Shane Parrish: Jason, I’m so glad to get to talk to you today.
Jason Fried: Likewise.
Shane: Huge fan of Basecamp, huge fan of yours, and you take a very different approach to things—which we’re going to dive into on this podcast, but I really want to start with something closer to the heart. What’s one of the biggest lessons that you learned from your parents growing up?
Jason: A number of them, but I would say, “Always figure out what the right thing to do is in any given situation. It’s not always that you’re going to do the right thing, but know what the right thing is.” I think that’s something that I’ve always taken away from my folks. My folks—I’ve always seen them do the right thing even when it’s inconvenient. And I think that that’s something that’s really stuck with me. But again, we don’t all live by that all the time, but we try, we try. So I’m always looking for like, “Hey, it’d be really nice if I didn’t have to do this, but really the right thing to do is to do this.” Or in a situation where you see something where it’d be more convenient to look away, but like the right thing to do is to stop and help, that kind of thing.
Shane: Do any examples come to mind, either through running Basecamp or growing, up that you witnessed your parents do that?
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Jason: I saw it a lot. So growing up, I had a friend named Freddy and Freddy’s family didn’t have a lot of money. My family was okay, we were doing pretty good. And Freddy and I used to play basketball outside. We had a basketball hoop outside on our driveway. And it came time to play basketball, to try out for basketball in junior high or whatever it was. Actually, this was not even a tryout, this is just like a junior high basketball team thing. And Freddy couldn’t afford to—it was like 100 bucks or something and he couldn’t afford to do it. And I remember my dad just taking care of that for him because it was the right thing to do. Freddy loved basketball, we used to play all the time and it’d be, you could say, well his parents didn’t want to do it or couldn’t afford it, oh well. But my dad’s like, “That’s just not right, he wants to play. It’s not his fault, the kid’s 15 or whatever, if we can help him out, let’s help him out.”
So that’s like a one example and that’s a monetary example, but it wasn’t really the money so much. It was the thought and it was the recognition in the situation that this kid wanted to do something and he’s being held back because his folks couldn’t afford it. And we can, so let’s help. I think that was like one specific example I can think of.
Shane: That’s an awesome example. Is that like the impetus behind Basecamp and working shorter hours too, where it’s trying to do the right thing versus what the easy thing is.
Jason: I think it’s doing the enough thing.
Shane: So talk to me a bit about that. This is counterintuitive, right? Because we live in this cultural pressure, whether it’s tangible or we just know it exists, and it’s to work harder, to work longer. You’re on a treadmill, and there’s like nine people waiting to take your job. And if you’re not working hard, then somebody else will.
Jason: Perhaps. We haven’t created a situation—or we made sure that we’ve created an environment where that’s not the case, where it’s not about, people aren’t looking around and say, “Who’s working the hardest?” And as I wrote actually in a blog post about this, like, “Look, we’re making software, this isn’t hard work, really.” Hard work to me is manual labor, something your back is sore by the end of the day, you’re really, really beat up. We’re fortunate to be able to do the things that we’re doing here, where we get to sit in an air conditioned room, we get to work on the computer. There’s very little risk involved with all this stuff. I tend to reserve the word hard work for really physical hard work.
But that’s just maybe inside. But we don’t look at it that way. We look essentially at output which is, “Is the work getting done?” If the work gets done in five hours a day then that’s enough. And frankly, you shouldn’t need 10, 12-plus hours a day to get enough good work done. The reason why a lot of people are working those longer hours is not because there’s 12 hours of work to do, it’s because they can’t find time within those 12 hours to actually get a few contiguous hours of time to actually do the work they need to do. So their work is spread across so many different things in so many different places in a given day, that they can’t piece it together in a relatively short period of time. So it’s spread out. Tthat’s why people are working longer, it’s not that there’s more work to do.
Shane: I totally agree. When I worked for the government, one of my observations was that, I was actually only working two hours a day like everybody else. Everything else is meetings, it’s context shifting, it’s nonproductive time, it’s constant interruptions…and it really disrupts not only your flow but the quality of your work.
Jason: Absolutely. And there’s more and more research coming out on this, and studies on this, and books about this and people paying more attention to it. And we’ve always tried to create an environment here at Basecamp where everybody gets a full eight hours a day to themselves basically. Everyone’s day is their own day, and how they spend it is up to them. And if someone wants some of your time, they have to ask you for it. For example, we don’t have shared calendars at Basecamp, so I can’t see anyone else’s schedule and they can’t see mine. I can’t take their time and they can’t take mine. If they want some of mine or I want some of theirs, we have to ask each other for it, physically ask like, “Hey Jason, are you free?” Or “Hey Jonas, are you free?” Or, “Hey Ann, are you free at three o’clock for 20 minutes to talk about something?” And she could say yes or no or whatever, but it’s a negotiation because it’s valuable. Time is very valuable and so you negotiate.
And versus a calendaring system where you click an empty box, and you basically send an invitation through a system—and it’s very rare that people decline invitations, unless they truly can’t make it—but the spirit is someone asks for my time, so I’ll give it to them even though…. But it’s this inhumane system that’s doing it. So we just want to make sure that people are talking to each other if they need each other’s time because time is incredibly valuable and to ask for someone else’s time, you should have a good reason for it. It shouldn’t be just something you can fill into a field in a form.
Shane: Can we geek out on that a little bit? Talk to me a little bit more about the internals of how Basecamp is run, how things are allocated, how teams come together, what the process is like on the inside, what does that look like? And how many people are you now? Just to start out with that.
