Pushing Boulders

# Brian Casel - Zip Message

**Chris:** All right. I'm here with Brian castle and we are going to talk about zip message.

I haven't listened to you on your podcast for years now. I think this is one of those things where I feel like I know you, but you have no idea who I am.

**Brian:** I've seen you around the Twitters and, and, uh, well now at least I see the bottom half of your face,

**Chris:** so that's right.

That's helpful. That's a decade old plus Twitter avatar. So I feel like I can't actually change it. It's almost a brand at this point, which is, that's how I jokingly referred to it with like, with Fred's, but I

**Brian:** could probably do. I've been updating my Twitter photo, like once every like year and a half, two years lately.

And basically because like every time I do like, I'm grayer than I need to like, keep up with the current level of gray hair that I'm seeing on my

**Chris:** hair. Yeah. Once I had kids. So it was just like gray. . my oldest is four. I have pictures of me when he was newborn and my hair is dark, I look like young.

Everything is nice. And then I, four years later I was just like wrinkled Haggard. I have all this gray hair look tired. Let's actually talk about something other than me complaining about my kids, which is a theme so far in the episodes here.

**Brian:** Oh, I can get to my kids too.

**Chris:** Right.

Okay. So, , let's talk about zip message. You have a bunch of businesses before. Just, I happen to know from listening to other podcasts that you are on. So, so let's actually start talking, is that message though, because that's your newest thing. And I think it's kind of really interesting because I think while primarily, because I don't know, is it your first real SAS or I guess it's the one you've focused on the most?

**Brian:** No, it's not the first SAS that I've done. , but it's, it of all the SAS products that are, you know, attempts if you will. So some of them were more successful than others, but, um, this one definitely has the most traction, the fastest than any of the previous, previous ones that I've done. But in terms of SA I mean, you know, people sort of, who've been following my, my products over . The years.

, you know, people probably look, you know, know most of like the productized service stuff that, that I've done. Um, I had a course on that and I ran a productized service called audience ops for about seven years. Uh, and I saw. Uh, recently I sold a bunch of products recently. , one of the products that I did sell was also a SAS, uh, called, called process kit.

Uh, I worked on that for about, , almost three years and I just sold that in, uh, uh, in January of 22. , but then going back many years, , my first real business that I like bootstrapped and then sold was called restaurant engine. , and that was pretty much a SAS. It had a service component, but we were, it was like a website hosting website, , builder for the restaurant industry.

And I worked on that for about four . Years. , but I, that was more that was built on top of WordPress with a lot of custom code. , yeah, but th the more recent, so I would say I started really getting into building SAS products, um, starting in 20 16, 20 17. And at that point, I, um, I, I outsourced the backend development.

I've always been a front end designer, front-end . Developer, , outsourced the backend. And the first of those attempts really failed. I spent a ton of money hiring these developers for like two years. Got frustrated with that. And then I spent the year of 2018 learning Ruby on rails and getting into just wanting to, to build my own app ideas from start to finish, you know, full stack.

, and then I, I built a few sort of practice ones, but still launched them. And then process kit was a bigger one. Grew that a little bit too, to the point where I could, I, I kind of got frustrated with it and then I sold it and then zip message started, um, right at the end of 2020. And, uh, that's what I'm doing now.

**Chris:** Cool. What was that journey to learn rails? Like I think you said you did re. Yeah, I think I say ask that because I remember you trying, I think I remember you talking about trying to decide between maybe Laravel and rails. Do I have that right?

**Brian:** Yeah. , so this was early 2018. I had basically just shut down a SAS product that I was working on with those outsourced developers for the past two years.

And it was that product was built on Laravel and it used Vue JS. And I didn't know that at all. Like I, I knew it was built with those, but I didn't know how to work with that. I had to outsource it. , uh, coming out of that, I, I knew that I wanted to choose, like I spent about a month sort of like exploring different, uh, frameworks and different languages to, to really dive into and PHP Laravel was my first thought was like, you know, I have experience with PHP.

I've seen Laravel before I've worked a ton with, with WordPress and custom plugins and stuff. , so try that I did about a month of like courses, uh, on, on Laravel and I was able to follow the coursework, but I still had a hard time, , building a new idea of my own based on what I learned for the past month.

So I then did another month of doing the same thing, but with rails, I did like, uh, you know, learn rails in a month kind of course, like one-on-one super basic. And I followed that course as well, but some something about the way that Ruby and rails works, it just clicked better in my mind. And it was easier for me to actually build a simple idea based on what I've now know.

And then, and then I spent the rest of the year, you know, going through many more courses and working with mentors and lots of practice projects and just really dedicated that whole year. Like literally all of my. , to learning Ruby on rails. And I, and I love it. I use it to this day. Um, it, it just clicks for me.

It, I could build stuff and I mean, I chose that, you know, it, even in 2018, it was no longer the, the hottest, coolest thing to, to use rails. Like, you know, people have moved on to react and, and all the, all the new and Vue JS and, and all, all the . New stuff. , I did not want to do that. I wanted to stick with the worldwide, like popular, uh, mature framework.

Like not something that's going to come and go. , but also something that was fast to build stuff and easy, uh, to, to design and build it and ship products. You know, I'm not trying to learn something so that I can be like a career developer at a company I'm a founder. I just want to build products and what's.

Simple fastest way to do that. , I found rails to do that, you know? Yeah.

**Chris:** I think as someone who's made a transition from developer, , to someone who tries to write code that makes myself money, like the, the mental place you put yourself definitely changes. Um, definitely because I remembered like, oh, there's this almost a meme of developers going through their, I dunno, lifecycle process of learning development, where you end up learning the proper way to do things and you go way too far with that and you go overboard and then you kind of scaled back to become kind of more senior, but the transition to being kind of like a founder or just someone who makes stuff then makes stuff that hopefully actually makes you an income or just some kind of revenue is for me, at least just definitely, , a shift in mindset or it's definitely more like, get it done type code.

And like, it doesn't mean the code is bad. It just means like, You're not going to sit there and ponder the implications of writing code like this and how that affects the team and the features that they were. It's just more like the features done, get something working.

**Brian:** Yeah, totally. I, I mean, I, I think that year of 2018 was the best career move I've I've ever done.

, just the decision to learn the full stack and, and, and expand my, like, I, wasn't a new developer. I had always done front end, HTML CSS. My, my whole career, , felt pretty confident with that. But, , being able to build any idea of quickly and then, and then make those like business decisions in, in the architecture of the app.

