REWORK Mailbag 1 — Part 1

This is the first of two episodes where Jason Fried and David Heinemeier Hansson answer questions from our listeners. In this episode, they talk about the role of luck and timing in starting Basecamp; ass pricing (yes, you read that correctly); hiring in the early stages of a business; and more. If you’d like your questions answered on a future mailbag episode, leave us a message at 708-628-7850.

• The role of luck and good timing in Basecamp’s success - 00:51
• Doing something just because it’s fun or interesting - 6:42
• Why the customer support team pulled back on measuring response times - 8:45
• How Basecamp sets prices - 12:14
• Charging non-profits - 21:47
• Going from one employee to more than one - 24:53
• Managing hours and overlap in a global company - 26:49
• Bonus! Who is Meghan Markle? - 32:38

Transcript

(00:00:00) Broken By Design by Clip Art plays.

Wailin: (00:00:00) Welcome to REWORK, a podcast by Basecamp about the better way to work and run your business. I’m Wailin Wong.

Shaun: (00:00:07) And, I’m Shaun Hildner. This week we have Basecamp’s own Jason Fried and David Heinemeier Hansson answering your questions in our first mailbag episode.

Wailin: (00:00:15) We’ve been asking you to submit questions and Jason and David had so much to say in response to your questions that we decided to split this into two episodes, so you’ll get the second one next week.

Shaun: (00:00:27) These mailbag episodes have been really fun to put together, and we’d like to do a lot more. So, if you have any questions for Jason and David, or anyone else here at Basecamp, for that matter. Give us a call at (708) 628-7850. You can also email us at hello@rework.fm, but we’d rather hear your beautiful voices.

Lincoln: (00:00:51) Hi, this is Lincoln from Utah, in the United States. My question is: What was your initial strategy in starting out your company? And what role did luck play in that? Or, do you think that if you were to start over again today with nothing, if you applied the same strategy, if would work again?

Jason: (00:01:08) Well, I’ll start with that. Luck? Yes, of course. Most of that is timing, too. We were at the right place at the right time. We were early. And timing, I think, has a huge part to play in everything that works out and doesn’t work out. So, I think that if we started again, today, we would not be anywhere near as successful as we were when we started in 2004 with Basecamp. That’s basically my take on it. I think the fundamental principles are still important, because we’re still using those today. Build things small. Small teams. Work in quick iterations. That sort of thing. I think that all would still be true and should still be true. But, I think a lot of the success is tied into timing and luck and things you can’t control.

David: (00:01:46) Which, I think, though, applies mainly to the multiplier. Like, how big was the business going to be. So, the timing, and everything for Basecamp to hit just the right time, the right feature set, market fit, and so forth. Yes, absolutely. But, we also launched a bunch of other products that never ended up to be as big as Basecamp, but they could totally have sustained a perhaps slightly smaller business. That could have been run on the same principles and where we could have had the same, roughly, lifestyle of 40 hour weeks, embodying the same principles and values, and we could have just have done that, with, maybe we’d have 12 employees. Maybe we’d have 18. And that would have been, in many ways, just as fine, right?

(00:02:29) So, I think that often there’s a focus on oh, what is this magic angle I have to hit to make it. Well, make it is not a binary thing. We would have made it even if we could have stayed in business with eight employees. I had a great time running 37signals with you with seven people. Like, it was amazing! In many ways just as amazing, in some ways more amazing, and in a few ways less amazing. But still a great time and we could have done that with pretty much any of the products.

Jason: (00:02:56) For sure. I think though, also, besides timing is costs, which you don’t really hear a lot of people talk about. It’s like, a big part of this is costs. We could have actually been horribly unsuccessful had we grown to 300 people in three years. Then we would have died, basically. We would have been out of business or had to take a bunch of money, or whatever.

(00:03:19) If you keep your costs down, you can be pretty successful, pretty quickly, if your costs are low. If we had three or four people. A couple salaries, no big deal, right? So, I think that’s what kills a lot of companies is taking on huge amounts of costs early, primarily in salary and then being stuck. And then going, well, it just didn’t work out. Well, it would have worked out, had you been smaller.

