Be The First To Know

Welcome aboard! We are thrilled to have you.
Uh oh, something went wrong. Try submitting the form again.

Jason Fried

Jason Fried is the founder and CEO of Basecamp. Once a web design firm (and operating under the name 37Signals), Basecamp unintentionally pivoted into building software with their namesake product. They also created the email app HEY, a fresh take on an old idea.

Taking Risks
Taking Risks

Taking Risks

Ep
184
Apr
13
With
Jason Fried
Or Listen On:

You will figure it out.

Jason Fried is the founder and CEO of Basecamp. Once a web design firm (and operating under the name 37Signals), Basecamp unintentionally pivoted into building software with their namesake product. They also created the email app HEY, a fresh take on an old idea.

As you can imagine, Jason is no stranger to change. In this episode, he shares how Basecamp accidentally came to be and the struggles they’ve encountered along the way. Like working remotely, building new products, and taking calculated risks that from the outside might look crazy.

Change is inevitable, but it’s rarely easy, especially for a company where people are the driving force. Shifts in direction profoundly affect company culture, and how you manage that change can make or break your business.

Hosted By
special guest
produced by
edited by
music by
Appearances

Episode Transcript

Jason:

I'll figure it out is how I've always thought about things. I don't have a lot of confidence going into something other than knowing that the confidence is I will figure it out. And if I don't, again, I'm not putting myself at risk, so it's okay. And so it's a couple of those things together that gives me the confidence to try something new.

Chris:

I just want to tell you, I have a lot of mixed emotions talking to you right now, so I'm going to just try and be chill here. I'm excited. I'm inspired by you. I'm intimidated by you. And I have to just confess something. A lot of my thinking has been directly a lift from what you've written in your books. So when I don't know how it happened, when we exchanged information, I was like, I can't believe we're even going to talk right now. So I'm like, whew, deep breath. All right, so lot of admiration here.

Jason:

Well, I have loads of respect for what you're doing and I wish I was as good as you at what you do, so please. We're just two people talking here.

Chris:

Okay.

Jason:

We both are maybe good at something.

Chris:

We're good at something, I think.

Jason:

Yeah. Let's hope so.

Chris:

Okay. Now this might be crazy, but in case somebody doesn't know who you are, can you introduce yourself and then tell us a little story about who you are?

Jason:

Yeah, sure. So my name's Jason Fried, and I started a company almost 23 years ago, originally called 37signals. And you just interviewed one of my co-founders, Carlos Segura, a few weeks ago I think it was. We were a web design company and we were doing that for a number of years, and then we got pretty busy and we couldn't manage all the work we were doing with the tools that we were using. So we ended up building this thing called Basecamp that ultimately became a big deal for us, but at the time, we didn't have any idea it was going to be anything.
And I can get into some of the details, but we built that, launched that in 2004. And then from about a year later, we stopped doing client work and have been doing software ever since. We've launched a bunch of products since then. But yeah, so the company today is called Basecamp, although we started out as 37signals, and now we make Basecamp and we make something called HEY, H-E-Y.com, which is a new email service we just launched a couple years ago. And that's who we are. We've written a few books and done some other stuff, but that's the quick summary.

Chris:

Wow. Okay. Very succinct. I love where this is going. And even in that little quick introduction, now I've got even more questions. I got my questions on the side here, so let's see how this goes.

Jason:

Okay.

Chris:

You are doing what I think every creative person wants to do in that they can leave client work behind. I would just love to ask you what that transition was like from doing service work, and then now, you are your own boss, you're writing your own story.

Jason:

Yeah, it was unintentional, but probably secretly desired. We were doing client work, well, I was doing client work ever since I was in college, which is I graduated college in '96. And about '95, the internet sort of, kind of came around. The internet that we know it, the visual internet, when like Mosaic was launched, this is way back when. Anyway, I started doing freelance work. I actually did some work before that, just doing logos and stuff like that for some friends. But I'd been doing client work since the mid nineties, and then we launched 37signals, and we were doing client work.
And client work is, it's good and it's bad. It's great in that you get to do new things all the time. You get to take on problems that you don't have yourself, so you get to learn about other businesses, and do work that you wouldn't be able to do for yourself. And to do some work that's really high profile, and some work that's really personal, and you get to do a lot of different things. But then of course, you don't really, really ever you get to do exactly what you want, because you have a client who's paying you, and they're hiring you to do something for them.
Sometimes you can get that perfect client that lets you do exactly what you want. But we decided to make the software for ourselves, and again, we didn't know that it was going to replace client work for us. It was just is something we were actually building to do client work better. To stay more organized, to keep everyone on the same page, to have all feedback in one central place, so we knew who said what, when and who was promising what, and who was working on what, and deadlines, and alt tasks, and all that stuff. And it just turned out that product, as we started using it with our clients, they kept saying, "What is this thing that you're using? We have projects too. Can we, what is this?" And we said, "it's just this thing we built for ourselves."
Eventually light bulb goes on over your head. You're like, "There's an idea here. There's a product here." Turned it into a product, threw some prices on it, put it out in the market, not knowing what was going to happen. And then about a year or so later, it was generating more revenue for us than our client work was. So at that point, we decided to go all in on software because we got to be our own client. You're always working for a client. It's either someone else or you, but you still have things that you want to do, so you're always working for a client. And we just decided to work for ourselves, our client.
We wanted to be our own client. But that was only possible because we had something else that was able to pay our way, basically. I would not advocate basically going cold turkey, like dumping or dropping something and then starting something up from scratch with no safety net. I don't like that. So it sort of a gradual transition over a period of a year or so until we felt comfortable and confident enough that we could do this.

Chris:

That's the PSA part, in case you're thinking about dumping your very profitable business. You ready? That was the warning there.

Jason:

Be careful.

Chris:

Yeah.

Jason:

Yeah, yeah.

Chris:

I'm curious about this, because we've gone through this process ourselves recently, which is when you make that transition from being a service company to a product company, the culture has to change. The mindset has to change. And I found that in our own transition, it wasn't so easy for about 50% of the people. It really were other motivated where they could show up every single day, as a long as they know, here's the brief, here's the client goals, and they would do that. But when we turned over into being like, we're now our own boss and our own client, they didn't know what to do anymore. They weren't the autonomous people that I thought they were. So not everybody made it. I'm just curious what your experience was like.

Jason:

We were lucky because we were only five people when we made the decision to switch. So it was, yeah, there was five of us at the time. So we were all on board, right now, we're in the fifties of people, and if we decide to completely change our business model right now, it would be much, much, much harder. And this is something we've talked about in our books, this idea of mass. And this is just physics, the more massive an object, the more energy it takes to change its direction, and a company with a lot of people or a long history and legacy of doing something a certain way, when that company wants to change, it's very, very hard.
So yeah, I don't have advice around how to really change a bigger company, because that's just a totally different thing. But I would say if you were to do it, I'd probably do it relatively slowly, or spin up one group in inside of an organization to begin to change versus trying to change everything in everyone at once, which is just a really hard thing to do. I'm a big fan of gradual changes that become obvious eventually versus knowing that something's going to work for sure. I never know what's going to work. You just kind of make your way there until it either works or it doesn't, but you don't put yourself at risk.
The way I think about this is, there's a big difference between taking a risk and putting yourself at risk. So we try not to put ourselves at risk, meaning that if whatever we're going to do instead doesn't work, we haven't just sunk the whole thing. Our risks are calculated and they're gradual, so we can pull back if things aren't working or we can go forward if they are. But I don't like to make bet the company decisions. So I would recommend against that generally and sort of find your way there over time.

Chris:

Yeah. So I noticed this in doing that exact plan, there's the main company that's making the money, and then there's this small group led by me. And when I see a small, two people, me and an assistant, trying to build this other company, this other idea. And I couldn't help but to deal with the culture shift, and the observation that, hey, where the boss's attention is going, if we're not on that train or that boat, that's probably a bad sign for us. And so they can see that, and they're not dumb people, obviously. How do you process that? How do you talk to the team about that?