Jason: Sure. We’ve 55 people on the company. And different teams work slightly different ways. So I’ll talk about product development, which is primarily my responsibility. I guess everything’s my responsibility, I run the place, but that’s where I spend most of my time. On product development, we basically choose work to do every six weeks, and we do work over a six-week period of time. And I can get into how we choose that, but let me set the framework here. Set what we call six-week cycles, and during those six weeks, we pick off three to five-ish projects, and each cycle of six weeks, there’s usually two to three different product teams working on the features we’ve decided to work on. And those teams are three people or less. Oftentimes it’s two people. And we basically decide that there’s—six weeks is enough time.
A big fundamental thing about Basecamp is this idea of enough, and I’ve already talked about that like enough time during the day. And six weeks is enough time to make substantial progress on something that’s important. And it also forces us to make sure that we understand exactly what it is that is important in any feature that we’re building. Because if you give it three months, it’ll take three months, we give it six months, it’ll take six months. And the exciting thing to me is to figure out what’s the six-week version of this idea, and then we can really boil it down into its essence.
So, we pick work every six weeks, assign it or throw it up for grabs to different product teams and they can decide who wants to work on it. And then they get to work. And these teams are autonomous. They’re not checking in with anybody automatically. They check in when they feel like they need to check in or they have questions or if I want to look at something, we’ll look at something. But they’re given the full responsibility to complete that work in that amount of time. And 90-plus percent of the time they do. And so that’s at a high level how we work on product.
How we come up with these ideas every six weeks is a different process. It’s typically three of us thinking about what we want to do next. We don’t have a road map, so we don’t have a…I don’t know what we’re going to do. Actually, I have no idea we’re going to do eight weeks from now. I just don’t know. Nobody knows. But as a cycle is coming to an end, maybe a few weeks before that, a few of us begin to get together and think about what do we think we should do next? And we start to think about the things that we wanted to do and things we should do, and how things are going currently, and new ideas that have come up through customer requests, and throw a bunch of stuff on the table.
And over the next few weeks we bat it around, think about it, sketch it out, write it up, play with it and figure out if we think there’s enough of an idea here that’s solid enough, that’s well-formed enough that we’re confident it can be done in six weeks, that we can then hand it off to a team, versus throwing a team ideas that are really barely baked and then they have to take a lot of their time to actually think them through, and then there’s not enough time actually to do the work. So before we hand work over to a team, we feel we’ve got it 90% of the way figured out, and then exactly how the team does it is up to them, but we can see a path to the end there.
Shane: And then [
Jason: I think I’ll stop there because maybe there’s a bunch of details to talk about.
Shane: No, no man, I want to geek out on this stuff.
Shane: This is really interesting, if you’re okay with that.
Jason: Of course.
Shane: How are the teams…so you give the autonomy to the teams, the two- or three-person teams. How is success or failure judged? And then in your mind, what is the difference between average and astonishing in terms of deliverables? What makes somebody above average? Maybe one of those teams versus average, and then what are the metrics that you…do you outline ‘this is what success looks like’ beforehand or is it like, “Hey, here’s an idea, it’s a little bit flushed out, go implement it.”
Jason: We’re different and that we don’t have any goals or any metrics for success. We have an idea for a feature, let’s say, or a way to improve the product. And because we use the product every day, we’re the number one customer of the product and because we know our customers who use the product. We have a pretty good sense at the end if it was an improvement or not. It’s not a matter of how many people use it, it’s not a matter of this is not used 18,000 times, but we’re aiming for 22,000 so it’s now a failure, or they were aiming for 17,000 unique uses a day or whatever and it’s 18, so it’s a huge success now. It’s like, how do we feel about how this turned out? How do we feel about how the project also went?
It’s not just about the output and outcome, it’s about how did it feel as we went? Are people burned out? Do people hate each other now who liked each other six weeks ago? Did this make our company stronger or weaker? Did this improve personal relationships or damage personal relationships? It’s a more holistic viewpoint—of outlook, I should say—on how this thing turned out. You could technically end up with a great feature that customers love, but it could have completely destroyed morale internally. To me that’s not a good outcome. It might be a good outcome on the customer’s side, but if you’re damaging your company internally, you can’t do that very long until it actually ends up really damaging things on the outside too. So we look at the whole thing, and this includes individuals too. So, for example, if somebody has been working on three really hard things in a row—essentially, I’m using the word hard here, but let’s just say like three challenging projects in a row—the next project might be, we might throw ‘em something that’s a lot simpler just so they can decompress a bit.
So I’m thinking about who’s been working on what? How have they been doing? What do the string of products they’ve been working on look like and where do I think that this next batch of work would fit in with them as a human? And so we look at things that way. We also do postmortems…or whatever. It’s always a weird word to use. But projects are done, we look back on them a few months later and just get a sense of after we have a little bit of distance, how do we feel about it, what do we think went right, what went wrong, what could we have done better? We do get feedback from customers, obviously, and so we incorporate some of that in the review as well. And then of course if there’s a glaring mistake, like a major, we made a major mistake, then we go back and fix it immediately. Otherwise we let it ride for a while and just revisit it a few months later and see how it all felt.
Shane: There’s two things I want to tease apart in that response. The first is you used the word “feel,” and I thought that was really interesting because we’re in this age of machine learning and algorithmic-driven insight. Can you talk to me a little bit or expand upon your thoughts around that?
Jason: I put a lot of value on feel and intuition and gut in these things. We’re not a data-driven company in terms of product development. We use data a lot for improving performance in terms of our infrastructure, making sure that we get back to customers in reasonable amount of time, which is currently about 10 minutes. If you email us, you’ll get a response in about 10 minutes. And we look at data though in those ways. But in terms of how does something feel to work on, how does it feel to develop it, to deliver it? How do we feel about it when it’s done? I think that it’s a difficult thing to measure with numbers.