(00:03:40) Now, certainly some companies you can’t be smaller. If you’re building a factory or whatever. But in software, you can be really, really small and get by. So, I think that’s another part that I haven’t really heard people talk about in the business for some reason, is watching costs.

David: (00:03:53) And I think it just plays into the sort of, what’s your ideal. What’s your role model here. If your role model is that you have to be the next Github or AirBnB, or Shopify, or even Basecamp, you’re setting yourself up for low odds. Those are the outliers. Even Basecamp at the level of success we’re at is a vast outlier. But there’s this huge ocean below that where it’s just as good on sort of a personal, life satisfaction level of running your own company, having employees you take well care of. Building a great product, and having customers that enjoy that. So, we have what, 150,000 customers or something like that. If we had 20,000 customers. If we had 10,000 customers. You could still build an amazing business on that. Literally an order of magnitude less successful than Basecamp and you’d still be totally fine and our life would be almost the same.

Jason: (00:04:49) Agreed. All that said, I do think we had a huge advantage in 2004 compared to if we started the business right now today. Given just that the environment and the ideas and the technology required. Like, today, for example, if we wanted to launch, would we even launch on the desktop, or would we launch on the phone first? If you launch on the phone first, you might not be able to actually create a business that’s viable. If you’re just doing a $1.99 or $0.99 or $5 thing on the phone. So, I think the fact that we started on the desktop, people are used to paying a lot of money for that kind of product, helped us, actually. In the early days especially, generate a lot of revenue. So, who knows.

(00:05:26) But, I do think that luck and timing are a huge part of anything.

David: (00:05:28) And it’s funny, too, because there’s—so, for 2003 and 2004 when we got started, all sorts of weird things were hard that are just not hard anymore. So, for us to get a credit card, what account, a merchant account. It was a huge thing that required us to train to our prices and banks were looking at us side-eyed. Now, you just sign up for Stripe and like five seconds later you’re taking payments. So, some things got really easy. Some things got really cheap. You’re basically… starting a software company today, you’re going to pay nothing for the infrastructure and running it. Like, we actually had to, sort of lease a part of a server, and then we had to buy real servers, and all this stuff was terrible. What’s harder today, I think, of course, is to sort of come up with something new that hasn’t already been explored and then build an audience, because it’s really loud.

(00:06:17) But, on the other hand, again. If you’re not looking at, oh, I have to build an audience of 150,000 customers. You can do very well, as I did a presentation at startup school, with 2,000 customers. That will make your million bucks a year pretty easy. Now, that’s still hard. Getting 2,000 businesses or people to pay you money is still hard. But a lot easier than trying to hit 150,000 customers.

Jason: (00:06:40) Agreed. Kelly from Wisconsin emailed us and says, “I like the idea of not always measuring something but doing it for the good of the company, or doing it because it’s fun and helpful? How do you feel about that?

(00:06:53) This is something we—this is important, actually. Really important. Because we measure certain things and other things we don’t measure at all. We’re very careful about measuring things like performance. And what I mean by that, not personal performance, like in terms of how much someone does at work, but how fast Basecamp is, how fast our servers are. That sort of thing. Also, measuring how quickly we get back to customers, customer service. Although, we’ve actually pulled back from—we measure it still, but we’ve sort of pulled back and I can talk about that in a minute.

(00:07:23) But there’s other things we do just because we want to do them, and I hope that most of the things we do is actually just because we want to do them. So, if it’s a new feature, if it’s a product change, if it’s just some new thing we want to launch, if it’s a podcast we want to do. It’s not because we’re measuring the podcast that closely, that, oh, this leads to 1700 new customers a month and if it only lead to 1500, we wouldn’t do it, or whatever. It’s not about that. It’s that we want to do it. Because if you’re not motivated to do it, if it’s not fun, if it’s not interesting. If it’s not a challenge, you can measure it to death, but you’re going to just hate it, basically.

(00:07:57) So, for the most part, we just kind of do what we want to do and make sure it makes sense at some level of course. WE’re not going to just do things that don’t matter. So, we kind of have a general sense. But also, for us, we—let’s take Basecamp for example. We use Basecamp here. We’re the number one customer of Basecamp. So a lot of the things we build in Basecamp have to make sense for us. And a lot of that is just like, how do we want to work all day. We’re in Basecamp all day. Does this make our work day better or worse? How can we make this place a calmer place? That sort of thing. So, measurement applies in certain areas and I think it’s very important to measure certain things. And other things, I think you can sort of kill it with measurement in a bad sense.