Jason:

That's a really good observation, because even if you don't want it to look that way, it looks that way.

Chris:

Right.

Jason:

Right? Whoever's in charge of something, where their focus is sort of where everyone assumes the important stuff is. And if you're not on that boat, then what am I doing? Or that sort of thing. So I think we have this too, when we go off and decide to build a new product. We have Basecamp, which has been around for, for 17 years and is a really strong, deep product. It's been around for a long time, has lots, tens of thousands of companies that pay for it. That's our bread and butter. That allows us to do some other things, and when we shift our attention, typically when we build new products, me and David, who's my business partner, will usually maybe pull one other person in and we'll do the explorations on the new product.
And so we're not on the main thing for a while, and you can imagine people wondering, well, is this main thing important anymore or what? The thing is with us as a company is that we don't have anyone dedicated just to certain parts of the business. We have different people in different roles. So if you're in customer service, you do that. If you're a designer, you do this. If you're a programmer, you do this. Ops, you do that. But what I mean is that everybody works on all the products. So for example, when we were building HEY, people who were working on Basecamp previously knew they would ultimately be working on HEY also once we got it so aware. So it wasn't like they were being left behind and only focused on this other thing. They knew that they too would transition if the company transitioned.
So I think that's an important thing, at least for us, how we've done it, which is that everybody gets to move back and forth, and work on different products. So right now we're working on HEY and Basecamp simultaneously, and we work in what we call six week cycles. This cycle you might be working on HEY, next cycle, you might be working on Basecamp. So it's not that you're ever left behind or that you're ever pulled along. We just are constantly shifting, but also communicating clearly to the group, like, "Look, right now, a few of us are going to focus on something else for a while to explore it. It's an exploratory exercise. It's quite risky. We don't know if it's going to work. So it's not even a great place to be. It's maybe more exciting, because it's on the forefront or something or pioneering something new, but it also could fall flat."

Chris:

Right.

Jason:

So I think you have to communicate that and and recognize that everyone's going to come along for the ride, if we find out that there's somewhere to go.

Chris:

That makes a lot of sense as you're going from product to product. I guess the struggle for me was there's a service company and a product company or an education company that they could just not even figure out. It looks like the boss is going to do something crazy, having a midlife crisis or something, and it's kind of, I could be objective about looking at it. There's this crazy thing that makes no money.

Jason:

Yeah.

Chris:

That'll take years to develop, that there's no guarantees of outcomes, but all the attention, at least from my point of view, was directed there. And so that did cause some real concern.

Jason:

I can see that. I think it's a natural human response too, but I think one way to put it is that the other part of the business, the traditional part of the business, is the engine. If it didn't exist, we couldn't do these other things. So it is actually the most important part of the business.

Chris:

Right.

Jason:

Because it fuels explorations in other directions, but naturally you're still going to have just some of the human stuff. Like, am I working on the latest and greatest? Do I get to work with the person who maybe I came here to work with? Well, maybe not for a while. Are we jettisoning our old stuff? Or are we going to do both? Or are we going to transition? And it's the unknown that I think makes people feel uncomfortable. So I think the more you can explain sort of why you're doing this, and where you're headed, and what this is all about.
And it can be, about stability. "We want to have multiple revenue streams," or, "We just feel like we want to go in a different direction, here's why." You just have to explain and be clear about it, as clear as you can, and also recognize that people are still going to feel perhaps a bit left out or nervous that they're not on the other boat at the moment. But I don't know if there's much you can ultimately do about that, other than to be upfront, and clear, and transparent about it as best you can.

Chris:

Right.

Jason:

This is what's hard about organizations. This is what is hard about people. This is what's hard about companies. The work is always challenging, but really it's managing people that's I think the hardest part of it all.

Chris:

If you ever work with people, especially creative people, you know the pain of this. It's never that straightforward.

Jason:

Yeah.

Chris:

We're emotional. We're irrational. We fall to some of our worst selves sometimes about jealousy and whatever it is, insecurities, and sometimes communication can handle that. Being transparent, as you said, will help with that, but it's still going to exist as long as you work with people with real emotions, right?

Jason:

Yeah. Yes. And we all have it.

Chris:

Yeah.

Jason:

It's not like they have it, it's we have it. It's just we all have it. One thing we try to do is when we're working on something new, like an exploration for new product, is we will try to, not super early. This is actually a good topic by the way, around feedback, and getting more eyes on something, and when you want to do that, because I don't believe you want to do it too early. I think some people feel like you want to get a lot of eyes on things early. I think it's really good to protect something early for a while, because it's really fragile and there's a lot to go into there.
But what we do is when we get to a point where we feel like we've got something we're particularly excited about, we'll just begin sharing that throughout the company. Just so people can see what we're doing over there. It's like, "What are you doing over there?" Well, here's what we're doing. And I think once you begin to share it, people then begin to feel like they're part of it. If you just are totally secretive about it, and I know there's probably some examples, like you can imagine with Apple when they were making the iPod, they couldn't show anybody anything. There's only 10 people. Okay, but you're not Apple and I'm not Apple, and it's okay. Like, we're not.
So you show early versions of things when you get to a place, and if you don't want feedback, you can say that too. Go, "Hey, I'm not sharing this to get anyone's opinion. I just wanted show you what we're doing over here, so you have a sense." And just set the expectations, but I think people appreciate being able to see what you're doing over there. That's a big part of it.

Chris:

Yeah. That's a great tip, to include people, but also say, "I'm not necessarily looking for your feedback here. I just want to be inclusive."

Jason:

Yeah.

Chris:

Love that.

Jason:

Yeah.

Chris:

I think, I get this feeling from you that this is one of your philosophies, which is to do less but better. So I'm just curious, I've seen 37signals expand in products and then shrink back down, and then here you are talking about another company, another idea, another product. If we don't want to add things to our plate, then what is the genesis or catalyst for you to say, "I got a new itch. I have an observation or something that's going on here that I'd like to explore"? How do you manage that?

Jason:

Terribly. Because this is what happened. We said like, this is about I think six or seven years ago. We're like, "Okay, we're just going to go all in on Basecamp. We're going to rename the company from 37signals to Basecamp, which is going to signal the fact that we're just focused on one thing, and one thing's enough. We're going to do our best work on our best product we've ever made." And you do that for a while, and you inevitably have a million other ideas, but you always do.
And then every once in a while, one idea just won't leave. It won't leave you, and this email thing wouldn't leave us. So we use Basecamp to run our whole business, all of our internal communication, all of our project management, all of our vendor stuff, but we also use email for the outside world. So when we're communicating with lawyers or accountants or the public or whatever it might be, we use email. And so since we're tool builders, and we want to build our own tools, and we've already built our own work tool on the Basecamp side, we wanted to build our own email tool because that's what the other thing that we're in most of the day.
And we just couldn't stop exploring this idea once we started getting somewhere with it. However, the initial idea for HEY, which is sort of what we're talking about, was actually redoing a product we built earlier called Highrise. We started exploring CRM and stuff, we wanted to see if we could do a new version of that, but we just had this itch to do something else. And one of the reasons why was because we realized that we become a more innovative company when we do at least two things. I think we started feeling ourselves going down a narrower path wasn't allowing us to be as creative as we wanted.
Because when you work on something that's been around for a while, there's a lot of legacy limitations. You can't really explore a lot of brand new things, because people are already used to a certain way in a certain thing. And so when you do a new product, you have a chance of starting from scratch, and those ideas fuel then you're other thing. And you kind of go back and forth. We're calling this, we kind of call it internally tick tock development, like tick over here, tock over there, back and forth and back and forth.
And so now we brought a bunch of the ideas from HEY into Basecamp, we're bringing stuff from Basecamp into HEY, and now we're able to play a little bit more and have a little bit more flexibility and freedom to explore things and not say, "Well, this doesn't fit into Basecamp, so we're not going to explore it," but now we can. But here, the truth is we're actually going to explore two more products too, at least. So we have two more product ideas. Now that we've torn the lid off or ripped the bandaid off or something, I think we're going to go back to what we already are with Basecamp and HEY, but we want to go back to being a multi-product company that's beyond even just two products.
So we're going back to the beginning, back to the basics. Or not really the basics, but back to the original thing, which was build the kind of things we want to see exist in the world and not limit our ourselves to some artificial limitation that we had. And let's see what we can build. If we have an idea, let's explore it. And some of these ideas may go nowhere, but we're not going to say we're not doing it anymore. So that's the new revision. And I feel like 23 years in, it's sort of fun to say, "Well, what if we stop doing things the way we were doing them? Why not just do in a new way?"

