The Best Way to Build Community is Easier Than You Think with Drew Dillon

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Most attempts to start a community these days feel a lot like the approach the Underpants Gnomes from South Park took in making money. Step 1: Launch a Discord, Step 2: ???, Step 3: Community! But it’s not like that at all. And Drew Dillon, founder of Burb and community expert, is here to set the record straight.

Top Takeaways:

  • You need to think of the community as a business. Create a reason for people to care and engage. And close the look by making sure the community isn’t just about you – it’s about people connecting.
  • Start with a hypothesis. Ask what you think your audience has in common and why they might want to come together. Then test and iterate. Start with a Zoom call first and see if people want to connect after.
  • Do things that don’t scale at first. With 10-20 members, you can really get to know them and understand their needs (and those of the community). Around 50, you’ll likely need to start automating.

Show Notes:


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Most attempts to start a community these days feels like the same approach the underpants gnomes took in South Park to make money. Step one, launch a discord. Step two, aaah. Step three, community. But it’s not like that at all. Drew Dillon, founder of Burb and a community expert is here to set the record straight.

Throughout this episode, I want you to look for these top takeaways. That you need to think of your community as a business and create a reason for people to care. That when you’re building a community, start with a hypothesis and what you think your audience has in common. The previous two episodes will help you understand that a little better. And don’t do things at scale first. This one was really illuminating to me because I always over-engineer things and I think that I need to put the perfect system in place before I have even one community member or one paying customer. But do things that don’t scale at first. I think you’ll love this episode, especially if you’re trying to build a community or have aspirations for building a community.

In How I Built It Pro, we are going to talk about Gumroad and their move to charge sellers 10% flat across the board. I hope you enjoy this episode. You can find all of the show notes over at Thanks to this week’s sponsors, Ahrefs, Paid Memberships Pro, and LearnDash. You’ll hear about them later on in the show. But for now, let’s get to the intro and then the interview.

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Intro: Hey everybody, and welcome to How I Built It, the podcast where you get free coaching calls from successful creators. Each week you get actionable advice on how you can build a better content business to increase revenue and establish yourself as an authority. I’m your host Joe Casabona. Now let’s get to it.

[00:02:58] <music>

Joe Casabona: Hey everybody. I am here on Episode 299 of How I Built It with Drew Dillon. He is the founder and CEO of Burb, which is really cool… There’s a couple of things that are really cool about Burb, and I’m probably not going to do justice. So I’ll let drew talk about those. Drew and I got connected, thanks to Jay Clouse’s community. He had a really great episode of SPI that we’ll also dig into. So without further ado, let’s bring in Drew. I didn’t mean for that to rhyme. Drew, how are you today?

Drew Dillon: Good. Thanks for having me, Joe.

Joe Casabona: Thanks for coming on. In the pre-show, we were talking about how you did work at Yammer. Was it you you were also at Patreon or was it your co-founders who were at Patreon?

Drew Dillon: Oh yeah, one of my co-founders and one of my very best friends was at Patreon.

Joe Casabona: Nice. So you have a lot of experience in the community building area. We’ll get to Burb in a minute, because Burb is kind of the solution to I think what could be a lot of problems and building community. I’ll link to this in the show notes but I did an episode of my podcast where I talked about my failed attempt at building community, largely inspired by your interview on SPI, which I’ll also link in the show notes.

But I guess the main question and maybe a common thing that people think is community. Can I just start a discord and now I have a community? Is that it? Just join and now we have a community?

Drew Dillon: Well, I think there are probably a few million crypto discords that are in graveyards right now that probably would disprove that theory. Fundamentally, I think you have to think about a community especially if you’re building a community business, if you’re intending to monetize, sell memberships, or even have a free community where you deliver paid content, and that’s just kind of like your distribution method for paid content, you have to think about what you’re building in terms of building a product. That’s really where my brain always goes, to my product builder.

But the reason and why people are going to come back, why they care about it, why they’re going to engage, and then figuring out kind of the closing the loop of the product, at the end of the day, the community isn’t just about going there and meeting you the creator, but it’s about the other people there. That’s kind of the secret sauce of community ultimately.

So you have to think about all those different moving pieces kind of separately, the why, the what, and then the connection. And then I think if you have all of those components, then you’ve got a really interesting community business. And that’s how you kind of create a thing that keeps growing and keeps perpetuating, and really offers a lot of value to your members.

Joe Casabona: I like that a lot. Like you said, I mean, it’s not necessarily just about direct access to you the creator. If people want that, then they could probably pay you for coaching or private consulting, or whatever. So that’s really not a community part.

And then the other thing is the Field of Dreams approach doesn’t work, right, that if you build it they will come? They won’t come. When I talked in my episode, my cold open was basically about building community and how I felt like it was easy in college. Like you would just go somewhere and other people would be there. Or if you want people to come to your event, you would say like, “Oh, there’s free pizza.” And I thought like, “Oh, building on the internet would be super easy because there’s no geographical boundaries.” But there is a lot more competition, right? Like on a Thursday night on campus, especially a dry campus, there’s probably not a whole lot going on. But on the internet, there’s a lot, a lot going on. And so you need to create, like you said, the why, the reason for people to come to the community.

