#90 – Enjoying Building Simple Products with Jason Fried



#90 – Enjoying Building Simple Products with Jason Fried

We are truly honored to host Jason Fried, co-founder of 37Signals and the mastermind behind Basecamp, and Hey for one of our deepest episodes. A leading critical voice in startup culture and product design, Jason delves into challenging conventional business approaches with a focus on simplicity, enjoyment, and nimbleness. In the second part of the conversation, Jason also hints into what he calls a Post-SaaS era that he intends to kickstart with a new suite of products called Once.


Youtube video for this podcast is linked here.


Podcast Notes

This is a landmark episode for us, as we’re joined by Jason Fried, co-founder of 37Signals and the creative force behind Basecamp and Hey. 


A true critical thought leader in startup culture, product design, and organizational development, Jason shares his deep insights into the transformative power that comes from challenging traditional business norms – be it bootstrapping, subtracting, restraining, or creating shorter cycles – in a world where increasingly, “more” is considered better. 


As an acclaimed author of International Bestsellers –  like “Rework”, “Remote” and “It Doesn’t Have to Be Crazy at Work” – Jason offers unique perspectives on customer and product strategies, intuition in decision-making, and the importance of human touch in technology.


He also shares insights on 37Signal’s multi-product strategies and touches on their upcoming product “Once”, which promises to be the first post-SaaS product. 


This episode has got it all, and speaks on untouched conversations like never before. Don’t miss out.


Key highlights

  •  A deep dive into approaches that challenge traditional startup culture and product design principles – bootstrapping, subtraction, simplified metrics etc.
  • Restraints as powerful enablers organizational strategy
  • A centralized product editor vs. a decentralized structure approach in an organization
  • Understanding the dynamics and strategies behind managing and growing a multi-product company
  • Short term vs. long term goals and getting buy-in from the organization
  • Why AI isn’t a magical duct tape, and how do you tackle leveraging AI’s capabilities and preserving a product’s unique identity
  • Understanding how friction can be either incorporated or overcome in the creative and development process
  • The Next in SaaS and what is “Once” building


This podcast is also available on Apple PodcastsSpotifyGoogle PodcastsSoundcloud and other podcast streaming platforms.


Topics (chapters):

(00:00) Embracing Uncertainty: Decisions, Innovation, and the Fluidity of Workplace Dynamics

(03:17) Navigating constraints and restraints

(10:39) Getting buy-in from your team 

(16:04) Being empathetic with customers 

(21:16) Building purpose in an organization

(28:04) Modularity, Composability, and Integration

(33:32) AI is a universal duct tape 

(38:15) Path to Multi Product

(42:31) What “Once” was (and will be)

(49:23) Breadcrumbs and Suggestions


To find out more about Jason’s work:


Other references and mentions:


Recorded on 16th November 2023.


Get in touch with Boundaryless:

Find out more about the show and the research at Boundaryless at https://boundaryless.io/resources/podcast



Music from Liosound / Walter Mobilio. Find his portfolio here: https://blss.io/Podcast-Music


Simone Cicero

Hello everybody and welcome back to the Boundaryless Conversations podcast. On this podcast we meet with pioneers, thinkers and doers and we talk about the future of business models, organizations, markets and society in this rapidly changing world. Today I’m joined by my regular co-host, my colleague at Boundaryless, Shruthi Prakash, who is joining at 2 a.m. in the night from Jakarta.


Shruthi Prakash

Hi everyone.


Simone Cicero 

I should thank you so much for your effort. And to be honest, I can’t really contain the excitement because today we have on the podcast someone who has been constantly recognized for at least 20 years as a unique voice, I would say as a flagship of critically thinking about startup culture, product design, organizational development and culture we have with us.





Simone Cicero 

Jason Fried. Is it right? Jason Fried or Fried? Fried. Okay, sorry. I mean, as an Italian, nobody pronounces my surname and name well when I do interviews.



Jason Fried, yes, correct. Yep.



That’s totally fine. Not a problem. I get it. Yep.


Simone Cicero 

Thank you so much. So again, welcome to the podcast, Jason. It’s more than a pleasure to have you, because for the ones that don’t know you, let’s say that you are a co-founder of 37Signals, a company that makes Basecamp, which is a pioneering web-based project management tool, Hey, which is a premium email service, premise, as I would say, on privacy and user control, more or less.


And you’re also working on a new suite of products, which is called the “Once” that I would like to talk about during the conversation today. You’re also not only an entrepreneur but an author. I remember, I think it was something like 15 or 16 years ago, I was reading your books and as a young professional trying to get everybody excited about rework. 


And it was probably the start, let’s say, of something that then led me to become what I am and the company that I founded. So I’m really, I think I owe you something from this perspective. So great to have you today. So I would say that it’s hard to make an original conversation with you because you are so vocal online that you gave so much back to the community that it’s hard really to push you to say something new, which is something that I would like to do tonight. 


So as a starting point, let’s say, I would like to start from some of the elements of your, let’s say, the canon, your canon, which is about subtracting, smallness, short cycles, bootstrapping, all things that make me think about two elements that I would like to ask you to talk about –  One is what I call constraints.


And it’s really interesting because, in complexity theory, which is one of our pillars, constraints are often used as a way to generate innovations. So if you constrain something, it will flourish, it will innovate. And on the other side, I would say you also talk a lot and I would say base a lot of your work on an idea which is more an idea of restraints.


Simone Cicero 

So limits and prudence or something like that. So if you can talk about these two things as a starting point, it will be great as a start.



Yeah, sure, of course. Thanks for having me, by the way. It’s nice to be here. Constraints are definitely part of who we are and restraints. I like the way you put that. I have a hard time in some ways separating the two in my mind, but they are different. For example, we’ve stayed as small as we can on purpose. Now, that doesn’t mean we want fewer customers. We’d like to have as many customers as we can, but as far as our company size, we’ve kept the company as small as possible.


