, Z issue because I read about it in the
new tropic.
Or I just found my business partner or started a new nonprofit with somebody that I met through
the Evergray in Seattle, like these kinds of stories.
And obviously we track quantitative metrics, but we also try to help our team track qualitative
stuff around these community wins where you're helping somebody connect to the city or giving
them these moments because that's ultimately the output that we care about, not how much
coverage are we doing or, you know, whatever.
There are other organizations that do a great job of that.
So I think part of it was just getting comfortable in our own skin.
And it totally took us a while because we spent the first two years every time something
came up, spending time thinking about that, thinking about the competition instead of
staying focused on our user.
And I think when you get to that point of like, I am here for these people, I make this
for them.
And it almost doesn't matter what other people are doing.
When you get to that point of comfort, I feel like the world totally shifts, at least it
did for us.
So I want to talk about you guys have obviously expanded this to multiple cities, you've multiple
local news organizations.
Obviously, you've learned a lot probably from the similarities and differences.
But I want to talk about just like zooming in on like your very first local newsletter,
the mechanics of how that worked.
So maybe the best way to do this is to compare you with like another story.
Are you familiar with Andrew Wilkinson who runs tiny?
Yeah.
Yeah.
So he's been tweeting about this for maybe the last couple years about how he's always
been a fan of the news.
He's always read like these big news organizations, but like his local paper sucked.
Because unfortunately, local newspapers have just been getting out competed by the internet,
and they've lost a lot of their budget, and they can't really afford to hire like great
investigative journalists, etc.
And so he's a rich guy who's thinking about like, what can I do?
You know, maybe I can buy the local newspaper for like $10 million and you know, improve
it and shape in the way I want it to be shaped.
But instead, he just kind of started his own new thing.
And so I think his playbook to start with was that he hired a journalist for about 60
grand, and was like, all right, you're gonna do investigative journalism, you're gonna put
out some articles, etc.
And then he spent maybe $200,000 on just like a ton of Facebook ads, where really there
wasn't much competition, like the other local newspapers weren't buying Facebook ads.
And over time, he's able to grow into I think the publication with the largest audience
share and his city, which is huge, because I believe he lives in Victoria, Canada.
So it's kind of a cool story.
I mean, he's profitable.
He doesn't have a lot of the traditional fixed costs, like he doesn't actually print a newspaper,
you know, he's not like doesn't have like a newsroom where or a big building where everybody's
you know, send down writing the news, basically, a MailChimp newsletter, a Webflow website,
a journalist and some Facebook ads.
And that's pretty much it.
It kind of feels like this is something anybody could do in their own city.
But I'd be curious to see how the story compares to how you guys got started with the new tropic
in Miami.
There's a lot of similarities.
I think one of the things Andrew did that was really smart was laser focus, right, reporter,
email newsletter, advertising to get people on the email newsletter.
We were much more promiscuous with what we were attempting.
We tried everything once, and we really did try that, right?
Like we ran events, we did like a painting event called Arts and Drafts that Bruce came
up with.
We did, I mean, all kinds of stuff.
And I think a lot of that was like, okay, we're trying to build community here and make
it feel stickier and deeper than just interacting with a piece of media content.
And in some ways, I still feel like, yeah, that was the right mentality, because we wanted
stickiness.
We wanted stick around, feel an affinity for the brand.
We wanted that sense of like, I belong to this.
And when all you do is interact with an email, that can be harder to build.
On the other hand, we were wildly inefficient in comparison to something like what Andrew's
done, right?
Because we were trying all these other things.
And so I think there's benefits to both of those paths.
But this is the risk, I think, of starting with the problem.
We were so interested in the problem that when the solution presented itself, we were
almost slower to get to this is the focus solution, because we were still iterating
and going out and looking for other ways to solve the problem, probably beyond the point
where we should have said, Oh, shit, this is the solution.
Let's double down on this one.
And so we probably got to a little slower than we should have.
Now six years down the road, I think we're way smarter for having done that.
Because we know all these things that don't work.
It's like we've dated enough people to know what we don't like.
And so now we can be more confident, you know, in our relationship, like it's that situation.
This idea of focus has been running through my mind a lot since I talked to this guy,
Evan Britton, who runs his website, Famous Birthdays.
And it's this huge website, it gets like two billion page views a year.
And it's just like hyper crazy focus.
He's at all these different like lanes, he could go down, he could do news, he could
do like interactivity and create user accounts.
But like, he's like, No, for nine years, I'm just doing the exact same thing over and over
and over again.
And it's hard to say he's wrong, because he's getting billions of page views a year and
it's working.
And you look at other websites like Twitter, people are constantly like, why isn't Twitter
added this or added that?
Why don't they do this?
They're so dumb.
Like they never change it.
And it's like, well, Twitter's also used by like hundreds of millions of people, like
maybe there's something to this like hyper focus, maybe we all think that we can do more
things than we really can.
And even when you have hundreds or thousands of engineers like Twitter, you probably still
can only really do one thing really well.
Yeah, I think that mails it.
I mean, while we stumbled a little bit in the beginning, it did kind of allow us to
then keep blinders on as more competition came on, because we would see kind of those
repeated mistakes we had made in the past in little slivers or two, okay, well, we know
that that's not going to work too well, or they're about to hit a roadblock.
I think that pivoting a little bit to where I'm at now our mindset is how do we help others
avoid those landmines along the way when they're building their thing?