So like what's the fastest way to ship this feature, , and still, and still make it great and design it the right way with the future in mind and where, where the product roadmap is going. I can take on. Factors into how we actually design and build our, our software. And that's, that's so empowering. I mean, um, and I, I work with a couple of developers now and, and I'm in the code everyday still.

, so between me and like, they, they have much more backend experience and I can help architect and plan how we're going to design our software. , and then I do a lot of feature development on the, on the easier stuff to, to just build and ship and rails. So, right. Uh, it's a, it's a real, like, I'm way faster and more efficient now with shipping than I was earlier when I had to rely on outsourcing and maybe not make all the best architectural decisions because I didn't fully understand them back then, you know?

**Chris:** Right. Yeah. I'm just standing. That seems so maybe it's on the tentative. I don't know if it's unintuitive, but it seems important for sure. Potentially, especially, you know, for a developer of software

**Brian:** focused. I mean, like, like just for example, so going back to like 2016, , I was starting. Uh, SAS idea that that . Basically failed.

Um, I called it ops calendar and it was like a content calendar kind of . Tool. , and I, I, I designed the whole front end myself. I did all the, all the front end markup and code for myself, but I outsourced the backend. The developers chose to do, to do it in Laravel and Vue JS. And I didn't know what that I had heard of.

Laravel I did not, I have not heard of you before. I think at that point it was like version one. , and they built the whole app, like basically as an spa, you know, single, single page application. And I, I, again like my ignorance of software design at that point, like I did not really understand what that meant, but it had a huge application for how that software ended up being designed and built.

, like I designed it, but I did not design it, intending for it to be an. But my developers made that technical decision without me, because I did not, it didn't occur to me. I didn't know to think about it. Um, and that, and that turned out to like, cause lots of problems just a year and a half later when like view upgraded from one to two and broke everything and every single feature, you know, we had to rebuild the feature took forever.

Cause like they designed it as a huge spa with all this fancy JavaScript and you know, like coming out of that after I learned rails, like every, you know, I tend to be like not, you know, like a anti spa kind of designer because not everything has to be in spa, you know? , and, and like, and using these like heavy-handed frameworks, like I just don't see the point until you really need it.

You know, like there's a lot of functions. You can do a lot of really great things using, you know, Remote forms. And I use a lot of stimulus JS. Anyway, we're getting into the weeds here, but

**Chris:** no worries. I think people, people know, , I'm in complete agreement and have lots of opinions about this. I don't really want to focus the whole podcast on my own rant about they say the exact same things.

, one thing I, one thing you said that has stayed in my mind is how has it messaged felt like I had a lot more momentum. , if you heard Justin Jackson, how he talks about, , just getting momentum in the market, you choose, like, it felt like it was that kind of thing for you. Is that sound right? Like, I think you don't really talk numbers on the MMR if I remember.

Right. But I'm wondering what it felt like versus other things you've done.

**Brian:** Yeah. I mean, I talked to Justin a bunch and I've, he's been really banging on that drum of like, you know, find a wave and, and ride it. Of course, you know, that, that might sound like, oh, you gotta get lucky, but I don't think it's necessarily luck.

I think. I think it's being, I think it's observing the market, observing customer behavior, observing trends and, and just being in it. , over, over many years, you know, it took him many years to land on transistor. It took me many years to land on zip message, you know? , and, and at the time, I mean, does it mess, it started as like a shiny object syndrome, uh, idea for me, , kind of scratch my own itch.

But once I, once I made the, once I start started to get serious about like, I should actually build this and pursue it as a business. You know, I went through my whole process of like, yeah, I want this to exist, but is this a good business idea to do? And the reason why I said yes to go ahead with it, one of the main ones was because I saw in the market that video messaging tools are becoming more and more popular.

You know, , people are, obviously everyone is working remotely. But people are really embracing remote and, and the way that they communicate remotely in a whole new level than they have in the past. , so that, you know, again, like these are little factors that show like larger trends that are moving in the right direction and this, this tool just rides right into that.

And, and I think it's, you know, it's, I w I wouldn't necessarily call it a rocket ship, , startup or anything, but it doesn't have more traction. And, , more people from like a wider spectrum of people use cases and industries, , seem to resonate with it and pick it up and use it much faster than other tools that I've done in the past.

You know?

**Chris:** Cool. It is kind of a pro-sumer ish type tool, I guess. So, do you agree

**Brian:** with that? I think for some users, it is, , like there are, there are some freelancers and stuff who sort of use it, but there are definitely companies who use it, uh, quite a bit as well as, as a business communications tool. So, , a lot of teams who are remote, they use it to, to have entire meetings conversation.

Like that's the whole thing with zip message is that it's, it really replaces a lot of meetings, a lot of zoom calls, instead of getting people together on a live call, send the same video message to them. They can, the difference is that messages that they can actually reply back to you on the same, a single threaded conversation.

, and the other thing about it is that you can send it to anyone. You can send it to a customer or a client or somebody that you might hire and they don't need to download or install or anything. They can just click your link and hit, hit, record and record a response. Video screen audio, only text attachments, and just go back and forth on a conversational page.

Like that's, that's what has really resonated with people because there are other video recording, like video messaging tools. I mean, loom is the big one that everyone knows, but like that's a one directional single message, single URL that you're going to send to someone, is it messaged? Lets you do that.

But then you can actually continue the conversation. And you know, in many cases actually replace a meeting, replace a calendar booking, you know?

**Chris:** Right. And thank you for actually explaining what it is. Cause I realized I did a terrible job. Did not have you do that. Um, pricing. I have very selfish reasons for asking about how just doing my own stuff also about how you decided to price it message.

**Brian:** So today is that message uses a freemium model. So we have a free plan that anyone can use for as long as they want. , it has some limitations, but you can record unlimited messages. , you can, uh, you can share it with unlimited people, unlimited guests and, and have those conversations as you know, , uh, but then we have a basic tier, , and then we have a premium tier and, um, and you know, we don't, uh, limit the total number of, of recording minutes or anything like that.

You, you always have unlimited there. , the free plan that just the, each recording can only be one minute long, but, , once you upgrade to the paid plans, you lift that limit. The other thing that we, we, we, we give you a bunch of things in the, in the paid plan. So like you can customize or personalize your, your link.

