This week we’re excited to share our conversation with Jason Fried. As many of you know already, Jason is the Co-Founder and CEO of Basecamp – one of the world’s leading software applications for communication and team productivity. He is also the best-selling co-author of "Rework", "Getting Real", "Remote" and most recently "It Doesn’t Have to Be Crazy at Work".

Jason is a brilliant communicator and was a pleasure to talk to. We dive into things like his decision making process, the state of tech as an industry, downsides of remote work and much, much more. One of the things I believe attracts people to Jason’s work is that he is honest, straightforward and clearly very knowledgeable. As a result, he’s got a refreshingly original take on most things. I hope you enjoy this conversation as much as I did.

Please make sure you follow Jason on Twitter at @jasonfried and check out his writing on the Basecamp Blog Signal vs Noise. Also, check out their latest book – Shape Up, which is (in typical Basecamp fashion), available online for free.
Find it here.

If you want to make work feel like less work, check out Basecamp and try the product for free today..

Be sure to check out Basecamp's awesome podcast -- The REWORK Podcast at rework.fm.

What Jason’s reading regularly:

Kottke.org by Jason Kottke
dish.andrewsullivan.com by Andrew Sullivan
daringfireball.net by John Gruber
Berkshire Hathaway’s letter’s to Shareholders by Warren Buffett Compiled version

Matt H: 00:00 Hello, everyone, my name is Matt Hollingsworth. And welcome to another episode of the Remote Show, where we discuss everything to do with remote work, entrepreneurship, business, technology, and much more. Thanks so much for listening. The Remote Show is brought to you as always by We Work Remotely the largest community of remote workers in the world. With over 220,000 unique users per month, We Work Remotely is the most effective way to hire. My guest on today's show is Jason Fried. I'm sure most of you have heard or know of Jason and his work. But for those of you who don't, he is the founder and CEO at Basecamp, one of the world's leading and project management and team communication software applications that combines all the tools teams need in a single straightforward package that makes work feel like less work.

Matt H: 00:51 Jason is also the co-author of Getting Real Rework Remote, and it doesn't have to be crazy at work. They also have a new ebook called Shape up, which outlines Base Camp's approach to shipping and meaningful products. Go to basecamp.com/shapeup to get that content absolutely free. Jason, thanks so much for being in the podcast, we really appreciate it.

Jason Fried: 01:13 Glad to be here.

Matt H: 01:14 So I think what I typically do with these podcasts is I like to talk about how people got their start and then talk about a little bit what they're working on. I think in this case, most people know about you and about base camp. So I thought an interesting place to start would be to talk about what it is that you're most proud of over the past year, whether that's in base camp or otherwise. But what's the thing that you're most proud of that you've done over the past year?

Jason Fried: 01:34 Well, whatever I say, I'll probably miss something that I'm more proud of. But something I'm particularly proud of, I think as an organization is that we've changed our minds a bit. We've been at this for 20 years as a company. And it's easy to kind of get set in your ways and make some decisions a few years ago that we feel like need to stand forever, because they were big decisions at the time. About four or five years ago, we decided that we were going to become Basecamp and focus all of our energy basically, in one product called Basecamp and we have done that since. But earlier this year, we had a new idea that we just couldn't get out of our heads. We're currently working on another product, which we said again we would never do. So I'm proud of us for giving that a try, even though we said we wouldn't do it.

Jason Fried: 02:13 And also we're currently hiring a Head of Marketing, which is something we've never done before. And we're currently hiring a few other people on, we had a hiring freeze in place for a while. So we've been deciding to change our minds a lot lately. And I think that's a good thing.

Matt H: 02:28 And I was hoping to get to this later. But I guess it's relevant now. So do you go back and read your previous writing? And then if so, what is it that you've written about previously that you most disagree with now? Whether it's in your blog, or your books, or through Twitter. Is there anything that sticks out of your mind as particularly something that you disagree with?

Jason Fried: 02:45 I don't tend to go back and read things that I've written mostly because I expect my mind to change. And I don't really feel like I need to go and find something that I disagree with today. But certainly there's many decisions that I've made that I think maybe weren't the right decision at the time, but turned out over time, maybe not to be the right decision today, that happens frequently. I don't think of it really as the wrong decision. It's more like it was the right decision at the time and the time has changed. And so therefore, today, I may have a different point of view, or information is different, or just our mood is different, or our appetite is different, that sort of thing. So yeah, I'm not really that interested in going back and making sure that I'm consistent or anything like that.

Matt H: 03:29 Do you find that it is more difficult to stay consistent with the ideas that you've presented if they are in writing and published out there? Or is that something that you don't really consider?

Jason Fried: 03:37 I just don't care. Yeah, I don't care. I expect people to develop and change their minds. I'm not interested in being consistent. I'm sort of interested in being as correct as I can be, in the moment, given the information I have and the context and all those things. That's what I'm curious about or that's what I'm trying to do, is try to be sort of as right as I can be most of the time, given what I know, and given the situation, versus, saying, "Hey, I told you so 12 years ago." Or something. I don't really care about that sort of thing. I told you so is a bad thing to ever say or feel any way to begin with? I mean, there's some principles I have, I would say are consistent. And there's some points of view and some, ethical decisions and things like that, and morals and whatnot, you have that you hope are consistent over time.

Jason Fried: 04:24 But business decisions and things like that, that's all about the moment. It's not about something, you need to look back and improve that was right or wrong or something five years ago, whatever.

Matt H: 04:34 Right. Yeah, it's interesting that your consistency biases is one that's I think, stronger than people realize, especially those who write publicly, and there is a tendency to just continue with something just because you've written about it publicly. And people need to, I think, fight against that more so than they believe that they do. So yeah, that's super interesting.

Jason Fried: 04:51 Yeah, it's like I've said things and some people will point things out. So well, "You said something else before." It's like, "Yeah, I said something else before. This is what I'm saying now. What does it matter what I said before? It matters what I said before at the moment, but it doesn't necessarily matter now. What matters now is the information I have now and the decisions I'm making moving forward." I think though, if someone wants to look at my record, or whatever, if they really were into that sort of thing, I think a good 80, 90% of the things I've believed, I continue to believe. But I think also, there's a number of things that I've changed my mind on and I think that's healthy. And if you don't change your mind, and if you're focused on consistency, I think you're probably going to miss out on a lot of things.