Drew Dillon: Yeah. We think about this a lot in terms of product development. Because if you’re building a SaaS tool, if you’re building a consumer website, your competition is every other website on the internet. If I can flip up another tab to Twitter, if I can stare at my phone and watch TikTok instead of listening to a podcast, that’s your competition.

People joke a lot about MBAs and how worthwhile they are in technology. The one thing you really learn from MBA is how much modeling that stuff, building the graphs and charts of user activity looks like econ, because at the end of the day, that attention is actually modeled… It works a lot like currency. So currency, monetary, exchange, things like that, that actually maps really, really closely to attention and paid ways people spend time on the internet.

There are unique moments where, you know, it’s going to be a lot better easier to listen to a podcast in the car or when you’re on a train, something like that. But when somebody’s sitting down in front of a desktop, it’s primetime. You’re competing against everything on the internet that they could possibly do. And you really gotta have a reason for somebody to care.

Joe Casabona: That’s super interesting. Attention is a lot like currency. It’s even more scarce, right? I think Bill Gates said this. The only thing you can’t make is more time, right? Well, certain types of people can tend to make more money when they need to make more money. Nobody can make more time. So we all have the same amount of hours and we’re all competing for those hours. I love that. That’s super interesting.

So my next question here, and something I struggle with a lot, and it looks like Burb kind of works with a lot of different platforms is, how much does this platform matter? I think I lost a lot of community members along the way by changing platform thinking, “Well, you know what? People just don’t like Facebook, so we’ll move to slack. Oh, people are Slack-fatigued, so we’ll move to Circle. Oh, people don’t have a login for Circle, so they don’t…” How much does platform matter then?

Drew Dillon: That’s a good question. I would say there are times where it absolutely matters. But on the whole, I would say ish. The biggest determinant of success will not necessarily be the platform. There’ll be format considerations.

Something like Slack or Discord are very chat-based. I tend to find chat-based communities can feel overwhelming or they can look dead and there’s like no in-between. Whereas something like Facebook, which is a little bit more like a forum or Circle or Mighty Networks or something like that, those are a little bit more approachable in terms of, you know, when I come in, I don’t feel like I have to go read every single possible thing. I don’t feel like I have to respond to every possible thing. The content can age a little bit and it doesn’t look like the community just died.

And then I do think there is a good size consideration of technical acumen and where people are. So a lot of Facebook communities do have trouble moving because Facebook they’re already there. Flipside of that with a certain type of audience, they hate Facebook, and are never going to be there. So that does create at least a gate at the beginning. And something that we hear a lot about is like “Not another login. I don’t want to log into this thing, that thing, this thing, that thing just to see what’s happening in the community.” And some people will be allergic to even one other login. Those elements do come up. I don’t think they’re as impactful as people can wrap their heads.

Joe Casabona: Yeah, for sure. I mean, one of the reasons that I was paying for the higher tier in Circle was because my courses were all in WordPress. And I thought, “Oh, well, Circle will allow single sign-on with WordPress at the higher level. So that won’t be yet another login. That’ll surely get people to join. And it didn’t, probably for a few reasons, right? I wasn’t creating a reason to be there. I was having my VA, or later, Zapier post prompts, the same prompts every Monday, Wednesday, and Friday.

All of my courses are self-paced. So people were taking them at different times. And if someone was taking the course, they would post questions in there but my courses weren’t selling as… It’s not like I was selling like dozens a day or whatever and a lot of people buy aspirationally. It was usually one person posting a question and me chiming in with the answer, which is not very community-based. Again, I think I missed the boat, because for my two biggest launches, I didn’t have a community and so I missed the opportunity there.

So I think you’re right. I always got held up because I was like, “Do you want Facebook, Slack or something else?” And it was always like half Facebook, half Slack. And then people going like, “Oh, Slack is only for work,” or “I hate Facebook.” And I’m like, “Great, I don’t know what to do?”

Drew Dillon: Well, we find a lot of times is… You know, and we started our own community this way. We started out with just Zoom meetings. Like cool, we’re going to do group coaching, once a week. Tuesday, Thursday session, two different time zone so you can figure out what works for you. We have a Circle space. But that is going to be where we put the content, the output of our Zoom meetings, and like, don’t feel like you need to engage there. That’s not what we’re expecting from you and using that space.

And then over time, we started to build up more and more content in there, and more reasons for people to be there such that it did actually start to get some usage in the Circle space. But even today it’s not buzzing the way Jay’s community is. It’s quieter. But at the same time, we’re like, Okay, well, we built a community, we built relationships, we build reasons. Like people do come back when we reach out to them. So it’s there.

Joe Casabona: Shout out to Jay, I’ll link to his episode as well. He’s done a really good job to the point where if I’m gone for a couple of days, I almost feel that overwhelm, where I was like, “Oh, there’s so much.” But his is also one of the only communities where I have email notifications turned on for new posts. I mean, Denise this morning, as we record this, posted her experiment about writing a book, which is very prescient, I guess, for me or very relevant to me right now. And so yeah, he’s done a great job.

But I like what you said here, started off with Zoom meetings, and then you have a Circle space, based on again, what you said in the SPI interview, more events, invite coaching clients into the community and make it so that they can talk there. Those are things that now with the Podcast Liftoff Playbook, which is my newest product, right? I had courses all over the place, like WordPress and development and podcasting or whatever. Those are all free on YouTube now. And I’m really focusing on only podcast content. So now I have the playbook.