And that forces us to, it basically says we can’t do everything we want to do, which is a good thing because there’s a lot of things we want to do that probably aren’t very good ideas, but we want to do them, but they’re not that good. So it forces you into deciding what’s worth doing. And every company is constrained in this way, by the way. I mean, even companies like Apple can’t do everything they want to do or companies like Facebook or Google can’t do everything they want to do. 


But when you’re small, really small like we are, we have fewer than 100 employees, you really can’t do everything you wanna do. And even the things you decide to do, you’ve gotta figure out clever creative ways to do those things with fewer people. So I just feel like that’s a creative, there’s a lot of energy that comes from that, from this tension of not quite having enough but wanting to do things. 


And then what it forces you to do is to come up with clever creative solutions and also question things from a different perspective and see things through a different lens. Like, do we really need to do this that way or could we do this in a much simpler way? There’s a three-week version of this, but maybe there’s a three-day version of this. We want to do four or five other things too instead of this one thing that takes three weeks. So I just love working in that environment as frustrating as it can be sometimes. I find it to be much more advantageous and much more interesting. 


And then so the restraints for us, like we could afford to .. So we have to put a restraint on ourselves to stay disciplined, not to do that. So the constraints are the realities and the restraints are a little bit more like the self-imposed limits that we are often aiming for.


Simone Cicero

That’s a great way to frame it, I think. So constraints are more like, as you said, the reality-wise restraints are more intentions, right? Which is, I think, very interesting because if you think about technology, and technology has changed everything, and we never really imposed any limit on it. So I think your conscious way to look into limits is a great starting point to create something different, maybe not something large or or impactful, but maybe different, which is important. 


So you said something interesting that we want to stay as small as possible, but at the same time, you want to have lots of customers. You want to grow your business, essentially. And I think I connect these with some of the critique that you also raised recently with regards to some of your competitors that have grown a huge employee base and have a business which is comparable with yours. 


This week, we also were exposed to the conversation between Brian Chesky and Lenny Rachitsky recently. I don’t know if you had the chance to listen to it, but I think it’s connected to some extent. 


So what we are seeing at the moment is that product leaders are kind of trying, starting to recentralize product leadership and we are seeing a lot of the distribution of product management and product leadership that emerged in the last 10 years now being kind of criticized and canceled. So how do you think about editorial leadership in products and you know really not scaling pointlessly product leadership across an organization.



Yeah, I think that is an interesting trend that’s coming back. We’ve always been this way, which is a very centralized product development company because we’re always small. I mean, we’re our biggest now, which is around 80 people, but we’ve historically been significantly smaller than that. And I run product here. I have other people I work with very closely on that, but ultimately it’s my decision. I also own the company and I’m the CEO. So – that’s very centralized in that respect. I think, and by the way, that’s not to say that I’m the only one who can do this. It’s just that I do think that it is important to have a sort of a bit more of a singular vision when it comes to product development. Otherwise, I think things can go in a bunch of different directions. And I really, I haven’t listened to the entire conversation that Brian just had.

But I liked it. I saw a couple of clips, which I really liked. One of them, he was talking about how his companies grow. They form departments and departments end up battling for resources and doing things themselves because they can’t get resources. And then all these different departments are doing things their own different way. And you could say in some ways like you can make the argument that that’s, that’s like evolution and you know, the strongest will survive and whatever, but really it ends up being a mess practically. I mean, evolution might work over billions of years, but like, you know, over the next four years on, you know, if you had five or six or seven or 12 different groups trying to do different things in the product, different ways, it’s going to be pretty messy in the short term. 


So I do think it’s a good idea to have a central vision for the product. And then of course have very small teams implementing that vision. So for example, with Basecamp, we might have four or five different product teams working on Basecamp in any given six-week cycle, we work in these things called six-week cycles. 


And Each team is only two people. It’s one programmer, one designer, and they’re assigned to a feature or three or four features over that period of time, and they’re working on that. But before they begin to work on that, a few of us decide what work will be done over the next six weeks. So we develop this set of features or set of ideas, and concepts, and then we dole them out to different teams. And the teams then implement those in their own way to some degree, but still always pointing back at the original idea. And then I’m directly involved with reviewing this work. So that’s how you can give teams a lot of autonomy, but they also have to sort of report back to an editor in chief essentially, who sort of maintains a consistent point of view across the product. So you don’t have the product fighting itself by doing things in a bunch of different ways. So that’s my take. I think it’s healthy. I think it’s easier for a company like ours. I can’t imagine.


It must be quite challenging at a company of 2000. But also, the other part is not really necessarily the company of 2000. Actually it’s more how many products do you have? If you have dozens and dozens of separate products, it can be quite challenging to have a small team of people directing all of those versus if you have one or two products, it’s quite a bit simpler.


Simone Cicero

Shruthi please go ahead, I know you have a question.


Shruthi Prakash 

Yeah, I was just going to ask how you get buy-in into this idea, right? Like that to some degree, it is going to be centralized essentially. So how do you look at it in terms of alignment of goals within the organization? And are these, let’s say, driven by a customer-centric perspective or a product-centric perspective, or does it go by intuition maybe?



I think everything frankly that’s done by any human being is intuition actually. It’s informed by many things that you know and many things you don’t. It’s like the conscious and the subconscious. You know, that’s how decisions are made. So, you know There’s a thousand things pushing on you to make a decision and 996 of them you don’t know what they are. You don’t know why they are but they are and so at some point, you make a call. 