Again, the problem is that..again, like I said, if you deliver a feature or product that hits it out of the park on certain metrics perhaps, but it damages the people who worked on it together—and that can easily happen, and happens a lot. Not here necessarily, but I hear about it, I read stories about it where like, “The product was great but man, three product managers quit along the way,” and someone else is like, “This is the last project I’m ever doing here,” and there’s shrapnel from these things and there’s the side effects. So if you’re only measuring the output and the outcome in terms of how customers felt about it, but you’re not really thinking about how people, actually humans felt about it, I think you’re missing a big picture. Now, of course, if you don’t really care about the people in the company and you’re like, “I’ll just replace them if they leave because there’s a million people knocking at the door who want jobs here,” you can do it that way. I don’t think that’s a really great way to run a company, but you can do it that way too, and then you maybe don’t care about the feel so much.
But we care a lot about how things feel here and how people feel about the work they’re doing and who they’re working with and how things went down. So yeah, we’re in a, maybe approaching a different age, in a sense, but I think the personal touch and the human touch and the understanding between people is a certain specific intangible that’s actually very valuable. Especially as a manager or someone who’s running a company, I think you have to understand how people feel on a day to day basis about a bunch of different things to figure out if you’re going the right direction.
Shane: What are some of the lessons that you’ve learned in the last decade running a business? But not only running a business, but running a business the way that you want to. You don’t seem like you’re very influenced by outside factors.
Jason: I try not to be, I try to be quite ignorant actually about the trends in the industry and who’s doing what and competitors and what their products are doing. I find that the more I pay attention to that, the less free I’m able to, or the less free my mind is, essentially, because you’re just colored by what everyone else is doing and then you don’t have as much space for your own thoughts, I think. So I’d just like to—I’m aware of what’s going on, but I don’t like to look at those things in detail. I much prefer to pay attention to things outside my industry. I take a lot of inspiration from architecture, from art, from nature, from going on long walks, like that kind of stuff, versus looking at the hottest new app, or the new collaborations thing that just came out or whatever. I think you’re much better off looking broadly, looking outside of your own walls, than looking too close at the things that are really close to you.
So to me, I’ve always tried to run things in a way that makes sense to me, and hopefully there’s enough people around here who it also will make sense to. And hopefully there’s enough customers out there who it also makes sense to. We’ve never been a company that’s interested in dominating in the industry or taking market share from anybody, or trying to have millions and millions of customers. We only need to find a small number, technically, of customers who really believe in what we’re doing and we see the world the same way, and we found many of them. Over a hundred thousand people pay us for Basecamp every month, so it’s a great business. But a lot of people would look at that and go, “That’s not enough. You need millions of customers.” And you say, “Well, you do if your costs are out of control and you have thousands and thousands of people.” But we have 55 people, so we can build a really wonderful business with a lot of impact doing it our way without having to pay attention to what everyone else is doing.
Shane: I like that a lot. It sounds a lot like one of your investors. When you were saying that, it sounds like Jeff Bezos a little bit. Well, he doesn’t seem overly focused on what other people are doing, he seems to be doing his own thing, but generally aware of things. And he’s an investor with you guys, correct?
Jason: Yeah, kind of. So he owns a piece of Basecamp. He bought those shares from David and I, so he never invested in Basecamp the company, essentially. His money was never put in the business to run the business. For 20 years as long as we’ve been in business, we’ve always been 100% funded by customer revenues.
Jason: But he did buy a piece, we did sell him a piece of the business in 2006. He’s been someone who’s forever publicly been interested in being misunderstood. And I’ve always admired that about him, which is, he’s just going to do it his own way, and he has different ideas in the rest than the industry and I’m sure he pays attention to things and sometimes he does—he will follow the industry and other times he’ll create a new industry. But I don’t think he’s overly concerned with what other people think about how he approaches his business. We have definitely a very different perspective on how to run a business. We’re going to keep our business as small as possible. He wants to build the biggest business in the world. He’s the richest man in the world, I am not. So we’re very—
Shane: Not yet.
Jason: Never will be, but different points of view, and never would want to be either, by the way. But different points of view on how to treat people and run businesses and whatever. But fundamentally, yeah, I think we share that point of view, which is, just because other people are doing it this way does not mean that that’s how you should do it.
Shane: Who are some of the people that you admire that are running businesses that you maybe don’t look to for inspiration, but keep tabs on and then why?
Jason: Well, I admire anybody who stays in business for, let’s say more than five years. For example, a friend of mine runs a small grocery store down the street from where I live and I admire him because he has something we don’t have, which is that he gets to know every one of his customers by name. I can’t know 100,000 customers by name. But when people walk into his shop, he knows who they are. Or he could get to know them, and he gets to know their preferences and he gets to know them and he gets to know their family, and he can say, “Hey Jim, hey Bill, hey Sally, whatever,” and that’s something I think is really cool.
He can also experiment much faster. It’s funny you think in technology, you can experiment really quickly with A/B tests and stuff, but he can experiment even faster. He can just put something on the counter where you check out, and see if it sells faster than it did when it was on the shelf. He can play around, I think, in the physical world a lot better, a lot faster in fact than the technical world. And you can also pick up on things. You can see things you can’t necessarily see in the technical world. We all, again, think there’s so much data available to us as far as customer preferences and whatnot, but I’d say very few things beat just paying attention, just looking and picking up all the subtle nuances of how someone picks something up and looks at it. Do they turn it around, do they hold it, do they—why do they put it down? How long do they think about it? All those things.