That’s how I’m working on building up the community now. So it’s really a synchronous at this point. Every quarter, I’ll do like a short cohort sort of thing via Zoom and then I post the replays in the Playbook. And then I’m also doing these experiments. As I was recording the first one, I was like, “Am I stealing this from Jay?” And I’m like, “No, I wrote this down like a year ago.” It’s a lab and experiment. It’s not like one person’s idea.

Where I’m encouraging them to ask questions and post comments in a very asynchronous way, as that grows, maybe I’ll find the need for real time chat or a forum plugin that’s not bbPress. Sorry, bbPress friends, but it’s just like that software’s disaster. It’s like bolting a jet engine onto your electric car or whatever. Like it’s too much for that. Anyway.

But I’m doing exactly kind of what you recommend. Isn’t that right? Like, do some more live events? Make it so people can access the content in a single place and keep creating content that makes them want to log in more. And I’m doing that on kind of my own timeframe now, which I think is going to be slower. But I think I’ll actually end up eventually with a community of podcasters.

Drew Dillon: I think about, you know, there’s been… I think it’s dying down now, but there was this huge wave of like everybody doing cohort-based courses. We looked at that as it was coming up and the Burb product was built around a lot of initially people doing cohort-based courses because they have extremely high operational needs. Like, there’s content, there’s meetings, there’s assignments, there’s all this kind of stuff. How do you orchestrate and drive all of that kind of stuff through a community space?

But I think that the hype of that is dying down a bit. I think what we retreat back to, the baseline of this is that people learn in different ways, they want different things out of their learning experience. And ultimately, learning is about some form of transformation. So if you buy a course, you buy a specific piece of content, that is about learning something very specific on your own time, don’t necessarily expect a ton of support out of that. Support is kind of a bonus in those sorts of scenarios.

Then you have a cohort-based course, which is time-boxed, it’s extremely interactive, it’s community-based. So what that really is good for is rapid transformation within a short period of time. From now until when this thing ends, I want to get better at this thing. I know exactly what that thing is.

Also, the offer needs to be very, very clear. Like, “Here’s where you will be at the end of this month and a half, three month cohort.” Also because there’s that time commitment, you’re expecting a lot of that. And that’s why it tends to be very expensive because they’re putting in a high investment.

Whereas you can think of the final piece, which is a learning community, or a community of interest, these are people who are on a much longer-term journey, who are looking to meet other people on the same journey, who are looking to grow together in the same direction. And your goal there is, just like any product, getting to a narrow enough kind of definition of what that journey is that I, as somebody who’s coming in for the first time, could say, “Yes or no, this isn’t for me. This is for me.” But also that I know who those people are going to be, who am I going to encounter in this community, what are we going to do together.

The beauty of that one is really you can kind of take a step back and be more of a guide rather than the other two where you’re still kind of the creator on stage. So you can kind of shape the community, shape the growth paths.

And something I think we don’t do enough of and memberships and community which is also graduate people. Like, You’ve done it. You’ve achieved the thing you wanted out of this community. Maybe you can stop paying a membership and come back as a mentor. We can interview you, but you’re done. Well, thank you.”

Joe Casabona: That makes perfect sense. Because I think like the other thing is you think about memberships is, “Oh yeah, we got to prevent churn at all costs.” And with a community, a learning community, your online courses, there’s gonna be a point where you… You know, you don’t pay for college forever. Like you said, you graduate at some point.

I think it’s healthy to want to graduate people. And you could always kind of continue growing with people for a long time. It’s not like three years, and then you’re done and they’re never going to be a customer again, right? Maybe for me, it’s three years to help them launch and grow their podcast. And then maybe they want private consulting for me to help get more sponsors or build their membership or whatever. I think that when you have a learning-based community, like you said, it’s healthy to think about when will they graduate.

Drew Dillon: Yeah. I think about a lot. I used to do a lot of product management-related meetups and stuff like that. Most of the people you’re gonna meet at those product friendship-related meetups are trying to get into product, or they’re very, very junior or like trying to get a job. So for me, who had been in the field for like 10 years, the conversation is not great, it’s not useful for me. They’re still talking about one on one stuff, “How do I convince my boss?” I’m like, “I am that boss. I don’t need to be on this discussion. I’m not getting anything out of it.”

So we branched off. We created a product leaders group. The only challenge there is, with any community, those people are extremely busy. So just getting people to meet up for lunch once a month was challenging. But at the same time, when we actually didn’t get together, the conversation was just very different on a much better level for me. If you’re the person who can lead the leaders’ group as well, you can also think about it as new offerings and new capabilities in your community.

Joe Casabona: Yeah, absolutely. I really like this dynamic that you presented here. Because I think like, yeah, cohort-based courses were all the rage. I wanted to do one and then I realize that launching a podcast is maybe not the high-dollar CBC that I would want to have, especially because I have all of that self-paced. And so I think more like group coaching, guided coaching is really the thing that for four weeks, a bunch of people can come together and we could talk about either launching any podcasts or getting your first sponsor, whatever. And then they have the opportunity to ask me questions as a group. I think that’s really the model that’s worked for me lately.

