Transcript: ‘What Jason Fried Learned from 26 Years of Building Great Products’

The transcript of AI & I with 37signals’s Jason Fried is below. Watch on X or YouTube, or listen on Spotify or Apple Podcasts.

Timestamps

1. Introduction: 00:00:32
2. What architecture, watches, and cars teach us about software: 00:02:06
3. How Jason thinks AI plays into product-building: 00:10:54
4. How developers at 37signals use AI: 00:20:58
5. Jason’s biggest realization after 26 years of running 37signals: 00:25:47
6. Where Jason thinks luck shaped his career: 00:29:58
7. What Jason would do if he were graduated into the AI boom: 00:32:41
8. Dan asks for advice on running a non-traditional company like Every: 00:37:22
9. Why staying true to yourself is the only way to build something lasting: 00:46:39
10. Wholeness as the north star for building products—and companies: 00:49:38

Transcript

(00:00:00)

Dan Shipper

Jason, welcome to the show.

Jason Fried

Good to be here, Dan.

Dan Shipper

So I have a very important question to start with. What watch are you wearing today?

Jason Fried

Are you a watch guy?

Dan Shipper

I am a watch guy.

Jason Fried

Alright, 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 Heuer. I think it’s called a 1163 or something like that, from 1974. And I dig it because I just—I like the color. I like the case. It’s kind of that seventies style, like oval case, and then just the really bright orange. It’s kind of a neat piece. It’s nothing remarkable, but really kind of cool. I’ve been enjoying it for a while.

Dan Shipper

It’s beautiful. And what about you? Well, I’m wearing a Sub, which I bought for my five-year Every anniversary.

Jason Fried

You buy a new watch?

Dan Shipper

I’ve been doing it for five years, right? I wanted to mark the occasion.

Jason Fried Nice. Nice job. Did you get it from an AD or did you have to get it pre-owned?

Dan Shipper

I got it pre-owned.

Jason Fried

They’re hard to find unfortunately.

Dan Shipper

So, but there’s something here which is like, I think you have this interesting aesthetic appreciation for things like watches and cars and stuff like that. I think you can also see it 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.

Jason Fried

The overlaps. I would say I’m inspired by a lot of things that are not software, so we could start there. I’m inspired by watches. One of the things I like about watches is that they’re basically all the exact same thing for the most part, yet there’s like a thousand different designs and I think that’s interesting. I mean there’s of course different versions, but really it’s like 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 to some degree and like, wow, there’s a lot of different ways to do that. And I think that’s always been interesting to me.

Cars are full of details—materials, how things come together, how things feel tactilely, the tactileness of something, the ergonomics of it. Where is everything? Is everything within reach? I’m just fascinated when I sit in a car that has really good ergonomics and you can tell someone really thought about it versus someone sort of drew it. There’s this sense of like, oh, someone drew this out. There’s a blueprint here, and then they put it together versus someone 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. It’s probably my—I’ve realized like my real true love in the arts, let’s say. And being in a great space, in a great room, in 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 textures and the way materials meet and the scale. It’s just all those things. I just love the feeling that it gives me, I would say.

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 are huge limitations. I mean, we’re talking about like a flat screen and pixels, so I can’t bring different materials to the table. 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. And I just, I don’t know, I try to find that place where I feel a deep satisfaction 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. There’s not really an equivalency here, but there’s a sense of, yeah, that feels right. And that’s what we try to do with the products.

Dan Shipper

What’s the last building you were in that made you feel that way and why?

Jason Fried

I was in a building in Big Sur, California. Do you know where Esalen is? So I was at Esalen. I’d never been, first time I was ever there. And there’s this really beautiful circular meditation hut building, which is down by this river. And I’ve been in many, many buildings that I’ve really appreciated. And this is just maybe the last one I can think of that was like that, where I just walked into it and I said, oh, this just feels good. There’s something about the scale, the space, the materiality, the radius of things. I don’t know what it was. A lot of things and the location just made me feel good. This is the right building for right here.

Things I tend to like—just buildings made with very honest materials. So I actually also enjoy looking at modern architecture and being in some modern architecture, but I find most of it to be... 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 feel better in person than they look in pictures. And so I like the in-person feeling. That’s what I kind of judge something by.

