How to Be a Better Writer

Read more about Jason Fried in “Working Smaller, Slower, and Smarter.”

For our first episode of the year, host Matt Mullenweg talks to Jason Fried, the CEO of Basecamp. Jason runs a semi-distributed company that’s been making project management software for 20 years. He’s accumulated a wealth of wisdom about how trusting employees and treating them with respect can yield long-term success. 

The full episode transcript is below.

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MATT MULLENWEG: Howdy, howdy, and welcome to the Distributed podcast. I am your host, Matt Mullenweg, and I’m here with our first episode of 2020. Today’s guest is Jason Fried, the CEO of Basecamp, a semi-distributed company that’s been making project management tools for about 20 years now. Back in 2013, Jason wrote a book called Remote, which was an early manifesto for remote and distributed work models. I’m excited to catch up with him to hear about what he’s learned in the six years since that book came out and how Basecamp operates today. 

All righty. Let’s get started. 

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MATT: Jason, I am so glad to connect today.

JASON FRIED: Likewise.

MATT: Basecamp, formerly known as 37signals, has been in so many ways an inspiration for Automattic over the years, and I’m sure countless other distributed companies, so thank you for that, first and foremost.

JASON: Of course. And I would say likewise. I mean, you guys are even more distributed than us, so I feel like you’re the ideal situation where we’re getting there because we still have about 15 people in Chicago and we have an office that we’re maybe getting rid of, so we’re going to be following in your footsteps. 

MATT: Ah. So we had zero offices but then with the acquisition of Tumblr we’ve now got a space in New York again, so we’ve gone in the opposite direction.

JASON: Ahh, right. That’s funny how we keep trading. Yeah. We’re not sure what we’re going to do but our lease ends in August so we’re thinking about moving on, as in moving on to nothing and then trying to do that for a while and see what happens. And if that works out, we’ll do that. If not, we can always go back to getting an office again. But we’ll see.

MATT: Just for our listeners who might not be familiar with Basecamp, what do you publicly share about the scale of the company, customers, number of employees, that sort of thing?

JASON: Well we have about 56 people who work at Basecamp and we have close to 100,000 paying customers all-in across all of our different products. Although, Basecamp is the primary product, but we have Basecamp, we have Highrise, we have a few others, but basically it’s Basecamp in all three generations. Some have Classic, Basecamp 2, and Basecamp 3. 

This is as specific as we’ll be, but we generate tens of millions in annual revenues and annual profits. And we’ve been around for 20 years. This is our 20th year in business, and we have been profitable since the start. That’s a big thing for us, is to always be profitable. So that’s the only KPI, we don’t really use those terms, but that’s the only one we have, which is, let’s make sure we make more money than we spend every year, and other than that, whatever happens, happens.

MATT: How do you think about investing more or not?

JASON: We don’t have an investment shortfall kind of thing. It’s not like if we only had an extra — I’m just making up rough numbers here — an extra million bucks, we would do X or Y. We have everything that we need to do and we don’t want more people because we want to keep the company as small as we possibly can. So we have, not a dilemma really but it kind of is, in a sense, because I feel like we’re doing everything we could do and having more wouldn’t help us. 

In fact, I think in some ways it would probably hurt us. We’d be a little bit slower, we’d be probably doing too much work at the same time, which I think can often dilute what you’re really trying to do. We might take on more stuff than we really want to. We might just find work, invent work, to keep people busy. There’s always of course more work to do, but we believe in doing it at a certain pace, and I think having more people, or fewer people, at this point would kind of mess up that pace.

MATT: When you say as small as possible do you mean by customers or by colleagues and employees?

JASON: I mean employees. I mean the number of people who work here. We have always wanted to stay at 50 or less but we’re about 56 right now and that feels like a really good place to be, so we’re very comfortable with that. The thing is that we could have considerably more people, but again, we’re just not really — maybe we’re just not good at it. I’ll just take the blame for that. I’m probably not good at running a much larger company than this and I don’t think David is either. I don’t think we want to. 

