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Episode 50: Interview with Jason Fried, Co-Founder & CEO of Basecamp

The Heartbeat Podcast - Leaders share their biggest, hardest lessons learned. | Product Hunt Embed

This week, Jason Fried, CEO and Co-Founder of Basecamp and I, your host, Claire Lew, CEO of Know Your Team, interview each other for this special milestone episode #50 of The Heartbeat. We talk about learning how to be like yourself earlier, thinking about long-term views as leaders, how leadership roles change over time, and letting ideas go when you have to.

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CLAIRE: Hey everyone, I’m Claire Lew and I’m the CEO of Know Your Team. Today is a super special day because on The Heartbeat, we have the one and only Jason Fried, who is the Co-founder and CEO of Basecamp, a project management tool that if you’re not using, I don’t really know what you’re using, is what we base our entire business off of. And for those of you who’ve been following Know Your Team, we were a spin-off company of Basecamp as well. But I wanted to actually ask Jason to come back on the show because Jason was the very first person I interviewed for The Heartbeat when I started this series two and a half years ago, when I look back. And today is a particularly special episode because it is the 50th episode that I’ve done of these, interviewing all sorts of leaders that I’ve admired all over the world. And I thought Jason, for this particular one, Jason and I talk regularly. He sits on our board at Know Your Team that you would be possibly the best person to maybe flip the tables this time around and ask me the one question that I’ve been asking leaders over the past two and half years on this podcast. So, I thought that’s how we would kick things off and then I have a bunch of questions for you because there’s so much to hear. Should we start there?

JASON: Yeah, this is great. First of all, thanks for having me on. It’s an honor to be on the 50th episode and to be chosen to ask you this very special question which is basically as you start off all your interviews, you always ask, what’s one thing you wished that you’d known earlier about being a leader? So, let’s turn the tables and ask you the same question. What do you wish you knew, let’s call it, 10 years ago?

CLAIRE: It’s so funny. I’ve literally asked this question likely more than 50 times and maybe in the best form. You try not to think of your own answer to the question that you ask. And I even knew that we were doing this episode. So, it’s funny, it’s like I didn’t really prepare for it. I’ll just share the first thing that comes to mind, which is:

I really wish I had learned to be more like myself earlier, which is probably some leadership poster cliche thing that’s written everywhere. Be more like yourself or trust yourself. But I just have noticed that when I was first starting out, and I mean, you’ve known me for a while before I was even running Know Your Team and getting started. And I think one of the hardest things when you’re even just leading yourself, so before I even had a team is figuring out, “What do I believe in? What do I care about? And how true do I actually even stay aligned to that?” And I think the first instinct when you’re trying to answer those questions when you’re starting out is you pattern match and you go, “Oh, I’m really a big fan of the stuff that Basecamp does. I’ll talk to Jason and David and you hear about how they run their teams and how they work with people.” Or maybe I’ll talk to some professors or I’ll talk to other mentors or people who are older than me and wiser and making lots of money. This just seems like this would be the right path. And I would try those things and who’s to say to what degree things worked or whatnot. But what I found when things would go either faster or smoother or I would get really good feedback from the people I was working with was when I wasn’t looking at any other pattern for what I thought could be true. And so, that’s probably the biggest thing even today. It’s like having tried to internalize that lesson. Even today, I’ll even notice myself being, “Am I doing this the right way? Am I having these conversations or making these decisions in “the right way”? And then I’ll go back and talk to people. It’s almost like a funny, weird habit to try to kick off, there’s really no answer to figuring out how to do any of this well, whether you’re running your company or managing your team and how do you try to be more like yourself? So continual lesson maybe, I’m still trying to learn.

JASON: That’s such a great point. And it’s something that I think a lot of business leaders at all levels struggle with, which is can they be themselves? Are they allowed to be themselves? There’s a sense that leaders need to be these strong people who are always right and always pointing in the right direction. And we try to often emulate that. But then you’re not being yourself, and you can’t lead if you’re not being yourself. And people want to follow you, they don’t want to follow the caricature of a big, strong leader kind of thing. So I think that’s really important. The thing is that you’re small company. You have what? Three people? Four people now?

