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Less Business, More d20s

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Matthew Vincent, a member of Basecamp’s Ops team, spoke at Nomad City 2019 about life as a remote worker. Close your eyes and pretend you’re in the Canary Islands as you listen to this audio version of Matthew’s talk.

The Full Transcript:

[00:00:00] Anyone You Meet Normcore Remix by Clip Art plays.

Shaun: [00:00:02] Rework is brought to you by Basecamp. Basecamp is the all in one app for managing projects, working with clients and contractors, and communicating with your team no matter where in the world they are. Learn more and try it for free at

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

Wailin: [00:00:21] Welcome to Rework, a podcast by Basecamp about the better way to work and run your business. I’m Wailin Wong.

Shaun: [00:00:25] And I’m Shaun Hildner. Last November, Matthew Vincent, a member of the Basecamp Ops team was invited to speak at Nomad City. Nomad City is an annual conference in the Canary Islands that focuses on working remotely.

Wailin: [00:00:39] Sadly, we did not get to go to Gran Canaria for this conference, but Nomad City was kind enough to let us use Matthew’s talk on the podcast, so we’re going to play that for you now. A quick note, Matthew was working with slides which he references occasionally. The talk is still valuable without the visuals, but for the full experience, if you’re curious, you can go to and pay a fee and you can access their full library of talks including Matthew’s.

Shaun: [00:01:04] And another quick note, Matthew makes reference to the title of his talk, which is Less Business, More D20s, which is actually a name that I suggested as a joke based on the fact that Matthew plays Dungeons & Dragons with me occasionally.

Wailin: [00:01:20] And what is a D20?

Shaun: [00:01:21] A D20 is a 20-sided die used to make most of your rolls.

Wailin: [00:01:25] Do you happen to have one tattooed on your forearm?

Shaun: [00:01:27] I do. Let’s get into this talk.

[00:01:32] Broken By Design by Clip Art plays.

Matthew: [00:01:39] Today we are going to talk about vans, pie charts, cleaning, Christmas, goats, [Hartlepool?], Italian cheese, bicycles, stickers, GitHub, books, and shameless promotion. We good? All right. So let’s get started.

[00:02:00] So I first came up with this title and I decided it was crap. So I decided to go with this one instead. So forget that original one. We’re going with Less Business, More D20s. Who knows what a D20 is? All right, you guys are my boys and girls. Hopefully there’s some girls that know what a D20 is, as well.

[00:02:20] The legend of Ben Discoe. Anybody know who Ben disco is? So there’s this great Quora thread that if you look this up and there is going to be the link at the bottom that will tell you a little bit more about who Ben Discoe is. Which Googler holds the record for living at Google HQ, name and or title dates, living working at Google and backstory. And are there any policies to encourage or prevent this? So current record is held by Ben Discoe who lived 13 months in a converted van in the parking lot of Google HQ between 2011 and 2012.

[00:02:58] So I looked up Ben Discoe on LinkedIn, this is how long he worked at Google from November ’11. It’s from November 2011 to November 2012, working on the self-driving car project. So I was like, alright, this is interesting. Who’s the next on this list? So we have Matthew J. Weaver, staff site ecologist. Lived there 54 weeks in an RV behind [pi?]. I mean this is all internal Google stuff, but he kind of broke my mold on that. He worked there for nine years. I was like, all right, so maybe there’s not much of a correlation there.

[00:03:32] I really wish I know who this guy was though. Anonymous. He lived entirely inside of Google for 13 months between nap pods and beanbags and meditation rooms and massage rooms and conference rooms. Every one with a sofa and without windows. I would love to know how long this guy actually lasted there.

[00:03:56] We look at turnover rate, the churn rate in businesses right now, it’s actually kind of shocking when you look at a place like Google. You’re like, man, the salary is good, the benefits are good. You eat for free, you can apparently live for free. They’ll do your laundry. They have in-house doctors like what other benefits could you possibly want? Why would you ever leave Google? Yet we see a rate, an average turnover 1.1 years.

[00:04:20] I know this data is a little bit outdated and some people kind of question, is that really the case? But these are pulled in from people’s LinkedIn profiles, whatever it is. They’re generating this data and apparently people aren’t staying around at Amazons and Googles and who knows what else we got going on there.