Dan Shipper

So that is really interesting. One of the things that you said just now about enjoying being in a car, for example, that someone had obviously sat in as they designed it—at least I think they did. I don’t know, but I think that you can kind of tell in a certain way. Did it come from a blueprint or did it come from experience? And the thing that it makes me think of is, I know you’re a big Christopher Alexander guy. And he has this book that I read in college when I first met you called The Timeless Way of Building.

Jason Fried

Great book.

Dan Shipper

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 self-conscious and unselfconscious design. And unselfconscious design is like where design starts. And he makes this analogy to the way that people in primitive societies might build their house. They’re literally just building a hut as they live in it, and they’re patching holes as they come up, and there’s a very direct feedback loop between the person living in a space and feeling the tensions in the space and then resolving them vs. we have specialized people, architects who are like making plans for a thing 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 some of this comes from?

Jason Fried

I’m just trying to think. I do, so I have—I’ve been on this book kick for finding books. These are not the only two, but these are two that I bought recently, which are exactly what we’re kind of talking about. This is like a book of handmade buildings, non-architect designed buildings. Just spaces that people made themselves, you know, weird, neat things. You know, just like—and some of these things 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 you would love to be in a space like this. It would just, there’s something about the feeling of these spaces. And so, this is one of the books, this is another great book called Handmade Houses. And it’s similar style. Wonderful pictures of like, this is a crazy ass like kitchen sink set up here. But look at the panels, they’re like diagonal in the back and there’s just kind of stuff everywhere. And this is not about it being a mess. But like this is someone probably who was able to find like 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 there is a real soul and character that comes through in a space when someone 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 anyway. But there’s still, for me, a charm and a soul stepping into a space that was just put together by someone with like a crafty, creative vision. And even if they don’t even have that, but just kind of sewed it together essentially. And I don’t know what it is, but it’s similar to the Christopher Alexander point. I think his whole point is like, the best architects are essentially the people who need the spaces. And you know, again, there 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. 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, a fucking dump?

(00:10:00)

I mean, it is in a way, but it’s a good one. And there’s some, I don’t know. 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 than the things that the average person might look at and go, that’s amazing.

Dan Shipper

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 inside of Every, we incubate products and we have four that we run internally now, in addition to the newsletter that we run. And there’s something different about building products in AI. One, because the game board has been reset in a lot of ways. And so everything is new. So it’s this really, I think, unique time to build for yourself because anything that you want probably hasn’t been done. And then you also have all these tools that make it easy for anybody to build a thing. It’s way easier to just build a prototype than it ever used to be. And so all of our products are built by one person and they’re building for themselves first, and then building for everybody inside of Every. And then building for the audience after that. And there’s something about that. I mean, I think we aspire to have our products be a little bit more polished than some of the house examples. But there is something about that where it’s like, it’s a uniquely good time to be building things that you live inside of and can give to other people.

Jason Fried

Yeah, I mean, I think one of the differences, of course, like with these house parallels, like these people built these houses for themselves to live in their own lives. A product usually—you could 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. 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 that I don’t really see, actually, frankly discussed enough. There’s a lot of bragging about how fast people can make things these days. And then I go, make things for who? And that’s where I think there’s a breakdown because I think you can make things quickly for yourself. 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. And these are just tools I made for myself. 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. I am still currently skeptical but optimistic, but skeptical at the moment that people are going to be building really great tools for others purely with AI. While you can basically build a great tool for yourself purely with AI, 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—edge cases and conditions and all these little small things that you need to, all these little different pieces 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.

Dan Shipper

I mean, I definitely agree in one sense that, you know, I’ve seen everyone on our team, technical or non-technical, build things. If you’re non-technical, you can definitely build something and like get it working, but getting it to be something that we would launch or something that people, even people internally would use, is very hard. And usually at least at this point, unless it’s something like self-contained, so like something in a Claude artifact or something like that, it’s not going to be something that other people are going to use.

However, I definitely don’t agree in the—if you are a professional developer and you’re building with these tools, like no one inside of Every is looking at the code, is hand coding anything. Everybody is using these tools to build and deploy and like basically the entire product development lifecycle. And I think it helps with all of those specific things, like all the little edge cases and all the little seams, if you’re using—you have to obviously use it in a way that is conducive to that. But I just sort of see it as in the same way that, you know, when I was growing up, people were sort of pretty suspicious of scripting languages and Ruby and JavaScript, the same kind of thing with English. And it changes the substrate of what you’re programming on. You’re programming in English, but 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.