So I used to work in a grocery store when I was growing up, and I used to work in the produce section, and I used to love to watch how people would choose fruit and vegetables. Some people take a cantaloupe and they knock it and they listen to it. Some people smell a cantaloupe. Some people look at the colors of the cantaloupe. I don’t know what the right way is, but I was always fascinated just to watch people make their own decisions about, why this one? And I think he has that. So I love that.
There’s a shop down the street also from me, that sewing machine repair shop. It’s been in business for 80 years, which just blows my mind. Then there’s technical businesses that I pay attention to. I really admire what Stripe is doing and how they’re doing it. And then there’s people like Charlie Munger who have—who I don’t know, but who I admire greatly for his clarity of thought, his steadfast commitment to value and to being straightforward and common sense and in all that stuff. So I take inspiration from a whole bunch of different people.
A good friend of mine runs a gym, personal trainer. He’s down the street from me, and it’s just him. And I’m jealous of the fact that he gets to run a business and it’s just him. I love my employees, but it’s kind of nice not to have any too, to be honest, right? If I was being honest about business, it’s like, it’s nice to truly do your own thing your own way, and so I really admire that too. But of course at the same time, if he’s sick, he’s out of business for three or four days. I don’t admire that. So of course having employees and having a process and a company, there’s huge value in that too.
But I just like to look at all different businesses. But as long as you’re staying in business and you’re making more money than you spend, I respect you. I have a hard time though, sometimes, with tech businesses that are, quote, “successful,” or held up as successful examples of businesses, that are actually fundamentally terrible businesses. I think companies like—Uber is an example, of course they had some…maybe some more moral issues perhaps too, but for a while at least—I think they continue to lose billions of dollars.
Shane: Talk to me a little bit about that, just in the sense of—so you’ve been effectively bootstrap from cash flow since day one. How do you feel about competing against people that seemingly can take unlimited losses because they’re funded by people willing to gamble a lot of money on an ultimate outcome?
Jason: I don’t care basically because their performance or their lack of performance or their success doesn’t really necessarily affect mine. And the fact that…like I said earlier, I only need some customers. They need all customers, and so they can take as much as they want and there’s probably going to be plenty enough left over for me anyway. And not only that—at some point, they will go away. One of the great ways to, quote, “win” in business is to just to stick around. And the best way I found stick around is to be profitable, because if you’re profitable, you get to stick around as long as you want.
Of course, that’s not to say that we couldn’t be beat one day or something could go catastrophically wrong. Of course, every business dies. Every single one of ‘em dies. Often they kill themselves though. They don’t change, they don’t do something right, they don’t pay attention to customers, they get cocky, they get greedy, whatever it might be. It’s usually those things. It’s not the competitor has more money than you and outspends you. It might be true in a specific market where it is really winner take all, but I don’t think it is in our industry and that’s why there’s hundreds of companies roughly doing similar things that we’re doing. And many of them are going to do quite well and some of them won’t. But it’s not that there’s no customers left to take. It’s not that, it’s just that some people’s products don’t fit the market or some people’s prices don’t fit the market or they give things away for free and they run out of money because they can’t pay their employees, or whatever it might be.
So I’ve never looked at how much money someone has raised as a thing to be afraid of, or anything like that. In fact, I always think like, “Man, I don’t envy you the position you’re in. You’ve raised 50 million dollars. The expectations on your shoulders are enormous.” There are no expectations on my shoulders, other than to continue to develop a good product and take care of our customers and take care of our employees. But those are expectations I can manage, versus a billionaire who put a bunch of money into your company who wants to make more billions off of you and you’re on a certain schedule of growth that has to be sharply up and to the right, otherwise, you’re not going to be fulfilling the investment requirements and criteria and therefore they could choose to push you out or take you public when you’re not ready or sell the company when you don’t want to.
I would never, ever want to have those expectations on my shoulders. So I don’t envy those companies and I’d much rather be in my position. I would frankly, honestly not trade my position with anyone else in the world as far as anyone else running a company.
Shane: What are your expectations of yourself?
Jason: I just want to do the right thing and do the best work I can on balance. Not every day is going to be that day, and not every decision I make is going to be the right one. I’m going to make mistakes and screw some stuff up, whatever. But on balance, I want to make sure that I’m trying to do the right thing as often as I possibly can, and making sure that I create an environment where other people who work here can do the best work of their careers. I think if someone decides to work here, they’re saying no to a million other opportunities. And so I feel like I have to respect that and to create a place where they can do their best work because that’s their career. They should be able to do their best work and flex their muscles as best they can and flex their mind as best they can.
And part of that again is getting back to the point where I want to make sure everyone has a full amount of time to themselves to do their best work, and I also want to be supportive and provide enough autonomy and all those things. So those are the expectations I have for myself, but I don’t have expectations around growth, I don’t have personal goals. I don’t want to be seen in a certain way, I don’t need to be in the media, I don’t have that kind of stuff. I also don’t have any interest or desire to change the world or anything like that. I just want to make a good product. I want to work with great people. I want to be intellectually challenged. I want to be able to put my ideas out there and see if they stick or not. And then also of course have a good life outside of that, certainly family and the whole thing, so that’s kind of it for me.
Shane: That’s a really sound philosophy.
Jason: Hope so. Because it’s what I’ve got, so I hope it’s sound.
Shane: But it’s less common than you would want, right? Maybe, or less common than…. I would like to believe the sort of people—you seem to have a very inner scorecard and take a lot of satisfaction out of just doing good work and craftsmanship and it hearkens to a different era, almost, than the one that we’re in.