Matt H: 05:28 Yeah, for sure. Just going on that a little bit. Is there other people out there that are either writers or in some way publicly visible that you don't miss in terms of their writings or their speeches or something like that? Is there someone that you follow regularly that you think other people should know about?

Jason Fried: 05:43 I visit daring fireball. So John Gruber, I visit his site frequently. I love his writing. I've always liked Jason Kottke, writing so Kottke.org, I really enjoy reading Andrew Sullivan who's a political writer. I just like his writing style. He seems to consistently battle with himself about where he stands on things. And I think that that's really healthy. I love reading Warren Buffett's letters to shareholders, I think that's probably some of the best writing on an annual basis I've ever read from an individual. So I love reading his letter every year. I know that's kind of a good set of people. I think right there. There's others, I'm sure. But I'm not really a big consumer of media. I don't regularly read magazines, or newspapers or review sites or industry stuff. I like reading some people because I like the way they write. It's not even so much the subject matter sometimes it's just, I really enjoy sentences. I really enjoy words, I enjoy putting things together. And so I like observing how other people write.

Matt H: 06:44 Is that a conscious decision as a matter of just your time and protecting your time? Or do you have another reason for not consuming as much media?

Jason Fried: 06:50 I would say a little bit of that and also, I just don't feel the need to be up on everything. I in fact, I prefer to miss out on most things. I'm not really interested in the information Olympics is what I kind of call it, which is everyone's competing to be on top of everything that's happening. People even ask me about stuff in our industry, like, hey, did you see that thing? My answer is usually no, didn't see it. What is it? Tell me about it. Or did you see what that person said about this? No, I really didn't. Tell me about it. And so when there's something I'm supposed to have seen or should know about or whatever, I'll find out some other way, it's that important versus trying to stay on top of everything.

Jason Fried: 07:25 I also, I don't really like to be influenced by my own industry. So I tend not to pay much attention to the industry in general, I'd rather come at it with a beginner's mind as much as I possibly can and just do what I think is right. I think in a way, the more you pay attention to your industry, the harder it is to be an individual, to be a fresh thinker. All these ideas have their own set of gravity and I think your thoughts begin to get sucked up by these other ideas, and you tend to sort of fall back towards what other people are doing. And so I just don't want to know, basically. So I pay attention on other things. I pay attention to architecture, I love nature, I love going for walks, I love reading a whole bunch of other things about science and all sorts of other topics that I'm interested in. But I try to stay away from my own industry in terms of being up to date on what's going on.

Matt H: 08:15 And so with that, obviously, you have within your team, I'm sure you have people that are trusted advisors and to be able to bounce ideas off of and you mentioned you don't really consume the media. But is there a group of people or a specific person that you have, that you do like to bounce ideas off of in terms of your own industry? Or is that specifically to like, based on first principles that you said, come up with just you as an individual, or how does that work in terms of just sharing ideas within the space you're in?

Jason Fried: 08:39 Yeah, I'd say there's a few people internally here at Basecamp, where if I'm working in an idea, depending on where the idea is, I'll talk to different people about it. Some people I like to talk about, really raw, early ideas with and other people, I would hold off and sort of form it up a bit more before I share it. I just think different people have different perspectives that come in at different times. And they're more valuable at different times. So some people are really good, I think at refining an idea. Others are really good at seeing it in the early stages and knowing where it could go. Other people are really good at challenging an early idea. In a way I think that's too forceful. Other people are really good at challenging ideas in the early days to help form them.

Jason Fried: 09:23 So it sort of depends. So yeah, there's definitely a handful of people here that I'll share stuff with, it just depends on the stage of the idea.

Jason Fried: 09:30 And of course, some people, I'll just be talking about an idea. Then we'll come up with something else together, that's just totally different from what the initial idea was. So that happens as well. I don't believe in the lone wolf kind of thing at all. But ideas come from somewhere, they'll start somewhere, and then you can bring them to people and see whether they take them. Or maybe they'll reinforce them or maybe they'll push them away, or challenge them in other ways. But I do think it's important to have that. But yeah, I don't typically go outside the company for that sort of thing.

Matt H: 09:57 Right. So it sounds like you have a lot of trust. Maybe this isn't the case. So you can correct me if I'm wrong, but trust in your own judgment and decision making at this point. So you sort of, you take different variables, and you kind of funnel them through and you make a judgment call based on those things. Have you found there's an effective way of getting better at that and getting better at I guess, decision making in general? Is it just time and practice that really forms the basis for your decision making?

Jason Fried: 10:23 Well, first, I think it's hard to get a bunch of things right in a row anyway. So I mean, what I like to do is that kind of think in bets. I know there's a book out called Thinking in Bets. And that's not what I mean. But basically every idea is a bet. And you're just like how confident are you in this bet? Some things are long shots, some things are maybe more sure wins or whatever. It all depends on the scale of the bet. And also the downside of it. So I tend to think a lot about asymmetric risk. Well, if I get this right, what's the upside? And if I get it wrong, what's the downside, and if the downside is small, the upside is big, well and then it seems like it's probably worth trying. If the upside is small, and the downside is huge, and maybe it's not worth trying. Just kind of think of things that way. As far as getting better at it, I don't know, it's probably a lifelong pursuit, I don't consider myself great at it, I just tend to try to make bets that I think are worth making.

Jason Fried: 11:16 Something we talk a lot about internally is this idea of taking a risk, without putting yourself at risk. So I'm not interested in putting myself at risk. I'm pretty risk averse in general. So if I'm going to make a bet, or come up with an idea, or wherever and go for it, I want to make sure I understand the worst case scenario before we start. And in some cases, the worst case scenario is we spend 10 months or a year on something and it doesn't pan out. That's pretty bad. But that's not going to put us out of business. But if we're saying well, we're going to spend $50 million marketing this thing, that could be a bad move, if it doesn't work out. Of course, I'm just exaggerating there. But that's how I approach these things. So everything has that degree of risk based on the downside and the upside potential, and then just feeling comfortable and confident.