Yes, let's dive into that a little bit.
I'm gonna get the brass tacks on your newsletter.
Who was writing these stories?
What did the newsletter look like?
Who is subscribing?
And how are you how are you finding these people?
This is a great segue from famous birthdays, because I think it's a good example just like
Twitter of it's really hard to scale or grow something while also adding new columns, like
it's really hard to do breadth and depth at the same time, right?
And we learned that really quickly.
So when it started, Bruce was doing all of our events and organizing all the community
related stuff and doing a lot of the marketing.
Our co founder, Rebecca was leading all the editorial content and the actual production
of the newsletter and so forth.
I did a little bit of writing, but mostly was doing sales, sales work of advertising
and things like that.
And it worked pretty well because we had all the bases covered.
But I also think as another example where we were spread, you know, into multiple categories
really early.
And so we learned a lot about sales, for example, like how do we sell this thing to advertisers
and sponsors?
We learned that really fast.
But what would happen if all three of us had been working on making the newsletter and
that content really excellent in those early, you know, how much more that's triple the
firepower, how much farther would you have gone, you know, instead of dividing your forces
at that really, really early stage.
And that's something I think we we learned when we went and did the second market.
And we went to Seattle with these two awesome people, Monica and Anika, who were thinking
about launching their own thing.
They were already on that journey.
And we got introduced to them and said, Hey, wait, these folks are really smart.
They have an awesome idea.
They know their community really well.
And we've got a model for how to do this.
So let's help give them structure and like take care of the payroll and the website and
all the stuff that sucks and so that they can focus on the stuff that they're good at,
which is the community and the content.
And they got to focus in over those first months on building the community, understanding
the users, getting the content exactly right, understanding who they were for.
And they grew that initial a couple of month period, they grew like 10 times faster than
our thing did, because they had that focus, I think they're also way smarter than we are.
So that helps.
But they were able to like hone in on that, like, okay, we're just doing this.
And then once it had reached that certain point, now it had some traction, then they
could go out and sell it and so forth.
But I think I mean, it's really hard to do that, except in hindsight, but that was one
thing we totally learned is that you cannot replicate it and grow it and experiment with
new stuff at the same and learn a new skill all at the same time, unless you're superhuman.
So this is almost like podcast network model, where you know, maybe there's a parent company
who gets together a bunch of podcasters, and they share knowledge and resources and help
with ads.
You're doing the same thing for newsletters, it was called a new Tropic in Miami.
What's it called in Seattle?
Because I'd love to subscribe to this.
I actually live in Seattle at the moment.
The Evergray.
The Evergray.
Cool.
Sounds like the right way to describe the weather in Seattle.
Honestly, that was a thing we even struggled with and had to experiment with is like, is
the new Tropic the wrong name?
Should it be whereby us Miami whereby us Seattle and we thought that localized brand name is
authentic.
It is of the city, you know, it has that character to it.
And I think that matters a lot, especially in the Pacific Northwest, where they can smell,
you know, an imposter from a mile away.
It wasn't just, hey, this Miami company is coming in and telling you about your city.
It's, you know, we're hoping to provide structure to local writers.
So you find these two women in Seattle who already kind of want to do their own local
newsletter.
What is the knowledge that you impart?
Like, what are some of the specific things that you tell them to help them get started?
A lot of it was about the process of getting to know the market and branding it and getting
that initial stuff out of the way that I think was the first value.
The part where you go from there's something here.
People in this community would be interested in something.
There's energy here.
I could make something that would be useful to.
This is exactly what it is and what the structure is and what we're going to call it and how
it's going to feel.
That part is like the impossible journey through the woods where everybody gets lost, right?
Because it's like, you could guess wrong and you know, it's the whole thing we're talking
about before about niche.
So that was the first part.
Is there like a playbook for that?
Yeah, we built this whole little deck of how to do research in a local community and do
the creepy follow along research that we did in Miami.
It really wasn't that creepy.
We asked for permission, but we built that deck of like how to do this.
And then we built some air table templates that where you filled in all the findings
and sort of assembled everything.
And then this little Google slides presentation where you would kind of capture what you learned.
So we turned it into like this process that could be implemented.
And now we're starting to consider doing that in like other topics other than local, but
we built it for this idea of like, how do you understand, capture and respond to a city
in this short, like two week research sprint and then come out two to four weeks later
with like a brand and a thing.
And then we knew here's the product.
Here's the website template, all of that.
So we sort of had all of that and that sort of saved them hopefully six months or whatever
of work they would have done on their own sort of getting started.
And then we had all the like operational payroll admin kind of infrastructure and the sales
infrastructure.
So those are really the things that we brought to the table and they knew the city and they
did the content.
The thing about that research process that was really, really awesome too is not just
figuring out your community is we have topics to cover.
We knew what people were interested in because we'd cluster and say the trans, it's a big
thing.
Okay.
We know that's got to be a topic also in the newsletter.
But then the other fun thing was we had super users right from the beginning.
You know, we'd spend an hour or two with folks interviewing them with the human centered
approach and just listening.
And these people were invested in the product at that point.
They wanted updates.
They wanted to subscribe.
They were the first people we sent these newsletters to.
I think, you know, intentionally making sure we got lots of different perspectives that
opened us up to a lot of communities and I would definitely advise folks if they're creating
more newsletters is to go out, do that research and help and stay in touch with those people
you talk to.