Jason: I try to just understand what enough is. And I’ve told this story before, but I think it’s a good one to bring up here, which is, I remember I used to run a lot outside. I ran track and stuff, and after college I wasn’t good enough to go to the Olympics, right? Not anywhere close to good enough. But I’ve always enjoyed running. And I remember trying to run a certain time, I don’t know what, a six-minute mile or whatever it was at the time. Because I was more of a sprinter, I was never a good long distance runner. Anyway, I remember going to run and not getting that, and I remember feeling like I was disappointed. I ran a 6:10 instead of a 6:00. And then you think about, like, “Why would I be disappointed with that?”
Quite different questions like, “Did I enjoy the run?” Yes. “Did I get fresh air?” Yes. “Did I feel like I worked my body, my heart, my mind?” Yes. “Did I see things as I ran that I was excited about?” Yes. “Did I get to breathe some fresh air?” Yes. How are any of these outcomes negative?” But if you measure yourself against a number or a goal, like six minutes and you don’t hit that, then you can feel disappointed or you feel like I got to work harder next time, but why do you actually have to work harder next time? What was wrong with this time? And I just came to these conclusions and I continue to come to these conclusions.
In business, there was a time when we tried to set some goals like, can we hit this number? And we started doing things that weren’t us. We started advertising—we don’t advertise. We started buying ads on Facebook, to try to move the needle. And we felt like, “You know what, we don’t like Facebook. I don’t like their company. Why are we giving them money? So we can hit some number that we made up? Why, why, why again, why we don’t have to do this.” And we just realized, we were going for something that we thought we were supposed to do and try to do and whatever.
And we eventually realized we don’t need to do this. We stopped doing it and everything’s just fine still. So I just think that my experience with setting goals and hitting numbers and hitting targets—you either do it and then you set another one, so it’s like it’s never ending quest to keep setting numbers, or you don’t do it, you’re disappointed. How about just not doing it at all? And just doing the best you can. I’m going to try and do the best work I can every day regardless of if there’s a target or not. If you need a target to do your best work, it feels a bit artificial to me. That is me.
Shane: I don’t think it’s just you. I have a couple of friends who run fairly large software companies and it’s really interesting for me to watch their psyche year over year ,and it’s a constant state of failure. And then the moment where they hit an objective, usually a revenue target or something, it lasts for like a day and then it’s always like, “Oh, well next year we have to do 30% more.” This perpetual state of stress and you can see it in terms of how they age and how they feel about themselves, and their self-talk changes and it’s just a really interesting way to live, right? Where you’re perpetually not achieving something that you’ve convinced yourself perhaps that you want to achieve, but maybe wrongly.
Jason: Well, yeah, I see it. And our industry is sick with that, I think. Primarily I would guess because it’s a high growth industry, first of all. So, there’s this expectation you’re supposed to live up to, and when you look at all the, let’s say the great companies in the industry that people consider great on the outside, they’re all growing rapidly, so you want to be one of those. So, you aim for that. There’s also investor pressure. I don’t know if these folks that you know have taken outside investment but if they have, then they have to deliver. They have to deliver for someone else. They’re not really delivering for themselves. You could say they are in some respects, because maybe one day they’ll make a lot of money off the deal or whatever, fine. That’s totally cool. But for the most part, you’re trying to deliver on this for someone else.
For me it’s just not a satisfying way to go through life. I don’t think that aiming for things is really like…. We aim to do a good job. Because that’s like the satisfaction of putting in a good day’s work, and then you line up a bunch of good days in a row and then you have something there, and you’re excited about the work, and sometimes you think you’re really onto something and you’re motivated by that. But that’s all intrinsic motivation. It’s not some number, some target you’re supposed to hit for someone else for some other reason. I’ve never been driven by that, really. I don’t think it’s really healthy. And I do see a lot of people who, if they were to take a step back and look at what they actually have, they should be really proud of it. But instead they’re disappointed because they—they’re disappointed or like, always teetering on disappointment because they’re setting these really difficult targets to hit. And it’s like, “Why are you being so hard on yourself?” I don’t see the reason for it.
Shane: Right. I don’t think a lot of those people look back favorably on this period of life. It’s like Ebenezer Scrooge, right? You want to be the most successful, widely known person, and then you get what you want, but then at the end of your life you just want a redo.
Jason: Yeah, that’s true. There’s certainly things I’ll want to redo in my life, I’m sure too. As you get to the end, you reflect and what not. You’re like, I should have spent more time here, or should have done this, or should have been nicer to this person or whatever it might be. Right. But I wouldn’t want to regret my career, that kind of thing—
Shane: Or how you treat people, your relationships.
Jason: Yeah, of course. And you’re going to do that for 40 years or 50 years of your life maybe? Something like that? I want to look back and I can go, “I did my best,” versus like, “I didn’t do well enough for someone else.” That’s not how I want to measure. By the way, I don’t even think of measuring. I don’t think I’ll look back on my career. I just don’t think I would actually look back on my career and evaluate it in that sense. How do I feel on a day to day basis is what I look at.
Shane: Switching gears a little bit here, how do you feed your brain? What books do you read? Do you read magazines? Do you just keep your eyes open to what’s around you? How do things crop up in there?
Jason: It depends. Right now…the last four years have been more challenging. We have two kids. We just had another baby a few months ago.
Jason: Thank you. I don’t have a lot of personal time at the moment. I go home at 5:30, family dinner, kid in bed at 7:00, kid gets up at 5:30, so I gotta go to bed by 8:30 or 9:00, so I’m not a complete waste. So I haven’t had a lot of free time lately. I do enjoy reading books, but because I don’t have as much time, I find that I’m listening to books more frequently because I find I can listen for 20 minutes in the car on the way to work, like audio books or podcasts or that sort of thing. So I’m consuming that. Oh, I hate that word. I don’t want to use the word consuming. Consuming content is like the worst thing I can imagine.