Jason Fried: 12:01 So like when we get things wrong, it doesn't hurt that bad and sort of, the ultimate goal is of course to get it right. But if we get it wrong, it's okay, I want to be okay, if we get things wrong. And that's kind of how I look at it. And of course, we're in maybe a different position than some since we've been in business for a long time, we have a very stable business, and we can absorb a lot of blows, basically. But we've always felt this way. I just want to know what the worst case scenario could be, and if I'm okay with that, and the upside seems like it has enough potential then I think it's worth giving it a shot.

Jason Fried: 12:30 Of course, one other thing I would say is that, you also have to weigh that against all the other things you could be doing too. So it's not just about that one idea and that one thing, it's like, well, if we do this over the next year, what can't we do? So that's another part of the downside risk calculation, what's the opportunity cost here? And is it worth it? And are we at the right moment in our company's history and time to do this, to leave this to do that, and kind of that sort of thing? So it is sort of looking at the big picture, but ultimately, it's measuring the downside and measuring the upside and figure out what's worth it?

Matt H: 13:01 Yeah, no, it reminds me a little bit about what Charlie Munger and Warren talk about when they talk about their areas of competency and being really comfortable with the idea that they are understanding of the risk. And I think it sort of plays out into more of things than just, investing in decision making. And like you said, it seems like you just have to know and be very confident and comfortable with the risks involved before obviously being able to make a decision based on those risks. So I think a lot of things can be attributed to at their circle of competence.

Jason Fried: 13:27 Yeah, it's not so much about even how often are you right, or whatever it's just like, how many mistakes can I make and still be standing? I'm sort of a little bit more interested in that to be honest, because I would never expect to bat a perfect score or whatever. So essentially, gambling, you go gamble. And let's say you have a hundred bucks in your pocket, well, you probably don't want to put a hundred bucks on your first bet, because you'll lose that and it's over, you can't bet anymore. I want to be able to survive longer to have more chances to hit something that works. So that's kind of how I think about it.

Matt H: 13:59 Yeah, I know that you don't like to maybe make roadmaps for the business. And you've talked about that in your books before. But is there something that you would look back on in five years from now and deem yourself successful if you've accomplished that? And I guess the better way of asking that, is there a broader mission or a problem that you're looking to solve and that you'd consider a success? If you did make strides towards solving it?

Jason Fried: 14:20 It's not really the way I would look at it, I guess I would say the way I tend to evaluate success is basically would I want to do that again, like would I want that to happen again, would I want to go through that again, and or am I enjoying it now? So for example, if we make this week, we are making this new product. And if we launch it, and three years down the road, I look back and go, that was worth it, because we enjoyed the process and we're using and a lot of people like it and the whole thing, that would be great. But like, for example, it was a financial success, but we all hated supporting it. And it was a huge pain in the ass to handle and all these things. It's like, on paper, it's a success. But I wouldn't want to do that again.

Jason Fried: 14:58 And there's been things we've done that have been on paper, very successful things, but we've decided to walk away from them, because they just weren't what we wanted to do anymore. And so they were textbook successes, but in our world, they weren't something we don't want to continue to do. So I would call them not failures by any means. It's just like more like, just don't want to do that again, or just don't want to maintain this anymore, or just don't want to be involved anymore, because our opinions have changed, or our interests have changed or our focus has changed. So therefore, let's let someone else do that.

Jason Fried: 15:32 So I don't know. It's not about like, in five years, do I hope 100 million people know about base camp. I don't think that way, you're just making stuff up, then it's more about, do we enjoy that? Was that enjoyable? Is the company better? Are people here happier? Are we stronger as an organization? Those are the kinds of things of course, we have to stay in business, so it has to be financially successful as well, just to make it viable. But I'm watching looking back, if I'm going to look back at all and go, was that worth it? Like how to come up with the answer is a number of things. It's not just, financial, or it's not just users or it's not just like that. It's like, what did this do to the company?

Jason Fried: 16:08 We just released this book yesterday called Shape Up. And I wrote the foreword Ryan singer wrote the book, I wrote the foreword, and part of the foreword is all about how people often like to say, execution is everything, but I don't think that's true, because you can execute something perfectly, but you can destroy your company. You can destroy the morale. The product in the end can be great, but the process to get there could have ruined and wrecked friendships and working relationships. Morale could be destroyed, people could be ground down. So it's not just about the execution, it's about how you got there, too. And that's a department for us.

Matt H: 16:42 And just going on the Shape Up thing, well, I was just actually looking at that and reading it. And it's, as always a super enjoyable read. So we'll link to that as well. But a part of the process, as you said, was the idea that, success isn't necessarily measured by the financial piece of it, but also the fact that your company is happy and you guys, so enjoy your work. Is that something that you learned by trial and error? Or was that just something that you picked up as sort of a no brainer thing to do? And I guess my question is, why is that not more widely adopted within especially tech, but in just business in general,

Jason Fried: 17:16 I think I probably saw it on the personal side of things, first, I've met a lot of textbook, successful people who are absolutely miserable. And so they've amassed their fortune, and they've done all that and they're miserable, or they just want more and more and more, and they're never satisfied. And you see that enough. And you go, I don't want that to be me. It doesn't mean that it has to be but like I've run into enough of them, that I detect a bit of a pattern that when you're just after that when you're measuring yourself in that way, it's ultimately pretty hard to be satisfied. And also, we've been in business now for 20 years, this is our 20th year in business, if you want to build a long term sustainable business, which is what we want to do, you have to enjoy the work. It doesn't mean you have to love your job every day and that, but on balance, you have to enjoy the work, enjoy the process and enjoy essentially doing what you do every day for the long term.

Jason Fried: 18:10 And I think if you're just chasing numbers, it's ultimately hard to enjoy it, when things go well, and things go wrong, and all those things because you're just looking at the numbers versus looking at the overall impact it's having on you. And so I don't know, I don't want to make it sound like there's some deep philosophy here other than it's just kind of baseline basics, which is I want to hopefully enjoy what I'm doing more often than not, I want to do it for a long period of time. And in order to want to do that for a long period of time. You have to be motivated by something beyond money, because frankly, I'm independently wealthy now I've made more money than I'll need. So that certainly better not be the motivation here. Because if that's the motivation, and then I'm out of it, I'm out of motivation. So you got it, define some of the things.