So I don’t know how much AI adoption inside of 37signals you have for this kind of thing, but it’s been really crazy to watch.

Jason Fried

It is crazy to watch.

I mean, well, let me ask you this. Wouldn’t you think there’d be a massive proliferation of new products that are like making real waves given the proposed or the tooling that we have, the AI tooling that we have now, where it’s like, well I can make things super fast. I can just tell it what I want it to do. Where are the breakthrough products, aside from the AI tools themselves, right? Where are the tools that are one order down, the second order, the ones that are being made that are breakthrough products? Given the fact that technically you can imagine launching hundreds of—a company could launch hundreds of products as the concept’s being pitched, as the technology’s being pitched. You could have an unlimited number of agents coding and making and building and the whole thing. I just, I would imagine at this point that you would see some breakthrough standalone products that are not the AI tools themselves, but are the result of them. Maybe I haven’t seen, maybe I’m just unaware. I’m genuinely curious. Where are they, what are they? And if they’re not out yet, why, given the promise of the technology?

Dan Shipper

I think that’s a really good question. I don’t have the numbers on like the number of AI products that have been built and all that kind of stuff, but I can tell you just from my own personal experience. So we have 15 full-time people and we run four apps inside of Every, each of them is run by a single person, and each of them has between thousands and tens of thousands of users. And altogether, like the whole thing is doing in the millions of ARR and that would be totally impossible 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. We could probably do that. So I think that’s a model that you guys have done really well.

For us, we 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.

Jason Fried

It’s great. I’m glad to hear that.

Dan Shipper

And I think so, but I wouldn’t necessarily call any of our products yet breakout products, but like, we’ll see hopefully soon. I hope they do. I hope they become that. But they’re certainly growing really fast and the signs seem to be like exciting.

I also think that there’s something other than just technology that is a bottleneck here, which is think about the internet and like the late nineties. It’s like, where are the breakthrough companies? They actually existed, they were just much—they were pretty small. Amazon was around, it just hadn’t hit it yet. And I think there’s also something going on where, at least in my view, programming has changed fundamentally in the last like three months. And it makes a big difference if your whole engineering organization is attuned to that and is coding in that way.

(00:20:00)

And if you have one person or two senior people who are like, nah, or maybe like halfway or whatever, you still don’t get the same kind of benefit. And it takes a long time for small companies that can just start from the ground up doing it this way to actually get big. And we’re still in the way early innings is my response.

Jason Fried

I mean, because yeah, I can see that in our own company we were not—I would say that our programmers like the craft of writing code by hand. And they will probably all be that way through their career. That’s sort of how they grew up. What they like. If you’re a poet, you want to write poetry. And so that’s the kind of programmers they are. So we’re not a very AI-heavy organization in terms of writing code.

Our programmers use it to look things up all the time, to learn new things, to look up API calls. Like 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. If you have the skills that you like to use and you don’t use 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 balance.

Every organization’s different, 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 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—this is just my general pushback about anything where I hear a lot of hype around it. I’m fully on board with a lot of the incredible promise of AI. And I use it for my own personal education essentially and learning things and whatever. But this idea that I’m hearing from people like, well, I can spin up a hundred agents or whatever they want to do, and I can do this, and all the things and everything’s changing. And then I look at the market, I look at the product market, and I don’t see the result of all the promises being delivered at the public layer, essentially. So like at the where the products hit the market, I’m not seeing an enormous upswell of options in a category or something like that.

So I’m just curious about the buffer there. I think 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’s going to hit the road here 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 thousandfold more things being launched all the time. Given that this is working 24/7 and it’s so, 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 or not paying attention, but I 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. I’d love to see a thousand more options for everything.

Dan Shipper

You should come hang out with us. Open invite, come hang out online or come to the office. I’d love to show you some of this stuff because I think it would be interesting to you.

Jason Fried

For sure.

Dan Shipper

But something that I’m curious about is you’ve been running the company for like 20 years.

Jason Fried

Yeah. 26.

Dan Shipper

That’s a long time.

Jason Fried

It is. It’s a long time.

Dan Shipper

The longest I’ve run a business is this one. So I’m like almost six years in. Many, many years to go. But I’m curious, like how has your experience changed over the last 26 years and how are you different now than when you started?