CLAIRE: Yeah, we’re four people total. We’re tiny.

JASON: Oftentimes people I think who are new are looking out at leaders who are running massive organizations and thinking that they need to model themselves after those people, but those people have a very different challenge than the challenge you have. You’re going to be much closer to your team and much closer to your people. So it seems like it’s a different style of leadership that I think you’ll have to evolve into it as the company grows as well. But I’m kind of curious, you’ve talked to 50 leaders at least many more, but you’ve interviewed 50.


JASON: What surprised you most about these people?

CLAIRE: Everyone actually has a different answer to that question that I asked or that you asked me rather. That’s actually been the most surprising thing. I almost assume when I started down this project of, “Oh, I’m going to ask the same question.” I have a feeling I’m going to have to stop at some point because people are just going to start saying the same things. And what’s so weird Jason is everybody says a different thing, literally. They might fall under sort of broad scopes of like, empathy is important. That’s like a theme that’s come up or communication’s important or humility is important. There are themes but everyone has a really sort of individual, not to be dramatic, but almost demon that they’re personally struggling with and trying to sort of figure out and wrestle and nail down, and I respect that.

JASON: Was there a particular interview, I know I’m asking you to go back through the inventory in your mind, but was there a particular interview that surprised you in terms of like, I thought this person would have been X but they turned out to be Y in a good way, of course. But was there any lesson that was shared by somebody that you felt you really legitimately surprised by and it caused you to reflect on your own leadership. To feel like you’re learning. Part of the interview process is getting to learn from other people. So I’m wondering if anything changed your mind basically.

CLAIRE: Changed my mind. Yes. One of the most memorable interviews that I did was last year with Peldi, who’s the CEO of Balsamiq.

JASON: He’s great.

CLAIRE: Yes, phenomenal. Been a client of ours for a while and I mean, he was immensely flattering. He’s saying, “Oh Claire, your writings deeply influenced and changed the way that I’ve been running my teams.” And it was so funny because then what he shared changed it in my mind. So the thing that he talked about was how he has this really interesting tendency to want to sort of save the day all the time. So people come to him with problems and he’s like, “Great, I fix them. I put my thinking cap on. I roll up my sleeves and I go and I fix them for people and it’s great for a little while.” And then he notices that over time, different bottlenecks start to happen where all of a sudden everyone is coming to him with these problems. And then realized that the things that he is actually good at, he needs to stop doing. I’d always sort of known and read about and there’s so many studies and you sort of look at all sorts of academic scholars who studied leadership and there are a lot of different frameworks for — yes, delegation’s important. Like the whole purpose of the teams just sort of separate tasks and so you’re not the one doing them and your role as a manager is to enable people, blah, blah, blah. But the framing of it as like, “Look at the things you’re good at and stop doing the things you’re good at.” I was like, “Huh! Interesting.” Good leadership is almost always about internalizing positive behavior change. And I felt like what is more sort of powerful than telling yourself to look in the mirror for the things that you pride yourself in and then you’re like, “I’m kind of really good at that. Everybody comes to me for that.” And being like, “Stop.” I just thought that was so refreshing.

JASON: Was he trying to essentially create more responsibility for the rest of his team? Was it like, “I know I can solve this problem but it’s not going to help people if I actually solve it even though they’re coming to me for help.” The real help is to say, “Actually, figure it out yourself.”

CLAIRE: Exactly. And for him, and this is what I really appreciated about what he shared as well was it was about self-sustainability for the team that if the team needs to be successful when he’s on vacation, well he can’t be the one then being sort of saving the day. What if he’s out for a few weeks, on a tactical level. And then just thinking, “If I want this team to sort of really survive and thrive and [inaudible] without me if I want Balsamiq to, in the long run, sort of outlast me. How do I think about doing that?” And I think that long-term view of leadership and you’re a perfect person to talk about this, your Basecamp, you’re at what? 20th year?

JASON: 20 years this year, yeah.