I think it also keeps you a bit more honest in terms of the experiments you’re willing to do, which — and in some places more and more and more experiments is a good thing. I think a few are a good thing but I think too many — people can get stuck doing things that never ship over and over and I think that can be a bit demoralizing. 

So we think we’ve got a good enough feeling here right now at least. But then again, we’re the largest we’ve ever been, and I’m sure when we were 30 people we said 30 is enough. So we’re here at 56, that feels like enough right now. A lot of it probably has to do with the success of this other product we’re going to launch next year.

Because the one part of our company that does have to continue to grow is customer service. Product development doesn’t have to grow, we have enough people there, but as we have more and more customers, of course, we have to make sure we support them at the highest level. So that is one place where growth does continue to happen even if we don’t want it to.

MATT: Yeah, for Automattic that’s been pretty large. It’s been at points that half of our company was customer service just because we wanted to maintain a certain level there. And as the customers went up, it just got — it goes linearly. 

JASON: Yeah.

MATT: It’s one of those things that — of course you want to invest in making the product easier and documentation and self-help and everything like that, but at some level if you want a person talking to a person you need some more of them.

JASON: Yeah. You know, you want to do documentation and make things easier and everything, but I’ve also come to change my mind a little bit on it. Earlier on, when we had fewer people, we were focused on the self-help side of things and making sure our documentation was really good and our answers were great online and people could find their own answers. 

And we want to make sure that that’s true too, but I also see customer service interactions as a competitive advantage. Most companies are pretty terrible at it and the larger the company is, it seems like the worse they get. Try to email Google and get help. It’s like — forget it. Or Amazon, sometimes, but not always that great, although quite good sometimes also. It’s one of these things where the larger you get, the more customers you have, the harder it is to maintain that level of standard. 

MATT: Have you tried out a live chat for customer support yet?

JASON: Yeah we do that sometimes. And it depends on availability. And then we also use Twitter as well for that. Those things all work out really well. It just depends. We want to meet people essentially where they are, with the exception of we don’t have a published phone number, but if you want us to call you, we will.

MATT: Yeah. Live chat was a big step function for us. Both in terms of agent and customer happiness, because you can resolve things on the spot. 

JASON: Yes.

MATT: We do a support rotation where everyone at the company does customer service for at least one week a year. Mine is actually coming up in a couple of weeks.

JASON: Your turn, you mean?

MATT: Yes. So if you contact us in the third week of December, you might get me.

JASON: Ha! We do the same thing, we call everyone on support one day every roughly six weeks or eight weeks… So we’ll each do support for a few days a year throughout the year. It’s great and I’m glad you guys do that too. 

I think it’s one of the most valuable things you can do for a variety of reasons — camaraderie, hearing from customers and understanding the language they’re using, sensing their frustrations or their happiness or whatever it might be. And then also just having a lot of respect for customer service as a job and as a career. 

In a lot of places, customer service is treated as almost a part-time job, a stepping stone to somewhere else. But I think it can be a wonderful career and it’s just really nice to see the people who’ve dedicated their time here — and this is my only experience of course — to working in customer service for five, six, seven, eight-plus years and really see the work that they do and see how important it is. It’s our front door, it’s our front line, it’s really important to experience that.

MATT: What is your company breakdown now in terms of roles in the 50-ish?

JASON: I’ll give you some rough numbers because some people are multiple things, so you can’t really…

MATT: Sure.

JASON: I’ll give you the counts, it just might not add up to 56. But so we have currently, I believe 16 people in customer support, and that also includes, I believe — this might make it 17 or still 16 — the team lead. So all of our managers or team leads are working managers in that they do the work too. So 16-ish on customer service. 

We have seven-ish on technical operations, all the server work and that kind of stuff, all the low-level infrastructure work. And then we have four people on what we call the SIP team, which is Security, Infrastructure, and Performance. We have about seven full-time designers, we have around 15 developers. Actually a few fewer than that because some of them are now on SIP, but around that number. 

We have two people who do our podcast work, we have one data analyst, we have an office manager/bookkeeper. We have a Head of People Ops. And then we have David, who is CTO, and me, I’m CEO. We have a Head of Strategy and a Head of Marketing.