So if I sum mine, like if anybody wants to send me an, uh, uh, a video message, you can do that@zipmessage.com slash. You know, you can get your own name, your own brand name, um, and a bunch of other things that are, you know, uh, but that that's, that's how it works. Now started that freemium model in October or November of 2021.

, before that, for like the first seven or eight months of that message, it was a more traditional, like 14 day free trial. , but then I introduced

**Chris:** when he made that change.

**Brian:** Uh, I did, I, I was a little nervous about it. I, I usually don't default to, to a freemium play, but for this type of product, I thought it made a lot of sense.

, you know, it has grown definitely since then. , I mean, freemium, I think helped, but there, there were other factors where I did a product hunt launch and, and other, , publicity stuff that, that helped it grow. But definitely I. I was a little surprised by and pleasantly surprised was people still upgrade pretty quickly after starting on the free plan.

I was, I thought that going with freemium, they would stick on the free plan for a long time before upgrading. , but there's multiple triggers that would cause somebody to upgrade and people go for it, you know, every single day. So,

**Chris:** yeah, that's actually something I'm doing with my own app where I want to change prices, where it has a lower, it has a free tier already, and then I'm going to make a lower tier.

Then I travel a bunch of trip wires they could hit to upgrade. So that part resonates because that's kind of like what I'm planning on doing. Like, um, did you think about that ahead of time or do they just kind of come naturally, but the tripwire points where you think they would cost them to upgrade?

Like, do you to put a lot of thought into that or was that kind of

**Brian:** like something that and . Thought into it? , I, so some things were like obvious. , , I thought, uh, I gave a bit of thought about the. The limit on recording, um, for free users. And, uh, at least for now, I I've started it off at, at probably the most aggressive that we would do, which is limited to one minute.

, most people don't seem to have an issue with that. , some people do upgrade to get a longer length of time, but, , there's other, I mean, the other, the other thing that people upgrade for is if you are going to invite team members to, if you're, if you're a team and there, and your team members are going to like manage conversations with you and your company's account, you know, they'll, they'll go to the premium tier for that.

Um, uh, yeah, a couple other benefits. And the other thing that we limit is, um, based on message history. So in the free plan, your messages stick around for 30 days and the basic plan they stick around for 90 days and then a premium, they stick around unlimited, uh, So

**Chris:** Okay. This is sort of a tactical question, but do you have a lot of costs in terms of like bandwidth and saving videos and that kind of thing?

**Brian:** Yeah. That, that also played into, uh, how, you know, thinking about pricing and, and what we, what we should give away on the free plan. Cause we, we do have real costs on video storage, video transcoding, and video processing. We also do things like, um, we offer, uh, automatic transcriptions of, of videos of what you say on the videos is transcribed.

That's only on the paid plan cause that, that also adds to our cost. , but it's kind of cool because we, you know, you can search all of your conversations, all of your messages and you can search for things that were said, because we transcribe them and we can search . The transcripts and everything.

We, we do a lot of work to like track usage and, and, uh, calculate, you know, average cost per account and everything, and, um, still, still profitable.

**Chris:** Right? Yeah. I was wondering how scary that was. I know bandwidth, especially can be kind of scary depending on where you're hosting it and what tactics you used, like cash videos, if you have that available to you and that kind of thing.

**Brian:** Yeah. We, we have done a lot of work with, you know, on the technical side, uh, what happens sort of like under the hood, uh, with, does it message to not only optimize like storage, but just to, just to make it a fast experience for, for, you know, so we'll w we we've built custom stuff around, like, as you record a 10 minute video, we're, we're uploading in the background while, while you're still recording.

So that it's fast when you, when you finish up and stuff like that,

**Chris:** This is the part about podcasting, where I, I want to actually just have a totally natural conversation, but then I actually have to think about other stuff too.

**Brian:** I know it, yeah. Interviewing is a lot harder than people realize, you know?

**Chris:** Yeah. I really like my favorite podcast where people just kind of just talking just totally interview style

**Brian:** or really, yeah,

**Chris:** me too.

Maybe I'll find a co-host someday, but I still like this kind of like learning about everyone's.

**Brian:** Yeah. I mean, I, I was saying I am starting up a new podcast right now. , it should be launching pretty soon. Uh, and it's pretty much like this it's like conversations with folks. And, , one of the things that I'm nervous about with it is, is that like, I don't want, I don't want to get burnt out on, on interviewing, you know, a hundred different guests in, in a year.

So I'll probably just say. Interviewing the same people, like, uh, like a rotation of 10 to 15, the exact same idea, you know, friends to just come back on and, and do you have, and I just want to talk about different topics with different people, you know, like yeah. , there's, there's plenty to talk about, you know,

**Chris:** how did you and Jordan start your podcast?

How'd you guys meet?

**Brian:** Yeah, that's sort of a funny story. , we met a few years before we started the podcast. Um, we were in a mastermind group together, but the way that that came about was, uh, Andrew Warner on Mixergy put like, this is, this must've been back in 20, I don't know, 2013, something like that. Um, maybe 2012 is when we started that, that group.

, he, Andrew Warner did this, like mix this like mastermind matching thing as like an experiment and Jordan and I both submitted our names and we got matched up and into a group. We were in this mastermind for like two, two and a half years. And the funny thing is that like it, we, we joined up and I just met Jordan for the first time through this mastermind group turns out he and I live in neighboring towns in Connecticut.

, so like the next week we, we, we met up for coffee and it's like, totally cool. Like we met through Mixergy on the internet and we ended up living five minutes away from each other. And it turns out that Jordan and I both grew up in long island, New York in towns that are like 10 minutes away from each other.

We didn't know each other back then. But like, and then somehow we ended up on a podcast together.

**Chris:** Right. That's really funny. I had no idea. You guys live so close together. I should mention, , your podcast is Bootstrapped Web, right? Yep. Yep. Keep trying to say bootstrap.fm, but that is a different podcast, right?

I don't think Ian records that anymore.

**Brian:** No, but he, um, he gave it over, um, oh man, now I'm blanking. And I was just on, on the show, uh, last week, , which I, I thought that was really cool of Ian and Aundrey when they, um, when they, , they, they, they handed it over to like, keep the podcast alive, even, even when they were done doing it.

**Chris:** So, right. That was one of my favorite people. Just, just talking podcasts in addition to, um, do you remember, do you ever listen to Bootsrapped with Kids? Yes.