They're going to be your first users.
Yeah.
I wonder how much people can do this digitally and not just locally.
So like locally, you have obviously a community in a city like Miami or Seattle or Pittsburgh
or wherever you guys are.
You can go just talk to real people like let's talk to someone who owns a deli shop.
Let's talk to someone who works on transit.
Let's talk to people in government.
But online you also have communities.
You have Andy hackers community.
You have little sort of implicit communities on Twitter.
You have communities like Hacker News.
You have communities on Reddit and I imagine these probably work the same way and there
might be like an unexplored opportunity here where people could like bootstrap a newsletter
or some sort of publication targeted specifically at just one community and they hit it from
every angle.
They get the news and people who are part of that community get subscribed to that newsletter
and it's way easier than going to like, you know, whatever website and having to comb
through like a thousand posts and try to find the signal and the noise.
I feel like you could probably just unbundle Reddit and make newsletter communities for
each little community that has, you know, over a thousand members like you could probably
pop something up pretty quick and get some interest or also know that that idea was bad
and you can move on.
Like myself personally, I sometimes I get latched into an idea and until I test it,
it just stays there.
And so it's like, can I just prototype and like learn?
So I think that's a great thing.
So let's talk about two different things.
One I want to talk about growth because for the vast majority of founders and the hackers
in particular who don't have a lot of resources, they're always wondering like, how do I grow?
Like I'm doing this thing and I might even be doing a good job.
Like if you build that, they will come as not necessarily true for lots of different
types of projects.
The other thing I want to talk about is just process.
You know, you've got this playbook, obviously it's a little bit different for every different
city, but I kind of want you to spill a little bit of your secrets here.
You know, like what is the same, how do you structure and write news or a newsletter and
a way that works across any city?
I think one of the things we've learned is that you only get truly to do one or two things
in your work with regular originality.
It's the whole thing with Pixar and Creativity Inc and you know, the structure that underlies
the creative process allows you to be creative in the thing you're actually making.
And so if you're like being creative about like how you're paying your bills or how you
order pens to the office, like you're probably not, your actual product is going to suck
because you're spending all your energy like being creative about that.
And that's something that, you know, I certainly strongly, I'm not a process person, but our
co-founder Rebecca is very much process oriented.
And I think we've been able to get that mentality right over time, which is like if all these
other things are predictable and fixed and totally uninteresting, then the creativity
can go into the actual content.
So pretty much everything about our newsletters is standardized in terms of what goes into
them, what kind of expectations and metrics we set, how we estimate our sales goals, how
we think about our membership program.
All of this stuff is the same at a foundational level across markets so that our local editors
who are really running these brands and working like sort of the many CEOs of these brands,
they can apply their creativity to the content, the city, the voice, and like what's local
to the market.
So that's the way we think about it is like fixed foundation that is the same everywhere.
And then we can build a cool house on top of it because you know that the foundation
is solid and somebody's done the work to make sure it's going to be sturdy.
We did a medium post, a couple of medium posts actually a couple of years ago about the research
process we use in these cities and things like that.
So we've made a lot of that open and put templates up on Google drive and stuff like that.
Yeah.
I guess just like from the outside looking in probably some of the standardized things
might be like what topics you're writing about or what kinds of articles you write about.
So there might be like, we're going to always going to do editorial, we're always going
to have a crime section, we're always going to have like local business stories, we're
always going to have XYZ, maybe business model.
So we're always going to be advertiser sponsored and here's where the ads are going to go in
our newsletters.
And we're always going to have like, you know, a membership paid section for people who really
want the extra scoop.
Talk to me about some of these things, you know, like specifically like how do your newsletters
make money and how do you even structure the news?
This plays into why we built Letterhead too in a big way, which is you want to have as
many revenue tools at your disposal as you can.
I think it's the rare creator, the rare media business that gets to say like, we're only
doing X because you need a lot of tools in order to make things work in a tough environment.
And so we do advertising that is listings and really simple self-service ads where anyone
can buy an ad in our newsletters.
We do custom native content that we work on with sponsors over many months and really
build a thoughtful longer term campaign with them.
We do memberships we used to do before COVID events.
So we do all kinds of different tools to make the revenue as diverse as possible and to
sort of combine the reliability of recurring reader subscriptions with the opportunity
to really grow and get extra fuel from larger advertising deals and so forth.
So the first principle is like, let's put all of that on the table and try to mix those
things together in a way that works.
So we have as many tools at our disposal as we can.
That's a big part of it.
And then the second piece is just really focusing on the community engagement and monetizing
that.
So we try really hard to resist the pull of as many impressions as possible or how do
we get as many page views as we can or whatever.
We try to keep everything.
The conversation with advertisers, the way we track our metrics aligned to how many engaged
people are there who are part of this community who seem to care about enough to regularly
participate in it.
That is ultimately the thing that matters, is the thing that advertisers care about.
It's so easy to chase shiny objects.
I'm the chief offender of that in our company.
It is so easy to be like, oh, here's this cool thing we could also do that someone says
they want.
And it's so easy to just like, oh, yeah, let's go do that, right?
But if you know what the thing is, you're really prized at the top, you're like looking
at it every week, I think it's way easier to resist that temptation.
And I think when you asked a question about like, I had like flashbacks or like PTSD of
like, where does it go in the newsletter and stuff, is I think for a while we struggled
with that.
