Recent Posts On Writing, Publishing, and Ebooks

Leanpub sponsoring BattleSnake (a student AI programming contest, Feb 20, 2016) at UVic. We need books for prizes!

by Peter Armstrong

published Feb 04, 2016

If you are a Leanpub author and you want to donate copies of your book(s) as prizes for BattleSnake, a student programming contest, please email a free coupon for your book to! The uses limit on the coupon should be anywhere from 25 to 200, depending on how generous you feel :)

Long version:

We’re a startup based in Victoria, Canada. Another startup in our building, Sendwithus, is putting on a student AI programming contest called BattleSnake ( at the University of Victoria (UVic). Leanpub is a “Unicorn Sponsor” of BattleSnake, since we think it’s a cool event.

Anyway, besides helping pay for the event, as a sponsor we get to donate prizes which are earned by student teams which defeat our “Bounty Snake”. This is an AI bot (a “snake”) which will fight other snakes coded by the student teams from UVic and other local schools which are participating in the event. If a student team defeats your Bounty Snake, they get a prize.

Now, after learning about the event, I realized that many of our authors have written books which would be excellent prizes for students who are entering a programming contest.

So, Leanpub is going to code a Bounty Snake AI. Every student team which can defeat it will get prizes of Leanpub books, chosen from among the Leanpub books volunteered as prizes by Leanpub authors.

We expect that there will be between 100 and 200 students who participate. So, what we’d like is for authors to email a free coupon for your book to! The uses limit on the coupon should be anywhere from 25 to 200.

(We’re also going to donate our office Xbox One as a prize, since it’s just sitting there unused – the only game we actually play at Leanpub is Super Smash Bros on our Wii U. The plan is for this to be a prize for one of the students chosen at random from the team which defeats multiple instances of our Bounty Snake on a large board in the shortest amount of game time.)

A Crazy Little Hack For Getting Large Book Files Into The Kindle App On iOS

by Len Epp

published Jan 21, 2016

At Leanpub we have strong opinions about the deep connection that exists between a product, marketing, and customer support; for me personally, they are just different ways of looking at the same thing.

As a result, we have an “everybody-should-do-a-bit-of-everything” philosophy (the fact that we’re bootstrapping Leanpub makes this even more important and desirable). One popular objection to this approach is that it causes a lack of focus, but the fact is that a too-narrow range of knowledge and interests in any endeavour results in what you might call “false focus”. Put crudely, if you don’t understand how everything fits together, you might do something that makes it all fall apart.

Recently, I had an experience where “everybody-should-do-a-bit-of-everything” meant “Len-you-need-to-see-if-you-can-fix-an-insane-problem-someone-is-having-with-someone-else’s-product”. Normally we don’t do customer support for other people’s products (though of course we do try to understand them if they are important), but in this case the customer was having a problem with the Kindle app, and since the Kindle app is pretty popular with a segment of the ebook-reading population, I decided to dive in and see if I could fix anything. This would also have the side benefit of helping me to understand the customer’s experience, update my understanding of how the Kindle app works, and assuage my guilt at not understanding Kindle stuff like a pro for a personal reason, which is that I hate using it.

The problem was that a customer had bought an ebook bigger than 50mb. Now, since the ebook was larger than 10mb, he couldn’t use the handy “Send to Kindle” link that we provide to our customers for books which are less than 10mb. However, since the ebook was larger than 50mb, this also meant he couldn’t get it into the Kindle app using the Send to Kindle apps that Amazon produces. Specifically, he wanted it in the Kindle app on his PC and in the Kindle app on his iPad.

Now, that might sound like a banal problem, but when you think about it, this involves resolving an issue simultaneously involving Microsoft and Apple - who have competing operating systems - and Amazon and Apple - who have competing ebook stores and apps. It’s like asking a bunch of territorial animals to share the same space and just get along.

Anyways, after many twists and turns, I found a crazy hack to do this, and thought I’d share it, since when you check Google about this what you will probably find a mess of outdated answers and a really, really frustrating problem-solving rabbit hole of comments and suggestions.