CLAIRE: Exactly. That’s no accident. You have to try pretty hard if you want to be around for 20 years, I think. You kind of have to really want to not die and keep doing something. I appreciate that as well because I think, it’s kind of a byproduct of our culture that we just focus on. What’s going to help me in the next six months or what’s going to help me in the next year?

I’ve got so many questions for you, Jason. I was excited about this. But one of the things I was curious about is 20 years running Basecamp, I was listening to the Rework podcast the other day and you said something really interesting where you said you’re always thinking about it though as the first of the next 20 years, some ways?

JASON: Yeah.

CLAIRE: For people who haven’t been running anything for 20 years like myself, how do you really ingrain that long-term view as a leader? What’s happening there?

JASON: A lot of the decisions we make, we put them up against like, will this help us last? So for example, one of the reasons we work 40-hour weeks is because if you work 80-hour weeks, it’s going to be hard to do that for a long time. You might be able to do it in short spurts, but the first thing is we have to establish that we want to be in business for a long time. It’s something that sounds kind of silly, but you actually have to say, “We actually want to be around for a while.”

CLAIRE: You’ve got to want it first.

JASON: Yeah, you got to want it first. So you got to set that out and go, “We want to be around for a while. Therefore, what are some sustainable practices we can follow?” Work week, our cadence of our projects, type of expectations we set for ourselves or don’t set for ourselves. The fact that we don’t set up unreasonable goals or unattainable goals or structure. We’re very focused on the now but also knowing that the now is hopefully going to continue for the next 20 years. So we turned 20, and I talked to the company, we had a meet up around this time when we turned 20 about, “So, what about the next 20?” So we did talk about the next 20. And there’s always momentum behind you. You’ve been around for a while. So there’s a lot of momentum, there’s a lot of decisions, there’s a lot of confirmation bias, there’s a lot of things that have happened to get you where you are. And it’s easy to think that now, like the next 20, we should keep doing the same things because it worked over the last 20. And maybe some of those things like fundamental values and principles I think are important. But when it comes to tactics and strategy, I think we need to think about this as like, “Let’s think of the next 20 like we did the first year of our last 20,” which was like, we’re new and we can do new things and we’re sort of pushing ourselves. I’m trying to push us to do interesting things that we haven’t tried before. So, product launch in Spring. We hired a head of marketing, which is something we’ve never had before. We’re doing some things that we hadn’t done before. And I think had we thought that this was year 21, we probably wouldn’t have done those things versus if we think it’s your one of the next 20, then I think we kind of give ourselves permission to experiment some more. So I think it’s important to do that and set the tone.

CLAIRE: Absolutely. Do you think that re-framing helps with feeling almost like letting go of that sense of we don’t have anything to lose. What’s the plaque that sort of builds up, like mental plaque or emotional plaque of, “I’ve been doing this for a while and it’s been working well.”

JASON: Yeah, it’s a great question. I find it liberating to just like, “They were starting again,” which of course we’re not really. We’ve got tens of thousands of customers. We’ve got a long history. We’ve got brand equity out there, people know us. So we’re not starting, it’s not fair for me to compare starting new to someone who’s really, truly starting new. Truly starting new and no one knows you is quite a bit harder than where we’re at. But there is this notion that as a company grows and as it’s around longer and as more customers and there’s higher expectations, there definitely is more to lose. And so you end up calcifying and you end up stiffening up because you’re afraid and now you’re just in defense mode. Like, I just want to maintain and keep what we have, instead of figuring out how to do new things. And so, I think it takes a heavy hammer to break that coding basically, and let us kind of loosen up again and say, “Let’s try some new stuff. Who knows if it’s going to work or not. But let’s not be afraid of it.” Because it’s so easy to be afraid when you have something.

CLAIRE: Oh, yeah.

JASON: That’s the thing I feel like I have to constantly remind people that like, “We’re okay, that’s great.” But it won’t be okay if we just keep doing the same things we’ve always done because that’s what we’ve done. We need to do new things that make sense in context of who we are today, what the opportunities are, what excites us, that sort of stuff. So, I think it’s really important.