It was like, oh, there's a new thing.
We want to do a new, like Chris's thing, shiny object.
We're trying a new format.
Where does it go?
And we would have, you know, a whole meeting and workshop and where do we want this to
go?
How's it going to be?
And so it's like before we got to the process and before we did all the experimentation,
it was painful.
But I think we finally land to a place now that it's like, we don't have to make that
decision.
It's about the creative, which has been big.
And I think when we also started, like, again, I have more of an artist background, which
is, you know, fluff, but it was like, oh, let's not constrain people.
Let's like, say you can create the newsletter.
And really that made things worse.
The writers struggle because it's like, that's stressful.
You know, you're dealing with like hard hitting news and I have to distill this.
And now I have to figure out what to write every day on deadline.
It was super, super painful.
So I think this would be advice to any other creator out there, especially in content is
like, just stay to that formula.
You can repeat because then you can get really creative about the subjects and how you play
within that box.
And that's where you get to shine.
Yeah.
When I started Indie Hackers, I had kind of the same thing where I would watch all these
other people with newsletters and blogs, just be like, from my perspective, endlessly creative
every week.
I'm like, that looks exhausting.
I don't have to figure out a new thing to write about every week.
Like what if I just had like one very specific structured interview format and I don't have
to think about that at all.
You know, the variety will come from the different people that I interview who are going to be
very different answers, but it's not going to come from me having to exhaust all this,
you know, burn all these calories being creative every week.
So that worked really well for me.
And it seems like it's kind of the same approach you guys took.
Does that mean the solution is just like creative laziness is really the secret to success here?
You have to be creative, but you also have to be lazy enough to be like, I don't want
to do all that work every week.
I'm going to make some documentation.
It's like upfront creativity.
You put in the creative work upfront, but then you put it on an assembly line so that
later on and sort of like reproduce that creativity easily.
And then whenever you feel a burst of inspiration, like you create like another assembly line,
like another type of content or another structure or format that you can sort of figure out
and hone and then eventually become sort of mindless and really easy to do.
Yeah.
I mean, I think there's a lot of people who resist that content factory notion because
it's been done wrong so many times, but I think that has more to do with your point,
like the upfront creativity, like what are you making and is authenticity built into
it?
And is it compelling to people or is it just random clickbait articles of what celebrities
look like 50 years ago?
It's like it starts at the front end, right?
But we resist the process when really we should be resisting content that people don't care
about or whatever.
Right.
And that's a really interesting idea.
Yeah.
I'm starting a new show with a buddy of mine.
He's been on this podcast before and we spent probably like a month or two just thinking
about the show.
Like who do we want to have on the show?
What's the point?
Who's it for?
What's it going to be like?
What's the format?
And just thinking about the stuff upfront can get you much closer to the target that
you want to arrive at.
Like you start to make tweaks later.
You're never going to get it right all upfront, but it's just better to plan upfront, I think
if you can.
And a lot of people don't do this because they have a lot of trouble getting started
in the first place.
And if they do this kind of stuff, they're just going to fall prey to analysis process
and never get started.
But I think, you know, if you're the kind of person who's self motivated and you're
like, you've a bias towards action, like you guys didn't really seem to have a lot of problem
with motivation.
You just got started.
And if you can do that, then it's worth planning upfront.
Well, I will say I appreciate the compliment, but it's been a lot of work to get to that
point.
And I think we still are like very carefully slide back into those habits and we hold each
other accountable.
That's for sure.
Yeah, that's one of the huge benefits to having co-founders is you just have the built in
accountability buddies.
And it's easy to underestimate how tough it is to stay motivated as a solo founder and
also just focused because the fewer people you have, if you're just one person, that
means you have to be even more ruthless about what you're going to say no to and the things
you're not going to do.
Let's talk about growth and then we'll move on to letterhead.
How did you grow your subscriber base with a new Tropic?
And when you move into these new cities and work with new authors, how are you helping
them grow their subscriber basis?
Because getting like people to actually care about your newsletter and to grow to the point
where advertisers care, it's not easy to do.
Well, I'll tell you, it's something that is an ongoing learning process for us where
this past year in 2020, we actually didn't see as much like top of funnel growth of like
to the free readership base of our newsletters because we put so much energy into growing
our paid subscriber base, growing our advertising products, pivoting some of our content because
of COVID and everything else going on in the world.
And those things paid off for us business wise, right?
We come out of the year with a profitable business and really good profit margins and
a lot of improvement over the last year.
But I think even in our size, we're an example of you can't do everything well without tons
of money and we've never invested much money at all in paid acquisition of readers, partly
because we just haven't wanted to dedicate our resources to that.
And partly because we didn't want to become reliant on it as the growth method.
I remember listening to a podcast way back when we were starting his interview with a
venture investor and they're saying, whenever I see a company where the vast majority of
their growth in users, particularly if the core product is free, is coming out of paid,
I do like a double check.
I want to look under the hood more deeply because that tells me like maybe there's some
astroturfing going on.
Sometimes it works, but sometimes it means that, hey, we're just paying our way through
to this thing and there's not actually a business under here.
And that kind of stuck with us to say like, okay, if we can grow organically, for the
most part, even if it's slower, it's going to be stickier.
And we did some testing to try and figure out if that was true.