Matt H: 18:54 Yeah, yeah, for sure. Have you seen it broadly get better in terms of that mind shift away from the numbers chasing and the amassing of fortune and wealth as sort of the number one motivator for people to be in business? Is that something that you've seen a trend against? Or is that still the case with most tech entrepreneurs and people involved in business that that's the motivation as opposed to this sort of long term, sustainable business model? Let's be in business in the next 20 years, have you seen any change there?

Jason Fried: 19:25 I think it's gotten worse. Yeah, I do. Because a lot of the focus these days is on ... There's even terms, like unicorn wasn't like a term, 10 years ago or whatever, probably there's terms for these companies that have outsized gains, and have grown so fast. And it seems like that's what everyone wants to be, at least in our community in the tech, community, they want to be the next big huge thing. And there's so much money out there, backing so many companies, and there's so many more ways to raise money and get money. And I've just seen it get worse. And I don't think it's going to get better for a while, unfortunately, until there's a shakeout, I think the current generation of entrepreneurs, let's say younger ones in their 20s, they haven't gone through a shakeout yet. And I think until you do, you probably don't recognize some of those lessons, you haven't learned them yet.

Jason Fried: 20:10 We've been through like in 2001, or 2000, it's kind of a downturn there. And then in 2008, downturn, there's been other little micro turns here and there. So, we've kind of seen a few of those and you sort of expect them over time. I think a lot of people these days, don't expect that to ever happen again. They think that now it's different, that there'll never be a downturn, never be a downtime. And let's just, go, go, go. And so I think that there's going to be rude awakening at some point for that group of people. But I also think that the media is ... I hate blaming things on the media, it's so easy, but I mean, all the stories are about, raising money. And raising money is not a new story, saying I can't do this, we're not generating enough revenue to support our business ourselves. So we have to go out and raise a bunch of money.

Jason Fried: 20:51 I don't know why that's a story. Maybe it should be a story. If you've done something with that money, perhaps, and turned it into something bigger and better. And sustainable, that's a story. But there's stories about raising money everywhere all the time now. And it seems like it's inseparable to talk about business more like making products, and building a big business just seems like they're the same thing. And they're not the same thing. You can build products and build a nice, small business. But for a lot of people, that just doesn't seem like it's enough. And I think it's unfortunate that that's the trend. So we'll see what happens over time. What do you think what, from your perspective, do you think it's getting better? Or worse? Or do you think it's not even an issue or?

Matt H: 21:25 Yeah, well, having been in the industry and been working where I am for not very long, I don't have that thing to compare to, to when a time where it wasn't like that. So for me, it's hard to judge that where there's sort of the progress of how things are going there. But it's interesting to think about, because when I was in high school, I read a bunch of articles, and I was interested in a large degree with what's going on in tech. And I didn't really understand the finance piece of it. And so when I was reading these things, I would see these headlines of people saying, X company raised $35 million, let's say, in whatever round. And I thought, again, and having any idea how it worked, I was like, "Oh, these people just made $35 million." It was like, oh, they're, they're rich now. They've made that money.

Matt H: 22:08 So I think that in itself, and again, I don't know if I'm an outlier there or not. But it's sort of that mindset of that's what success is. And that's what you should be striving towards is not a healthy environment. I don't think.

Jason Fried: 22:20 I agree. It does seem that it's easy to think that, that you raise money, meaning, now you've got that, that you've earned it and you could close up shop, and now you're over 35 million or whatever. That money is actually in a sense that money is debt. I mean, you don't have to pay it back in almost all those cases, but you do have to do something. Now, the whole aim is to turn that money, which is someone else's money into a lot more money for those other people. And so you're obligated now to do that. It's not cash in your pocket. It's an obligation.

Matt H: 22:51 Yeah well, and it's step one, as opposed to the final goal. That's what I was confused about maybe was that, there's a lot more that's the start of your journey. If that's the way that you decide to even go with your journey with entrepreneurship through your writing, you've mentioned a few times and talked a lot about the fact that that's not necessarily the way to go in a lot of cases, that just to take money just for the taking money.

Jason Fried: 23:12 One other thing I want to quickly add, I'm sorry, just real quick, one other thing I want to add is, I think what's also happened. And I think it's important for employees to ask themselves this, as well, wherever they work, which is are you working for a business, a company? Or are you working for a financial instrument? I think a lot of businesses, a lot of companies these days in the tech world have become financial instruments, they only exist to be bought or sold kind of like alone or a bond or anything like, they're traded, basically. And someone thinks they're getting into lower value then someone else who thinks they're getting a higher value. And it's just like a financial deal. Versus actually like making something and caring about the customers you have and caring about the employees you have and that sort of thing. So I think there are businesses, there's companies, I think that's one spectrum, then there's financial instruments. And a lot of businesses these days, especially raise a bunch of money right up front. They're financial instruments, they're not companies in most cases.

Matt H: 24:02 Yeah, it's interesting to think about it that way. And I haven't heard it really framed in that way before but it does make sense, especially if there's a clear exit strategy for the founders. I've even seen companies that that's been communicated like, we're built to sell, I guess. So I wanted to talk to you, because you've been so outspoken about a lot of different issues, and so public with your writing and things like that. And when I'm reading these things, and for the listener, I'm a huge fan, and I been following you for a long time. So it's been a pleasure to be able to talk with you here. And I feel a little bit like, I can't really understand how I got here. But anyways, when I'm reading your stuff, it seems like it's so obvious and so straightforward and so simple, and I think that's why a lot of people are attracted to what you write about.

Matt H: 24:41 Why do you think you're an outlier here, in the way that you've communicated publicly and built the business? And it seems like you're still an outlier, even though it's been shown through your work with Basecamp, and you personally, that this works, this system works, and it might be harder to do it the way that you're doing it, but it works. So why is it that not many other companies are building their businesses like you've built yours?