(00:08:37) For example, with customer service, we were measuring response times and we just assumed that, or, I don’t know if it was assumed. We basically proclaimed that quicker was better. So, you know, could we get back to people within five minutes, four minutes, two minutes, one minute. And we started measuring that and we still measure it, we have a rough estimate for how long it takes to get back to somebody, but sometimes when you measure it, people are driven to beat the numbers, and what we found was that it was causing a lot of stress. Is that people were trying to get back to people in two minutes or one minute, because it looked better if you’re measuring it. It looks, certainly better than three if you get back to someone in two. But it caused a lot of stress. We basically figured out, hey, five is amazing, too. And so is ten. Get back to people in ten minutes via email, that’s unheard of to begin with. So, let’s ease up a little bit. Let’s keep an eye on it so it doesn’t get to 45 minutes or an hour, or even 25 minutes, but let’s not keep trying to beat the numbers, and let’s find a range that makes sense. So that’s how we generally handle that.

David: (00:09:34) I think what comes with measurement often is metrics and goals, too. So, you’re usually measuring something because you want to measure up. You want to measure against this goal and this target that you have. And, as a whole, we have very, very few targets and goals at Basecamp. We have some rough goals and targets around performance as we talked about. But as the business as a whole, no. There’s not like a revenue target that we have to hit, or a profit goal that we have to achieve for us to be happy about the work that we’re doing. And I think oftentimes, you can absolutely kill the joy of something by creating these external motivators. These goals and targets that you have to hit, and you just suck out all intrinsic motivation of doing good work for the sake of good work.

(00:10:19) We’re not doing good work because we have to hit some number. We’re doing good work because it feels great to do good work. So, you really have to be careful what you choose to measure. There’s a standard management idea of like, you can only control that which you measure. Some bullshit like that. And absolutely not. Well, maybe actually control is the right word for that. And why would you want it so carefully control everything that you’er doing? Maybe you just want to do things because they feel good.

(00:10:51) When we think about Basecamp as a business, been around for 18 years. Jason and I have been working together for 16 years. At this point, we’re successful enough that Basecamp doesn’t need to do anything except sustain itself. Continue to interest and motivate Jason and I. Continue to be able to take care of the employees that we have and service the customers that we have. There’s no magic thing that’s going to happen if we grow the business 20%. There’s nothing that kicks in and then all of a sudden, like, ooh, wow, this is wonderful.

(00:11:20) No. Things are wonderful right now. So, we get to basically forget about those metrics because we’re our own stakeholders. And I think that’s oftentimes how people get sucked into metrics is that they’re not doing it for themselves so much. They’re doing it because someone else is controlling them, and that’s really what the whole setup is about. To have seomeone else who can have the controls in a business.

(00:11:41) Which is one of the reasons why we’ve never really had an interest to become a public company, because all of a sudden you have all these other stakeholders, who… I mean, they might think, in theory, it’s nice if Jason and David enjoys what they’re doing. But, you know what, I kind of care more that they meet their quarterly numbers and my stock price goes up. Which is completely natural. That’s just how it goes, right? So this is one of the reasons we’re so adamant about staying an independent company and staying with the stakeholders of just us. So, that’s a thought.

(00:12:12) Dennis from Denmark is asking, What is a good approach to setting the price structure? Should pilots be free for ever or for limited amount of time? Should I feel bad about charging non-profit organizations. My primary customer groups are volunteer organizations and non-profits, and I don’t want to appear greedy, I just want to help them.

(00:12:33) Maybe we’ll stop from the top. How do we set prices?

Jason: (00:12:34) How do we set prices? We have something we call Ass-pricing, which is basically pull a price out of your ass and go, eh, that sounds about right. That’s how we started. When we first started Basecamp, I believe it was $19, $39, and $59, and we were like, that just feels about right. I don’t know. Like, look, software, the margins are very high, or they should be. We had a few people, what, we had four people? Three people at the time? Four people at the time? And so, it didn’t, and we didn’t even know if we were going to be doing this for very long, but we knew we’d come up with some numbers, so we just kind of picked it, and guessed. Over the years, we’ve tried a bunch of different pricing models, and they’ve all just been like, well, what feels about right to try?

