Making $1.5M/Year Reimagining Local News with Chris and Bruce of WhereBy.Us

Courtland Allen: 0s

What's up, everybody? This is Courtland from Indiehackers.com and you're listening to the Indie Hackers 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 indie hackers 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 Sopher and Bruce Pinchbeck. How’s it going, guys?

Bruce Pinchbeck: 30s

Good. Actually, one founder is not on here. Rebecca, she's busy building. We get to go play, but…

Courtland Allen: 37s

So, it's three of you and you built a very cool business. It's actually two different businesses.

The first is called The New Tropic. You started this a few years back and you've grown it to $1.5 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 of revenue. So, a lot of progress here.

Chris Sopher: 59s

Yeah, The New Tropic was the first thing we started under Whereby.us. Its'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.

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. That makes up our network of newsletters right now.

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.

Bruce Pinchbeck: 1m 44s

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. 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.

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. 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. The New Tropic 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.

The landscape now, newsletters are everywhere. There's like a million groups and tons of resources and everyone's talking about it. But at the time it was kind of a wild card idea. I think a lot of people were like, “You're doing what you're launching email? I don't want an email.” So we kind of built our business from that and our revenue 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 on a local way?

Courtland Allen: 3m 11s

Yeah. Newsletters are obviously the hot new thing in the last year. Everybody knows all about newsletters. Everybody's starting one. I'm subscribed to I don't know, umpteen million newsletters at this point, but your stats are super cool.

You guys have been doing this for years. We were talking earlier, you said you got profitable within a year of running The 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, or like, or watching the local news where like probably when I was a kid at my grandmother's house and she lived in this tiny town called Hendersonville, North Carolina, you know? So, she’d watch “Jeopardy,” “Wheel of Fortune,” and then local news. She would just shake her head at all the crime. Or 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 millennial. Idon't care about local news. Why does you guys care?

Chris Sopher: 4m 1s

Percentage of local TV news, stabbings is completely disproportionate to how rampant that problem actually is, right?

Courtland Allen: 4m 10s

It's all stabbings. Why is it all stabbings?

Chris Sopher: 4m 14s

What's so frustrating is that 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. They'll do consumer investigation and they'll track are 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 is opposite the effect of what the people working at those places want.

There are actually studies that people have done, Pew and these other organizations, the more local news, 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 learn about what's going on with their city is like to make them feel bad about the future of their city. Unless you're a super nihilist in your journalism, which would probably be a good newsletter.

But anyway, I think it's like, how do you change that? We heard that a lot from people., I know things are tough. I don't want people to sugar coat it for me and only give me the good news because that feels saccharin and inauthentic, but help me understand what we could do or how things could get better, because otherwise I'm just going to sit in my house and cry and you know, I can do that for free. So, there's no business there.

Courtland Allen: 5m 19s

Yeah, it's interesting. Cause we've always said if it bleeds, it leads, that's kind of been like the mantra for media. It's always conflict, stabbings, robbings, disagreements, et cetera. Not only is that true in local news, but we've also seen that online.

Topic de jour, when it comes to social media, is that people just tend to share the most negative divisive, argumentative stories. We're reportedly all trapped in these filter bubble, 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 going on Twitter and following cool people like you and go on Indie Hackers and watch people build cool stuff. My filter bubble’s all good things and I'm not sure how possible that is to do in your space. How much can you really customize and filter local news?

Bruce Pinchbeck: 6m 4s

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 just explore. Like the friend who would say, “Hey, we're going to go to this new restaurant.”

We wanted to make it for that person. We were very, very careful about that. I think that helped that we could kind of explore topics based around their needs, not just the city at large. We could also approach explaining topics to those people specifically in that voice, in 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 out that they just get lost in it.

Courtland Allen: 6m 43s

You kind of niched 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 I think it's a cool tool, so I'm gonna build it.”

Chris Sopher: 6m 51s

Yeah. I read it this insane CB Insights report a couple of years ago, it was about why startups fail. They do a great job of like tracking this stuff. It's really interesting.

A huge percentage of the reason startups fail by self-reporting is lack of market need. I find that fascinating because it's how did you even get started if there wasn't a need for this thing, right? Then you see people who are totally serving a need that really exists, but they feel this pressure to make it more generic.

We told 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. Cause otherwise my market size is too small or not enough.” 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.

I think in 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.

Courtland Allen: 7m 49s

So let's go through this story. I want to hear about these near deaths, but let's start at the very beginning.

You're part 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. It doesn't sound particularly realistic cause they can't even come up with that resource. What's the first step you took?

Chris Sopher: 8m 7s

We did an insanely detailed, now in hindsight, research project about what it was like to be a local. 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. Cause we didn't want to presuppose or get confirmation bias.