**Brian:** Yeah. I'm good friends with both those guys, Brett and Scott today.

**Chris:** I'm actually talking about you that somebody asked them.

**Brian:** Yeah. Yeah. They're in a group of us.

We get together and go skiing and snowboarding. Um, uh, every year I do one in Vermont and one in, uh, in Colorado and Brett goes out to that. Yeah.

**Chris:** Right. , okay. I have a note to ask you about, uh, what you're doing from marketing and zip message. Do I remember right? You might hire for marketing. I'm wondering kind of how you're thinking about that.

**Brian:** Oh yeah. This is hard. Um, I have hired I've I've had a hard time, frankly, hiring people to help with marketing. , and I've been trying to hire for that over the past year. , my first thought was I wanted to hire like, uh, a general marketing person to help with all things marketing. It would probably start on like a part-time retainer and grow into, uh, maybe a full-time role, be one of the early key employees.

Like that was my vision for . This role. , you know, cause I want to be on product most of the time and I, I like talking to customers, but there's a lot of marketing work. Um, whether it's coming. Campaign experiments and tracking the numbers and, and, um, you know, keeping track of, of SEO and running experiments and doing all this stuff.

, I wanted somebody to sort of like drive that, that train. And I ended up finding that there, there are many, there are many people who are pretty good writers, , or they're really great at PPC or, or they have some strength and they have, uh, they've dabbled in, in all the other marketing things, but, you know, it's hard to find a generalist and I should have learned that sooner.

Um, and, um, and so now,

**Chris:** yeah,

**Brian:** it, that's, that's the tough thing about it when you're talking about marketing, , because for somebody to really have like the strategic vision and the position. They've gotta be really invested in, in the product. And at that point, especially for a very young startup, like, I think it's gotta be like a founder level sort of thing.

And so that's, that's sort of where I am today. Um, I've, I've basically taken over that role of like head marketing strategist, but I do hire people who are specialists in what they do. So, you know, I, I've developed a bit of content. I'm going to be doing more, I've hired a writer to, to help develop articles and, and she's a fantastic writer.

, right now I'm sort of looking for somebody to help on the SEO side. , like I've dabbled in these things before. Uh, but it's not a part of the business that I enjoy doing . Very much. Um, but, , you know, I'm actually looking for like a SEO, uh, like a technical SEO specialist to help with keyword . Research and, and, um, and you know, content, uh, roadmaps and things like that.

Yeah. Um, uh, But then, you know, then I'm, I'm now looking at other things like sponsorships, you know, maybe podcast and newsletter sponsorships. But then, then there's things that I'm doing on the product side that, you know, cause it message it again, it's a freemium model. So, so it's what they call it.

Product led growth, right? Like we do see people sign up share, is it message. And then that person signs up and they, they shares that message. So I do a lot of work in the product to make that a really smooth process to like onboard and then share and, and, you know, um, work on that viral loop. , and then the other thing that I'm getting into now is integrations.

Uh, so I'm talking to other other products, um, where it makes sense for video messaging to be synced up or embedded or connected in some way. And there's a lot of tools that our customers do use, uh, in conjunction with that message. So, , You know, I'm starting to, uh, actually work with some products right now and develop more integration partnerships.

**Chris:** Um, do you see that like a lot of support type companies, that's the first use case that comes to mind for me, like

**Brian:** help desks, uh, apps are one and we're working on, , on some integrations there and then there's a number of other categories. So another big one are like membership platforms. Uh, we get a lot of like coaches and course creators who use zip message to communicate with their students.

Um, so, so connecting, you know, like private or semi-private group conversations or one-on-one conversations with their member portal and things like that. , we get podcasters who are using zip message for a few different things. Like one is as like a . Listener inbox, , to send messages. Another people are actually using zip message to record podcast content asynchronous.

, which is really interesting and I'm doing some of that on my new podcast as well. Um, uh, CMS is so, so you can embed zip message on any website. We give you like an I-frame embed code. , so that works today, but you know, we'll, we'll probably come out with like a WordPress plugin to make that easier, maybe like a web flow integration and stuff like that.

, and then the other one is actually calendar bookings. Like, is it messages sort of like the opposite of calendar bookings, because it's like, you can either get on a live call or you can do the call asynchronous by sharing your zip message link. Um, but what I found is zip messages great for like that follow-up conversation that happens after.

So let's say you're, you're interviewing a freelancer to maybe hire them for something 10 or 15 minute zoom call to meet and greet and see if there's like a, if you gel with your personality and if there are good. And then you're going to have like 20 follow-up questions where you really dig in to, to what you're, what you might work on together.

And that's, that's where it's perfect to do is to use zip message to go asynchronously. I mean, they can share their screen, they can show what they've worked on. They can answer your questions. It can be, I I've done this with people living in like Australia, you know, totally different time zone. Um, but, but we can have full like face-to-face conversations that just last three or four days instead of both of us having to get on at

**Chris:** some crazy hour.

Right. Yeah. I've had that experience with, I'm doing customer support for Australian customers. Always interesting.

**Brian:** Yeah, for sure. Yeah. Neat.

**Chris:** , I wanted to circle back on the marketing thing. It sounded like a lot of it, and I imagine kind of based on your history, , a lot of your ideas are that are based on content marketing, but I don't know if that's kind of what you're focused on before.

I mean, obviously you have the built-in stuff like the viral component to the application and all that stuff is marketing, but I don't know what you were thinking about for tactics.

**Brian:** We just sort of just began really investing in content, , for zip message. Like we just came out with a, uh, a new guide all about how to combat zoom fatigue, which is a real thing.

, so we did a really great guide on, on that, uh, which obviously makes sense for, for zip message. Cause we're, we're, the solution does even fatigue use it message. , so we're going to come out with more guides like, like that. , but probably not going to do like tons and tons of content. I think it's better to do a few very high quality, , guides and, and really positioned them well.

I mean, also just working on our website itself with like highlighting key use cases and case studies and comparisons us versus alternatives and things like that. , so just trying to develop a lot of that, that kind of stuff.

**Chris:** So right now, is that a lot of freelance work to get marketing stuff done?

Or, or what are you doing? Is it all?

**Brian:** Yeah, it's, um, it's like a combination of me working on the strategy and the direction, and then hiring a freelancer. Like if I'm going to do a, like, if we're going to do a big article, the zoom fatigue guide was written by a writer, Claire Emerson. Uh, she's really great.

