Sherry interviews Jason Fried of Basecamp, about some of the ways his remote company helps team members connect with each other. They also discuss other topics including burnout, sleep, what does calm mean to him, and how he has maintained a long term business partnership.

Love this conversation? Check out Jason’s latest book. It Doesn’t Have to be Crazy at Work.

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Episode transcript:

Rob Walling:
In this week’s episode of ZenFounder, Sherry interviews none other than Jason Fried of Basecamp. It’s a really good interview. Sherry talks to Jason about all manner of things ranging from family life, to building a company slowly and deliberately. One thing that I really like about Jason is just how genuine he is. He really doesn’t have anything to hide. I met him for the first time in person at MicroConf just a few months ago. And I was struck by just how normal he is given his amazing success with Basecamp and his numerous New York Times bestsellers and everything he’s accomplished in his life. We just had a conversation about life, and about kids and family, and where we lived and just normal day to day things. And I liked that he was real and that carried on to the stage.

I hosted a moderated Q&A where I asked him questions about his history in growing Basecamp and what he thinks of bootstrapping today, and all kinds of stuff. And he just answered the questions. That sounds so simple, but so much of the time when you are around people who have had success, especially in certain circles, I’ll say startup circles are notorious for this. People are puffing up their chests and they’re saying things that make them look good, or they come up with this, you know, a theory so that they can name it after themselves or something. Or you see someone on a panel and you know that their business isn’t doing great and they’re saying all these things like they know everything. That’s not what MicroConf is about, and B, that’s not what Jason was about at all. He was just about talking from his experience, and that’s something that I really respect about him and others who I know who are successful, but they let their success talk for them. They don’t sit there and trumpet it themselves.

And so with that, let’s get started with the interview. I think you’ll enjoy it as much as I did.

Sherry Walling:
Welcome to the ZenFounder podcast. This is a place where we have conversations about mental health and entrepreneurship. We have a pretty broad conceptualization of what mental health means. Sometimes depression, anxiety, sometimes relationships or physical health. The goal here is to bring some calm into the crazy rollercoaster of ups and downs that is life for many entrepreneurs. I’m your host, I’m Dr. Sherry walling. I’m a clinical psychologist and an entrepreneur, married to an entrepreneur, live in the world of entrepreneurs, and I’m so pleased that you have joined us for this conversation.

Sherry Walling:
So, I gave a talk at a conference about a year ago and at the end of the conference people were sharing their take home and they were like, “What did you get out of these two days of content? And it made me feel good, but a number of people were like, “Sherry’s talk about sleep is the thing I’m going to take home from this $2,500 conference that I invested in for my business.” And I spent 20 minutes talking about the importance of sleep for having a sound mind that works well at work. And I know that’s something that you’ve spent, apparently, a lot of time thinking about, or you just knew intuitively, but what is the deal with sleep? Why is it so easy for people to rationalize cheating ourselves out of it?

Jason Fried:
Well, first the only reason I know anything about it, there’s two reasons… well, actually three reasons. One is, I have two young kids at home and when I was not getting sleep, like our kids sleep through the night now, so we’re okay, but when they weren’t, I was just a wreck. This is anecdotal. This is one person’s… But I know every parent deals with the same thing. You’re just a wreck. If you don’t get a good night’s sleep, you are a mess.

Jason Fried:
You’re impatient, you’re difficult to deal with, you can’t think straight, you can’t remember things well, you’re not a pleasure to be around, let’s say. So that’s true when you lack sleep. And then you start to think about this thing, start to sleep better and you see that your mood changes, and everything changes, and your abilities change, and you start to be more creative and more thoughtful and put together better sentences and the whole thing. So that’s another data point.

Jason Fried:
And then you read a book. I read this book called Why We Sleep, which is probably the most important book I read last year. And it’s long, but it’s wonderful. I think the guy’s name is Matthew Walker, who wrote it, and it goes deep into the science behind sleep. And it’s really amazing, because I’m always terrible with like, remembering scientific facts, you are significantly… Let’s say you’re at a significant disadvantage if you even get only six hours a night. So, most people think about sleep deprivation, like well, four hours, five hours. No, even at six, it’s six hours which is what most people actually end up getting, you are severely impaired. Creatively, your ability to reason, your reaction times, a whole slew of things go down the drain pretty quickly. It’s just amazing. It’s six hours.

Jason Fried:
So, you read that too, and on top of your own personal experience, and you read that and the science, you’re like, “I think sleep is incredibly important.” And then, the other point that he makes, which I think it’s really interesting is that evolutionarily you think we would have phased sleep out, because it puts you at such a risk, right?

Sherry Walling:
Sure.

Jason Fried:
You’re unconscious for a third of the day-

Sherry Walling:
While the bears and tigers are prowling, by the way, every week.

Jason Fried:
… Exactly. And so you’re like, “This should not have lasted if it wasn’t valuable.” But in fact, it’s so valuable that it’s worth basically being unconscious a third of the day for the pros so far outweigh the cons. So I think that’s another interesting point about it as well. But why do people… I mean, I just [crosstalk 00:05:53]

Sherry Walling:
Yes, I’m with you. The logic is there, the science is there, I think most like relatively well informed people are aware that they probably should sleep more. It’s one of the first things that I see founders, high performers, whoever, throw away when they feel-

Jason Fried:
I think they feel like it’s wasteful. They’re like, “Why should I spend a third of my day doing nothing? Like I’m productive, I need to be doing something. I need to be reading, I need to be watching a TV show, I need to be working, I need to be doing stuff. Why would I throw away this time, and in fact, other people are sleeping. So if I’m working while they’re sleeping, I’m going to get more done.” There’s this really perverse mentality around it.

Jason Fried:
The thing is that, typically, people who are sleep deprived don’t recognize it, but everyone else does. I mean, you recognize it when you’re really sleep deprived, like when you’re really flat out tired, but if you’re moderately sleep deprived, which is what a lot of people are, they don’t notice it. Just like maybe an alcoholic might not know they have a problem. It’s a similar thing. Everyone around them knows. Or an addict or whatever. Sometimes you do know, but most of the time, you may not. [inaudible 00:06:59], “It’s fine, I can handle it, I can handle it.” Everyone else knows you can’t handle it. So I think-

Sherry Walling:
… And it’s become so common.

