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We do a quick check-in with Basecamp CEO Jason Fried about what he’s been up to since launching HEY in June. He talks about running the company as the pandemic stretches on, the importance of not making promises, and learning to swim.

The Full Transcript:

[00:00:00] Broken By Design by Clip Art plays.

Wailin: [00:00:01] Welcome to a bonus episode of Rework, the podcast by Basecamp about the better way to work and run your business. I’m Wailin Wong.

Shaun: [00:00:08] And I’m Shaun Hildner. This week, we are running two episodes. You heard David in our previous episode, and we checked in to see what he was up to. And now we are going to check in with Jason Fried, Basecamp’s CEO. This conversation sort of goes all over the place but it was really fun just to check in with the higher ups every once in a while. And Wailin, you popped into the conversation a little bit later.

Wailin: [00:00:30] I did. And I realized when I popped in that I hadn’t talked to Jason, for many months. The last time I really talked to Jason was when you and I interviewed him about the launch of HEY. So that would have been oh, gosh, when was that even? When did we launch HEY? June? It’s funny because he is my boss. You know what I mean? Like—

Shaun: [00:00:53] Yeah, and he’s in Chicago. He’s also someone like we would see, you know, three times a week maybe?

Wailin: [00:00:58] Yeah, I mean, it’s just this bizarre situation where we’re all at home or you know, working remotely and I don’t really leave my house anymore, except to grocery shop. Or yesterday, I went through the Dunkin Donuts drive thru, because that’s what passes for entertainment and the destination now. Yeah. It just really struck me when I hopped on the call to say hi to Jason, that I hadn’t talked to him for months and months.

Shaun: [00:01:22] Yeah.

Wailin: [00:01:23] I just hadn’t even heard his voice, you know.

Shaun: [00:01:24] And it was good to hear his voice. So now, listeners, you can hear his voice. Here’s my conversation with Jason Fried.

[00:01:31] Broken By Design by Clip Art plays.

Shaun: [00:01:39] Jason.

Jason: [00:01:40] Shaun.

Shaun: [00:01:40] How are you?

Jason: [00:01:42] I’m under a blanket, is how I am. So people understand that. That just I’m just trying to kill the echo here. I’m trying to—I’m in an echo-y room.

Shaun: [00:01:49] You’re not under a blanket for sort of emotional reasons I made you do this.

Jason: [00:01:52] No, no. Shaun told me to wrap myself in a blanket. Maybe you’re trying to help me. But I think it’s mostly to cut down on echo.

Shaun: [00:01:59] Little bit of both. Little bit of both.

Jason: [00:02:01] Yeah.

Shaun: [00:02:01] So where are you now? You’re not in Chicago, right?

Jason: [00:02:04] Currently, I’m out in California. So we’re… this whole this whole COVID thing has sort of encouraged us to try some new stuff. So my family is out here in California for a bit. We don’t know how long we’re going to stay. We’ll probably end up back in Chicago at some point here. But right now we’re out here enjoying the Southern California weather.

Shaun: [00:02:21] That’s exciting.

Jason: [00:02:23] Yeah. It’s feeling pretty good.

Shaun: [00:02:24] Yeah.

Jason: [00:02:24] It’s a little weird. I mean, it’s all smoky. Now it’s fine, but it was smoky for a while. It’s funny. Wherever you are, you always think some other place is better and you go this other place, and it’s better for a bit, then you find out what’s wrong with that place. And then you… Oh, I can’t breathe. That’s kind of a problem. But—

Shaun: [00:02:38] The grass is always greener.

Jason: [00:02:39] Yeah. But we’re doing good. We’re doing good.

Shaun: [00:02:41] Good. Good. So, I mean, things I’ve still been pretty busy at Basecamp. Is HEY for Work sort of what’s taking up most of your time?

Jason: [00:02:49] Yeah, so we’re finishing up HEY for Work right now. You know, we launched HEY personal, which we’re kind of calling now HEY for You. And then HEY for Work. So HEY or You, we launched back in June. And it was kind of a huge hit. And now we’re finishing up HEY for Work, which is the multi-user work version. So companies can get everyone on HEY inside their company, host their email at their own domain, collaborate on emails in different ways, stuff like that. So we’re doing that right now. And we’re planning on shipping that, not to everybody, by the end of the year. But like a collection of companies that are interested. We have a waiting list of about 10,000 companies now who signed up to be notified when we launch so we’re not going to ship it to all 10,000 in 2020. In 2021 we will, but the end of the year is going to be kind of like a hand-picked, select group of companies that sort of makes sense for for the first rollout.