Jason Fried: 25:00 Well, to be honest, it's baffling. Well, actually, let me step back. That's kind of unfair. In fact, we are not the outliers, we are as mainstream as it gets when it comes to business. 99% of all businesses are just like ours, which is that we need to make more money than we spend, we need to be responsible with our money, we need generate our money through selling things to customers and taking good care of them. The dry cleaner on the corner, they have to make more money than they spend, or they go out of business. The pizzeria on the corner, they have to make more money than they spend or they go out of business. Same with us, we have to make more money than we spend or we go out of business. We're as simple as it gets in terms of how companies run. And this is how almost every company in the world is run. Venture backed companies are the extreme exception.

Jason Fried: 25:42 So it's funny, because in our industry, it seems like we're outliers. But actually, if you zoom out further and to say like, let's forget tech industry, let's talk about business, where's its boring as it gets? So that's kind of how I would actually answer that. But I am surprised that more people in our industry don't see that. I think it's because the allure of becoming the billionaire or whatever is it's appealing, I get that. When everyone's running around, especially when people live in San Francisco, and they see so much wealth and money in terms of tech people and whatever, and this company has minted a thousand millionaires or whatever, I get it, I get why you want to be part of that, of course, I understand that. But it's such an outlier, really, and if you have a broader perspective, you realize it's an extreme outlier. And you're probably better off getting in with a company that's going to be around and you're going to have a good job and have reasonable hours and be able to have a life as well. I think that's the biggest thing.

Jason Fried: 26:34 I also think there's a lot of quiet companies like ours in our industry that just don't talk about it, because they don't need to, they're just doing their own thing. And they don't need to make a point. They don't need to prove themselves. They're just out there generating more revenue than they spend. And they're taking home salaries that are supporting their family and providing salaries for other families and just doing their thing day to day, just like you don't hear the pizzeria in the corner bragging about how they work and how they're structured. They just do their job. I think there's a lot of that going on as well.

Matt H: 27:05 You started this early on and it appears so why did you and David decide to go this route with it and be more vocal about the things that you dislike within the industry and talk about your failures. So why was that decision made?

Jason Fried: 27:18 Well, there's a number of reasons. Number one, we don't do traditional marketing in a traditional sense. For us, being outspoken has always been a way to be noticed. And to get our point across and to be heard and to be discussed and everything we say, we say because we believe that we don't say it to get a response. But we know that if we don't hold back, it's typically good for business, let's say. But also I feel like we have a responsibility to share especially in an industry that is apparently so opposite our point of view, at least the part of it that gets attention. Like I said, there's probably lots and lots of companies like ours in the world, most people are like us in terms of business owners. But in our industry it doesn't seem that way.

Jason Fried: 27:54 We feel like it's really important to be the counter point. Because the point is pretty obvious, everyone knows what the point is, in our industry. Everyone starts raising money and getting being growing as big as they can and having power. So who's the counter point? Well, someone's got to stand up for that, and show people that there's another way and we strongly believe in it. So we'd like to share we'd like to right, we like to talk and teach and share examples of how we do things. It's a combination of things, I would say. But it goes back to the early days of the company, which is like if we're going to talk about something amongst ourselves, why not just talk about it for anyone to listen, anyone to listen in. And also, if we've learned something, I think people have responsibility to share what they've learned. Some people are obviously more comfortable sharing it than others, we're pretty comfortable sharing what we've learned. And that's just sort of how that goes and why we continue to do it.

Jason Fried: 28:37 This latest thing we put out, Shape Up people have been asking us for years about how we work, specifically how we work. And we've put together blog posts, we've done conferences and workshops and stuff, but we never put together, or it's been a long time since we put together something as detailed as this. The last time was getting real, which was back in 2006. It was much more broad strokes. This is a really detail oriented, it is exactly how we decide to work and build features and build products and stuff. Part of it too, is just like we're asked all the time about it. And we might as well put it together in a format that other people can take away and learn from and we don't have to give the same answers over and over, we can say here, "Here's this thing, check it out. And this is actually a better answer than we would ever be able to give you right on the spot."

Matt H: 29:18 Yeah. And it probably has the added benefit as well of bringing great people within the Basecamp sort of umbrella and getting people excited about Basecamp in general. And I think that was showcased with the latest hiring that you just did that the amount of people that everyone looked like they responded was pretty phenomenal. And the culture piece of Remote Work, especially. I've talked to a lot of people about what culture is and how to build a culture and hear a lot of different things. So I was wondering if, and it doesn't look like you've written anything about this specifically, you did have a piece on culture and Rework, but you didn't really expand as much on it. Well, first, how do you build a culture? In your opinion. Is that even the right way to think about it? Has your opinion changed seeing as you are a distributed team, when it comes to culture?

Jason Fried: 30:05 I think first off, you have values, and then you try to live by those values. But ultimately, culture is not something you build or create. It's a byproduct. I think culture is a byproduct of consistent behavior. And here we go with the word consistent again, but consistent in terms of let's call it the last few years, that level of consistency, not forever. But basically, what are you doing over and over and over again, because that's ultimately what your culture is. So if you say that you do one thing, but you actually do something else, the culture is based on what you do not what you say. And I think that that's where people often get culture wrong is they put things up on the wall, and they profess to believe one thing or whatever. But that's not actually how it is.

Jason Fried: 30:45 And I'm sure there's things about our company that are like that too, where we talk about being calm and keeping things under control. And I'm certain and I know, in fact, there's moments when that's not true. So if that's not true, all the time then our culture is not one of calm. If it's not true occasionally, then our culture is probably still one of calm, but with some blips here and there. And so it's just about like a trailing, it's almost like a 50 day moving average. But let's call it like a two year moving average. That's really what your culture is.

Jason Fried: 31:10 We're thoughtful about our values. And we're thoughtful about reinforcing those values, and values, I guess, change over time, but fundamentally, a lot of them are pretty similar or have been for a long time. But keeping the company as small as possible, keeping teams small, not having meetings, making sure everyone's days are basically full eight hours of themselves. That kind of stuff. And of course, some of those are more specific than values more broadly defined. But basically letting people run their own day having a full day to themselves. That's the value, we believe that's important to have people be able to do that if we want them to only have to work eight hour days or 40 hour weeks. You can't expect someone to work 40 hour weeks if you take half their day away from them, and then expect them to get 40 hours worth of work done in 20 hours. That's just that's not reasonable. So being reasonable and being honest about this stuff is important to us.