So without further ado, here’s my little hack. To me it’s a little crazy because it uses a weird combination of features, and from what I can tell it’s causing the Kindle app in iOS to behave in a strange way - you’ll see.

This is how you can get a book larger than 50mb to show up in the Kindle app on your iPhone or iPad.

Before you begin, please make sure you have Dropbox installed on your iOS device.

1. Put your 50mb or larger .mobi file into a Dropbox folder and navigate to it in the Dropbox app on your device.

2. Click the little circle to the right of the filename.

4. Click the “Open In…” icon.

5. Wait for the book to finish exporting.

6. Click the “Copy to Kindle” icon.

7. Wait for the book to export again.

8. Hurray! You’ve got your book in the Kindle app. But wait!

The reason you won’t find the book under Books is that Amazon only shows books you bought on Amazon in the Books section of your library, at least as far as I know (remember I said I hate using this stuff). Other books you get into the app will usually appear in Docs. But in this case, you won’t find it there either.

To find the book, you either have to search for it:

or go to “All Items” and select “Device”:

If you have a better way of doing this, please let us all know in the comments below.

Leanpub Podcast Interview #26: Emmanuel Nataf

by Len Epp

published Jan 20, 2016

Emmanuel Nataf is the cofounder of Reedsy, a marketplace for high-quality publishing services that helps authors find professional editors, designers and marketers. In this interview, Leanpub cofounder Len Epp asks Emmanuel about how Reedsy got started and about their vision for the future of publishing.

This interview was recorded on November 5, 2015.

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

Emmanuel Nataf

Len Epp: Hi, I’m Len Epp from Leanpub. In this Lean Publishing podcast, I’ll be interviewing Emmanuel Nataf, in the first instalment of our Friends of Leanpub interview series.

Emmanuel is cofounder of a London-based publishing startup called Reedsy. Reedsy was founded in 2014 by Emmanuel and his co-founders Ricardo Fayet, Vincent Durand and Matthew Cobb, with the goal of providing a marketplace for high quality services that could be used by anyone self-publishing a book, services like editing, marketing and design.

In this interview, we’re going to talk about how Reedsy was founded, what it’s currently up to, and what its plans are for the future. So, thank you Emmanuel for being on the Lean Publishing Podcast.

Emmanuel Nataf: Yeah, great to be here. Hi, Len.

Len: Thanks. I guess the first thing I’d like to do is ask you about Reedsy’s origin story. How did you guys come up with idea and how did you get started?

Emmanuel: So basically I think it all started when I was actually still in college, and I got my first Kindle. I actually imported it from the US; I was living in France. I couldn’t buy it in France, it wasn’t availablem and I imported it and I realized how amazing it was to have all your books in just a little tablet. I wasn’t that much of a reader before that, and actually getting a Kindle made me a reader. I started to read more and more and learn about the industry, and it actually took me years before we actually started Reedsy.

Initially, I was learning about the self-publishing space. For a year I was interviewing people from the industry just to learn about it - authors, editors, designers. And then at some point I think I read an article and the writer was saying how the best publishing professionals have left publishing houses and started to work as freelancers.

So I saw that there were two trends evolving together, basically. One was the boom of the self-publishing market with hundreds of thousands of writers pushing their books to the Kindle store every year. And on the other hand, great professionals available in the market to potentially work with them. And at that time I started to look for professional editors, designers, and I realized that there was nothing to provide high quality services to indie authors. So in a way, I was a bit frustrated that there self-publishing wasn’t a real alternative to traditional publishing yet, because you couldn’t find that level of quality you’d find at traditional big five publishers. So that’s basically where the idea comes from, learning progressively about the industry.

Then I started to build a team. Initially I started Reedsy with Ricardo, who is running the marketing at Reedsy. And then since we didn’t have any technical skills, we added Vincent, who is our CTO, and Matt, who is our designer. And then progressively it became a side project during evenings and weekends. And last year, mid last year, we applied to get into Seedcamp, which is a start-up accelerator based in London. We got selected for it, and we thought that was a great opportunity to become full-time on Reedsy. So the French guys moved from Paris to London, and we’ve been working from here since then.