Shaun: [00:03:44] I know I’ve talked to David about this. And I’ve heard you mentioned it as well, that one of the worst things you can do is make promises for the future. How much do you regret saying we will have HEY for Work out at a certain date when we launched a HEY for You?

Jason: [00:03:58] I regret it, publicly. In that making—There’s different kinds of promises and different kinds of deadlines. Public promises, I almost always regret, regardless of what they are. Internal promises and internal dates and deadlines, I think are incredibly helpful. They help focus us, they make sure things get done in a certain period of time. And then it helps you make trade offs. The problem with public promises is that they’re harder to move if you have to. Like, if reality strikes in some way that you truly just can’t get something done. We’re pretty good as a company. We’re quite good at really getting things done when we say we’re gonna get them done. But sometimes, things change. Like right now David’s on a sabbatical. That was not planned.

Shaun: [00:04:43] Yeah.

Jason: [00:04:43] When we made the HEY for Work promise earlier in the year, we were expecting David to be here. David’s not here for a few months, he’s taken some time off. There’s some other vacation time, some other sabbaticals that weren’t planned that are happening. There’s some other stuff that happened. We had some downtime, you know, with Basecamp, which took us off our focus on HEY for a bit.

[00:05:01] So, you know, internally, we would understand these things and go, okay, well, we didn’t hit our deadline because of these things that literally took us off our game. But externally, it’s harder to explain those things.

Shaun: [00:05:10] Yeah.

Jason: [00:05:11] That’s why I always regret it. And I also regret it because it’s more of a short term. It’s short term pain relief. When everyone’s asking for something, it’s really easy just to go yep, yep, later. We’ll have that later. And the easiest later thing is to say by the end of the year. It’s just this reflective period of time that you’re like, we can do anything in the world by the end of the year. So let’s just say end of the year. And it’s just it’s kind of an easy way out. And it’s better to say, to be honest, and be like, we’re going to work on this, this is absolutely our intention, we’re going to build this. We don’t know when it’s going to be ready. And that to some people that would let them down. But it just it’s the more honest answer. And I think that that moving forward, we kind of just stick to that.

Shaun: [00:05:54] Speaking of people taking sabbaticals, how’s it been working without David here?

Jason: [00:05:58] Oh, it’s such a relief. No, no, no, it’s, I mean, it’s hard. David and I have worked together for I don’t know, what is it? Like 17 years, 18 years, whatever it is.

Shaun: [00:06:09] 20 years, or something like that.

Jason: [00:06:10] And that means we make a lot of big decisions together. We don’t talk every day, we might even talk just once a week here and there, you know, it depends. But big decisions, it’s always fun to have, and healthy and helpful to have someone who’s mostly like-minded but also not always as your peer where can sort of battle some of the stuff out and get better outcomes when you have two points of view that are fiercely opposed in some case. That are also sometimes closely aligned, but just a little bit different.

[00:06:40] So I don’t have that right now. And of course, I don’t have the technical chops. I don’t I don’t have any technical chops, really. So, you know, we lean on David for a lot of a lot of that, of course. But you know, we don’t have a good company if someone can’t be out for a while. So I think we’ve managed quite well. And David’s able to come in for a week a month here and there if he needs to that kind of stuff. So he’s he’s done a little bit of that. And during that week, we got to catch up and sort of accelerated a few things and sort of compressed a few other things.

[00:07:12] So it’s been good, but it’s it’s been different. I will say that I’m looking forward to taking one of these. When David’s back, I don’t know when that’ll happen. When David and I were talking about this, him taking some time off, we were kind of reflecting on our own time off moments. We really haven’t taken—I have never taken a sabbatical.

Shaun: [00:07:30] Yeah, that’s what David was saying as well.

Jason: [00:07:32] Yeah, he hadn’t either.

Shaun: [00:07:32] You’ve both taken, like, a week or two here and there. But…

Jason: [00:07:35] Yeah.

Shaun: [00:07:34] Not like the rest of us that take you know, what, a month every three years?

Jason: [00:07:38] Yeah. I mean, when I had we had our kids, but that’s not a sabbatical. That’s just—

Shaun: [00:07:45] It’s different work.

Jason: [00:07:44] Yeah, different work. Yeah. So I haven’t really taken a month or two months off ever. So I’d like to do that sometime next year. But right now, I’m all in since David’s all out.

Shaun: [00:07:56] Yeah, yeah.

Jason: [00:07:58] It’s also a good reminder, frankly. No one’s that important that the company grinds to a halt. That’s not a healthy company, if the company grinds to a halt, if someone right go out for a few months. So it’s good practice for us to allow other people to make decisions, to offload some of these responsibilities on others.