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 getting ready for school and watch them put their kid in the car to go to school and rode in the car with them as they took their kid to daycare and followed on their route and went to drinks with people and just sort of like, we're a weird follow along, attached to all these people.

Bruce Pinchbeck: 8m 55s

Yeah. Just watching them. You probably don't need to go that far, but…

Courtland Allen: 8m 59s

I was gonna to say, did you have permission to do this or were just following around random strangers?

Bruce Pinchbeck: 9m 2s

Yeah. Like lab jackets on.

Chris Sopher: 9m 4s

Oh yeah. We definitely got permission.

Courtland Allen: 9m 6s

So what did you learn by tailling all these people? Because I assume you're collecting a ton of information. This is kind of the difficulty of doing customer research. It's you learn a ton of stuff, but where's the signal in the noise? How do you know which thread to follow? Which information is useless?

Chris Sopher: 9m 19s

We sat in a room for a weekend and put up a couple of thousand post-it notes. Just every single thing somebody told us, we put up on the walls, a post-it note, and then we tried to organize them and say like, “okay, which things are related to each other.”

So we ended up with stuff about transportation. We ended up talking about food and drink. We ended up with stuff about taxes and traffic, all kinds of things that weren't related. But then there was a bunch of stuff about information that was related.

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 and check their email. 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.

It also let 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 an underground jazz club, I think, largely because I was obsessed with that idea. Bruce and Rebecca talked me out of it, but 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.

Bruce Pinchbeck: 10m 28s

We essentially 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.

Courtland Allen: 10m 44s

I wrote a blog post actually last year about how to come up with great profitable businesses. Kind of the central thesis, if you boil the whole thing down, is that you want to start with the 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. It prevents them from really understanding, okay, who's going to use this, what's their problem. If that's not the right solution, it doesn't matter now because they're stuck doing that.

Whereas you guys are trying all these different zany things because you were more obsessed with the problem how do we help our local community? It's obvious that there's 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.

Chris Sopher: 11m 31s

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 not there hasn't been a ton of experimentation around, which at the time, local news totally fell in that bucket, you gotta be willing to try everything once.

When you do that thing, once you're like, do we like doing this? Is it profitable? How's it going? We embrace that, which also led us to doing things that I don't know that 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.

Bruce Pinchbeck: 12m 2s

Termites, also.

Chris Sopher: 12m 3s

We ran an event series, all kinds of weird events 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. There's just all kinds of stuff like that.

We'll try it once and then Bruce would come back and be like, this sucks. We cannot do this again.

Bruce Pinchbeck: 12m 24s

Don't do that to me again, yeah.

Courtland Allen: 12m 25s

When you started the newsletter, did you think of it as local news, because none of this other stuff, it doesn't seem like local news. It's events, it's community type stuff, but local news is a very specific thing and it has existed for many decades, centuries, really. 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.

Bruce Pinchbeck: 12m 44s

I think it's hard for us to necessarily jump into 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 gonna have all these layers of, of editing.

We just didn't have that scale. So, it was like, what, where can we fit in this ecosystem? I think at first, when we launched a lot of local news where like, who are these new players, they're encroaching on our territory. 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 tension 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, 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.

Courtland Allen: 13m 34s

Oh, man. You gotta to tell me about these other newspapers who were looking at you as a threat and were talking shit about you.

Chris Sopher: 13m 38s

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 get 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 or you would hear a lot of stuff in the back channel that way.

But I think as Bruce was 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 independent creators and smaller folks, it’s really easy to get sucked into scarcity. Particularly when there's big players in town, in our case, a newspaper, well, there's already a newspaper, 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 oh, all these young people are getting their news from “The Daily Show” and not reading the actual news. This was a thing in the mid aughts or whatever. The research showed that wasn't the case at all, that most people who watch “The Daily Show” also read other news. f you watch “The Daily Show,” you're actually more likely to start reading additional news because it would feed you back into the loop.

We saw the same thing at the local level. 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 XYZ issue, because I'd 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 Evergrey in Seattle, these kinds of stories.

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 whatever. There are other organizations that do a great job of that.

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.

I think when you get to that point of I am here for these people, I make this for them, 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.

Courtland Allen: 15m 59s

I want to talk about, you guys have obviously expanded this to multiple cities. You have multiple local news organizations. Obviously, you've learned a lot, probably from the similarities and differences, but I wanna talk about just zooming in on your very first local newsletter, the mechanics of how that worked.

Maybe the best way to do this is to compare you with another story. Are you familiar with Andrew Wilkinson who runs Tiny?

Chris Sopher: 16m 19s

Yeah.