One of the benefits of working the way we work, which is in these short cycles, is that you can’t really necessarily make bad decisions that matter that much. So for example, if you’re working on something and you make something that’s going to take you three years to build and you make a bad decision, you can be in really deep trouble because that’s a long time to be working on a bad decision or a bad idea or whatever. 


The longest we take to work on any individual feature is six weeks. That’s the longest. Most things are a week or two or three. Some are a couple of days. So in many ways, these decisions we’re making are not that critical. Like if you make a bad one, you get to make another one in a month and a half. It’s not that big of a deal. So in that respect, buy-in is, I mean, look, practically I run the place. So I don’t need to get buy-in. Like, let’s just be honest. I don’t need to get buy-in.


But that’s not about shoving things down people’s throats. It’s like I’m trying to make the best decisions I can, but everyone knows like, you know, some are gonna be good and some are gonna be bad, and like some are gonna be better than others, and it doesn’t really matter because what we’re looking at is the sum total of things we make. Hopefully, there’s more good than bad. And as long as we make more money than we spend overall, we’re happy. So I’m not looking for certainty. I’m not trying to make sure every decision is the right decision. Trying to make sure most of them seem to be And the ones that aren’t, they just aren’t, and you do them and you move on. And sometimes you don’t know they were good or bad until six months later, if you even look backward. So, I will tell you that we’re not, we’re not KPI, we don’t look at numbers. We’re not, we don’t have KPIs, we don’t have OKRs, we’re not growth-based. We’re not like trying to hit growth targets. We don’t work that way.


We’re just trying to make the best product we know how to make based on our own perspective, things we hear from customers, insights, intuition, a million other inputs that we don’t even recognize, and we let the chips fall where they may. And, you know, keep your ears open, your eyes open, and you sort of adjust as you go, and you don’t get too stuck in anything. That’s the beauty of making a lot of small decisions versus a handful of huge ones.


Simone Cicero 

But the question that I have, it seems like you do not have KPIs. You don’t set OKRs. You don’t set the strategy. And these two weeks, sorry, six weeks cycles help you to stay very connected to the user right, to listen to the guests. So it looks like your company, or in general, your products are driven on one side by customers and being in touch with customer feedback, and very qualitative feedback, not quantitative feedback. And on the other side, you seem to be very much driven by, how does it feel to build the product? Am I right?



You’re absolutely right. I mean, this is gonna sound pretentious and I don’t mean it this way, but it’s more of an artist’s approach than a business person’s approach in a sense. It’s how does it feel? What does this thing feel like? How do we feel about building this thing that we’re making? It is really about feeling and feeling our way through the dark and feeling good about the things we’re doing. And sometimes you don’t feel great about the things you’re doing. You don’t feel great about everything. Sometimes you just gotta trudge through it. 


But it is based, you know, because we’re self-funded and bootstrapped, we don’t have to do things to hit growth targets. We don’t have to do things to satisfy investors. We don’t have a board of directors. We don’t have to impress anyone else except our customers and ourselves. I like that focus. It’s very tight, very clear. There’s no abstractions there.


Like if we don’t make things that our customers like, they won’t pay us eventually, or we won’t get new people to sign up and we will go out of business. Like there’s no one’s going to come save us. No one’s going to come pour another five million bucks in to give us another chance. So it’s very direct. 


But that said, we don’t always do things our customers ask us to do because our customers, their job is not to think about product development. Their job is to share their struggles with us. It’s not even their job. It’s just what they’ll do. And we have to then synthesize those and figure out how to build something that can help them. And it might not be based on what they’ve asked for. They might say something, we might go, you know, I think there’s something else here. I think there’s something deeper here. Let’s build this other thing that no one asked for, but I think it might solve that problem. Or we have just had a hunch on something that no one’s asked for. Let’s build that and see what happens, you know? 


So, you know, I don’t, a lot of it is feel and it’s a lot of feeling frequently and You know, we don’t make big, huge bets. We make a lot of small bets. And I think that that’s, in many ways, the safest way to work and also the most enjoyable way to work.


Simone Cicero 

You really have to build this empathic relationship with your audience, with your customers. So it looks like the fact that you’re so vocal, so present, so connected with your audience, it’s part of how you build products.



It is. It’s also like, it can be exhausting. And sometimes you just want to go into a hole and not listen to anybody. Because everyone’s got an opinion. And the more customers you have, the more opinions you have. And sometimes, you just want to do your own thing. And sometimes we just do our own thing, but we’re always listening to people. We’re always hearing things. We get somewhere around 500 emails a day. Our customer service team gets about 500 emails a day. Some of these are troubleshooting emails. Some of them are feature requests. Some of them are ideas. Some of them are pre-sales questions.


You kind of have a sense of like the things that are on people’s minds, the struggles people have. I know a lot of small business owners, we make most of our products for small businesses and small teams. I understand the struggles. We are one of those companies. So we build stuff for ourselves and people like us, which also makes it a lot easier. Again, it’s very direct. One thing I just do not like in business is abstractions. I don’t like imagining what people want. I don’t like having to build something for some goal that’s detached from customers.


I don’t like to build something for someone just because it’s financially viable for them down the road. Like these are abstractions. So we try to stay as close to concrete real things as possible, which is us, people like us, our customers, keeping an eye on our costs and our profits and our revenue and all that kind of stuff, but all real stuff. And I think that just gives us the best chance of survival. And also the, I just think we have, you know,


I like cars. This is a weird tangent, but you drive a car from, let’s call it the 60s or 70s, and you can really feel the road. You could feel the road. These are analog devices. When you turn the wheel, you’re literally turning the wheel, literally. Today you turn the wheel and a computer actuates this motor that turns the wheel, or you hit the brakes today and it’s basically a computer squeezing the brakes car from the sixties, like your muscles are breaking the car. You know, I like the feel of old cars for that reason. 