[00:04:34] So the question is, what’s going on? Why aren’t these benefits enough to keep people at the jobs that they’re in right now? So these are some of the things that people are looking for when they’re looking for employment.

[00:04:50] Transparent leadership is one of the things that people want the most. That’s hard to get when you’re in these big companies. You know, your CEO is so far removed from you. Occasionally you might sit next to Steve Jobs at lunch, but you know, it’s like you’re not getting that sort of transparent leadership in there.

[00:05:07] Giving back to the community. I think a lot of things that we’ve heard today, people talking about sustainability, they’re talking about new models for work. They’re talking about restructuring the way that we even think about work. And giving back to the community becomes a huge part of that.

[00:05:22] Something that shares my own values and allowing me to learn new skills, a mission I believe in. Obviously, if you work for something that you know you’re not just selling a product, but it’s actually like I’m making a difference in the world around me. Becomes something that’s really huge.

[00:05:38] Workplace flexibility. Interestingly enough is not as high on there as I thought it would be, but it’s still there, people want that.

[00:05:46] Cutting edge technology. So, I guess thrown some buzzwords, AI, machine learning, whatever, blah blah blah. And we get some of the things that are going in there. Flexible work hours, working from home. This is the sort of things that are most important when people are talking about flexibility and the jobs that they are actually looking for.

[00:06:05] Remote work is surprisingly fairly small on that list when people are thinking about flexibility, although, again, I say, work from home, so I think there’s already a problem. And when people are thinking about remote versus not remote work.

[00:06:20] And it’s actually worth taking time to talk about, because of course we have this concept of being a digital nomad. Like, hey, I’m working from Gran Canaria today and next week I’ll be in Madrid and the week after that I’ll be in Berlin. There is that sort of nomadism in there, but at the same time remote work might actually just mean you’re working from home and you are staying exactly where you’re at, but you just have a different office set up.

[00:06:47] And that’s been my story. My whole life, I have essentially done that except for one year and I had to go into an office every day and punch the card, and that was when I lived in Italy.

[00:06:58] So the top benefits and perks, what are the things that people are looking for? And again, I think it’s really interesting that the self-development is something that people want. Education benefits. Give me some tuition reimbursement. Like let me continue to learn and improve myself.

[00:07:12] And you know, shameless plug for Basecamp, one of the things I love the most is we have an education allowance that we get to use every year. And it does not matter what you use it on. They’re not saying like, yeah, I want you to take classes in your role at Basecamp. No. People have gotten their pilots license off of that and they now can fly a plane thanks to Basecamp’s education program on there.

[00:07:34] Health and wellness. Obviously that’s huge in the US that probably becomes a bigger deal when you think about health insurance and things like that. But outside of it, it might be something as simple as a company saying, hey, we’ll pay your gym membership, go buy yourself a bike, go get something, get a massage. It’s on us. Things like that. People want it, they care about it, they want to feel like caring for themselves is actually part of the company’s agenda.

[00:08:05] And I think it’s really interesting that actually the volunteer, and again this whole social responsibility is a fairly big chunk on there. I mean it’s around 13 and a half percent, it’s not small. But people care enough about that, that that’s showing up as a benefit or a perk as part of their employment.

[00:08:20] When people are evaluating these jobs, obviously no surprise that pay and benefits are pretty high on that list. But flexibility is in there as well. Career advancement, learning, ethical reputation, wellness programs. I mean these are all pretty much sat on the same level of that bar graph there and it’s just amazing to think that these are the factors that people today are currently thinking about when it comes to deciding where they want to work next.

[00:08:48] This tweet came out not that long ago, 25th of August, 2019. “I still have no idea how people can work a full time job, cook dinner often, exercise regularly, enjoy weekends, keep the apartment clean. Seems basic, but I can’t consistently do it.”

[00:09:11] One of the replies in this is actually really poignant. Current full time, 40 hour-a-week jobs aren’t designed for single people to do this. They’re post-war relics, depend on the unpaid labor of a spouse for cooking, cleaning, shopping, et cetera. You’re not deficient for not being able to do it yourself.

[00:09:32] We are coming into, and this is what I love what’s happening right now. There’s a shift. There is a massive shift in the way that we’re thinking about work, and one of the things that I bring in like my experience as someone who’s worked remotely most of his life, it’s just thinking about jobs in a different way. Thinking about how we work in a different way. Working remotely has a whole set of implications, but this is a massively broad conversation about what does it mean to be an employee or an employer in the 21st century, in the world that we live in today and what can we do with that sort of thing.