And, , but I gave a lot of input in terms of the direction and re you know, reviewing it and making sure the positioning is right and all that. Um, and, uh, yeah. And then, I mean, I am doing this other podcast, like I mentioned, it's, it's sort of my personal thing where I just get to talk to other people I want to have conversations with.

Um, but it is going to have like a zip message ad, you know, tacked onto it. So there's that too,

**Chris:** right? , I can see, I have a lot of experience with freelancers left too much more than I do for, I mean, I've been mostly just like working at a job, but I also have my side stuff, which has been courses mostly.

And then also . This new SaaS I have, um, or it's not that new, but I'm working . On it more now than before so the first person I've ever actually really hired to help it's a freelance and it's actually been really nice to help with the development, which is normally what I would do being a developer.

But I actually haven't really found it totally useful to have someone to do that part for me, especially because I have to spend most of my time at the, during the day working in a job. So yeah.

**Brian:** I love what you're doing there because I, I came up as a freelancer for most of my self-employed career.

And for the early those early years, I was freelancing and trying to build a proper. Like when I was doing restaurant engine, that was the business where I transitioned out of freelancing into running my own SaaS. But the, um, that was really difficult because I had to like market myself as a freelancer to pay the bills.

And I always sort of looked back on that, like, I wish I sorta had a job. , back then there were a lot fewer remote jobs than there are today. , but you know, I think in a lot of ways, it would've been easier if I had a full-time job that I was giving my nine to five to, and then I can like reinvest all of the profits from the startup into the startup.

And even if it's just running nights and weekends, you know?

**Chris:** Yeah. My setup is interesting like that. So I work at UserScape so I actually worked with Ian. Oh, cool. Yeah. And I've worked there for eight years. It's been awhile. , there's a trade-off there is. We expected, we all have side projects, but it's encouraged and fine.

It doesn't try to own any of our IP or anything like that. So, yeah, it's actually a kind of a great setup, , which is why I've worked there for so long too. And then I also like do have always done courses and that kind of still supplements income a bit. , and then the current thing, I have Chipper CI it's a continuous integration app for layer Val developers.

And that is also making some money, not a lot, but enough to like kind of supplement and come a bit, but mostly just reinvest it because I can, which has been kind of helpful. So I've hired this person. They're really great. , they're on the expensive end, but I also have almost had to do zero kind of management of, of what they're doing because their work has just been so good.

And I think I got lucky with that because I've always been really afraid of like how to manage people effectively. I haven't, I sort of have done a little bit of that in my past, but not, not enough to really say anything.

**Brian:** I've done a lot of hiring and a lot of hiring freelancers. I've literally been doing it since 2008.

, I . Became a freelancer in 2008. I, I left, uh, an agency and, , pretty quickly, like within a year I started outsourcing parts of my freelance projects to other freelancers and, and for awhile, I w that's how I built up my businesses. I would get like larger and larger projects and then take on more of them and assemble little teams of freelancers designers, developers, , and then kind of fast forward to audience ops.

, that grew to, by the time I sold that business, it was a team of 25, , basically all freelancers, but they were all like daily part-time contractors. And, uh, but then, you know, and I just sold that business a few months ago and now it's like back to, , a much smaller operation, which feels good for me.

So it's, it's basically me plus now I have two developers, um, and they're in India. Um, uh, and plus a few of these marketing freelancers in different

**Chris:** places. Is that Indian setup working well at the time I remember you, right? There's like some contexts in the U S you kind of interface with, and then they manage the, the bully

**Brian:** in India.

Um, right. Uh, they're, they're really, they're actually an agency. And then, um, they assign, uh, now I have two people over there. , and they're, they're really great, you know, uh, for the most part they're working when I'm sleeping, but then I, I arranged with them to shift their hours by like two or three hours so that we have a bit of overlap, uh, when I wake up.

Um, and, um, and that's what.

**Chris:** Perfect. So do you like that cycle? I feel like that kind of works out. We can kind of give feedback during your work hours and then it's done overnight and then you come back. I mean, obviously there's a delay, but I don't know if that's mattered enough if that's and

**Brian:** it's perfect.

It's perfect. Yeah. I, I, uh, I have a good, like three hours in my working morning to, um, to, to either do like C get them live on, on slack and we can hammer out any final changes before they end their day. Um, but yeah. Then later in the day I'll be preparing stuff for, for what they're going to work on tonight.

Yeah. I mean, usually we have longer longer-term stuff that, that they're spending a week or more on, but like, but, but yeah, I get updates from them when I wake up and that's usually the first thing that I, that I work through in the morning.

**Chris:** Yeah. How do you communicate effectively with them? Like have you found you had to do change how you communicate there?

Cause I guess it's mostly written,

**Brian:** uh, it's mostly written there. They're really excellent with, uh, written English. , and. We communicate almost exclusively through GitHub issues, like really, really detailed, written get hub issues and get hub, uh, comments. , and then we also have slack and we, we chat in there and then we will use zip message to show things like here's, here's this bug that I'm seeing here in.

We'll use that to send videos back and forth. , don't do a lot. I do almost no live calls with them. I know other people like to do like stand-up calls and status updates and stuff like that. I've, I've always been very, very minimal on live meetings. I just, I don't like to be on many meetings. , and I don't find them very productive.

, and, and also like, I don't like it when key information is siloed in live meetings. Again, this is like a big reason why I built zip message is because. You can be on like an hour long zoom call with a client or, or your coworker. And you're hammering out some, some work together, some key creative decisions together.

But if that was discussed on a zoom call, it's, you're not going to, you have nothing to refer back to, even if you were, even if you recorded the thing, like, what are you going to do? Like scrub through an hour long recording to find the detail that that somebody said. I mean, that's, that's how details get missed or forgotten.

Right. , so I really like having what we discussed and the decisions we came to all written and logged in a thread in a GitHub issue. Or if it's with a marketing person, we have it usually with them, I'm communicating on zip masters. So we'll have like 20 or 30 back and forth on, on video, on audio message.

You can point right back to the, to the message where you have the key piece

**Chris:** of information. Yeah. That, and the transcription seems pretty neat. Cause I was just thinking of my own experience where kind of working at a place that was meeting heavy, it was like, if you weren't invited to the meeting, then you missed out on information.