Jason Fried: 31:57 Anyway, I think culture basically is the body part of a consistent behavior, it changes over time and as you change in size, it changes as well. And also as your makeup changes. To your point about remote, we've primarily always been a majority remote company. We have about 13, or 14 people in Chicago and the rest, we have about 54 people in the company that works. So the rest of the other 40 or so are spread out across 35 cities or so. We've always been majority remote. So that hasn't really changed for us so much. But there's a little bit that has changed in terms of the actual remote used to be just within the United States. And now it's Canada and Europe and Asia and Australia. There's people and now South America as well, we have people kind of all over the world. So there's some cultural changes that come from that and just managing time zones and some of that stuff and expectations around when someone's going to get back to you and who should be working together. There needs to be enough overlap and some of that stuff. But that's more about a way of working and less about like actual culture.

Jason Fried: 32:52 And hopefully that somewhere in that long, rambling answer, I gave you something that that makes sense. But that's that's how we think about it. I would say another chance for us is like we put together actually a physical handbook. Well, it's a virtual, it's typed, it's text, something permanent. But we wrote a handbook recently, we've been editing it and modifying it over time, but just something we didn't have up until just a few years ago. And we didn't have it because we didn't feel like we needed it, when we were smaller. But also we probably did need it even though we didn't feel like we did. Once we got to a certain size, it was important to codify some ways in which we work in some of the important values that we have. That had been like an oral tradition, basically. And we just felt like it was time to write it down. So everybody knew where it was and knew where to find it.

Jason Fried: 33:30 And we also made it public, which is part of who we are as well, our employee handbook is completely public. If you search for Basecamp employee handbook, you'll find it on Google it's hosted on GitHub. And it's ever changing. And so we want to make sure that how we act in private is how we act in public and that the public essentially can hold us to that. And everyone can hold us to that by seeing what we say, and making sure we do what we say that sort of thing.

Matt H: 33:55 The holding you to that is one that I'm sure is paid off for you as a company and just to make you and your team better by exposing what it is that you believe into the broader public and seeing you know what the response is. But when you do that, and when you've come up with something within your team that you think is important and relevant and put it out there, do you pay attention to the response at all? Or is that something you look at as in just for other people's benefit?

Jason Fried: 34:16 I think it's impossible to avoid paying attention to the response. But I don't get in arguments. I think I used to get in arguments. But I've sort of realized I'm not interested in trying to convince anybody of anything, I'll put something out there to hopefully maybe change their mind or give them a new ... Actually, I shouldn't say that I don't want to do that mind changing, I can't do the mind changing, there's no such thing. You can't change someone else's mind, what you can do is put information out there. Hopefully in a way that's clear enough that can get to somebody and then they can think it through if they're interested in thinking about it and curious and motivated to think about it. If they're struggling with the way they do things, they might be more open, more motivated to change something about the way they do things and put it out there.

Jason Fried: 34:51 Probably earlier in my career I used to probably fight more and argue more with people. I don't see the point. And occasionally, an argument still bubbles up to of me and I find myself regretting it the next morning. So yeah, I'm aware of the response to things but I don't go, "These seven people they don't get it, I'm going to convert them I'm going to change their minds by arguing better than they are." It's not worth it. It's also not possible. It's not worth the energy. So yeah, I think that's the extent of it. To be honest, I kind of wish that like for example, on Twitter, I don't like how anyone can get in your face, basically, by just mentioning, then get in your feed. So I tend not to read my timeline anymore on Twitter, because ... First of all, it's a terrible medium to even try to argue anything. I use it more for like publishing ideas and less about really going back and forth with people about them. Even though I do occasionally. But I just try to avoid that impulse. But of course, if you just pay attention at all, you're sort of aware of how things are received.

Matt H: 35:43 So just on the line of remote work for a second, I know then remiss if I didn't talk a little bit more about remote work with you especially, seeing that this is a remote work podcast. I know that you guys have been doing the remote work thing for so long and you were one of the first movers there and really vocal about the benefits. But how do you fight against those negative things that come along with remote work in terms of isolation and the communication piece of it? Obviously, you guys are experts on that area with your Basecamp. But how have you learned to cope with some of the negative components of remote work? And one of the big ones being isolation within your team.

Jason Fried: 36:18 It's a challenge that we still battle or struggle with. I don't like using military terms, we wrote that in our last book, people used all these military terms like battle and conquer and everyone was like, "Whoa, slow down on that." So we struggle with it too. And I think it's natural, I don't think it will ever go away for people. I mean, some people really truly like to be alone all day, and just focus on their work. And then when they're done with work they'll be with whoever they want to be. So some people really excel there. But most people need some more human interaction and not just virtual. So we try to pay more attention to that, we've been paying more attention to that recently than we have in the past, a few employees have brought it up.

Jason Fried: 36:57 And so I think the best we can do is we do have a few in-person meetups during the year, we try and do more video conferencing than we did in the past. Even though it's not the same, it's certainly better than texts for a lot of people just to kind of feel the connection. But also being willing to listen and to acknowledge the fact that remote work can be very isolating. It informs the hiring process, let's say. So I think we're a little bit more careful about making sure that the people we hire remotely, are really well prepared for that kind of work. Some people who've never done it before, of course, there's a first time for everything, and you got to give people a chance to do something for the first time. But I think we're a little bit more careful about really asking those kinds of questions about, how do you feel about that? Do you really get a lot of energy from being in a physical office space with others?

Jason Fried: 37:39 Just trying to understand them a little bit more, because I don't want to put them in a bad situation. And then certainly they don't want to be in a bad situation. Some people are willing to give it a shot, and they're totally able to do it, but others are not. So just being more careful about it, rather than assuming anyone can do it. It's about can you thrive in it. I think that's the more interesting question. But we want to find people who can thrive in it, not just put up with it. So yeah, it's just challenging, acknowledging it's challenging figuring out some ways that different people deal with it. Sometimes it's not just about seeing their co-workers, but just about seeing other humans. So hey, if you want to see other humans, here are some ways to do that. If you need to see your co workers, maybe we can do more video stuff, maybe you can come to Chicago a couple more times a year, if you feel like that might be a little bit more helpful, hey, there's someone else that works for us nearby, maybe once a month, you guys could hang out for a few days. I don't know, there's a variety of different ways to do it. But you have to be conscious of it and not assume that everyone's going to thrive in that environment.

