What Jason Fried Learned from 26 Years of Building Great Products

[00:00] Running a business is not that interesting to me. I really fancy myself more as someone who makes products. It's like, [00:06] You just get a feel for things that are a whole, a single piece, a single idea, a single concept executed so beautifully. You get a feel for that. [00:15] When you run into stuff like that, it is a spiritual experience. [00:32] Jason, welcome to the show. [00:34] Good to be here, Dan. [00:35] So I have a very important question to start with. What watch are you wearing today? Are you a watch guy? I am a watch guy. All right. [00:45] So today I'm wearing, I'm embarrassed because I don't know the reference number. I don't remember exactly. It's a vintage... [00:51] Hoyer [00:52] Wow. I think it's called an 11... [00:56] 63 or something like that from 1974. [00:59] And I dig it because I just like the color. I like the case. It's kind of that 70s style tonneau case. [01:07] And then just the really bright orange. It's kind of a neat piece. It's nothing like... [01:12] remarkable but really kind of cool. I've been enjoying it for a while. It's beautiful. What about you? Well, I'm wearing a sub which I bought for my every five-year anniversary. [01:25] You buy a new watch? [01:27] uh just yeah just for like uh you know i've been doing it for five years right i'm gonna mark the occasion nice

[01:33] Nice job. Did you get it from an AD or did you have to get it pre-owned or? I got it pre-owned. Okay. Yeah. They're hard to find, unfortunately. Yeah. Yeah. Um, so, but there's something here, which is like, I think you have this interesting, um, [01:49] aesthetic appreciation for things like watches and cars and stuff like that. I think also you can see in the products that you make and the products you make are so well-crafted on every level. I'm curious what the relationship is or what the overlaps are. [02:03] The overlaps. I would say I'm inspired by a lot of things that are not software. [02:09] So we can start there. I'm inspired by watches. One of the things I like about watches is that... [02:15] They're basically all the exact same thing for the most part, yet there's like a thousand different designs, you know, and I think that's interesting. I mean, there's, of course, different versions, but really it's like, you know, there's a few hands pointing at a few numbers and some that can do a few other things. But for the most part, it's like a round base on your wrist. [02:35] to some degree and like wow there's a lot of different ways to to do that and i think that's always been interesting to me um cars are um [02:43] Full of details, materials, how things come together, how things feel tactically, you know, the tactileness of something, the ergonomics of it. Where is it? Is everything within reach? I'm just fascinated when I sit in a car that has really good ergonomics and you could tell someone really thought about it versus someone sort of drew it.

[03:05] Like there's this sense of like, oh, someone drew this out. There's a blueprint here. And then they put it together versus like someone kind of probably, I'm guessing, I don't know, but like sat in the seat and thought about what it'd be like to drive this. Same thing is true for great architecture. So I love architecture is probably my favorite. [03:20] my really true, I've realized like my real true love in the arts, let's say. And being in a great space, in a great room and a great building of any sort is just kind of almost like a spiritual experience for me. Just the way the proportions are and the light comes in and the colors and the [03:43] The scale, it's just all those things. I just, I love the feeling that it gives me, I would say. [03:49] Same thing is true for being in a car like inside or outside and then also like a watch. And I try to want to build products that give me a similar feeling, understanding that there's huge limitations. I mean, we're talking about like a flat screen. [04:03] and pixels. So I can't [04:05] bring different materials to the table, you know, um, but you can bring a sense of scale and you can think about it in terms of what if it was a physical object to some degree, um, [04:14] And I just, I don't know, I try to find that place where I feel a deep satisfaction with [04:22] with what I'm looking at and using in the same way I would if I was to stand in a nice building or be in a nice car or something like that. Trying to find that feeling. [04:31] There's not really an equivalency here, but there's a sense of...

[04:36] Yeah, that feels right. And that's what we try to do with the products. What's the last building you were in that made you feel that way and why? [04:42] I was in a building, um, [04:44] In, um, [04:47] Big Sur, California. [04:50] Um... [04:51] Okay. [04:53] It was, do you know what Esalen is? [04:57] Yeah, so I was at Esalen. I'd never been, first time I was ever there. And there's this really beautiful meditation, circular around meditation hut building, which is down by this river. [05:10] And [05:11] Um, [05:12] I've been in many, many buildings that I've really appreciated. And this is just maybe the last one I could think of that was like that, where I just walked into it and I said, this just feels good. [05:21] There's something about the scale, the space, the materiality, the, the, [05:26] the radius of things. I don't know what it was. A lot of things and the location just made me feel good. [05:32] Like this is the right building for right here. [05:36] um [05:38] Things I tend to like, just like... [05:41] buildings made with very honest materials. So I actually also enjoy looking at [05:46] modern architecture and some being in some modern architecture, but I find most of it to be [05:52] Um, [05:53] Oftentimes it looks good in pictures and not as good in person. Meanwhile, a lot of older buildings or buildings made of more natural materials are [06:03] Um, [06:04] feel better in person they look like than they look in pictures.

[06:07] And so I like the in-person feeling. That's what I kind of judge something by. So that is really interesting. One of the things that you said – [06:15] uh, [06:16] just now about [06:18] enjoying being in a car, for example, that someone had obviously sat in as they designed it. [06:25] At least I think they did. I don't know. I think that, you know, you can kind of tell in a certain way. Did it come from a blueprint? Did it come from experience? [06:34] And the... [06:36] The thing that it makes me think of is I know you're a big Christopher Alexander guy. [06:40] Um, and he has his book that I read in college when I first met you, [06:44] called The Timeless Way of Building. Yeah, great book. It's a great book. And I literally have not read this in 15 years, so I'm probably going to butcher it. But I do remember he makes this distinction between I think what he calls... [06:57] self-conscious and unselfconscious design. [07:01] And unselfconscious design is like where design starts. And it's, and he makes this analogy to the way that people in primitive societies might build their house. Like they're literally just building a hut as they live in it. And they're patching holes as they come up and they're, [07:18] there's a very direct feedback loop between the person living in a space and feeling the like tensions in the space and then resolving them versus, um, [07:27] Now we have... [07:30] specialized people, architects who are like making plans for a thing that they're not going to really be inside of and don't necessarily understand the people who are in the buildings. And in many cases, is that where the, where some of this comes from? Yeah. You know, I'm just trying to think, ah, I do. So I have, um, been on this like book kick for finding books. This isn't, these are not the only two, but these are two that I bought recently, which are, um,