Courtland Allen: 16m 19s

He's been tweeting about this for maybe the last couple of years, about how he's always been a fan of the news. He's always read these big news organizations, but his local papers 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 great investigative journalists, et cetera.

He's a rich guy, he was thinking about like, what can I do? Maybe I can buy the local newspaper for $10 million and improve it and shape it the way I want it to be shaped. Instead, he just kind of started his own new thing.

I think his playbook to start with was that he hired a journalist for about 60 grand. It was like, all right, you're going to do investigative journalism. You're going to put out some articles, et cetera. Then he spent maybe $200,000 on just a ton of Facebook ads where really there wasn't much competition, the other local newspapers weren't buying Facebook ads.

Over time he was able to grow into, I think the publication with the largest audience share in his city, which is huge because I believe he lives in Victoria, Canada. It's kind of a cool story. I mean, he's profitable. He doesn't have a lot of the traditional fixed costs. He doesn't actually print a newspaper. He doesn't have a newsroom where, or a big building where everybody's sitting down writing in the news. Basically a MailChimp newsletter, a Webflow website, a journalist, and some Facebook ads.

That's pretty much, it kind of feels like this is something anybody could do in their own city, but I'd be curious to see how this story compares to how you guys got started with The New Tropic in Miami.

Chris Sopher: 17m 43s

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. We really did try that, right? We ran events. We did a painting event called arts and drafts that Bruce came up with. We did, I mean, all kinds of stuff.

I think a lot of that was like, we're trying to build community here and make it feel stickier and deeper than just interacting with a piece of media content. In some ways, I still feel like, yeah, that was the right mentality because we wanted stickiness. We wanted people to stick around and feel an affinity for the brand. We wanted that sense of like, I belong to this.

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. Because we were trying all these other things.

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.

We probably got to that 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 could be more confident in our relationship. It's that situation.

Courtland Allen: 19m 20s

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. It's this huge, website. It gets like 2 billion page views a year.

It's just hyper crazy focus. He’s got all these different lanes it could go down, it could do news. He could do interactivity and create user accounts. But he's like, no for nine years, I'm just doing the exact same thing over and over and over again. It's hard to say he's wrong because he's getting billions of page views a year and it's working.

You look at other websites like Twitter, people are constantly like, why isn't Twitter out of this or out of that? Why don't they do this? They're so dumb. They never changed it. And it's like, well, Twitter is also used by hundreds of millions of people. Maybe there's something to this hyper-focus. Maybe we all think that we can do more things than we really can. Even when you have hundreds or thousands of engineers like Twitter, you probably still can only really do one thing really well.

Bruce Pinchbeck: 20m 6s

Yeah. I think that nails it. 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 would say, 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.

Courtland Allen: 20m 30s

Let’s dive into that a little bit. I'm going to get the brass tax on your newsletter. Who was writing these stories? What did the newsletter look like? Who is subscribing and how are you finding these people?

Chris Sopher: 20m 37s

This is a great segue from Famous Birthdays, because I think it's a good example, just like Twitter, where it's really hard to scale or grow something while also adding new columns. It's really hard to do breadth and depth at the same time. We learned that really quickly.

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 work of advertising and things like that.

It worked pretty well because we had all the bases covered, but I also think it was another example where we were spread into multiple categories really early. We learned a lot about sales, for example, 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 in that content really excellent? That's triple the firepower. How much farther would you have gone instead of dividing your forces at that really, really early stage?

That's something I think we learned when we went and did the second market. 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 take care of the payroll and website and all the stuff that sucks so that they can focus on the stuff that they're good at, which is the community and the content.

They got to focus in over those first months on building the community, understanding users, getting the content exactly right, understanding who they were for. 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 hoan in on that and be like, okay, we're just doing this.

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 it's really hard to do that except in hindsight. That was one thing we totally learned is that you cannot replicate it and grow it and experiment with new stuff at the scene and learn a new skill all at the same time, unless you're superhuman.

Courtland Allen: 22m 50s

So this is almost like podcast network model where 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’s called The NewTropic in Miami, what's it called in Seattle? Cause I'd love to subscribe to this. I actually live in Seattle at the moment.

Chris Sopher: 23m 6s

The Evergrey.

Courtland Allen: 23m 6s

The Evergrey. Cool. It sounds like the right way to describe the weather in Seattle.

Bruce Pinchbeck: 23m 9s

Honestly, that was one 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?

We thought that localized brand name is authentic. It is of the city, it has that character to it. I think that matters a lot, especially in the Pacific Northwest where they can smell an impostor from a mile away. It wasn't just, Hey, this Miami company is coming in and telling you about your city. Now, we're hoping to provide structure to local writers.