MATT: And did I hear it right that you seem to have a two-to-one or a three-to-one developer to designer ratio?

JASON: Yes. Close. Depending on — in some companies you’d consider ops programmers. It just depends on how you all add it up. But yeah, we have probably a two-to-one programmer to designer ratio. Or I should say product development programmers, because we have programmers who do other things. But on the product side of things, basically two-to-one.

The way a typical team is structured here at Basecamp is there’s three people working on something — three or two — never more than three at a time and when there’s three it’s usually two programmers and one designer and when it’s two, it’s one programmer, one designer. And then of course sometimes there’s some things that a designer can do on their own and sometimes there’s some stuff that a programmer is going to do on their own.

MATT: I’m going to toot your horn a little bit in that in your latest book, It Doesn’t Have to be Crazy at Work, there is an excellent chapter on the three-person teams.

JASON: Oh yeah.

MATT: I do think something that’s interesting. A lot of the listeners here get obsessed about the 1,000+ person distributed companies, and people sleep on Basecamp a little bit. But I think that would be incorrect, because you all are an amazing example because of your culture, your retention, everything, where you move really fast and do quite a bit for your size. And that’s where I think there’s a lot of learnings for companies of all sizes.

JASON: Thanks, we try. I think one of the reasons we’re maybe able to do that is because we don’t do a lot of other things that most companies do. We don’t have a lot of meetings, we don’t share calendars. It seems like a simple thing but it has such a huge influence. 

When nobody can take anyone else’s time through a system, people end up with more time to themselves. When you have more time to yourself, you end up doing better work and more work. You can get a lot more stuff done in a given day than maybe you could in another organization that has six times as many people but 20 times as many meetings, 30 times less time during the day to yourself.

So we try to avoid anything that breaks days into smaller and smaller chunks. So we are pretty anti-chat for work. We use chat internally in Basecamp for mostly social stuff. But any time there’s anything going on at work we write it up in longform and we post comments and we let people discuss it over a matter of days on dedicated pages inside Basecamp. So that’s the kind of stuff that we’re able to do, and it gives people a lot of their time back.

MATT: What are your favorite meetings? What do you look forward to? What’s a meeting you love?

JASON: Two or three people might get together in a room — typically it’s two — or on a Zoom call or something like that, to work something out, hash something out. That, I enjoy. 

I enjoy really working on a problem, like a design challenge or “God, how are we going to figure this out?” or “This seems complicated, how could we simplify this?” Or “What’s the best way to write this sentence? This headline just isn’t quite there.” That, those productive moments when we are actually making something versus talking about making something. 

I don’t like talking about making things, I like the making of things. So whenever I’m together with somebody and we’re working on something real, [I] love those all the time. And I’ll do that many times a week. But just to sit around a table and have people go around a table and talk about stuff that isn’t actually the work — I think it’s important to have those discussions, but I don’t think they need to be happening in person or via video. 

I think most of that stuff is better off written down. It allows people to really present themselves, a full idea. We call it “forcing the floor.” The idea being that if you’re standing up or sitting down, or whatever, in front of a bunch of people, and you’re talking for a while, there is a good chance someone is going to interrupt you and ask you a question or whatever. And there is nothing wrong with questions. 

And this is especially bad in chat rooms. You can’t possibly own a chat room for a while while you make a case. You just simply can’t. People will chime in and that’s a problem. Now, I’m not a big fan of chat, but there should be a pause button when you chat. You should be able to hit pause, which would prevent anyone else from saying anything while you’re talking. 

The reason that should exist is because you need to have the floor. You need to make your point. That allows you to work your thoughts out yourself, get your thoughts together and put them out there in the world as a single unit. And that allows other people to read that single unit uninterrupted and take their time to respond back to you. 

If you’ve taken three days to think about something and you say it in a meeting and people start just throwing stuff right back at you — in some ways you’re asking them to because you’re sitting at a table, what else are they going to do? But it seems unfair to them, in fact, for them to have to react to this thing that you have thought about for three days or three weeks or three months, for them to have 30 seconds to say something back seems unfair. 

