The Business of Laravel

Matt Stauffer:
Hey, welcome back to the Business of Laravel podcast with our talk to business leaders who are working in and with Laravel. My guest today is again, the guest we had for episode one of this podcast, the inaugural guest and he's, look at that. He's got the mug. I guess that's the first time we had a chance for this because you're our first repeat. I love that. Wow. You really, you really did that. Ian's Landsman, Ian Landsman, the godfather of Laravel. And when we first had you on, actually, sorry, Ian, hi. Thanks for coming on.

Ian Landsman:
I got the mug. Yeah.

I'm ready.

Ian Landsman:
Hello. No problem. It's always fun to be here.

Matt Stauffer:
That's great having you. So when we first had you on, we were doing the classic business of Laravel. And that's what we've done for every guest up until now. It's just like, you know, tell me about your backstory and tell about your business and how is your business connected to Laravel. But we were talking just a couple of days ago and I said, Hey, I am catching up on your wonderful podcast, Mostly Technical. If you don't listen to it, y'all, I would highly recommend checking out mostly technical. It's one of the most fun, casual friends with, you know, like talking about tech, but talking about life. Like I feel like it's just buddy. That's not a buddy comedy, but you know, like it's, got all those good bits. It's a great podcast. I was like, I'm catching on your podcast since the summer. And I heard this episode where you talked about this new idea that you have, Outro.fm. And I was like, I think I'm the target market for this. Are you still working on this? me, and you're like, you know what, let's just talk about the podcast. I know less than any of the mostly technical regular listeners. And yet I think I'm your perfect target audience. So I wanted to see, would you just kind of give a pitch for us for what is this project? What motivated you going to it? Where is it right now? Of course we can talk about Laravel and AI in a bit, but first of all, what are we working on?

Ian Landsman:
Yeah, so I've had my main product for 20 years, helped us offer application called Help Spot. And every five years or so, I kind of get the itch of like, gotta do something different. It's like Help Spot's paying the bills and it's great and I love it. it's like customers just want us to ship incremental improvements and all those things, so that's what we do. But sometimes you just wanna, I'm in the Laravel community, there's all these great toys we get.

All the new things and it's like, ugh I can't always utilize those. So I had this idea in my head, I was going back and forth with it for a while and it's turned into Outro. Yeah, and it's basically a tool to organize and monetize your podcast. So to me, that's the core pitch of it. And it really started primarily from the organization, so I've done...

Mostly Technical with Aaron Francis now for almost 100 episodes. And I had a podcast before that for a couple of hundred and something episodes. And you know, I think we do it. A lot of people do, which is like, well, we have Trello or we have Google docs and then you're kind of doing that. And then we Mostly Technical, we started selling sponsorships, which I did for the last podcast too. And it's like, okay, like I got to wire that stuff up and like get Stripe and build a page and do a thing. Can you do that? And then kind of wanna email people, so gotta wire that up and whatever, we haven't even done that for Mostly Technical.

So you end up with all this amalgamation of six tools and they all are generic business tools, none of them know it's a for a podcast or anything like that. So, yeah, it just felt like, I don't know, there's something there. It's like I want a tool that first off lets me organize every episode, so it's like these are the segments we're gonna have, these are the questions for the guests, these are the topics we're gonna cover, these are...

Yeah, if you're not a multi-host environment, it's like who's doing each topic or who's involved if there's multiple hosts like all those things, you know, you can imagine like I just listened to a podcast this morning where like they were discussing something and they wanted to reference what they said a few episodes ago and they didn't have any way to do that. It's like Outro will have your full transcript and you can search for that point two episodes ago where you said something you want to reference it. So all that type of like production elements and then the monetization elements like memberships marketing tools It's a primarily like email and memberships and things like that and then selling sponsorships. That's kind of the thrust of it.

Matt Stauffer:
I love this.

I'm so excited and I hope that is exciting. That's just because you know that I love you and landsman and I want to succeed, but hopefully because I'm your target audience. I just want to kind of like set the framework for those who haven't been podcasting for a long time. When we first started podcasting, there was one, maybe two hosts out there and a lot of people, we would just kind of make our own XML feeds. I remember building expression engine templates that would point to hosted MP3s or whatever on my local server. And every time we pushed up a new one, we would just add an

Ian Landsman:
Yeah.

Ian Landsman:
All right.

Matt Stauffer:
entry into the expression database that would then push it up there. And so the idea of like podcast hosting, man, when Simplecast first came out, I was like, this is revolutionary and democratizes the process of podcast creation. And then more and more tools have come out. You you mentioned in your episode, it Mostly Technical, you know, things like Riverside, which we're using right now, or Streamlabs, these tools make it easier to also create your podcast and stuff like that. So I am all for, even though like there's definitely a meme on the internet of like less, you know, men should have just a podcast microphone in their hand saying stupid stuff out in the internet.

Ian Landsman:
Right? Yeah.

Matt Stauffer:
I still think the democratization of podcast creation not be just the domain of highly technical people or people who can pay a lot of money to do things is a valuable thing. You know, Transistor has really, I think like our friend Justin Jackson has led the way in talking about how that's a valuable thing and writing, creating content and tools that makes it easier for more people to get into podcasting today. But.

You start a podcast and one of the reasons in my experience why you don't continue with the podcast is the friction. And yeah, they got rid of the hosting friction. Once you have an MP3 Transistor makes it extremely easy or simple cast, whatever else extremely easy to get the content out there. But what about what, what happens before the MP3? Right? And I have often been asked by people, they say, how do you run a company and be a present father and write a book and put out YouTube's and also do two or three podcasts at a time. I'm like virtual assistants. It's literally the only way to do it.

Ian Landsman:
Yeah.