If you're invited in, then every meeting, you don't get any work time because we got to meet exactly. You have all information, but can't act on it.

**Brian:** Exactly, exactly. And the other, and the thing that I, um, really have, I've seen this every single time, I have a zit message. Conversation asynchronously. And like the benefit of asynchronous is not just time zones or work hours.

Yes. You have more flexibility. Flexibility there. Yes. You, you get more time to actually do your work, but you actually end up contributing better responses in the conversation, right? Like if I'm going back and forth with someone on a video, back and forth, I have time to digest what they said. I have time to think about what.

Like just, just earlier this morning, I had a pretty, a pretty in-depth conversation with a customer on zip message, , giving feedback about our product and we've gone back and forth like 30 times now. , and I came back to him with like a 15 minute video, or at least like a 10 minute response, but I recorded it like twice.

I, I recorded it once and I was like, you know what? I could say that a little bit better. I could prepare my notes a little bit better. And then I got back to him with a much tighter response. And when we do that, both ways, we end up having a much more productive conversation because we're pushing the ball forward, you know, with, with better

**Chris:** responses.

That actually makes me want to try it out, to get customer feedback on my own thing, to start with like my own video and just say, here's your spot here? Um, which very much ties into my fear of actually talking to customers like a live one-on-one like a slack call or something.

**Brian:** Yeah. Um, , it's best to get over that fear, but I, I mean, I I've gotten, I've gotten lazy with it and at times, like sometimes I just get so buried in the product that I feel like too disconnected from, from customers, but in the very earliest days of, of the business, like I am hungry for more and more feedback and conversations.

Like that's what keeps me going, because it's like, it's like, um, you know, I, I just, I just need to know what their experiences with other tools with this tool where, what they're trying to do. , and then that's usually what, what makes me go back and design the next feature?

**Chris:** What's your preferred way to facilitate that right now?

Like how do you kind of, because I it's easy to cold email people, or I guess it's not cold cause they're your customers and they know kind of who you are or how does that work

**Brian:** with Zim message is really easy. Zip messages. Definitely my preferred way of communicating with customers. Because again, it's you get this high quality level of feedback where they they've taken time to prepare their, their notes, and then they actually recorded on video for you.

Um, and then we go back and forth many times.

**Chris:** Um, uh, do you think there's a higher bar of that? Does that make it harder to get people actually respond to you? Cause it's kind of hard to get people on a call or to get people to record themselves if they're not comfortable with

**Brian:** it? Well, I think it's actually less of a lower bar because I'm not asking them to book a call on our calendars.

Um, so it's less of an ask there. I mean, in, in my case, we're communicating on zip message about zip methods. So that, that makes it a little bit easier.

**Chris:** Um self-selecting

**Brian:** yeah, for sure. But, , but I know that, you know, plenty of agencies are using it to communicate with clients and they're finding it, uh, you know, a really great way to like avoid all these client calls, where again, it's really helpful to get like feedback from your client on a design that you've delivered and go back and forth asynchronously and have that, have those recordings to like refer back to, you know,

**Chris:** I'm going to give this a try. I have to try that with a message. Record a message. Please do

what. Okay. I'm going to do a thing. I might end up asking you questions about my thing, my business.

**Brian:** Yeah. I was actually just gonna, I was going to start to turn the tables on you. Cool.

**Chris:** Thank you. , okay. So what are you doing right now or hosting? And do you do any kind of like automated testing?

**Brian:** Yes. , well, we don't have an automated CIA tool, so we might be in . The market for that soon.

, the, um, but we do have extensive test coverage and in our . Code base, , uh, so we're, we're hosted . On Heroku. , and, uh, and we use our spec and

**Chris:** thanks. Thanks. And koroko has a thing to run tests before it deploys. I'm not really sure. I haven't used,

**Brian:** uh, previous SaaS. The one that I sold recently, uh, process kit was also on Heroku, also Ruby on rails, and we used get hubs act.

I think they call it actions. Yup. Um, we used that for the automated testing. Um, but we have not set that up yet on zip message, but I think we will at some point pretty soon, cause we, we already have several hundred, like many hundreds of, of tests written. Um, so it's it's uh, we, we, we covered it. So

**Chris:** I partially want to ask like a mom-test type question.

So I'm not going to be, I'm not prepared enough for that, but like, , I paying for chipper paying for CIA apps. Like some people do it and some people avoid it. I think like stay in because a lot of them have free tiers. Right. So get hub actions and then Bitbucket has their own thing. Get lab has their own thing.

And then there's other applications that are separate from where your actual code lives. Right? So Travis CIS circle for Louisville developers. I don't know how people feel about pricing with these because a lot of them price based on build minutes, you know what I mean? Like how many minutes you take, like, like even get hub does this, although they're free, Tara is pretty generous.

, and circle CI does a thing where it's a credit system. So if you have a larger server, you eat away more credits kind of quickly. I'm redoing pricing for chipper, but I'm leaning towards still kind of a more traditional tiered type thing. Cause I think that's just kind of a, that might be more of a layer of ELL friendly thing.

Cause that ecosystem is sometimes feels to me like, , like that might just work better for people versus like the unknown of a, of a pay per use kind of like an AWS thing where you're not necessarily exactly sure what your bill is going to be any, but you, you know, you have an idea.

**Brian:** I don't know. I dunno.

I mean, I'm, I'm not, again, I'm only just a couple of years into full stack development and even knowing what automated tests are. Um, so, uh, but of course now I am like obsessed with testing. Like every single feature we do, we're writing tests, right. It has made such an . Improvement in, um, reducing bugs and not having to rebuild features and stuff like that.

, but yeah, in terms of tools, I mean, we do readily pay for, for dev tools in . General, , like Heroku and, and a bunch of, you know, ad-ons within Heroku. Um, uh, you know, w w we also use, um, app signal for like error monitoring and stuff like . That. ,

**Chris:** you know, how much those all are per month roughly?

**Brian:** Uh, I think apps signal we're, I think we're on the, like the 50 a month tier or something like that.

Um, what else do we have? I mean, we pay for a ton of AWS stuff too, right?

**Chris:** The video stuff, I assume.

**Brian:** Yeah. Um, I'm just thinking about like other random tools that we have in there. Um,

**Chris:** right now, chipper is free freemium because, um, which was the decision I made a while ago because, uh, most CIA apps are just freemium.

And I think that makes sense for this type of app also, cause it kind of get your developers. Yeah.