CLAIRE: Absolutely.

JASON: I have a question though, actually, if you don’t mind.

CLAIRE: No, go!

JASON: Something I’ve always wondered about is how do you find the people you interview? So you’ve interviewed 50. What is it about…

CLAIRE: I begged them, Jason. I begged them.

JASON: Okay, fine. Let’s say you begged them. Who do you choose to beg and why? What is it that you’re looking for? I’m curious about that because look, there’s hundreds and hundreds and thousands of leaders. So, how do you pick these 50?

CLAIRE: That’s a really good question. It’s funny too because it was cool. The podcast has been reaching more and more people and so I get a lot of emails from PR agencies and agents who are trying to suggest that their CEO or their client is the one that gets on the show. And I’ve actually said no to all of them or I don’t respond, which I don’t know if that’s necessarily the best strategy. But what I will say is I try to seek out people who I think will have something different to say and who aren’t going to sit on talking points. That’s like a really big thing. So I don’t like to, for example, accept people on the show who have a thing going on right now, like a book to promote. Sometimes, it overlaps actually. And like, I don’t know, I think the book’s really good and I’m like, “Oh, I want to talk to this person.” For example, we had Mollie West Duffy who did Emotions or the exact name that I’m forgetting, but excellent. I was like, “Oh, this is going to be great.” We’re going to have Jerry Colonna,, who wrote Reboot and is a fantastic executive coach. He’s going to be on the show shortly too. So there is exceptions in that sense, but I think the value of these conversations or why I even want to do this podcast in particular is I wanted to get away from the heavy-handed, crocheted sort of personal brand of leadership. This idea that because it works for me at GE or it works for me at BlackRock that this is the way you do things and it’s one, two, three, and these are like the catchy sayings that I have and mnemonic devices I have for you to implement these things in your team. Because I just don’t think leadership works that way. It’s proven. You look at any team in any organization and it’s just so freaking different. And so what I was more curious about are who are going to be the people who are actually going to be willing to open up about what’s been different in particular about their slice. Because I think that’s where the value is. It’s not in any one person’s particular sort of path or slice of what they learned, but it’s the accumulation of sort of seeing the whole bank of stories and being like, “Oh, interesting. This part of what Jason is sharing was really interesting about not being worried about so many things.” But maybe that doesn’t apply in all situations. “This person does trainers viewpoint. This is really interesting.” And, “Tim O’Reilly has this.” And you just sort of assemble your own collage of what’s making sense. I think that’s where the value is. And so finding people who are willing to get real about that and be honest about that. And that’s the way I’ve thought of it. And so usually that means I’d meet them in person. That’s usually how it happens is I’ll meet someone at a conference or I’ll watch and speak at an event or someone will introduce me to someone and I’ll go, “Oh!” There’s something just about the way they’re thinking, what they’re sharing with me that seems like they’d be willing to be honest.

JASON: Well, that’s good. I think meeting someone first is kind of a good basic first bar, just so you can tell if they’re kind of the real thing, perhaps. I think the other thing that I had noticed about your interviews for the most part, I don’t know all the people of course, but they’re all like practicing leadership right now. Like they’re running something versus someone who used to run something and is now like writing a book about what it used to be like. So I think it’s really good for all practitioners.

The thing that I think people will get confused about when it comes to leadership is that leadership is not like you’ve arrived at it and you’re good at it. Like most people, you end up there and you don’t know what you’re doing. I mean, we’re all figuring out as we go. I actually feel like pretty much every company is actually held together with duct tape. Everything’s tenuous that people aren’t really sure and no one has the real answers. We’re all trying to figure this out as we go. We have strategies and people have plans and people want things to turn out a certain way, but leaders don’t know either. We’re just someone trying to figure out our own job, like everyone else is trying to figure out their job. No one has all the answers. So I think it’s refreshing when you hear people, and I’ve heard a number of people on your podcast talk about like, “I’m not really sure what I’m doing. I’m trying to figure this stuff out too.”