Courtland Allen: 23m 37s

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? What are some of the specific things that you tell them to help them get started?

Chris Sopher: 23m 47s

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, too, 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 the impossible journey through the woods where everybody gets lost. You could guess wrong. It’s the whole thing we were talking about before about niche. So that was the first part.

Courtland Allen: 24m 18s

Is there like a playbook for that?

Chris Sopher: 24m 19s

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 wasn't that creepy. We asked for permission.

We built that deck of how to do this. Then we built some Airtable templates that where you filled in all the findings and sort of assembled everything. Then this little Google slides presentation, where you would kind of capture what you learned. We turned it into like this process that could be implemented.

Now we're starting to consider doing that in topics other than local, but we built it for this idea of, how do you understand, capture, and respond to a city in this short, two-week research sprint, and then come out two to four weeks later with a brand and the thing. Then we knew here's the product, here's the website template, all of that.

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 getting started. Then we had all that operational payroll, admin kind of infrastructure and the sales infrastructure. Those were really the things that we brought to the table and they knew the city and they did the content.

Bruce Pinchbeck: 25m 23s

The thing about that research process that was really, really awesome, too, was not just figuring out your community, is we had topics to cover. We knew what people were interested in because we'd cluster and say the transit's a big thing. We know that's gotta be a topic also in the newsletter. The other fun thing was we had was super users right from the beginning. We'd spend an hour or two with folks interviewing them with the human-centered approach and just listening.

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 a lots of different perspectives that opened us up to a lot of communities. I would definitely advise folks if they're creating more newsletters is to go out and do that research and help and stay in touch with those people you've talked to. They're going to be your first users.

Courtland Allen: 26m 6s

I wonder how much people can do this digitally and not just locally. 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 the Indie Hackers community. You have little sort of implicit communities on Twitter. You have communities like Hacker News. You have communities on Reddit. I imagine these probably work the same way.

There might be an unexplored opportunity here where people could bootstrap a newsletter or some sort of publication targeted specifically at just one community. They hit it from every angle. They get the news and people who were part of that community get subscribed to that newsletter. It's way easier than going to whatever website and having to comb through a thousand posts and try to find the signal in the noise.

Bruce Pinchbeck: 26m 53s

I feel like you could probably just unbundle Reddit and make newsletter communities for each little community that has 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. Myself personally, I sometimes get latched onto an idea. Until I test it, it just stays there. So, it's like, can I just prototype and learn? I think that's a great thing.

Courtland Allen: 27m 13s

Let's talk about two different things. One, I want to talk about growth because for the vast majority of founders, indie hackers in particular, who don't have a lot of resources, they're always wondering, how do I grow? I'm doing this thing and I might even be doing a good job. If you build it, they will come is not necessarily true for lots of different types of projects.

The other thing I want to talk about is just process. You've got this playbook, obviously it's a little bit different for every different city, but I kinda want you to spill a little bit of your secrets here. What is the same? How do you structure and write news? Or a newsletter in a way that works across any city?

Chris Sopher: 27m 44s

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. This is the whole thing with Pixar and Creativity, Inc. The structure that underlies the creative process allows you to be creative and the thing you're actually making.

If you're being creative about how you're paying your bills or how you order pens to the office, your actual product is going to suck because you're spending all your energy being creative about that. That's something that I certainly struggled with. I'm not a process person, but our co-founder Rebecca is very much process oriented.

I think we've been able to get that mentality right over time, which is, if all of these other things are predictable and fixed and totally uninteresting, then the creativity can go into the actual content. Pretty much everything about our newsletters is standardized in terms of what goes into them, the 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 mini-CEOs of these brands can apply their creativity to the content, the city, the voice, and what's local to the market.

That's the way we think about it as fixed foundation that is the same everywhere. Then we can build a cool house on top of it because you know that the foundation is solid and somebody has 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. We've made a lot of that open and put templates up on Google drive and stuff like that.

Courtland Allen: 29m 17s

If I had to guess from the outside looking in, probably some of the standardized things might be what topics you're writing about or what kinds of articles you write about.

So, there might be we're going to always going to do editorial. We're always going to have a crime section. We're always going to have 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. We're always going to have a membership paid section for people who really want the extra scoop.

Talk to me about some of these things. Specifically, how do your newsletters make money and how do you even structure the news?

Chris Sopher: 29m 47s

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 or the rare media business that gets to say we're only doing X. You need a lot of tools in order to make things work in a tough environment.

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. We do have 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.

The first principle is 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. Then the second piece is just really focusing on the community engagement and monetizing that. 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, but it's so easy to chase shiny objects.