Chris:

Right.

Jason:

For now, for the next six years or 10 years, I don't know. You just get that degree of comfort and confidence when you've been around for a while, and it's a good reminder though to change, because the longer you're around, the more calcified you become, and you kind of get stuck in your ways, and this is a way to break out of that.

Chris:

I love that.

Jason:

The other thing I will say though is that specifically, one of the reasons why we cut back on our products was because we didn't want to grow bigger. We wanted to keep the company as small as we possibly could. That was just something we've always wanted to do in terms of people. Because we wanted to know everyone's name, and want to just have a very small business culture. And we decided recent that, you know what? We don't want that limitation on us anymore, and therefore we can hire more people so we can do more things. We couldn't do more things with a really small crew, but now that we're willing to get bigger, we can do more things. And so we took that limitation off. We're not getting to 1000 people, but maybe we'll get to 100 people or 120 people. If we had that, if we had a more capable company, what could we build? And that's sort of our current mindset.

Chris:

Ooh, there's a lot there. Okay. I'm just curious when you said that sometimes you need to do two things because they inform each other. Is this kind of in alignment with this idea that sometimes when you're staring at a problem so much, it's hard to think of it in new and innovative ways, but as soon as you start looking at something else, working on that, and then all of a sudden your thinking opens up, and these ideas then inform the previous company, and that interplay between the two.

Jason:

Yes, and I'll go broader than that too, which is when I look for inspiration, I don't look at my own industry, because looking at my own industry is like looking at your own product, in a sense. If you just look at your own industry, you tend to sort of do what everyone else is doing. And so when I'm looking for design inspiration, I look towards architecture or I look towards gardening or I look towards plants and flowers or animals. I look at other things. If I'm trying to figure out what colors work, I look outside. I don't look at other products and see what what colors people are using or what palettes this app has or whatever.
I look outside, because nature's always got it figured out. Nothing in nature looks bad, you know? So I'll look there or if I want to get a sense of how something feels, I'll go walk into a beautiful building and think about, why is this building beautiful? Why does it feel good? What's good about it? Is it the textures? Is it the way materials come together? Is it the scale? Is it proportion? Is it the setting? What is it? And that's the kind of stuff that just gets me to think about software, in a strange way, because it's unrelated to software. If you were to really lay it out, it's unrelated, but it's also very related in that it's about space, and function, and feeling, and all those things.
So I think that's, part of the reason of having two things is to be able to see a different perspective and try something else, but also broader getting away from your own thing, and I'm going to broaden that out to my own industry, and look at other sort of related kind of things to get ideas. That's how I've always found, because I remember when I was coming up initially, I would always look at like Communication, Arts, the print. Or Print actually was another one where it had business cards and letterhead, and I got ideas from that early on.
I remember, but what I was getting when I was early on, I was getting ideas for things I wanted to copy. And I found that the more I looked at my own industry or similar things, actually the less creative I felt myself being. I felt myself becoming a good copier, which was a good thing, good way to learn initially. Like how could I recreate that or how could I make that? But I wasn't coming up with my own ideas until I got away from my own industry, and looked at other things, and then tried to figure out how to incorporate those back into the work that I was doing. So that I think is a related point to the point you brought up about having two products and taking one thing from another.

Chris:

Thank you for expanding on that. And I talked about this with my design students back when I was teaching in art school, is that creativity is your ability to find a connection between two or more disparate things. And the farther apart those two things are, the more we're going to say that's really creative. When you can bring in something, just totally like a nonsequitor, non-related thing, and you bring it into your thinking, that is where people are like, "Wow, that is crazy, cool, unique, interesting," whereas if you just look at design in the industry that you're in, then it becomes very... I guess it's you're just regurgitating an idea and putting a slightly new coat of paint on it, but it's really the same idea seen over and over again. And thanks for opening that up.

Jason:

Yeah. Like for example, on my desk right now, I have rocks that I've collected. There's nothing special about the rocks other than I like the way they look, and the textures, and the colors, and the shadows, and the shapes, and the proportions. I just, I don't know what it does to me, but I like having them around me. And I feel like whenever I'm working on a design or something, I tend to look at the rocks and go, like, "Why does that work? Why does that rock work aesthetically?" At least for me. And this is, of course, always a purely subjective thing. There's no objective thing probably here.
Or like ceramics is something I really like, and there's a few artists I really like, and I'll have their stuff around. It helps me think about proportion, and color, and shape, and size, and I don't know, it gets me going versus looking at other apps or looking through a book of design stuff, you know?

Chris:

Right.

Jason:

It's one of the reasons I love furniture so much. Furniture is another one of those things that I just look at that and I get ideas from it.

Chris:

I don't want to go too far on this, but are these fancy rocks or these just rocks you found while walking?

Jason:

These are, I'll just get one for you, even though I think our viewers probably won't see it, but it's just like, this is a rock I found on the beach.

Chris:

Yeah. It's got some holes in it.

Jason:

It's got some holes in it, but it's like, I just like the way it looks. I don't know. There's just a lot of textures, and shadows, and there's some really interesting lines on it. I don't know.

Chris:

I see that.

Jason:

It's just that.

Chris:

Okay.

Jason:

I also have this, which is like a called a desert rose.

Chris:

Whoa.

Jason:

Which is a neat thing. I didn't find this, I bought this. It was like $10. It's not a fancy thing, but I just liked it.

Chris:

Yeah.

Jason:

And I don't know.

Chris:

That's really unique.

Jason:

Yeah. It's just having stuff like that around that, org designed objects, whatever. But again, I'm trying not to look at software when I build software. That's kind of the point I'm trying to get at.

Chris:

That makes sense, yeah. And for the people are listening to us, what was the second rock he held up? It looked like a bunch of like tumbleweed glued together, but out of stone.

Jason:

Yeah. I think it's called desert rose. I think if you look it up, desert rose rock or something like that, you'll see it. Yeah.

Chris:

Okay. The reason why I asked you if it's like a fancy rock, because I imagine like, I don't know if they're called, are they crystals? Or like when I go into fancy people's homes, they have rocks of are cut in half and there's like crazy colors in them that are brilliant. And I just think, wow, nature has its way. It's so incredible. That's kind of what I imagine. I'm glad to see, it's like these are very earthy and natural looking.

Jason:

Yeah. Yeah. These aren't those, I think they're called geodes or something.

Chris:

Geodes.

Jason:

The ones. Yeah. Yeah, I don't have those. It's not like a crystal thing. It's more like just I saw something on the beach that I thought was beautiful, and I picked it up, and I put it in my backpack, and brought it home, you know? But those things are beautiful too. And I'll love to go to those kinds, whenever I see a store like that, that has those natural big things that you'll walk through it. Because like the geometry and the colors, and the fact that some of these designs are locked inside of something else, and you weren't really meant to ever see them.
It's beautiful. I don't know. I also, I love birds. I love looking at birds, for colors especially. One of my favorite birds is this bird called the cedar waxwing. And if you look up the cedar waxwing, and you look at it, it's just beautiful. The colors are so unexpected, and the way they blend into themselves, it's just stunning. And I know I get ideas from birds and from colors in nature.

Chris:

I guess the lesson to learn here is that there's so much more you can draw inspiration from if you're willing to look and pay attention.