By writing things down in longform and publishing them and giving people a chance to get back to you on their own schedule, I think you end up with much deeper and fairer discussions and better discussions. So that’s why we do have, quote, “meetings,” in a sense, but they’re not meetings in time, like around a room physically or even on video, they are written down and people respond over a number of days, on their own schedule, and those conversations are much richer.

MATT: Well that emphasis on writing and the well-written word, how does that influence your hiring process?

JASON: It plays a big role. Aside from somebody being able to do the job — obviously, the fundamental job — beyond that you’ve got to be a great writer. If you’re not a great writer, you will not get the job. 

The first thing we look at whenever someone applies for a job is the cover letter. We don’t look at the resume first, we look at the cover letter first. And the cover letter is the first filter. Can this person explain themselves well? Are they clear-minded? Are they clear writers? Are they clear thinkers? Do they want this job, or are they just applying for any job?

Typically a resume is going to be sent to every job the same way, for the most part. You’d hope that cover letters are not. You’d hope that cover letters are customized for the job.

MATT: You would hope. [laughs]

JASON: You would hope. I can tell you’ve done a bunch of hiring yourself. Yeah. So most of them are not. And those are immediate no-gos for us. If you want to work here and if you want to work at any job, I would say you need to write down why you want to work here, not just why you want a job. And from that, you can derive a lot of things as a hiring manager, as someone who is involved in the process, you can really tell where someone’s head is. 

So writing is very important, and then we often give a lot of writing exercises through the job hiring process, depending on what it is, and continue to double down on that. And every time we’ve been hesitant about someone, their skills have been great but they weren’t great writers, it turned out that we probably shouldn’t have hired them. And the main reason why here is because most of our communication is written, almost. I’d say 95% of it is written. 

MATT: Let’s say I was a colleague of yours at Basecamp and you were going to coach me or give me pointers to resources or something to become a better writer, how would you do that?

JASON: My favorite book on writing is a book called Revising Prose, and the cover — I think it’s in the fifth edition now — the fifth edition cover is horrible. It’s a CD-ROM. It’s a picture of a CD-ROM, it’s the strangest cover of a writing book. But Richard Lanham is the author of Revising Prose, fifth edition. 

It’s outstanding because it’s a book about writing sentences. It’s not about grammar really, it’s not about elements of style or rules, it’s about how to hone a sentence, how to get a sentence right, how to make a point. It’s a very, very good book. I’d recommend reading that first off and then I would write and write and write and write. 

And I would work with you to review your writing, your headlines, your sentences, whatever you’re going to do and talk about, like, “We could say it this way or maybe you could say it this way. And if you said it this way, it would feel like this. And if you said it this way, it would feel like that.” I like to talk about feeling when it comes down to writing, so how does this come across, what does it make the reader feel, what does it elicit in them — that kind of stuff.

But it’s the process of whittling something down and not losing any detail as you go, maybe even picking up detail as you go, until of course you hit a certain point and then it’s more of an academic, fun exercise to whittle it down to one sentence and one word.

MATT: Basecamp has a pretty unique structure. Do you look to any other tech companies or outside of tech or companies in general that have inspired you to the structure of how you do things there? 

JASON: I tend not to look at tech companies mostly because I think it’s healthier to look outside your own industry most of the time. We’re inspired by what you guys are doing at Automattic because you’re fully remote and you’ve been around for a long time. In broad strokes, I like to look at people who have been around for a long time because I feel like if you’ve been around for a long time, it’s not a fluke.

MATT: I know you follow the watch world and I know you like… I think you like Cucinelli, actually. Are there any examples in that realm that you like?

JASON: Yeah, Brunello Cucinelli, I don’t know him but I admire his ethos and how he runs his business. I consider him a mentor because of the way he runs his business and how he’s all about integrity and dignity. And there is a lot you can learn from that. You don’t need to talk to anybody to learn that from him. So I think there’s a lot of really wonderful examples. 

In the watch world, the mechanical watch world, which I am a bit too absorbed in these days, there’s a lot of old businesses. I mean some of them are hundreds of years old, many of them are family-owned and have been passed down through generations. I just find it fascinating. To see how different generations do different things is fascinating to me. And to see how something can last beyond a generation.