Matt Stauffer:
It's virtual assistants and being a process person. I love coming up with a process, defining the process, then getting it to happen irregular, preferably without me involved. And so what it involves is a virtual assistant. And let's see, I've got Trello for sure. I've got Busy Cow. I've got Riverside. I've got Simplecast. We, at one point, were using a transcription service. We've got, if I didn't say it, we've got Trello for sure. And each of it is, first of all, cobbled together. Second of all, if somebody else were to come along, it would

Ian Landsman:
Mm-hmm.

Matt Stauffer:
take me half an hour to walk through my processes and my tooling. And third of all, there's a lot of just very arbitrary stuff in there. Like I built a structure for what the template card is for an episode. But there's the episode before I've invited the person where there's a lot of manual stuff where I'm using email here and Twitter here and whatever else here. And then there's also the template card for the actual episode. There's just all these automated processes forming a tool that is not intended for podcasting to do podcasting things. Right. So when you say

Ian Landsman:
Right? Yup.

Matt Stauffer:
this idea of like it's going to do everything Trello does but it's going to be podcast and specific. I'm like thank god. It's going to hook that Trello card into the email that was sent out to invite them. I'm like my gosh like the amount of time this is going to save my VA and I don't feel bad because I'll give her plenty of other work elsewhere especially across multiple podcasts. Once I have a system and I have the way I want it to work like I'm super super super excited about that. So

Ian Landsman:
Dude, you're my target audience, yes. Yes.

Matt Stauffer:
all that said that's what i'm saying like i'm your guy so how one of the first questions i want to ask because i think this is probably going to be a first question on a lot of folks minds is how do you do market research and analysis when you're creating a category here, right?

Because like, you know, and you mentioned this again briefly in that first episode, y'all, I will link the first episode of I'm sure he's talking about a hundred other episodes I haven't listened to yet. In that first episode, you mentioned you're breaking one of the cardinal rules of bootstrapping where you're saying, Hey, I'm, I'm trying to carve out a new market versus working in a competitive market. And I'm super curious about that. What does it look like for you to make a decision to pour time and money and effort into a thing without knowing how large the addressable target market is or what their willingness to pay money for it's gonna look like? it just, are you just kind of stepping out on faith or what do do?

Ian Landsman:
We're on a lot of faith here, man. We're on a lot of faith. I'm not saying anybody should be copying me on this one. We're definitely breaking some of the rules. Yeah, nothing's established here. So it's not gonna do the hosting part, you know, as you kind of touched on. It's not like trying to be a host, which is definitely an established part of the ecosystem, right? Like could do hosting, right? That would be an established thing. It's not hosting. And it's not the production in terms of like recording, like Riverside and those things.

Matt Stauffer:
Uh-huh.

Ian Landsman:
So it's definitely like a new thing. But again, everybody's having to cobble it together, right? So I know that there's a need, right? Like, because every well-established podcaster, just like yourself, has the same exact story. Like, I've created these processes and organization that lets me actually do this, right? And so part of this for me is like...

And, you know, okay, so in terms of the research, like I definitely did some research. Me and ChatGPT went down the rabbit hole of like how many podcasts are there, right? And like all those kind of things. And like there's not as many as you would like. It's like coming from help desk software, which is like, every single company on earth uses this kind of software, right? Like that's, that's the market is everyone. This is, you know, from a B2B perspective anyway, this is definitely not quite that. So it's going to be.

Matt Stauffer:
huh, yeah.

Yeah. Everybody in the world.

Ian Landsman:
It's a little broader even in that sense, because it's like established podcasters. It's like for everyone, but it's still not that many people, but it's like Joe Rogan, right? Like a king of the hill. Like you could use this to organize a Joe Rogan episode all the way down to like, and that's also a very different need, like, because they're already organized on some level, right? And they already have sponsorship processes and all this stuff, right? And then you go all the way down to like person who's just starting a podcast. And this is more where I primarily am thinking about at this point, because to me, I want to get people podcasting.

And more importantly, keep them podcasting. And I feel like the essential part of that is what you described. You need this organizational structure to do it effectively over years. But the thing is, so many people have to figure that out for themselves. And of course, we're technical. So yeah, you can create a connector between two apps and you can do all these things if you have to. And you're comfortable with the base set of tools and all those things.

Matt Stauffer:
Yeah, or you just burn out.

Ian Landsman:
but none of those tools are guiding you. Like when you go into Trello, you know what Trello is, you know how it works, and you know how to use the API if you need to, and whatever. But if you're just a regular person, and you're like, okay, well here's, people say they use Trello. And then I go in there and it's like, there's nothing in there. There's nothing in there, right?

Matt Stauffer:
Blank screen. Now what? Yeah.

Ian Landsman:
Okay, so I guess I'll put some cards in here, but then like, you get into pre post production. Like, outro has pre and post production to do's. So it's like exactly you're saying. It's like, these are the things I do before an episode. These are the emails that go out, and it can send those emails, and like.

Matt Stauffer:
Yeah.

Ian Landsman:
post-production I can have to do is for the VA or if you have producers or you have an editor or whatever like there could be steps in that and It can understand what the epic like thing I hit with Trello and maybe there's a way to there's probably some kind of way to even do this in Trello that I haven't even done Which is like every episode has like an intro and outro and might have production steps. So You know since it understands the concept of episode it can like pre-populate those things again I'm sure there's some Trello way to do that.

I've never even done that myself. I just wanted like, in terms of a podcast, it's like, this is an episode, what should it have? Outro gives you those things an episode should have, and then lets you add all the custom segments and add reads and whatever else you need for each episode custom in that sense. So yeah, but in terms of the business aspect, I'm quite back and forth on it. I think to me, it's like the baseline is the organizational part, which will probably be free.