[00:10:09] Interest in remote work. We see this as a one of these lovely Google trends. You can Great place. Have fun with it. But so this is interest over time of people punching in the term remote work. All right, so kind of grows, grows, grows, grows and it’s really starting to increase quite a bit more.

[00:10:27] Now these peaks are really interesting. Happens around December every single year, which actually makes me think this has more to do with people getting new TVs and trying to figure out how the remotes work. So that might be part of it. I put in remote jobs as well though, to be honest, the trend is pretty much the same, so it is there, but even if like, so maybe this has to do with televisions, but maybe it also has to do with that time of the year when people are reevaluating what matters the most. Maybe they’re spending time with families or maybe they’re not spending time with families because they’re stuck in the office and they’re saying like, why am I living in this sort of way?

[00:11:10] There’s this article in Financial Times that is talking about remote work as well and had a lot of different comments on there. And you know, one of the ones that people always think about is remote work good for the employer. The real question is, is how good is this for the employees? On one hand they can move to more affordable locations. On the other, there’s a problem of isolation and increasingly blurred boundaries between home and work that can begin to feel unhealthy.

[00:11:36] We think about distractions. I mean, how is it, you’re sat at home on the boat in this case and you know you’re sitting in YouTube doing whatever because no one’s looking over your shoulder.

[00:11:48] Work from home, they said. You’ll be more productive, they said. And how many of you have lovely cats that are just going sit on your lap? I don’t have a cat. I don’t have a pet. I wish I did. But yeah, this sort of thing begins to happen. You know, the classic meme. What my friends think I do, what my clients think I do, what the government thinks I do. But I actually really love this last image here. That is one of the pictures and massive benefits. The fact that family can be part of that. You do have the ability to be actively part of your child’s care in a remote work situation.

[00:12:24] It is one of those added distractions, but it does become something that’s a lot more plausible when you can just say, Hey, I’m going to go for a walk with my kid for 15 minutes and it doesn’t mean that you have to drive an hour home from the office to do that. You can be spontaneous. You have that opportunity to be inside of there.

[00:12:39] So I want to talk a little bit, I mean obviously I’m preaching to the choir here. Can I get an amen?

Audience: [00:12:44] Amen!

Matthew: [00:12:44] Yes. I am preaching to the choir here. I think you guys all agree with some of these points about what remote work is, or some of the benefits that we can get from it. But I also want to talk about my own experience, especially since I’ve joined Basecamp two and a half years ago. About how you survive as a remote worker. What are some of the challenges you see, where can we go with that?

[00:13:06] Basecamp is an entirely remote company today for the most part. There’s pretty much one guy who goes to the office. Shaun, this is for you. I’m giving you a shout out. The one guy who goes to the office, because I know he’s going to listen to this later on. So Shaun, love you man.

[00:13:22] But you know there’s a handful of people, even the ones who live in Chicago and are a short walk from the office are still remote workers. They oftentimes prefer to be at their own homes as opposed to making that sort of separation, walking and going into the office.

[00:13:37] So the one thing I would say above everything else as a remote worker, own it, own everything that you can do. And by that I mean you share everything. Everything about your day, how you’re feeling, what’s going on, what you’re doing. At Basecamp we have automatic check-ins that run every single day and sometimes weekly. So every day I will get prompted at 4:30 in the afternoon. What did you work on today? Every Monday at 9:00 AM I get prompted. What will you be working on this week? Seems simple. These are hugely crucial.

[00:14:13] So for example, this was one of my daily check-ins not that long ago. Something I was particularly proud of. I’ve been recently working on our fail-over tooling. So emergency situation, you run these scripts and that saves us, hopefully. And we had… this thing was like super slow before. This is in our staging environment, so that’s actually, if we ran this in production it takes quite a bit longer. But you know, I managed to get something that took 140 seconds before to run only in 83 seconds, which is are just like, that was awesome. I was super proud of that. So this ended up being in this really long check-in that I was like, hey, check this out. I’m really excited about that.