(00:13:18) Now, look, if you make widgets and whatnot and you have the cost of goods sold and you have to factor in supply and supply chain, and raw materials, like, you’ve got to make sure that your numbers make sense. You can’t charge something $5 that cost you $15 to make. But, in software, it doesn’t cost that much to make if you have a small team, especially, so you can kind of come up with numbers that feel about right. Then, we have done some testing as well. So, like, for example, we recently tested $999 a year versus $1000 a year. $999 won, so we did that instead. We’ve also tested things where the even numbers were better than the odd numbers. We played around with that stuff, but fundamentally, I wouldn’t worry too much about it.

(00:13:57) The thing I would be concerned about, though, is going too low. I think if you’re trying to decide between two prices, I’d rather go higher because you can always bring that number down. It’s a lot harder to raise prices on people later. So, if you are, uh, should we go $19, or $29, or $39, just go with the highest number you can come up with initially and then you can back off if you absolutely need to.

David: (00:14:19) The test we’ve used when we’re pulling the numbers out of our ass that I often refer back to, is would I pay for it? And we’ve used that a bunch of times. There’s just sort of a guttural reaction of like, would I actually pull my credit card out and put it in to pay for this product? And, I find that that test is a pretty good guide to whether this feels right or not. And what’s funny about it is that my reactions to prices are pretty much the same as they were in 2004. So, just because we’re more successful or we do better, I’m absolutely no more willing to pull out my credit card even to pay for our own hypothetical products. Because there’s just this feeling of like, what is the value here, actually? Is this a tool we’re going to use every day all the time? Yeah, I’d pay $99 for that. Is this something we’re going to use once a week? Eh, $99 feels a little rough for that. Maybe I’d pay $19 for that, and maybe I’d pay $30 for that. So, you can kind of hone in on it just through that level of instinct. Of what you would pay for it.

(00:15:14) Because the fact is that you’re unlikely to be that special. There’s probably plenty of people who are just like you or are within the margin of close enough and going to have to the same gut reaction on is this price right or is it not. Because you know what? Most people don’t sit down and do a cost-benefit analysis, and like, oh yeah, I will, $29? No way. I would have bought it for like $27.49. Right? It doesn’t come out to that precise. They just have a gut reaction to a price. Eh, too expensive.

Jason: (00:15:40) Your price might be specific, but in their head it’s a ballpark. Like, yeah, that’s about fair, or something like that. The other thing I have run into a bunch of entrepreneurs, because I get this question a lot, people email me about pricing all the time, and they’re struggling, figuring out their pricing. I don’t feel like we’ve ever struggled for more than five seconds just to even make up a number. I think, just make up a number. Of course, make sure that it makes sense, as far as your costs or whatnot, and I think that’s the most important thing. I think this is actually a big problem with apps, these days. Is like, Apple kind of encourages you to charge 99 cents or $1.99, or $4.99, or whatever, and so people just do that. But if you really do the math, you pretty much can barely make it work for one programmer to sell something for 99 cents.

(00:16:22) So, you’ve got to make sure the numbers work. But then, just pick something that’s reasonable. There’s really only a few slots anyway. Are you going to be less than $10, are you going to be, somewhere between 10 and 50? Are you going to be… more than 50, more than 100? And, yeah, there’s some price science and different companies do it different ways, but I just wouldn’t stress over it too much. The most important thing is that you’ve decided to charge for it. Come up with something that you feel is reasonable. I’d go a little bit higher than normal just for the hell of it. You don’t want to be on the wrong side of that, I think. You can always come down.

(00:16:51) And don’t stress about it so much. Just pick something and run.

David: (00:16:53) And the thing, too, is, you can change your mind.

Jason: (00:16:55) Right.