And then keeping people going and helping them build their podcast to me is like where the value is gonna be in terms of, I think there's a ton of value in organizing them, but I don't know if people wanna pay for that. I don't know if enough people wanna pay for that, right? Cause it's like, I can use Trello for free. I can use Google Docs for free and whatever. So I feel like, okay, this is gonna be a better way to organize. Come on in here for free and organize, right? And then, then we can layer on. Like you want members, that's like to me, one of

Matt Stauffer:
Yeah. Yeah.

Yeah.

Ian Landsman:
hardest thing with podcasting to me is even when your show gets bigger, like you actually don't get that much feedback back. Like it's hard to get that feedback back. It's not like a central way to even do it. It's like maybe you get a YouTube comment if you're on YouTube or maybe somebody randomly sends you something on social media. If you push, you'll get emails if you really let people know about that. But it's all a little haphazard. So I feel like that whole part of it is part of the monetization aspect to me of like.

A mailbag so you can really organize your inbound stuff. But more importantly, the membership stuff, have members, email, newsletters, all that kind of connection where you can build those connections and start to build the monetization. Because again, that's motivating too, right? The more you can get people towards somehow making money on their podcast, even if it's not a ton of money at first, yeah, it's still like motivating and keeps you going versus.

Matt Stauffer:
That's very cool.

Matt Stauffer:
Yeah, just a little bit, yeah.

Ian Landsman:
feeling like you're alone and you're talking into the ether and all that stuff. So.

Matt Stauffer:
I.

There's so many things you said that I want to respond to. I should have been taking notes, but I was just like, I was locked in. So one of them is I really appreciate the idea of these kind of repeating segments because everyone who listens to podcast knows I screw up my intro almost every single time because I don't remember to have it in front of me because I don't have the card, but you know, and like I'll learn like eventually I'll be like, okay, VA, like every time I got a new episode, I should go to the board on Trello and it should say the person's name and the full, but it doesn't always happen. I don't even remember to open the freaking thing. So yes, I I'm very, very big fan of that. I do want

Ian Landsman:
Yes.

Matt Stauffer:
to talk a little bit about like what's the addressable market from the whole way from the intro to the Joe Rogan you you know kind of touched on that a little bit but I also want to just name that I have two active podcasts and two no longer active podcasts. I haven't taken an ad for any of them on purpose, but never once have I even really considered building a community around them at the level you're talking about, a viable option.

So I'm even like, I'm your target market in part because you're replacing tooling that I built and in part because you're exposing something that I don't even have. The idea, people will often say, you know, your email list is one of the most valuable tools that you have. And I was like, well, I've got thousands and thousands of people who regularly listen to this podcast and don't have the email address of any of them unless they specifically hunted down my email address, sent me an emails and said thank you for the podcast. And usually that's only because they signed up for my newsletter which most podcasters aren't doing, and having to also listen to the podcast. So having an email list or a forum or some other thing like that or them becoming Patreon sponsors without me having to learn yet another tool. Like a subversion of the podcast. This is really... This podcast shouldn't just be about me being excited, but I'm also very excited about this.

Ian Landsman:
Yeah!

No, it should be. Yeah, no, mean, Patreon is like the big competitor, I would say. In my mind, Patreon is the competition. It's like Patreon, but it understands you're a podcast and gives you all these other podcasting things. It's super focused on podcasts, whereas obviously Patreon is like OnlyFans competition and random vloggers and all kinds, anything. It's generic, which it's huge and it's great and it's awesome, but like...

Matt Stauffer:
Yeah. Yeah.

Ian Landsman:
It can't do everything I feel like we'll be able to do by knowing this is really specifically for podcasts.

Matt Stauffer:
So you mentioned kind of like you're like there's the whole range, which is the whole way from I just started my first podcast and the first point all the way up to I'm Joe Rogan and I already have an existing system. I have built a SaaS in the past. I've built a few, but one is coming to mind where it was for people who don't do fundraising. And I very specifically said there was tools out there that serve full-time professional fundraisers and this is not for them. I'm not a full-time professional fundraiser, but there's also people who have to do fundraising part-time as a part of their job and they're not trained in it and they're not experienced and they have some other day job and this is the tool to make them better at fundraising and you know and I'm wondering is this the tool for people who aren't professional podcasters that aren't Joe Rogan's and it gets you from start up until maybe me right like I maybe can consider a part of my day job but it's still really just a very expensive side hobby at this point or do you think you're getting the whole way up to the Joe Rogan's as well eventually? okay.

Ian Landsman:
Right.

No, I want to go all the way. want the whole thing. definitely, whether or not we get all the way to like Joe Rogan, I don't know, but I definitely want to go past where we're talking about you being, because I want it to be for people who definitely make a full-time living on podcasting. Like whether you make hundreds of millions of dollars, like that's, that even starts to get into like a bigger, a different sort of, it's like big enterprise at that point, right? So who knows? That's got its own rules kind of, but definitely want it to be that. And I think it can be, like there's,

Matt Stauffer:
Yeah, cool. Cool, cool.

Ian Landsman:
I think where we come in initially is more, it's gonna be harder to break into very established shows, because they already have MailChimp and whatever they're using for sponsors. They've already built their systems. Are they gonna move it over? Again, I think there's probably benefits, especially once we have it all cooking for them to move over, but at the same time, that's always a big lift to ask people to move everything. So to me, it's more about the early focus for me is those smaller and earlier podcasts, because it's like,

Matt Stauffer:
Yeah. To switch. Yeah, yeah.

Ian Landsman:
then they become big podcasts. They are growing with Outro, right? Yeah, and they're coming up with us. So one thing I did, this is on the business front of this, this was a very specific decision. And I've really only kind of recently come to it, because there is like two paths. think there is the like, it's just really about the organization and forget the membership and all that stuff. And it is then a tool for like, you are established podcasts. You have four hosts and three producers and it's a big frickin' mess, you're across all these tools, right, it's a disaster, this is gonna fix all that for you. And then it's just like an enterprise sales process essentially of like, you're already making tens of thousands, hundreds of thousands, millions of dollars, I'm selling you a tool at $300 a month for this solution to your problems, right? So I do think that would have been one way to go, but I think it's harder.