There’s a lot of great things about new cars, safer, faster, better handling, all that stuff. But there’s something special about being so connected and so directly connected to the thing that you’re doing. And I think we try to run our business with that in mind. And I think that the larger you get, the more modern, the more modern a car you are in a sense, where you’re actually detached from the outcome of the things that you’re doing. 


And so you end up measuring by abstract numbers and statistics and dashboards that are representing something else, but aren’t really the thing. I just like to know things. This is your point about qualitative versus quantitative. I like to know the qualities. I like to know things. How does it feel? So I’m ranting a bit, but that’s how we try to run the business.


Simone Cicero

But it’s really interesting. Yes, yes, yes. 



As an Italian, you must appreciate this, I’m hoping, with cars.


Simone Cicero

But I would say really as someone who likes to be embedded in things and feel them, right? And to decide through something that sometimes you cannot explain, right? An abductive decision process that you seem to embrace. And I have a kind of a small, not wanna say prerogative, but a deeper question before Shruthi, I know he has another one. But do you feel like technology has gone too far?



I think technology is going to go where technology is going to go. And so I don’t think it’s gone too far. I think it’s gone where it’s going to go. And nature, something I’ve tried to get better at in my life is just to recognize the nature of things. And you know, the nature of technologies, it’s going to push, it’s going to push, and it’s going to end up wherever it ends up. There’s no going too far or not going far enough. It just is. So many things are like this.


If you go to a mall with your kids and everyone’s screaming and yelling and they want this and they want that, that’s the nature of going to a mall with your kids. You can’t be annoyed at your kids that they want ice cream and they want toys. That’s what they want because that’s the nature of that. 


So trying to understand the nature of things and then flowing with that. I think that there’s advantages to a lot of modernity, obviously. But there’s also some really great things about what we’re trying to call the Stone Age. 30 or 40 years ago. There’s some wonderful things there too. 


So technology is going to do what technology is going to do. But I think also looking back a little bit is very handy to find things that were actually better before and not losing sight of the fact that just because we’re progressing, it doesn’t mean everything’s getting better. There’s many things that are getting better and are possible today that weren’t possible before, but a lot of things have gotten more complicated today than they need be. 


And so to your… Maybe to your essential question. I think technology has made a lot of things more complicated than they need to be. But whether or not they’re better is sort of a subjective point of view, and I would say they probably are for more people. But I can definitely see some things have gotten more complicated than they need to be, and we want to return some of those things back to simpler times, let’s say.


Shruthi Prakash 

So, yeah, so I think taking off on one of the points that you said earlier, right? I don’t want to sound like it’s some existential question or like I come from some, but basically, if my thing is, if let’s say things don’t matter in the larger run right, larger scheme of things, then how do you build purpose, right? Essentially if they are, let’s say more driven by short-term decisions or short-term impacts, right? How do you build purpose on a larger scale? Or is there some one thing that you know, has sort of stayed true through the entire, let’s say, two decades of your work?



Yeah, I don’t think about the purpose very much. I think about doing the best work that we can. And the purpose of that work is to build the products that we build and take care of the customers that we have and to also enjoy our day-to-day, you know, to exercise our own creativity, to satisfy our own intellectual curiosity.


Those are the things that really ultimately are the purpose. To me, it’s all day-to-day stuff. It’s not a long-term future thing that I’m pointing at. It’s now like that’s what we have. We have now and later we’ll be now then. And that’s kind of, that’s how I’ve always thought about it. That’s why I’m not a long-term planner. I like to say we’ve been in business for a long time. We’ve been in business for a long time thinking basically a day-to-day and not 20 years at a time. I did not think about it 20 years ago. 


Well, we’re almost done, next year’s our 25th year in business. So I didn’t think 25 years ago that we’d be in business for 25 years. I’m like, can we stay in business now? Great, let’s keep doing that. Eventually, that will add up to something. But I didn’t even think about it. I wasn’t thinking about what it would add up to. Just like, can we stay around? If we stay around, can we mostly do what we enjoy doing most of the time? Can we make really good things and put great stuff in the world?


Can we put stuff in the world that would not have existed had we not made it? We have unique points of view. Let’s put that stuff out in the world. It’s not gonna change the world. It’s not, you know, it’s some big, huge thing, but it’s great for tens of thousands of people or a hundred thousand people or anyone who comes in contact with it, who likes it. That’s a day’s, that’s a day and a career’s worth of great work, in my opinion. Yeah.


Shruthi Prakash 

It must be good to be you.



I don’t know. I mean, well, tell me, do you, are you, why would you say that? Like, do you think that people focused, or maybe you focused too much on the biggest possible picture in the impact you’re trying to have, or am I just projecting?


Shruthi Prakash 

No, I mean, I think increasingly so, it becomes future oriented, right? Which is where it’s refreshing also to hear a perspective which is sort of against that essentially. So it’s interesting to know that it’s possible. I think the leeway that it provides to be conscious about just the present is extremely beneficial.



I think that if everyone’s really truly sort of being honest, everyone does live day to day. Like you just kind of do. And we can hope for something down the road. Like I hope that our stuff is successful. I hope that we stay in business. I hope our employees like working here. I hope our customers like our stuff. Hope is about kind of the future in a sense. But really it’s all built on bricks that are laid down one day at a time.


And the structure you end up with is what you look back at when it’s built. I don’t have any idea what it’s going to look like ahead of time.


Simone Cicero

It looks like a very Daoist approach to building a business, right? So kind of trying to stay in the flow of things. So let’s depart from this more theological element and move into something more practical and also something which is our bread and butter that is building the organization and evolving the organization. 