So we did this analysis of like, when a reader comes on to our newsletters, are they more
likely to stay engaged and click and open stuff and refer us to their friends based
on where they, what source they came from, which is of course, super common in like business
intelligence world, but from like smaller writers and publications is often impossible
to do that level of data analysis.
And we fortunately had some people on our team who had that experience and we were able
to build a little dashboards for it and all that.
And what we found really clearly was like, when people come in organically, a friend
refers them, you know, they discover it through piece of content that they care about.
They're way more likely to be engaged than someone that we paid to acquire.
And when you add up the value of that over anything longer than like six months, it's
just way more valuable to grow organically than to pay for it in our business.
And so we just always shied away from that paid growth and focused on organic.
And it means you grow a little slower, but it means the engagement is higher.
And if you've done the niche focus work really well that we talked about before, then you
can still have a good profitable business that way.
So I think we have found really clearly like you don't have to have a ton of money for
paid acquisition to do this.
If you can get the organic thing right and get the engagement out of it, even with a
thousand or 5,000 readers or whatever, you know, you can have a meaningful business.
And now that's like commonplace kind of notion with all these new tools that have come along.
But even in local news, like we've been able to sort of show like, okay, this can work.
You just have to be willing to not boil the ocean and have something that is compelling
enough for people to stick to.
And I think the thing that we were able to get over early on was the idea that at media
you have to have the most people in the largest audience to get the advertisers.
And so we had to very early on tell the story of these are who these people are and here's
how engaged they are.
And here's the events they're going to.
And that helped us secure early investors too.
And so I think if you have that organic growth and this really deep community, it's so much
easier to go into a sponsorship conversation and say, like, these are the people you want.
And they are like very invested in this type of topic.
So I think that's a big one for people.
I follow Austin reef on Twitter.
He's the founder of the morning brew, one of the co-founders and morning brews is huge
newsletter that's grown to, I think a couple million, maybe two or 3 million subscribers.
And he's got this pen tweet at the top of his profile, where he talks about kind of
a thread of threads.
And each one of the threads explains one part of how they were able to grow morning brew.
So he's got one unpaid acquisition and he's got one on the early days.
Now they found their very first users.
And now he talks about how they would actually go to college campuses and they would go to
professors and ask if they could do presentations in front of their students.
And then they would pass around a clipboard and ask everybody to write down their email
address so they could take those email addresses home and like manually subscribe them to the
morning brew because they didn't trust that if they told people their website that they
would actually follow through and do it.
So I'm curious how you guys approach this in the early days.
You know, if you imagine that you were some solo founder trying to start a newsletter
and get your first 100, 200 subscribers, what would your approach be for that?
We don't know a single newsletter creator, I will say, like we know a lot of people making
newsletters now.
Like I don't know that I think a single one whose journey at some point didn't involve
a piece of paper with like manual sign up and then going home later and like trying
to read with their piece of paper because their handwriting is terrible.
I think everybody has that story for that reason.
I don't know, Bruce, I mean, I feel like you're the one with all the fun creative thoughts
about this.
Well, if you're saying 100 to 200, I think the first thing is the people you know in
this space or like friends and family is the most obvious.
Like get people in there and start getting critique.
The other thing I think is big in that initial phase is we really embraced like what we say
our value was embrace the beta, meaning like things are rough.
We're learning.
We're going to be really transparent.
And I think the thing you're talking about too with these Twitter threads that are like
transparent is people love to just see vulnerability and be a part of it and have a conversation.
So that was a big thing for us too.
And so those first 10 that you get ask them for personal help and just say, hey, if you
know anyone that might be possibly interested, it's free.
I could really use the help and like you can get to that fairly quickly.
And I think that vulnerability also takes some of the edge off the sales enos of like
sign up for my thing.
It's like I really care about this community and here's what I'm trying to build.
And I would appreciate if you would check it out.
That would be my like easiest, lowest hanging fruit thing to do.
And then beyond that referral tool technology has grown a lot.
They build our own initially, but readers will send us onto friends because one, they
want their friend to know about it, but two, it's also kind of like a badge.
It's like a little moment of like, check out this thing I read this.
This is kind of my part of my identity is supporting this group and I want you to know
about it.
And so I think if you have some ability to do that as well, that can help tremendously.
I think that applies to the business side too, where somebody gave me the advice, like
go to the people who are never going to invest in your company first, but the customers who
are never going to actually hire you first and get feedback on your thing so that you
don't burn that learning on people who are actually like valid customer targets or advertisers
or investors.
And that was really good advice.
I wish I remember who told me that, but we went out and did it and we talked to some
friends who did investing and people who invested in other kinds of companies.
And we talked to advertisers who were like way too big for us or totally not a fit or
not located in Miami and gave them our decks and gave them our sales pitch thing like tear
this apart if you don't mind.
And that was so useful even when we were early because we sort of got it out of the system.
So by the time we took it to somebody more legit who was actually a lead or a target
or a potential investor, we had gone through that first phase of like shaking out the parts
that were broken and it felt a lot more polished.
People underestimate how helpful other people on the internet will be if you're actually
legitimately working on stuff.
So if you've got nothing going on and you're just like, hey, I've got some ideas I'm noodling
on and I haven't really started yet and I've got nothing really to my name, people are
going to be like, don't bother me.
But if you actually started working on something that you probably run into some roadblocks
and you could message somebody else who's working on that thing and like give them like
specific information about what you're working on, what you're stuck on, ask them specifics
about what they're working on.