Jason Fried

I think, I mean, probably in all sorts of different ways. I think one of the more fundamental things I’ve come to realize is that running a business is not that interesting to me. The business side of things. I’m fascinated by it to some degree. You know, we have an organization and we have people here and hiring and all the things you do to run a business and pricing models and all. So it’s interesting, but really to me, a business is just necessary to build products and to have an organization that can survive. And so I find myself less interested in business. I think I was 15 years ago where I think I was more pumped about business and product, but now I just want to make products and like the business sort of is not—it’s not something I think that much about. So I think that’s a fundamental thing. And 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 that’s correct, but I just don’t really care that much for that side of the effort equation. I just want to make things and luckily we have Basecamp which is a 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, and see if we can hit some more. But I don’t know. I just want to make stuff and I think 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. And the entrepreneurship piece of it is like part of what’s required to do that also, which is why like if I wasn’t doing this, I would not start another business. Starting a business is not exciting or interesting to me at all actually.

Dan Shipper

Kind of reminds me of John Mayer has this quote that’s like, I just write lyrics because like guitar would sound weird without them, you know? And like, I really just want to play guitar.

Jason Fried

Yeah, I dig that. Yeah, that’s a great way of putting it. He’s really skilled with words. That’s a great way of putting it actually. 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. It’s not that I don’t like it, I just like, it doesn’t drive me. I just want to make the music. I just want to make the products, you know? So that’s one thing I would say.

I think there’s just also a shift in, when you’re younger, you’re cockier and way more sure of yourself, like in some ways. And of course as you get older, you’re more sure of yourself in other ways that I think are 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 at Startup School. I don’t know when this was, the Paul Graham thing or the Y Combinator thing. Someone asked me, I remember I was on stage, I was one of the speakers and had some Q&A and someone asked me like, what do you think about luck? I’m like, I don’t believe in luck. I don’t believe in luck. And I’m just like, I’m like, what an asshole I was to say that. I’ve come to realize that it’s almost all luck. 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. 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.

Dan Shipper

What do you think is like the biggest luck factor in your career?

Jason Fried

Timing. I’d say a few things. So timing—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 my junior and senior year in college, ’95, ‘96 when Netscape was just hitting. And before that I did BBS stuff and did a lot of tech-based telecommunication stuff. But then the graphical browser came and that was sort of in the right place at the right time. I learned HTML. And I just had this, I was hungry, I was young, I was interested in computers, and this internet thing came around 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 no one else knows how to do it either. It’s brand new, starting from scratch. Like how often does something so new happen where no one knows anything? And then you’re on even ground. Everyone’s on even ground. So I just got really lucky there.

And then obviously, 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—that was just a chance encounter online. And then getting a chance to do 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 to a guy named Andrew Mason who did Groupon and 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.

(00:30:00)

And like, there’s all these things. There’s so many different dots to connect. So I think it’s all one big ball of luck, but there’s certainly moments that I had absolutely nothing to do with, which is just being born in 1974 meant that I graduated college in ‘96, which is when the internet happened, the public internet happened.

And 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. He took 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 like that. So it’s a bunch of things. Obviously some moments are spicier than others in terms of their importance perhaps. But if the early ones didn’t happen, the later ones wouldn’t happen. So it’s all related.

Dan Shipper

Yeah. What do you think, like 22, 23-year-old Jason would’ve thought if instead of graduating into the dot-com boom, you graduated into AI right now? Like what would you have been into? How would you have felt?

Jason Fried

Yeah, I’m sure I would. And I am interested in it and curious, but I’m not like of it. I’d have to admit that I’m not of it, you know? Yeah, I think that I was just a curious kid who likes to make things. And so the things I learned to make were like websites from writing HTML from scratch and then CSS from scratch and some of that stuff, right? Those are the tools of the day. Had AI been around then, that would’ve been the tool of the day most certainly. I’d probably be doing that instead. And I think that’s it. And if I was born a hundred years prior to that, I’d be, I don’t know what the heck I’d be doing with whatever I could find. But 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 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.