I listen and try to learn and pay attention to things that are interesting to me. So, mostly nonfiction stuff. I like autobiographies. I like learning about people. I like learning about history. I like nature. So I pay a lot of attention to that. And then there’s also things I’ll do, like I like to go on walks, I like to pay attention to nature. Like I said, pay attention to architecture and that stuff. And so in any given experience, I’m trying just to look around and pay attention to the details of how something came together and why it is the way it is. And so it’s that perpetual low-grade paying attention. And then when I have those moments of downtime or whatever, I’ll listen to something or read something occasionally. I wish I had more time to dig into a number of books. And hopefully in a few years I’ll have a little bit more of that. But right now it’s been a little bit challenging.
Shane: Are you like a 1x audio guy or are you 2x? How is that?
Jason: I’ve experimented with speeding things up and I’ve decided to come back to 1x. I used to be, I’ll do like one and a half or two, mostly on podcasts, sometimes on audio books. And it kind of depends. Some authors who read books, they seem like at 2x-speed it’s fine, for others it’s a little fast. The point was is that I’m like, “What am I rushing? Why am I trying to pack everything into my head?” There’s time to get to these things and if I don’t get to them, I don’t get to them. So I’ve gone back to 1x. I don’t think it’s necessarily a good thing to have information coming at you that fast because you’re in a hurry to get it. I think it kind of creates this expectation of everything coming at you fast, and I don’t think that’s necessarily that healthy either. So I’ve just gone back to one. I go, “It takes nine hours to listen to this book instead of five or whatever.” Like, “Oh well, that’s fine. I’ll get to it.” I could have saved five hours. But over the course of my life, like big deal. I’d rather just listen to the author’s actual voice and just take it at that speed.
Shane: It’s always interesting when I meet people who have listened to the podcast and they think my voice sounds weird because it’s not at 1.5 or 2x. I always find that interesting.
Jason: Yeah, I can imagine, like, training your mind to be able to listen even to 3x speeds or people down the road reading books at a different cadence or something to—but again, it all comes down to like, “What’s the rush?” Why do we need to pack all the stuff in? Is it because we don’t have enough time? That’s maybe okay then, maybe, maybe because there’s external circumstances, but still…if you just don’t get to everything in life, then you don’t get to everything in life. And by the way, that book you’re speeding up reading—you have enough time for that.
Jason: So anyway, that’s my current thing. I’ve gone back to 1x, but I had to experiment at least with faster reading.
Shane: What are things that you do that are maybe counterintuitive or not widely done amongst your peers, in terms of how you raise your kids or how you think about raising your kids?
Jason: I’ve decided not to ask people about parenting so much, because—I don’t know, it’s hard to evaluate, right? I don’t know how to compare. Basically, I’ll just—can I say like, for the most part we’ve with our four-year-old—our three-months-old can’t really do anything yet of course—our four-month…our four-year-old, sorry, I really believe in child-led learning. And he’s in a Montessori school. He really seems to enjoy that. We let him get into whatever he wants to get into. And I’m actually a fan of a book, I think it’s called The Self-Driven Child. And that’s our style, but it’s not for everybody and I don’t want to be preachy about it or anything like that. But for us it works pretty well.
Like our particular kid, he seems to want to go into a bunch of different things and we just let him go where he wants to go and let him play a lot. I’m not like someone who’s academically…I was never been, just…my English is not so good there. I’ve never been someone who’s been academically focused in terms of like, “It’s so important that you learn these things by these times and these topics or whatever.” So, I think it’s important for kids to play and to just explore and be creative and whatever. And if he gets into this or our daughter gets into that, whatever they get into is fine with me. I’m not into pushing anything on anybody.
Shane: I want to dive into this academic focus a little bit. Maybe with…I’m going to think a little bit out loud here, but it seems there’s increasingly a system whereby we’re driven to pass a test, to demonstrate knowledge, but that success is often pushed by parents as well, who view their success as a parent tied up to their child’s academic success. But it seems to be missing the broader point about what really makes for a successful life. I’m wondering, can you expand on that with some of your thoughts?
Jason: I’ve seen two groups of parents around that. There’s the parent who was very academically successful growing up, went maybe to an Ivy League school and feels their kid needs to do that too, because they—understandably, that’s how they went through life and they’ve been successful in terms of, someone’s a doctor now or someone is a lawyer now or someone’s a whatever now. So that’s their path. And I get that. And I’m bringing my path to the picture because I was basically a C student. And so I’m like, “It doesn’t really matter that much.” And that’s my perspective and not theirs and their perspective is not mine. There’s also of course a situation where someone’s parents maybe didn’t go to school ever. And they want their child to be educated, and to have a better life than they did. And then they see education is the path for that. And I totally get that too.
So there’s just different approaches. I think it’s more about…what I try, what I don’t want to do, I guess, is to apply unnecessary pressure. A thing like, “You have to be this way or you have to learn this thing, or you have to do this or else you won’t X, Y, Z.” I don’t like the “or else you won’t X, Y, Z “angle. Right? “And if you don’t go to school and don’t get good grades, you won’t X, Y, Z.” I don’t like that part of it. I think education is important. I think it’s important to be creative and to pay attention and to be curious and all those things. But, you can not enjoy school and be very smart. You can not enjoy school and do something new that no one’s done before.