[07:58] Exactly. We're kind of talking about. This is like a book of, of handmade, handmade buildings. [08:05] Non-architect designed buildings, just spaces. [08:09] that people made themselves... [08:11] Um, [08:12] You know, weird, neat things, you know, just like and and and some of these things like look at like look at the inside of this crazy ass thing. And this is like a geodesic dome kind of thing. But, you know, you can imagine like. [08:28] You'd love to be in a space like this. There's something about the feeling of these spaces. [08:34] And so, no, this is one of the books. This is another great book called – [08:36] handmade houses. [08:38] And it's similar style. Wonderful pictures of like... [08:46] Like this is a crazy ass like kitchen sink set up here. [08:50] You know, just like... [08:51] But look at the panels. They're diagonal in the back, and there's just kind of stuff everywhere. And this is not about it being a mess. But this is – someone probably was able to find – [09:04] windows from other buildings and pieces of glass and they just made it all work. Right. And I've been in a number of buildings like this, not like these, not these specific buildings, but. [09:13] There is a real soul and character in, [09:16] that comes through in a space [09:19] When someone... [09:20] who wasn't an architect designed it just for living for themselves. That's not to say there aren't great architects and there are, and there are amazing buildings built by amazing architects. And I love many, many buildings built by many great architects. John Lautner is a great example of someone who I just love, love his houses. Number of great architects.

[09:41] Anyway, but there's still, for me, a charm and a soul stepping into a space that was just put together. [09:48] by someone with like [09:50] a crafty creative vision and even if they don't even have that but just kind of sewed it together essentially and [09:57] I don't know what it is, but it's similar to the Christopher Alexander point. I think, you know, his whole point is like the best architects are the people. [10:04] essentially who need the spaces um and and uh you know [10:10] Again, there, of course, were incredibly important buildings built by great architects, too. But I don't know. I think there's something to it. And I know it's an acquired taste. Like, I've been through some of these spaces with people who don't share my point of view. And they're like, what is this place to fucking dump? Like, yeah, I mean, it is in a way. But... [10:33] It's a good one. And they really, and I don't know what it is, but I really like them. And I don't know how to make things like this, but I really like them. And I pay more and more attention to things that are built that way. [10:48] than the things that you might, someone that the average person might look at and go, that's amazing. [10:54] So we've made it 10 minutes into this podcast without talking about AI, which I think is probably right. But I'm going to bring up AI because there's something about this that reminds me of some of the things that I've been noticing. So [11:08] Inside of Every, we incubate products.

[11:12] And we have four that we run internally now, in addition to the newsletter that we run. [11:19] And there's something different about building products in AI. One, because [11:26] The game board has been reset in a lot of ways. And so everything is, everything is new. So, [11:32] It's this really, I think, unique time to build for yourself because anything that you want is, [11:39] probably hasn't been done. [11:42] And then you also have all these tools that make it easy for [11:47] anybody to build a thing [11:49] Like it's way easier to just build a prototype than it ever used to be. [11:54] And so, you know, all of our products are built by one person and they're and they're building for themselves and first and then building for everybody inside of every next. [12:04] and then building for the audience after that. And there's something about that. I mean, I think we aspire to have our... [12:14] products be a little bit more polished than, um, then, than some of the houses house examples. And, but, and there is something about that where it's like, [12:25] It's a uniquely good time to be building things that you live inside of and can give to other people. [12:32] Yeah, I mean, I think one of the differences, of course, like with these house parallels, like these people built these houses for themselves. [12:38] to live in in their own lives. [12:41] a product usually would build for

[12:43] I mean, you can build for yourself to your point. And that's what's really wonderful about AI building right now. I think most tools that are going to come out of this are actually very personal tools. [12:53] But generally, a product, if you're a product company and you make products to make a living, you make them for other people. And so when you make things for other people, it's a little bit different than like hobbling together something for yourself. And this is, I think, one of the really interesting things about that I don't really see actually, frankly, discussed enough. There's a lot of bragging stuff. [13:11] about how fast people can make things these days and then i go make things for who [13:16] Yeah. [13:17] And, and, [13:18] That's where I think there's a breakdown because I think you can make really – [13:22] You can make things quickly for yourself. [13:25] And I think that's incredibly valuable. And this is how I got started in software. I used to make FileMaker Pro databases. For those who don't know what that is, this used to be, I mean, maybe FileMaker Pro still exists, but it's like a graphical user interface to basically make a database and you could layer your own graphics on it to build an interface. And it's essentially a product that you make for yourself to store things and look things up, which is essentially what most products are anyway. All the backend stuff was provided by FileMaker. You could drag in these tools and put your UI around it. [13:55] are just tools I made for myself. [13:57] And FileMaker was kind of, I didn't know how to program, but I could figure out how to make FileMaker and do some scripting and stuff and kind of pull things together, which is essentially what people can do with AI now even faster and better in a lot of ways. So I think that's incredibly good and wonderful. [14:11] I am still currently working.