David: (00:16:55) So, you’ll pick the high price and maybe no people will show up to buy it, and you try to lower it. And if lowering it didn’t fix it, maybe just built the wrong product. And, then, you sort of just have that freedom because when you sell software in particular, everyone who shows up at your site is a new customer. So, we’re trying, at one point we were trying a bunch of different prices at the same time, because we get a lot of people who show up to Basecamp.com. They’re all new customers. They don’t know what we charge existing customers, and as long as it’s somewhat within a reasonable range, you shouldn’t be charging one customer $10 and another customer $1000. You get to play with those numbers. But the thing is, those levels of optimization? They don’t really matter. When you’re starting out in particular, whether you end up charging $29, or $39, or $59 doesn’t really matter. What matters is, are there any customers willing to buy my thing? So, sorting that out first is more important.

(00:17:47) Then the question is on whether the pilots or the trials should be free forever or for limited time. Here we’ve flip-flopped back and forth four times, I think. We started with a free trial on classic, then I think on classic, we tried no free trial. Then on BCX, we also launched again with a free trial. And I think when we’ve done the analysis on that, there’s definitely some benefit to free forever. There’s a long tail where we’ve looked at things like, oh wow, this customer had been on a free plan for four years and all of a sudden they decided to upgrade. I guess that’s kind of great.

(00:18:28) But it’s also—it doesn’t always feel right. It doesn’t always feel right to give your product away for free. Not at least in a way where it can just be used forever. Right, like, are you selling something here? Are you running a business or are you running a charity? And it’s totally fine to run a charity. I give software away for free all day, every day in the Open Source community. But then I also run a business and in the business, we charge for things.

(00:18:51) So, I think we, both Jason and I, have this sort of, mm maybe free sort of works but it doesn’t actually feel that right. And, what I’ve seen too, is that some really flub it on that. They just give the farm away. So their free plan is just way too good, and someone could reasonably use the entire product and never pay for it. That’s never been our model. Our model has always been, if you really like the product? It’s going to cost you. If you want to try it? Totally. Try it for free. We’ve tried 30 days, 45 days, 60 days. All sorts of different trial lengths and play around with that stuff, but at some point, if people like your software, they should pay for it.

Jason: (00:19:26) I think, also, there’s a little bit of—some people might say—well, you guys have been around for a while, so you don’t have to give anything away for free because people know your brand and they know your name, and they’re going to pay for it, but I’m brand new, so… I have to give something away for free. And I think there’s—I get that. We did that. I understand that. I think David nailed it, though, which is that a lot of free trials that I’ve seen are way too generous. It might be the number of users, for example. A lot of people? Well, five users for free. Five users is basically the entire business world. Millions and millions of companies have fewer than five people. That’s what you have to be careful about.

(00:20:03) We’ve always done either Basecamp either was free for 30 days, you could manage one product before you had to pay for more. Maybe with Highrise we did something where you got one or two users free or something like that. But if you’re doing the user thing, and you think five users isn’t a lot. It’s actually a huge number. Most small businesses—first of all, small businesses dominate the world. And most of them have just a few people anyway. So, be very careful about giving away too much. It’s also, again, extremely hard to pull back and someone’s who’s been using something for free all of a sudden, they get a notice saying, hey, we’re going to start charging for something one day? That’s very hard to do. So, I’d be careful about that.

(00:20:43) The other thing is whenever we change prices, we change them on—we don’t really change them, actually. We sell new customers at the new price. We don’t change prices on existing customers. I think we may have done that once or twice in our lives and I remember we did it with Backpack way back in the day. Backpack was like $5 a month and we went to $9 a month, or something like that.

David: (00:21:05) To seven.

Jason: (00:21:05) Or maybe it was to seven. And that $2 per month change was like, well, we were called a lot of things. We had to get a restraining order against one customer. It was a really weird time. Point is is that, changing a price on people is very difficult to do and I just don’t think it’s usually worth it. You’re better off just letting people have what they have, keep paying what they’re paying, and then make the new price only applicable to new customers. Over time, you have churn, so old customers go away, they’re replaced with new customers at the new pricing model, and I think you’re in pretty good shape there. That’s how I would approach it.

David: (00:21:38) Final question was, should I feel bad about charging non-profit organizations?

(00:21:44) First, no. So, just because someone is a non-profit doesn’t mean that there’s no money going in there. The people who work at a non-profit, they’re probably getting a salary. When they buy pens at Staples, they’re paying for those pens. Just because you have a product that doesn’t have a sort of marginal cost to it, doesn’t mean that you don’t have a real business that deserves to get paid. And non-profit businesses, they interact with the world of commerce all the time. It’s absolutely a natural way to go.