School is a means to certain ends, but it’s not the means to any end. I just don’t want to apply that kind of pressure. I think what’s more important perhaps is just like seeing things through, knowing why you’re doing what you’re doing, finding the things that you’re really interested in and learning about those things, and building some self-awareness and knowing yourself, I think is maybe the most important lesson ultimately, which is of course a lifelong lesson because your self changes over time.
If I was to maybe encourage or instill something in our kids, hopefully it would be like, find your path, figure out what you like, find out what drives you, what you’re really curious about and go into that and there’s a lot of depth in anything. So I think that’s my take on it. And I think as far as, by the way, getting to original point about parents wanting to see their kids do something to make the parent feel better, I think we all do that in one way or another. It’s a matter of pride in some cases. It’s a matter of maybe I didn’t do well in life but my kid can. And so that makes me feel better, that kind of stuff. So I wouldn’t criticize any of that. It’s just—
Shane: IN the end, there’s no judgment on my part at all.
Jason: No, me neither. But it’s more about at the end of the day, it’s just important, I think ,to understand why you are leading someone in a certain direction. I’m not sure that it’s always that well thought out.
Shane: What are some of the things that you see as the CEO out of the people coming out of school who might have good grades, but ultimately are ill positioned for success in the workforce, versus people who might have had mediocre—like both you and I were C students. I was a D student—so like different grades, but they’re well positioned for not only a long career but for much success, however they wanted to find that.
Jason: The thing that surprises me most about people coming out of school is how poorly school teaches people how to write, and communicate actually. I read cover letters and whatnot and I’m just surprised that you can graduate college and not really know how to explain yourself well, not really know how to get to the point, not really understand what it’s like to make your case, or to make a case, and that just surprises me. And I think it’s unfortunate and I don’t know if it’s a matter of writing not being taught properly, or the type of writing that’s being taught in school being very academic-based versus actually communication?
You write a lot of papers in school. You’re not really communicating to other people. You’re writing something to a teacher. Yeah, that’s another person. But it’s more about like trying to show your subject, your awareness or knowledge of a particular subject, versus trying to persuade a number of people to listen to what you have to say, or try to make a point or share an idea or put something in a certain light where people go, “Yeah, that’s a good idea. Let’s go that way.” You just don’t see a lot of that. So I’m surprised by that. I think, when I look at people and consider hiring people, looking at the writing is the first thing I actually look at. And then I look at just their general curiosity. You can look at it in different ways depending on the person and the role and stuff, but are they really curious about what they do or are they just trained in it?
Shane: How you tease that out?
Jason: Well in some cases, like if you’re a programmer, you could say—and this isn’t always the only way to do it—but someone might contribute to open source in their spare time because they just like that. But that’s not always fair because not everyone has time to do that and not everyone’s been exposed to that. But that’s one way. If someone’s into design, for example, one of our designers—a guy named Jonas—I remember when I was looking at his application, this is, I don’t know, seven years ago or whenever when we hired him, or however long it’s been. I was impressed because he was a tinkerer. He was a designer but just played with design in his projects that he showed. He had like a lot of personal products. They weren’t just client products, but personal projects and there were creative and interesting and abstract and experimental and that kind of stuff. I’m like, “This guy just likes to play with design and I like that.”
Another designer we hired—she’s not with us anymore—one of the things I liked about her is when we were looking at her work together, she would say, “I’m not so sure I like what I did here.” And to get the job, we were looking at her body of work, basically. And she’s like, “I don’t know if I like this that I made.” And I like that because that’s a certain sense of introspection and self-critique that I think is really valuable.
So there’s a curiosity there too. It’s not like, “Here’s my best work.” People put their best work forward and like, “This is my best work.” And she’s like, “This is good. But I don’t know I would have done it this way if I had another chance.” I liked that. So, it depends on the person and depends on the situation. But you can usually tell who has just work to throw on the table and say, “My work speaks for itself.” And other people who say like, “I just like to do this stuff.” And so I tend to gravitate towards the people who just like to do this stuff. Of course they have to be capable and they have to do great work also, but that they would do this anyway. I like that from somebody.
Shane: I like that a lot. You’ve written two books now. What did you learn from writing the first book, and then what was the need for the second book?
Jason: I’m assuming you’re referring to Rework and perhaps It Doesn’t Have to Be Crazy at Work?
Shane: Yeah, was there more books than that?
Jason: A couple of others also just, one called Remote.
Jason: That’s okay. No, totally fine. I just want to make sure I’m talking about the right thing for you. Remote, and then Getting Real was another book that we did a while back. But Rework and It Doesn’t Have To Be Crazy at Work are the two big books that we’ve written. Rework, which we wrote almost 10 years ago now, was a book that was about how we run our business at the highest levels: how we think about marketing, how we think about product development, how we think about hiring, how we think about the industry, how we think about press, all the—you could say it’s our cookbook. Essentially, it’s like these are our recipes on how we make our dish, so our business, essentially. And then It Doesn’t Have to Be Crazy at Work, which is our most recent book, is really more about pushing back hard on some current trends which we don’t think are very healthy, which is this idea of people working 80 hour weeks—
Shane: Always available.
Jason: Always available, instant everything. Everyone saying they’re super busy. Everyone’s super busy all the time. I’m not busy. I don’t want to be busy. But everyone’s super busy all the time. People working weekends, like whatever, and that it’s okay to respond to an email, a work email on Sunday at three o’clock. I don’t know if it’s actually okay to do that, but a lot of people do it. So pushing back hard on this trend of overwork the hustlemania like this, all this stuff that’s going on out there. We don’t run a company that way. We run what we call a calm company, C-A-L-M, calm company. We wanted to talk about how we do it. And it felt like this is the right time to do that because I feel like things are going really in the wrong direction quickly, actually. So it felt like the right time.