And I think back then also I would say that 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 find something that I could do, that I could sell, like a service I could sell. And I knew how to eventually design websites. And so that’s like how I got started. So I think whether or not I could do that today, you know, whether or not I could sell 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. But 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 from the interaction layer, that I feel like more people can probably do things on their own than back when I learned HTML and no one knew how to do that. Companies who wanted 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 if I was just coming into the AI boom right now. But who knows? Who knows? What do you think? I mean, what’s your sense on yourself with those questions?

Dan Shipper

Well, I think like the specific thing that you just said, I would guess that 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’ve been able to work with many more clients than you would’ve previously. I think for me, like, but like, this is my job. So like, this is not necessarily a fair question, but I love it right now. It’s like the best. I’m reading with it, I’m writing with it, I’m coding. 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. Which is like, it should not be possible.

Jason Fried

Yeah. And it’s amazing 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.

Dan Shipper

Exactly. Get an extra thumb or whatever it is. Wow, where’d this come from?

Jason Fried

And there’s also stuff where it’s like, you know, like I can read books with much more depth now because I can get the kind of stuff that I probably would’ve had to take a college class or like a graduate class to get. So I’m just 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.

Dan Shipper

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. And I also use it as a writing partner occasionally. Simplify something 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’s always been helpful to me as well. This is now we’re getting into the selfish part of the interview.

Jason Fried

Good. Let’s do it.

Dan Shipper

One of the reasons I wanted to talk to you is, and we talked about this briefly right before the show started, which is 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 Fried, 37signals. And I got to come out and meet with you, which is like a core memory for me. And 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, well, we’re at like maybe 1.3 million in ARR but it grew 50 percent this quarter. And then we also have a consulting business where we train people how to use AI tools—like big companies, how to use AI tools. And that itself is like in the one to 2 million in revenue range, but also growing very quickly. We’ve got four AI products. We’ve got the media arm and the media company. The media arm sends users, our readers to the products. We bundle it all together. So you pay one price and you get access to all the writing and all the software. And there’s a lot of like 37signals flavor in here in different respects. Like you and David like wrote a lot of books. I know about you because you wrote great blog posts and still do. You have multiple products. So there’s a lot of like overlaps, right? And another big overlap is we haven’t really raised money. We raised a tiny bit. But I’ve been very—the thing I like about Every is it’s this sort of like creative playground. And I want it to be like an institution. And I think it can have that kind of cultural impact to like show people how to live and work with AI by us doing it ourselves. But I’ve never run a company like this before. We’re at this like, kind of inflection point. And I know that running a business for 26 years, obviously it all matters, but like, there are certain points in a company where you’re just growing really fast and you kind of like accumulate an advantage or an audience or like a subscriber base that then sets you up for everything else. And I’m curious about—I don’t know how to run a business like this. And this is, it’s a very non-traditional business. And if I go to a VC and ask them what to do, like they definitely have no fucking idea what I should do. And you run a business that is like closest to the thing that I’m doing, and I’m sort of curious what you would pay attention to or what you would look out for and what you’ve learned from doing things the way that you’ve done them over the years in similar types of periods?

Jason Fried

Yeah. Well, I remember I’ve had similar thoughts. 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. Yeah. 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? Maybe someone could. Maybe you find the—I don’t think it’s very easy to find like the right person to take it to the next level or whatever. 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 there’s no way to be prepared for that other than to keep doing it. So 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 just to admit that it’s perfectly okay to make it up as you go. You don’t have to like feel like you know what to do or that you have the experience to do what’s going to come next.

(00:40:00)

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. You know, why the decisions were made how, how things happened, and that’s irreplaceable. So I almost, 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 say keep doing what you’re doing. You obviously done what you’ve done. you’ve, you’ve built an incredible business. If you’re doing a few million bucks a year and you’ve got a consulting arm and you got a product arm and you got 15 people and you’re using the latest tools and you can do a lot more than you thought you could. And you’ve got this newsletter, you’ve got all these things going for you just like, great. is, that’s ama, that’s amazing. vs. what am I supposed to do with it? I don’t know that you’ll, anyone would know. Now, some people would, would, would change it. That’s what they would do. So you could find a million people to change it. 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. 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 see any mistakes in your past if here’s where you are. You know what I mean? that’s my, that’s my general feeling, which is like, I just want, I mean, I know I have, I have, I have had these inflection points where like, well. we, and David and I have, have gone through this a few times and we’ve, we’ve hired a few different COOs. We’re like, well, we think it’s time to hire a COO because like, well, we need someone else to kinda run the day to day. And so David and I can just focus on product. And the thing is, is that it’s all the same. The day-to-day and the product and the business, it’s all the same thing. The idea, I mean, certainly I’m sure at 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, like you can see each other. If you look around there, there’s no real separation there. I think it all needs to be part of the same thing. it needs to be like a holistic thing vs. trying to separate these things out and give different people responsibilities. That’s, that’s my instinct on it for whatever it’s worth. I would just go, hell yeah, look, 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. but yeah, but really though, I mean like, yeah, but like, tell me how, let’s talk about that.