Len: The quality of freelancers on Reedsy is one of the most important aspects of your company. I was wondering, how do you find and then vet freelancers?

Emmanuel: Initially, when we started, we contacted a few professionals manually that had worked with traditional publishers, because they could provide the level of quality we were looking for. We told them, “Hey, we’re setting up Reedsy. Could you be interested in being one of our first users, one of our first service providers?” And we progressively found a few who loved the project, started to use the product and thought the interface was really incredible. And they could create profiles. Basically, progressively I started to show these profiles to other professionals who would tell me, “Oh, that’s really amazing. I want to be part of this community as well and join”.

That’s how we started. We started to grow our supply side with a strong focus, as you said, on quality. What we did was, we built this profile, kind of a LinkedIn, but for publishing, where you have a quick overview of who the professionals are, different genres they work on, their work experience and a portfolio of books they’ve worked on, with links to Amazon or the Google Play Store. And then we could take a look at the quality of the books they had worked on, and in some way verify their identity, their online identity as well.

That’s how we started, and now it’s completely different. Now we’re getting tons of submissions every week, probably hundreds every week. So far I think we’ve received over 7,000 applications, and selected 330 professionals, only keeping really the best people in the industry, and growing based on the demand we’re getting. So if a publisher or an author comes to us and says, “We have” - I don’t know - “a photography book that we’d like a designer for”, then we’re going to start looking for people who could work on that kind of genre.

Len: Because Reedsy is inherently exclusive - I read a good article about Reedsy in Forbes - obviously some people who are excluded are a little bit unhappy about that. How do you deal with that?

Emmanuel: Unfortunately, we don’t compromise on quality, and we never accept people if we feel like, you know, if we feel like there’s something wrong or it’s not going to work. Even worse is, if we see that something goes wrong, even after accepting the professional, we take that person off the marketplace immediately. We don’t compromise on quality, and some people get pissed off. And there isn’t much we can do about it. At some point we had I think an editor with about 20,000 followers on Twitter who started to rant about it. But we were like, “Sorry, you’re good at social media, but you’re not the editor we’re looking for.” And it’s - it can sound harsh, but that’s why people love our service. They feel like they can come to Reedsy and they don’t have to think about whether that person is legit or not. They know that they’re working with some of the world’s best publishing professionals.

Len: And you also have a hundred percent money back guarantee, is that correct?

Emmanuel: Yeah, we’ve had it more or less since the beginning, but we didn’t make it official; but a few weeks ago we decided to release our Reedsy trust and guarantee policies. So now, if anything happens, you can just reach out to the Reedsy team. There’s a button in the interface that’s present the whole time called just “Help.” If you reach out to us and you say, “The freelancer didn’t come back with the work he was supposed to deliver” or, I don’t know, “I’m not happy with the quality or anything”, then we try to solve the issue, and we refund if it’s necessary. It’s happened once over a few hundred of collaborations so far, so it’s pretty rare. But if anything happens, we have those guarantees.

Len: Fantastic. I was wondering at what stage of their writing do you find that authors, self-published authors, start to approach Reedsy in looking for professional help?

Emmanuel: There’s still a lot of educating that’s needed, because tons of authors come to us at the wrong moment, at the wrong time, basically. They come to us while their draft is not solid enough or the story isn’t even - they haven’t even finished writing it. And we’re very different from Leanpub, because we don’t work on books that are not finished yet. We mainly work on books that are - like you have a solid first draft, or a solid draft, because the first draft is not always solid. And you can come to Reedsy and request quotes from editors and then designers. And the same thing for publicists; so we’ve recently added publicists to the marketplace and you can come talk to our publicist if you have already released your book, for instance. So there’s a lot of educating around when you should come to Reedsy, that we’re trying to do. And we’re actually going to publish more blog posts about it to help authors understand when they need an editor, when they should start marketing the book, when they need a publicist, when they need a designer.

Len: I was wondering how pricing works, and how Reedsy makes money?