Jason:

Yes, and it's everywhere. You don't need to go far. You just walk outside and look around. Another thing I like to look at really closely or leaves and flowers. I mean, if you look at a flower from afar, it's beautiful, but when you get up close, it's even more beautiful. Because you see a lot of intricacies and little, little, sometimes like multiple shapes, almost a fractal thing going on. And they're very delicate, but they're just incredibly beautiful and intricate, and ornate, and you see colors blending into other colors and it just, they always work.
You'll never find a flower that doesn't work aesthetically. It's just not a thing. Which is an incredible notion in itself, that there can actually be something that always works. Somehow, I don't know how, but it just, they're beautiful. So anyway, I'll look at that kind of stuff, and now I'm sort of belaboring the point, but yeah. There's inspiration everywhere, and I would encourage people to look far outside their own industry and their own trade for it.

Chris:

Okay. I'd like to take you back to something that you had said, because I think it's the beginning of something else, but I'm not sure. I'm suspicious. Like I don't know who said this, but I heard it from Blair Ends who said all strategy is autobiographical. And it made me think like, is that true? I guess it is. And so when I listen to you, and I connect them to the book, it just makes perfect sense because everything you say, everything that seems to be how you're guiding your thought and your words, is reflected in the book. Like when you said at the beginning, there wasn't a grand plan. In the book and rework you write planning is guessing, and it's just by listening and keeping things small, you are able to kind of not feel the pressure of doing so much at the same time. So just keeping things super simple.
And you talk about mass, but now you're talking about potentially growing the company, getting to multiple products, and maybe disrupting your own way of thinking. So I'm wondering if the next book will be called something like with re in front of it, but maybe it'll be like rethink. So you challenging yourself.

Jason:

It's really funny that you mentioned that, because David and I have been talking a bit about that. This just feels like a moment for us to reconsider, is really the way I was thinking about it.

Chris:

Yeah.

Jason:

Reconsider a lot of assumptions, preconceived notions, and recognize that we're in a fortunate position where we can build the business and try something else, and it's still the same thing fundamentally. We're not talking about, we're not raising outside money. We're not trying to be a unicorn. None of that stuff. This is like one step away from where we are today, but just becoming a more capable company. And that requires us to reconsider a number of things in terms of hiring middle management. We need to bring in some more managers, we need to bring in some more leadership that's more strategic minded versus just individual contributors.
We primarily hired individual contributors over the years, and now we want to hire some people who are coming into leadership roles from the start, and it's scary and unknown. And some days you're like, "What are we doing? Why are we doing this?" And other days, you're like, "I'm so glad we're doing this," and we're in the middle of it. So I don't know how it's going to turn out, but it's kind of like, why not try this now? We've been doing this for a long time. We know how to run the business the other way or the way we've been doing it. Now let's challenge ourselves to do it a little bit differently.
And we know we can do it because we've done it before. We used to have four products and we had four products with like a team of 12. So certainly we can have multiple products with a team of 80, even though things are harder today because now you have mobile apps, you've got more stuff that you need to build, higher expectations, more platforms to cover, but we should absolutely be able to do this.
Yeah, I think the book would probably be reconsider or like re-rework was another title. We don't have a book in mind yet, but, or reworked, I don't know. It's exciting to think that in a few years we'll be able to reflect probably on the changes we're making now and take some lessons. So part of the reason why you might find some continuity between the book and what I'm saying is because the book is based on what we've done and what we think. It's not theoretical. It's very practical. And so we can only write another book once we have enough lessons that we've built up and experiences that we've had, and we then put them down on paper. So we're not predicting where we're going to head. It's actually a summary of where we've been. And we'll see when the next one comes out, if we ever do another one, it'll probably be about this transitional period right now.

Chris:

Right. So this will serve as an interesting time capsule or timestamp on your thinking. And I get that, like the books are reflecting back what has worked, and what you align with. So if that changes, then it would make sense then for you to release that book, because people wonder like, "Okay, so they're doing things differently now. And we're curious as to how they got here." And then you can tell that story, right?

Jason:

Yeah. That could be the plan. So we don't set out initially to decide to write books, but often what ends up happening is we come up with a title for one, and then we have to do it, because we like the name. I'll do the same thing with product design, whenever I come up with a product name. I'll give you an example. So we're thinking about building a new calendaring system, which is going to be more than just a calendar, and it'll be related to HEY, our email thing, because email and calendar seem to go together. But also it will probably stand alone. By the way, I'm sharing things that are not solidified yet, so please no one quote me on this, but this is what we're thinking about. And I came up with this name Heyday, which is like the perfect name for a calendar in my mind ,that's related to the product called HEY, and also there's something more to it.
And now I almost feel like we must do it because we have a good name for it. Now that's not the only reason to do it, but that's one of the things that gets me excited is a good name for something. But yeah, I think the plan will be to reflect back on this period of time in a few years and see if there's anything new to say. And if there isn't, there won't be a book. If there is, there will be. And I think what's interesting about this period of time in the company's history is that it's growing is challenging. We have to do a bunch of things we've never done before, and most of these things are things that we've railed against in the past. So you have to fight your own religion, in a sense, and get past that.
I find that to be really exciting, but it can also be really hard, because sometimes you do something you're like, "We're not supposed to do that." Like, "Who said that?" "Well, we said that." "Well, if we said it, we can say something else." You know? It's our own, you fight your own rules that you set up for yourself. And then you have this expectation to live up to your past because you want to be consistent. But I'm much more interested in context than consistency, and the context today is different than it was before. So let's do something different and not worry too much about it.
Anyway, these are these thoughts that float around in your head, and I think I've always taken comfort in the fact that I don't really know what I'm doing, but I plan on figuring it out. Like I'll figure it out is how I've always thought about things. I don't have a lot of confidence going into to something other than knowing that the confidence is I will figure it out. And if I don't, again, I'm not putting myself at risk, so it's okay. And so it's a couple of those things together that gives me the confidence to try something new.

Chris:

Well, either way, I'm curious to wherever that takes you because it'll either confirm like, "Nope, the original philosophy and religion was really solid, even though we tried to break it ourselves," or "Hey, you know what? Sometimes it works like this and sometimes it works like some other way and everybody find your own way."

Jason:

Yes. Which is something I really appreciate I think in the interview you did with Carlos, he was talking about how I think he thinks advice is bullshit or something like that. This idea that everyone's situation is so different, timing, context, other situational variables, luck. So giving advice is, I mean, I give it, but what I really I'm trying to say, like, this is what's worked for me. I don't know what's going to work for you. I don't know what's going to work for the future version of us even. I don't know. But you got to pick a direction and go with it and see what happens. But yeah, I think that's a good observation.

Chris:

Time for a quick break, but we'll be right back. Welcome back to our conversation. I'd like to make a hard pivot right now and talk a little bit about how you wrote the blueprint for 2020 in 2013 in the book Remote.

Jason:

Oh.

Chris:

And it's really interesting because I did not read it in 2013, but we've been living some of those philosophies, and then when I read it, kind of like, oh my God, this is the way. And we've seen what has happened to businesses all over the world because of COVID. And you wrote this idea that there's a bunch of things in the book, but about decentralizing your office, your operation, to prevent it from catastrophic failure if one system goes down. And you're making a case for distributing the workload across people and allowing people to work remotely. And I'm just curious about your thoughts, having written that in 2013, and seeing just the economic devastation, not even to talk about the health impact that COVID has made. But I'm just curious, seven years prior to this happening, you already kind of wrote about it. What are your thoughts on that?