And it's just way easier for people to help them.
Don't ask to pick your brain.
No picking brains, please.
Yeah, don't be vague.
Respect people's time.
Don't ask them to meet for no discernible reason.
Don't ask them to meet just because you want something from them.
Like they've got other things to do.
You know, I do this for any hackers actually.
I'll spend a lot of time researching and reading things just so I sort of know what's going
on in the community.
And then when somebody's name comes up, I'll think, oh, this is really interesting for
reasons XYZ and I'll message them and I'll say something about their product.
I'll offer an idea or something and try to get them on the phone and pretty much everybody
says yes to that because like who's going to say no to somebody who can like potentially
help you with what you're working on messaging with ideas and tips.
So I think that's just a great way to learn in general.
If you read blog posts, you're going to get like something that was written three years
ago for a general audience.
If you get somebody on the phone, you're going to get like a highly motivated, engaged person
who can respond to exactly what you're saying, who knows about your situation, who's going
to give you much better information than you could find probably written anywhere.
I might regret this.
I'll say that anyone listening, if you want to talk about, let's say newsletters and what
you're working on, holler at me, like send me a note, drop me a thing on Twitter.
I love helping people workshop that stuff.
But as long as it's specific, it's like I'm working on this thing and I'm curious about
the next step.
If it's about, you know, generally I can send you links, you know, articles to awesome stuff
that are resources, but yeah, I think, I think specific problems are also fun.
It's a fun break from the work for other experts too, just to be like, yeah, like let's geek
out on this one topic for a minute.
Typically you just, you don't expect anything from it other than a great conversation and
maybe insight to a new perspective.
And I'm the business guy.
So I guess my job would be like, this also applies to the business side.
But I think this specificity also is super useful for sales and, and things like that,
because there are all these people who will sell like advertising or software or sponsorships
in their outreach email or Twitter DM or whatever is like, Hey, would love to chat.
But it's actually like, I want to sell you something, but I don't say that on the cover.
So much more effective to just say like, Hey, here's what's up.
Like I have this thing.
I think it would actually be really cool for you.
Are you interested?
Because if they're not interested, you better find out fast, like save yourself some time.
Don't bury the lead.
If somebody emails me or deems me and they're like trying to like hide what they're going
to ask.
Like not only am I probably not going to say yes to the thing in the first place, but like
now I'm suspicious.
Like, why are you hiding this thing for me?
Like, why don't you just tell me what it is?
You know, don't DM me and ask me if you can ask me a question, like just ask the question.
Let's talk about letterhead.
You guys have a, you haven't quite pivoted.
You're still doing the new tropic.
You're still growing in cities across America.
So making millions of revenue from that.
But now you've got this new SAS tool that you're building.
You started on last year.
It's kind of this perfect playbook where you start a company and in the course of running
that company, you come up with new ideas and new products and then you realize other people
could probably use that as well.
So what is letterhead and why'd you start it?
Well, in a sentence or two, letterhead is a tool for helping anybody build and grow
and launch a newsletter business.
We talk about it like Shopify for newsletters on shorthand that it would be our wildest
dreams of course.
But the idea is how do you help somebody publish a newsletter, build great content, monetize
it through advertising and through memberships and be able to do all of that in one container.
Earlier I said, hey, we have a lot of different revenue channels.
We do advertising.
We have big ads and native campaigns and small ads and memberships, all these different pieces.
Another challenge if you're a small team or even a big team, but if you're a small team
or an individual is like, sure, that sounds nice, but how am I going to possibly juggle
all those balls at once?
It's impossible.
And so letterhead is designed to bring all of that into one place where it's modular.
You can use the parts of it you want, not use the parts you don't need, but it's all
in one place.
You can actually manage all of that in an efficient way and cut out most of the time
involved in doing that stuff well, which is not writing the content, but actually making
the data talk to each other, getting the advertisement place, getting the metrics back to the advertiser,
getting the subscription data to talk to your email list.
All of these things are where people waste so much time and there's so much frustration.
So we started from the place of how do we cut all of that out so that it's possible
to build businesses like ours with way less overhead, way faster, and with an eye toward
the business always, because most of these email tools that are out there are focused
on marketing rather than on newsletters as the core product.
Right. And who's like your ideal customer? Like, of course, like Substack exists. A lot
of people are using Substack, mostly like individual newsletter creators who just want
to get the word out and Substack kind of helps them, gives them the writing tools and a website
and the community and a newsletter and like some payment stuff. How do you guys see yourself
in alignment with tools like Substack and Ghost and Mailchimp, etc?
Yeah, we see Substack as an awesome tool for individual writers and for folks who are starting
out and for people who are membership only, right? Like, I only want to do subscriptions.
What we see happening is that as a lot of these businesses grow and they start to have
more revenue channels and become more multifaceted businesses and for teams and publishing brands
and other kinds of organizations that are not individual writers or small teams of writers,
there's a need for the newsletter to talk to the rest of the business and for there
to be advertising and subscription and for these things to integrate with other tools.