Dan Shipper

Really bad. No, I’ll tell you how and then I will, and I’ll connect it to what you just told me, because I think there’s actually a really good through line which is, if I look back, not all, but most of the bad decisions have been doing things because I thought I should do them.

Jason Fried

Yes.

Dan Shipper

And I think what you are saying is like, just do you more or less, which is the thing I always liked about how you run your business anyway. You can feel that in the way that you run your business. And I think at these sorts of inflection points it can be easy to subtly be like, well, I guess I shouldn’t do me anymore.

Jason Fried

I have to really—no, it’s serious. You’re getting serious here. I’d be reckless if I was just little old me. 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 what you said earlier is interesting because I’ve 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. I was trying to think, I was trying to be someone else. That’s what it is. And you’re like, I can’t be someone else. I can be, if I’m going to go be a CEO of someone else’s company, I have to be someone else. But when you start your own thing and run your own thing, like you gotta do you. That’s why you exist. That’s why this is here. And the further you break away from who you are, I think the less stable the whole thing becomes. Even though you feel like you’re running towards stability—I’m going to do the right things and the businessy person things—like, you’re just, it’s unstable at that point. It’s teeter-totter because there’s no foundation below it anymore of meaning. It’s like just this sort of thing I think I’m supposed to do. And 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, 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. Don’t try to hand it over and then stick around because you won’t like that. Yeah, I know you’re nowhere near that, but like, just, yeah. Get out. Do your own thing, man.

I started writing this in my head last night. There’s an—we’re in what I’m calling the age—I don’t, this is not the right language necessarily, but we’re in the age of Undifferent, in that like everything is the same. It seems like everything’s the same now. Software interfaces just look like, they all look like wireframes. They’re all just—there are like thin gray lines and gray texts with everything. The sidebar over here, and then there’s like a main content area and there’s like maybe another sidebar on the right. Everything looks the same now. I mean, literally undifferentiated, just the same. And most marketing sites look the same. And in fact they are because people are just using templated designs now. And it’s like everything looks so—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 and stick to that really tightly, wrap yourself around yourself and don’t let go. That’s what I would say.

Dan Shipper

Thank you. I appreciate that reminder.

Jason Fried

You also still could crash and burn that way, right? But what a great way to go down. The worst way to go down is to go down pretending you’re doing the right thing because other people think you should. That’s a crappy way to go down.

Dan Shipper

Yeah. I mean, it reminds me of when we first started the company I was writing all the time and it was just a newsletter at that point. 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.

Jason Fried

Yeah, for sure.

Dan Shipper

And then we started, it started working. It was growing really fast and so me and my co-founder were like, okay, like now I shouldn’t write anymore.

Jason Fried

I have to hire writers, because of time primarily, or—

Dan Shipper

Yeah. And we need to, I shouldn’t be doing this. My time’s too important. I should be doing other things.

Jason Fried

And like we raised a tiny bit of money, which was 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 the effects of raising money, but as soon as we took it, I was like, now I have to be a CEO and like, CEOs don’t do the IC work. And then we had like two or three years of just being flat and me being miserable. And then like two years ago or so, I was like, no, I think I’m just a writer. I just want to spend at least half my time writing and I don’t know how that’s going to work. And then I literally was like, ChatGPT, are there any other business people that spent 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. I mean, I’m in ChatGPT, I’m like Sam Harris. And there’s a bunch of people like this.