CLAIRE: That vein of uncertainty and the humility and self-awareness that people have to see, that’s like the consistent thread. All of the interviews. Everyone is just sort of willing to admit like, “I’m trying it out and it seems to be working,” or, “This isn’t working,” or, “I learned this the hard way. But you know, I’m not quite sure.” Someone told me this, I forget who, but I really liked this phrasing. They talked about every company, it’s a beautiful mess. So to your point of being held together by duct tape, but it’s a beautiful mess. And like the beauties in trying and putting in the effort to figure out what’s working and what’s not. But it’s just a complete mess. That’s also life. It’s not this perfectly painted picture where everything’s aligned and connecting the dots. And so, I think that’s also what makes practicing leadership so hard. Because unlike other skills, for example, being an excellent violinist or a guitar player or a golfer or a tennis or whatever the thing is, you know what excellence looks like and there’s a very, very clear path. There’s a picture of success and then they do one, two, three, four, if you want to become that. It’s like, you practice this many hours a day, you go move to this place, you get this coach, then you go to Juilliard, then you get your apprenticeship doing this, you do this for three years. We don’t even really know what excellence looks like because it’s different depending on the team and what’s going on. And so it just makes even getting there harder. As you know, it’s why I’m doing this, running your team and this is what we’re trying to figure out how to do because it’s completely unclear.

JASON: Yeah. You know what’s neat about that is you think about like a great musician or a great athlete, they’re probably going to be great in any venue. Any venue they go to, they’ll put on a great performance. But leaders are really dependent upon their teams. And so you think about like, could this person be pulled out of this situation and put into another situation and be good at what they do? Maybe not. Probably not, in fact. We, as leaders, are such a product of our own teams and we rely on our teams to allow us to do what we do that if we switch teams, we might be horrible. We might get canned. I’d probably be fired if I want to work somewhere else. At some point, you’re so attached to your team. Of course, there are principles around leadership that you hope you could carry with you, but it has so much to do with the people around you and the situation and the timing and all that stuff that that’s what makes it interesting like you said, is that it’s not like, “Here’s the marathon training regimen. Then by the time you’re done with this, you’ll be able to run a marathon, guaranteed.” It doesn’t happen here. There’s no way to say by the time you’re done with this, you’re guaranteed to be able to run a team successfully. You don’t know, and that’s what’s kind of different about this.

CLAIRE: It’s fascinating. There’s so many studies on this, there’s everything from [inaudible]. And so, there’s major themes, but it’s still like the — for example, like the three main skills that we found out – all leaders, the best leaders tend to exhibit, it’s trust. You have to build trust in your team. You have to communicate honestly. And then you have to create context. None of this is rocket science. The hard part is how do you build trust? What does that look like on a day to day basis? How do you create context, especially when things are nuts and the market’s changing or you’re running out of money? How do you make sure everyone’s in the loop or when you’re remote or hybrid? It’s the doing. That’s the hard part. It’s less the, Oh yeah, I know I should be honest with my team.” Yeah, you’re right about that all day. Doing it is a whole another story.

JASON: And there are different phases of leadership because sometimes, you might be struggling to pay the bills. Now you’re in a survival mode, which is totally different. Then when you’re comfy and cozy and things are going well for a while and you can take some more chances or whatever. So, it does require you to sort of morph and shape shift a bit. It’s an interesting area of study because who knows, it’s always evolving.

CLAIRE: It’s not rocket science. It really isn’t. Speaking of evolving, shaping, shifting, the last time we talked on this podcast, Jason, it’s actually funny that very first interview we did. I think it was 10 minutes and we filmed it in the Basecamp office and I was like, “Hey, can you just like, do you want to just come in and like do this? I’m trying this thing out. I don’t know if we’ll do any more episodes.” And here we are two years later.

JASON: Were we sitting next to each other like in front of the same laptop?

CLAIRE: Exactly. It was super hilarious. Everyone go watch back that first interview. It’s gotten phenomenal feedback.

JASON: It’s a fun setup.