I'm the chief offender of that in our company. It is so easy to like, Oh, here's this cool thing we could also do that. Someone says that they want, and it's so easy to just like, Oh yeah, let's go do that. But if you know what the thing is that you really prize at the top and you're like looking at it every week, I think it's way easier to resist that temptation.

Bruce Pinchbeck: 31m 32s

I think when you asked the question about I had PTSD of where does it go in the newsletter and stuff. I think for a while we struggled with that. It was like, Oh, there's a new thing. We want to do a new, Chris’s thing, shiny object, we're trying a new format. Where does it go?

We would have a whole meeting and workshop and where do we want this to go? How's it going to be? And so it's before we got to the process and before we did all the experimentation, it was painful. But I think we’ve finally landed to a place now that it's we don't have to make that decision. It's about the creative, which has been big.

I have more of an artist background, which is fluff, but it was like, Oh, let's not constrain people. Let's say you can create the newsletter and really that made things worse. The writers struggle cause it's stressful. You know, you're dealing with 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.

I think this would be advice to any other creator out there, especially if in content is just stay to that formula you can repeat. Then you can get really creative about the subjects and how you play within that box. That's where you get to shine.

Courtland Allen: 32m 30s

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, from my perspective, endlessly, creative every week.

I'm like, that looks exhausting. I don't want to have to figure out a new thing to write about every week. What if I just had one very specific structured interview format? 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 give me very different answers, but it's not going to come from me having to exhaust all this, burn all these calories, being creative every week.

That worked really well for me. It seems like it's kind of the same approach you guys took.

Chris Sopher: 32m 59s

Does that mean the solution is just creative laziness is really the secret to this success? 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.

Courtland Allen: 33m 11s

It's 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 reproduce that creativity easily. Then whenever you feel a burst of inspiration, you create another assembly line, another type of content or another structure or format that you can sort of figure out and hone, and then eventually it becomes sort of mindless and really easy to do.

Chris Sopher: 33m 31s

Yeah. I think there's a lot of people who resist that content factory notion because it's been done wrong so many times. I think that has more to do with, to your point, the upfront creativity, what are you making and is authenticity built into it? Is it compelling to people or is it just random clickbait articles of what celebrities looked like 50 years ago?

It starts at the front end. But we resist the process when really we should be resisting content that people don't care about or whatever. That's a really interesting idea.

Courtland Allen: 33m 59s

Yeah, I'm starting a new show with a buddy of mine. He's been on this podcast before and we spent probably a month or two, just thinking about the show, who do we want to have on the show? What's the point? Who's it for? Why does it exist? What's it going to be like, what's the format?

Just thinking about the stuff upfront can get you much closer to the target that you want to arrive at. You still have 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.

A lot of people don't do this because they have a lot of trouble getting started in the first place. If they do this kind of stuff, they're just gonna fall prey to analysis paralysis and never get started. But I think, if you're the kind of person who's self motivated and you have a bias towards action, like you guys didn't really seem to have a lot of problem with motivation. You just got started. If you can do that, then it's worth planning upfront.

Bruce Pinchbeck: 34m 39s

Well, I will say I appreciate the compliment, but it's been a lot of work to get to that point. I think we still very carefully slide back into those habits and we hold each other accountable that's for sure.

Courtland Allen: 34m 50s

Yeah. That's one of the huge benefits to having co-founders is you just have, they're 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. The fewer people you have, 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 The New Tropic? And when you move into these new cities and work with new authors, how are you helping them grow their subscriber basis? Cause getting people to actually care about your newsletter and to grow to the point where advertisers care is not easy to do.

Chris Sopher: 35m 24s

Well, I'll tell you it's something that is an ongoing learning process for us. This past year in 2020, we actually didn't see as much top of funnel growth of 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.

Those things paid off for us business-wise. 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 at 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, it was an interview with a venture investor. 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 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 it's not actually a business under here.

That kind of stuck with us to say, okay, if we can grow organically, for the most part, even if it's slower, it's going to be stickier. We did some testing to try and figure out if that was true. We did this analysis of when a reader comes 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 business intelligence world, but from smaller writers and publications is often impossible to do that level of data analysis.

We fortunately have people on our team who had that experience and we were able to build a little dashboard for it and all that. What we found really clearly was when people come in organically, a friend refers them, they discover it through a piece of content that they care about, they're way more likely to be engaged than someone that we paid to acquire.

When you add up the value of that over anything longer than six months, it's just way more valuable to grow organically than to pay for it in our business. So, we just always shied away from that paid growth and focused on organic.

It means you grow a little slower, but it means the engagement is higher. 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, 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 can have a meaningful business. Now that's a commonplace kind of notion with all these new tools that have come along. But even in local news, we've been able to sort of show 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 it.