Jason:

Yeah, obviously we never could have predicted this terrible couple years, but remote working ultimately is about building resilience in an organization. The ability to work from anywhere, anytime, and hiring people from all over the place. And remote working is not just working locally far away or far apart. It's actually a fundamentally different approach to work. It's a more trustworthy way of working. It's more about asynchronous communication than real time. Especially as you go across time zones, you can't have real time conversations with people who are seven times, I mean you can, but it's much harder to synchronize schedules that way, and people end up working longer and later because you're pulling people into conversations when it's nighttime for them, and it's a very unhealthy approach.
So I think there's a lot of good fundamental ideas behind remote work. Even if you are working locally, to work asynchronously and to trust people more, but it is about resiliency. And I think that what ended up happening here with COVID is that a lot of companies found that they weren't that resilient, and that if their office went away, they would be scrambling, and they wouldn't know how to work. If they only relied on in-person meetings, and they thought there was no other way to work than that, and they couldn't have them all of a sudden, they were caught flat footed and didn't know what to do. And so remote working just gives you another option. That's at the fundamental level.
But the other thing that's great about remote working is you get to hire people all over the world, and you're not limiting yourself to hiring people just within 30 miles of your zip code or your home office or your office or whatever. You can hire incredibly great people all over the place, and they are everywhere. There's a tendency in the tech industry to fight all over the same people, that there's this talent war for whatever, for the best 50 or whatever. I don't know. I don't buy it. I mean, of course there's incredible people and there's a top 100 people, whatever. There's another 10,000 that are exceptionally good. There's another million that are exceptionally good in other places. Go out and find them.
And that's what we've always done. We've never tried to fight the talent war, we just find wonderful people all over the place. And the only way you can do that is if you have a remote working culture where you're not afraid to hire someone who lives 4,000 miles away or seven time zones away. So yeah, we weren't pressing here. We didn't see the coming terrible COVID pandemic situation, but we'd always worked this way, and we thought it was a valuable way to work, just another skill to have.
And I think it makes companies more resilient, because look, let's say you've worked remotely now for two years and you decide or your company decides, we actually prefer working together. We all have to get back together. Okay, fine. So you pull everyone back into the office, and then maybe the building is sold, and your lease is canceled, and you don't have a new office space to work out of for a year. Now you're going to feel like, well, we can get by. We're going to be okay because we've learned how to work remotely. Like we have resiliency here. It's not just about pandemics. It can be all sorts of other reasons why you can't get together, and I think that's just a good skill for a company to have.

Chris:

Well, I think in 2013 it felt like it was a radical philosophy, a way of thinking that would never work for most companies. Like you guys are very unique in that you're a software company, you can do things remotely, and you have enough profit margin relative to overhead that you can do whatever you want. And we saw the resistance at the beginning, and then acceptance, and adaptation afterwards, where gigantic corporations were saying, "Moving forward, we're no longer requiring you to show up to work anymore." And they found what you about, the kind of hypothesis that once people get over it, they're actually more productive and more effective, and you can trust people to do work at home. You need to support them. You have to have systems in place, but it's fascinating to me that it all kind of really played out the way that it was written.

Jason:

The well, the other thing is that to me, it's more respectful at a human level. If you're forced to live near where you work, you have to close a lot of options off. Maybe your partner has to move because they have a job in another city. Maybe they're, like I have some friends who are teachers, and they're very specific teachers, university teachers in a very specific topic or subject area. And there's only like three of those departments across the country. And if a job pops up somewhere in Connecticut, they got to go there to get that job. But their partner, they lived in, I don't know, let's say San Diego. And now someone has to leave their job. Someone has to lose their job because they can't live near where their other job was, so their partner can.
It's like, there's so many fundamental life decisions that come with where you work when you're locked into a place. And what's nice about remote working is that you can choose to live your life and live wherever you want, within reason, you need to have a certain overlap with your team and everything. Work becomes less influential on your life. Even though in some ways you feel like it has more influence because now you're free to do other things, but that's actually because work has less influence on your life. And now I think that's a really healthy thing. Now, granted, not everybody can do this. There's many, many jobs, you work in the restaurant industry, you work in a factory, you work with manual labor, you assemble things, you can't. You have to be there at the job site to do the thing, obviously.
But if you're an information worker or creative or many, many, many, many industries now, you can choose to live where you want. If you want to choose to live in a new place so you don't lose your job and the company doesn't lose you, there's so much good that comes from that, and I think people's lives open up. And I think it's nice to have employees who don't feel locked down into a certain thing, to a certain place anymore. They feel more open to living the life they want to live. I think that's good to have always like that. And it's good as a company to support that.

Chris:

Since you can work wherever you want or live wherever you want, where do you choose to live? And this is a question my wife and I ask ourselves all the time. We could be anywhere doing what we do today and no one would be the wiser. So I'm curious, I'm seeing you in a space. I am assume it's your home, but I don't know where you are. Where are you?

Jason:

Yeah. So, well, I'll tell you where I'm at in a second, but I lived in Chicago my whole life, basically. And I went to school in Tucson, Arizona, so I can get out of Chicago for a while, and I went back to Chicago afterwards. Then a couple years ago, actually during the pandemic, my wife and I, and we have two young kids, seven and three. Now they're seven and three. They weren't of course back then, they were two years younger. We decided to come out to southern California, primarily because of the pandemic. We felt like schools were going to be shut down in Chicago or we'd be locked in the basement in the winter, and we didn't know what was going to happen. And so we felt like, well, at least in a warm climate, we could.
And there's many other warm climates, but California was something that was appealing to us. We could be outside. Our kids could, maybe school could happen outside. Schools were starting to happen outside. We could spend more time outside and not feel like we were cooped up inside, which is what happens in a cold weather city in the winter. You feel cooped up, basically, especially with young kids. So we came out here, and we're staying out here for now. I don't know how long we'll be here. We might be here forever. I'm not sure, but it was driven by a life decision. And then our work obviously allowed us to do that, which was great. And it wasn't just that, because I own the place I could do it. Any employee could do it.

Chris:

Right.

Jason:

That's the other thing. You can't have these things that this person could do, this person can't. That's that just doesn't really pan out. You've got to allow that flexibility to everybody. I know there's been some companies that have allowed executives to be remote, but not someone else. It's like, that just doesn't work. Either it's all or nothing. Unless of course, again, like you might have a company that has retail locations, and people in retail have to be there, but people in corporate don't because they're not customer facing. That's a different story perhaps.
But anyway, yeah, so we're in Southern California at the moment, enjoying the weather, and the sunshine, and being outside as frequently as we can be. I don't know where you are. Where are you?

Chris:

I'm in southern California as well. I'm in the Pacific Palisades.

Jason:

Okay. We'll catch up later. I'm not too far from you.

Chris:

Okay. All right.

Jason:

Yeah.

Chris:

So I was suspicious because I'm like, it's awfully warm and sunny in Chicago today. And I was like, so you must be somewhere else.

Jason:

Yeah.

Chris:

Okay. I have a question for you because I just noticed this about myself. I was mostly working from home, but there was this option to go into the office and see the team and people can come and go if they need. As long as they figure out what they're doing, we don't really care. We have very few manager types. And then the pandemic happened, and now I'm in this weird routine where I'm just at home most of the time, and it's starting to take a toll on me. I do go out for walks. I do exercise, but I think you have probably a head start on all of this because you've been thinking this way and working this way. How do you kind of keep fatigue of just doing the same thing and not being social with people at bay?

Jason:

Yeah. Well first off, the last two years have not been remote work. They've been pandemic work, which is a different kind of thing. Because typically with remote work, you could go to a coffee shop and hang out, or you can go to a library, or a co-working space. You could see your coworkers if they live in similar cities. Over the last two years, I mean, now it's loosening up, but you really couldn't do any of that, so it was hard.

Chris:

Yeah.

Jason:

It was extra hard. A lot of isolation, very difficult socially, especially for people who are single, who don't have someone else they're close with or able to be close with. It's really, really hard. So hopefully that's going to loosen up here soon, and people are going to be in certain parts of the world. It already has, certain states it has. People are going to find out that remote working is actually probably better than it's been over the past couple years.
For me, I take a lot of walks. I have actually, to be honest, I wish someone to start a podcast called walking, and the conversations would all be required, you'd be required to walk. So I don't like sitting down and thinking. I don't like sitting down and talking. I have a hard time with it, actually. I prefer to move. So I like to move around a lot, I like to think a lot when I'm moving, that kind of thing, so I'll do that. Having two young kids just keeps me very occupied. So I don't actually have a lot of time to see a lot of other people at the moment anyway.
And I'm pretty introverted to begin with, so I don't need a lot of social interaction, but I do feel when I don't see other people, I feel cooped up. And I think if I was cold weather city it would feel especially hard.