**Brian:** I mean, I liked that the, that your app is in the pipeline. Um, you know, cause that like once people adopt it, they're not, they're not going to change unless there's a really strong reason to change if it's, you know, I think, I think the fact that we're on GitHub and the, and the fact that they have get hub actions, that that would make it difficult for, for me to decide, to use something other than get hub actions.

Right. Um, unless there's a really compelling reason to do that. Um, maybe there is, and I don't, I'm not familiar with it, but, um, I haven't really looked into it, but

**Chris:** yeah, they're definitely neat. , I think of a compelling case for chipper or the people who decided to pay for it or like that it's really pre-configured for Laravel.

So you don't have to care about setting up the stuff that makes it work. You just kind of like throw it up there and you run your tests, but it doesn't mean it's perfect. You still have to figure out your, like your environment variables and if you're testing it so database like sending that up, um, although we tried to make that as easy as possible and mostly do.

So I think that is kind of the compelling case . To use it. , but I wonder if that's just like a small segment of people who are interested in that versus people, especially developers who kind of like more complicated things. They like figuring out complicated stuff. You know, I, I sort of suspect that's a thing

**Brian:** my, I would wonder about, um, in terms of the business, like, I don't know that guys like me are going to be a, a good target customer because I mean, we, we ended up taking a little bit of funding, but I still operate like a, like a bootstrapper, you know, um, if there's a good enough tool, that's free.

Like I need a good reason to start paying for something else. But where I think it could make sense is if you target agencies, , who, who have, who like development agencies, right. , who are developing apps and maybe even maintaining apps for several clients. , so like there. One app is free, but if you need multiple apps for multiple clients with notifications and alerts to your clients and stuff like that, you know, , that's, uh, that seems worth paying for it, especially if it's, you know, I like the idea of selling to clients and selling to agencies, because usually they justify the tools that they, that they buy based on pairing it with revenue, right?

Like, , you know, like an audience ops. We had stuff that like, I, I spent a lot per client, but it, it was tied to the revenue that each client is sending us. So I didn't, it didn't feel like a cost of doing

**Chris:** business. Right? Yeah. Yeah. That's interesting. Right now, my plan is to do a cheaper tier. So right now it's zero or 49 bucks a month, or sorry, 39 bucks.

How do you get cheaper than you can get there's some expansion revenue

**Brian:** what's that? How do you get cheaper than, than zero? Like you pay people to use it.

**Chris:** It's like, there's no real viral element. Well, there is actually some parts I could do for that. Um, like if you support open source, you can get your, your little logo and stuff in on people's projects. So I guess in the element, like the free tear helps there. , but it is, it's not as much as like, as a message where people are just sending it out and there's a message.

Branding is like, you know what everyone sees when they're, when they're making a message, receiving a message and all that kind of stuff.

**Brian:** Yeah. So like the free doesn't really give you the benefit. Like the only reason I went freemium was because it's a marketing play really. It's like, I want people using it and sharing it so that it exposes it to more people and freemium was the best way to do that.

So I guess you don't really have the benefit of, , of, of like the viral app. But you're in a competitive market where there are free tools that you sort of have to offer some, some kind of free option.

**Chris:** Yeah. That's why I started with that. Yep. Yeah. The, the pricing I want to do is a cheaper tier and I've named it like a solo tier and solar developer type thing.

And then a team tier, which is kind of like the thing where I spent, I think a lot of people will be, it's like, it's going to go up from 39 bucks a month. And then I have some other bigger tiers. Like you can grow into a different tiers. And like finally, I actually have an unlimited tier, which is a bunch of more expensive.

So I'm curious to see if anyone goes into there, but that's

**Brian:** kind of, um, like what's the value metric? What, what is, what's the difference between the tiers?

**Chris:** So this is interesting and it also gets into some annoying things about competing with the free ones I have landed on. Well, okay. So I'll tell you how I broke it down.

Well, I'll start with that. The thing that I th that other CIA apps seem to care and value. What they're charging on is like build minutes, uh, how long you run builds and how big the server is that you're using, which kind of in my head aligns well with the value you're getting. Cause anytime you push up code to get, you know, it kicks off a job and it runs for a certain amount of minutes and it's faster or slower, depending on if there's more resources and that kind of thing.

Yeah. That pricing is annoying to me. I don't know how their developers kind of like it, but, um, but I do see the appeal of it because it aligns Woolf with your cost center, especially with that infrastructure heavy thing. Like I continue to see, is

**Brian:** it annoying because it's like you as a customer, it's a little unpredictable.

**Chris:** Yeah. I've never said anyone. I've never met anyone who like, I don't, I think in reality, people don't mind it too much, but

**Brian:** yeah. But I think in the case of CGI, like my, my limited experience with it. The Le the, the, the duration of time it takes to run. The whole test suite is pretty consistent. I mean, it's slowly grows over the, over time as the, as the test suite grows, but it's not like on Tuesday it took 30 minutes and on Thursday it took 96 minutes.

Like it, you wouldn't see that kind of, you know, um, you know, it wouldn't jump around on you. So in that, in that sense, it's like, it's just like for the next few months, we're probably on the a hundred minutes here. And then we might, we might inch up into the next year after that, but it's not going to be like sudden.

**Chris:** Yeah. And it depends who their customers are because a lot of their plans are like, you start 3000 minutes and then you buy chunks of 25,000 minutes at a time, depending on, that's like a, a circle CIS like that. What I've landed on is having a small or shrinking the free tier a bit. , so it used to be

and this is me copying other apps when the app was first made, when Chipper was first. You used to get unlimited builds. I'm sorry, not unlimited builts. You started with the limited builds until you got into a paid tier. Then it wasn't limited unlimited projects, unlimited team members, and I'm changing all of that.

, that's the main ones and some other stuff too, uh, like server size goes up as you get a higher tier also. So the free tier, I think we'll just have a very small number of private projects. So you can use like prop projects and within get help that are private, not public projects. And then that number goes up as you go up tiers.

So the solo tier just has, you know, also kind of a few, the team tier goes up a bunch, the other tiers go up a lot. So the main thing there is projects limiting, and then also the number of builds per month. So instead of doing a build minute thing where there's a usage base, it's just a number of builds.

People are using per month. And I actually have, you know, I have a few years of data of how many builds people actually do per month. So I can base that off

**Brian:** of, I was going to say like, are you able to see. I mean, like, what do the best paying customers look like? Right? Like how many buildings, how many minutes?