Matt Stauffer:
Yeah.

Ian Landsman:
Definitely, it's also like I'm not as interested in that path, honestly, of like sort of just another effectively B2B tool kind of thing. So, and I think it's a much smaller market. There's only so many podcasts that are big enough to want to pay $300 a month for this kind of solution. So now like I have to get a pretty high percentage of that market to make that all work. Whereas if it's like, hey, anybody with a podcast is a potential customer.

And once they start getting a few people on the email list, they start getting a few members, and we're getting our fee for those tools. Now we can have thousands of podcasts maybe that have members from a handful of members up to 10,000 members, and we're making reasonable money there in that range. So I guess that's kind of way I was approaching it.

Matt Stauffer:
Well, that makes sense to me as well, because if I were to think about some of those things, one of things that would keep me from building some of that membership stuff is I would, first of all, like you said, have to set up three or four different tools. I'd have to know how to use those tools extremely well. But even if I knew how to use all of them, MailChimp alone, if I've got four or $5,000 regular MailChimp recipients, I think it's over a hundred bucks a month, right? Just on MailChimp alone, let alone all the other tooling you're talking about. And Trello is free off the bat, but you could get to a point with a certain number of team members, certain number of Trello boards...

Ian Landsman:
Yeah, that's sort of the economic analysis I've done is that like, that to me is also where I plan on making money in Outro. That like, if you have 4,000 subscribers, it's probably gonna be 100 bucks a month. But that's what 4,000 subscribers is worth and you're going to be utilizing them more. Like the people just on your mailing list right now that you're, it sounds like maybe not even fully effectively utilizing or they're not in a specific mail for the show potentially either it sounds like.

So can we help you optimize that? Obviously we can be sending stuff when new shows come out, but even all kinds of things around that, right? So there's just a lot that feel like can be done in their polls or whatever, community things, and just keeping that feedback loop in there. Yeah, and then I think then the value over time is, yes, maybe it ends up costing similar to what you were paying MailChimp, but yes, you're not paying for all those other tools that you are also now paying for.

Sort of phase two, I don't know if we'll get to this phase one, but phase two I'd like to do like replace Buffer, like do your social media auto posting and all those things, right? And like, this is more like a 1.5, all kinds of guest management aspects, like your shows, like all guests, right? So like to be able to invite the guests, have that whole calendar selection, Calendly, replace Calendly, like all those kinds of things, have all that integrated. And obviously like you can just put the guest on the show and.

blah, blah, blah. So it's all much more organized and integrated. But, um, yeah. So I think it's a combination of like those things there.

Matt Stauffer:
Okay.

So I said busy Cal earlier and I meant Calendly for anybody who's been correcting me in their head this whole time. But if I run an agency, right, and so one of my main things that I do at my job is talk to people who have an idea for an app and try to talk them into what is more reasonable for them to do. Because what I don't want to do is have you pay us money to build something that we don't actually think is the best thing for

Ian Landsman:
Right.

Matt Stauffer:
you right and so when it's founders the number of times I've had a founder come and say I want to build an app and it's gonna replace these 17 things and I want it you know to work in six months and I'm like so you're saying we need to replace this app this app this app this app this and so I'm like Ian we're talking Trello, MailChimp, you know sponsorships, Calendly all these kind of things but obviously you know that and I know that you know again I have not caught up in the podcast but people at Tighten talk about just kind of like Ian talked about this in the podcast that I enough that I

Ian Landsman:
Yeah.

Matt Stauffer:
I know that it's you and it's a pretty hefty AI development workflow working on this. Can you talk to us a little bit about A, the decision to build an app that is the everything app, right? And B, how are you doing that in a way that doesn't give your bootstrapper heart just a heart attack of like, can't believe I'm choosing to do so many freaking things at once.

Ian Landsman:
Right? Yeah, man, it's hard. So I guess on terms of the decision, I just felt like to me, this is the app. If it's just replacing Trello or whatever, feel like it's so much, maybe in the end that will have been, that's what I should have done. Who knows? I don't know the answer, but to me, feels like, I don't know if that's enough value. I feel like it has to be bigger than that. It has to be more like this is where you go to really organize.

Matt Stauffer:
Sure.

Ian Landsman:
the business of your podcast, like everything from producing it to selling it and all those things, like this is where that happens. Like this is where you can sell your sponsorships, this is you can make money on members, this is where you go in here every time you record an episode, like this is the command center of your podcast. And I feel like anything less than that, so it doesn't really work. And then if it's, yeah, and then so that then implies it has to do all that stuff. So I think.

Matt Stauffer:
It doesn't make sense. Yeah.

Ian Landsman:
My take on that initially is definitely there'll be phases. It's not gonna try to do everything all at once, but it'll definitely have the episode organization kind of stuff. It'll definitely have the membership stuff. It's certainly gonna be the shaved down version of all those tools. It's not going to attempt to do everything Mailchimp does, right? Because that would be crazy. So again, this is where it also lines up to me as more like, hey, this is gonna be kind of a light solution at first. So people earlier in the process make more sense, because it's people who don't need, oh, give me A-B testing on these member emails I send, right? Like, so it's not gonna have A-B testing on your member emails, but that's okay, because you only have 100 subscribers, you don't need A-B testing, right?

So, right, so that's okay. And then like, hey, but three years from now, when we have customers who have 100,000 members, right, then it's like, well, okay, they're asking us for A-B testing, and then that kind of makes sense, and then we'll build those features and.

Matt Stauffer:
Yeah. Every feature. Yeah. Yeah.