So, in 2023, I’m really gonna lean into that. I really like what you’ve presented there. Let’s take a step back for a minute. Let’s say somebody has a mailing list of say, I don’t know, 1,108 people, and many of them were from a previous product but they’re still somewhat engaged. What would that person need to do to kind of reengage those people into community? Like, let’s say, I’m starting from… I guess I’m almost starting from zero here, right? Or someone listening is maybe starting from zero. How do you build that community? How do you get people to want to participate?

Drew Dillon: The first thing I would do is form a hypothesis. Okay, based on these 1,100 people, what do I think they have in common? What is the largest group in this audience? What do I think that they need? Why do I think they would want to come together? Where do they see their journey going? And what are some of the interesting things that we could deliver that would keep them coming back?

To that effect, if you’re doing group coaching and stuff like that, also not get too narrow on your definition of community. It’s okay and it’s fine to have an expansive definition of community that includes those Zoom meetings. Like high Zoom attendance, high email open rates, group chats, and stuff like that are 1,000,000% community as much as paying for a big community platform.

So when you form that hypothesis, say, Okay, now I think I have this person in my audience. I think they’re about X number of them, this is what I think that they want Then the next step is to get a couple of them on the phone. Like start talking to these folks.

The hardest thing here is not push-polling. It’s not telling them what they want. Because when you get somebody on the phone like that, when you get them on the Zoom, the natural social inclination is to be like, “Yeah, Joe, that sounds like a great idea. I’ll absolutely show up to that thing.” No, they won’t. You got to find ways of asking the question without asking a question.

And when they start repeating back to you your own hypotheses… Your hypothesis should evolve as you’re talking to all these people. Like, what would you want out of this? What are you looking for? And what way are you hoping to grow? Do you think other people can help you with that? When you start hearing the same thing over and over again, “Oh, yeah, well, I would show up for this. This is really interesting. I’d love to meet people in kind of this position.” I’m sure hearing that over and over again, like, Okay, that’s interesting. Now you’ve got a reason to gather information that they’re going to want other people that they want to talk to.

And then the next piece is testing into it in some way. That’s where an event group coaching thing maybe set up a single events or a workshop series over time, smaller overall dollar amount just to kind of test into it and see who buys. Like they said they were interested in this thing, are they going to put their money where their mouth is? Are they actually going to buy the thing?

And then if they do, then great, you’ve figured out who you’re targeting, what they’re interested in, that they will pay for it. And then all you really need to do is start connecting those folks. Like actually doing that work. So in that workshop series, leave time for the breakout rooms, make sure people are actually chatting, follow up surveys, ask them if they’d like to connect with each other after the event, ask if they would like to continue the events.

And then just keep iterating from there. You might need any one of these steps. You could sit there from now until forever. You need to figure out whether or not that’s a thing that they want. But then once you get past kind of all those steps, then you can open up a small beta community. Use those folks. Like we were talking about before, have a space that it’s primarily for content. Keep most of your community and Zoom, and just see kind of what happen and evolve it from there. And then eventually open it up wider when it seems like people are really engaging and enjoying the experience.

Joe Casabona: Yeah, that’s such great advice. I want to key in on like get a couple of them on the phone. Because this is a common thing when you’re thinking about a business or a product. Like, “Oh, would you buy this?” “Yeah, sure I’d buy this, I guess.” Like, “Is that something you’re interested in?” “Yeah, I’m interested in getting more sponsors.” Somebody was like, “I want to show you our sponsorship platform,” and I’m like, “I have a system.” I told them straight up, “I’m not gonna get your product. I have my system. I don’t really see the benefit in me paying for you to do it or having my sponsors pay you to connect them to me.” So that’s just not…

But most people won’t do that. Right? They’ll be like, “Oh, yeah, I’ll hop on a call with you. I think that’s asking open-ended questions about, you know, what are your biggest struggles, how do you find guests maybe is a good one. Again, as I’m thinking through, maybe podcast swaps is a good idea for my community for people to connect with each other because that’s a proven way to grow a podcast. And finding people to swap with can be hard sometimes. So I think that’s really good.

Now, let me ask you, because I… if the people who organized this conference happen to be listening, this is not a dig at you, this is just something I’ve been thinking about a lot. But I sat on this panel for a conference and the conference was like, “Oh, we want to talk about building.” Because they got me to agree to the panel before I knew the topic, but like I proposed to talk.” And they’re like, “Oh, we want to talk about building community.” And I was like, “Okay, if that is the case, I am not qualified. I have not successfully done that even once.”

Maybe, Drew, based on your definition I have. Because I had people coming to some meetups and webinars or whatever. Before today, my definition of community I was not successful. And they were like, “Well, don’t you think a podcast is a community?” So is a podcast a community? Or what is the one thing? Even if we go abroad, what’s the one thing that makes a community a community?

Drew Dillon: I’ll disagree with some people on this, but I think fundamentally it’s the people are pointed at each other. Like it can be that you are delivering content but there needs to be the follow-up piece of the audience connecting with each other that forms a community to me.

Some people will say that a newsletter is a community. I don’t agree with that. I think it can be if you highlight a person in your community, you know, somebody you’re connected to in your newsletter, and the newsletter respondents reach out to you and you connect those two people. That can be kind of one of those proto communities. But I think fundamentally, things that are more broadcast from career out are more of an audience not a community for me.