[00:08:14] I’ve been trying to slowly do this over the last few years, which is just like, step back a little bit from day to day planning of things so other people have more practice and experience doing these sorts of things. And it’s just it’s a healthy thing to practice, so…

Shaun: [00:08:29] Are you good at that? Are you good at shutting work brain off?

Jason: [00:08:32] I have become better at it. It does take practice. I’m always thinking about things just because I like to think about things. I like to think creatively about opportunities and stuff we could be doing and how we’re doing certain things and how we’re implementing something and how we’re designing something and how it feels to a customer and how to tell the story. I just like that stuff. So if I think about that at night, here and there. It’s not—I’m not logging work hours. It’s just on my mind because I enjoy thinking about things like that.

[00:09:01] But I’ve gotten a lot better at just letting things happen. Even if the decisions that are being made aren’t the decisions I would have made. I’m much more okay with that than I would have been even three or four years ago. I think this is going to be especially healthy for David, too, because David likes to make a lot of decisions, too. Makes a lot of big decisions. And I think it’s just… it’s good to go, you know what, hey, Jeff, you’re in charge now. Jeff’s just basically taken on David’s role while while David’s out and Jeff might make some decisions that David wouldn’t make, but that’s super healthy for the organization. We have to be able to let other people make great big decisions, important decisions and get practice making those decisions. Otherwise, when the moment comes when they really need to make one and they haven’t practiced, it’s gonna be harder to do that. So I feel good about it.

Shaun: [00:09:47] Good.

Jason: [00:09:48] Yeah.

Shaun: [00:09:48] So we used to do these, what did we call them? Last week with Jason Fried or something, you know, these little check ins of what it was like to be a manager. And I don’t think we’ve ever talked about this and I’m not sure why. But what has it been like being a manager as the world is in such turmoil right now. Sending everyone home for good. That was probably a little easier because we were remote anyway. But I’m just curious on your thoughts of how are you dealing with 54 people and the crazy emotions that we all have to go through?

Jason: [00:10:22] Yeah, I mean, we’re used to the work side of it. Right? It’s pretty much how most of us work most of the time, but this is this is very different because of the external pressures. The stuff we can’t control and people’s emotions and mental states. And especially for parents with kids at home. I have some experience there. So it’s hard. It’s really hard. So I’m trying to keep in mind as best I can. And I probably haven’t been very good at this. But everything’s, we have to dial back our ambitions a bit, which is tricky, because we’re trying to launch this new thing, HEY for Work.

Shaun: [00:10:59] Because you made promises.

Jason: [00:11:00] We made promises, right? And, I mean, people ultimately understand but it also doesn’t feel good to break them, you know? So we have this ambitious aim here. We’re trying to launch this thing, which we will, but no one’s at 100%, really. I mean, maybe someone is, I don’t know, most people are not, though. And we just have to remember that.

[00:11:22] We also have, in the summers, we do four day weeks, but we had to cut that short this year, because of the HEY launch. And also usually people go away on the weekends, and no one could go anywhere this summer. So it’s just a weird, it’s been a strange, weird year. And I think the other thing is, is that I kind of, I miss everybody in a different way. Normally we would have had a meetup in the spring. And we’d be having a meetup in a month.

Shaun: [00:11:47] Yeah.

Jason: [00:11:49] Physical meeting.

Shaun: [00:11:49] We’ll be coming up on our second missed meetup, yeah.

Jason: [00:11:51] Yeah, it’s our second. I feel like missing one is like, okay, like, I missed a number of years ago, I was sick, and I kind of missed most of one, right? It’s like, all right whatever, I’ll see someone—I’ll see everyone in a few months. Now, it’s like, basically we won’t have seen each other for a year. We have some new employees we’ve never seen in person.

Shaun: [00:12:07] Yeah.

Jason: [00:12:07] And that’s kind of strange. So it’s just a strange time. And I think just being as as reasonable as possible, given the circumstances. And also given the fact that we do have a business to run. And we do have to do things. And we do have to make progress. We have to do all those things. We can’t sit around and not do that stuff, either. So it’s just kind of figuring out how to balance all this as best we can. And I’m sure we’re not doing it as well as we could. But hopefully, we’re doing a pretty decent job.

Shaun: [00:12:35] Yeah, yeah. I’m trying to think what else is going on in the company? Can you talk… this is more of David’s thing, the App Fairness Coalition?

Jason: [00:12:42] Oh, yeah.

Shaun: [00:12:43] I don’t know if you want to mention it.

