A Leanpub Frontmatter Podcast Interview with Matthew Guay, Senior Editor and Writer at Zapier

The team from Zapier has published a number of books on Leanpub including The Ultimate Guide to Remote Work: How to Grow, Manage and Work with Remote Teams. In this interview, Leanpub co-founder Len Epp talks with Matthew Guay, senior editor and writer at Zapier, about his background, remote work and some interesting approaches to it that have been adopted at Zapier, the books Deep Work and Messy, and at the end they talk a bit about Matthew’s approach to producing Zapier’s books.

This interview was recorded on May 31, 2017.

The full audio for the interview is here. You can subscribe to the Frontmatter podcast in iTunes or add the podcast URL directly.

This interview has been edited for conciseness and clarity.


A Note About the Leanpub Frontmatter Podcast

This summer we split the old Leanpub podcast into two distinct podcasts:

Frontmatter, which is a general interest podcast where you can listen to Leanpub authors talk with Leanpub co-founder Len Epp about their books and their areas of expertise, from data science to molecular biology, to the history of labor and management. And for those interested in the nitty-gritty of what it takes to be a successful self-published author, at the end of each episode Len asks the author about how they made their book and how they are spreading the word, and other publishing shop talk.

Backmatter, a new podcast focused specifically on the publishing industry and its latest trends. In each episode Len interviews a professional from the publishing world about their background and their insider’s perspective on what’s happening in the huge and evolving world of book publishing.


An Interview with Matthew Guay

Len: Hi I’m Len Epp from Leanpub, and in this podcast, I’ll be interviewing Matthew Guay.

Based in Bangkok, Matthew is a writer and senior editor on the marketing team for Zapier, the popular service for integrating apps and automating workflows. You can read Matthew’s blog at techinch.com, and you can follow him on Twitter @maguay.

Matthew has helped write a number of books for the Zapier team, including The Ultimate Guide to Remote Work, [The Ultimate Guide to G Suite](The Ultimate Guide to G Suite), and a few others.

In this interview, we’re going to be talking about Matthew’s professional interests, his career, and at the end we’ll talk a little bit about self-publishing content.

So, thank you Matthew for being on the Leanpub Podcast.

Matthew: Absolutely, thanks for inviting me.

Len: I usually like to start these interviews by asking people for their origin story, and in preparing for the interview, I saw that you studied computer information systems at college. You eventually became a writer, and worked in marketing. I was wondering if you could talk a little bit about that journey, and perhaps how you ended up in Thailand?

Matthew: So it’s funny — college to me feels like this huge decision. Kids get out of high school, they’ve had most of their courses planned all the way through. And then boom, you’re 18 and you’re supposed to decide what you’re going to study for your career for the rest of your life. And as we know, especially nowadays, that really often doesn’t stick. The best thing college is going to prepare you for — hopefully — is a life of learning, where you keep learning throughout life through reading and studying and whatever.

I grew up in Thailand actually; about half of my childhood was in Thailand. My parents are missionaries [up-country?] in Thailand. And so when I went to start university, the town we lived in was very small, had one community college and not many other options. So I looked around a bit at online college options — to maybe do one year there, and then move back to the States or a larger city in Thailand and finish college.

I started out at University of Texas. I was planning on doing engineering and calculus. [That] absolutely was terrible, and so I decided to switch to IT and computer information systems instead. But basically that first year, I was studying from the University of Texas online. I had a Professor in business writing, [unintelligible name], and she had us, as a project in the class, make a blog.

It was just supposed to be like, make a small portfolio online. Well, I actually decided I would write tutorials on there and just sort of keep the thing going, and learn from that, that you write really niche tech articles.

For instance, I wrote a tutorial about how to fix this specific printer and get it to work with Windows 64-bit. I forget what version. And it got steady traffic, because it was the first result for that very, very niche keyboard result. That basically started me on the route of writing about tech.

I ended up transferring to Florida Tech, finished my degree online from the middle of nowhere in Thailand, and started writing online at the same time. It just sort of went hand in hand — it was a job I could do as an easy way to get started in tech. The IT courses gave me enough tech background to be able to inform the writing. So, hopefully I can write about tech in a way that simplifies it for people — makes it not so technical, and yet I can stillgrasp the technical aspects and help people through that. So it’s a thing where I accidentally fell into both the degree plan and a career that was slightly tangential to that degree. And it went from there.

Len: There’s a coincidence in your background, and where I happen to be living right now, which is you used to work for MetaLab, and in a job related to their product called, Flow. I live in Victoria — MetaLab is walking distance. Their office is, as I understand it, pretty close to where I am. I just wanted to ask you, what did you do for the product?

Matthew: Oh very cool. I had worked for CoSupport, which was a start-up by Sarah Hatter, who used to be at 37Signals. Basically it was writing documentation, and starting support for new companies. And MetaLab got in touch with us, wanting us to help push their support forward for Flow at that time. That’s how I ended up working with them as a contractor, through CoSupport. And then I ended up working with them directly, essentially just doing their customer support and documentation, which was a super cool way to really dig into a piece of software and learn every little tiny thing, every tiny problem people are going to have. Whatever. You learn all the edge cases, and you can document them and support them. That’s what I did with Flow.