(00:22:12) Now, that doesn’t mean you can’t sort of have some concessions on that. We’ve tried different things. We started out with a pretty hard line that said, nope! You’re going to pay exactly the same because we came from the direction of like, there are plenty of non-profits that are very, very fat and lush organizations with very cushy, well-paid jobs and big expense rolls and so on, why should they get our product for less money than a small business that’s just starting out and struggling? So, there’s some of that.

(00:22:41) And then, we kind of softened our take on it and we’ve experimented with different levels of discounts, and right now we’re giving, I think, a 10% discount to non-profit organizations. A lot of that is just built into the patterns of how organizations buy. A lot of non-profit organizations are used to getting a discount. So, they’re used to asking, hey, can I get a discount because I’m a non-profit. And a lot of businesses just give that to them. So, we kind of just removed that as a barrier to buy Basecamp, that yes! You’ll get a discount. It’s 10%.

(00:23:13) So, I wouldn’t feel bad about it at all. I wouldn’t feel bad about charging them. It’s fine to give some sort of discount if you feel like it. Also fine to not give a discount. We had plenty of non-profits that bought Basecamp when we had a discount and plenty of non-profits who bought it when we didn’t have a discount, and you’ll be fine either way. I don’t think there’s anything about being greedy about having a sustainable business. I think that’s just a bad dichotomy to be caught up in.

(00:23:41) People who work at a non-profit and take a salary, are they greedy? Should they all work for free? Should everyone give all non-profits in the world something for free. And also, just because someone is a non-profit doesn’t mean you necessarily believe in what they’re doing, or they’re efficient, or they’re doing well or whatever. It’s a tax status in a lot of ways. Sometimes it means that they’re doing great, charitable work. And sometimes it means that they’re fat, sloppy organizations that just waste everything on galas and I don’t know, dinners and bullshit, and they shouldn’t get a dollar off anyone or any donations.

(00:24:16) So, there’s not just that designation alone. It’s too broad to make these sort of mass classifications on. You could still choose to make one-off exemptions. We’ve done that in the past. Where we’ve just said, this organization in this particular case, we’re going to give you Basecamp for free. For example, we’re giving Basecamp for free to all teachers and students who want to use it for education. And we’ve decided like, hey, that’s one area we want to do something special for. You can’t do something special for every new one or you’ll end up with no business at all. But pick a few things and feel good about that, and then don’t feel bad about charging non-profits.

Nate: (00:24:55) Hi, my name is Nate. What do you think about when you’re going from one to two people, I guess. Employees, and it could be bringing on a partner or something like that. But what do you think about the decision and the process you should be thinking through when you go from one person to being a company. Being more than one person?

Jason: (00:25:15) Well, hopefully you’re going to two because you need the second. I think that’s maybe the first thing. Regardless of if it’s from one to two or two to three or three to four, or whatever. You’ve got to need that other person because there’s a gap. There’s something you can’t do. And maybe you’ve tried to do it, and that’s what I’d recommend, is making sure you’ve tried to do it first, if you can. If you can’t do it, then you bring someone else on.

(00:25:35) It should feel like I’m doing this because I have no choice. That’s at least the way I look at it early on, especially when you’er trying to control your costs and keep costs down, because people are going to be the most expensive thing you’er going to run into, especially if you’re building a software business. So, I feel like, you’ve got to need that person. If that person wasn’t there, there’d be something you materially could not do that would hold you back in a way that could really hurt the business.

(00:26:00) If you’re not feeling like that, you might want to wait. That’s what I would think about ahead of time. The other thing, I think that’s really important is figuring out, creating some clear roles even though, two people’s pretty small, obviously. But you’ve got to make sure everyone knows what they’re doing and if there’s a whole lot of overlap… you’re going to want some overlap. Definitely some overlap and you want to share some principles. And some ideals and some values. So, there should be maybe a little bit of overlap so you guys see some things in common, but you shouldn’t be mostly doing the same thing. If you’re a designer, bringing on a second designer, that probably doesn’t make sense. David, for example, is a programmer. I’m a designer. We can do a lot of work together that we couldn’t do apart. I think that’s important. But if your second hire is just like you, I think that’s probably the wrong hire.