Ian Landsman:
whatever we go from there. So the scope, trying to keep the scope, I'm trying to let myself go broad with the scope in terms of accepting more types of things, which is sort of weird, but then not let it go too deep on any of them, at least phase one, as sort of my philosophical plan. And then yeah, I've definitely integrated a lot of the AI stuff. I mean, I'll talk about that in one second, but I will say, it's hard, you know.

and Userscapes been bootstrapped the whole time. We don't have a big team. And it's also like we're doing a bunch of stuff in Help Spot. Of course, like these things overlap. Like we're doing this whole big redesign of Help Spot and like we're redoing the marketing site and all this stuff. So like I actually haven't even worked on Outro in like three weeks. Like, cause it's just been three weeks, right? Even with the AI and all this stuff, I just haven't literally had time to even sit down with the AI and do anything. So that's how it goes sometimes. You got kids, it's summer, you know.

Matt Stauffer:
Yeah, yeah, yeah, it's too busy. Yeah I do.

Ian Landsman:
All the stuff there, you know how it is. Yeah, so I'm excited about the fall and I think it'll be a little more normal, back to kind of normal schedule. But yeah, the AI is great. think my plan is a little bit multi-fold in this part too, because I think the AI is super good at getting you rolling and pushing you through roadblocks and things like that. So I've definitely gotten way farther than I could have gotten if I was just sitting down coding because the thing is I always hit roadblocks and I'm like, and then something comes up because I'm still running the company and stuff and then you get distracted over there.

Matt Stauffer:
Yeah, gotta disappear, yeah.

Ian Landsman:
Yeah, and then the day's over and then you didn't even finish the thing you started in the morning, right? So the AI has been really good for both like plowing through when I just don't know how to do something or iterating fast on different options than being totally comfortable scrapping the bad options because whatever, I spent 10 minutes with AI doing it and I don't care, right?

But also, and also sometimes we can just let it go on its own. It's like, okay, it's gonna go build this thing. I spec'd it out in detail. It's gonna go do it. Now I can just go work on the other businessy stuff I have to do. So that part's really great. I think, you know, as it gets deeper and more complicated, we'll see, I feel like the cracks show up a little bit more as the app gets more complex. you know, I could see bringing on some help, whether it's the internal devs we have who are really super busy. So I don't know, or maybe having somebody outside.

Matt Stauffer:
Yeah. Yeah.

Ian Landsman:
Come in and help on some stuff there. So I do think we'll reach the point while need need some other dev help. But not quite there yet.

Matt Stauffer:
So I have been historically pretty critical of AI for development workflows. One of my friends, Phil's angle, was like, Matt, you can't really be someone who's trying to be like a thought leader in the world, being critical when you have not actively used it on a project. And I was like, OK, I hear you. So I'm building this internal tool that we're using as a part of our sales and marketing team. And I'm choosing to use AI for the whole thing. And that makes me one of the more inexperienced AI developers out there. I'm going to be very transparent about it.

Ian Landsman:
Yeah, awesome.

Matt Stauffer:
I do talk to my whole team about it, right? So I'm getting their thoughts as well. And they wind up with my experiences, which is that the average person's usage of AI, which is not yours. And that's why I want to talk about yours a little bit. The average person's usage of AI, if you are an expert in the field, so if you were an expert in Laravel and you have Claude or you've got cursor or something like that, it will be faster at some things, but you often spend as much time or more reviewing the code than you did would have just writing the thing in the first place. I, similar to you, I'm a business owner.

Ian Landsman:
Yeah.

Matt Stauffer:
I have two minutes to code here and there. So I'm like, great, this is this really ideal scenario where I look at the app, think of something it needs, I tell Claude to do it, and then I go on six hours of calls. And then I come back off a call and I go look at Claude's work and I'm like, no, not quite right, make this change, write a test for it, run the test. Hey, I told you to write the test and, pest, why are you not doing PHP unit, right? It goes and does the thing or whatever. And then I come back or whatever. And that feels like the dream until I'm ready to actually merge all that stuff. And then I am spending two hours

Ian Landsman:
Right.

Matt Stauffer:
reviewing the code because it's written so poorly in a lot of ways that I have to rewrite the whole thing in order for it get to the point where I actually want it to be I'm just kind of like I don't know if it would have been any better to just write it myself and not have to do this whole back and forth so it's weird because it gives me these moments where it feels like oh my gosh this is so great but the actual practical end result isn't and I've kind of read some articles I'll link one in the show notes where people said like all this whole AI makes us X percent faster is self-reported none of it is actually tested none of these articles that are talking about how much faster AI makes developers actually use any practical metrics. They're literally just self-reporting. And I'm like, so it's completely open to our delusions of, think it's making me faster, but it's not. I'm not saying Ian Landsman is not susceptible to those same delusions, but I also trust you a lot. You're extremely practical. You're extremely experienced. And you have a AI workflow that is what nobody else I know has. So whether or not you will land on the, I think AI is the best in the world camp a year from now, you are doing some really creative stuff. So do you feel like you can give us the TLDR

Ian Landsman:
Right. Yeah.

Matt Stauffer:
of your whole, I've got multi different clods and one of them is writing specs and again I only know that this exists. I don't actually know it. Is that something you could share with us?

Ian Landsman:
Yeah. Yeah, yeah. So I mean, here's, yeah. So I think big picture, but then I'll go into the detail of how I specifically work. But I think I have a little advantage here, I guess, in the sense of like, I don't feel like I'm a very good programmer. Like I feel like I'm a super generalist.

That's how I've always been like I learned the program basically building HelpSpot I had like the JavaScript Bible book on my lap as I'm learning it and whatever and I've always been a programmer who's also responsible for running this business like I was I've never been a professional programmer where my job was to program and not I had no other responsibilities like I was just a programmer. So I've always been this like I was just most I did some stuff at a previous job now a million years ago where I was doing some programming by still all these other responsibilities and

Matt Stauffer:
Got it.