So you started from one product and recently you have introduced it, relatively recently, you have introduced another product which is “Hey” and now you are introducing another one. So I’m curious, from your perspective, since you are very about not having to grow and at the same time you are very editorial, which are things that do not marry, at least from my perspective, much weight to the idea of building a portfolio of things. Or to some extent, I would say they connect because building a portfolio is a way to grow without expanding, I would say artificially. So building diversity of product resonates a little bit. 


But at the same time, I’m curious to know, how do you leverage in building the portfolio, how do you leverage, for example, your employees, the credit power that they have? Are you looking into empowering more of your employees to build more products? Also because, and that’s it, but essentially because I see that the market is going in the direction of building more products. 


So companies will be required to build a scope, economies of scope in products, so more products, more diversity, just because the market is going there. So I think that in the future of 37 signals, there are more products to come. So what is your approach, your posture towards how you enable this diversification of products?



Well, so when we first started, let’s say in 2000, we started in 1999, we were a web design firm, but in 2004 we launched Basecamp. And then in 2005 we actually launched a product called Backpack. In 2006 we launched a product called Campfire. 2007 we launched a product called HiRise. After that we built a job board. We built another product called Know Your Company. We wrote a bunch of books. So we’ve always made a lot of stuff. And then we stopped making a lot of stuff. We said, you know what? We’re going to focus just on Basecamp for many, many years.


And we did that for a while and it worked out well, but also frankly, we got bored. We got bored just doing one thing, you know? And yeah, we’re makers. We like to make stuff. We like, you know, you kind of, we almost repressed ourselves for a while. Like, let’s just focus on, and the basecamp got really, really good because all of our energy was on that. And it’s still great and we still improve it. But we also said, you know, we have other ideas that just bubbled up that we have to deal with.


We just, we want to make this email thing called, Hey, hey.com. We just wanted to improve email. Email was frustrating us. We did that. Um, and now the stuff, this new category of products under the once “once.com” label, we’ll be building a bunch of things under that. These are just itches we felt we had to scratch. And, um, again, we’re like, we’re, we’re pressing ourselves for a long time. And at some point we’re like, we don’t need to do that anymore. Why don’t we go back into making more things at once? Which is why we ended up hiring more people.


Which is why we’re a larger company today than we were before. But it’s just one of those things where it just finally felt right to go down that road again.


Simone Cicero 

I was thinking that it would be interesting to hear your perspective on what is actually happening in the market. So as I said, you are more into building product portfolios. And you just introduced this topic. But basically, you can maybe rhyme with what’s happening in the market.


these trends that are pointing towards more composability, more modularity. I don’t want to weave the topic of Web3 and blockchain, but it’s there, it’s happening. So what do you think about how the market is evolving and what does it mean for a company like yours, or in general for product companies to ride this evolution towards composability, modularity and integration, which is undoubtedly rising?



Yeah, part of me wants to say I don’t really pay that much attention to the rest of the market because all that matters is that I can make great stuff for our customers and find enough customers. So as long as that exists, the market is the market. Now those customers live in the market and they have other choices. All that’s true. I can’t control the choices they have. They have the choices they have and we have to just do our best to make the best thing we can.


And I think oftentimes when you pay too much attention to what everyone else is doing, you end up building what they’re already building. So I think there’s something good about a certain naivete and ignorance in a sense. Like I kind of want to live on an island frankly and like to build our own thing. That said, I’m aware of what’s going on. I mean, the biggest thing in our industry of course is AI and integrating with AI and figuring out how AI can really be valuable. I think it’s absolutely fascinating, obviously, and incredibly powerful. I don’t really feel like it’s clear yet. I know we all know sort of what it can do, but I’m not sure it’s that clear yet, like where it’s useful in business products. Now, some people might go, what are you, an idiot? Like, of course it’s useful. It can do this, that, and the other thing. It can do this, that, and the other thing.


I’m still not sure it’s useful yet though. I think it certainly will be as it gets better and better and better and better. But I see a lot of it like being used for these very rote things like, well, it can summarize super long meetings and big documents. It’s like to me, yeah, I can, but like, is that, are you gonna fully trust that summarization? If you’re responsible for what’s in that document, are you really gonna trust that that’s it? What if you miss something?


And well, I read the summary from the AI. It’s like, well, I don’t care. I don’t pay the AI to do your job. I pay you. So these things can be helpful. And they look good on the packaging in a sense. But I really still don’t know if they’re really fundamentally useful. That said, they will be. And we’re keeping an eye on it. But we’re also not jumping in just to kind of add summarization and automation to our stuff right now. I still think there’s a lot of value in humans. I’ll give you a quick example. We have this feature in Basecamp called Hillcharts. Hillcharts help you communicate to other people on the team where a project really stands from your perspective.


It’s a hill and there’s dots on it and you move the dots along the hill and the dots represent scopes of work. The computer’s not moving the dots. You’re moving the dots because you have a perspective. The human perspective is important. You’re working on the project. You know the project. There’s a lot more that happens on the project that’s not represented in the software. Maybe you’ve had conversations with people. You’ve had other conversations with other people.


You have other information to bring that the system doesn’t know. That all goes into the subjective decision about where this dot goes next. I think that is very, very useful. Now, you could say, well, it should be automated. The dots should be moving along the line as more things are completed and checked off and whatever. But I don’t believe that that actually represents where projects really stand. I think people know where projects really stand. So I think there’s a lot of power in HI still, human intelligence. because we all are humans working together and we have, there’s a lot of things that just simply are not represented in software and in data that I don’t think are better off lost. I think they’re better off getting promoted. So anyway, long story short, fascinating technology, amazing, gonna change a lot of things obviously, but I think we’re just paying attention and meeting it with curiosity at this moment, but not like racing to implement. 