Jason Fried:
… It’s become common. And it’s also become like, a badge of honor for people to say, “I’ll sleep when I’m dead,” or, “I only got three hours of sleep last night.” Why are you joking about that? Why are you joking about that in a positive way? You should be horrified, actually, about the fact that you’re unable to sleep. And you shouldn’t probably be driving, and you probably shouldn’t be making any key decisions, and you probably shouldn’t be managing other people, and you probably shouldn’t be interacting with other people if you’re like that far down on your battery, basically.

Jason Fried:
But yeah, I think it’s convenient. It’s an easy thing to eat into because it pushes back but not completely.

Sherry Walling:
Yeah. So, when someone starts working at Basecamp, how do you help them connect with the rest of the team? How does that happen?

Jason Fried:
Well, we’ve gotten better at this. We were bad at it for quite a while. One of the tricks, I’ll step back for a second. One of the tricks, one of the problems I should say that we have is that we’re remote company primarily. So, we have 54 people in the company, there’s a couple dozen of us, well, actually a dozen of us are still in Chicago. But most of the people work outside of Chicago. So if you’re brand new and you live in Tennessee and you start at Basecamp, normally you wouldn’t see anybody, you wouldn’t know anybody, it’s kind of really hard to get started that way. We used to just start people that way.

Jason Fried:
But now we bring people usually into Chicago, sometimes another city, but often in Chicago for a couple of weeks if possible, for the first two weeks. So you can get to know the people, get to know the team a little bit, get to know some people. And they’re also assigned a buddy essentially, who’s someone who they can ask any question of and look out for. And then we also typically, we use this product called know your company, which has now been renamed know your team. But there’s a really great feature called icebreakers. And when anyone joins the company, they’re asked to answer five questions. And the five questions are always the same. And they’re just social questions. And you’re free to say whatever you want, or not doing it all, of course. But whenever you answer them, they’re sent out via email to everybody else in the company, and then the person who sent them out, or who wrote them up and answer them actually gets back everyone else’s questions that they answered when they first joined the company.

Jason Fried:
So it’s a really nice way to quickly, just to set the table a little bit and go, “Here’s the people that are here, here’s some of the fundamental things.” Maybe I have this in common with this person, or that in common with this person, and then we just kind of slowly bring you in, and you always usually start working with the team of some sort, and so there’s just more video conferencing in the initial few weeks to put a face to the name and a face to the voices. It’s worked a lot better than before, we just threw people in the deep ends and figure it out, which was a big mistake of ours, we just hadn’t put any time into thinking it through.

Jason Fried:
And also, I should say, our support team really pioneered a lot of these ideas for us. They’ve been great at onboarding people when the rest of the company was not quite as good. So we follow their lead and do a lot of things that they do.

Sherry Walling:
I mean, one of the strengths, obviously, of what you all have put together is that it really protects people’s time to do their work, to be creative, to think, to engage with the tasks at hand. And as I was reading your book, which is fabulous, thank you, there were so many things about it, that I was like, “Oh, this is so good for the human mind.” But then the thing that I kept thinking in the back of my head is like, this sounds really isolating too.

Jason Fried:
It can be.

Sherry Walling:
So when you don’t have… meetings are, I appreciate, a great waste of time. But they’re also a great way for humans to see each other and connects together. So, yeah, you said it can be, it can be a little isolating.

Jason Fried:
It can be isolating, and that’s something we have to battle from time to time. We also do other things. So, there’s a feature in Basecamp 3 which is called automatic check ins. And automatic check ins will automatically ask questions of people on a regular basis. And then people write up their answers, and they’ll share back with the rest of the company. So, every Monday morning, Basecamp automatically ask everybody, “What did you do this weekend?”

Jason Fried:
Now, again, totally optional, because some people just don’t want to share their private life, fine, but a lot of people share pictures of their kids, or things they did, or concert they went to, or a show, or some Home Improvement Project they’re working on or whatever. And so every week, there’s this drip of what people’s lives are like because you don’t really get to see them, and in fact, in many ways, it actually brings you a lot closer than if you’re just in person with meetings because you wouldn’t really get to know the people necessarily. Get to know them in so some degree, but the fact that we’re like, actively asking this thing, like, “What you do this weekend?” Helps people see a little bit more into other people’s lives. And some people are very comfortable sharing, others not.

Jason Fried:
So we do that. We also once a month, Basecamp will ask everybody, “What have you been reading lately?” So people share books they’ve been reading, and they write up these nice little mini book reports. And just another good insight ans they’re like, “Hey, I don’t work with this person very often, but she just read the same book I’m reading, we have something to talk about.” Maybe I can ping her and say, “Hey, I’m really enjoying this book, that’s so cool that you’re reading it or whatever.” And you start to get to know people on a different level again. So, we’ve instituted a number of these automatic, recurring questions that are more on the social side of things.

Jason Fried:
We also do work side of things like, “What did you work on today? What are you planning on working on this week?” But we’ve layered in some social stuff, including, like, “Have you tried new recipes lately? Have you seen any movies movies lately, or what’s inspired you lately? Things like that. And you just begin to get a nice round picture of each person that’s kind of cool that way. That’s another thing we’re able to do.

Jason Fried:
We also do bring people into Chicago for a week, twice a year. So, twice a year, we fly the whole company into Chicago for like a week long meetup. And no, that’s only two weeks out of 52, but it’s nice because it’s pretty much primarily social. We all get dinner together, we all hang out together, we have guest speakers, people are free to do whatever they want. And it’s just another nice way to do the best we can given the fact that most people are scattered around the world.

Sherry Walling:
How do you make that Chicago time meaningful? Like, do you structure it? Is there a talk every morning, or is it kind of like a free for all? How do you balance work ish time and just hanging out?