Jason: [00:12:45] Yeah, sure, sure. We joined it with a number of other companies, Spotify, Epic Games, Match Group, I forget who else was in it. Oh, ProtonMail. There’s some others, I’m sorry, the ones I’m forgetting. But there’s a number of groups, companies that got together that decided to basically create this coalition that stands for App Store fairness. And all we’re asking for is—And there’s, if you go to the site, I think it’s, I have to remember the URL.

Shaun: [00:13:14] Really quick, that URL is

Jason: [00:13:19] There’s a list of issues, there’s basically 10 issues that we all are in favor of which is mostly around choice, that we, as developers, we expect to be able to service our customers our own way, to be able to communicate with our customers our own way, to not be unfairly treated by the platform owners who also compete with us directly on certain products, that kind of thing. There’s this really long list, it’s a good solid list, it’s not too long. And it’s not esoteric, it’s things you could probably understand as a business owner. Like, yeah, this would be… I would expect this to be what I would expect, too, from a platform.

[00:13:53] So we put this out there, there’s some money behind it, it’s kind of like in the sense a sort of a lobbying group in a way to encourage, and to put a little bit of pressure on these companies like Apple, primarily, and Google, to make some changes to make it fair. AndApple and Google talk about how great the app stores are, but they’re not so great for a lot of developers. And I think developers are finally beginning to speak out against this. And hopefully, this group provides some cover because there’s some big brand names in it, for other people to join the movement, essentially, and speak out on what they feel might be bullying tactics, or strong arm tactics, or simply sets of rules that are really outdated and antiquated and unfair. And so, we want to get behind this. So we’re a founding member and we’re gonna promote as best we can.

[00:14:40] It’s just, it’s time. It’s come to this basically, is the way to think about it. This is not Plan A, you know, like we hope—

Shaun: [00:14:48] We didn’t set out to attack Apple.

Jason: [00:14:50] No, not at all. And we also didn’t set out to join a coalition. This is not our kind of thing. This is not typically what we do. We’re a very independent minded company. We do things our own way. But in order to have things change, I think we needed to do this. I’m hopeful about the impact it may have long term. I don’t expect anything to happen in the next few weeks kind of thing, although there’s some lawsuits going on. But… and we’re not involved in lawsuits. I should just clarify that.

Shaun: [00:15:17] Yeah, yeah.

Jason: [00:15:18] It’s between Epic and Apple and stuff. We’re not involved with that. But hopefully, it moves the needle and things start to change.

Shaun: [00:15:23] Yeah. Well, it looks like someone else just got on the line.

Wailin: [00:15:27] Can you hear me?

Jason: [00:15:28] Oh, my gosh, I recognize that voice.

Wailin: [00:15:30] I didn’t know if… I’ve never joined a call in progress before in Zencastr, so I didn’t know if it would connect. But I guess you can just have someone join in the middle. Hello.

Jason: [00:15:41] Are you still holding up in your little home studio under the stairs?

Wailin: [00:15:44] Yeah, I get so many questions about it. Well, I’m now on like, hours and hours of Zoom calls in the evenings for all like, various extracurriculars.

Jason: [00:15:52] Yeah.

Wailin: [00:15:52] And I get so many questions about it. People are like, where are you? I’ve gotten asked if it’s a panic room. If it’s a space capsule. People are fascinated by it.

Jason: [00:16:04] It has this sort of NPR Tiny Desk potential. Like—

Shaun: [00:16:08] It does, yeah.

Jason: [00:16:08] You need to have something special like Wailin Under the Stairs or something like that. You’ve got to take advantage of this weird physical place that you’re in? I think it’d be kind of fun.

Shaun: [00:16:21] So we I think we covered most things right. We covered HEY for Work, the App Fairness Coalition, what’s life without David like—

Wailin: [00:16:27] What is life without David, like?

Shaun: [00:16:30] You’ll have to listen to the episode, Wailin.

Wailin: [00:16:31] Okay.

Jason: [00:16:31] Yeah, Wailin. Wait your turn.

Shaun: [00:16:35] What are you doing for fun? What are you excited about?

Jason: [00:16:38] Like I said, we’re in Southern California at the moment. So we’re really just kind of exploring around, which is kind of fun. Seeing, even just like, wow, I don’t recognize that plant species, that’s different. Everything here has spikes on it and it’s sharp and very vibrant and green. We’ve been just trying to get out to the beach and just kind of really take it easy, take advantage of the place we’re in. This special little place we’re in, so we’ve been doing that.

[00:17:03] And I’m learning how to swim. I don’t know how to swim really.

Shaun: [00:17:05] What?

Jason: [00:17:07] Yeah, I mean, I can like get to the other side of the pool. But like, I don’t really know how to swim.

Shaun: [00:17:11] I had no idea!