Len: One of the really interesting things about running a service online or a digital product is that if the writing is really good, then the scale at which you can operate increases dramatically. I think it’s something a lot of people don’t necessarily recognise. How, if you get the words just right in something, like a customer support document, or even in automated emails and things like that, it can make a huge difference.

I was wondering if you have any advice for anybody out there who might be running a little start-up, for what they can do for — perhaps good examples of customer support documentation that they can go to?

Matthew: Two things I’ve found with that is — one — especially if your product’s very focused, if you do support enough, you answer people’s questions, you end up finding the normal problems people have, the features they want, the bugs they hit, etc. As a developer you can fix those. You can start solving some of those problems. But some of the things are going to be — maybe you can’t fix them, maybe it’s just the way your product works. It’s a mismatch. And you can use that to inform either your product or documentation or both.

Say you answer a question one time, and the person doesn’t exactly get what you’re meaning; switch the answer up a bit. Next time, try that new answer on the new person. If they get it the first time, you’ve probably found a winner. Now you can save that as a text expander, make it into a support doc — whatever. And you can almost, maybe not exactly automate that one support case, but you can almost automate it. You can now reply very quickly, and hopefully have enough time to make it personal.

So if they say — maybe they have this one problem and some more personal need, you can reply to the personal need to make it a human interaction. The actual steps of what to fix — you’ve already written that, just reuse it. And so you can use it sort of like — usually we’d A/B test your answers. Send it to a customer. If it doesn’t work, try another answer. Hone that until you get something great.

And then at the same time, you’re building a public-facing support library, with those great answers that you’ve tested on people. You put those online, and hopefully your customers start solving their own problems.

The funny thing is though, that makes support more difficult. Because once you’ve solved the easy problems, the things people do send in, are going to be very difficult, and you’re going to have much harder tickets. But that’s actually a good problem. So that’s something — that flow — definitely that was the case with a more focused type product. Finding the edge case is easier.

At Zapier, our entire company does all team support. Everyone from developers to our CEO, marketing — everyone’s chipped in to support, some per week, as a way to understand our customers: the problems they hit, the things we can do to help them. And Zapier connects 700 apps together. So your number of edge cases are just phenomenal. It actually doesn’t work quite as well at Zapier in that sense, because we’ve got so many edge cases, you’re not going to memorise them all.

Which is where documentation comes in. If your product’s really massive, even your own team’s never going to remember every possible thing that could go wrong. So you document those, it helps your team, it helps the public. And it should grow your support together.

Len: And what sort of documentation system are you using?

We have an internal tool. All of our content at Zapier is built on Django. It’s a custom CMS we have, it helps us tie it into the product.

Len: We started using something called Intercom a while ago which a lot of people who are into start-ups and stuff will have heard about. Rhey started this new product called “Educate” which has been really useful for us in dealing with things — where basically you can easily create an article online, and then, if a request comes in over email, you can just put a link to the document. And then, you can actually see where people go from that document elsewhere, which is really useful.

It’s interesting you brought up 37Signals. I believe it was in one of their books that they focused — or at least, devoted some space to the importance and power of good writing on having a great product. It’s just so, so important. At Leanpub we’ve experienced decreases in customer contact around certain issues by changing two words in an email.

Matthew: I can imagine.

Len: It’s just incredible. But I can only imagine the challenges of doing it with so many integrations.

Actually, on that note, could you maybe explain a little bit about what Zapier is, for those who are listening who might not be aware of it?

Matthew: Sure thing. Zapier’s an automation platform that helps you basically get rid of your busy work. You need to copy and paste stuff, perhaps? Instead of doing that, Zapier can watch your apps for new data and copy them over.

That sounds geeky, so let’s make it a bit simpler. Say you have a sign up form for — you’re going to launch a book, right? And you have a blog, you put a form there, and you want to send those people an email to thank them for joining your email list. And then you want to add them to your email list.

So, we’ve got three steps there. With Zapier, you’re going to make a form with whatever format you like. We support — I’m going to say, 15, off the top of my head, I’m not even sure, there’s quite a number of formats from Typeform to Google Forms, Wufoo, etc. You can add your form to Zapier. So it’ll watch for new entries. Whenever anyone fills out your form, Zapier will get that data. So, now you can connect Zapier to Gmail, and tell it, “I want to send an email to this customer.”

And you write it from your personal Gmail account, so it feels like a more natural reach-out. Maybe you can fill in their name from the form, etc., and Zapier will send that. And then it will add them to your email list, say — and we’ll copy that email address over to MailChimp. You could even add a delay in there, and three days later email them again with a copy of your first chapter as a download.

That’s a tiny example. You can do those same kind of things with Salesforce, with Google Sheets, with just tons of different software.