But we write books because we have something to say and there’s no reason to keep it to ourselves. A lot of businesses seem to be afraid to share. They think they have a special formula, a secret formula, and why tell everyone our internal and proprietary ways we work? It’s like whatever. I’ve always been inspired by chefs in this regard. So, great chefs will write cookbooks and they’re putting their recipes in a cookbook and they’re not afraid of someone taking that cookbook, reading all the recipes, and opening a restaurant next to them and putting them out of business. That’s just not how it works.
They want to share the recipes to get the word out about them. Maybe when someone comes to town and they tried their cookbook, and, “You know what? X, Y, Z has a restaurant in town and I’ll try his restaurant or her restaurant and try that because I really liked making the recipes.” And so for us our books, our recipes, that’s how we do things, how we think about things, and we don’t have a marketing budget. We don’t spend any money on advertising. So for us, the books in a sense are a way to get the word out about our points of view and our ideas, and indirectly they promote our company but we really do it just to share the ideas.
Shane: Two thoughts on the constant state of work these days. One, I was with my kids, I think it was a couple of weekends ago, and we were in a coffee shop and they were reading and I was just observing somebody next to me, quote-unquote “working.” And it was just a constant tab change, slash slack, slash—like it just, it looked from my point of view, and I wasn’t trying to read the screen or anything like that, I was just watching how other people work because it’s so rare that we get to see other people actually in their environment doing work—and I was just amazed and I was like, “Oh my God, do I work like that? Because if I do, I’m not really doing anything.” And it was this realization for me that I was like, “Oh man, I’ve got to be more conscious about how that looks like,” and now I pay a lot of attention to myself.
And the other is like the state of, your BlackBerry goes off or your cell phone goes off at five and you’re eating dinner with your family and you’re texting you’re responding. I have a thought, which is that it’s signaling. And it’s signaling in the sense that you’re signaling to your family that you’re important by taking yourself out of that moment with them, which is almost inverse signaling when you think about it, right? And you’re saying, “Oh well ,somebody at work needs me. so I must be important.” And that’s the message that people want to convey with that.
And I find it really interesting because I always, whenever I had demanding jobs that were more than outside of the regular hours, people would send messages and often, it was the people who are unhappiest in their relationships outside of work that were sending messages at like 11:00 PM or 2:00 AM or…and you were expected to respond. So it almost creates this virus of unhappiness because the more you respond, the more you get taken out of your moment with your family or your life and it gets interrupted, so the less happy you get. And then if you have people who are working with you, you do the same thing.
Jason: Well it’s funny, the first part especially, about watching people work, because I do the same thing when I go to a coffee shop or whatever. And it’s manic. It’s like switching and tabs and this app and that app. And in my head I’m like, “What are you actually doing? What do you actually do all day?” Because it looks like you skip. You just skip around. And by the way, maybe it’s unfair because maybe they’re just having coffee and that’s what they do on their break, or maybe—it’s hard to know but I do see that behavior all the time. This is actually one of the reasons why I use a laptop. I don’t have an external screen, so I have a 13-inch laptop and that’s my only screen.
Because I think screen real estate is actually like, you don’t want a lot of it. I think you want a little of it. Otherwise you end up like, you’ll walk by people in offices and there’s like seven screens up. They can watch their chat all day and this is not good. This is not NASA mission control, or you need to pay attention to critical systems. I’m a one screen at a time kind of person, and I try to stay as focused as I can and I find that to be valuable, but that’s just the way I work. But I do see a lot of manic switching and attention deficit disorder, essentially, when it comes to work. As far as signaling, I think that’s a really interesting point and I think you might be onto something there. Sadly, I think it might signal, “I’d rather be at work.”
Shane: That might be the other thing.
Jason: And there are moments in everyone’s life where like, I’d rather be here, I’d rather be there, like whatever. But essentially, I’d rather be there. And it’s probably a subconscious thing, but it’s unfortunate, I think. And as far as like the expectation of immediate response—to me this is a cultural issue, like broadly cultural issue, which is really unhealthy, which is this idea that, because communication is speeding up faster and faster and faster, the expectation is that someone’s response should be faster and faster and faster. The fact that I can text someone just because I happen to have a second right now to text someone, does not mean that they should be able to get back to me in the same amount of time that it took me to write them. They can be able to get back to me whenever they’re ready to get back to me.
And so like in our company at Basecamp, we try to think, the expectation is of eventual response, not of immediate response. Then if someone doesn’t get back to you quickly, it’s because they’re working. They’re doing something more important than what you had to say. And if someone gets back to me in three hours and that’s how long it takes. If they get back to you tomorrow or two days later, that’s how long it takes. If it’s an emergency, different story, but there shouldn’t be many emergencies. And if I’m really waiting on something from somebody, maybe I’ll ask him one more time and then I’ll just back off and that’s fine.
And there’s other things to do in the meantime, there have to be. If you’re always waiting, it’s like work is so delicate, and so that you need that one thing right now or you can’t do anything else, something else is wrong too. So, the other thing I like about the idea of eventual response versus immediate response is that in many ways, it forces you to go figure it out yourself. I need this answer from this person. Well, if they’re not getting it back to me, I’ve just got to figure it out on my own. And that’s a better outcome, ultimately, I think.
Shane: That’s a great place to end this conversation. I know the time is up, so I want to thank you. Hopefully we can do it again.
Shane: I have a million more questions for you. This has been a phenomenal conversation. Thanks so much, Jason.
Jason: You bet, Shane. Thanks. Anytime—I’m happy to have you do it again.
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