[00:14:52] And for example, what would I be working on this week? This is redacted so hush, hush, quiet, quiet. But on the other hand, you know, simply saying, hey, I’m going to be out on Friday because I’m going to be doing a presentation at a conference, and something that I’m excited about, lets people know what I’m involved in, what I’m doing at the time.

[00:15:12] On the other hand, this was an excerpt from another one of them that talked about something I was struggling with. I’m continuing to wrestle with some of the strangeness that I’ve run into with getting a post-flight check to run. So we have these series of just information that after you run something you should give this feedback and saying, this is working. The state of this is where we expected it to be and they weren’t working. I spent like two or three days working on this thing, being frustrated with it, picking it up, leaving it and setting it aside, doing whatever.

[00:15:40] And it wasn’t exactly like a gating issue, not something that was stopping me from working on it so I could pick up other parts of the project at the same time. But it was really frustrating that something so simple wasn’t actually working. And so having that freedom to express to my colleagues that I’m frustrated with something that I’m working on that time is absolutely necessary.

[00:16:01] Now, of course in a real sort of office, well, “real” office environment, in a traditional office environment, people can see when you’re frustrated. You all go walk to lunch together and like, oh dude, what’s bothering you? It’s like, oh man, I’ve been working on this problem for the last few days and just can’t seem to get through it. And sometimes you get those spontaneous conversations that can get you somewhere and help you break through that. Part of this point of communicating everything that you’re doing, oversharing, is because sometimes those conversations can also grow when you’re sharing with your colleagues how that sort of thing is going.

[00:16:37] I also, this is not something that’s automatically prompted in our system, but I have begun doing this, is that the end of every week I will write a Heartbeat. We use Heartbeats as part of our cycles of Basecamp, but each week I will just simply say, hey, this is what’s happening. This is what I’ve done this week.

[00:16:53] So it’s like Monday, I’m writing, hey, this is what I’m going to do this week. Every day, this is what I’ve done today. End of the week, this is what I ended up accomplishing this week. I have roughly about three hours of overlap with the rest of my team on a daily basis. So they don’t see me. We don’t have the conversations that they themselves have.

[00:17:15] So there’s eight on my team that work in DevOps because I don’t work in insurance and this is the way that they can know what I’m doing. They have six hours roughly amongst themselves. So they have a regular chat happening in one of our Campfires. So they have those sort of spontaneous informal conversations. I don’t get that with them. So communication becomes really, really important for them to know what I’m working on, for them to know that I’m not just sat cruising down the canal every day on the boat and not actually doing anything. So that’s the way that we get that kind of information on there.

[00:17:48] Communication is also how we build our social relationships in Basecamp. This is, for example, just a handful of the questions we have. Again, regular check-ins that are automatically showing up every day. What did you eat for lunch today? What did you do this weekend? What’s something you recently learned or discovered? Show and tell. What are you reading? And you can see the different frequency. So this is the first Wednesday of each month at noon. You can talk about what you’re reading. This is every Thursday. This gives you the opportunity to just talk about did you learn something cool this week that you’d like to share with the rest of the company? This is every Monday. Obviously after your weekend you can post and tell everybody what’s something interesting you did that weekend and what did you have for lunch today?

[00:18:32] So for example, after my trip to Hartlepool, posted this up there and it was just saying like, hey, this is what I did. I watched my parents watch birds for a weekend and showing like, yeah, here’s pictures, things like that. And it’s this awesome variety of things and it’s the way I get to know what my people are doing. Like, my colleagues, my work mates, I’m part of their lives socially at the same time. Even though I live in the UK and most of them are based in the US, it’s a way that we can bond over life.

[00:19:08] This is the salad that I had in [inaudible] the other day. A wonderful burrata salad with toasted pecans, I think it was, and this sort of smoky pesto sauce in there. Absolutely fantastic. And you know, you can tell there’s a bunch of foodies in our workplace cause they’re just like, yes please. Oh my God, this is amazing.

[00:19:30] But again, this is a way that we can bond together because they can see like, hey, we love to talk about food, let’s get that conversation going. Let’s make sure that we’re not just talking about work, but we are talking about these things. Again, when we work remotely and as Basecamp, as a company, we’re involved in each other’s lives and these are the things that we lose by not being in the office together. It’s not that spontaneous moment of like, hey, let’s go grab a bite to eat together. And we walk down the block to some restaurant and share one of these salads. No. Instead we have to do that through the communication that we have online.