Chris:

Yeah.

Jason:

So we're not doing it right now at the company, but we used to do these things where every once a month, pick five random people at the company, and send them basically a Zoom link like an hour ahead of time. And we would just have five people just randomly chat across the company about stuff, anything that's not related to work. And that was a nice way to at least run into other coworkers that you might not normally work with, because you're not working with them on a project, but you have some of that social interaction, but of course not in person, it was all remote. So it didn't quite satisfy the personal thing. But I have found that simply even going for a walk and not interacting with people, but just seeing other people around, really helps my mood. Just knowing there's other people out there is helpful. But I know if you're really extroverted and you need to be with people, it's been especially hard I would say over the past couple years.

Chris:

Yeah.

Jason:

I mean, do you have any tips for this? You say you're feeling cooped up and what do you do?

Chris:

You know, I took the whole self quarantine thing very seriously. I have elderly parents who live close by, and I think if I got something I'd be okay, and even if I didn't recover from at least I could live with that, because it's just me. But seeing them, I just had to be extra careful. And so it's like, I just pretty much like got locked into routine, so it's been really tough. It has been super, really difficult because I'm an introvert, but I feel drained too. Like Zoom is not the same thing as real life. You could see people, you can hear them, but it's not the same. And so I'm making a point just sometimes get in the car and just driving with my wife to run errands, even though I'm not doing anything, at least it's just interrupting that pattern. Because otherwise, I'm sitting at this box or walking around the house, but there's not a lot of other places I'm going to.

Jason:

Yeah. Yeah. And I know the elderly parents side of it too. So I hear all that. Yeah. It's been a weird time, but I think whatever you can do that makes you... Everyone has different requirements in terms of interaction and what they need to fuel themselves, and trying to get closer to that, even if you can't do that exactly, I think is going to be helpful. Just like if there's a heat source, you don't need to be on top of it to feel it, you can be, but the further away you are from it, the less you feel it. But as you get closer to it, you start to feel some of that heat. And I think you can think about that with people, if you need some of that.
I think that's what I would recommend. But yeah, I'm hopeful that in the next year or so here, it's going to be a lot more normal, of course, and we'll be able to see the people we want to see with and do the things we wanted to do.

Chris:

Right. It seems like that's the case. Okay.

Jason:

It seems like.

Chris:

I have a serious question and a not so serious question for you. Just being mindful of time here. So the serious question is this, it seems like the things that you write about, and from what I can gather by watching your videos or listening to you, is that you place an importance on just uninterrupted time to think, to work, to do whatever you need to do. I think Peter Drucker in his book, The Effective Executive said it's a priority for an executive to consolidate the largest amount of discretionary time. Okay. So if that's your philosophy, your ethos, what do you do with your time? Like assuming that, you know what? There's no meetings, nobody's bothering me. I noticed no one's messaging you right now. So there's a lot of this discretionary time. What do you do with your time?

Jason:

During work? During the work day basically?

Chris:

Yeah.

Jason:

Yeah. So this is a fundamental tenant at Basecamp, which is, I feel like my job is to help people protect their time and attention, because it's the thing everyone else wants from each other. And the quality of an hour is incredibly important to me. So there's a bunch of different ways to slice 60 minutes, but the best slice for me is 60 minutes. It's not four 15 minute blocks. It's not two 30 minute blocks. It's 60 minutes straight. Uninterrupted stretches of time. What do I do? I think, I draw, I sketch, I work on new ideas for the products that we're working on. I reconsider how we're doing certain things. I write a lot.
And those are the kinds of things that I can't do in fragments, although I will also do them in fragments. Like an idea will pop into my head at nine o'clock at night when I just put the kids to bed, and my wife and I are having a chat, and then I have some private time or whatever. Like something will pop in my head. So things do just come in fragments of course, but I feel like I can't work through those things unless I have long stretches of uninterrupted time. And this is not, again, just a privilege for me because I own the place. This is something we're very careful about with everybody, which is why at Basecamp, we rarely have any meetings. We don't have what we call presence, so our products don't have a little red or green or yellow dot next to your face showing you if you're available or busy.
The assumption is that everyone's busy working on their own thing, and you need to respect people's time and attention. So don't reach out and try to grab someone. If you have a question, write it up in long form, and post it to Basecamp, and let people get back to you when they have a chance versus when you need the answer immediately, unless of course it's truly urgent. So downplaying this idea of urgency. This is a cultural thing though. Everyone has to sort of believe that urgency is overrated. ASAP is poison, unless it's absolutely truly necessary, and then you do grab someone.
So when you go more toward asynchronous communication, when there's no expectation of immediate response, people end up having the ability to even have two or three hours to themselves, uninterrupted. Maybe then something comes up and you deal with it. But ideally, I want everyone at Basecamp to have an eight hour day to themselves and they can decide how they want to spend that with their team and whatnot, but that's not like, well, my first half of my day is just absorbed by meetings and then I've got an hour and then I got another thing and I've got an hour. I got another thing. So I have no time really to really work through things, and so now I'm going to work late at night or in the mornings or on the weekends because I don't have any time to do things at work anymore.
That's an unhealthy place to be. So we try to push all that, all those distractions to the side, and give everybody long stretches of time. And when you have that, you can actually achieve a lot in a little. So we work about 40 hours a week per person at Basecamp. We're not pulling all nighters, there's no 70-80 hour weeks. There's no weekend work, unless you're on a weekend shift for customer support, something like that. 40 hours a week is plenty of time, if you have about eight hours a day to yourself. If you have two hours a day or an hour, it's tough because you had things to do and you can't get them done in that short period of time when your day is sliced into a billion pieces, it's really hard.
So that's a fundamental thing that we're able to get a lot done in a short period of time, in a reasonable amount of time, because the quality of our hours are high. And the more of those hours you can stack back to back, like it's kind of a super power to have three hours to yourself straight through. That's just something most people don't have. I remember I spoke at a conference a number of years ago, everything was now a number of years ago, conferences. And I just asked people, there's like 600 people in the audience, "Put your hand up if you've had four hours to yourself at work in the past month," or something and like relatively no hand, maybe 5% of the hands, you know?

Chris:

Right.

Jason:

That's sad to me. It's sad that people don't have four hours to themselves at work. And so we're trying to make sure that's like every day at Basecamp is sort of the aim.

Chris:

Yeah.

Jason:

Of course different jobs are different. Like if you're in customer service and you're answering tickets, that's a different story, but at least you're not being pulled off in meetings, and then also having to answer tickets, you know? So we just want to make sure that the thing that you're doing is pretty much your only focus for the day. That's the aim.

Chris:

You know, one of the things I recognized early in the pandemic was I was exhausted at the end of each day in ways that I wasn't exhausted before. And then it dawned me like a month and a half into it, like, why am I so tired? What is going on? Because I was working uninterrupted for eight to 10 hours a day, which I've never had since starting my company. So you talk about the quality of the hour. I mean, I would challenge those 5% who raised their hands, who said I had four hours of uninterrupted quality work time, because man, you could do a lot if you had that kind of time. So even the idea of 40 hours of, do what you need to do. No one's going to interrupt you. That is crazy. Your effectiveness must be through the roof at that point.

Jason:

Yeah. You actually should be tired at the end of eight hours, because you actually worked. And by the way, no one's literally working for eight hours. You're lucky if you get, let's be honest, like a good four hour day, really? Like, but if you get four uninterrupted hours, that's equivalent to like someone else working 10 hours and spreading their day across a bunch of different things. I mean like four hours is awesome. And for those who don't think eight hours is enough, just jump on a plane in Chicago and fly to London. That's eight hours, and just sit there, and you're going to see how long eight hours is. It's a lot of time. It's an extraordinary amount of time. And again, if you can get half of that uninterrupted and contiguous, you're going to see just how much time that is and how much you can actually literally get done.
So the people who work 10 or 12 hour days, or 14 hour days, the reason they're doing that is not because there's 14 hours of work to do in a day. It's because their time is spread across so many different things, and it's so fragmented that they can't really get into anything. And then the things they have to do, do require that kind of time, and they don't have the moments to do it, so they're just spread. But if you don't have to be spread and you can be condensed, you can get a whole lot of stuff done in a short period of time.