(00:26:45) Uh, we had a question from Twitter from Philip Berger who wanted to know about managing hours in a global company. What do you do when the only overlap time for a meeting is outside of core hours?

David: (00:26:55) That’s a good point, because we have employees in Europe and I started working with Jason from Copenhagen, Denmark. This was seven timezones away from Chicago. And there’s definitely some consessions you have to make. So, when I work in Spain where I’ve been living about half the time for the past five years, I had to move my hours. I couldn’t work 9 to 5 and then have a reasonable amount of overlap with the rest of the company. So, I moved my hours to 11 to 7, and I actually ended up really enjoying those hours. They actually fit the Spanish lifestyle really well. You eat later dinner, and you get later in the morning, and I just… I found, actually, I enjoyed that better.

(00:27:36) Now, that doesn’t work for everyone, but you’ve got to recognize that if you want to have a global company and if you want to have people working remotely, there’s some great pros about that. There’s some awesome things, like, I got to live in Spain in a small town that had nothing to do with tech. Like, that would have been impossible before remote work.

(00:27:55) And then, there’s some cons. Potential cons. Some concessions you have to make to get to enjoy such a wonderful benefit. And for me, that was moving my hours, because I don’t think you can just expect that everyone is just going to work 9 to 5, and you’re going to work across 10 time zones. If you don’t have overlap, you’re going to have a shitty collaboration. I think a lot of the pushback to outsourcing from the tech industry that came in the last ‘90s, early 2000s were because people were sending work to India, or whatever, and it wasn’t about who was in India. It was about the fact that there was no overlap with the people working in India, so everything happened on like a day delay. You had to send an email and then you’d get something back, and it would take days to get the simplest thing done that two people just talking in real time could have figured out right away.

(00:28:41) So, you have to just take those concessions and take them seriously and ensure that you have a reasonable amount of overlap. We try to aim for three to four hours. That’s great. I say, at least three hours of overlap. If you’re getting less than three hours of overlap, someone’s going to have to move their time around somewhat. Now, it doesn’t mean that everyone in the company necessarily has to do that. We have people on the west coast, that’s nine hours off from Spain, and when I’m in Spain or I’m on the west coast, sometimes I don’t even have a couple hours of overlap with those people. But, as a whole, the company should feel like well, at any one time, in a given day, if I plan my time a little bit, I can talk to that person directly, with sort of a real-time setup, and we can figure some things out.

(00:29:25) Some things actually are great and actually improve when you don’t have real-time communication. I love the fact that when I work from Spain and I start working at 11, it’s completely quiet. There’s no pings. There’s no chats going. There’s no nothing. And I can read something that someone wrote yesterday and prepare a response to that asynchronously, and that’ll be wonderful.

(00:29:47) And then there are those things you just need to hash out in person, and I think you really get the best of both worlds when you actually have that. My preferred work style is not eight hours of overlap with everyone I work with. My preferred work style is like, about half of that. If I get four hours exclusively to myself, and four hours of intense collaboration? Perfect.

Jason: (00:30:06) Yeah, the only thing I would add is, I know when David was in Spain, we basically know that whatever time we want to talk, we have to do it by 11am central. Which is, I’m in central time. And so, it’s kind of nice, because first of all, it cuts back the number of times you talk to one another in a given day, which is nice in a sense. It also helps you make sure that you leave mornings open if you need to talk. And, it just, it seems to work. I think what we haven’t done, and I don’t think it’d be very successful, is if we had, for example, a product team that was mostly in, let’s call it, central time, and then also in Japan. I don’t know what their time zone is, but I think it’s probably 12 hours difference or something like that?

(00:30:46) We haven’t done that. We have people in Europe. So we’re talking six, seven time zones apart. I think what, Chicago is -6 GMT, or something like that. So, you can kind of pull that off, that’s actually really nice. I think we’ve been sort of intentional in the fact that we don’t have product teams spread out 12 hours apart. You could, if you had people in Europe working with people in Australia or something like that, or Japan, you could pull that off. But we don’t really have that setup. So, I’d be careful about that.