I always often think, well we’ve been in business 20 years, I’m 45 now. If we’re going to last another 20 years — which I hope we can, I’d love to — I’d be 65, I probably shouldn’t be running a software company at 65, it’s probably not the right thing to do. So what’s going to happen? Who is going to take over? How are we going to do that?  

We haven’t really thought about succession planning but at some point you have to. It would be sort of a shame for a business to die with its founders just because they didn’t think about who else could do the work or anything like that. So it is interesting to think about how something can last beyond you, beyond your own generation, and also how it should change or shouldn’t change. 

For example, in the watch world — the watch world is a very traditional world with arts and crafts and science passed down through generations, and a lot of that is very traditional, it doesn’t change very much. But then you have these upstart independents, and they are the ones who actually change things for the most part. And sometimes it takes someone brand new to change something. 

Other times, you don’t want to change things. You’ve got to figure out “Can a software company not change?” Probably not. A restaurant probably could not change.

MATT: I get super fascinated with companies or businesses that are able to do that multigenerational.

JASON: Yes.

MATT: So where there’s different leaders over time. Because that gets even harder, right? It’s one thing to have this passion yourself but to be able to pass that on and have it maintained or hopefully improve is really, really hard. All great companies I think are fractal. So how do I make a division at Automattic have what was great about Automattic when we were 30 or 40 people and that division can operate just like we were at that point.

So that’s one way I think about scaling as well. The whole thing doesn’t have to be big because most people don’t have to keep the whole thing in their head, they just really work with their team or division or area.

JASON: Yes, it’s so true. And the other thing that’s great about the fractal viewpoint is that you don’t have to change an entire organization to have an effect on it. You can change a corner of it, an edge of it, a branch of it, and then those other branches and those other corners and those other edges can look back at that change and go “Ohh, I want some of that too.” And that can carry through. It can sort of bleed into the rest of the business, which is great.

MATT: And there was a point when we started to scale a little bit in terms of number of people, and also breadth and depth of what we were covering — that’s when I started to think about it a lot. It’s amazing how many companies will experiment and do a ton of A/B tests with their product or their customers but never really test internally how they work. 

JASON: Yeah. 

MATT: You know? Have two teams have the autonomy to work completely differently and then just judge it by the results. We even had a division which tried holacracy once.

JASON: Oh yeah.

MATT: Which was kind of the rage at the time. And I’d read about it and I’m like, “Hmm, I don’t know if I buy all this but I don’t know…”[laughs]

JASON: Maybe, yeah.

MATT: Let’s try it. They had to maintain their interface to the rest of the company, which is fine, because they were relatively self-contained, but internally they did a pretty substantial, maybe six or nine month experiment with holacracy, and it was actually really cool because coming out of it, they decided not to continue it, but they said “but this really worked well,” and “this is what we’re actually going to bring back,” kind of cherry-picking what they found to be the most effective part of it.

JASON: What was that part? 

MATT: Part of it, that we’ve adopted pretty much throughout the organization, is this idea of a DRI, or a Directly Responsible Individual. Someone owns everything, but people wear different hats but those hats are clear. I think it can be tough when those hats are not clear, or when someone has too much, they’re not explicit about what they’re doing, they take on too much and then become a bottleneck. So when you can be more explicit and transparent about those things, you can generally avoid those problems. Not always but at least it’s apparent where it is.

JASON: We’ve even struggled with that. For a long time, we didn’t have titles here. We thought titles were what you do at big companies, you had titles. And then for a while we allowed everyone to make their own title, which was stupid, but we thought it was cool. 

MATT: [laughs] We still do the own title thing. 

JASON: Okay. [laughs] Well, stupid maybe is unfair. But let me say the reason we discovered that titles matter is actually, people have careers after Basecamp, and it’s tough when you don’t have a title that matches up with the rest of the world, in a sense, when someone else can look at your title and go, “Oh, I know where they are and what they have done and what position they’re in and where they’ve come from and the whole thing.” 