Chris:

Yeah. I just remember after reading your book, I had this thought. People are coming to my office asking me just the dumbest questions. Like, "What do you want to do about this?" And it was just like a building maintenance thing. I'm like, "You decide, you decide." So I had to send an email out to everybody and said, "I'd like to try something new. If someone else can answer it, please ask them. And if you feel like you can answer it, you should just do it. And don't worry if it doesn't work out okay, we can fix it if it doesn't turn out the way you think." and that made people much more accountable, it empowered them to make decisions on your behalf. And things were bumpy at the beginning, but things worked out much better.
And so I can just tell you, I was able to recapture some of my time because that's where I can actually contribute real value to the company versus, and it felt like this, and it probably was even worse, every 15 minutes something was popping up. So I couldn't get any work done until like 8:00 PM. And I know you're right about that.

Jason:

Yeah, and part of this too is, and I've suffered from this too, which is just like this ego, this sense that only I can answer that question, and so I need to be involved in all these answers. And I've consciously tried to step back over the past couple years and just let other people solve these problems. They always do, and oftentimes they're solved better than I could have. And even if they're equivalent, whatever, it doesn't even matter. I don't need to be involved in all these decisions. It's not good for the company. It's not good for me. It's not good for others. Let people use their own mind, let people use their own brain, solve their own problems. Of course, I'm here to help if necessary, and others are here to help too, but really trying to step off that.
And I think business owners sometimes have a really hard time letting go of feeling important, because sometimes there's not a lot for you to do during the day if everyone else is solving problems on their own. And so you feel like you need to get involved so you're still relevant or important, but really, you're important because you're not involved. You've created a place where people can solve their own problems. That's a really valuable way to build a business. It shouldn't just depend on you. And I think it's hard sometimes for people to realize that the business may not depend on them anymore. That's actually I think the enlightened state, the place you want to get it to is when you could potentially walk away, and everything would be okay. That's where you want to get, even though it might feel scary to get there.

Chris:

You had mentioned that you have these things where you do like a random thing where you pair people up to talk. Aside from that, what do you do to still feel connected to your team? Because I'll admit this right now, during the last two years, there's some people where I didn't even have asynchronous conversation with, and I haven't had one with them for like six months at a time.

Jason:

Yeah. Well, it's hard. So we used to, even when we work remotely, because we've always pretty much remotely, we would always see each other at least twice a year. So we'd fly everybody into Chicago, when we actually had an office in Chicago, from all over the world and spend two weeks a year together. We did one in the spring, usually one in the fall, and that felt like enough face time, even though it was only two weeks, but it was enough high intensity social face time to see everyone, to hang out with everyone, to share a meal, to share a smile, to goof around, that kind of stuff. That was good. And we haven't been able to do that for a couple years.
We're actually doing our first one in Miami next month. We're doing it in Miami because it's a good place for people from Europe to get to, and a good place for people in the us to get to, so it's kind of a nice central location around the world. Of course. So we have people in Hong Kong and Australia as well. So that's always going to be for far, right. But we're doing it. So we're very much looking forward to that. It's been a long time since we've seen each other.
I'm very intimately involved with building the products that we build, so I work with a lot of people on a daily basis, but I don't work with everybody. And as we begin to layer in a little bit more leadership, I'm working with fewer people actually, because other people are now running groups. For example, like customer service used to report to me, and now they report to our COO, Elaine, who just started. So they're reporting to her, not to me anymore. So I don't talk to Chase who runs customer service as often, and that's kind of weird because I'm pulling back from some of those interactions.
So I need to make a conscious effort to reach out to people and just say, "Hey, I'd love to catch up and just chat," or something like that. So that's something I think is on you, is on me to do. To reach out, and to be available, and to be present, and just to catch up with people. So there's that. There's also, we've also instituted some, even though we don't have a lot of meetings in the company, we do have a couple team calls a week. So we have a design team call Tuesday mornings, and a product team call on Thursday mornings. They're one hour, and the whole team gets together, and there's no real agenda. We just kind of talk. Maybe something comes up that we're working on, maybe not. And that's been really helpful. That again, doesn't cover the whole company, but it covers more of the company than just the people I work directly with.
So I'm involved in some of those. But yeah, I think ultimately if you want to interact with people across the company, you have to get out there and do it. It's unlikely that people will come to you just because of the inherent power dynamics of an organization. It's just awkward sometimes for someone to go to the owner of the business and say, "Hey, can we just chat?" So you have to do that. You as the owner or as the CEO or president or VP or whatever, you have to make that happen. So I think it's on you to do that.

Chris:

The not so serious question I have for you, and then please feel free to answer this in any which way you want, is I have the three books in front of me. Rework, Remote, and It Doesn't Have to be Crazy at Work. And I notice something, because I love the way that you distill information. There are themes, chapters, short bite sized pieces. I can understand it. And what I really love too, and have to just say this, is the illustrations that go along with it. Now I notice something. You have a different illustrator. So the first two books, I think it was the guy, where is it? I wrote it down here somewhere. Mike Rhode who illustrated, and I just, A, I wanted to know your creative process for how you work with an illustrator and why you decided to work with Jason Zimdars for the third book.

Jason:

Yeah. Great question. So Mike is awesome. We love Mike so much. So for the first two books, there was actually less, that's funny, there was less text in the books, and our publisher required books to be a certain thickness essentially, a certain number of pages. Because the old school notion is that if it's not this thick, you can't charge, you know?

Chris:

Right.

Jason:

You've been through it, right? So you get that. So this newer book, we actually had a lot more to say, and so we needed a fewer illustrations, and we also just wanted to change it up. So we have like, I think there's maybe a dozen illustrations in this book. We used to, I don't know exactly the number and it doesn't have to be crazy work. The other books would have an illustration per essay.

Chris:

Yeah.

Jason:

And this just has a few scattered throughout, and Jason Zimdars works for us. He's one of our designers.

Chris:

Okay.

Jason:

And I discovered that, I didn't know this when I hired him, but he's this wildly talented illustrator also. And so we thought it would be fun, since we didn't need as many this time, that we would do this in house. And so we just did that. Nothing against Mike. Mike is a genius, and one of the best illustrators we've ever worked with, and a truly honorable, great guy. But this time we just went in a different direction.

Chris:

I see.

Jason:

But yeah. Yeah. But I would say, if anyone wants to hire an illustrator, hire Mike. He's exceptionally good at what he does, and he does these sketch notes. He's just super, super good at that.

Chris:

He's really good at translating the idea into a -succinct illustration that captures the essence of it, which is a skill. It definitely is a skill and an art form.

Jason:

It is.

Chris:

I'm sorry. I have one quick follow up with you, because you mentioned, there is an illustration that accompanied each essay. So I'm just trying to like now as an aspiring writer myself. Are you writing these essays in real time? Like right now, and then you go back and you put them together and that's how the book gets made?

Jason:

Yeah. So our books historically have been written without knowing we're writing a book.

Chris:

Okay.

Jason:

So we're posting blog posts, just sharing ideas broadly. And then enough of them sort of congeal into this thing. Like, "Oh, maybe there's a book here." And so we'll kind of go back through the last few years worth of posts, and ideas, and some stuff we've just posted internally, not externally, and we'll begin to compile this stuff. But I'll write some of them and David will write some of them, and we have very different voices, the way we write, different styles and our styles have diverged even more over the years. So we'll pull this stuff together and rewrite it all, and then add new stuff, and have a unified voice. So typically I'll take the first stab at a lot of these essays, and then he'll come through and add his version of those essays.
And we'll do this all on Basecamp, and we'll go back and forth, and back and forth, and back and forth until we feel like we settle on something that we like, and we'll move on to the next one. Sometimes he'll take a stab a few first ones, but we found that it's better for us to initially start with one writer to establish a baseline voice, have the other writer come in and color that in basically. And also add more detail, and edit, and pull stuff out. And then we revolve, we start to orbit around this group of writing, and then we kind of pull it together.
We do write some original essays for the books, but a lot of them are based, I would say 80% of them are probably from previous things we've written. So this next book that we've talked about that we may or may not do will be based on the things we've been writing over the next few years, without knowing that we're writing a book, but eventually have enough material where there's something new. However, maybe this next time we'll do it differently. I don't know, maybe because we're doing everything differently. Maybe we'll sit down and actually write a book from scratch, but I find that to be an incredibly intimidating process. So I'm not good at things that are incredibly intimidating.