Jason Fried:
Well, there’s always one talk scheduled on Monday morning, which is me and David, my business partner, we get sort of a state of the union and share some things we’re thinking about. If it’s a really important moment, we share some vision for the next year or wherever it might be. That always happens. And then we have basically a schedule inside Basecamp where anyone can post events saying like, “Hey, I’m going to be giving a talk on Wednesday at one o’clock on this thing I’m working on.” Or someone’s like, “I’m going to give the talk on skateboarding at 10 AM on Thursday. Anyone who wants to show up can show up.

Jason Fried:
So, people post their own talks on the schedule, and it’s totally up to whoever wants to show up. It’s all optional, except that first State of the Union speech, basically. We have lunch, share lunch every day, we have the company dinner on Tuesday night, we also do these things where I think it’s usually Wednesday morning, we do what we call employee recognition awards, basically, but it’s not managers, it’s peers celebrating each other. So, people get to nominate each other and say, like, “This person went above and beyond over the past six months.” Or, “I really appreciate the work this person does.” Or, “She’s doing this great, or he’s doing this great, and I don’t know if anyone’s noticed what they’re doing.”

Jason Fried:
So, they’re nominated and then we make these really nice wooden spheres, these kind of neat little things that we engrave and give to people. So people come up, they’ll nominate, we’ll make these awards, people will then come up and present to each other. And there’s usually like, a lot of hugs and some tears and stuff, it’s really a special moment actually.

Sherry Walling:
Pretty meaningful to people, it sounds like.

Jason Fried:
It is because we don’t all get together and then when we get together, like, it’s kind of like if you don’t get together with… if you haven’t seen a friend for three or four years, let’s just say a year, and you get together with them. That dinner, or hang out is very meaningful, more meaningful than if you were to get together every week. Because if you get together every week, it’s like, yeah, you’re going to get every week. But if I only get a chance once or twice a year to see somebody that I care about or that I put a lot of effort in with, it’s interesting how more meaningful these weeks become. We used to make them very more business focused, a lot more business focused, and then we dialed that back, because we realized what people really want for this week is a little bit of business, but then mostly social, because that’s what they don’t get enough of the rest of the year.

Jason Fried:
So, we’ve modified that. There’s also like, some people who live in Chicago will take people on little tours, or they’ll say, “Hey, come to my yoga studio with me,” or whatever, and they’ll kind of play host, which is nice. And that sort of thing.

Jason Fried:
One of the things actually we’ve done recently is, so we do this big company dinner on Tuesday nights, but you have dinner 54 people around a restaurant or something, it’s just hard to see everyone and really talk to everyone when there’s 54 people. So now we do, I think it’s Monday nights, there is… actually maybe it’s Wednesday. There’s small groups that you can sign up for, small group dinners of three or four people. And then there’s also Ladies Night, like all the women in the company have organized Ladies Night. I think that’s Monday night. So, they do something. There’s just like different groups decide to do different things with each other. And it’s just a really nice weekend.

Jason Fried:
But I’ll say this, though, we’re mostly introverted company, and by Friday, everyone is completely [inaudible 00:16:01].

Sherry Walling:
It’s like, “I’ll see you again in six months.” It’s enough.

Jason Fried:
Yeah, basically. They’re totally cashed out. But it’s a really important week, in our section the next one’s coming up in a couple of weeks. So, looking forward to that.

Sherry Walling:
Oh, awesome. Cool. Have you observed either in yourself or in people that you work with at Basecamp, have people struggled with burnout?

Jason Fried:
Yeah. I think everyone struggles with it from time to time. Sometimes, there’s different reasons for it. Sometimes someone’s sort of at the end of their road in terms of this particular job, or like the actual job they’re doing… the work they’re doing is no longer motivating them. It’s not like they need to go to another company, it’s that they just want out of design, or out of programming, or out of-

Sherry Walling:
Doing that set of tasks all the time.

Jason Fried:
… Yes. So, sometimes there’s that. Other times there’s people who care a little bit too much about the work, and they put in a little bit too much time, and nobody notices until it’s a little bit too late. And then we notice that they’re definitely acting like they’re burned out where their answers are shorter, they’re not maybe as pleasant as they used to be, or they’re not as patient or there’s something, something’s up and will say, “Hey, what’s going on? Notice this, notice that.” And hopefully we can catch that and give people extra time off, or get them some help, or figure out what the root causes are.

Jason Fried:
So, actually, I’ll step back. We have a sabbatical program. So every three years, everybody in the company gets a one month paid sabbatical. And one of the reasons we did this is because one of our employees was having some challenges around mental health and burnout and that sort of thing. This is a number of years ago, and we gave this employee some like, about a month to help, get sorted out, we offered some help, et cetera. And I won’t go beyond that. It’s personal. It really worked, it really was an important thing. And we realized… we noticed this about him, and he noticed this about himself. But perhaps there’s other people who aren’t bringing this up, or we don’t notice, like, let’s institute this to make sure everyone gets at least a month off every three years. And we also have a generous vacation policy.

Jason Fried:
That seem to really help quite a bit that there’s this release for everybody. But primarily what we try to do, as best we can, is maintain a calm culture. Without unreasonable expectations. We believe eight hours is enough time per day, and 40 hours is enough time per week. We shouldn’t be working on the weekends, and we shouldn’t be working at night. And there’s no ridiculous deadlines that are impossible to meet. And that everybody does have the power to cut back on the work that’s required. For example, if something’s due Friday, and it’s Tuesday, and it just doesn’t look like it’s going to get done, they have the power to say, “I’m going to do less of this work” I’m going to cut this back, versus either, like pull all nighters or push deadlines. Just like, if it’s too much work for whatever reason, come up with a simpler version of it, we’re okay with that. So, people have a lot of control over the limits of the work itself.

Jason Fried:
We also recently finally put someone in charge of people ops or HR, we’ve never really had anyone in a formal position in that role, and now we do. And she’s been wonderful helping people, she’s meeting with people more frequently. We still have this attitude, which is like, if there’s a problem, let us know. Which is a terrible attitude because most people don’t let you know, we had to mature there’s as an organization. And now we do frequent one on ones with everybody. There’s now a place to go. It used to be people would come to me or David, but coming to the owners is, it’s never a welcoming, comforting thing to do. Even if you say, “My door is always open and I’m always accessible.” It doesn’t matter. Like there’s-

Sherry Walling:
[crosstalk 00:19:26] your book, that’s a [inaudible 00:19:27] out?