(00:31:14) Also, in general, like, your questions about meetings, we generally don’t have them. So, another thing that’s important, I think, is to think about how to work without those. So, you know, most of the time David and I overlap. When he’s in Spain it’s a one on one thing. We’re like, hey, let’s have a call and talk about something. It’s not let’s pull six people in the room and talk about something. Because then you have to coordinate even more people.

(00:31:37) So, for the most part, most things can be written up instead of have to have a meeting about it. So, you write it up, post it to Basecamp—in our case, we use Basecamp, of course. Post it as a long-form message and someone gets back to you the next morning, or whenever they have a chance, or a few hours later. And you can avoid a lot of the meetings. So, you can actually avoid a lot of the things that you think you need to do. So, that’s another step in the right direction, but I do think, like David said, a few hours of overlap is very important.

(00:31:57) Broken By Design by Clip Art plays.

Shaun: (00:32:38) Who’s Meghan Markle?

Wailin: (00:32:40) Are you serious?

Shaun: (00:32:40) I am dead serious. Oh, I know she’s married to a prince—or going to marry a prince. Sorry. Strike one, Hildner.

Wailin: (00:32:49) They’re not getting married until May of 2018.

Shaun: (00:32:53) Who is this person?

Wailin: (00:32:54) Okay. Meghan Markle is an American actress. She’s biracial.

Shaun: (00:33:01) Known for…

Wailin: (00:33:01) The show Suits on cable.

Shaun: (00:33:04) Missed it.

Wailin: (00:33:05) You know, it was on—she was on it for six or seven seasons which is very long for a TV show. I mean, like…

Shaun: (00:33:13) I don’t even know what this TV show is about.

Wailin: (00:33:16) Oh, it’s a legal drama. She plays a paralegal named Rachel Zane. And, you know, Bunk, from The Wire?

Shaun: (00:33:22) Yeah.

Wailin: (00:33:22) He plays her dad on the show, Wendell Pierce.

Shaun: (00:33:23) Okay.

Wailin: (00:33:24) You think about all the network shows that don’t make it to 100 episodes, right, and Suits is still on. I mean, she left but the show is still on.

Shaun: (00:33:32) Why’d she leave.

Wailin: (00:33:34) Because she’s gonna be—

Shaun: (00:33:34) Because she doesn’t have to work anymore?

Wailin: (00:33:35) She’s gonna become the Duchess of Sussex, probably.

Shaun: (00:33:39) Would I know her from anything else?

Wailin: (00:33:41) Well, she is in this Hallmark movie that I definitely put on hold at my local library. I’m waiting for it to come in. It’s a 4th of July-themed romance called When Sparks Fly. Here is the plot.

Shaun: (00:33:55) Before you continue, did you only put this on hold because Markle’s in it?

Wailin: (00:33:59) Yeah.

Shaun: (00:34:01) Okay.

Wailin: (00:34:01) I was like, I cannot think of a better thing to do over the holidays than to convene my girlfriends with some wine and some snacks, and watch—

Shaun: (00:34:08) And watch a movie about a different holiday?

Wailin: (00:34:10) And watch this Meghan Markle movie. But, in it she plays a Chicago newspaper reporter, basically me, in my old job, I guess. And she pitches a story about the fireworks industry. Maybe she’s a business reporter. And it turns out that her family in Wisconsin owns a fireworks company, so her editor is like, go up to Wisconsin and do a story about your family business. Your family’s business, like…

Shaun: (00:34:42) Fireworks stand, or manufacturer?

Wailin: (00:34:43) Like, a manufacturer, I think.

Shaun: (00:34:45) I thought they had to all be made in China, right?

Wailin: (00:34:47) I have not watched the movie yet, so these are details that might be covered when I view the film. But, she goes up to Wisconsin—

Shaun: (00:34:54) Listeners, we’ll be back next year with a full review of When Sparks Fly.

Wailin: (00:34:58) Oh, it’s a very special episode. You know we graduated the same year at Northwestern, but we never met.

Shaun: (00:35:07) And she played you in a—

Wailin: (00:35:08) She played me—

Shaun: (00:35:09) TV movie. You’re basically half a degree of separation from the royal family.

Wailin: (00:35:15) I’m like, basically in the royal family.