[14:13] I'm skeptical. [14:15] um but optimistic but skeptical at the moment that people are going to be building [14:21] really great tools for others. [14:25] purely with AI. While you can basically [14:29] Build a great tool for yourself purely with AI. [14:33] But once you have multiple people involved and all the edge cases that come with multiple users and people who don't know how a system works like you do or have different approaches, it can break down pretty quickly. And that's really the art of product development is like... [14:47] edge cases and conditions and all these little small things that you need to, all these little different piece of fabric you need to sew together so you can't see the seams. And it's easy to do when it's just for you because you can kind of live with things that don't work so well, but it's hard to do for others. I mean, I definitely agree in one sense that – [15:08] All right. [15:08] I've seen everyone on our team, technical or non-technical, build things. [15:13] And if you're non-technical, you can definitely build something and get it working. But getting it to be something that we would launch or something that even people internally would use is very hard. And usually, at least at this point, unless it's something self-contained, so something in a cloud artifact or something like that, it's not going to be something that other people are going to use. Yeah. [15:35] However, I definitely don't agree in the, if you are a professional developer, you're [15:43] Um,

[15:44] and you're building with these tools, no one inside of every is looking at the code, is hand coding anything. [15:51] everybody is using these tools to, um, to build and, you know, uh, uh, deploy and like basically, you know, the entire product development life cycle. Um, and, and I think it helps with all those specific things, like all the, um, all the little edge cases and all the little seams, if you're using, like, you have to obviously use it in a way that is conducive to that, but, um, [16:15] I just sort of see it as in the same way that, you know, when I was growing up, people were [16:23] sort of pretty suspicious of scripting languages and ruby and javascript it has the same kind of thing with english and it changes the like substrate of what you're programming on you're programming in english but you're you're writing in english about all of the different implementation details almost like pseudocode and that's where the programming happens which i think is a total change um so i don't know how much you know how much ai adoption inside of [16:48] 37 signals you have for this kind of thing, but it's, it's been really crazy to watch. It is crazy to watch. I mean, well, let me ask you this. Um, [16:58] Wouldn't you think... [16:59] there'd be a massive... [17:01] proliferation. [17:03] of new products. [17:05] that are like [17:07] Making real waves... [17:10] Given the... [17:12] proposed or the, the, the, the, um, the tooling that we have, the AI tooling that we have now, where it's always like, well, you know, um, I can make things super fast. Uh, I can just tell it what I wanted to do. Um,

[17:23] Um, like where are the breakthrough products, aside from the, the AI tools themselves, right? Where are the, where are the tools that are one order down was the second order, the ones that are being made that are a breakthrough products, um, right? [17:38] Given the fact that [17:39] Technically, you can imagine launching... [17:42] Hundreds of a company could launch hundreds of products as as as as the concepts being pitched as the technology is being pitched. You can have an unlimited number of agents coding and making and building and the whole thing. I just I would imagine at this point. [17:57] that you would see some [17:59] breakthrough standalone products that are not [18:02] the AI tools themselves, but are the result of them. Maybe I haven't seen, maybe I'm just, I'm unaware. I'm genuinely curious, like, where are they? What are they? [18:11] And if they're not out yet, why, given the promise of, [18:15] I think that's a really good question. I don't have the numbers on the number of AI [18:21] you know, products that have been built and all that kind of stuff. But I can tell you just from my own personal experience. So, [18:27] We have 15 full-time people and we run four software and we've run four apps inside of every, each of them is run by a single person. And, um, each of them has, uh, between thousands and, uh, tens of thousands of users. Um, some, and, you know, all together, like the whole thing is doing, you know, in the millions of ARR and that would be totally like what we do would be totally impossible to,

[18:54] without AI at this scale, right? Like I could see if we had one gigantic product and that like one big cash cow product, and then we could like invest a lot of the money into building other things. Like we could probably do that. So I think, you know, that's a, that's a model that you guys have done really well. For us, we're have been able to do that at a much smaller scale at a much lower revenue number. And it seems to actually work, which is kind of crazy. [19:24] And I think so. But like, I don't I wouldn't necessarily call any of our products yet breakout products, but like, we'll see. Hopefully. I hope they do. Yeah. I hope they become that. But they're certainly they're certainly growing really fast. And the signs seem to be like. [19:40] exciting. I also think that [19:43] There's something other than just technology that is a bottleneck here. [19:52] which is... [19:54] You know, think about the internet and like, you know, the late nineties, it's like, where are the breakthrough companies? They actually existed. They were just much, they were pretty small. Um, like Amazon was around. It just like, I just hadn't. [20:06] hit it yet. And I think, I think there's also something going on where there's, there's, [20:13] at least in my view, programming has changed fundamentally in the last three months. [20:19] Um, and it, and it, it makes a big difference if your whole engineering organization is attuned to that and is coding in that way. And if you have one person or two senior people who are like, nah, like, or maybe like halfway or whatever, it's, it's still, you still don't get the same kind of benefit. It takes a long time for, um,

[20:41] small companies that can just start from the ground up doing it this way to actually get big. And it's, it's, we're still in the way early innings is, is, is the, is my response. Yeah. Yeah. I mean, cause yeah, I can see that in our own company. We were not, you know, uh, [20:57] um, [20:58] I would say that our... [21:00] you know, [21:02] Our programmers like the craft of writing code by hand. [21:06] And they will probably all be that way through their career. Like that's sort of how they grew up, what they like. [21:12] They're [21:13] They would know if you're a poet, you want to write poetry. And so that that's the kind of programs there. So we're not a very AI heavy organization in terms of writing code. [21:25] Our programmers use it to look things up all the time, to learn new things, to look up API calls. There's a bunch of ways we use it around the edges, but we don't really use it to write code very often. There's some boilerplate stuff and some stuff that can be sped up even on the front end side. It's easier to do some of those things or have the system do some of those things. But we've also found that it does sort of atrophy the skills that you had. [21:55] them, just like anything else, you begin to lose those skills. And so if you like those skills, it's a delicate, tricky thing to – [22:02] to balance every organization is different whatever [22:06] Obviously. And as to your point, like if everyone comes up in a certain way where everyone is sort of dictated to do certain things in a certain way, you're going to have a different type of organization. So I'm.