And by the way, frankly, like, what everyone’s basically just doing is working off the open API or open AI API. It’s not like companies are not really building AI into their things. They’re like sending data to open AI essentially and getting stuff back for the most part. So, you know, it’s very easy to add that and you can add it later. You can add it whenever you want. It’s not like there’s these, all these, all these startups have this unique technology available. A lot of them just are using someone else’s technology. 


And I think there’ll be more and more APIs for more and more big players that own large language models that you’ll be able to plug into. So I don’t feel like anything’s really, like anyone’s missing out on anything right now either. So that’s my general, maybe completely misguided, a view of the market. I have no idea. Maybe I’m a dinosaur, but that’s my point of view.


Simone Cicero 

No, but that’s a good leads into the next question that I would like to ask you about the post-SaaS era, because it’s kind of very representative of your position to avoid centralizing into a third party that you start to depend forever. But before doing that, I would like to ask you maybe, what do you think about the potential that AI has to become, Alex Komoroske calls it

a kind of universal duct tape, right? The magic duct tape that can put everything together. And I feel like there is somehow a treat of, it’s fascinating because on one side there is a threat of becoming an oddity, playing over the top to every product. And then the question for the product makers is, how do you consolidate your brand, how do you resist? 


For example, again, to quote again, Brian Chesky, he said recently that he didn’t join the plugin program for OpenAI because he wants to own the brand, basically, the brand experience. So I’m also curious to know your product designer perspective when it comes to the product design.


Do you feel like a threat of AI becoming an OTT layer on top of all the products that can plug things into it? Or do you believe that to some extent it would be important to customers to share with the brand some sort of ontology that cannot be overcome by AI? So to some extent, to make it more clear, customers are buying Basecamp not just for the experience, but also for the mental structure. So for example, this idea of the ill charts, it’s an affordance for intersubjectivity on a project which no AI is gonna fix. It’s embedded in how you thought about the product and the kind of message you want to bring to the people.



Yeah, I like the way you put that, by the way. I don’t know. I do like this idea of AI being really damn good duct tape, though. And I mean that in the best possible sense. The duct tape is incredibly good stuff. It’s used for all sorts of things. It’s the perfect solution for a million different things that don’t have specific solutions for them. It’s this general solution for a million great things.


So I think AI will piece things together. And I think as companies use more and more separate tools and separate places by separate manufacturers and our separate producers and have separate interfaces in different data stores, like there’s gonna be a need for something to sort of centralize all this stuff and make sense of it all. So I think that’s a great place for it. Organizationally though, we’ve decided, like we use Basecamp to run our entire business. All of our projects, all of our decision-making, all of our ideas, all of our concepts, marketing, product development, everything’s in one tool in one place. Because I think that centralization is important. And I think that you can use a bunch of separate things and then like hope and wish that there’s something that’s going to duct tape it all together, or you can avoid the complexity of trying to find the duct tape and looking at a big mess of duct tape and just use one thing that works really well, that has a lot of human subjectivity in it. Cause I do believe that that is people working together. we’re an organism. There’s something biological about it, and it’s not always explanatory. It’s not always reducible to a summary or to an insight from something that’s only looking at the digital information that it’s presented with. 


So anyway, I’m not even sure I’m quite answering the question, but I think that I think privacy is something people need to think about because right now, I mean, people think about privacy, don’t really care that much about it, and that’s all fair. People can make their own choices. But right now, companies are sending a lot of data to third parties to process. And I don’t know if customers are actually aware of the fact that a lot of their data is being sent to OpenAI to process something and then have it spit back. I think it’s very important to be very clear about that. And again, we haven’t done that yet, but if we were to do that, if we were to add a feature like that, we’d have to be very, very clear about it.


Simone Cicero 

I’m very much looking forward to your first experiments in AI. I’m curious to know what will come out of that. So I.



I am too, because I don’t know what they’ll be. But I’d love to see, I’d kind of love to see something like, here’s the human take and here’s the, here’s the H.I. take and here’s the A.I. take. Like everything would sort of have two takes, two perspectives. And from that, you sort of, I think, get a brighter, more beautiful picture, rather than going like whatever A.I. says is the way it is because it’s so smart. Yeah, it is. It’s smart with the data it has.


How does it know about that conversation you had over lunch that informs a lot of what you do moving forward? Maybe eventually we’ll know those things too. I just think there’s a lot more to it than just information.


Shruthi Prakash

I think what I think we wanted to sort of segue into is to understand your, you know, sort of perception of what the future of SaaS is. And I mean, there is so much softwares now and super apps and multi softwares being used by each organization. And then they have one SaaS product to control another SaaS product and so on. So it’s really reached its sort of epitome of usage, right? So when does it, has it already become too much? And if it has, then what do you see as maybe the next steps?



Yeah, I think there’s definitely a subscription overload and fatigue for sure. A lot of our customers, people who signed up for Basecamp, are coming to us because they were using six other products first. So they were using a to-do thing. They might have been using Asana, then maybe they were using Slack too and their engineering team was using Jira. And then they had Google Docs as well. And maybe someone was using Asana or Trello. It’s like, whoa.


That to me is a bad recipe. Um, you don’t need that many ingredients. Uh, and people are beginning to realize that. And what they’ve done is they’ve tried to piece it all together by throwing all these notifications into Slack. Slack becomes the, the, the catcher’s mitt. It’s catching all the balls from all the different things and trying to make sense of it all. And it’s just like, it’s a mess, a complete unnecessary complexity.


It’s more expensive than it needs to be. It’s more complicated than it needs to be. You gotta onboard people on different products. You let someone go, you gotta take them off five or six different things. I don’t know where things are and which team is using what. It’s just, so it’s not that, I think there should be a wide variety, a beautiful variety of diverse products that address a whole bunch of different things. But I think organizations should think a little bit about what it means to have to connect four or five or six or seven separate things together when maybe there’s one or two things that work better together. 