And also what types of businesses are they, what are they doing? Right.

**Chris:** One is almost definitely a agency because they have like 128 projects. And then the next highest team has 28 projects that like this one customer is doing exactly like PAGC thing.

**Brian:** They don't have 128

**Chris:** of their own products. I don't think so, based on what I can, I can look in and see the names of flair, re repost, and they all look fairly different.

, and what's interesting is some have a lot of projects and actually do run a lot of builds per month, but only some of those are, are doing the thing where you pay extra to get more concurrent builds. So otherwise you're waiting, you do one build at a time, but yeah. So if you have four projects and four developers code up pushup code for projects, you're waiting for each one of those.

So one at the time you can pay for extra concurrency. So you get concurrent builds. So they happen at the same time. So some companies do that and some, , but a lot of them don't and just kind of like, wait. Yeah. Which is an interesting aspect of that. , you know, and some people are deploying here and some people are just running tests and getting results.

So it's interesting to see who, who uses continuous integration to actually deploy from that pipeline versus just see if like tests are running, that kind of thing. , the,

**Brian:** I mean, it definitely makes sense to have all that stuff in paid tiers, right? Like concurrency multiple, multiple . Builds, multiple projects.

Um, you know,

**Chris:** I'm interested to see, I have to dig into what type of cus of, uh, of companies they are too. I haven't done enough of that. That's an interesting question.

**Brian:** Yeah. I mean, when I talk to customers, especially early on, like when I'm just researching a potential new product, I really like to ask things like, , tell me about the current CI tool you currently use.

How much do you pay for it? Um, you know, what were the factors in deciding on that? And like, I looked for like evidence of, you know, like the mom test stuff, right? Like, like evidence that you have that you're actively paying for it, or you have paid for it. Um, not like, would you pay for this idea sometime in the future kind of thing?

Yeah,

**Chris:** for sure. That makes sense. And the things that I can see are like, if you have invited team members, if you have notification channels. So . Like, if you actually are getting notified, if a build fails, right. , if you have a build step that has the word deployment, something

**Brian:** we did, when I had the CIA running through GitHub actions, we did use Zapier.

Put it to, to pipe it into slack, to tell us like, yup. It all ran or, or it failed. Um, so that

**Chris:** was useful for us. Right. That's interesting. I'm surprised.

**Brian:** And I paid for slack. I mean, I paid for not, not slack. We had free slack, but uh, paid for Zapier, you know?

**Chris:** Yep. That makes sense. Because the notification part is important.

You have to know kind of what happened. Otherwise you're checking your email for get hub action emails, which is the, I dunno, you know, email's not a great medium for that. So yeah, it's interesting. I had to figure out what kind of things the companies are doing. Like some of the companies I know of just from being in the Laravel community, but a lot of them and most of them who are paying I haven't heard of before.

Yeah, for sure. So, , Chipper has an interesting thing where it grew up to a few thousands of MRR kind of quickly when we launched in 2019. And then, um, me and my, uh, my friend, who I started it with David. Both me and him both started working less on it just cause we had stuff coming up. Like I had a kid soon after the second kid sued after it launched.

And he had, um, he was making more money doing other stuff. Like he Cobits lyrical Nova, which is like, uh, one of the first party admin panel things for Laravel. So we kind of let it just slide and then it just, the revenue grew a little bit, but like the churn was slow, which was really nice. , so we don't lose revenue really, but it just kind of floated for like a year.

So, um, I brought out his half of it. So this year as of this year, January 1st, I own all of it. So now I have congrat interest in thanks and, um, and doing more with it. So I'm trying to grow it. It's grown a little bit since I've been doing more like tweeting, emailing, adding features and that kind of thing.

**Brian:** It's a great foundation to build. I think that the thing with developers as a market, , and I don't sell a lot of my customers probably are developers, but it's not like I'm selling exclusively to developers. Uh, But from what I can tell the, my, my friends who have developer centric products, you know, I look, I look at like Adam Wathan, you know, Ben Orenstein, , you know, built tubal and Adam with the tailwind.

Um, yeah, marketing is so hard because it's, I feel like marketing is easy and hard for when you're targeting developers. Right? Like you can't do most of the typical like marketing tactics because developers hate marketing. , but the, the nice thing about going to developers is that like, there's a ton of them.

There's, there's, it's a always growing market. And, , and like, I think you can do just cool, fun things. Like you're, you're doing courses, right? Like. Uh, you know, you're, you're teaching developers. So, I mean, that's another thing like, like, um, you know, Chris Oliver who runs go rails.com, um, which is one of the best, I've been a customer of his for ever since I've been learning rails.

, that's a, it's a fantastic like training membership community with his video tutorials and stuff, but he also has dev tools that he sells to, to rails developers. Right. How do they know about those tools while they're linked? And he talks about them in his and his tutorial videos, right? Cause he has this huge audience.

, I think like audience driven stuff tends to work really well when you're selling to developers. Right. I mean, Adam with he's got a massive following and that that's helped talent. Um, you know, and, and Ben has been podcasting forever. So like, uh, not, not to take anything away from their products. I'm a huge fan of both of them.

Um, Uh, I use those products every day , well,

**Chris:** it's the combination that works like, you know, they have the audience and obviously there are very smart people doing very good work.

**Brian:** Yeah. Yep. So I, I mean, I, I, and you already have that going for you too. So like, I would probably probably lean into that, you know, um, don't really need to kind of reinvent the wheel.

Yeah.

**Chris:** Cool. All right. We are a little over an hour, so that seems like a good time to wrap up. Cool. , where can people find you? Do you have a name for your new podcast? Do you want to talk about that

**Brian:** yet? Yeah. I mean, it's, it's called open threads. Um, I don't know exactly when it's going to launch. I hope sometime in April, , Uh, I have recorded a bunch of episodes, but they're just not out yet, but yeah, that that'll be called open threads.

It will be somewhat similar to this, you know, conversations. Uh, and, um, and then Bootstrapped Web is the one I host with Jordan on the weeks when he and I are not traveling and doing other stuff. , I'm @casjam on Twitter. That's, that's where I spend most of my time. And of course, uh, zipmessage.com is my product.

**Chris:** All right. Cool. Well, thanks for coming

**Brian:** by. Yeah, thanks for having me, Chris.

,