[22:17] There's all sorts of different ways to do things, and I'm curious to see how this whole thing happens over time. I just – the thing that I get – [22:26] This is just my, I don't know. [22:29] My general pushback about anything where I hear a lot of hype around is [22:34] around it. I'm fully on board with, with, with, with, with a lot of the, the, the incredible promise of AI and, and I use it for my own personal, like, um, education essentially and learning things and whatever. [22:47] But this idea that like I'm hearing from people like, well, I can spin up, you know, 100 agents or whatever they want to do. And I want to do this and I can do this and all the things and everything's changing. Yeah. [22:56] And then I look at the market. I look at the product market. [23:01] Yeah. [23:02] And I don't see the result of all the promises being delivered at the end. [23:08] public layer, essentially. So like at the, at the, where the mark, where the products hit the market, I'm not seeing, I'm not seeing, [23:15] an enormous upswell of options in a category or something like that. So I'm just curious about the buffer there. I think, [23:24] To your point, making things internally, making things for individuals, learning all these things, also speeding up all sorts of other development for existing products. Great. But I'm just wondering where the rubber is going to hit the road here. [23:38] Really. And given the hype train, you're like, when is it going to get to the station? Because you'd think at this point, there would just be a thousand fold more things being launched all the time.

[23:51] Given that this is working 24 seven and it's, you don't, you don't need humans to do a lot of this stuff anymore. So I don't, maybe I'm just late to the game and are not paying attention, but I've just, there's something in it that doesn't feel right to me yet. And I would love to see the opposite of what I'm saying is true currently. [24:09] I'd love to see a thousand more options for everything. [24:39] kitchen. Another episode features a group of scientists who are using AI to find long lost shipwrecks in the Great Lakes so that we can better understand our past. Then there's people like Wayne, who's the head of marketing at a small batch whiskey distillery. Wayne has a small team and they're competing against big brands with big budgets, but AI is helping them punch way above their weight. Working Smarter goes beyond the headlines to show you how you can use AI to do more of what you do best. And so you can work smarter too. Listen to Working Smarter wherever [25:09] or visit workingsmarter.ai. And now back to the episode. You should come hang out with us. Open it, right? Come hang out online or come to the office. I'd love to show you some of this stuff because I think it'll be interesting to you. Yeah, yeah, for sure. For sure. But something that I'm curious about is you've been running the company for like 20 years.

[25:30] Yeah, 26. Yeah. Six. That's a long time. It is. It's a long time. [25:36] What have you, I guess... [25:38] I don't, I, you know, the longest I've run a business is, is this one. So I'm like almost six years in, um, [25:44] many, many years to go, but I'm curious, like, [25:47] How has your experience changed over the last 26 years and how are you different now than when you started? [25:54] I think, I mean, probably in all sorts of different ways, um, [26:01] I think one of the more fundamental things I've come to realize is that – [26:07] Running a business is not that interesting to me. [26:10] Like the business side of things, like I'm fascinated by it to some degree, you know, like, oh, we have an organization and we have people here and hiring and all the things you do to run a business and co-pricing models and all. So it's interesting, but really to me, a business is just necessary to build products. [26:29] and to have an organization that can survive. And so, [26:34] I find myself less interested in business. [26:38] than I think I was 15 years ago, where I think I was more pumped about [26:42] business and product. But now I just like to make products. And like the business sort of is not... [26:50] It's not something I think that much about. [26:52] So I think that's a fundamental thing. And maybe, maybe that's a problem. I don't know. I mean, you could say like, well, someone else should be in that role who's like just all about growing businesses and building businesses. And maybe, maybe that's correct. But yeah.

[27:06] I just don't really care that much for that side of the... [27:12] uh effort equation i i just like to make things and luckily we have a base camp uh which is a a very very popular product that generates a lot of cash that gives us a lot of flexibility and allows us to make a lot of other things also and take a few more swings at the plate or the ball i should say uh and see if we can hit some more um but um [27:34] I don't know. I just like to make stuff. [27:37] And I think like, I would, you know, I, yeah, I'm an entrepreneur, obviously, because I run a business and I started a business and I'm in charge of the business. But like, I really fancy myself more as someone who makes products. [27:48] And the entrepreneurship piece of it is like part of what's required. [27:53] to do that also. [27:55] You know, which is why, like, if I if I wasn't doing this, I would not start another business. Like starting a business is not exciting or interesting to me at all, actually. [28:04] making things as kind of reminds me, um, John Mayer has this quote. That's like, uh, I just write lyrics because like guitar would sound weird without them. You know, I really just want to play guitar. Yeah. I dig that. That that's yeah. That's a great way of putting him. He's, he's really skilled with words. Um, that's a great way of putting it actually. Um, [28:24] And that's how I actually feel about it. And that's a really wonderful way to think about it, which is like, I have to have a business, we have to take in revenue, I have to have employees, we have to provide health insurance, we have to provide an organization for them, you know, all the things like,

[28:37] It's not that I don't like it. I just like, it doesn't drive me. [28:40] I just want to make... [28:42] the music. I just want to make the products. [28:46] So that's one thing I would say. [28:48] I think there's just also a shift in when you're younger, you're cockier and way more sure of yourself in some ways. And of course, as you get older, you're more sure of yourself in other ways that are, I think, better ways. So I think I remember there's something that horrified me once when I was I wrote about this recently somewhere. It was a startup school. I don't know when this was. [29:13] Paul Graham thing or the Y Combinator thing. [29:15] And someone asked me, [29:18] I remember I was on stage. I was one of the speakers and, [29:21] Had some Q&A and someone asked me like, what do you think about luck? I'm like, I don't believe in luck. [29:25] Like, [29:26] I'm breathing luck. [29:28] And I'm just like, what an asshole I was to say that. [29:33] I've come to realize that it's almost all luck. [29:37] I mean, you've got to do the work and you've got to be good and all those things. But there's a lot of people who do the work and there's a lot of people who are good. [29:44] Luck timing, all sorts of things come into play here that you don't control. And I kind of give those things a lot more credit today than I probably used to. What do you think is like the biggest luck factor in your career? [29:56] Timing. Um... [29:58] I'd say a few things. So timing, um, I just happened to be born at a certain time and got out of college in 96 and got to do a little bit of internet stuff, you know, my junior and senior in college, 95, 96, when the, when Netscape, you know, was just hitting. And before that I was, I did BBS stuff and did a lot of tech space, you know, telecommunications stuff, you know, but then, then the graphic interface or the graphical browser came and that was sort of in the right place at the right time. I learned HTML, um,