Jason Fried:
Yeah, it is. It’s a total cope out. My door is always open as a cope out because there’s inherently a power dynamic here and who wants to go to the owner and complain about something. I totally get that.

Sherry Walling:
Have an issue with a co worker. Confess that there have postpartum depression. I mean, yeah, all those things get real tricky when there’s a power dynamic.

Jason Fried:
Absolutely. It doesn’t matter like how welcoming we might be, it doesn’t matter. It just doesn’t work. So, we finally have someone now in charge so a lot of people are going to her and she’s getting to give them a lot of help. There’s a lot more things were now internally to help people with those issues. But we had to grow into that, we didn’t really realize it was a problem. It’s not a deep problem for us but there’s enough of a problem when you’re 54 people, there’s certainly always going to be people who need a hand there. And now we formalize that. So I think that’s good.

Jason Fried:
And we’re still always learning about new opportunities. In fact, like we just had a new benefit recently, I think our health insurance, it’s either a health insurance or life insurance benefit has a like a mental health consulting phone number, at least, that you can call and get some help, if you don’t want to ask someone in the company because even though we have someone dedicated to that, there’s still a stigma sometimes talking about this. If someone who reports to me and they don’t maybe want someone to know, so there’s now some outside help for people can get that’s included with their benefits package.

Sherry Walling:
Do you all have, over conversations about depression, anxiety, things that fall under that mental health umbrella?

Jason Fried:
We’re beginning to. We actually have a speaker, I believe, at this next meetup who’s going to be talking about some of those things. We also have a, we have one of our Basecamp projects set up that’s called the Care Camp, which is set up by like, it’s a volunteer thing internally where people share their own methods for self care. And people can ask questions about that. And whoever is comfortable sharing is free to share. It’s been actually a really nice little corner of the company for people to go to and get help from one another if they’re struggling with something. Now, that’s not private, it’s not private because it’s open to everybody in the company. So, it wouldn’t be a place for you to go where you need to say something privately, but it’s a place to go where you want to ask for help publicly from your co workers? Or, “Hey, how does anyone cope with this? Or how do you deal with this kind of stress, or what’s your routine around breathing?” Whatever it might be, there’s no place for that.

Jason Fried:
So, people are talking about that internally, and there’s a place to turn. And we are bringing in some more people to talk about this across the company. But I think it’s super important. I don’t think you could ever really do enough. And we’re beginning to do more and I think we’ll do more and more and more in return. [crosstalk 00:21:59] one other thing… Sorry, I keep thinking as you think about these. We actually also instituted something where people used to be able to take, you’d always see people taking sick leave, or like, personal time for an illness or something, but that kind of rarely historically extended to mental illness, it was always like, well, I’m in the hospital for two weeks, because I broke my arm or whatever, you wouldn’t be in the hospital for that, but whatever.

Jason Fried:
And it was always like, well, of course, you’re in the hospital, take whatever time you need to get well or wherever it is, but if it was a mental health issue, that wasn’t really seen as as equivalent, in a sense. It was just seen as like, well, deal with it, or that’s your own time to figure that stuff out, but-

Sherry Walling:
Great. Stop being sad, get back to work now.

Jason Fried:
… Right. And we’ve changed that now. So now, any health time you need off for whatever, like it extends to any kind of health issue, mental, physical, whatever it might be. So, we’ve made that more available too. So, we’re learning and we’re doing better and better here over time.

Sherry Walling:
Yeah. I like even something like Care Camp, which is sort of crowdsourcing wisdom, and it’s de stigmatizing, and it’s de isolating the conversation from something that happens in the corners and the shadowy private, to something that you can say like, “Hey, I’m having trouble managing my anxiety. How do you all do it?”

Jason Fried:
Totally. Yeah. And of course, if you need professional help, you go somewhere else. But a lot of the times, it’s like, it is a good place to start at least. Like, “I’m finding myself having a hard time with this or that, what have you done? What have you done?” And people are so helpful. It’s amazing how helpful people are when you just admit that you need a little bit of help. I mean, everyone wants to help in that case, in that situation. So, it’s been a very, very nice thing to have in the company.

Sherry Walling:
Why is calm so important to you?

Jason Fried:
I don’t like things to be hectic around me personally, just in general. So, there’s a little bit of selfishness, I would say. I just don’t like being in that kind of [crosstalk 00:23:56] environment. Yeah, I like it that way. But mostly I think it’s important because it basically says like, we don’t need to rush through these things. What is the rush? And I’d like people to be in a good mental state and physical state and not have unreasonable expectations beating down on them when they make decisions, and when we have conversations. If you’re always high, strong, and things are always like, impossible deadlines, we call them dreadlines. If people are, the expectations are completely unreasonable, the expectations of growth, the expectations of getting things done on deadlines that are impossible, hitting targets that are completely unreasonable, it’s not a pleasant place to be. Everyone’s nervous, everyone’s scared, everyone feels like they’re going to be fired all the time. Who wants to just go into that environment every single day?

Jason Fried:
I mean, there’s certainly moments in any company, or when there’s an emergency, or there’s something truly urgent, of course, like, then you step up, and you may have to put in a couple hours here, or you may have to be more vigilant here or there. But that shouldn’t be the constant state of things. I mean, I think when the constant state of things is this idea that it’s crazy work all the time, and then I’m constantly busy, and I can’t get anything done, and I’m in meetings all day, but I’m still expected to do work. And so it’s eating into my personal life, and I’ve no weekends, it’s like, that becomes the norm. You’re just going to lose people, you’re probably not going to do great work. If people aren’t sleeping, they’re not going to be really creative and thoughtful, and they’re not going to be patient with one another, and they’re not going to listen. They tend to just to talk.

Jason Fried:
So, I think you get a whole bunch of benefits from it. Plus, it just feels like a better place to be. I know some people like the sort of boiler room, war room style thing-

Sherry Walling:
The adrenaline.