Chris:

Well, you've been super consistent so far, even though now you might want to be inconsistent with your consistency, in that you talk about this in Rework about go for small victories versus the big gamble. Instead of doing one 12 week project, make 12 one week projects, and writing a book in small moments at a time, I think make it a lot more like I could do this. I believe I can do this. And you know, at some point it builds enough momentum where you can actually get through it and finish a book.

Jason:

Yeah. The other thing we talked about doing would be to go back to Rework, and Doesn't Have to be Crazy at Work, and actually it'd be neat to have the original essay. This is more of a conceptual, like art project book, have the original essay, and then the new essay five years later. Do we still agree with this? Do we not? What would we change about this? Why do we change it? So if we need to have sort of a look back of a before and after, or before and present, I should say, version of some of these things. I don't know what we're going to do, but there's a neat idea in there somewhere.

Chris:

That is really cool. It's very kind of today because it's like the duet on TikTok, where you have the original and then your response to that. And sometimes it's just a reaction, and the reaction is really interesting, and they're not even adding that much, but seeing those two juxtapose together is really cool.

Jason:

Yeah. Like there's some stuff I've read that we wrote, I don't remember exactly which essays it was, but I read them back today and I go, "Eh, not so much, I'm not sure I agree with that anymore." And you should change your mind.

Chris:

Right?

Jason:

I mean, how can you grow up and not change your mind? So I think it'd be fun to admit like the changes we've made, and why we've made them, and how they may have been appropriate then, but they're not now, or there's a new context or a new point of view that we have or a new belief or whatever. Or it's not even that we were wrong about something before. It's just like things have changed. Times have changed. We have changed. Here's where we are today. That could be a fun thing. Maybe that's an online thing. Maybe it's not, maybe it's too conceptual as a book. I don't really know, but it'd be fun to revisit some of that stuff.

Chris:

You could definitely do that as a video project. You could read the passage, and you could split and you say, "Well, not so much anymore." And then tell us what you think now. That'd be a really cool thing to see.

Jason:

That's creative. I love that. That'd be a fun... It's so funny, so when I hear that I go, "Oh, that's hard. That's going to be hard." And then I immediately talk myself out of it, but it's such a good, clever idea that I just, I hate sometimes that I talk myself out of things that are going to be hard to do. I'm like, think about all the production I have to do. And it split, it's like, ah. It's like, is there a simpler version of that? This is always what comes to me. And then maybe sometimes there isn't, and like your idea that you just shared is the right way to do that. And we should.
So maybe the best way to approach this as a project is, I just do it once. Let's take one essay. How can I just do that with one? Versus the intimidating factor of like the whole book before and after, it's like, ugh, I can never do that. But how do we break it down into one thing and see if it's actually enjoyable or valuable? So that's kind of the way I would approach that, but I love the idea. It's a great one.

Chris:

Well, I'm looking forward to seeing you on TikTok. I noticed that you were on Clubhouse for a minute, and I was listening to you, and I enjoyed that. Are you planning on making more media?

Jason:

So I would do these things on Twitter for a while called Ask JF, which were these, Twitter has this really wonderful app called Twitter VIT, very important tweeters, I guess, or twitterers or whatever they would call it. And it's only available to some people, I got on the list somehow, and it's a Q&A app where people can tag you or something like Ask JF. And then in this Twitter VIT app, I get a list of all the questions, you can respond with videos. So I was doing these Q&A things because I really like live Q&A spontaneous stuff. And my friend's like, "You should be doing this on TikTok." And I'm like, "Eh, maybe. Maybe, yeah. Maybe I should." I'd like to do more Q&A's, but the TikTok workflow is not as clean as the Twitter workflow, but I've kind of soured on Twitter as a platform.
I don't feel good when I go there. It makes me, I feel like I'm walking into a stadium where everyone's yelling at each other. And even if like I have headphones on where I can't hear the yelling for a moment, I just don't want to be in there. So TikTok could be a good place, because I would like to do more video. I'd like to do more Q&A, I'd like to do more interactive stuff. I'd also like to do more live streaming. I was doing some of that for a while. Got sidetracked, but I'd like to. I think we've fallen off there, and we should probably pick that back up. Something I'd like to get into some more. So yeah.

Chris:

Well, I've enjoyed the bits that I've been able to catch live, so I encourage you to do it.

Jason:

Thank you.

Chris:

And not that you need my help, but if there's anything you need help with in terms of the video part, I'd be happy to help you.

Jason:

Let's talk about that.

Chris:

Okay.

Jason:

Because yeah, let's just catch up about that separately. That'd be a fun project.

Chris:

Well, Jason, I know that time is very precious for you, and you've given me more than one hour chunk of your time, and I'm just honored and thrilled to have this conversation. I can't wait to share this with our audience. I just genuinely just really appreciate you, man.

Jason:

Well, thank you, me too. And this, it's hard to imagine a better way to spend an hour and 15 minutes than to chat with you about these topics. And I hope this is useful for your audience, and as I've mentioned, I really, really love what you're doing and it's been great to finally meet you and chat. So thanks for having me on.

Chris:

Thank you so much.

Jason:

Yeah.

Chris:

If people want to find out more about you, where do they go?

Jason:

Well, it's funny. I would say Twitter normally, but I'm not really there as much.

Chris:

You just went on an anti-Twitter rant.

Jason:

But if you go to world.HEY, H-E-Y.com/Jason. So world.hey.com/Jason, J-A-S-O-N. That's where I'm doing a lot of my publishing these days. And you could sign up for my newsletter there, and I write something once a week, maybe, so you won't get slammed. So there's there. LinkedIn, I'm doing a little bit more writing too. LinkedIn feels like bit more of a positive place these days.

Chris:

Yeah.

Jason:

It's actually interesting. LinkedIn feels like it's having a bit of a resurgence, I think because so much of social media is quite negative. LinkedIn doesn't have that. It doesn't seem to have that. It seems to be a pretty positive place, so I'm enjoying there. So you can find me on LinkedIn and then, check us out. Basecamp.com. HEY.com. And I will tell you this, keep an eye on 37signals.com as well.

Chris:

Are they coming back?

Jason:

Let's just say maybe. Yeah. Yeah.

Chris:

Okay.

Jason:

We'll talk about that again another time, I say, but yeah. So 37signals.com is something to keep an eye on. You'll be watching it for a while and nothing will be happening, but at some point, something's going to happen there.

Chris:

I like that. We'll end with the tease and to be continued. It's a cliff hanger.

Jason:

Yes. To be continued.

Chris:

Perfect way to the episode, Jason. Thank you so much.

Jason:

Thanks Chris. Hey, this is Jason Fried, and you're listening to the Future.

Greg Gunn:

Thanks for joining us this time. If you haven't already, subscribe to our show on your favorite podcasting app and get a new insightful episode from us every week. The Future podcast is hosted by Chris Do and produced by me, Greg Gunn. Thank you to Anthony Barrow for editing and mixing this episode, and thank you to Adam Sandborn for our intro music.
If you enjoyed this episode, then do us a favor by reading and reviewing our show on Apple podcasts. It'll help us grow the show and make future episodes that much better. Have a question for Chris or me, head over to thefuture.com/heyChris, and ask away. We read every submission and we just might answer yours in a later episode. If you'd like to support the show and invest in yourself while you're at it, visit thefuture.com. You'll find video courses, digital products, and a bunch of helpful resources about design and creative business. Thanks again for listening, and we'll see you next time.

More episodes like this