Some of the things we see are very small use cases. Maybe you just need to share your RSS feed to Twitter and Instagram. Well, Instagram would be a very bad idea then. Let’s say Facebook. You can very easily do that with Zapier.

Or say you want to build an entire business. There is a customer of ours who uses Zapier to run basically an Uber for lawn mowing, where they have a form on their site where you can book a lawn mowing session. It sends an SMS to the lawn care professional who’s closest to your house, and arranges the whole job, does the payments and everything. It’s all routed through zaps, and so you can use it as a simple way to build basic software without coding. Or you can just use it to simplify tiny things that bug you in your professional work.

Len: That’s really cool, I hadn’t thought of Zapierin quite those terms, but that’s really interesting.

One thing about Zapier is that it’s very clear in its messaging about its mission, which is that there’s work that should be done by people, and then there’s work that should be done by computers, essentially.

With the obvious caveat that any opinions you express are your own, I wanted to ask you a little bit about the marketing that goes in around automation.

It’s a big topic these days, and something that people are often quite concerned about when they hear about automation: that people will be losing their jobs, essentially. This is not a new worry, but it’s reached a new pitch in society. I was wondering if, as someone who writes about tech generally, you could talk a little bit about that. What’s your opinion about the impact that — not so much necessarily in digital activity, but what is the impact of automation going to be on the economy and on society, do you think, going forward?

Matthew: Yes, with the caveat, I’m definitely not an expert here. It is funny, because automation is sort of the technologist existential crisis. If you read Hacker News, there’s probably at least one post or one detailed thread every day with basically people thinking within five years, no one’s going to have a job, etc. Society’s going to break down, it’s going to be crazy.

And it does worry me in some respects, automation. We need to be able to retrain people. People need to be able to switch jobs more easily.

But actually, working at Zapier, I think there’s going to be a different perspective on it. We had a customer the other day tell us they don’t really save time with Zapier. Because of the volume Zapier operates, the work wouldn’t get done in the first place if they didn’t have it.

Think about how many jobs today are done by automation that wouldn’t be done otherwise. Spam email is a very easy example — unfortunately on both sides of the spectrum. And if you had to actually send each spam email individually, it wouldn’t be such a challenge for us to combat. So that’s a bad side of automation — it’s being used for a bad purpose.

But on the same side, if you didn’t have automation, there’s no way email could filter out all of our spam emails. That wouldn’t even be a thing, you would need every human on earth to sit through and read emails and find those and get rid of them.

And so to a certain degree, I tend to believe that there will always be more jobs. There will always be things where people need to do more stuff. Automation’s not going to come and take away everyone’s jobs entirely. It’s going to take away some part of your job, and you’re going to have some time to focus on what’s the core aspect of your work.

For instance, in our work at Zapier, obviously we’re building an automation tool. We tend to use it a lot ourselves. And yet, our team is still growing. Every Friday, you still get to the end of the day and you’re like, “Oh man, there’s more things I could do.” And I think that’s a great thing, that you’re able to think outside the box, instead of sitting there and feeling like you have to copy and paste data between stuff. Zapier can do that for you. Instead of you needing to filter your spam, or whatever, there’s all these jobs that we can let automation do, and it basically gives humans more place to specialise.

With self-driving cars even, you can look forward and imagine a future where people are needed in some aspect. Maybe they actually still take the packages to the customer? Maybe they’re sorting things in the back of the truck while the truck is driving? It’s really hard to say. But I tend to believe that there will always be extra things that we can do. And in your own personal career, and for today. That’s not here.

So how do people prepare for automation? Part of it is just thinking about what in your job is repetitive and tedious — those things are often things you can automate. And you can go ahead and do that. Make yourself more efficient at your job. And that gives you a chance to grow your skills, and basically future-proof yourself.

Len: That’s a really good answer, and a hopeful one, which is great. I think it’s in alignment with what a lot of people are saying.

One interesting thing that technology has enabled, in addition to all kinds of automation is remote work. I was interested to learn that Zapier is not just a 100% distributed team, but has been since its founding in 2011. You guys literally wrote a book about it. I wanted to ask you a little bit about that, for those who maybe haven’t had the pleasure of working on a distributed team. What are some of the benefits you most enjoy, and what are some of the challenges that you find most difficult about that style of work?

Matthew: Zapier started out as a remote team. If I’ve got the details correct, when Zapier first was founded and got accepted into Y Combinator, the founders were going to move to Silicon Valley for the connections, to be close to investors, etc. And one of the co-founders did not feel he could move right then. That started the idea — when he had to work for remotely, that he could work remotely from where he was. And then he later joined them. It essentially started out that way. Zapier just grew, and our entire team is still remote. There are people who live nearby who get together for monthly or weekly co-work sessions. But for the most part, we’re all working in our own offices or local coffee shops, or co-working spots and building the product together.