Bruce Pinchbeck: 38m 18s

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 and the largest audience to get the advertisers. 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.

I think if you have that organic growth in this really deep community, it's so much easier to go into a sponsorship conversation and say these are the people you want and they are like very invested in this type of topic. I think that's a big one for people.

Courtland Allen: 38m 48s

I follow Austin Rief on Twitter. He's the founder of the Morning Brew, one of the co-founders. Morning Brew is a huge newsletter that's grown to, I think, a couple million, maybe two or 3 million subscribers.

He's got this pinned tweet at the top of his profile where he talks about kind of a thread of threads. Each one of the threads explains one part of how they were able to grow morning brew. He's got one on paid acquisition and he's got one on the early days an how they found their very first users.

In that one 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. 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 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.

I'm curious how you guys approached this in the early days. 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?

Chris Sopher: 39m 47s

We don't know a single newsletter creator, I will say, we know a lot of people making newsletters now. I don't know that I can think of a single one whose journey at some point didn't involve a piece of paper with manual signup and then going home later and trying to read what the fuck somebody wrote on their piece of paper cause their handwriting is terrible. I think everybody has that story for that reason. I don't know if Bruce, I mean, I feel like you're the one with all the fun, creative thoughts about this.

Bruce Pinchbeck: 40m 11s

Well, if you're saying a hundred to 200, I think the first thing is the people you know in this space or friends and family is the most obvious. Get people in there and start getting critique.

The other thing I think is big in that initial phase is we really embraced what we say our value was embrace the beta, meaning things are rough. We're learning. We're going to be really transparent. I think the thing you're talking about, too, with these Twitter threads that are transparent, is people love to just see vulnerability and be a part of it and have a conversation.

That was a big thing for us too. 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. You can get to that fairly quickly.

I think that vulnerability also takes some of the edge off the salesiness of sign up for my thing. It's I really care about this community and here's what I'm trying to build. I would appreciate if you would check it out. That would be my easiest, lowest hanging fruit thing to do.

Then beyond that, referral tool technology has grown a lot. We built 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 a little moment of check out this thing I read. This is kind of, part of my identity is supporting this group and I want you to know about it. I think if you have some ability to do that as well, that can help tremendously.

Chris Sopher: 41m 27s

I think that applies to the business side too, where somebody gave me the advice go to the people who are never going to invest in your company first. Or in 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 valid customer targets or advertisers or investors.

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. We talked to advertisers who were 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 and tear this apart if you don't mind.

That was so useful, even when we were early because we sort of got it out of our 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 shaking out the parts that were broken and it felt a lot more polished.

Courtland Allen: 42m 19s

People underestimate how helpful other people on the internet will be if you're actually legitimately working on stuff.

If you've got nothing going on and you're just like, Hey, I've got some ideas I'm noodling on and 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’ve actually started working on something, that you've probably run into some roadblocks and you can message somebody else who's working on that thing and give them specific information about what you're working on, what you're stuck on. Ask them specifics about what they're working on. It's just way easier for people to help.

Bruce Pinchbeck: 42m 50s

Don't ask to pick your brain. No picking brains, please.

Courtland Allen: 42m 53s

Yeah don't be vague. Respect people’ time. Don't ask them to meet for no discernible reason. Don't ask them to meet just because you want something from them. They've got other things to do.

I do this for Indie 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. Then when somebody's name comes up, I'll think, Oh, this is really interesting for reasons X, Y, Z, and I'll message them. I'll say something about their product, I'll offer an idea or something and try to get them on the phone.

Pretty much everybody says yes to that because who's going to say no to somebody who can potentially help you with what you're working on, messaging with ideas and tips. 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 a highly motivated, engaged person who can respond to exactly what you're saying, who knows about your situation, is going to give you much better information than you could find probably written anything.

Bruce Pinchbeck: 43m 41s

I might regret this. I'll say to anyone listening, if you want to talk about, let's say newsletters and what you're working on, holler at me, send me a note, drop me anything 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 link articles to awesome stuff that are resources, but 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 speak out on this one topic for a minute. Typically, you don't expect anything from it other than a great conversation and maybe insight to a new perspective.

Chris Sopher: 44m 15s

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 things like that, because there are always people who will sell advertising or software or sponsorships.

Their outreach, email, or Twitter DM or whatever is like, hey, we'd love to chat, but it's actually like, I want to sell you something. But I don't say that on the cover. It’s 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? Cause if they're not interested, you better find out fast, like save yourself some time.