CLAIRE: But looking back, it’s like you never really know what something’s going to turn into. But since then, that’s two and a half years ago and things have changed. The company’s grown. What do you feel like you’ve learned in that time or change your mind on or just feel like, “Hmm, I’ve noticed myself evolving in some ways as a leader, trying different things out?.”

JASON: One of the things is we’ve, I don’t remember how many people we had back then, but we’ve probably added 10 people or something since, and that actually turns out to be pretty significant at this point. We have 56 people and it’s a lot harder I found to communicate with 56 than let’s say 46.

CLAIRE: Really?

JASON: Yeah, I just have found that.

CLAIRE: It surprises me.

JASON: Yeah. This is what I think it is. Maybe the way I communicate is the same, but there’s more communication in general happening across the company because there’s more people and there’s more projects and people’s time is more taken up by those things. When you want to communicate something, not everybody happens to run into it anymore like perhaps they may have used to. And so you find yourself having to sort of explain yourself in different ways and maybe explain yourself twice or repeat yourself. And that’s been a really interesting thing I’ve noticed is that I’ll say something and then I’ll think it was clear and then I’ll find out that some people didn’t think so and didn’t know and then I’ll have to say it again. And so, trying to tweak my communication style, I think, is really important to provide. What I’m trying to do is provide more context around why I’m making decisions, not just the decisions. I think in the past when we were smaller, it was just easier to share the decision to move on. But now with a lot of people in the company who are newer to the company, more than half of our company has been with us for more than five years, which is great. But that means that a little bit less than half, but still 20 almost the 25 people or so have been with us for just a few years and they don’t have any of the context around like how we ship products, how we launch products, why we do what we do. So I’m finding myself in a good way having to provide more justification for the decisions we make. And that’s been something that’s new for me. So learning that.

When you want to communicate something, not everybody happens to run into it anymore like perhaps they may have used to. And so you find yourself having to sort of explain yourself in different ways and maybe explain yourself twice or repeat yourself. And that’s been a really interesting thing I’ve noticed is that I’ll say something and then I’ll think it was clear and then I’ll find out that some people didn’t think so and didn’t know and then I’ll have to say it again. And so, trying to tweak my communication style, I think, is really important to provide. What I’m trying to do is provide more context around why I’m making decisions, not just the decisions. I think in the past when we were smaller, it was just easier to share the decision to move on. But now with a lot of people in the company who are newer to the company, more than half of our company has been with us for more than five years, which is great. But that means that a little bit less than half, but still 20 almost the 25 people or so have been with us for just a few years and they don’t have any of the context around like how we ship products, how we launch products, why we do what we do. So I’m finding myself in a good way having to provide more justification for the decisions we make. And that’s been something that’s new for me. So learning that.

CLAIRE: I’m surprised at the inflection point, by the way, being like 46 to 56.

JASON: That’s probably more than 50.

CLAIRE: I think that’s just interesting. I think it’s a similar experience based on other CEOs and executives I’ve talked to. So anyway, back to what you were saying,

JASON: So there’s that. The other thing I’ve had to come to terms with is I’ve gotten worse at some things that I used to love to do. I used to love to do more of the hands-on design work and this is kind of probably what Peldi was talking about in a way. I used to do a lot of hands-on design work, HTML, CSS. I just found myself having less time to do that and therefore my skills have atrophied. And so at some point, you have to realize you can maybe, but it probably is a good thing that certain things you’re used to be good at, you’re not good at anymore because that means you have to get better at other things. And I’ve realized that strategic thinking, big picture thinking, having time to think, that’s where my time is better placed than me digging into the code and messing around although I have always loved to do that. I’ve stayed out of it long enough now that I feel like I’m a little bit nervous getting back into it. I feel like I’m not as good as I used to be and things have changed there. And I think that’s something that I’ve heard from a number of leaders, which is like, “Look, your job changes.” You probably used to be an individual contributor and now you’re a leader or a manager or an owner or whatever you are. And for a while, you can hang onto those old skills because they take a while to fade, but at some point they do fade and then you need to pick up new things. And just kind of coming to terms with that has been the challenge and something I’m still struggling with is like, I’m not as good at those things as I used to be and I can’t just jump in like I used to. I have to maybe ask some people to do some things for me now, which I used to do myself. And that’s been hard actually. And it’s been more noticeable over the last couple of years as web technologies changed in a way where I’m not as up to speed as I used to be. So that’s something that’s changed that I think has been interesting. And then the last thing is again getting back to this whole like 21 or the year one of the next 20 thing, just kind of recognizing that like maybe the things that we’ve done and maybe the leadership skills that I’ve had, they still work but maybe they’re not going to work as well and I shouldn’t expect that they will automatically work even over the next five. So, the notion that what has worked may not always work is I think an important thing to come to. And it took me awhile I think probably to get to that where in the past, I might fall back on habits, “This is just how we do things. So, we’re going to do it again because it worked before.”