The thing that you really need to make that work, is communication. Obviously, communication is important for any job. Anything you’re doing together with other people, you need to talk about it. But in a remote team, the person you need to talk about that with may be 12 time zones away. Or they may be in your time zone, but their dad’s sick today, and they can’t be in the office. That’s why written communication is really important.

I think one thing that’s probably helped inform the way we write in public is the way Zapier writes in private. Everything we do is discussed in text. We write internal documentation about often just our thought process about why we’re doing a certain thing, what we’re trying. “Oh this experiment worked,” or, “It didn’t work.” And now future employees can go through and read that, and instead of making the same mistake again, they can improve on what we did in the past.

Obviously, all day we’re in a team chat app. We use Slack. We rarely use email. Email’s more for third-party interactions. For talking to partners and people who aren’t in our company team chat, then we have the internal — what you used to call the intranet, basically. Nowadays, we use [? 20:18]. And we have an internal blog, where we post more or less longer-form announcements. All those things help us work together remotely.

So even when we are together — two to three times a year, the Zapier team gets together for all-company retreats or full-team retreats. Even when we’re all in the same room, we’re mostly sitting at our computers, saying the very same stuff on Slack that we would otherwise. And often, even if we get together and we’re talking about what we’re going to do, once we’re done with that talk, we’re going to sit down and write it up. Just so it doesn’t get lost. That’s a core value we have, and it’s made remote work for us.

Sometimes you can find trade-offs that make it better. I’m in Thailand, and the rest of the editorial team is in the States. Actually right now it’s in Eastern Standard Time, and so we’re basically 13 hours off. They can be working on a piece of content during the day, and then they message me at 6pm their time, 7am my time, and they’re like, “Hey, can you edit this today?” When they wake up, I’ve got it edited in their inbox ready to go. Or vice versa. I can write something, they can edit it during the day.

To a certain degree, being remote lets you do these crazy hand-off things, where you can keep the company running 24/7. There’s always someone in the office, even though we can easily let people go do what they need. Being remote, if you need to take time off, you need to go check on something, be home for the UPS guy to bring a package? You sure could. That works well.

Of course the downside is exactly that too. One — you’re at your own house, so it can get lonely. And two — obviously — communication can be a challenge still. If you need something from someone in a different time zone, you really may have to wait till tomorrow. But I think that helps us focus also, because you have to plan ahead, and you have to realise that sometimes you need to just fix your own problem and not wait for whoever to come fix it for you. So it’s definitely got its pros and cons. But I think the pros vastly outweigh the cons.

Len: Did you say two or three get-togethers a year?

Matthew: Yes.

Len: That seems to be one of the big challenges that people have, is keeping cohesiveness over time. And regular whole company get togethers — if you can afford them, sounds like a really good solution to that. But it’s interesting you talk about how even when you’re together, you end up working the same way.

Matthew: Yes. We have one other thing that I think helps with that. Every week we have a random pair partner. We have script that randomly assigns two people on the team to have a chat. And we’ll just jump on the phone, and literally chat about anything. It may seem silly, but the good thing is, it helps us meet new team members, and it gives you the whole water cooler banter, where we can’t exactly go out to lunch with a co-worker so easy. But we’ve got that, and it gives you a bit of a personal connection.

And then different teams will do similar kinds of things. The group of employees that are in Asia Pacific, in general, will have a once a month meetup. And at first we’re like, “Oh we need to do business related stuff.” And it’s really devolved into just discussing life. Just having a hang out. And it’s a great time. Sometimes we’ll discuss work stuff, and sometimes we’re discussing, literally, the weather. I think that’s a great way to make us still feel like we’ve got that personal connection, even though we’re all remote.

Len: Those sound like two great ideas: the meet up, but also that random assignment of you to someone else to have a chat. I’ve never heard that before. but that sounds like a really great innovation for keeping a remote team cohesive, as you say, with less regimented styles of work, knowing more about your colleagues’ needs and interests — sick dad, things like that, can really help you manage things better.

One of the things that people talk about being an issue — this is true for office work as well, but in particular, when you work from home, you’re entirely in control of your own environment. You’re often very much in control of your time. And it can be difficult for people to focus. So one thing that people who work remotely do, is they have discussions around their set up, and around their practices.

I just bring this up to build up some context for a really good blog post that you wrote recently about two books, one caled Deep Work and one called Messy. I was wondering if you could share your thoughts about those books? About “deep work” and about the positive things that can come from that, but also the positive things that can come from something which is opposite, like it’s described in the book Messy.

Matthew: I had read the Deep Work book and found it really fascinating. Our marketing manager, Danny Schreiber, had mentioned that he had been reading a book called Messy and found it equally interesting. In comparing notes, it seemed like these books were sort of opposites. Deep Work had been basically at the top of charts of business books for 2016 for a while. Messy was similar but not quite as high up. I thought that was a great chance to read and contrast them.

And when I read it, the funny thing is — I found so many similarities. Because the basic thing is still the same: we need to do creative work nowadays. Maybe 100 years ago, it would’ve been fine to chop wood the very same way forever. Today, most people are not going to think that’s fine. Even if you’re chopping wood, you need to find better ways of doing it.