Jason Fried: 38:27 We recently had someone who left, she left for a couple other reasons. But one of the reasons she left was she was surprised she'd worked remotely before, but not truly remotely. She worked in a remote office of a company that had their headquarters in another city. But there was other people that she worked with physically. And she was a little bit surprised by how isolating it was just to work from home by herself. That was just kind of a little bit of a shock for her. It's good to hear that because it's true, it's true. It is a shock, it can be a shock. And people who advocate remote working shouldn't be standing out there going like, this is the best thing in the world and it's for everybody. I do believe most jobs can be done remotely. But a job is not a person, it's a matter of can people thrive in that environment?

Matt H: 39:07 And this might be too broad of a question, but I'm going to ask anyways. What does remote work as a concept as a phenomenon go from here? Do you think that this continues on in the trajectory that it is and it just keeps growing and growing? Or as people get involved and learn more about it does the office become more of a important component of it? And what do you think the factors there, when it comes to remote work?

Jason Fried: 39:28 I think it's going to ebb and flow. I mean, every once in a while you hear about some big company that used to be remote that pulled everyone back in. And then that's the big news story for a while, which scares everyone away from remote work. And then you hear about companies like Stripe now is opening a new office, but that office is remote. So that gives people hope, again, it kind of goes back and forth. And then we've been big advocates and you guys are on the job board, that's We Work Remotely, which is a big deal for remote workers and Mac community. So I think it ebbs and it flows and I think it'll probably continue to do that. But it's getting more expensive to be in a lot of places, like Silicon Valley's just extreme cost of living there. And in New York, it's incredibly high.

Jason Fried: 40:04 And at some point, some companies are going to go, I just can't get enough people to live here and work here, and there's great people who are elsewhere, why would I want to close myself off to hiring great people, just because they don't live near me, that doesn't make any sense. Or some people might work for these companies and go, "Look, I'm working really hard. I'm getting great salary, but I can't save a penny because my costs are just out of control. And I'm not living exorbitantly, cost of living is too high, I need to move." And they're going to start losing people. And so I think that, that's going to open up more companies to realize that there are other parts of the world or the country or the state or wherever you are, there are great people everywhere. There are great opportunities to hire those people and for those people to thrive. And not everybody needs to be in the same room.

Jason Fried: 40:46 So I think more and more companies will experiment, some are going to make it work and some are not. I think the way in which they try to experiment has a lot to do with it. For example, if you're 50 people locally, and you try to hire your first remote employee, so you're 51 and 50 are local and one is remote. That's probably not going to work. If you take your 50 people and say, "We want to start to consider hiring remotely. So over the next six months, we want to basically have a virtual remote company and that even though we're all together here, maybe three days a week or one day a week, we're going to work from home and start to get used to working remotely." I think that's a better approach. So it's not just the concept. It's how you approach it that has a lot to do with whether or not it works.

Jason Fried: 41:22 I'm hopeful that more and more companies begin to experiment with it. But certainly there will be some high profile flameouts, and then that'll scare some people away. I also think it's probably generational, and maybe over the next 10, 20 years more people will be more open to it. So yeah, that's my general take.

Matt H: 41:39 I've also heard that companies or investors tend to not like the idea of hiring remote workforce. And I don't know exactly what the reason is there. And maybe it's because this is an investment for them and there's too much of a risk potentially with the idea of having a distributed workforce, and they don't know about it, maybe it's a knowledge thing. But I have heard that as a potential blocker for a lot of founders for starting remote companies or starting companies is that their backers don't want them to hire remote workers. But it's interesting too, because I mean, if you look at a lot of the balance sheets of remote companies is a lot stronger, because they don't have that massive, rent expenditure on their P&L. But anyways, that's an interesting counterpoint, I think, too, is that maybe it's just fear, and maybe the work that you guys are doing to be more vocal about the positive aspects of it. And the fact that it works, maybe that's going to be encouraging for people who are founding companies moving forward.

Jason Fried: 42:22 Yeah, I can understand why it's scary. If you've done something your whole life one way, and then all of a sudden, there's this new way, it's naturally human reaction to be like, "Whoa, wait a second, I don't trust that way. Or I don't know that way, I don't believe that way. Or Why should I do that? Let them do that." I get it, totally just a human thing. I think the best way to do that is just to try it. And that's the thing, I think the scary thing is hiring a remote employee first time. But if you have local employees just make them remote employees for one day a week, one day a month even, just 12 times a year, let people work from home. Just kind of get used to it go, you know what, the sky is not falling, the company is not going out of business. In fact, you know what, people seem to like this, you know what people are getting more work done and there's fewer distractions and the whole thing.

Jason Fried: 43:03 I think anyone can experiment with this without having to go out and hire somebody, and then try to feel like you have to learn everything on the fly with someone new. And then maybe if that doesn't work out, then you're like, "Well, why would I want to try that again? It just totally miserably failed, I hired someone remotely, it didn't work. This doesn't work." I mean, I think get a step into it a little bit differently. And I think then you'll have some confidence and realize that, hey, this could work. And then maybe six months or a year from now, you're ready to maybe hire that first remote employee after you basically simulated a remote workforce for a while. That's the approach I would take, if you want to work your way into it.

Matt H: 43:35 Yeah, I also think that the technology itself will get better. And I know there's a few companies out there that are working on different products, like physical products, to make it as if you're standing or sitting in the room with them. I think the technology will get better, and there'll be companies and services that pop up around remote work, that'll just make it easier. So that's a big piece of it, I think, too, is just there's going to be more things to support the idea of a distributed team.