Those are the kind of needs of a business, operating newsletter business, whether you
are a small team or some other kind of organization and those business needs are the ones we're
interested in solving. So we talk about letterhead as a set of business tools, right, rather
than a writing platform or something like that because there are already some awesome
solutions for that and we hear from people who are kind of graduating from Substack quite
a bit recently and we talk to people who are wanting to start a newsletter and we send
them to Substack because they describe their needs and we're like, there's actually an
awesome tool for this already. So we see it kind of like that and we see a lot of folks
coming to us from platforms like MailChimp where they're using MailChimp for their lists
and sending and for their marketing email but they want to do an email newsletter where
there's an actual content product and it's really hard to use a tool like MailChimp for
that. It's just not designed for it and so that's why we actually integrate with ESPs
like MailChimp. So you can stay with MailChimp and use letterhead on top of it to do your
newsletter and your advertising and your subscriptions.
I think early on we're seeing early adoption from folks who have a newsletter and they
are thinking of advertisements but they're kind of hacking together solutions. There's
like submit your type form and we'll email you back and forth and they're seeing the
breakdown in that process and want to offload that and they're using letterhead to help
manage the storefront, take payments, get creative, approve the creative and then insert
it into the newsletter without going into spreadsheets because we had that same challenge.
Yeah. When I first started IndieHackers, I had sponsors and I put them on the website,
the podcast and the newsletter and the newsletter is pretty annoying because it was very visual,
kind of like the website. People, you'd have to go back and forth over the copy. I didn't
have a place for people to come kind of sign up and upload their stuff so I had a million
emails. People were sending me like, oh, use this image. Wait a minute. Use this image,
et cetera, et cetera and I was probably spending half my time just on the advertising side.
It's fun when you make a sale. It's not fun when you're dealing with all the other bullshit.
It's fun to make the money until that high settles down. You're like, oh, I have to go
write the newsletter now. Exactly. Oh, that other sponsor didn't send me an ad that I
need. Yeah, exactly. Exactly. You got to track all the stats, et cetera. It seems like a
super cool tool. You've grown it already to 25,000 a month in revenue, which is really
fast growth for a SaaS company. A lot of people with like info products and paid newsletters
and communities and courses and they're usually quite able to get up to high revenue numbers
quite quickly, but people with SaaS tools, it's usually kind of a slow burn. It's a lot
of research. People aren't paying that much to begin with. What do you attribute the month
over month doubling of your growth to and being able to hit 25K a month in revenue and
under a year? Part of it is we started with a solution to a problem that we find is really
common and tried to deliberately make it easy to say yes to because one of the things we
ran into as publishers ourselves is there's an infinitely expanding universe of tools
for so many things. And I certainly have shiny object problem of like, Hey, here's a cool
new tool I could use, but you have to switch and migrate and train everybody. And it can
be really difficult to adopt those things. So even if there is a better way of doing
it, it becomes hard to use. So one of the things we built in from the beginning was
this works with your MailChimp. You can keep your existing email service provider. You
can keep your existing workflow. This sits on top and helps with your existing work.
You don't have to just like buy everything we do and do this complete migration. It's
not Salesforce where you have to spend 12 years adopting it and this complicated thing.
So we tried to be really deliberate about that. I think that helped us. And then the
other piece is that we're not just generating revenue from subscriptions to the software
itself, but we also are doing a lot of shared advertising sales, helping sell advertising
placements across the different newsletters that are using Letterhead. And it's still
early days there. We're still learning a lot how to do that. But we've talked to over the
last six months a lot of different kinds of advertisers that want to reach different audiences.
They have big audience numbers they want to hit, but they want to reach engaged actual
human beings in a direct way. And they like newsletters as a channel for that. So we're
helping them do that across the different newsletters that are using Letterhead. And
that's a big percentage of our revenue as well. So having both of those revenue tools
that are disposable has also helped us grow really quickly.
I love that because when you think about a SAS tool, I mean, it's a programmer's like
wet dream, like, I'm just going to code this thing. And it's just going to be a money tree
that I'm going to be rich or whatever. But if you think about the problems that people
have, a lot of them are like kind of service-based problems or like, they don't know how to grow
their newsletter or they don't know how to find advertisers. And sometimes those are
the most important problems, you know, getting more users, more readers and more advertisers.
So if you kind of just ignore that and try to do nothing but the mechanical, you're kind
of leaving a big business opportunity on the ground. And you know, this idea of like a
passive income generating SAS tool, although it's attractive, is usually a pipe dream.
Most of the people I know working on SAS tools are still working every day, like everybody
working on services. So I like the idea that you're combining the two, you know, like there
are, for example, megaphone and podcast hosting, you know, they'll host your podcast, but they'll
also like programmatically insert ads into your show when you don't have an ad that you
found. And it's like, okay, well, they're doing this cool service for you in addition
to hosting. So like, why wouldn't you use that? Or with Andy hackers, like we're sort
of building an almost sub-stat clone for people who want to start newsletters. And like you
guys, like ours is compatible. So a lot of our early series authors have sub-stacks.
We're like, Oh yeah, keep your sub-stack, but also write for any hackers. And what we'll
help you with is distribution. We'll put you in front of the Andy hackers audience and
get you a lot of users. And like, that's very service space for us. But like they love that
because sub-stack isn't helping with that. So it's super cool that you actually help
your early customers with advertising rather than just like, here's a tool, it'll help
you write and help you publish. But it's, that's it, you know, it's nothing but a robot.
And that's all you get.