Jason Fried:
… The adrenaline. I get that. I mean, I think adrenaline is supposed to be something that you get occasionally. Fear of flight kind of situation. Like it shouldn’t be, I don’t think it should be the norm every day you walk into a hot house or just out of control. Doesn’t seem right to me.

Jason Fried:
Also, the other thing I’ll say is that, we’ve been in business for 20 years, this is our 20th year, and we want to build a sustainable company that will be your for a long time. And I think if you’re in a different path, if you’re on a different path, where you maybe go raise a bunch of money, and you’re trying to like hit it big in five years, or go bust like, in some ways, I can understand why some people would feel like you need to run as hard as you can, because it’s almost going to be over anyway. For us it’s a long, long run. It’s a marathon. I don’t want to throw the analogies in there.

Jason Fried:
But like, it’s a long thing, we hope to be in business 30, 40, 50 years, I don’t know if we can. And so if you do that you have to maintain, or you have to practice a certain discipline that you can maintain that’s sustainable, that won’t burn you out, won’t burn out your employees, because it’s hard to find good people, it’s expensive to hire new people. So, I can layer all these things into why I think it’s important to be calm.

Sherry Walling:
What does calm feel like to you in your body? And I ask because I talk with a lot of people and they forget what it feels like to be calm. Like they’ve lost the physiological framework of that.

Jason Fried:
Yeah, the number one thing is having an open day ahead of me. For example, at Basecamp, we don’t have shared calendars. So, I can’t see what everyone else is doing during the given day in terms of time blocks, and they can’t see what I’m doing. And everyone has a full eight hours to themselves by default on any given day. To me that is the beginning of calm. Because if your day is chunked up so much that you can’t even be by yourself to think for an hour or two, I think it’s very hard to maintain a sense of calm. So, for me, like having time to think and to spread out mentally is what it means to me, and not to feel like… not just to take a deep breath before I start the day. Not to feel like, “All right, here we go, this is going to suck.” Like-

Sherry Walling:
You’re jumping into a cold swimming pool. Like, brace yourself.

Jason Fried:
… Right. I just don’t want to feel that way. Physically, that’s what it is for me. Just feeling there’s space around. Physically, literally feeling there is space around me. And that space is time, and the ability to think, and that no one’s breathing down my neck and I’m not breathing down anyone else’s neck. And there’s no one unreasonable. No one has an unreasonable work schedule. Those kinds of things are really important to me.

Jason Fried:
Again, that’s not to say that, like, there are moments when I get frustrated about something or like I wish something was done a certain way and it wasn’t or whatever. I mean, those-

Sherry Walling:
You have a full range of human emotions, Jason. Is that what you’re saying?

Jason Fried:
Yeah.

Sherry Walling:
Okay. I think that’s fair.

Jason Fried:
And it’s [inaudible 00:28:27] range. Yeah. But the baseline should not be sweating. It should be [crosstalk 00:28:35].

Sherry Walling:
[inaudible 00:28:35]

Jason Fried:
Yes. And you do need those things sometimes. Like, some people will say, “You guys just do nothing all day?” Like, “No, we’re very active. We were very productive, we’re doing a lot of stuff, and there’s a lot of conversations happening. And there’s that.” But everyone’s really in control of their own time and their own day. And I think that’s almost the only way to get there. Because if your schedule and your day is determined by other people being able to make it wherever they want it to be, it’s very hard to get into a rhythm that you can calm down and think clearly.

Sherry Walling:
Yeah. You’ve had this very long working history with David, 20 years, at least.

Jason Fried:
Almost, yeah.

Sherry Walling:
Has your trust battery ever diminished with him? And if so, have you fixed it? You charged it, I should say.

Jason Fried:
Yeah. I think David and I have a unique relationship. We see 90% of the world the same way, I think. And because of that, when we battle on things occasionally, or we argue or we debate, we know that it’s not going to be a never ending situation where everything we’re going to disagree. If we disagree about everything, it becomes very taxing very quickly, and then you stop talking because you don’t want to just get into a fight every time you talk. And I know a lot of founders who have co-founders who just disagree about I think too many things. And at some level, some people think it’s good, because you have multiple viewpoints, whatever. But I really think you need to have a pretty closely shared viewpoint on most things, and it’ll leave some room for some really fundamental disagreement on a couple of things.

Jason Fried:
So, I think we’ve been able to maintain a really good working relationship for for a long, long time now, and I think it’s due to the fact that we both respect one another, we’re able to go hard at each other occasionally when necessary, but we know it’s [inaudible 00:30:30] the product. So, I don’t think we’ve had trust battery issues. I mean, you have to ask him, but I really feel like we have each other’s back and our trust level has always been, I think, very high.

Jason Fried:
Yeah, I don’t think I’ve had that… I’ve had trust battery issues with other people and people have had it with me, and we’ve had to rebuild it and to remember that it’s again… I know, there’s like some situations right now in the company where there’s some people who don’t think… Let’s see. How would I put it? They may not think I like them for some reason. Like, I’ve heard some things. And I don’t know where it came from, but we have some rebuilding to do in some situations, but I think that the key is that it takes a while to do that and to find the opportunities where you can recharge. You can’t just jump into those situations. And so I think it’s good to ultimately find a project to work on with somebody or something.

Jason Fried:
That’s how I’ve, in the past, I’ve seen people rebuild each other’s trust batteries. In fact, there’s a couple of people working on a project right now who just kind of had pretty low charges against one another. And actually, it’s funny because it wasn’t really because of anything that they did to one another, it was an absence of interaction, and then hearing about one another from other people and you begin to form a picture of somebody when you haven’t had the direct experience. So we put them together on a project, and I think it’s going to turn out really well because I think that they’re going to actually see that they see [inaudible 00:31:50] most things and their level of detail and quality is very, very similar. And I think it’s going to give them an opportunity to have a good opportunity to work together.

Jason Fried:
Another example, this actually was, so, David and Ryan. So Ryan’s a guy who’s been also here for about 15 years. He’s our fourth employee ever. And he’s still with us. And he’s fantastic. But David and Ryan used to have some real headbutt, they used to headbutt a lot. And their trust batteries were low. And it was interesting, we had to figure out why this was, because if you were to separate them and talk to them, each at the same time, like they’d actually come from similar angles, in a sense. And they really respect each other’s point of view, but they were just always arguing every time they talked.