Courtland Allen: 44m 48s

Don’t bury the lead. If somebody emails me or DMs me and they're trying to hide what they're going to ask, not only am I probably not going to say yes to the thing in the first place, but now I'm suspicious. Why are you hiding this thing from me? Why don't you just tell me what it is? Don't DM me and ask me if you can ask me a question, just ask the question.

Let's talk about Letterhead. You haven't quite pivoted. You're still doing The New Tropic. You're still growing in cities across America. Still making millions of revenue from that. But now you've got this new SaaS 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 they realize other people could probably use that as well. So. what is letterhead? Why'd you start it?

Chris Sopher: 45m 26s

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 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. The biggest challenge if you're a small team or even a big team, but your small team or an individual, is sure, that sounds nice, but how am I going to possibly juggle all those balls at once? It's impossible.

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 s 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.

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 was less overhead, way faster, and with an eye towards 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.

Courtland Allen: 46m 52s

Right. Who's your ideal customer, right? Of course, like Substack exists. A lot of people are using Substack. Mostly individual newsletter creators who just want to get the word out and Substack kinda helps them, gives them the writing tools and a website and the community and a newsletter and some payment stuff.

How do you guys see yourself in alignment with tools like Substack and Ghost and MailChimp, et cetera?

Chris Sopher: 47m 13s

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? 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, you know, 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. Then for these things to integrate with other tools, those are the kinds 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.

We talk about Letterhead as a set of business tools, right, rather than a writing platform or something like that because they're already some awesome solutions for that. We hear from people who are kind of graduating from Substack quite a bit recently. We talked to people who are wanting to start a newsletter and we send them to Substack because they described their needs. We're like, there's actually an awesome tool for this already.

We see it kind of like that. 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. It's really hard to use a tool like MailChimp for that. It's just not designed for it. That's why we actually integrate with ESPs like MailChimp. You can stay with MailChimp and use Letterhead on top of it to do your newsletter and your advertising and your subscription.

Bruce Pinchbeck: 48m 42s

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. You know, there's submit your typeform and we'll email you back and forth. They're seeing the breakdown in that process and want to offload that. 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.

Courtland Allen: 49m 8s

Yeah. When I first started Indie Hackers, I had sponsors and I put them on the website, the podcast, and the newsletter. The newsletter was 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 where people were able to come kind of sign up and upload their stuff.

So, I had a million emails, people were sending me, I'll use this image, wait a minute, use this image, et cetera, et cetera. I was probably spending like 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.

Bruce Pinchbeck: 49m 34s

Yeah. It's fun to make the money until that high settles down. You're like, Oh, I have to go write the newsletter now. Oh, that other sponsor didn't send me an ad that I need.

Chris Sopher: 49m 40s

Exactly.

Bruce Pinchbeck: 49m 41s

Oh, I have to go write the newsletter now. Oh, that other sponsor didn't send me an ad that I need.

Courtland Allen: 49m 43s

Yeah, exactly, exactly. You gotta to track all the stats, et cetera.

So 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 info products and paid newsletters and communities and courses, 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 and people aren't paying that much to begin with.

What do you attribute the sort of month over month doubling of your growth to, and being able to hit $25K a month in revenue and under a year?

Chris Sopher: 50m 14s

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. One of the things we ran into as publishers ourselves is there's an infinitely expanding universe of tools for so many things.

I certainly have they shiny object problem with like, hey, here's a cool new tool I could use. But you have to switch and migrate and train everybody. 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.

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 buy everything we do and do this complete migration. It's not Salesforce where you have to spend 12 years adopting it and it’s this complicated thing.

We try to be really deliberate about that. I think that helped us. 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.

It's still early days there. We're still learning a lot about 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 a different audiences. They have big audience numbers they want to hit. But they want to reach engaged actual human beings in a direct way.

They like newsletters as a channel for that. So, we're helping them do that across the different newsletters that are using Letterhead. That's a big percentage of our revenue as well. Having both of those revenue tools that are disposable has also helped us grow really quickly.

Courtland Allen: 51m 46s

I love that because when you think about a SaaS tool, I mean, it's a programmer’s wet dream. I'm just going to code this thing and it's just gonna be a money tree, then I'm going to be rich or whatever.

If you think about the problems that people have, a lot of them are kind of service-based problems where like, they don't know how to grow their newsletter. They don't know how to find advertisers. Sometimes those are the most important problems, 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.

This idea of a passive income generating SaaS tool, although it's attractive, it's usually a pipe dream. Most of the people I know working on SaaS tools are still working every day, everybody working on services. So, I like the idea that you're combining the two.