That takes two things. It takes focus and it takes creativity. Essentially that’s the message of these two books. The first is focus, the Deep Work book — it’s probably especially important for remote workers. He mentions how noisy our office can be, how as a professor, he always has people asking questions, stomping in his office, and that keeps him from getting things done.

But whether you have that or it’s just your email inbox, we’ve always got people making demands on your time. And Deep Work essentially says, “You need your high quality works that you’re going to produce — it is the time span, times the intensity of focus.” And it’s so easy nowadays to be distracted. Computers, which are the tool we use for work, are also the same tool we use for entertainment. We’ve got social media, you have Netflix. Everything’s right there to distract you, and everything’s there to keep you productive. You can do research about some topic, and it can be very productive. But sometimes you’ve got to know when enough’s enough, and say, “Hey, I’ve got to actually do the work,.”

He gives four steps for that, to work deeply. By that, he means to set aside time where you say, “Look, I am only doing this project. Everything else is off.” Maybe even go offline. Maybe even, as a remote team member in Slack, post your status as that you’re busy on this project. Maybe if you’re in an office, literally put a flag on your desk or something, to say, “Hey, please don’t disturb me.”

And then he says to embrace boredom, and quit social media. Both of those sort of go together. Instead of checking your phone or opening the Twitter app all the time — be bored sometimes, that’s a great thing. And then drain the showers, which is, get rid of the least important work. That’s probably where automation can come in — if you’re copying and pasting data, there’s probably a better way to do that. So that’s Deep Work.

Messy wants the same results. But it says that basically sometimes, if you regiment your life too much, everything’s in the same order. Nothing will ever spark your creativity. The author mentions that for commuters in London, the Tube train system was down for a day. And so the commuters had to find a new route to go to work. And by tracking the data on the Oyster cards — which, in London you use to pay for buses and the train — they found that a lot of people found a more optimal route to get to work everyday, just because the train was shut down. So if the train hadn’t shut down, you would’ve kept doing the same thing forever, wasting 15 minutes a day. But since the train was shut down one day, that messiness forced you to find a better solution. You had to essentially try the bus, and you realised, “Oh wow, this is better.” And you switched your normal commute.

Things like that actually happen. That’s why jazz is a thing, improv. Basically he’s saying, “Maybe you need distraction? You need a bit of a mess.” And that distraction’s probably — once again — not going to be Twitter and social media. But maybe, if you’re working remotely, you need to get out of your home office. That might be too much after a while. Maybe you need to just work at a co-working spot, or get some outside feedback? Maybe you need to talk to other people?

I think it’s a good reminder that basically, Deep Work can make you feel like you need a laboratory, you need to be sterile, you need focus. And that’s great. But Messy says, “Hey, if your desk is a mess, that’s probably not the worst thing in the world.” If some problem comes up, some emergency and you have to throw your whole work day out of whack — now it gives you a deadline where you have to work harder, and you’re going to be more creative to hit that deadline. I think it’s a good thing to say, “Don’t stress so much, right?” Life’s messy, deal with it. It’s a good thing. It can maybe help you do better, more creative work. So I found them both fun.

Len: It’s just a very clever way of putting together the ideas of focus and creativity and how they can play off each other. I really like that bus example, or the London Metro or Tube example as well.

It reminded me of when I was an undergraduate. For my first year, I took the bus to university like a chump. And then, in my second year, there was a bus strike. So, I had to walk. And while all sorts of interesting things started happening, like people would see students walking and just pick them up and give them rides, I realised that it would take me about 40 minutes to walk to school, but the combined time of waiting for a bus, maybe catching one, or maybe not catching one, because it might be full, and then all the stops along the way, was about 30/35 minutes in general.

So I could actually not pay money, not be annoyed waiting, and get a good walk in, rather than the frustrating sardine can of the university bus. It was a big improvement in my life that from then on. unless it was minus 30, I walked. It’s amazing.

Matthew: I had something similar. This past week, my father-in-law was in the hospital. And the elevator in the hospital was just ridiculously slow, and of course, tended to stop at every level all the way up. Now he was on the 9th floor. So you’re walking nine floors, that seems a bit crazy. But I wasn’t getting much exercise then because of going back and forth to the hospital. So I started taking the stairs. The crazy thing is, I would notice people getting on at the first floor and getting off at the ninth floor. And we were about the same amount of time. So in the same amount of time, I was less frustrated, because I didn’t feel like this annoyance of the door opening and closing. And I got exercise then. So yes — sometimes just try something random that can really improve your life.

Len: Yes and questioning the things you do just because everybody else does it that way.

Len: That was my trap with the bus. Everybody took the bus. And I hadn’t examined the assumptions behind that decision or even its effectiveness.