Joe Casabona: And that was pretty much what I said. He’s like, “I really think your podcast is a community.” And I’m like, “It’s not because it’s a one way street, basically.” Some people write into me sometimes, but I’m not connecting my listeners, either with me or each other really. I mean, it’s not like me and my listeners, except for the people who are paying for Pro, which is closer to a community. And I would love to connect them but they’re really base pay me five bucks a month for the extra content at this point.

Again, I said to a friend, I was like, “I shut down Facebook. I shut down Circle. I shut down Slack.” And I was like, “Maybe I’ll spin up a Discord. That seems like a good thing.” He’s like, “Stop. Stop it. Don’t do things people aren’t asking for.” Don’t do things people are not asking for.

Drew Dillon: My CTO is a big fan of the newsletter Garbage Day. And I gather they’ve got a Discord. That’s one of the paid tiers in their Patreon. And so that because they’re in there all the time, they’re chatting about their articles, they’re talking about it. You know, there is a real community that then flows from the newsletter. And that’s the difference is like the newsletter is a reason for the community and the community does exist that they gather together.

Joe Casabona: At some point, I thought, like, “Oh, one of the things that we’ll do in the community is talk about the recent episodes.” I realized that people just wanted to kind of learn from the latest episodes. They didn’t really… Oh, well, I thought nobody really cared to share their thoughts on that sort of stuff. And I’m not talking about controversial things. I’m getting advice from you. Hopefully the listeners find it useful. I certainly find it useful and I have a lot of ideas. I think I really like that bit.

Again, if you’re a pro member listening right now and you want to connect with other pro members, let me know. We’ll probably start with Zoom. I think that probably makes the most sense. And then I’ll have other things in the newsletter. I’m on really early days with the ConvertKit integration right now. I think that I can make paid newsletters available for paid subscribers but I’m not even sure about that. Like, we might just have like a password-protected Airtable or whatever for you to access both content.

If you want to know what Drew and I talked about in the pre-show, and we’ll talk about the post-show, you can pay five bucks a month or 50 bucks a year and sign up over in And that’s ad-free, extended versions of this show, every show for the last two years. A year and a half maybe. But anyway, that’s This is one of the things we talked about in the pre-show is I moved away from WordPress because I wanted a really light architecture. And I think I’ve gone to light. I think I had heavy cream and I went to 2% milk and now I have skim milk and no one likes skim milk. So we’ll see. Hopefully, some of the things will get resolved.

We’ve been talking for a while already. I think we covered some really good topics. What makes community community is… I love your answer. You have a product called Burb. You have a company/product called Burb. And Burb just created something called Launch by Burb. So first I want to ask you, what does Burb do? Because again, I haven’t really dug in and looked at it, but I like the tagline of easy automation and analytics. I love automation. Tell me a little bit about what Burp does and how this can help community owners, organizers, people who run their own communities.

Drew Dillon: Yeah. We think about it as community first businesses. And fundamentally what happens, you’re a creator, you know, you’re in these early stages, you’re figuring out what the community wants, and you’re building it for them, and then all sudden you kind of like you hit it. Like you’ve got a community of maybe 10 to 20 people, they’re now engaging, everything that you do at that stage is all bespoke. Like you’re sending them custom DMs, welcoming them to the community there. You’re checking in on your own metrics. Like, “Okay, who’s logging in. I haven’t seen so and so in a while.” You can keep all of that in your head.

And then there’s something that happens. Kind of we found it’s really somewhere between 10 to 50 members, all of a sudden, all the things that you were able to do at 10 members that really made the experience special, just stop working like you can’t do them anymore. Fundamentally, it’s like an n squared or a telephone problem that like, you know, where you could have sat down and written 10 thank you DMs to everybody on the holidays, going and writing 50 then becomes really, really onerous, and especially if the community continues growing faster and faster beyond that point.

So what you need are things a little bit more like, you know, marketing tools. You need to start automating. But most of the folks are doing this of course don’t come from a tech background. Like Zapier is scary. If you wanted to have a memory of what people have done, you need to figure out Airtable. And you spend all of your time… We look at these scaled communities and people have figured it out.

You know, people like Jay figured out Zapier a long time ago. He knows how it works. He’s super comfortable with it. When he needs to build a new automation, he just goes and does it. But for everybody else there’s a huge barrier of getting from one to the other. And that’s an easy place where a lot of communities die.

And philosophically, we thought, if so many communities are dying at that moment, what if we could take all of those best practices, package them up, put templates around them, make them really, really easy to use so that you can kind of push past that barrier without having to go learn a bunch of new crazy tools. Just make it that much easier to succeed at building a community business.

So the first and easiest things for us to build were all about messaging. If you wanted to send 10, 50, 5000 DMs at a time, you know, that’s actually something really easy for a computer to do. It’s really hard for a person to do and literally no product in the community space has that ability. So we have the ability to send bulk DMS with email marketing, like customization in the first names and pull in the variables and stuff like that.

Joe Casabona: Oh, that’s cool. Justin Moore does that for his cohort-based course. And Pat Flynn, because I’m in the SPI Academy now, too. And I was wondering how-

Drew Dillon: And guess what those people have in common.