Ian Landsman:
And then I had this company where I'm running the company and doing the support and selling and programming, right? So, you know, so I think it's not, you know, I'm not the world's worst programmer, but I'm not like super fast inherently with my programming. I'm not doing it that often that like every Laravel magic trick is right in my head. So, you know, I'm off in the docks, like wandering around looking for a thing I think I know it might do, right? It's like, I'm having to do all that stuff. So for me,

Matt Stauffer:
Yeah.

Ian Landsman:
and I could be totally delusional, but I do feel like it makes me significantly faster and part of it is just that it knows the function names and whatever, it can do those things. But the other part is just, I would also tend to get kind of in like a perfectionist kind of mindset in my more, I will say this, like in Help Spot I didn't have that. When I was building Help Spot, I was like, I quit my job in order to do this, I have to build this, it must get out.

Matt Stauffer:
Yeah. I have the ship. Yeah. huh.

Ian Landsman:
I can't be precious, I must ship. Okay, this code is crappy in this spot. That's unfortunate, but the reality is it spits out the right thing at the end and that's gonna have to be good enough for now because otherwise I gotta go get a job again in a couple months if this thing doesn't ship, right? So now ever since then I haven't had that kind of motivation because it's like I can build side projects, I can do whatever, and I can be precious with them because I don't have that need necessarily to ship to survive.

Matt Stauffer:
Yeah.

Ian Landsman:
And I think it's like hurt those products, honestly. And so now it's nice because it's like, I can push through that stuff. It's like, I'm not even the one who wrote this, right? I didn't even write it. Like, so where you're looking at the code being like, man, it's gonna take me hours to like go through it. I'm like, this works. Yeah, I'm like commit.

Matt Stauffer:
You're like, commit.

Ian Landsman: 3
Like, I mean, I'm not letting it do crazy shit. I'm definitely reviewing it and I'll talk about that in my workflow. So I'm definitely reviewing it, but I'm not, yeah, I'm not going through it with a fine-tooth comb. I'm letting it go and being like, we're gonna get to the working version of this thing, and it's gonna ship, and you know what, we can double back and clean stuff up. I've already done that a few times with a couple passes back through to, you know, the biggest problem for me is not that it ever does any one thing wrong. It's that it does, one thing one way and then two weeks later you have to build something else and it's done it like a slightly different way, the kind of behind the scenes part of it.

Matt Stauffer:
Yeah.

Ian Landsman:
And you're like, well now, like when I'm working through this, it's like, it's like this little mismatch of like maybe how it named a component compared to a previous time or whatever, just how it structured things. And you're like, I don't love that.

So whatever, I'll hop out, go back through and be like, well, let's fix this to match in one direction or the other and stuff like that. But yeah, I think just being able to plow through and be like, wow, this feature's built and I can move on to the next thing, build the next feature, go through, be able to scrap stuff that's bad, like all that stuff. You know I think again, that's a part where in the past, I took a week and built this thing and it sucked. And now that's like, now I don't work for a month on the project, because it's like, whatever, it's like annoying and I have to rebuild, I have to go back and build the thing again, I just built it in a different way and blah, blah. So now, like don't ever feel that pain ever. It's like, okay, like scrap it, do it again.

Yeah, so in terms of my specific flow, yeah, do have, I mean, there's a couple different ways to do it, but the thing that's worked best for me is to always create a spec and then have it build from the spec. And so what I'll do is if you're using Claude Code, you can have different like slash commands, or now they have different agents, they call them a couple different ways even to do this, but.

So I'll have a slash command that's like the planner. And then it's kind of, you know, the prompt, base prompt of it is like about being a Laravel architect and the LiveWire and like all this stuff, right? And what it's gonna do, it's gonna take the input and it's going to help me plan it. It's gonna write it to a markdown file. And so that's kind of the core is like, I'll be like, here's the feature. I'll write it up pretty good. I'll give it to the planner. The planner looks through the code base and it's like, okay, this means we have to like, create these files and edit these functions and blah, blah, whatever it has to do, but it does a really detailed plan and like way more detailed than I would ever write in a million years, even for like a human.

Again, this is like my style, I don't know, Tighten, you guys do awesome spec docs, cause it's like a consultancy, but a little looser.

Matt Stauffer:
We keep it pretty simple.

Ian Landsman:
Okay, so much more, I would say in depth document than I would ever produce myself, then I edit that document directly. So, I read it, see what it did, kind of especially at the higher level of like, is this actually what I told it to do? Is there any subtle things where it's got it wrong or sometimes it gets too, it still gets confused about stuff like thinking it's working in production, for example. And so it's like, well, here's a migration strategy. I'm like, we don't need it. So I just erase everything about migration strategy, because there is no migration, like it doesn't exist yet, right?

Matt Stauffer:
Yeah.

Ian Landsman:
So there's stuff like that that creeps in there. So just make sure like what I'm feeding it back in that the spec is like really tight and good and then I have another agent. That's the developer Base prompt is like your a Laravel developer, but blah this is how you write tests, you know, here's some examples, but blah and then I feed it the plan. I'm like, okay execute this plan and then it goes off and it it builds it. And then the final step usually is like I just open I just use you git hub desktop and I'll just look at the changes in there and review the code, see if it makes sense.

And then obviously I'll check in the UI and run the tests and all that stuff. And that's it. And it goes pretty quick. Yeah, I've liked it. Definitely not perfect. Definitely because it lets you move fast. You can now move fast in the wrong direction. So I've had that happen a couple of times where I'm like, I built a whole big feature. Like, feature is kind of stupid. I don't know if I should have built this big feature. So yeah, there's some stuff like that, but yeah, that's how do it.

Matt Stauffer:
That's funny. Okay. that's really cool. And I really, know this, this podcast is not about Ian's AI strategy, but I did want to kind of just get that out there. One of the reasons I wanted to ask about that is, I'm curious for you. Do you think you would take on this project if you did not have AI for help?