[00:20:03] One of the other beautiful things that happens when you’re working remotely is that ability to spontaneously get out and do something.

[00:20:11] I love cycling. Road cycling is my thing. Obviously I haven’t been doing it enough lately as you can see by the size of my belly, but it is, like, that’s my passion and I have that ability that on any given moment I can just drop a message and I say, you know what guys? I’m off to grab a quick ride and done. No problem. And I can do that anytime of the day and it’s not the sort of thing of like, oh, I then have to worry about, oh man, yeah, I got to get back into the office. No, I’m free to do that and take the time to do whatever I need for my own sanity.

[00:20:43] This is one of the stickers that Nomad City has produced and I absolutely love it. This is one of the other beautiful advantages to this sort of shift in thinking about work is simply working from places we love. Traditionally and traditional models of work has been us having to give everything, give ourselves, gives our lives to the companies. That means you move to the offices, you move to where they’re at. So you know you get all these big stories, oh yeah, you know, relocation packages, I get a whatever. So much money to go move to some city that maybe you’ve never been to before. But no, why not be in a place you actually love to be and do the job you want to do. So I think it’s absolutely one of those beautiful concepts that comes about it.

[00:21:30] I want to give you guys just a little bit more information. So Basecamp’s handbook is open source. You can go onto GitHub and open up our handbook. A lot of the things that I’ve talked about, they’re all in there. So check it out. New book that they just released that talks about the way that we work. The cycles that we do is Shape Up and you can get that on there as well.

[00:21:50] Speaking of books, you know I’ve read these guys’s books way before I ever did it so I’m not calling this a shameless promotion because I love it. This is half of what’s inspired me to work the way that I have before. You know, Rework is one of the really famous ones, but for those of you interested in remote work, if you haven’t read this book yet, you definitely should. So, grab their book read their perspective on remote. They’ve been doing it certainly for quite a while.

[00:22:18] More recent ones, I already mentioned Shape Up, but It Doesn’t Have to be Crazy at Work, which again is challenging a lot of these sort of traditional models of doing business that we just simply don’t need to be doing anymore.

[00:22:28] And shameless promotion time. If you’re not using Basecamp, it’s maybe something you want to think about. When you talk about tools built for remote collaboration, Basecamp is one of the ones that we do. And I have to be honest with you guys, I’m incredibly privileged because I work at a company building software for project management focused on remote work and we use our product to build our product. So it’s pretty awesome. It’s all in one place. Everything that we do, everything that we use, it’s right there.

[00:23:00] If you want to, you know, if you’re a freelancer and maybe you don’t need to be paying 100 bucks a month for the whole suite, we just launched Basecamp Personal, so, free. You can use that and it’s a great tool. You get some limited stuff in there, three projects, 20 users, 10 gigabytes, but it would be a great place for you to try that out. And again, it’s a company who we’re all working remotely, we feel your pain, so we’re trying to answer and solve some of those problems. Thank you very much and feel free to reach out if you ever need to ask me any questions.

Announcer: [00:23:40] We have time for some questions I think, yeah?

Matthew: [00:23:44] Sounds good. I might even answer some.

Announcer: [00:23:48] I know you will. Of all the, I just want to ask this, of all the places you could live on a boat, why did you choose to live on the Thames?

Matthew: [00:23:55] So Danny actually got it wrong. I don’t live on the Thames.

Announcer: [00:23:58] Oh, man.

Matthew: [00:23:58] I live on the Grand Union Canal just outside of the Thames so I could take my boat onto the Thames. I don’t, but like the kind of bigger question is why do I live in the UK when I could live in Spain? And part of that is the boat adventure is awesome. The UK has something like 4,000 kilometers of canal that you can explore in the boat. It’s great fun. And it’s a cheap way to live. It’s an interesting way to live. [00:24:29] And previous to Brexit I was really excited about the idea of getting British citizenship, but now with Brexit on the horizon, it sort of screws my plans cause then as like, hey, British nationality, I could just move back to Europe after I have that and not have to worry about getting visas. Yeah, totally screwed by that. Announcer: [00:24:43] It’s almost like being an American.

Matthew: [00:24:46] Exactly.

Announcer: [00:24:47] How many hours a week do you dedicate to read, shared status updates? And just an extension of that, how do you know that that time you’re spending is valuable? I think it’s a great question.