Joe Casabona: Interesting. It feels like Zapier would timeout doing that yet, right?

Drew Dillon: Yeah.

Joe Casabona: Because you can’t really loop stuff in Zapier effectively.

Drew Dillon: You couldn’t even do it in Zapier because you’d have to build an Airtable to tell it to go do that stuff.

Joe Casabona: Right. And then the Airtable would have to update because that’s how Zapier works. It’s going to look at, Oh, what column has changed? That’s really interesting. But Burb does that. That’s really cool.

Drew Dillon: Yeah. That was the first thing: messaging, even posting on a schedule. If you’re running a course, if you’re running a cohort, you want messages to come in weekly, like you were talking about your VA going in and logging in and posting the same message, we can actually pre-schedule out that content, put it in drafts months in advance.

Joe Casabona: Oh, nice.

Drew Dillon: And then-

Joe Casabona: Because when I was using Circle, they didn’t allow that. Again, with Zapier, I had to like schedule this thing at the same exact time every week. And like nobody engaged with that, because it just became the same exact post every week. But scheduling posts, that would be amazing.

Drew Dillon: And then for messaging, we moved to automations. The phrase that stuck for us was like, what if Zapier actually knew what you were trying to do, and it was helpful rather than you reinventing the wheel every single time you wanted to use it? So there are automations around welcoming new members, getting in the posting intros channel, following up with them, even gamifying that experience a little bit if they do things like that.

It’ll let you know who your members who are dropping off and actually send them follow-up messages via DM within your Circle, Slack or Discord community, or even send them an email from your own Gmail inbox, which is a super powerful way of reconnecting people. Recently added Typeform integration so that we can basically automate the onboarding survey. Let’s say you’re trying to introduce podcasters who have different areas of focus, you could ask them their focus area in a survey and then basically when they come in, it could slot them into the right channels within your Slack so that they’re in with other people who have that same focus area of their podcast.

And then yeah, built all of these as templates. So they’re point-and-click, so you don’t have to keep reinventing this.

[00:39:01] <music>

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[00:42:40] <music>

Joe Casabona: So let me ask you this now. I didn’t intend for this to turn into a sales call but I’m very interested in this as someone who’s… I mean, right? The tagline for this show is like free coaching calls from successful creators. It’s always been a place for me to learn and grow and help people. And I’m like in the thick of this right now as we talk. You have a free tier that is member CRM activity feed up to 100 members, 1,000 email-only members. What does that mean? It means you can essentially send emails from Burb to these members.

Drew Dillon: Yeah. Yeah. You can load them up via CSV, we can connect to your ConvertKit as well. And those are non-community members We don’t really want to charge you too much for that. Actually, to be fair, we don’t really enforce that even.

Joe Casabona: Wow.

Drew Dillon: Because we’d rather work with your community members than kind of ecosystem of folks that you connect with.

Joe Casabona: I was telling you about all of my problems in the pre-show. It sounds like Burb’s free tier could help me solve some of the problems I’m having.

Drew Dillon: Yeah, 100%. We always caution against over-automating in the early days for that kind of purpose of discovery, making sure you’re doing all the right things. That the stuff you do in the early days it’s the do things that don’t scale moment. And then that 10 to 50 is about taking what you were doing that was really special about your community and then automating that piece of it.

Joe Casabona: Gotcha. I really love “you do things that don’t scale.” Again, software engineer by trade. I released a product yesterday called the Profitable Podcaster Pack that takes a bunch of the resources I’ve created over the years and when they added a few really valuable ones. Like my podcast plan an Airtable and a video walking through how to use it, my automation library, which is an Airtable of like, Here’s all the zaps I use, here’s some TextExpander snippets. It’s very valuable stuff.

And I thought, “How am I going to deliver this? Oh, I guess I could create like a little password-protected page or I can turn…” And then I was like, “No, I’m just gonna make an Airtable and share the Airtable link with them, and they’ll get the PDFs as a zip because ConvertKit does that. And I really had to like fight the urge to not over-engineer because I don’t know if anybody’s gonna buy this. But I know that having an Airtable will be useful either way.

So you know, do things that don’t scale. Again, in my head, I’m thinking, All right, well for How I Built It Pro, like delivering the podcast is easy because Castos handles that. But member-only videos, I’ll do some of those sometimes to supplement the episode. And those are like quick, easy, you know, recorded an Ecam. Unlisted YouTube videos. I don’t know if I should say that publicly. Maybe. But I was like, “How are they going to find an archive of these videos? I guess I’ll just email them.”

I guess what I’m saying is not everything needs to be like a blog post-style thing, right? I’m delivering value in the moment. If people like it, they can bookmark it. I don’t need to provide that service at least right now. And then with my 20 Members, if one emails me and says like, “Hey, where was that link?” I could find it for them at that point.

Drew Dillon: Exactly.

Joe Casabona: So that’s kind of like do things that don’t scale. Something you here, but you know, it’s… there’s timing for it to land. And I feel like it really just landed with me right now. So thanks for that.

Drew Dillon: Think about engagement of those things as like a long-term value. Like near term is, am I giving them what they were looking for, what they’re paying for? And then long term, how do I make sure that it’s easier and easier? Especially because the first people you’re gonna get are going to be the most diehard interested people in the first place. So they’re going to work a little bit harder.