There are, for example, Megaphone and podcast hosting, they'll host your podcast, but they'll also programmatically insert ads into your show when you don't have an ad that you found. It's like, okay, well, they're doing this cool service for you in addition to hosting so why wouldn't you use that

With Indies Hackers, we're sort of building and almost Substack clone for people who want to start newsletters. Like you guys ours is compatible. So, a lot of our early series authors have Substacks we’re like, Oh yeah, keep your Substack, but also write for Indie Hackers. We'll help you with is distribution. We'll put you in front of the Indie Hackers audience and get you a lot of users. That's very service-based for us, but they love that because Substack isn't helping with that.

So, it's super cool that you actually help your early customers with advertising rather than just here's a tool it'll help you write and help you publish, but that's it, it's nothing but a robot and that's all you get.

Chris Sopher: 53m 14s

Bruce has been doing a lot of this, 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 using Letterhead. 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

There's so much of that that's advice out there that's generic but getting from zero to doing that is the hardest part ao how do we give people a little ways?

Bruce Pinchbeck: 53m 40s

The thing I'm trying to learn right now, and I would love, again, send me your questions about newsletters, but also I'm curious, what are people actually going to ingest?

These are busy people. They're hacking away. It might be the side hustle. It might be the full-time job, but if I make a tutorial webinar video, 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 work on a membership call to action. That's currently the journey I'm on is trying to understand where to meet people at.

Then my last thing is Courtland, we should definitely figure out what's going on with this Indie Hackers newsletter and figure something out. Wink, wink.

Courtland Allen: 54m 21s

Maybe we should be collaborating.

Bruce Pinchbeck: 54m 23s

No, the one thing I wanted to add to the end of that is I see in the newsletter community the immediate thing is membership, which makes a ton of sense. I have users sign up to membership, get me some MRR 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 in how do we sell ads, sponsorships, and things like that. Membership was like almost an afterthought for awhile. It was just like we have this thing, if you want to be a member, great. We have special content and events and discounts.

Since the pandemic, we’ve right-size that; go to your audience and kind of open, like, hey, we need support. It's been helpful for us as well to just understand how you can play those two things to build more revenue. 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.

'm getting anxious. I see these groups out there and I'm 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. Could we help serve them? Could they hire more writers? Could they expand to new new markets? That's going to be the thing that gets exciting for me.

Courtland Allen: 55m 31s

I love this whole area. Because, Indie Hackers, 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 the very top of the funnel of entrepreneurship, everybody was on the fence of can I start an online business or should I keep working at my nine to five? The easier it becomes to start an online business, the more people who do it.

The fact that 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. The fact that you guys and other people like you were 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, et cetera. That’s kind of like the first steppingstone and to being financially independent indie hacker. So, I love what you guys are doing.

We're about out of time here. 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 indie hacker who's just getting started and maybe they don't know what they're gonna work on and maybe they just took the very first steps. What do you think they can learn from what YouTube have learned?

Bruce Pinchbeck: 56m 33s

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.

You're going to spend a lot of time, 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 and the Twittersphere that you're not a part of and start to really understand it. But that would be my thing. Do the little bit of that research, take a pause.

Courtland Allen: 57m 9s

I love it. So just to summarize, start by understanding your customers, your community. You really only get a limited number of attempts to try to figure out what people want. You can cut down on the number of attempts required by really focusing on people.

I love that because it's kind of fun. You know, when you sit down and you start coding and building, it's very lonely and isolating and it’s a lot of stress because you're not sure if people want it. But if you start by doing nothing, but having calls with people and reading what they're saying and talking to them and, like you guys did, following them around the city, that stuff was just kind of very fun and energizing. So, I love that you start that way.

Then the second, point break your giant journey down into a lot of bite-sized steps because it's not going to be you just go from zero to a million in a day. It's going to be a long windy process and if you go to 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.

Chris, Bruce, thanks a ton for coming on the show. Lot of good advice. Great story. Some good chatter about local news. Thanks for coming on.

Bruce Pinchbeck: 58m 2s

Thanks so much, Courtland. Appreciate it.

Courtland Allen: 58m 4s

Can you let listeners know where they can go 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 then content and whatever else might be on their minds.

Bruce Pinchbeck: 58m 16s

Well, first you could check out Letterhead. It's a try letterhead.com. You'll see a little bit what we're working on there. Obviously, we have a contact form if you want to kind of talk deeper about that, but I'm personally, you can send me a note at [email protected] That's my email, or follow me on Twitter, @BrucePinchbeck.

Courtland Allen: 58m 35s

Listeners, if you enjoyed this episode and you want an easy way to support the podcast, you should leave a review for us on iTunes or Apple podcasts. Probably the fastest way to get there if you're on a Mac is to visit indiehackers.com/reviews. I really appreciate your support and I read pretty much all the reviews you leave over there. Thank you so much for listening and as always, I will see you next time.