Matthew: [00:24:58] Yeah, no, it is fantastic. So for me to actually like write those, it doesn’t take a lot of time, but sometimes it’s a great way to just finish off your day. So I make sure that I leave probably at least half an hour at the end of my day to yes, I do know what real football is, soccer. Anyway.

[00:25:17] So yeah. So I leave about half hour every day to write my updates and it’s a great way to decompress, to make that transition from work to no longer working because it’s reflective. It’s a time to do that. And at the same time, the longer ones are doing that Monday where I’m writing about what I’m going to do for the week. I may leave myself, you know, a bit more, 45 minutes to write it up. Sometimes, it’s super quick cause I know exactly what I’m doing. Sometimes I need to have that time to think about it. And then the end of the week, sort of a Heartbeat that I’ll write that might take a little bit more as well cause I need to reflect back on everything I did, reading everybody else’s updates, that’s a selective thing. I obviously I’ll read everything that my team posts or teams that are related to the work I do.

[00:26:00] And so sometimes it’s just scrolling through stuff and saying, oh, this one I need to read, this one I don’t. But again, it’s the freedom to leave yourself as much time as you need to. So that may be hours a week sometimes and sometimes it’s not.

Announcer: [00:26:12] Yeah, I think, and it really hits this question on the bottom, too. I work at a small nonprofit wearing five hats. Using our time efficiently as remote workers. It seems like we’re always doing something and we’re always productive. But being selective and being choosy and knowing when to say no is one of the real challenges.

Matthew: [00:26:29] And we’re fighting the whole idea of busy-ness at Basecamp. Busy used to be this sort of thing. It’s like a badge of honor. Don’t be busy. Like that’s number one. Don’t be busy. Choose what you want to put your time into.

Announcer: [00:26:41] Is there a word you use for that? Is it be productive? Don’t be busy? Have a high output, so on and so forth? Is there a phrase?

Matthew: [00:26:47] No, we don’t have a phrase. Our phrase is work can wait. So, you know, but it’s like busy-ness is not healthy. It doesn’t do anything for us. So trying to find ways to avoid that. Work shouldn’t be something that consumes your life, so.

Announcer: [00:27:02] The real football question, Hartlepool, United?

Matthew: [00:27:06] No, I’m a… honestly, I have two teams I follow. They’re both Spanish teams, so Valencia and Barcelona, so.

Announcer: [00:27:15] You can’t do those two. It’s just, they’re right next to each other. How about the 32-hour, four-day work weeks during the summer? Why not all year round? And what do you do with people in the Southern hemisphere?

Matthew: [00:27:25] Yeah, so the people in the Southern hemisphere still get the same summer. So yeah, they’re winter. Because we all do it at the same time. So we do… yeah, whoever grabbed that, great, great observation. So summertime’s roughly from about May through September, we work four-day work weeks. And part of that motivation is that we got people with families. Take that time, spend that time with them. It can seem like it interrupts productivity, but it’s amazing. You get a lot done on those four days, does that extra day really matter that much?

[00:27:57] And especially when you think about, you get a three day weekend, you’re spending it with your family, you’re rejuvenating yourself in many ways. And so you come back and it’s like Monday, you’re like, yeah, come on, I’m ready to do this. Or you’re diving in. So it does… it is a great way to just kind of keep yourself on fire. And yeah. Then the rest of the year we’re back on normal schedule. So five-day work weeks, ugh.

Announcer: [00:28:20] Horrible.

Matthew: [00:28:23] Horrible.

Announcer: [00:28:22] Matthew Vincent, thank you so much.

Matthew: [00:28:23] Thank you, everybody.

[00:28:26] Broken By Design by Clip Art plays.

Shaun: [00:28:28] Rework is produced by Wailin Wong and me, Shaun Hildner. Music for the show is by Clip Art.

Wailin: [00:28:38] You can find Nomad City at and we will link to that in the show notes along with a link to their Vimeo page where they have all of their most recent talks available for a fee.

[00:28:50] Special things to Nacho Rodríguez of Nomad City for letting us air Matthew’s talk on this podcast.

Shaun: [00:28:55] Rework is brought to you by Basecamp. Basecamp is the calm, organized way to manage projects and communicate with your team. You can learn more and sign up for free at