So anyway, I’m in full support of more and more products and more and more variety and more and more opinions and more and more perspectives. I just think it’s on the company to understand what impact it has when you sign up for seven or eight different things or even four or five different things and ask your company to work in a cohesive manner across so many different products with so many different ways of working and so many different interfaces and so many different users and the whole thing. But no, I don’t think SaaS is over by any means. I think it’s going to remain a very, very, very powerful thing. It’s a very easy thing. It makes a lot of sense. But I do think there’s subscription fatigue. And if people start to look at their bills, which is what they’re starting to do now because times are getting tighter, they’re going to go, wow, I’m spending how much for that? Like what? 


I’m spending $2,800 a month just to chat with my employees? How come it’s free on WhatsApp? How come in the personal realm it’s free to chat with groups? Why am I paying three grand a month to chat with my employees that are also just a group of people? That’s something off here. And then I’m also paying this much for this thing and this much for this thing. Hang on a second. So I think you’re going to see that. And that’s one of the things we’re trying to address with Once with the new line of products, which is… Sorry, I’m going to turn this ringer off.



This idea that whatever happened to software you could own, why is every piece of software rental now? And we’re trying to make some stuff that you can own and you pay for it once and you run it on your own servers and you get your costs under control and you get them out of the way and they’re in the rear view mirror. And you also get the code so you can play with it and adjust it and do whatever you want to it, which is also something that’s been lost.


SaaS is very much a trust game. You don’t know what these companies are doing with your data. You don’t know really who’s looking at it. You don’t really know what they’re recording and you have no insight into that. You can’t see how the product works. You can’t see any algorithms. You can’t see anything. And you also can’t see in beyond the product, like who has access to the database at this organization and all the things. And so with “Once” products, you’ll install them and you run them and you’re in control of them and the data is yours and we don’t see a damn thing. We can’t do a damn thing. It’s not on our infrastructure, it’s all on yours.


And this is not going to replace SaaS, and it’s also going to be foreign to a lot of people who are just more familiar with and comfortable with SaaS. But I do think there’s going to be a growing hunger for an alternative to rental. And I think ownership is going to be a thing again. And we’ll see how that plays out.


Simone Cicero

What are the major, I would say, corrections that you put in place to ensure that something like “Once” is not felt as a return to the past or something that is not efficient, not cheap? I mean, because if I think about market dynamics, competition, and componentization, something starts as novel and ends up being rental and then ubiquitous as a commodity. 


So when I first heard about it, Once I said, somebody put this on a word lay map and it means essentially try to understand how this works from a perspective of value perception and evolution. So what is the major, if you can say, because it’s coming up, it’s a surprise, but if you can say something about, how did you make it relevant and how did you make it? Of course you have to experiment, but how did you make it something that is not perceived as coming back to something from the past?



I will say that we don’t know yet. We don’t know. My answer is always, we don’t know until the thing is out in the market and the market tells us. We have a hunch. But one of the things that’s been hard about SaaS is you don’t have to worry about any infrastructure yourself. You don’t have to install stuff. You don’t have to know how to work servers, the whole thing. And for a long time, it was actually quite complicated to self-host stuff.


But it’s actually gotten a lot easier with things like Docker and there’s some other technology that just makes it much, much, much simpler to run server-side software on your own local server. It’s not as hard as it used to be. There’s been some major leaps. And so what would have been a real hassle before is no longer a hassle. It’s literally if you can access a terminal on a server, which many people can do these days.


You can type in one line, which will give you a command, essentially, and it’ll pull it down, install it, and you’re off and running. It can be that simple. So that’s one thing. The other thing is we’re trying to bring modern interface design and concepts into these products. “Once”, by the way, again, just so people… Once is the sort of the brand, and the products will be in that brand.


We haven’t announced the products yet. There’s just going to be one to start and we’ll add another one, add another one over time. But we’re trying to pick off things that people already know how to use as well. So we’re basically looking out at the market and saying, what are the products that are commodities? What are things that everybody understands that have been around for a long time, yet people are still paying luxury prices for And that people don’t have to relearn, they don’t have to be introduced to this new concept, but rather it’s like they already know how to use it, but now they can host it themselves, pay for it once and be done. And part of this is not trying to replace everything that these products do because they’ve all gotten quite a bit bloated. So we’re kind of returning back to this idea of 80-20, like the 20% that matters delivers 80% of the value essentially, the Pareto principle, and we’re applying that to these products, so they’re going to be very, very, very simple and very easy to get started and very easy to get going on. 


And I think there’s a real modernity as well in actually letting you have the code, which is a throwback to the past, but it’s actually, I mean, it’s more like open source in a sense, which is a very modern idea. And now you get to own it yourself and you get to examine it if you want and see exactly how it works. And I think for product teams, even if they don’t wanna use these products, they’re gonna be priced so affordably that a lot of teams are simply going to buy them because they wanna see the inner workings of how this product was made. You don’t get to see that. You don’t get to see how anything is made anymore unless it’s open source. And when it’s open source, it’s not always the principles that are behind it in terms of who’s designing it and who’s writing it. A beauty of code and efficiency is not always primary objective. And so we are focusing on building the purest, best products we can with beautifully written code, beautiful design, and beautiful HTML and CSS and JavaScript and Rails and the whole thing. 


And so people can really see what it looks like to make something like this. So I think being able to examine the inner workings will be very interesting to a lot of people. So I think it’ll be an educational thing for a number of teams who are just curious about how this stuff works.