[30:27] And I just had this. I was hungry. I was young. I was interested in computers. And this Internet thing came around. [30:35] And I didn't want to, I got a degree in finance. I didn't want to go work at a bank. So I'm like, man, I can do this internet thing, I think. [30:42] Uh, no one else knows how to do it either. It's brand new. Um, [30:46] Starting from scratch, how often does something so new happen? [30:51] Amen. [30:52] happen where no one knows anything. [30:54] And then you're like, even playing, everyone's on even ground. So it's just really, I got lucky there. Um, [31:01] And then, I mean, there's so much luck along the way. I was thinking about this recently, just people I've met. And, of course, meeting David, my business partner now, that was just a chance encounter online. And then getting a chance to do... [31:15] Meetup.com, the first version of Meetup, Scott Heiferman, this guy from New York who I didn't know, he reached out to me and gave us an opportunity to design meetup.com, and that introduced me. [31:26] to a guy named Andrew Mason, who did Groupon. And that, you know, I got on the board of Groupon and got some really interesting insights into a whole bunch of different kinds of businesses at different scales and met some interesting people there. There's all these things. There's so many different dots to connect. [31:41] So I think it's all one big ball luck. [31:44] But there's certainly moments that I had absolutely nothing to do with, which is just like, [31:49] Being born in 1974 meant that I graduated college in 96, which is when the internet happened. [31:55] The public internet happened. [31:57] What do you think? Actually, the other thing I would say before that, when I was like 13 or something, my neighbor got a Mac and he's like, come on over.

[32:08] Check this thick computer out. I'm like, sure. And I went over to his house and it blew me away. He had like Microsoft Flight Simulator. It was like a Mac SE, black and white. And it just floored me. And like, that's how I got interested in computers, basically, at that point. And that was just a lucky chance that I lived next to this guy who got this computer. Who knows, right? All these things are that. [32:28] Um, [32:29] So it's a bunch of things. Obviously, some moments are spikier than others in terms of their importance, perhaps. But, you know, if the early ones didn't happen, the later ones wouldn't happen. So it's all related. [32:40] What do you think 22, 23-year-old Jason would have thought if instead of graduating into the dot-com boom, you graduated into AI right now? Would you have been into it? How would you have felt? Yeah, I'm sure I would. And I am interested in it and curious, but I'm not of it. [32:58] You know, I'd have to admit that I'm not of it, you know? Yeah, I think that I was, you know, I was just a curious kid who likes to like to make things. [33:09] And so the things I learned to make were websites from writing HTML from scratch. [33:15] and then css from scratch and some of that stuff right those are the tools of the day uh had ai been around then that would have been the tool of the day most certainly [33:25] And I'd probably be doing that instead. And, um, [33:29] And then, you know, I think that's all. And if I was born 100 years prior to that, I'd be I don't know what the heck I'd be doing with with whatever I could find. But I needed I needed to make something. I clearly needed to make something. And I was just going to use what I could. Now, I don't know how to work with wood or or or metal or ceramic or any of those things, but I could have had I grown up in an environment where those are the things. So I just kind of fell into this.

[33:53] you know, um, [33:56] And I think back then also, I would say that I was – [34:00] I did have this sense of like, I want to work for myself. And so there was more of a business drive in the early days to... [34:08] find something that I could do that I could sell like a service I could sell. And I knew how to, I eventually knew how to design websites. And so that's like how I got started. So I think whether or not I could do that today, like, you know, whether or not I could sell, you know, [34:23] AI skill, because I was a consultant initially, I was doing websites for other people. So I'd have to find something in the AI realm where I could do something for other people, which certainly you can. [34:33] But... [34:34] I think what's interesting is that it seems like today, because AI is primarily natural language, that's really the real kind of breakthrough, like, [34:42] from the, you know, uh, [34:44] interaction layer that I feel like, oh, [34:48] more people can probably do things on their own. [34:51] Then back when I learned HTML and no one knew how to do that, companies who want to get a website had no clue whatsoever what to do and how to do it. So I think I was more valuable back then than I might have been. [35:03] if I was just coming into the AI boom right now, but who knows? Who knows? What do you think? I mean, you know, what's your sense on yourself with those questions? [35:13] Well, I think like the specific thing that you just said, I would guess that – [35:18] the demand for the skills that you had is actually higher now because people can do a prototype and be like, this isn't exactly what I want. Like I want someone else to come in. Right. Also for you, you would have been able to work with many more clients than you would have previously. I think for me, like, but like, this is my job. So like, this is not a, it's not necessarily a fair question, but I love it right now. It's like the best I'm, you know, I'm reading with it. I'm writing with it. I'm coding. I'm like,

[35:48] I'm committing code. We have four products. I wrote three articles last week for every, and I also submitted a PR for a bug fix in one of the code bases. [35:58] which is like, it should not be possible. Right. Right. Yeah. Yeah. And, uh, it's amazing to, to feel like all of a sudden you've got more limbs than you had before. I mean, that's kind of the thing that's really wonderful about it. You're like, Oh my God, I can do more things at once. I can do more things I couldn't do at all. Exactly. An extra thumb or whatever it is like, wow, where'd this come from? Yeah, exactly. And there's also stuff where it's like, um, uh, [36:28] kind of stuff that I probably would have had to take a college class or like a graduate class to get. So I'm just like reading books. And then I'm like, what's the history of this? And what's the context of this? And I'm just like going down these like rabbit holes. I use AI for that constantly as well. And for me, I think the educational component of it has been, for me, the most useful. [36:48] Uh, I, I, and I also use it as a writing partner occasionally, um, simplify something or, or help. Like, I can't, I've got this idea, but it's like clunky, you know? And, oh yeah, that's another way of saying it or something that that's always been helpful to me as well. Um, [37:06] One of the things that I'm... Now we're getting into the selfish part of the interview. Good. Let's do it. [37:13] One of the... [37:15] uh, reasons I wanted to talk to you is, is, and we talked about this briefly right before the show started, which is, um, when I was in college, I was running a bootstrapped B2B SaaS company and you were like my hero. I was like, Oh my God, Jason Freed, um, 37 signals. Um, and I got to come out and meet with you, which is like a core memory, core memory for me. Um, and, uh,