JASON: For example, saying five years ago we said we weren’t going to build any new products anymore, which is one of the reasons we spun out Know Your Company and now Know Your Team. And we’ve just decided we want to build something new. We said we weren’t, so we won’t, but that’s just something we made up. That’s our own rule. We can change that rule too. I think that’s a really valuable thing to do from time to time. So we’re doing that with this new thing. We’ve got a couple other things planned next year that we’re going to do that we said we probably wouldn’t do before. And I liked this idea of things we said we wouldn’t do, those are the things we’re going to start doing and see what happens.

CLAIRE: I love it. You’ve always been refreshingly just such an advocate of being able to change your mind. It’s okay to change your mind. It’s okay to change in general and that change is important. So, I love that.

JASON: And tied to that, I feel like I probably disagree with myself a dozen times a day.

CLAIRE: That’s a lot of times.

JASON: Maybe, it’s probably accurate though. Just things I’m thinking about. You got to see it from all these different perspectives and you have to see the different sides and you have to play the other angles. And I think I’ve gotten better and better at that as well. When before, I might’ve been a little bit more of an absolutist on certain things because I’m so confident that this is the right way. And now, I’m more willing to go, “You know, I actually don’t think this other way’s the right way, but I’m going to try that to find out,” because if I don’t try it, I’m not going to know. So I think that’s a valuable thing to kind of throw yourself into situations like that where your instinct would say this is wrong and your instinct has served you well in the past, but these things should evolve, so your instinct should evolve in a way as well. So anyway, that’s kind of where I’m at right now.

CLAIRE: What in these next 20 years, Jason, do you want to improve the most as a leader? You know, casual, big question.

JASON: Sometimes I have a hard time if I really believe something and it’s shown not to be true sometimes or maybe the data shows otherwise or sometimes I just have a hard time admitting that. I’ll look for justifications to say, “Whoa, Whoa. Not yet.” Or maybe like, “Maybe we’re looking at the data the wrong way.” Sometimes I hold on to things a little bit too tightly or hold on to convictions or hold on to guesses or bets or whatever too tightly. And I think sometimes you need to do that because sometimes it does take a while for something to play itself out. And sometimes it takes six or seven attempts at it to make it work. But there are definitely times I know where I’m like, I should actually come to terms with the fact that this wasn’t working or this didn’t work. So, I’d like to get better at that. That’s a hard thing for me. I think I’ve gotten better at it, but I still recognize myself kind of clinging to an idea that I had because like, “I still think it’s a good idea,” but like, “Hey, it just didn’t work.” Sometimes, it just doesn’t work. You got to move on. I’m working on that. I think that’s something I’d like to get better at. And that’s a leadership thing because I don’t want to continue to ask people to go in a direction in a given project or situation or whatever it might be that just isn’t panning out, but I feel like it has to pan out. And it’s the wrong way to go.