One interesting example that you bring up from the book, Messy. We’ve been talking about automation, but there’s also autonomy, which can be really important in how people are — how productive and how creative people are. And there’s a really interesting example of office design, and kind of business/cultural decisions like those made by Steve Jobs initially at Pixar, that can actually make people less productive, by taking over their control. I was wondering if you could talk a little bit about your thoughts about that?

Matthew: We all know the problem. When you open a piece of software or you get a new computer, you have a new desk, etc., there’s this deep temptation to want to tweak everything. And if you sit down and you just basically play with the settings all day, you’re never going to get anything done. On the flip side, if you make an environment where it’s so unflexible, where no one can get anything done — that’s bad too. Sometimes you need you need that control. You need a level of self-control, where you say, “Okay, I’ve done tweaking, this is good.”

And so in that example about Steve Jobs: basically he was trying to find a way to do what Zapier is doing with our random meetups, where he wanted a way to make the office floor plan force people to bump into each other and chat about random stuff while they were going to the restroom. And it was wasting time, it was making life more difficult for employees. That pushed employees to stand up to even someone like Steve Jobs, and he finally backed down. And so that amount of self-control, or autonomy — where people can influence their own workplace — gave them a happier workplace.

Remote is a great thing for that, because everyone can say how they want to work. If you want to sit on your couch — if that’s good for you, go for it. But then at the same time, that comes with responsibility. You need to be able to focus, you need to be able to not tweak everything all day long. Not tell Steve Jobs the entire design is bad and start over. You need to know what is a good limit, and then get your stuff done. So I think it’s trade-offs. It’s a good thing to learn how to handle right.

Len: One of the examples, I believe, from that post, that I found quite striking was, there’s talk in the last few years about creating office environments where people don’t have their own desk. And even prior to that, don’t have their own office. But the more radical version is, you have your laptop or whatever tools you use, and you carry those around with you. One thing that can result from that is that people actually feel alienated by the space.

Matthew: Absolutely.

Len: Because you can’t put something down and have it be there the next day. Because if you leave it, it’s then in someone else’s way, if they want to use that same spot. And so you don’t really feel a connection to anything. You might have a locker, but that’s not a very nice way to go to work.

Matthew: Yes. And some people are very social, they can sit down beside someone else at a table, strike up a conversation, make it productive and then get back to work. Other people, that’s intimidating. Having to go up and start that is a little bit of dread to add to every interaction in the day. As a good solution, I honestly don’t know for an office environment.

I do know one thing that works for me. I have my home office. It can be however I want it to be. But then some days I need the spontaneous-ness of a coffee shop or a co-working spot. And there I’m grabbing a random seat, next to a random person. Maybe I’ll chat with them, maybe we won’t? But at any rate, it’s that messy environment. Maybe companies need a desk for each person, and a random work space — to combine the both of those? I don’t know. But I do know that at least you definitely need somewhere that feels like you can sit down, just do work, without having to think about extra stuff.

Len: Moving on to the Zapier books that have been created using Leanpub, and have been published on Leanpub. I wanted to ask you a little bit about that. Producing content is a big part of your job, and a big part of bringing attention to Zapier, as I gather. I was wondering why you chose books as a product to create?

Matthew: First it was two things. One is content strategy. Writing a book gives you a focus. If we’re going to write a book about G Suite, we need to have that set of content about G Suite. We need to walk people through it, we need to think through what we’re going to talk about over the next few months. And often with a blog, it’s easy to just write your next idea. That can work great for a while, but eventually you’re going to need something that ties things together. Maybe it’s not going to tie every single piece of content you write together. But having that strategy for, let’s say, seven to ten blog posts, can be a great thing.

So for Zapier, we publish the content on our blog first, as blog posts. We’ve got this ovearching strategy that, “Okay, in three months this content’s going to go together and be released as a book.” That gives you a chance to re-promote that content again, and people see it with fresh eyes: “Oh, now it’s an actual book.” When you read through it together, hopefully you’re going to learn more than you would from each post on its own.

It gives us a great way to get in new markets. So your blog is on your own site. A book, you can put on the Kindle Store, on the iBook Store. You can literally email it to people. You can use those pieces of content as individual articles, or you can send the whole book when someone has a problem. If you wanted, you could print it, if you actually want a physical item. I’ve heard from many people, that’s a great way to give away stuff at conferences, and as another way to share your brand.

Our books maybe aren’t the exact same as a full publisher’s polished book. But they do both give us content strategy, help us share content, and, I believe, provide value for our readers. We’ve had people write in and say that they learned a lot from them. Hopefully it’s something that we’re able to give the community.

Len: I noticed for the remote workbook, it’s really interesting. It’s explicitly set up as something that’s going to be updated as Zapier’s ongoing journey with being 100% distributed team continues, and I was wondering, how often does your team update that book?

Matthew: For that book, we’ve done two editions so far. We’re planning the third right now. The remote stuff is interesting, because companies feel a lot different at different team sizes. When it’s you and your co-founder, it’s one thing. When you’ve got a dozen people, it’s another thing; when it’s maybe three, four dozen, and then you hit past 100, the dynamics change. That’s true for any team.