Jason Fried:
And it turned out that what we figured out was they didn’t talk enough. And whenever they talked, so, okay, Ryan’s head of strategy here. So, whenever Ryan and David and I talk, we’re usually talking about something that’s really fundamentally core and important. Like, we’re making decisions that affect the whole company. And so they’re kind of high pressure decisions, in a sense. And the only time that David and Ryan were talking was in those situations. I would talk to Ryan all the time, because we work and design projects together and stuff. But David and Ryan only talked when we had to make a really important decision. And that’s when we were all having difficult conversations.

Sherry Walling:
So the intensity is like nine out of 10 for every conversation that they’re having.

Jason Fried:
Exactly. That’s a better way of putting it. Like there’s a point where they didn’t want to talk to each other, because it always ended in this sort of heated debate. And at some point, it becomes tiring. And we realized, well, the only reason this is happening is because you’re only talking in credibly critical moments. So therefore, that’s the only experience you have with one another. And so, we started to talk in other ways, and the relationship is completely repaired. And it just was a moment of like, figuring out what was going on there, and realizing that it was the situation. It wasn’t actually the people so much as it was the situation we were putting the people into.

Jason Fried:
Anyway, there have been moments with other people are like that and-

Sherry Walling:
And you usually address that through some kind of collaboration that’s mixing up that pattern of interaction. So, it’s more fun, a little lighter, or more serious depending on what the interaction pattern has been.

Jason Fried:
… Yeah. Or another one is actually like collaborating on something versus having one person tell someone else something to do. So, there’s been situations where someone was like, structurally superior to somebody else according to job titles, and they would ask someone to do something, and it was always just like, ask them to do something relationship. When that happens, sometimes, depending on the situation, it can feel like, “Well, I’m just being told what to do. I don’t have any say in this. I have a creative mind but I’m not being asked to be creative,” or whatever it is. And so align them on a project where they’re both equally in charge is another good way to kind of rebuild the charge essentially, where they can work together versus having that relationship of, “I give everything to you.”

Jason Fried:
That’s a long answer to say that David and I actually have a pretty, I think, have had a really strong and consistent relationship over the nearly 20 years we’ve known each other.

Sherry Walling:
Cool. What’s something that’s bringing you joy right now?

Jason Fried:
At work, in life, where do you want to go?

Sherry Walling:
Whenever.

Jason Fried:
Well, we’ve a seven month old daughter so that’s, that’s wonderful. And she’s like, just smiles constantly. And it reminds me how powerful a simple smile is, because she’s just smiling all the time. It’s almost like she’s a robot that just is set to smile. I’m like, something seems weird almost, but it’s wonderful. And so that clearly is something spring. So, as we were talking a little bit before, I’m assuming before you started recording we’re talking about because you’re in Minnesota, I’m in Chicago, it’s April, kind of not always the most pleasant month because it’s like come on already. But like I’m looking out my window and I’m seeing the beginning of spring. That this small, tiny leaf buds popping, the croak is coming out of the ground, like tiny little flowers, green poking its head through the grounder. To me this is the best time of the year.

Jason Fried:
It’s sort of the end of a long, dark winter, in a sense, and the beginning of the rest of the year, and the beginning of seeing life. Like, life come back. I think that for me, I’ve always thought like it’d be fun to chase spring across the country as a one month sabbatical. Like start… I don’t know? Actually, I mean, you probably can [inaudible 00:36:24] the West Coast, because it’s always kind of nice. But you start somewhere where it’s not nice. And you just drive, I guess you’d be driving west. Oh, no, you’d be driving east-

Sherry Walling:
North, I think.

Jason Fried:
… North. North and east perhaps. And then you’d sort of catch it as you go. I always thought that’d be a fun project or a fun thing to do. But I like spring. Spring for me is great. Then the other thing just to bring it back to work for a moment, since we’re kind of talking mostly about that so far. We’re actually working on a new product. And that’s something we said we wouldn’t do again. We said back and I think it was 2014 that we’re going to focus entirely all of our energy in Basecamp, we renamed the company Basecamp and we’ve been that way for four years now or so, five years. But there’s been something that’s been itching us for a little bit and we decided to begin to build something new.

Jason Fried:
I don’t know when it’s going to come out. We’re hoping by the end of the year, but it really reminds me how much fun it is to start something new and to be able to bring new ideas into something from scratch. Because when you have a product like Basecamp that’s used by millions of people, 100,000 companies, you have to be mindful of, major changes will upset the cart in all the wrong ways. Even if they’re better technically or whatever, like, you just can’t really shake the tree that much.

Jason Fried:
When you make something new, there are no expectations and it frees you to do something new and stretch your skills in a new way. So, from the work perspective, that’s really fun. The last thing I’ll say is like, we’re going to spend as a family, we’re going, four of us, my wife and my two kids, we’re going to go out to Amsterdam for a month this late spring. We were there a few years ago and loved it, so, we’re going to do that. I’m looking forward to that. Those are the kinds of things that I’m happy about.

Sherry Walling:
Super fun place with kids too. Like, lots of long locks and swans and ice cream and flower, it’s just lovely.

Jason Fried:
It’s beautiful, and they have so many parks there, and I just found the culture is so welcoming and warm around kids. I don’t know. It’s a special city. When we did it last time, our son was a year and a half old or something like that, and it was really magical and we enjoyed it. So, now it’s going be fun to go back with him. He’s four and a half now and our daughter’s seven months and just see the city again, and we met some people, so we’ll see some people that we got to know. Also one of our good friends from Chicago, his whole family moved there on a whim, like, for a year, and they’ve stayed there for now five years, and I think they’re permanently going to be there forever. So, it will be good to see them and anyway, that’s that.

Sherry Walling:
That’s awesome. That’s fantastic.

Jason Fried:
What about you? What’s bringing you joy? What’s so interesting for you right now?