Would you just do it and it would just go slower? Would you do it and would you pay for help? You know, like, is this a foundational part of you even choosing to take it on in the first place?

Ian Landsman:
So I definitely think with my personality and just as I've seen in the past, I think I would do it, but I don't think it would get done.

Matt Stauffer:
Noted. Yeah.

Ian Landsman:
So I think that's the differentiator. I think I would do it, but then the reality of being pulled back into our main business stuff all the time would just be ever present there and eventually you're like, I'm on a year of this, still not done. Because it is, like we talked about, fairly ambitious. Like it's not just the little to-do app that's got a little twist to it.

Matt Stauffer:
Ship in a couple of months. exactly.

Ian Landsman:
It's, yeah, it's kind of got a lot going on. And so it could easily just stretch out for a very long period of time, which, it's already stretched out a little bit of a long period of time, but not crazy long, yeah, a couple months or whatever it's been. But yeah, so that, we'll see if I actually ship it. I think, I believe I will, but you know, you never know. But yeah, I think that's kind of the thing. I think I would...

I would want to do it and I would start doing it, but would it get done, think, would it either be, wouldn't happen or it would have to happen a different way. Like right from the beginning, I'm hiring a developer and like that whole path of like, you know, which I mean, obviously is how it's been done in the past. So it's workable, but you know, then that's a budget item and I got it. Well, do I want to spend $100,000 on this idea? Like, is it that good of an idea? I don't even know if I like it yet, and whatever. Like, again, the AI is so good, because it's like, now I know I like it, and I feel like it's a good idea, because I built it enough to know that, I wish I could use this myself for my podcast. So yeah, so I'm far enough along where now I'm okay spending money on it, actually, and it's like, so we have the designers doing a fancy logo and all that stuff, because it's like, I'm more comfortable that it's an investment. Yes, yeah, exactly.

Matt Stauffer:
Yeah, you validated it without the cost. Yeah. And a lot of people are so worried about the future of programmers and consultants as a result of programming, as a result of AI. And I'm not saying there's no threat at all, but what I heard you say was there's an app that never would have gone to production if I was building it myself. I may have hired a contractor to do it, but I might not have had the money for that. And now that I've used AI to build it, there's a very good chance that if it does well, I will then hire programming help.

Ian Landsman:
Yes.

Matt Stauffer:
So I'm like, in the end, we've got one more app out in the world with the potential that if it makes money, we're going to hire a program to work on the thing anyway. It's not like you're like, AI is going to run this thing forever, right? So I'm just like, this is just another example to me where I'm like, AI has moved things around a little bit, but I'm not worried that now I'm out of a job because Ian's using AI for this thing. So it's kind of fun hearing you talk about it that way.

Ian Landsman:
Yeah, no, I totally agree. I don't think it's going to do that. I don't know, again, do they invent a totally self-aware AI that's like an actual human tomorrow? Fine, but then I feel like there's bigger problems than your job as a developer, right?

Matt Stauffer:
Yes. Yeah.

Ian Landsman:
So who knows? The world's gonna be in chaos. But if that doesn't happen, which I feel like it's probably not going to anytime soon, yeah, I just feel like you still need the human to manage it. Like maybe the job changes and there's more, you have to maybe understand more of what you're building and why you're building it and...more of the business reasoning behind things and things like that.

But at end of the day, there's so much bad software out there. And then, and there's so many things that have no software at all. It's like the combination of software that's terrible and software that doesn't exist that should exist is like humongous, humongous amount of software there. So you're just gonna need a lot of people and a lot of AI to, I mean, the reason it doesn't exist is because it hasn't been financially feasible with the number of developers that exist to build all that software and the money behind it. But now it's like,

Matt Stauffer:
Yep.

Ian Landsman:
Well now in these smaller niches, you don't need as much money. So that works out in bigger areas. You could put even more resources towards it. So yeah, I don't know. I feel like it's going to just expand, but we'll see.

Matt Stauffer:
Yeah, totally. I had another question for you and that was such a great point that I got totally distracted.

Ian Landsman:
No, sorry.

Matt Stauffer:
No, no, don't apologize. It's a great point. I really appreciate that. so.

Ian Landsman:
It was about the worry of AI.

Matt Stauffer:
There is that, but this is the Business of Laravel podcast and we're talking about, you know, app that you're building, you know, in Laravel. But I am curious as you thought about, you kind of took a CTO role here, right? We're often talking to CTOs and CEOs and founders. As the CTO of Outro, how did you approach making the technical decisions around what front end were you using and what sort of architectural strategies were using and what does your hosting look like?

What did you choose and what guided your choices there, especially as this app exists and you have so much experience knowing things in the Laravel community. I know you say you don't stay on top of everything, but I know that you have thoughts about React versus LiveWire versus whatever else. So what motivated your decisions in the big architectural pieces?

Ian Landsman:
Yeah, so I'm a total just, unless you have a very strong reason, I'm just gonna stick with what I know for the most part. Unless it's like, yeah, the thing I know just literally can't do what I need done, then fine. what we're talking about here, Outro is a very, it's pretty cruddy sort of app. It's not a lot of magic on that front. There's gonna be some AI stuff in it and whatever, some cool sprinkling magic dust on things, but it's not at the end of the day you know, gonna need to scale to a billion users or all this kind of stuff, right? So, yeah, so it's gonna be, it's Laravel. I'm a LiveWire guy, so I'm using LiveWire.

Matt Stauffer:
Love it.

Ian Landsman:
I did a couple years ago take some time to learn, sort of, React. I mean, I'm definitely no expert. I did not care for it at all, so React was not for me. Yeah, so LiveWire, Laravel, I'm like, great, Laravel Cloud exists now. Gonna go on Laravel Cloud, right?