For Zapier, we’re trying to focus the remote book in that perspective, of, here was phase one. Things that worked at that size, may not work at phase two. So now we write about that. Now, you’ve grown again — it’s time to do that again. For this book, we’ve kept the content online, so you can still read the original version. You can read the second one. And once we release the third one, we’ll keep the old one around as well, as a way to go back and see, “That’s interesting. They wrote about communication in this chapter. Communication for a small start-up that’s remote, works this way. For a slightly larger team, might work this way.” Hopefully that’s a good way for people to compare.

Matthew: Now the way books are written and the way even most CMS systems are designed, that comparison is difficult. You have to clip back and whatever. One day I hope that there would be a better way, where you could have more living content, sort of like a Wiki, but in a less technical manner, where people can look through those changes. Because I think that’s a fascinating thing, to be able to see how content needs to grow over time.

Len: That answer may have already answered my next question, but can I ask why you chose to use Leanpub to create your books?

Matthew: Well, this is probably not the greatest answer, but frankly it was the most logical decision we could’ve made. I was testing software, trying to find what would be the best way to make a book. I tried using Pages, I used Ulysses. I tried Scrivener. I had used export tools that would turn your plain text into EPUB files. And frankly, everything works. Everything will let you make an EPUB file. What you often still end up with though is just slight little compatibility issues between that export and the ebook stores.

So, I would make these EPUB files, and try to upload them to the iBooks Store, and it would inevitably have errors. Honestly, even when you were exporting from Pages, which is made by Apple as well, you would get some weird, cryptic error. You would have to literally open the EPUB file, which is a zip. It’s XML files. You can edit the actual code in those XML files, zip it back up, change the extension to EPUB again, re-upload it to the iBook Store — and it’s like, “Oh now you’ve got these five other errors.” So you repeat the process. Which was mind-numbingly crazy.

So I tried more stuff, and came across Leanpub, and honestly, the biggest reason we used it for that first book was it made EPUBs that actually worked the first time with iBooks. We had no errors — just uploaded it, boom it was done. It was like, “Oh okay, this is a revelation. We are totally going to use this going forward.”

The other things that made it a great platform for us, were — it uses Markdown, and that’s how we write already. So we take our blog posts, we edit them to remove — obviously there’s stuff you’re going to have in your blog post that you don’t want in the book, maybe even code blocks or embedded videos etc. So you have to think of those too. Download that content. Basically the formatting’s already done. You save that to Dropbox, and you add it to Leanpub. And then for updates, I can just edit a text file, the five words we changed, or whatever. And hit re-publish on Leanpub, and boom you’ve got your EPUB, PDF files again. So it’s worked really well for us.

Len: I just wanted to mention, that’s really good to hear. When you work on something all the time, as we do on Leanpub, you can often have an exaggerated relationship to its flaws, and sometimes lose sight of the fact that it may actually be working really well for people. I say that not because I don’t have confidence in Leanpub, but just because — like I said, when you’re that close to a product, it’s… anyway, it’s very nice to hear stories like that.

My last question is: If there were a single feature we could build for you that would improve Leanpub, or perhaps add to its usefulness for your purposes of marketing, what would that be?

Matthew: With the caveat that this would be the kind of thing that would make you want to sit and tweak it forever: it would be great to have more design options. To be able to tweak the layout, tweak the typography you’re using, your page sizes etc. For us, when we’re starting out, as just plain text books — it’s easy to just use the plain text options. And obviously with EPUB, that’s all that’s going to be used anyhow. You really frankly can’t make a Kindle book look much nicer than it’s going to look. It’s just text. And your reader is going to tweak the fonts on their own device.

But with PDFs it would be really cool to have, not all the features of InDesign or something like that, but just where there was a bit more control over the design. I know some things have already been added in that respect, so it’ll be cool seeing how that continues improving.

Len: As you invoked there, it is this delicate dance. One of the reasons that — though not necessarily in your case — people often do have trouble creating their own book files, and then getting them onto online services, is that they’re doing all kinds of bespoke, very detailed formatting type-things, and that can confuse the software that generates the book files.

At Leanpub we have this sort of tongue-in-cheek saying that while you’re writing your book, formatting is procrastination.

All creative types know the temptation to start tweaking things. And then you end up enjoying yourself doing that, but not really getting the core kind of deep work done.

Matthew: It’s so deceptive. It feels like you’re getting stuff done, and all you’re doing is changing your file name or you’re tweaking your typeface or whatever. That’s why Markdown is a great thing. I use iA Writer, which has almost zero features. You almost can’t change anything, including the font. You can’t change the font, you can’t change the colour. You can change the size a little bit. But for the most part, you literally have to write. You just sit down and write. And that’s the great thing about it: there’s nothing to tweak. And it forces you to focus.