Sherry Walling:
My kids are making creative cool things. Like, they’ve been into making this card trading game where they have selected a stuffed animal and then they make like 30 cards around that stuffed animal. So, one of them is making his cards around a fish, an anglerfish, and so he’s making a cake angler and a spider man angler and all these different anglers, but they make this like really cool art. Then they make a backstory for each of the creatures. So, I think it’s like magic, the gathering, plus stuffed animals, plus comic books, plus all this stuff. They’re super into it and they spend hours drawing on the floor, and I’m like, “This is awesome.” That’s bringing me a lot of joy to see them make things and also to sit quietly and drink tea and have [inaudible 00:39:49] in my own mind.

Jason Fried:
Absolutely, that sounds fun. It’s fun to see kids makes stuff. And it’s funny because when adults make things, the question is like, “What are you making? And how does it work??” In some ways, but when kids make things, they don’t really… It’s not about that so much. I mean, can be. Especially I’m assuming as they get older, but it’s just this moment of creation. I almost feel like they sometimes don’t really know what they’re doing and they’re totally cool with that.

Sherry Walling:
They’re doing it because it’s cool and because it brings them joy, period. There’s no other motivation to make something as a kid except that it’s cool or fun.

Jason Fried:
It’s such a good reminder. Sometimes making stuff is… I’ve always felt like if I retire or whatever, stop doing this or I’m giving it up, whatever. I think I just want to be a potter, I’d love to just throw pots or make ceramics. I just would love to do that because it’s just good to make something new. Like, you’ve an idea and get this piece of clay, this chunk or whatever, and you turn the wheel you mold it and who knows what you end up with. I’ve always liked that about that medium, but as an adult, you want to sit down and go like, “I know what I’m doing and I’m doing it for this reason.” And it’s like, sometimes just, it’s hard not to, I guess, as an adult just to make things. [crosstalk 00:41:05]

Sherry Walling:
Or to justify the time.

Jason Fried:
Yeah, perhaps that’s what it is.

Sherry Walling:
I actually wanted to ask you a little bit about that, why you and David have decided to write so much. I mean, you could just run Basecamp and do that, but you’ve decided to write about it. What about that felt important or [crosstalk 00:41:22]

Jason Fried:
Well, it feels like part of the job, actually, so, just part of our Basecamp, which is sharing as much as we possibly can, about what we’ve learned, what we know and our point of view because I we’ve always felt like there’s no reason to keep it to ourselves. If we have something to say that we think can benefit someone else, or can push the industry forward in some way or can question the industry or whatever, we might as well do that, and might as well share it.

Jason Fried:
We don’t have a schedule necessarily to write. We’ve never had a schedule on our blog. If we have something to say we write it down and we share it. There are very few things we write and just share internally, unless it’s like truly private stuff. Otherwise, it’s just blog posts, and then it seems to be every five years or so, we’ve had enough experiences to put together a book about what we’ve been thinking about, what we’ve been working on for five years. Actually we’re writing something else right now, we’re putting together. Dave and I are not, but Ryan is here, extremely detailed guide on how we work. It’s going to be free, it’s going to be a website, actually it was written as a book but we’ve decided to make it a website. It’s going to be because, we get a lot of questions, “Like, how do you guys actually do what you do on a day to day basis in terms of making products and whatnot?” And so, we’ve broken it down and we’re writing that up.

Jason Fried:
Also it serves, when we write things for the outside world, it’s also for the inside world for our own company. Like, here’s what we believe and here’s why you believe these things and here’s the things that are important to us. I’ve always been inspired by chefs in this regard. So, chefs, open restaurants, or chefs, or chefs, and they write books and their books are cookbooks. They’re recipes, they’re best at saying, “Here’s what I know how to make, here’s exactly how I make it, and I’m going to put it in a book so you can make it to.”

Jason Fried:
I’m not afraid as a chef that you’re not going to come to my restaurant anymore because I taught you how to make my togliatti bolognese or whatever. Like, “No, I want you to know how to make, what I do, and maybe you come to our restaurant and taste my food too.” And I’m also not worried about someone buying my cookbook and opening up and reading all the recipes and mastering them and opening a restaurant next to mine and putting me out of the business, I just want to share the things that I have. It helps my business, it also helps me get the word out. It helps people become better cooks, it helps people cook at home and be healthy, whatever it is, right?

Sherry Walling:
Yeah.

Jason Fried:
So they do this and I feel like we’re basically doing the same thing, we’re writing up our recipes, and we’re sharing them in these books so we see these books as actually our cookbooks, which is, of course, they’re not some food, it’s ideas on how to work. So that’s why we do it. And we also enjoy writing, just a fun thing to do.

Sherry Walling:
That creative part of you. Do you have a sense of what people misunderstand about Basecamp? Or about how you all work? What’s the mistake that folks make? Or the misinterpretation?

Jason Fried:
That’s a really good question. It’s so hard to answer that from [crosstalk 00:44:08]

Sherry Walling:
I’m asking you to get inside someone else’s mind. So I appreciate that.

Jason Fried:
Well, I mean, I would say that there’s… I’ll come at it from a few different directions. One is that for a long time, I remember people just thought, we’re a marketing company. Like, they make products, they’re really easy to make. So it’s just marketing, it’s all marketing. We don’t actually do any of that. We don’t have a marketing department, we don’t have marketing people, we don’t spend money on advertising, we just share and talk and share point of view and so we do think the products stand up for themselves, and that people talk about them. The reason our businesses has grown is because it’s grown from word of mouth, it’s not grown because we paid anyone to use our products or we’ve had to buy anyone’s attention. It spreads slowly and gradually.

Jason Fried:
So, I think, there was that earlier on that we’re just like, “We’re good marketers.” I don’t think we actually are very good marketers. I think we’re good sharers. That’s the thing. That’s not really a word, I don’t think, but you know what I mean. So there’s that. I think there’s also a notion that we don’t do what we say. So, it’s impossible to work eight hour a days. It’s impossible to work 40 hours a week or back way in the day, when you first started, you must have been doing 100 hour weeks and all nights. I was like, “No, we just have not.” Eight hours is plenty of time” In fact, as I’ve said before, if you don’t think eight hours is a long time, go get in the airplane in Chicago and fly to London. That’s eight hours. And I guarantee you, that’s a long time. You’re going to be looking at your watch like it’s almost over yet, you’re like, “Oh my god, it’s only halfway done.” Like, “What?”