So we decided to get extremely boring with titles. It’s like: junior programmer, programmer, lead programmer, senior programmer — boring titles. We also made sure everyone has one or had one. For a while people were like, “Oh I’m just a designer.” Well, no, you’re actually not. You’re a senior or principal designer. Other people should know where you are in the organization as well.

MATT: Well it sounds like you’ve combined leveling with titles as well.

JASON: We did.

MATT: Did the leveling process always line up with where people thought they were?

JASON: No. And that was the other thing is that when we ended up switching to standardized salaries across levels and across roles, we had to make a lot of things clear for everybody, so everyone knew where they stand and what salaries attach to each level and each role. So there’s no salary negotiations at Basecamp. If you’re a senior programmer, you get paid X. If you’re a lead designer, you get paid X. And that way you know that everyone else who’s a lead designer who does the exact same work you do — same skills, same experience — gets paid the exact same.

MATT: And that’s regardless of geography?

JASON: Regardless of geography. So we pay everybody 90th percentile San Francisco rates, even though we have nobody who lives in San Francisco. We basically want to pay the highest salaries in the industry. Of course 90% means there’s 10% that might be higher than you but that’s pretty high. 

So that way you never have to wonder, you never have to hear — because things leak — “Why does Bill get paid $172,000 when I get paid $164,000? I thought we were both senior designers.” That stuff happens, people talk, and that’s where discontent begins to foment and it gets dangerous because people then don’t want to talk about it, and they hold resentments.

And also, the other thing is that there is no reason why you have to be a great negotiator to get what you’re worth. It’s hard enough to be good at your job, and then to also be an ace negotiator doesn’t seem fair. People don’t like to negotiate for their cars, for their houses. I mean some people love it but — 

MATT: And it’s asymmetric too because you know everyone’s salary and you do this all the time where they’re going to only do it once every time they change jobs or once a year or something.

JASON: Bingo. 

MATT: Yeah.

JASON: Yeah, and think about a manager who manages 12 direct reports. Well this manager gets to practice a lot of salary negotiations while each individual person barely ever does, once every couple years, whatever it might be? And they’re going to be nervous and you’re going into someone else’s office. It’s hard. 

We wanted to eliminate all that and with all that — this is kind of a bigger systemic change, which is unified salaries, leveling, and titles were all tied together — [we] just eliminated a whole bunch of questions and unease and — dis-ease, I should say. A few people didn’t like it because a few people thought they were worth more than the role or the level that they were at and I understand that.

MATT: Did some people get adjusted down?

JASON: No. So our policy was, nobody got adjusted down. What would happen was if anyone’s salary was above the level that they were placed in, their salary would be higher than everybody else’s, but they would never get a raise until everyone else caught up to them, basically. 

So it was like, here’s your number, here’s where you’re at, maybe you’re $6000 more than someone — I’m making up numbers here — but $6000 more than someone else. You’re at 156 and everyone else is at 150. Other people are going to get raises as the industry moves and as the standard of living increases. You will not until they catch up to you and then you’ll all move in unison again. If the industry moves down, we will not move anybody down, we have made that promise as well. So you might not get a raise for many years until the industry catches back up again but that’s how we’ve set that up. So no one ever loses salary.

MATT: How do you deal with foreign exchange? Because you must have people outside of USD.

JASON: It depends on the role and — I should say the country, not the role, the country. Since exchange rates do fluctuate, basically they submit invoices every few weeks and some of that is adjusted based on if there is a significant fluctuation. 

And the other thing that’s tricky is benefits. Because in some countries, for example, in most countries, pretty much every country, healthcare is included essentially. Here it’s not. So we pay people’s healthcare, or most of it. We pay 75%. So we do basically a cash-equivalency benefit to people who live in Canada or who live in Spain or something like that. So the numbers can’t be exact but they are really, really, really close and we do our best to make them as close as is reasonably possible. 

MATT: As we wrap up, we’re coming up on ten years since Remote was published.

JASON: Yeah. Wow. 

MATT: Which is kind of wild. Now there’s a ton of companies doing remote too, so I would say it’s not “mission accomplished,” but it’s really shifted now where there’s a lot of companies. I’m hearing now from my investor friends that it’s actually the default now, even in the Bay Area. New companies are being built this way.