Dan Shipper

Because that is the business. That’s the business. That’s why I’m kind of trying to get to this. You can’t really—it’s not like a bunch of layers that you laminate together. You know, it’s all one piece of material. And the writing is part of it. And the way you run the business is 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. It’s no longer the same material anymore. Now there’s a point like you do grow though to a place where you do other types of things. So for example, I’m not in the products 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’ve atrophied because I delegated most of that. And now when I want to get back in there myself, I’m like, eh, not very sharp, but I can do it. But I do other things that I didn’t do before. So you’ve gotta be doing something, but it takes a while, I think, to really transition out of something versus just handing it over. There needs to be a transition. So if you don’t like to write, 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—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 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 when I delegated more of that, it wasn’t because I loved it and had to do something else, it’s because I kind of didn’t really want to do it so much. But I actually lately have 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 do pull-ups for a year and you try to do a pull-up. 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. So I need to get back into doing that. So I do want to get back into doing that some more. But I think what—again, when you hand something off, it can’t be something you love to do. You gotta hold tight again. That’s for you.

(00:50:00)

Dan Shipper

Where did you learn this? Like it’s all one thing idea. And how did you learn it? It feels almost spiritual to me.

Jason Fried

Yeah. It feels like that to me too. I don’t know where I learned it other than I would say that I’m going to use architecture again and furniture and cars and watches. Actually as a potential explanation, whenever I come across something that is like a complete idea—Frank Lloyd Wright buildings are a good example of this. When I see like a really nice Frank Lloyd Wright building or a house and I go in there, I go, this is someone’s idea manifested in wood and glass and concrete and stone, but it’s a full idea. Like it’s a full, complete idea. Everything there was designed and made by him. And here it is. If you were to take the sink out and put in like a Home Depot sink or something, or like even some fancy Italian whatever, sink, you are like, no, no, you can’t take the sink out. The sink’s part of the house. 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. Whenever he did a concrete floor, pretty much it was tinted this color. If you went back and painted it blue—you can’t take the red out of the floor. It’s not a Frank Lloyd Wright house anymore. So I think that’s part of it. And whenever you see like a watch that’s just so 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. Just things like that. And so I think that good companies are the same way. You can’t just tease them apart, replace big things with other things. It just, it’s no longer that whole anymore. So I think something—that’s how I think about it. There’s some, and then there’s some houses you can walk into—yeah, you could replace these windows with like a new set of Fleetwood windows or some custom windows or Sky Frame 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 as the house that cannot be pulled apart. If you replace anything in that house, it’s going to stand out. This is wrong. And I think the best things are like that. So anyway, and again, it always comes back to like this feeling. 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 whole, a single piece, a single idea, a single concept executed so beautifully. You get a feel for that when you run into stuff like that. It is a spiritual experience. So there’s that. I mean, there’s probably other influences that I’m unaware of, but I would say that those are the things.

Dan Shipper

Beautiful. I’ve got a little chill going up the back of my neck. So have you ever been into a space like that? Like for you, do you know what I’m talking about?

Jason Fried

I do. I definitely, I think there’s 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. I think I’m probably not—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—there’s something sacred about it, and it just gives me that feeling. If you go into a church or a certain train station or certain things, you get a feeling like that. I don’t have words to be like, this is what the idea is, but I think you can just feel it.

Dan Shipper

Yeah. And there are fewer as we become less willing, I think, to invest in whole, in complete ideas as a society. You see a lot of things that are just sort of pieced together and they can look good, but they don’t feel as good as something that is a whole complete idea where everything was considered. And it’s just, it’s a special experience when you run into stuff like that. So I mean, I can’t say I’ve achieved that in the things we’ve made. I try, I aim for that, but there’s always trade-offs in everything. And it’s just true about architecture too. Unless you have some client who’s just willing to do whatever the architect wants or whatever. But software has more trade-offs because you, in some ways you have to deal with all sorts of conditions that aren’t fixed. A building, you build a building and there it is. Like software, well, it can show up on this screen or that screen or this screen size and things can shift and whatever can happen. And you know, it’s not quite the same. But the spiritual aim, let’s say, is similar.

Jason Fried

Well that’s as good a place as any to leave it. Jason, thank you so much. This is amazing.

Dan Shipper

Yeah, it was fun, Dan. Thank you. Thanks for having me on.

Thanks to Scott Nover for editorial support.

Dan Shipper is the cofounder and CEO of Every, where he writes the Chain of Thought column and hosts the podcast AI & I. You can follow him on X at @danshipper and on LinkedIn, and Every on X at @every and on LinkedIn.

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