Later stage as you grow and grow, those are gonna be people that have heard about you casually through word of mouth or whatever. They’re not going to put as much time and effort and going to want to. So you have to spoon-feed your later people, your later adopters a little bit more. But the early folks, yeah, they’re going to work for it a bit more.

Joe Casabona: Which I guess kind of goes back to… I think this was in the pre-show too. The kind of vitamin versus painkiller, right? If you truly create a painkiller, especially for your podcast, your community, you probably will get people who are not necessarily diehard fans. They are there for the painkiller later on.

I’m always worried about making it as easy as possible as early as possible. But I need to remember that like…. I mean, shout out to AJ again. AJ has gone through multiple iterations of this with me. He really digs what I’m doing. I mean, I’m picking on AJ, because he was the most top of mine person, but there’s a-

Drew Dillon: Bless the AJs of the world for it.

Joe Casabona: Yeah, bless the AJ is of the world. And I have a few of them who have really made me want to continue doing pro because it could be worthwhile as long as I package it the right way. Yeah, super great insight. Now, we’re coming up on time. You’ve been talking for a long time here. I want to touch on Launch Burb because this is something slightly very different from the actual Burb product, right?

Drew Dillon: Yeah, yeah. I think, we talked about Burb is really about that scaling moment when you’ve got the thing that works, and you’re trying to get it to this better place over time. And I think what we’ve been thinking about a lot is how do we help folks at the very earliest stages. Because we do see, you know, building community businesses, memberships courses, even group coaching, masterclasses, you know, you name any kind of place where people gather and there’s a mentor kind of helping people through something. Most of the people doing this are actually still at the very, very earliest stages.

When you hang out in a lot of communities where folks are talking about this where they’re interested, they’re at a very early stage. They’ll be talking about Squarespace vs. Wix vs. WordPress. They’ll be talking about Thrive cart and Sam cart and this thing and that thing. they’ll be talking about ConvertKit and Mailer Lite, and ActiveCampaign. And then like, “I need to go learn Zapier to connect all this stuff together.”

It cracks me up because I talked to them and they’re like, “Well, I’m not a techie.” Like you’ve been staring at feature requests sheets and building pros and con lists for like six months. You’re as technical as you can possibly be on this topic. You’ll talk to them and a certain number of them won’t have like really done their work and discovery, won’t necessarily have… They need to actually take a step back from tools and go talk to people more.

Joe Casabona: Talking about tools is a fun thing to do, right?

Drew Dillon: Yeah.

Joe Casabona: And that’s why people do it.

Drew Dillon: But for a whole nother cohort, they just like… I don’t know if it’s fear or if it’s just confusion of what’s the best thing or if they’re just trying to gild the lily and just have the absolute perfect moment. But we’re like, What if we just made it really, really easy for you to launch? Like, just take that zero to one step. Finally, stop staring at feature request list. Finally, stop staring at billing forms and trying to figure out Zapier. What if we took the landing page and made it as easy to build as like a link in bio tool. We built tearing around that. We took even a step back from what we do with Burb, like deeply integrating, and just made it’s platform agnostic, so that we don’t care if you’re on WhatsApp, or Facebook groups, or whatever, and we handle the recurring billing for you. We’ll set up the Stripe, we’ll bill monthly, annually, whatever. Can we do that? Would people be interested in it? Would it get people to get off the fence and really finally launch?

So kind of hitting between Burb the core product and Launch talking to different segments of the exact same market of people on this whole journey, and just helping out kind of a broader segment of these businesses.

Joe Casabona: I like that. I basically maintain a product account to log in to vote for my friends’ products. That’s really all I do. And when you launched this [inaudible 00:51:18] product, I like immediately uploaded it, or whatever they call it there, what really appealed to me was it’s like you have a payment form and then you can connect to Circle or Discord, or Discourse or Facebook groups, or whatever thing that doesn’t have a native payment processor, right?

Drew Dillon: Yeah.

Joe Casabona: Like you can do that and then add people to your thing. Again, in the pre-show, we talked about churn. So if like someone stops paying, certain things like they don’t allow you to go in. But how easy is it to revoke access? Quick sidebar. This is also what I’m thinking about too, is like, before I even have a ton of people in the door, I’m like, “How am I going to prevent people from accessing things they are not paying for?” I think I need to get over that. Like, I’m not giving away the world’s secrets here, showing people how I use my Kindle scribe. If they get access to that video, and they don’t pay for it, like it’s fine.

Drew Dillon: That’s certainly how we think about it. There’s fundamentally the need to want to make sure that people are paying for what they’re receiving. And I think that’s fair. I think at a small scale, 100 people, you know, it’s somewhat irrelevant. If 15 of them are hanging out and haven’t paid their recurring fee, that’s not a ton of money. It’s not costing you a lot of time and effort.

But we do regularly talk to communities of 4,000 on Facebook groups that is a paid community, they are supposed to be paying for access. When you ask them who should be in there and who shouldn’t, no idea. They have no idea. That membership that I’m referencing is $500 a month. So that is a serious chunk of money that they could potentially be losing. That’s like an employee basically that they could hire if they cut up all those folks.