Jason: [00:17:13] Yeah, I mean, again, like, I would survive in a pool, but I would not survive in a lake. I would be dead. So it’s kind of… I’m starting, I’m going to take some lessons soon to really learn. I want to—the ocean has always scared the hell out of me. I’ve had some friends, actually, in college who died surfing in the Pacific Ocean. And like, it’s always freaked me out. When I was going to camp, like overnight camp. I was on this little sailboat and I got trapped. Like it flipped and got trapped. And I’m like, I’m not a big fan of the water, let’s just say. But, I kind of want to overcome that fear. So I want to take some ocean swimming lessons and just kind of get used to it. Which is like a big thing for me that I’ve never really dared get close to the ocean in that way. So that, I haven’t started that yet, but I’m making my way there.

Shaun: [00:17:59] Oh, that’s awesome.

Wailin: [00:18:00] That’s really neat. I mean, I feel like learning something like that, as an adult is so daunting for most people. So I really respect that.

Jason: [00:18:07] Yeah. It is. I’m, well, I may not go through with it. But like—

Shaun: [00:18:12] Didn’t we talked about making public promises, Jason?

Jason: [00:18:18] We were at the beach yesterday, and I was watching some people who were just so at ease in the ocean.

Shaun: [00:18:25] Mm hmm.

Jason: [00:18:25] And I’m like, I can’t get anywhere close to being that comfortable. Like, it seems like an impossibility. So I’m really curious to see what, let’s say six months of working with someone who understands the ocean, like who grew up around here, who really understands it, and like gets that it’s dangerous, but also wonderful. And as long as you kind of can read it, you kind of know what you’re doing and you’ll be right. I’m just so far away from it. I can’t think of anything else really, in my life, that I feel like I could not do at all. Okay, that’s not true. I couldn’t sing opera. Like there’s things I couldn’t do, right?

Shaun: [00:19:02] Sure.

Jason: [00:19:02] But physically, I feel like I’ve got a pretty good handle on the world. And this is just something that’s so foreign to me. So I’m curious to see if I can pull it off. And if I actually go through with it all the way.

Shaun: [00:19:12] Yeah, that’s really exciting. What a fun thing to check off the list.

Jason: [00:19:13] Yeah.

Shaun: [00:19:15] I actually kind of really liked these meandering episodes we did with you and David.

Jason: [00:19:18] Yeah, these are fun. These are fun. I’m up for doing… I’m not sure I’m up for the towel over my head very frequently, but I’m—

Wailin: [00:19:26] We’re gonna ask you to put like a progressively heavier duvet over your head each time you come back on.

Jason: [00:19:30] Sweating. Yeah, I am literally, it’s probably 106 degrees under this right now. So it’s um, it’s kind of fun. Yeah. You get delirious and say some weird stuff. But cool. Yeah, this is good anytime I’m around.

Shaun: [00:19:45] Awesome.

[00:19:47] Broken By Design by Clip Art plays.

Shaun: [00:19:49] Rework is produced by Wailin Wong and me, Shaun Hildner. Music for the show is by Clip Art.

Wailin: [00:19:55] You can find our show on Twitter at @reworkpodcast and if you want to check out the the website for the App Fairness Coalition that Jason mentioned, again, that URL is And we will have more about this later. I think we need to wait for David to come back from sabbatical before we do more on that front. But definitely something we’ll bring you an episode on later on.

[00:20:31] Can I tell you that yesterday, I went to Dunkin Donuts. And I ordered… sorry, lately, all I do is tell you about going to fast food restaurants and having very small things go wrong with my order.

Shaun: [00:20:44] You know this is right up my alley.

Wailin: [00:20:45] But I ordered a pumpkin coffee. And they’re like, we don’t have pumpkin. And I was like [gasp!] I was like, do you know what time of year it is?

Shaun: [00:20:55] Tomorrow is October. At the date of this recording, tomorrow is October. How can you not have pumpkin spiced everything?

Wailin: [00:21:00] I was shocked. But then I thought maybe they just ran out of pumpkin, because I went at like 3:30. Maybe by that time of day they’re out of pumpkin syrup because so many people have already been by ordering pumpkin things.

Shaun: [00:21:14] Right.

Wailin: [00:21:16] But after the spicy nugs misadventure at McDonald’s over the weekend, I was just feeling a little bit bummed.

Shaun: [00:21:22] I’m so sorry.

Wailin: [00:21:22] It’s like, what do I have left? I just want to go through a drive thru to get the thing I ordered, you know?

Shaun: [00:21:28] Uh huh. I know exactly the feeling. Well, the world’s falling apart.