Simone Cicero 

This, I must say, this sounds very you, very 37 signals, because it’s really kind of creating an affordance for people to be involved, to care about their technology, to move from consuming technology to producing it and mastering it. I think it’s very interesting because if we have a mouthful of saying technology reduces barriers and so on, but then we just click and iterate and I instantiate products that we consume. 


While I think you are kind of creating a, I wanna say a hacker experience to some extent, like improving instead of customer experience, you are moving into a hacker experience and I am very much looking forward because I’m an open source advocate since decades. And so it looks like you may have kind of cracked the code. I’m really looking forward to see the ones.



Maybe. I have no idea. Truly. Like we do not have any idea how this is going to land. It might be a big thud. It also might be a big hit. I just don’t know. We really don’t know. And that’s okay. Like, you know, it’s not a massive risk for us to do this. We had an idea earlier this year. We decided to do something. These products are basically going to be built ultimately with one or two or three people. Working on each one is going to take a couple months to do each because they’re very, very straightforward and simple. So we’re going to make three or four and see how it goes. I hope it does well. Maybe it won’t. I mean, maybe we’re too early, maybe we’re too late. I don’t even know. Maybe that’s the same thing. Who knows? But what’s important is that we’re willing to take a swing at it. I think the industry needs it. I think that we’ve become complacent. Everything is just like a subscription. And there should be options. That’s all we’re saying is there should be options and we’re going to provide some of those options. And those who are interested in checking that out can check it out. And if you think it’s a bad idea or a dumb idea or you don’t like the thing, that’s totally fine as well. But options should exist and we want to be on the record as producing some of those. So we will find out. And if it’s a flop, I wouldn’t be surprised. And if it’s a hit, I wouldn’t be surprised. It’s kind of a fun place to be. And I like to be in that big unknown range.


And something I said earlier, and I’ll reiterate is I’m never interested in certainty. I don’t, I’m not like we could have, could we survey the market and find out if this is going to work? I don’t know. Maybe, maybe not. I doubt it. Um, I’d rather just build the thing and see what happens and not take a huge risk and not put ourselves at risk, but try something and have fun with it and have fun with the branding and have fun with the messaging and have fun with the idea and see what happens. Yeah.


Simone Cicero

Great. I mean, people still listen to vinyl, so maybe, you know, it’s also a vintage feel to it. 


Shruthi Prakash 

That’s awesome. Yeah. I mean, it’s great to hear. I don’t know many times, honestly. It’s good, it’s so motivating to hear that. And yeah, I mean, we, as we sort of near the end of the podcast, right? We wanted to hear your breadcrumbs as we call it here. So any suggestions on maybe books, podcasts, videos that you can recommend for our listeners.



Sure. So books.One of the books I highly recommend is  Several Short Sentences About Writing. –  And it’s a wonderful book about writing sentences. So it’s not about writing essays. It’s not about writing stories. It’s just sentences. And of course, sentences are the building blocks of all these other things. And it’s just, it’s beautifully written. It’s super fun to read. It’s really interesting and poetic and creative and clever. And I highly, highly recommend this book. So


Do check this out if you’re interested in learning how to write a bit better, or just curious about another perspective on writing. I like this podcast called EconTalk. Do you know the podcast? Russ Roberts, I think, is the guy who runs it. I think it’s called Econ Talk. And I like it because I like him as a host. He challenges his guests. There’s a whole wide-wide variety of different topics that are discussed. It could be anything from, you know, consciousness to wars, to technology, to AI, to politics, to economics, whatever it is, right? Cities, all sorts of interesting architects. It’s fascinating. So I really enjoy that podcast quite a bit. I like listening to that. I’m trying to think of other things that have really moved me lately. I mean, to be honest, like, I just like to go for walks. I like to look at nature. I like to examine nature. 


As a designer, I’ve always felt like if you want to see the best design there is, just go look at a leaf, go look at a plant, go look at a flower, go look at an insect. These are designs that have been perfected. We all talk about iteration. These are designs that have been perfected over millions or billions of years. They’re pretty damn good. They’re the best they’ve ever been right now. There’s something special about that.


I like that. I also like architecture a lot. So I like to walk through buildings. I love well-designed buildings and I abhor poorly designed buildings. And it’s just nice to kind of be in a space that was considered. I think software is very architectural in that way. I think of software as a series of spaces and places, actually more so than screens. And so I’m very spatial in that way and I enjoy going to buildings. So I would. I encourage people to take walks outside and walks inside. You know, that’s sort of my, those are my bread crumbs that I’d like to leave.


Simone Cicero

Fantastic. Well, Jason, I think that we succeed in unearthing some aspects of your personality and your, you know, your work that haven’t faced it so clearly in other podcasts. So I’m really, I’m really excited about releasing this to our listeners. I’m so thankful for your time. So I hope you also enjoyed the conversation.



Very much so, I really enjoyed this. The questions were unique and original and I really appreciated that. And I felt like it was a conversation rather than just like a series of questions. So I really enjoyed being here. Thank you for having me. I’m glad we could do this. Of course. And thanks for staying up late to both of you. Very late. Yes, sure. Yeah.


Simone Cicero

Thank you so much. It’s been fantastic. Shruthi and thank you. Yes, exactly. I mean, maybe mostly Shruti because it’s 2 a.m. on your side. So thank you so much, Shruti.


Shruthi Prakash

Thank you.


Shruthi Prakash 

No, no, thank you. Thanks for having me and thanks Jason for joining. It was very insightful.



I appreciate that. Well, thank you.


Simone Cicero 

For our listeners, I’m sure you have enjoyed the podcast. You can look at, you can head to our website, boundaryless.io/resources/podcast, and you will find this episode with all the transcripts and all the links of the things that Jason just suggested. And until we speak again, remember to think Boundaryless.