Joe Casabona: That’s basically like Gumroad cut at this point.

Drew Dillon: So for apps that we integrate with that we can tell that have API’s around, Circle being one of them, we’ll have tools where you can just… We won’t automatically remove people yet. We’re still waiting to hear whether people want that. It’s a little harsh to just automatically boot somebody. But we’ll have tools where you can like hit the button and remove them from within the interface.

Other ones for Facebook groups, which effectively has no API for doing any of this kind of stuff, what we’ll do is we’ll maintain the list and we’ll build you a workflow that will say, Okay, this person has stopped paying, go remove them. We’ll send you an email when that turn event happens. You can go into Facebook, remove them, and then come back to us and hit that task saying, “Yes, I’ve removed that person.” So at least help you with the tracking and the workflow around removals of people.

Joe Casabona: Cool. That makes sense. Again, kind of based my big gripe about ConvertKit is maybe I just every month need to go in and see who’s tied to that product. I assume I could see who’s still paying. I assume I can at least see that.

Drew Dillon: One hopes.

Joe Casabona: Yeah, one hopes. And so then maybe it’s like, you know, okay, maybe they’ll get like two extra episodes of the feed before I boot them from the feed or whatever. Again, I think, like you said, you know, you have a community of 100 people and there’s a handful of people, especially I’m charging five bucks a month. So if it’s like 10 out of 100 people who didn’t pay and it’s a 50 bucks and then if they’re adding value, maybe that’s fine, too, still. Cool.

I really feel like I’ve gotten a little transformation in this conversation, which is great. That’s what I hope for. I want to leave the listeners with this, which is, if they want to get started today and they’re starting absolutely from zero, what is the first step you think that they should take to start their journey to building a community?

Drew Dillon: Step one is forming hypothesis of who your prospective members are, and why they’re gonna want to come together. That’s step one. And then beyond that, asking questions in such a way that doesn’t force that on people, but try and get them to say that back to you, and you can identify folks in that audience. So that very first moment of discovery.

Joe Casabona: Absolutely.

Drew Dillon: We could share this too. I’ve got a blog post about this and a Notion template for actually going through that discovery process.

Joe Casabona: Oh, nice. Yeah. I’ll put that in the show notes. All the show notes will be over at This is Episode 299. So be sure to subscribe, and stick around for episode 300 because I assume I’m going to do something really nice that I haven’t thought about yet. So stick around if I deliver, or if I just fail and fall on my face. Either way, that’s good content. I’ll definitely link that in the show notes. And that’s great.

And then based on your hypothesis, I would assume you go to a place where those people are hanging out, right? If it’s Twitter, if Twitter is still alive by the time this episode comes out, or one of the bajillion Mastodon servers or whatever and you start kind of asking questions and building a following that way, right?

Drew Dillon: Yeah, yeah. From that, I was starting with the idea that you already had some kind of audience already on our newsletter or Twitter following of some kind. But yeah, that’s the next step is where to identify those folks, bring them together. And who are going to be your first few members that are gonna be really excited to use, I think?

Joe Casabona: I guess, really that’s like step zero is before you even think about building a community, make a name for yourself. You can’t just show up and be like, “Hey, I’m gonna make a community. Let’s do this.”

Drew Dillon: If I started a YouTube course, nobody would listen to me. And they shouldn’t listen to me. I have no idea what I’m doing.

Joe Casabona: Awesome. Well, Drew, this has been great. Stick around for How I Built It Pro. We’re going to talk about Gumroad because as we record this, the Gumroad news just broke, and Twitter because Twitter seems to be on a bit of a downward spiral. But I think people are sticking around there because of the community. So we’ll talk about all that in How I Built It Pro. You can sign up in the show notes over at Drew, if people want to learn more about you, where can they find you?

Drew Dillon: They can find me on Twitter. It’s @Drewdil. Drew Dill is my Twitter name. It’s also the same on LinkedIn. I’m starting to run out of spaces to connect people to with all these social sites. Go to That’s the company site. I am usually the person who answers the support emails. So you can find me there as well.

Joe Casabona: Nice. Always remember to be polite in your support requests, friends. I’ll share a little trade secret which is a call back to an old format of this show where I always asked every guest what their trade secret was. When enough people kept saying I already gave it to you and I’m like, “I’ll stop asking.” I’m like asking the right question to get the best.

But a little trade secret is is a great service. It’s a short link service. It’s an AppSumo deal I actually use. And they allow for a custom domain and a little landing page where you can add social buttons. So you can go to And it’s like all of my social links. That’s right where I’ve been sending people. That’s the link I used to try to get banned on Twitter for the six hours that you weren’t allowed to post other social links. Sadly, I didn’t get banned, though.

All right, well, Drew, thanks so much for your time. I really appreciate you joining us today.

Drew Dillon: Thank you, Joe. Thank you, everyone, for listening.

Joe Casabona: Thank you. Of course, thanks so much for listening. Thanks to our sponsors for this episode, Ahrefs, Paid Memberships Pro, and LearnDash. Be sure to check them out. You can find them and everything we talked about in the show notes over at And if you are a pro member, be sure to stick around. It’s gonna be a lot of fun. If you’re not, sign up. And until next time, get out there and build something.

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