Len: By offering fewer options, it’s easier to standardize output. I had a recent example where people can upload Word documents to Leanpub, or they can actually write in a Word document in a Dropbox folder, or on GitHub. But we have deliberately very limited support for the features in Word, and one thing that was happening when a couple of people were trying to generate books from their word documents, they would get these weird kind elements showing up in text. It had been bugging me for quite some time, and finally it surfaced to the point where, “I’m going to solve this fucking problem.”

And what had happened was, when you create a table of contents in a Word document, it creates hidden bookmarks for each clickable item that will appear in the table of contents. And so even if you delete the table of contents, those hidden bookmarks stay in the document. So I discovered this, after poking around. You have to go to bookmarks, and you have to click “hidden bookmarks,” and in a big book you can have hundreds of these. You could only delete them one at a time.

Finally I found some VBA code online, where you can do that and sort of get rid of them all at once. And it worked like a charm, but — I’m just bringing this up to say, people might be surprised to hear why can it be difficult in 2017 to put a bunch of words together, and create an EPUB file that just works in iBooks. It’s because of issues like that. That’s a sort of deep reason for standardising and simplifying the way books are written. For example, with Word, if I open up a 20 page document, I’ll get the beach ball and slow scrolling.

It’s because it’s loading up mail merge options, which you can use to create letters, and supply a list of addresses and names. But say I’m writing a novel — why am I using this like a Rube Goldberg machine to do something very simple?

That’s sort of a broad technical explanation for why adding new formatting options can actually be something that one actually needs to take quite seriously.

Matthew: This looks back around, I think to our discussion before. This is why automation hasn’t won yet, and probably is never going to win 100%: there’s always crazy things like this. If we can’t even get these kind of things to work, there’s always things that you can automate that are going to help your life and that are absolutely not going to take away your jobs. It’ll just take the pain out of it. Another thing: seriously people, use Markdown, use plain text — it’s so much better. You will really be grateful once you switch.

Len: I couldn’t agree more. One thing that is interesting is how difficult it is sometimes to convince people to switch away from writing and word. We talk about people internalising their oppression. Using Word is just way more complicated than using plain text. Like with the hidden bookmarks. People often — and this is not a blaming thing or accusation — how could you possibly know that Word is doing all this crazy stuff in the background of your document? You don’t even sometimes know the problems that you’re creating for yourself by using something, if it’s the only thing you’ve ever used.

Matthew: Word’s designed for paper. And so the tools that are there are designed to make something look nice on a printed sheet of paper. If you’ve written your copy and you want to use Word to format it and print it right there, it’s great for that actually. It’s good at that intended purpose. It isn’t great for writing every single random thing that humans need to write. Unfortunately, that’s the job it’s been given. People use it for every single thing. Really all you need is Notepad or TextEdit. Maybe a slightly shinier app if you want to spend money. But all you need is somewhere to type. You could literally write your next novel in iMessage. It would work, because all you need to do is type.

Len: That’s interesting actually. We recently released a new product we call our visual editor, which was designed specifically for people writing novels. What we did was, we realised the solution was to just radically simplify the options that we offer people. So in our editor — where you don’t need to, you don’t need to learn. Part of the purpose of it was so that people wouldn’t have to learn Markdown. I think that in the future, like in 20 years , writing like that will become much more familiar to people as everybody takes programming in school and stuff like that.

But for now, for a lot of people, they hear the word, “Markdown,” and they’re like, “What? That just sounds like something I don’t want to even go near.” So we made this visual editor for people like that. And it’s a totally fair and legitimate and understandable thing. And the only options that you have are italic, section, and subsection. I believe that’s it.

Matthew: Wow, no bold?

Len: No bold, not right now. We’ve already had a request for it.

Matthew: That was a bold decision.

Len: That’s right. But one of the reasons is — when you think about it, when was the last time you saw bold words in a novel?

Matthew: That is true.

Len: Italics are there. But other than that, it’s just, as it were, normal text and italics,and then chapter headings

Sorry I missed, I knew I would miss one. We also have scene breaks, which is a little line that divides one part of the text from another. That is something that’s pretty common in certain genres of fiction. We’ll iterate over time, and respond to people as they get in touch. But that was partly there to address the same kind of issue that you were bringing up, by saying that people evolved to use Word for everything. If you had a dedicated novel writing tool, it probably wouldn’t even offer the opportunity to make a link. When was the last time you bought a book at the bookstore and brought it home and had a link in it?

And for non-fiction obviously, links in eBooks will obviously be very important. But for fiction, not necessarily at all. If you want to use all these powerful, other types of features, then Leanpub offers you them in other modes. But we’ve just got this one really focused mode that doesn’t let you do any of that.

Anyway, thank you very much for doing this interview. I really enjoyed it. We covered a lot of ground, and it’s always nice to circle back at the end as well. To have a consistent theme.

So thanks very much for doing the interview. Unless there’s any questions you’d like me to ask you that I’ve sort of not addressed?

Matthew: I think we’re good. It was really fun. Thanks for having me on today.

Len: Okay, thank you very much. Thanks a lot, that was really fun.


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