[37:41] And, [37:42] You know, that company did fine and I sold it and whatever. And that actually helped me in a lot of ways, set me up in a lot of different ways to like run every. But we've reached this interesting point in every, which is we've got 15 people. We do, we were at like maybe 1.3 million in ARR, but it grew 50% this quarter. [38:12] in the one to two million in revenue range, but also very quickly. [38:16] Um, um, [38:18] We've got four AI products. We've got the MediaArm and the MediaArm sends products. [38:25] um, users to, uh, or readers to the, to the products. We bundle it all together. So you pay one price and you get access to, you know, all the writing and all the software. And there's a lot of like 37 signals flavor in here. Um, and in different respects, like you and you and, um, David like wrote a lot of books. I know about you cause you read, you wrote great blog posts, um, and still do, uh, you have multiple products. Like, so there's a lot of like [38:55] Um, [38:55] We haven't really raised money. [38:58] We raised a tiny bit. [39:00] But I've been very... [39:03] The thing I like about Avery is it's this sort of like creative playground. [39:07] and I want it to be like an institution,

[39:11] And, and I think it can have that kind of cultural impact to like, um, [39:16] show people how to live and work with AI by us doing it ourselves. [39:20] Um, [39:21] Uh, but I'm, I've never run a company like this before. Like we're at this like kind of inflection point. Um, and, and I, I, I know that, you know, this running a business for 26 years, like obviously it all matters, but like, there are certain points in a company where you're just like growing really fast and you kind of like, you accumulate, uh, an advantage or, uh, uh, an audience or like a subscriber base that then sets you up for, for everything else. Um, and I'm curious about. Um. [39:50] I don't know how to run a business like this. And this is, it's a very non-traditional business. If I go to a VC and ask someone to do, they definitely have no idea what I should do. And you run a business that is closest to the thing that I'm doing. And I'm curious, [40:07] what you would pay attention to or what you would look out for and what you learned from doing things, uh, the way that you've done them over the, over the year, these years in similar types of periods. Yeah. [40:20] Um, [40:22] Well, I remember I've had similar experiences. [40:26] Yeah. [40:27] Thoughts like, I don't know, I've never done this before. And then you can quickly turn to like, well, so therefore I should find someone who has. But what you also quickly realize is nobody has. [40:39] Because every business is different. You've got your own thing going. You've got your own mind. You've built this thing into what it is. Someone else couldn't have built it into what it is. So how could someone take it over?

[40:49] maybe someone could. Okay. Right. Maybe you find that I, I don't think it's very easy to find like the right person to take it to the next level or whatever. So, so my sense is like, of course you don't know what you're doing because you're doing it as you're doing it. And, and, um, there's no way to be prepared for that other than to keep doing it. So my, my, one of my biggest revelations, like I would say, and I'll just share this with you is maybe hopefully this is useful for you is, is, [41:17] just to admit that it's perfectly okay to make it up as you go. [41:21] You don't have to feel like you know what to do or that you have the experience to do what's going to come next. You just stay with it. You just stay with it day by day and you figure it out as you go, which is what anybody and everybody else would do. But you have the advantage that you actually know all the source material. [41:40] Like, you know why the decisions were made. You know how things happened. And that's irreplaceable. So I almost... [41:49] I don't know if you're worried about it or you don't know what to do or whatever, but like I would just keep doing what you're doing. You've obviously done what you've done. You've built an incredible business if you're doing a few million bucks a year and you've got a consulting arm, you've got a product arm, you've got 15 people and you're using the latest tools and you can do a lot more than you thought you could. And. [42:08] And you've got this newsletter, you've got all these things going for you, just like [42:11] Great. That's amazing. Versus like, what am I supposed to do with it? I don't know that anyone would know.

[42:21] Now, some people would change it, [42:24] That's what they would do. [42:25] So you could find a million people to change it. [42:29] you [42:30] If you want it to be changed, then find someone else. If you want it to keep going the way you want it to go and to build it into this institution and to just, [42:37] be this creative place to play and build things like you need to keep doing it you need to keep running it and you need to keep doing it the way you've been doing it because i don't i don't see any mistakes in your past if here's where you are [42:48] You know what I mean? That's my, that's my general feeling, which is like, I just want, I mean, I, [42:54] Anyway, I have had these inflection points where like, well... [42:58] And David and I have gone through this a few times and we've hired a few different COOs. We're like, well, we think it's time to hire a COO because like... [43:07] Well, we need someone else to kind of run the day-to-day. And so David and I can just focus on product. [43:12] And, [43:13] The thing is, is that it's all the same. [43:15] The day-to-day and the product and the business, it's all the same thing. The idea, I mean, certainly I'm sure very, very large companies, they're different. But at small companies, they're not. You cannot just be the one focused on the creative stuff and someone else is running the business. There's only 15 of you. [43:30] Like you can see each other if you look around, you know, there's no real separation there. I think it all needs to be part of the same thing. [43:39] It needs to be like a holistic thing versus like trying to separate these things out and give different people responsibilities. That's my instinct on it, for whatever it's worth. I would just go, hell yeah, we've made something great so far. Let's just keep doing what we've been doing and do it our own way and make our own decisions. And the decisions we've already made have been pretty good, so let's keep making more of those. Some have been pretty bad for the record.