Jason Fried: 43:56 I hope so although I will say that I think there's a danger in trying to simulate the worst parts of an office environment, which is it's so easy to pull people into meetings, it's so easy to stop people from doing what they're doing. When you're remote, it's a little bit easier to hide from those distractions. Not always, but a little bit easier. And I think that that's actually an advantage. I'm worried that it's going to become like, you're basically there. I don't think you want everyone to be there. I think that's part of the problem. Everyone's so close, it's too easy to be pulled away from your work. Anyway, I think there needs to be a balance.

Jason Fried: 44:28 And certainly I'm excited to see what technology can do. Video conferencing has been a big deal, so what's the next level there? Is it better or worse? I don't know. Sometimes it's worse when it's more physical. It's better when it's clearly like just a video conference versus the expectation that you're actually fake sitting in a room kind of thing. But who knows? We'll see how it all shakes out. I'm glad people are at least working on the problem or not even the problem working on the concerns seeing there's something to be done there.

Matt H: 44:52 Yeah, for sure. Well, Jason, you've been so generous with your time and want to be cognizant of it. I do have a couple more closing questions here for you. The first one is actually more specific to you as an individual. And just because I know that you are a watch guy and you like watches. So if you were to wear one watch for the rest of your life, what watch would that be?

Jason Fried: 45:12 Well, I can tell you what my favorite watch is. I don't know if I'd want to wear forever. But let's say my favorite watch is a 1957 Rolex Milgauss 6541 is the model number. That's my favorite overall watch design ever. If I own one, and I had to give away, let's say own 50 watches, and I had to give them all away. That's the one I would keep. Let's just say that.

Matt H: 45:33 So that is one that you already own? Or is that a dream watch?

Jason Fried: 45:35 I own one of those. I've had it for a while. It's one of my favorites. But it's not something I wear very often because it's funny, it's unfortunately become very valuable. And what I mean by unfortunate is, I'm afraid to wear it sometimes. And I don't like that, becomes irresponsible at some point to where things like that.

Matt H: 45:51 Got you. My next question is, if you weren't an entrepreneur, what would you be doing?

Jason Fried: 45:58 It's funny, I actually like not to be sometimes. Let's say I didn't have to worry about money or something like that. Let's just say that wasn't a concern. I would love to take up pottery, in a serious way. I would love just all day to get behind a wheel and throw pots all day, I think that would be an incredible thing. Either that or landscape architect or gardener kind of person. I just I love that as well. So those would be two things I would love to do.

Matt H: 46:26 Do you do those things already sort of in your spare time? Or is that not on the agenda quite yet?

Jason Fried: 46:31 The gardening and landscape architecture stuff? Yes. I mean, not the landscape architecture stuff as much. But I am involved in restoring a bunch of land that I own up in Wisconsin. So that's a really fun, long term, 10, 20, 30-year project. I'm involved with that. And then locally gardening in my house, I'm really into that. Pottery, I've taken a few lessons. And I know I love it. And I love ceramics, I love looking at buying certain ceramics and stuff. But I don't know how to do it, really. So that would be something I'd have to learn. I'd love to dedicate a year to becoming really good at that.

Matt H: 47:03 Fascinating. I know, I hear you on the gardening piece. gardening is one of my passions as well. And it's endlessly interesting. And I'm lucky enough to be able to do it where I am right now. So it's something that I love. Because it's not something that I can ever be distracted with a phone while doing.

Jason Fried: 47:15 Right. There's something about the soil and being close to it and the plants and the variety. It's just lovely. And it's so calming. I don't know, for me, it's Heaven, basically just to be out there in the garden.

Matt H: 47:25 Yeah, definitely. It definitely is. My last question here before I let you go, Jason is my favorite one. And it's actually kind of a riff off of the one that [Clare 00:47:33] asked everybody on her podcast. What is the best advice you've ever been given? And that can be in business or in life, but just what's the best advice you've ever been given?

Jason Fried: 47:41 Well, we've been mostly talking about business in this show, I'll just give you business advice. My dad gave me this. I don't know when. But long, long time ago. He said, "No one ever went broke making a profit." And that's probably my favorite business advice ever. Life advice, I to figure that over. But business advice clearly, that's it for me.

Matt H: 48:01 Well, maybe what we'll do is we'll shoot you an email afterwards and you can ponder the live advice well and we'll put that in the show notes.

Jason Fried: 48:07 Great.

Matt H: 48:07 Jason, again, thank you so much for coming on the show. We really appreciate it. I know that our listeners will definitely appreciate me being able to pick your brain and I have a whole bunch more questions for you. So maybe down the line, we'll be able to do another one. But before we go is there obviously we want people to check out Basecamp, we want people to follow you on Twitter and all the rest of that. But is there anything else, anywhere else you want to be sending people?

Jason Fried: 48:28 Yeah, the new book we just launched is called Shape Up. And then also we have our own podcast called Rework, the Rework podcast. It's at rework.fm. So R-E-W-O-R-K.fm. And we talk a lot about the things that we kind of talked about here at length on our own podcast. Please do check that out as well. Yeah, that's kind of it. Otherwise, socially, I'm only on Twitter. I don't do Facebook or Instagram. I'm on LinkedIn, but I don't really check it. So Twitter is probably the best way to publicly get a hold of me if you want to argue about something and I will not argue back.

Matt H: 49:01 Yeah, don't argue but definitely follow Jason. I know it's a great form of inspiration for us and for me specifically. So yeah, I'll definitely do that and we'll link to all that kind of stuff on the show notes, especially the newer book. And also, I didn't even mention that, it doesn't have to be crazy work. Great book as well.

Jason Fried: 49:15 Thank you.

Matt H: 49:16 We'll make sure we'll link out to that.

Jason Fried: 49:17 Cool.

Matt H: 49:18 Jason that thanks again. I appreciate it so much. And we'll talk again soon.

Jason Fried: 49:21 Yeah, anytime. Thanks so much. Bye.

Matt H: 49:25 Thanks so much again, for listening to the show. Be sure to check out weworkremotely.com for the latest remote jobs. And if you're looking to hire a remote worker, We Work Remotely is the fastest and easiest way to do so. As always, if you have someone that we should talk to, any advice you have, or if you'd like to advertise on the podcast, please reach out to us at podcast@weworkremotely.com. That's podcast@weworkremotely.com. Thanks so much again for listening and we'll talk to you next time.