JASON: That’s great.

MATT: What do you feel like has changed the most and what do you really want to see change for companies operating in a remote or a distributed fashion?

JASON: I’d like to say it’s technology and whatnot but I really actually don’t think it is. I think what ended up happening is that cost of living got so high in San Francisco and continues to get so high in San Francisco that it just doesn’t make a lot of sense for a lot of people to live there anymore. And so at some point if you want to find great talent, you’re going to have to look outside the walls of that city, and that region, because a lot of people just simply can’t afford to live there. And so you begin to realize that hey, there’s great people everywhere, all over the world. Amazing people. 

And I think it just takes a few companies, like Stripe is a good example now. They’re opening up the remote HQ or whatever they’re calling it. Companies that are widely respected. Of course Automattic is widely respected, but you’ve always been this way so it’s more about the companies that have been all about [how] everyone’s got to be together. Those are the ones I think that people are looking to and [saying] “Oh wow, they are even considering going remote, that’s interesting.”

Meanwhile, I think what you guys are doing is incredibly interesting, but you’ve been doing it for so long that things don’t become interesting anymore after you’re like, “This is what we do.” [laughter] 

But yeah, to see someone like Stripe and other companies doing that, that gives other companies cover and investors cover to go “You know what, if they can do it, if they think it’s okay, if they’re going in the opposite direction of what they believed five, six years ago, then maybe this is okay. And you know what? We can find some great people. And guess what, there are great people. And wow, they’re finding great people, there is a whole world of great people, there is a lot less competition out there for great people when you can look at the whole world.”

So I think all those things are finally beginning to happen. Like, video conferencing has been around forever, text messaging has been around forever. It’s not like some new tech came out. It’s really I think just an economic reality. And then of course just people getting more used to things and a new generation coming up that feels very comfortable with it, and some of the people who were very opposed to it are just going away, in a sense. They’re realizing, well other people can do it, and let’s give it a shot.

So I hope to see it more and more and more. I think it’s wonderful for everybody involved. It’s, to me, the most respectful way to work. I have always found it borderline offensive that someone would have to lose their job because their partner that they live with had to go somewhere else to get a job. 

So you’re living with someone and they have to go move to Madison, Wisconsin, because that’s where the work is. And you’re working for a company in Chicago but you’ve got to move because your partner has to move, and all the sudden you have to lose your job. Why? That seems so horrible for everybody. 

It’s bad for the employer, because now they lost someone who was great and now they have to find someone new and train someone new and all that institutional knowledge is gone. And it’s bad for the employee who feels like they have to be chained to a city. And/or things far outside their control can cause them to lose a job that they might absolutely love, they might have spent their whole life trying to find this job and they got it and now they have to leave because someone else in their family has to go somewhere else. It feels so unfair.

So I think remote is so fair. I think it’s important, really important, and I’m glad to see things changing.

MATT: Jason, thank you so much.

JASON: Thanks so much. Great to hear from you again and catch up in this way and hope to do it again soon.

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MATT: That was Basecamp’s Jason Fried. You can find him on Twitter at @jasonfried. That’s Jason F-R-I-E-D. He’s on Instagram at the same, but I believe he’s trying to quit both networks. So probably Basecamp’s website and the Rework and Remote podcast are the best places to find him.

Basecamp has been building productivity tools for 20 years, which makes it pretty advanced for an independent tech company. In a world where many startups race to make it to the next funding round, sale, or IPO, it’s refreshing to see leadership that see themselves as long-term stewards of a company, mission, and most importantly, their users. I’m grateful to learn from folks like Jason who’ve been at it a lot longer than I have. 

On the next episode of the Distributed podcast, I’ll be talking to Merritt Anderson, an HR veteran who advises companies about distributed work, among other things. She spent over four years in HR at GitHub, helping to build out their distributed teams and the policies that facilitated that work, and a really interesting hybrid model with a ton of success from both a user point of view and of course an outcome point of view.

Thank you for listening, and see you next time.