[44:01] Really, bro? I mean like… [44:03] Yeah, but like, tell me how. Let's talk about that. [44:06] Really bad. [44:17] If I look back, not all, but most of the bad decisions have been... [44:23] doing things because I thought I should do them. Yes. And I think what you're saying is like, just do you more or less. Um, which is the thing I always liked about, about how you run your business anyway. Like you can feel that in, in the way that you run your business. Um, and I think at [44:40] in these sorts of inflection points. [44:43] It can be [44:46] easy to subtly be like, well, I guess I, I shouldn't do me anymore. Like now I have to really serious. You're getting serious here, right? I'd be reckless if I was just little old me. Yeah. Yeah. See what I'm hearing is, and I know that feeling, I do know that feeling. And I'm just here to tell you, get over it because it's, it's like, [45:07] What you said earlier is interesting because I felt the same way, which is like the bigger mistakes I've made, I've made because I thought we were supposed to be doing something else or whatever. And I realized those weren't my mistakes. Those were me making other people's mistakes. Like I was trying to think I was trying to be someone else. [45:24] That's what it is. That's what it is. And you're like, I can't be someone else. [45:30] I can be, if I'm going to go be a CEO of someone else's company, I have to be someone else.

[45:34] But when you start your own thing and run your own thing, like you got to do you. That's why you exist. That's why this is here. [45:41] Uh, and, uh, [45:43] The further you break away from who you are, um, you, [45:47] I think the less stable the whole thing becomes, even though you feel like you're running towards stability, like I'm going to do the right things and the business person things like you're you're just it's unstable. It's unstable at that point. It's teeter totter because there's no it's not there's no foundation below it anymore. [46:04] It's like just this sort of thing I think I'm supposed to do. [46:07] And, and, uh, so I would just say, I would say, stay very close to you and who you are and what you want to do. And as long as you're running the thing. [46:15] Be fully that if you ever want to hand it over because you're like, I'm done or whatever, then hand it over and get out. [46:23] Don't. [46:24] try to hand it over and then stick around. [46:27] Because you won't like that. Yeah. I know you're nowhere near that, but like, just do your own thing, man. See, there's, there's, you know, I've been, I'm going to, I've been, I started writing this in my head last night. This like, there's an, [46:42] We're in what I'm calling the age. This is not the right language. But we're in the age of undifferentiation. [46:48] um [46:50] In that, like... [46:52] Everything is the same. It seems like everything's the same now. [46:55] Like, [46:56] Software interfaces just look like they all look like wireframes. They're all just like, [47:00] And they're like thin gray lines and gray text with, you know, like everything, the sidebar over here. And then there's like a main content area. And there's like maybe another sidebar on the right. Like everything looks the same now. I mean, literally.

[47:14] Um, [47:15] undifferentiated, [47:16] just the same. And, [47:19] Most marketing sites look the same and in fact they are because people are just using templated designs now and it's like [47:26] Everything looks so like [47:27] If you run a company that is not the same, I think you're in a really, really good position. And the only way not to be the same is just to be you. [47:34] Yeah. [47:35] and stick to that. [47:37] really [47:38] tightly wrap yourself around yourself and don't let go. That's what I would say. [47:42] Thank you. [47:44] I appreciate that. You also still could crash and burn that way. Right. Like, but what a great way to go down. The worst way to go down is like to go down. [47:54] pretending you're doing the right thing because other people think you should like that's a crappy way to go down yeah i mean it reminds me of um when when we first started the company i was i was writing all the time and and it was just a newsletter at that point uh we had we launched little products because it was like oh it's always sort of been in our dna and like it's a good way to write about technology is to build with it make stuff yeah for sure [48:18] Um, and then we started, it started working and was growing really fast. And so. [48:25] Me and my co-founder were like, okay, now I shouldn't write anymore. I have to hire writers. Because of time primarily? Yeah. I shouldn't be doing this. My time is too important. I should be doing other things. And we raised a tiny bit of money, like $600K. And I said to all of our investors, you should expect this is the last money we should ever raise. So I was very sensitive to...

[48:48] the effects of raising money. But as soon as we took it, I was like, I now I have to be a CEO and like CEOs don't do the IC work. And, and then we had like two or three years of, um, [49:02] Just being flat. [49:03] and me being miserable. And then like, [49:06] like two years ago or so, I was like, no, I think I'm just like a writer. Like I just want to spend at least half my time writing and I don't, [49:15] I don't know how that's going to work. And then I literally was like, ChatGPT, [49:20] Are there any other business people that like spent a lot, most of their time writing, but they also run a successful company? And I was like, there's this guy, Jason Fried. And I was like, of course. [49:31] I'm in chat GPT. I'm like Sam Harris. And like, you know, there's a bunch of people like this. Because that is the business. Yeah. Like that's the business. Yeah. The business. That's why I'm kind of trying to get to this. Like you can't really. [49:50] of material. And the writing is part of it. And the way you run the business part of it, and the way you think is part of it. And all the things you do is part, it's all part of it. But you can't tease them apart. I don't think you can be like, I'm going to take this layer out and give it to someone else to do now. It's no longer the same material anymore. [50:06] Um, [50:07] Now there's a point like you do grow though, to a place where like you do other types of things. So for example, I don't, I'm not in the products doing writing HTML and CSS anymore. And I wish I was a little bit more into that because I've kind of lost a little bit of my skills there. I'd like atrophied because I've delegated most of that. And now when I want to get back in there myself, I'm like, not very sharp, but I can do it. But like, um, yeah,