Jason Fried:
Eight hours is a lot of time. And so when people don’t believe that we actually do work eight hour days and 40 hour weeks, and we don’t space out about things, and we don’t keep pushing deadlines month after month after month after month, it’s like, we can actually get work done in six weeks, and whatnot. That kind of thing. I think that they just don’t believe it’s possible and that’s because of their own expenses and I get that. I think there’s some of that. I don’t know, I’m curious, what would you think? Do you have a sense? Do you know enough about what people would say about us? I mean, I always feel like [crosstalk 00:46:09]

Sherry Walling:
I do think the [inaudible 00:46:10] are held up as this… because I obviously talk a lot with people about mental health and how to be healthy at work and how to be well at work and people will say, “Well, we want to do it like Basecamp does.” Where it’s just really calm, and we don’t have meetings, and people get a lot of work done, but also it has sort of never land feel like the last voice can do that, but not real people. I think that’s what you’re saying. It sounds so idyllic because we’ve created such a fiction around what’s necessary for success.

Jason Fried:
People think that, if you’re not busy. If you’re not feeling busy, then you’re slacking off or something. That you’re not working as hard as you could be, or whatever. It’s like, this whole idea of working as hard as you could be, I don’t really know where that needs to come from. You don’t need to work as hard as you could be. That’s not something you need to do to begin with. I think if people were able to just watch how we work, they would see that there’s actually quite a bit of conversation happening. So we do talk to each other a lot, but we talk to each other asynchronously.

Jason Fried:
So we post things to Basecamp, and there’s no expectation of immediate response. It’s like, I write an idea up, someone maybe comments on it eight hours later, or the next morning, that’s fine, versus putting everyone in the room and talking about things. When you do that, sometimes it’s valuable, certainly, there’s no question about it, but often times, I think you’re turning something that’s slow time, it could be better off handle as slow time into fast time, and everyone has to answer questions immediately and it’s not necessary.

Jason Fried:
So, I think that there’s a lot of conversations just a synchronous, I think the other thing people would see is that we actually make swift decisions. That’s one of the key things is the ability to make calls and have conviction in them and move on and go, versus, a lot of the reasons, I think a lot of things take a long time is because people, they’re not sure what to do, and they don’t know, and the answer is, “We don’t know and we’re not sure either.”

Sherry Walling:
But let’s go this way.

Jason Fried:
And we go. If it’s wrong, we can correct it later, but the idea that you can wait, that waiting will get you the right answer. Sometimes, yes, sometimes you need more information than you have and you need to do more research. Sometimes that’s true, but not about everything. I’d much rather basically make quick calls, listen, make a call and go, and get the thing going, than try and be right every single time because even when you try and do it every single time you’re not. Anyway, I think those are some of the things.

Jason Fried:
I don’t know. It’s an interesting question. I should think more about it. I would also say that on the flip side too, from the product perspective, I think that there are probably a number of people who think Basecamp is old, Basecamp is not modern, not the new kid on the block kind of thing. That’s true, we are not the new kid on the block. But we redo the product from scratch every three or four years basically, and today’s Basecamp is thoroughly modern. Ans can replace, if you use Basecamp, you don’t have to use Slack, or Trello, or Asana or JIRA, or Google Docs or a calendar, it’s all in one place. I think over the years, people have forgotten about that and or perceived us as we haven’t changed because the products been around for so long. So that’s something we have to combat as well, which is a challenge to get people to look at you again, who may have looked at you eight years ago.

Jason Fried:
Most companies that we’re competing with didn’t exist eight years ago. So, there’s an interesting challenge there, which I think maybe something that people get wrong about us. But that’s our fault. We need to figure that out.

Sherry Walling:
Yeah. Hey, I appreciate it being able to email you and say, “Hey, do you want to do this?” And you saying, “Yes. When do you want to do it?” And I sent you a couple of times and we found time and we did it. And there wasn’t like, [inaudible 00:50:03] an assistant or a team steps to get to your calendar.

Jason Fried:
Thank you. I mean, I don’t have an assistant who manages my calendar because my calendar is pretty much wide open. So I’m like, “Hey, when are you free?” Throw out a couple dates. Certainly one of those will work, let’s do it. The other thing is that, I tend not to book things very far in advance. I find that to be a bad way to go about things. Sometimes you have to travel, something like that, but I tend to be like, yeah, this sounds like it’d be fun. Let’s do it. I’m glad you were able to do it, too and we were able to find time that worked and that you asked and we got to meet up at the conference. So, that’s great. Thanks.

Sherry Walling:
Well, thank you. As somebody who cares deeply about mental health and people being well at work, I’m a huge fan and I love your work and, of course, your most recent book has, I think, become a Bible to people in my line of work who are trying to bridge the conversation between wellness, insanity, and what that actually looks like in the day to day job. So, thank you, you’ve made my job a lot easier. Now, I can go, “Jason Fried said this. Jas said this.”

Jason Fried:
Please. No one’s going to know that is in your world, I’m sure. Speaking of this, we should maybe consider having you come speak to us sometime at a future meet up. We have one in two weeks, which is too soon, because we already have some stuff going on, but perhaps in the fall, [crosstalk 00:51:26]

Sherry Walling:
I will be thrilled.

Jason Fried:
So, we’ll touch base about that.

Sherry Walling:
Save the day.

Jason Fried:
All right.

Sherry Walling:
All right. Take good care.

Jason Fried:
Thanks so much.

Sherry Walling:
Bye.

Jason Fried:
See you around. Bye, bye

Sherry Walling:
Thanks for listening. We’ll be back in two weeks with a new episode of the podcast. In the meantime, feel free to check out zenfounder.com for lots of resources about the kinds of conversations that we have on the podcast. You can get information about working with me, about maybe joining a Zen tribe. It’s like a mental health boot camp for entrepreneurs. We also have lots of content on our blog, links to resources in our courses and books for sale. So, check us out there and we hope to provide anything and everything that you might need to make the entrepreneurial life a little bit easier.