So that's kind of my stack is like, keep it simple. Again, like this is where I feel like, at least in the modern age of like, at least currently to leverage AI to its maximum, I feel like having a strong understanding of the stack is super useful. Cause this way I know if it goes off the rails. And so I know like I'm building a production ready app that yes, I'm leaving some rough edges probably, but I know generally it's pretty stable and reasonable. Cause I know a Laravel app and I know what it's written is at least reasonable.

Matt Stauffer:
Yeah.

Ian Landsman:
Whereas if I was like, hey, I'm gonna do this in Go, like I have no idea. I could be leaving huge open doors to stuff. Like I have no idea, right?

Matt Stauffer:
Yeah. Security gaps and you had no idea. Yeah, yeah.

Ian Landsman:
So I think that I'm just still leveraging the skills I have to be able to guide the AI faster and not just total vibe coding. Here's some language I have no idea and we're just gonna hope it all works out. And again, I think for some apps that's even probably fine, right? But for this, this is not a super security oriented app or anything, but I still want it to be secure. I still want it to be stable. And we're gonna charge money for things in there. So yeah, so pretty straightforward stack. I think if you said what is, what do you imagine is the standard Laravel app stack in 2025, that is what Outro's using. Yeah.

Matt Stauffer:
got it and if somebody I know we're kind of coming towards the end of time so if somebody were excited about outro like I am what does it look like for them to follow development or to get to try to use it is there a waitlist should they just subscribe to Mostly Technical what are their next steps?

Ian Landsman:
Yeah, they should definitely go to Mostly Technical. That's where I talk about it on a regular basis. And yeah, if you go to outro.fm, there's a link to kind of Mostly Technical there, and you can follow Mostly Technical's kind of Outro page, become a member of Mostly Technical. And then just as soon as I build the way to actually email the members, you will get an email and regular emails from me about the development process. So short term, listen to Mostly Technical.

Medium term, I will complete the ability to email the members and then you will get emails from me about what's going on with Outro. So that is the best way. People on the list will definitely be first into the beta and all that. Yeah, become a member there if you're interested.

Matt Stauffer:
And is there anything about Outro you wish we had talked about today that we didn't get to?

Ian Landsman:
Geez, mean, there's like, this is like the perfect podcast for everybody. We have tons of like business angles and all kinds of stuff. I mean, there's a lot there. guess, I don't know. I don't know. I just think it's interesting to, I guess it's interesting to like take a shot on something different, more of a B to C-ish type of thing that's different for me. So I think like the push your envelope, kind of try different things, you know, when that's feasible, it's kind of cool. And that's the part...

Matt Stauffer:
Yeah.

Ian Landsman:
kind of got me excited about the whole thing and just a whole different area, not like pure generic business or dev stuff. It's like, podcasting, like this is fun and vibrant and people are out there. I mean, just recent elections, all these things, like podcasts have played this outsized role, you know? And so I think it's kind of cool to be working on a product in an area that's more in the mainstream sort of. So that's interesting. But yeah, I don't know. I don't have any specific topics. I think we actually covered...

Matt Stauffer:
Yeah.

Ian Landsman:
More than I thought we would in 45 minutes. So that was a good job on your part hosting.

Matt Stauffer:
I love that.

I'm a fast talker. I did have one question that that brought up to me though. You're talking about the idea of kind of working in a B2C world and you have historically been somebody in the bootstrapping community. For those who don't know, Ian's former podcast was all about bootstrapping and it was one of the premier podcasts talking about bootstrapping your business. And you also just, you spoke at places and stuff like that. And you have often been in the like, look, B2C is tough and difficult. B2B is where the money is and stuff like that. You're definitely in a different world. You're definitely stepping into something that's different but also fun and one of the things that at least Taylor often says when he talks about building things he's like look I built the thing that I wanted and I don't really care if anybody else ever signs up you know. How would you feel if you built this whole thing and it is your dream tool and you and I are the only people who ever use it does that feel like a loss or is that kind of like yeah whatever it's good oh I'll be there with you to the end are you kidding

Ian Landsman:
I'm glad you're gonna be there with me. As long as you're there with me, Matt. Now, yeah, mean, listen, that was definitely my whole mindset was like, I want this for me. I do a podcast now. I plan on podcasting into the future a long time. And so this is the tool I want. I hopefully other people will find it useful and valuable. I'm lucky enough to be in a position where if that's the case and only me and my friends like it, then that's okay with me. Like, it's not the end of the world. I'm not

Matt Stauffer:
Yeah.

Ian Landsman:
gonna be out on the street or anything. So yeah, so I think that's fine. If that's the way it is, then that'll be how it is. But I'm pretty optimistic on some level. I feel like the free parts, I will definitely get users. Can we make it a profitable endeavor? I feel like is a little bit different of a question in that part, I'm unsure. But yeah, we'll see, we'll see.

Matt Stauffer:
Yeah, if we had more time, I would pick your brain all about different pricing models and everything like that.

Ian Landsman:
Yeah, there's a lot there.

Matt Stauffer:
But the good thing is just from the first mostly technical episode that I listened to, you guys talked about it. I could already tell that some of that is being covered. So I will tell you all because I'm, you know, I'm still catching through. you go to mostly technical episode 88, that's when you really start talking about it. 88 is June 24th, 2025. So if you just start there, you're going to be going along the journey with me of learning, you know, in retrospect, all the business

Ian Landsman:
There you go.

Matt Stauffer:
decisions and thinking that Ian has kind of gone through and chatted with Erin about as we kind of learn about this. I am very excited to go to Outro.fm and put my email address there and get notified and be one of your first users. So I wish we could talk more. I promise everybody I try to keep this under 45 minutes. So thank you so much for hanging out and I look forward to more updates in the future once you get the email thing working.

Ian Landsman:
Awesome. Thanks for having me on.

Matt Stauffer:
Awesome, rest of you, we will see you next time.

Ian Landsman:
Later.