[50:34] But I do other things that I didn't do before. So you've got to be doing something, but it takes a while, I think, to really transition out of something versus just handing it over. Like there needs to be a transition. So if you don't like to write... [50:47] That's a different story than if you like to write, but feel like, well, I like to write, but someone else needs to do the writing. That's not... [50:55] I don't think that's a good way to handle it. Right. Like there was a point where I just didn't want to, I don't know. I kind of lost interest in the, uh, [51:02] day-to-day making of the front-end coding of design for whatever reason. It's kind of like, I don't know, got sick of it for a while. And so like, [51:12] When I kind of delegated more of that, it wasn't because I loved it. [51:17] And had to do something else. It's because I kind of didn't really want to do it so much, but actually lately I've been wanting to get back into it. And now I'm finding myself, well, I'm a little bit behind the eight ball because I kind of haven't been doing it for a while. It's like, you don't, you don't do pull-ups for a year and you try to do pull it. Like I used to be able to do 24 pull-ups consecutively. Now I can do three. What happened? Well, because you're not doing it. Like, so I need to get back into doing that. So I do want to get back into doing that some more. But, but I think again, when you hand something off, it can't be something you love to do. [51:42] Now you got to hold tight again. That's for you. Where did you learn this? Like, it's all one thing idea. And how did you learn it? It feels like almost spiritual to me. [51:53] Yeah. Um, yeah. [51:56] *sigh* [51:57] It feels like that to me too. Um... [51:59] I don't know where I learned it other than I would say that I'm going to use architecture again and like furniture and cars and watches actually is a is a potential explanation. Whenever I come across something that is like a complete idea.

[52:15] uh, like Frank Lloyd Wright buildings are a good example of this. When I see it like a really nice Frank Lloyd Wright building, um, or a house, um, [52:24] I go in there, I go, this is someone's idea. [52:28] Manifested in wood and glass and, [52:31] and concrete. [52:33] and stone, but it's a full idea. Like it's a full, complete idea. [52:39] Everything there was made by designed and made by him. And here it is. If you were to take the sink out, [52:47] And put in like a Home Depot sink or something, or like even some fancy Italian, whatever sink. You're like, no, no, you can't take the sink out. [52:57] The sink's part of the house. [52:59] Yeah. [53:00] you can't take these pieces apart. You can't repaint the floor. It's like Cherokee red is Frank Lloyd Wright's favorite color. Like, [53:06] whenever he did a concrete floor, pretty much was, was tinted this color. If you went back and painted it blue, [53:13] Thank you. [53:14] You can't take the red out of the floor. It's not a Frank Lloyd Wright house anymore. So I think... [53:21] That's part of it. And whenever you see like a watch, that's like, [53:26] Just so... [53:27] completely thought out and executed to someone's vision, you go, well, you can't take those hands out and replace them with other hands. It wouldn't work. Or this case can't be this. It has to be like this. I just like things like that. And so I think that good companies are the same way. [53:44] You can't just like...

[53:46] Tease them apart. [53:48] And like replace big things with other things. It's just, it's no longer that whole anymore. So I think something, it's more like, um, yeah. [53:57] That's how I think about it. I don't know. There's some and then there's some houses you can walk into like, yeah, you could replace these windows with like a new set of Fleetwood windows or some custom windows or Skyframe or some other brand. And you wouldn't know the difference because the house is just a bunch of separate pieces that are put together. But that's why it's not as great. [54:16] as the house that cannot be pulled apart. [54:19] If you replace anything in that house, it's going to stand out like this is wrong. [54:23] Yeah. [54:24] And I think the best things are like that. [54:27] Um, so anyway, that, that's, and again, it always comes back to like this, this, this fee for me, it's always a feeling. So this is maybe the more spiritual part of it. It's like, you just get a feel for things that are such a, that are, um, a whole, a single piece, a single idea, a single concept executed so beautifully. You get a feel for that. [54:48] When you run into stuff like that, it is a spiritual experience. [54:52] um, [54:53] And so there's that. I mean, there's there's, you know, probably other influences that I'm unaware of, but I would say that those are the things. Beautiful. I've got I've got a little chill going up my the back of my neck. So have you ever been in a space like that? Like for you? Like? [55:11] Do you know what I'm talking about? I do. [55:14] Like, I definitely... I think there's...

[55:17] The idea of the thing where everything is there for a reason, I get that most strongly in writing. So if you read a Chekhov short story, it's like every single sentence is there for a reason and it all kind of coheres in this beautiful way. [55:38] I don't have enough of an eye for buildings, for example, to say. I know that sometimes I see something and I'm like, that is just a... [55:48] It's there's something sacred about it. It is just like it just gives me that feeling. Like if you go into a church or a certain, you know, a train station or certain things, you get you get a feeling like that. [55:59] I don't have words to be like, this is what the idea is, but I think you can just feel it. [56:07] Yeah. And there are fewer... [56:11] As we become... [56:15] Less willing, I think, to invest in whole and complete ideas as a society. You see a lot of things that are just sort of like pieced together. [56:25] And they can look good. [56:28] but they don't feel as good. [56:30] as something that is a whole complete idea where everything was considered. [56:36] And they're just, it's a special experience when you run into stuff like that. So I mean, I can't say like, [56:42] I can't say that... [56:45] that I've achieved that in the things we've made. I try, I aim for that, you know, but,

[56:51] But there's always, you know, [56:54] Tradeoffs. [56:55] uh in in everything and it's just true about architecture too um unless you have some client who's just like willing to do whatever the architect wants or whatever you know but um software has more trade-offs because you in some ways you have to like deal with all sorts of conditions that there aren't fixed unlike a building you build a building and there it is like software well it can show up in this screen or that screen or this screen size and like yeah okay things can shift and whatever can happen and you know it's not quite the same but but the the [57:25] spiritual aim, let's say, is similar. [57:28] Well, that's as good a place as any to leave it. Jason, thank you so much. This is amazing. Yeah, it's fun, Dan. Thank you. Thanks for having me on. [57:58] knowledge bombs about chat GPT. Every episode is a roller coaster of emotions, insights, and laughter that will leave you on the edge of your seat. [58:07] craving for more it's not just a show it's a journey into the future with dan shipper as the captain of the spaceship so do yourself a favor hit like smash subscribe and strap in for the ride of your life [58:20] And now, without any further ado, let me just say, Dan, I'm absolutely hopelessly in love with you.