CLAIRE: It’s funny, I feel very similarly in the sense that I can get very attached to a vision or a point of view. And I find that it always ends up leading me in the wrong place. It’s like, that eventually didn’t work out or we just spent all this energy trying to make it work and it didn’t work. And then I think the other thing for me that I thought a lot about working on this myself is like, is that behavior that I want our team to learn. Do I want everyone to be that attached to their ideas? It’s my expectation actually. The expectation that I have on my team is like, we talk about things as objectively as possible and it’s all in service of this bigger thing we’re trying to build and we can’t be attached to the code that we’re putting together. We have to be able to throw stuff away. We have to view everything as an experiment. I say that and it’s always interesting to hold up that mirror and be like, these are the ideas that I like. How closely am I tying myself to that and holding myself accountable to that? That self-check is always hard. So, thank you for sharing that.

JASON: Yeah, it’s really hard to do. And all we can hope is we get slightly better at it. There’s no way to perfection probably. But hopefully every year, every month, every quarter, whenever we can get a little bit better about it and let one idea go that even though you’re clinging to it, some things just need to resolve and go away, like it didn’t work or not the right idea or whatever. But the challenge of course is figuring out. It’s hard because when you pick that moment to say, “I’m going to throw in the towel on this one,” Because sometimes things do take a while. So that’s the challenge and you got to kind of figure out how to put the needle, but it’s something I think that will take forever practice to get better at.

CLAIRE: Absolutely. I literally have so many questions, Jason.

JASON: Part 3, another time.

CLAIRE: Exactly.

JASON: The 100th.

CLAIRE: Exactly. Only 50 more episodes here. But the one question that I have at least on my end that I do want to ask is, especially just given this really interesting point in Basecamp’s history where it’s the biggest you’ve ever been, and for the past few years, you’ve had sort of managers in the company for the first time other than really you and David. I’m so curious through that transition, this is not just unique to Basecamp or any company that goes through that natural growth, but how have you thought about how you grow or influence, I don’t even know if influence is the right word, but even set a good example for the managers that you’re working with. Do you think about coaching them? I’m just even curious the way you think about it. Is it, “Oh no, Claire, I kind of just like try to be the best CEO and do the things that I’m doing and just hoping that by example people pick it up.” Are you really deliberate on that coaching aspect? How do you think about that relationship between you and now these managers that you’ve got?

JASON: I tend not to coach that much once someone’s become a manager. But ahead of time, I have a sense. Like for example, Jonas. You know Jonas.

CLAIRE: Of course.

JASON: Jonas is now the design team. He’s been promoted to lead the design team at Basecamp. For the past year or two, Jonas and I had been working very closely together on product development. And in the back of my head I’m thinking like Jonas could be a great manager. And so, I’ve been kind of, over the past couple of years, helping him or involving him in more conversations, involving him in more debates with David and I. Like David and I might be going at it on something and I pull him in so Jonas can see how we think about things. Trying to get him really involved in these things before it’s time to actually say like, “I think it’s time that you’ve earned this chance,” or wherever it might be. After that, I feel like I’m much more light handed on the coaching after the fact. So, I try to bring people along and help them get better and then sort of set them free and then be like someone who checks in from time to time versus being really heavy handed with the coaching. I feel like it’s all ahead of the moment, not after the moment. That’s kind of how I’ve always done it. I don’t know if it’s good or bad, but that’s how I’ve always done it. And I haven’t had a lot of experience because there’s only been a few people in the company that we’ve kind of put in that position. But I feel like it’s really good versus taking someone who is an individual contributor, elevating them to manager because we need one today and then spending the next two years trying to make them better at their job. I’d like to make people better at their job before they get into that particular position and then let them free and let them sail. So that’s kind of how I’ve always done it.

CLAIRE: I think preparing and training before the moment, that’s how you get someone hopefully sort of optimally ready. Seems to make sense in that situation.

JASON: Yeah.

CLAIRE: Thank you so much for everything you share. This has been a blast.

JASON: Likewise. Thanks so much for having me on. It was great.

CLAIRE: Yeah. You bet. Everyone, I’m sure if you’re listening, tuning in, so much to have learned from Jason as always. And yeah, I look forward to having you tune in on future episodes of Heartbeat. So, thanks again, Jason.

JASON: Thanks, Claire. See you.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.