Bruce has been doing a lot of this, like just doing a ton of content marketing and working
on how can we get guides and helpful tips and templates out to folks who are, who are
using letterheads. That's something that we're hoping to do a lot more of too, is just, here's
some guides and templates. Here's what other people are doing that's working. Because there's
so much of that, that's like, there's a lot of advice out there that's generic, but getting
from zero to doing that is the hardest part. So how do we give people little ways to get
started?
The thing I'm trying to learn right now, and I would love again, like send me your questions
about newsletters, but also I'm curious, like, what are people actually going to ingest?
These are busy people. They're, they're hacking away. It might be at the side hustle. It might
be the full-time job, but I'm like, you know, if I make a tutorial webinar video, you know,
this whole course, will that actually be the most useful tool to these creators in the
moment when it's like, I just need to answer how to grow. What am I going to do right now
to grow today? While I have to write this thing or, you know, work on a membership call
to action, that's currently the journey I'm on, is trying to understand where to meet
people at. And then my last thing is Cortland, we should definitely figure out what's going
on with this indie hackers newsletter and figure something out.
Wink, wink.
Yeah, maybe we should be collaborating.
No, the one thing I wanted to add to the end of that is like, I see in this, in the newsletter
community, the immediate thing is membership, which makes a ton of sense. So I have users
sign up to membership, get me some MRR and you know, and build that. We came from it
completely opposite, which I'm not saying is right, but what it did is gave us a lot
of fundamentals and like, how do we sell ads, sponsorships and things like that. And membership
was like almost an afterthought for a while. It was just like, we have this thing. If you
want to be a member, great. We have special content and events and discounts. And since
the pandemic, we've right sized that and you know, go to your audience and kind of open
like, Hey, we need support. And it's been helpful for us as well to just understand
that how you can play those two things to build more revenue. Like if you have a strong
membership base now and let's say maybe free readers on top of that, there is a lot of
opportunity in opening up sponsorships. If you can do it the right way to not distract
from that other core experience. And so that's what I'm like, I'm getting anxious. I see
these groups out there and like, man, these people are doing such good things. And if
they're interested in it, but they haven't done it because of this whole, it's too much
work. You know, could we help serve them and could they hire more writers? Could they expand
to new new markets? Like that's going to be the thing that gets exciting for me.
I mean, I love this whole area because Andy hackers, I mean, we talked about this before
the call, the whole point of the show and the website is to inspire more people to get
started. It's kind of like the very top of the funnel of entrepreneurship. Everybody
was on the fence of like, can I start an online business or should I keep working at my nine
to five? And the easier it becomes to start an online business, the more people who do
it. And so the fact that like, there are these multiple methods of basically getting online,
learning some stuff and then sharing your knowledge with others and actually building
a profitable business for yourself on top of that is super cool.
And the fact that you guys and other people like you are building tools to make it easier
for people to do this, just feeds into the cycle. We're just going to see more and more
people write newsletters, selling courses, launching eBooks, building websites that
are informative, etc. And like, that's kind of like the first stepping stone and to being
financially independent Andy hacker. So I love what you guys are doing. We're about
out of time here. So I want to wrap up and just ask each of you based on your journey
the last five or six years, what's your advice for a fledgling Andy hacker who's just getting
started and maybe they don't know what they're going to work on and maybe they just took
the very first steps. What do you think they can learn from what you two have learned?
I would say that the best thing you can do is a deep understanding of the community you're
trying to reach the audience who you're trying to sell to or build with. I think too often
we make assumptions based on our own perspectives and that's super dangerous. And you're going
to spend a lot of time that you have limited amount of energy and resources. I would say
attempts before you start to just give up and say, Oh, I'm not that kind of person.
I can't do this sort of thing. So take that time to slow down and think and do the research
and have conversations, read and Twitter in Twitter sphere that you're not a part of and
start to really understand it. But that would be my thing. Do a little bit of that research,
take a pause.
I love it. So just to summarize, start by understanding your customers, your community.
You know, you really only get a limited number of attempts to try to figure out what people
want. And so you can cut down on the number of attempts required by really focusing on
people. And I love that because it's kind of fun. You know, when you sit down, you start
coding and building. It's very lonely and isolating and there's a lot of stress because
you're not sure if people want it. But if you start by doing nothing but like, you know,
having calls with people and reading what they're saying and talking to them and like
you guys said, following them around the city, like that stuff is just kind of very fun and
energizing. So I love that you start that way. And then second point, break your giant
journey down into a lot of bite sized steps because it's not going to be like you just
go from zero to a million in a day. You know, it's going to be a long windy process. And
if you sort of chart a course and plan ahead, going to be in for fewer surprises and it's
going to be easier to make decisions and switch directions along the way. So Chris, Bruce,
thanks a ton for coming on the show. A lot of good advice, great story, some good chatter
about local news. Thanks for coming on.
Thanks so much, Corla. Appreciate it.
Can you let listeners know or they can go to, to not ask if they can pick your brains,
but to find out what you're doing and ask very specific questions about newsletters
and content and whatever else might be on their minds.
Well, first you could check out Letterhead. It's a try letterhead.com. You'll see a little
bit of what we're working on there. And obviously we have a contact form if you want to kind
of talk deeper about that. But personally, you can send me a note at bruce at whereby.us
W H E R E B Y dot us. That's my email or follow me on Twitter, Bruce pinch pick listeners.
If you enjoyed this episode and you want an easy way to support the podcast, you should
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pretty much all the reviews you leave over there. Thank you so much for listening. And
as always, I will see you next time.