Emmanuel: Yeah. So, pricing is completely transparent. There are very few people who can compete on quality with Reedsy basically at the moment. But the only guys who can, are very, you know, there’s no transparency at all in terms of how they price the services. So you can find local agencies in San Francisco and New York who are going to offer their services to you, but you have no idea if you’re actually paying the right price or not.

What we did here is when you go on Reedsy, you can request quotes from up to five professionals. And those people get back to you within a couple of days with quotes or more questions if they need more to offer, to send you an offer. And then you can see the different pricing. So we don’t set the price, our professionals do, and then you can compare the different prices and make a decision. But it’s completely transparent and we display our fee on the offers page. And you can see that Reedsy charge a 10% commission on the author’s side - that’s what you see.

Len: Okay, that’s really clear, thanks. I was wondering, more generally about the publishing industry. There was an article in the New York Times, I think a couple of, three weeks ago now even, that talked about how ebook sales had dropped. Did you come across that one?

Emmanuel: Yeah.

Len: There was a bit of a controversy about it, because it was a false report. What had happened was, probably, with respect to sort of publishing industry stuff, a conservative journalist at the New York Times basically just looked at the data that comes from, I guess I’ll call them the conventional publishers, who, in many ways, have been actually hostile to ebook sales. Many of these publishers had actually increased the prices of their ebooks on Amazon, and then their sales went down, surprisingly.

Emmanuel: Yeah.

Len: Anyway, there were lots of really great responses to that from people in the sort of - let’s say 21st century publishing world, pointing out that actually ebook sales have been increasing, and it’s just for these people, the people sampled by the data set cited by the New York Times, that had fallen. And I was just wondering what your thoughts were about that, when you noticed that?

Emmanuel: Yeah, so there’s two things. The first thing is like - there was no 50 Shades of Grey this year, basically. So as a result, since it was - there’s been a crazy number of copies of that book that were sold. There’s probably quite a lot of - well Penguin basically probably sold less, fewer copies, and probably impacted that survey or that report. But on top of it, there are so many titles - titles are not tracked properly, because they don’t have an ISBN. So, I’m not sure how it works on Leanpub exactly, but on Amazon, you can publish without having an ISBN. So, it’s data that’s harder to track. Only Amazon’s got the right data about the industry, unfortunately. But I have like, just as a feeling being in the industry, I don’t see it like - I see more and more people reading on the tablets. And I find it weird to hear that fewer ebooks are being bought by consumers. I find it - I struggle to believe it. But that’s not that I don’t have - nobody’s got the data to basically back this up. So it’s kind of confusing, but I would find it very weird.

Len: Yeah, to be clear, on Leanpub we actually don’t require ISBNs.

Emmanuel: Yeah.

Len: I don’t want to speak for everyone else at Leanpub, but personally I see it as a form of rent seeking. There’s this one company that owns the ISBN issuing rights [Correction: There is one company responsible for issuing ISBNs in the United States. Other countries have other institutions for issuing ISBNs. - Ed.]

Emmanuel: Yeah.

Len: And they make money just issuing numbers that allow people to track books. And the way I look at - the metaphor I use is like dark matter. From the perspective of the conventional book publishing industry, a lot of what’s happening with publishing now is stuff that they just can’t see. For example, if someone makes a really high quality book and puts it up for sale on their own website or Gumroad or something like that.

Emmanuel: Yeah.

Len: Or on Leanub, where we hope they would put it.

Emmanuel: Yeah.

Len: Then it’s not tracked, because we don’t do that and they don’t do that. And so yeah, so the idea that like the entire world of books is something that is brought -

Emmanuel: Trackable.

Len: Yeah, it’s trackable, but it’s particularly that if you want to be an author, you have to be brought into an incumbent system like a panopticon or something like that.

Emmanuel: Yeah.

Len: This is something that people are kind of leaving behind. And so, that’s one of the reasons I was so interested to talk to you. Because you’re, in my view, you’re obviously providing people who are behaving - we use the term “independently,” right? But we shouldn’t even have to use that. The reason we use that term is because it’s differentiating from the past. Where people couldn’t do things on their own.

Emmanuel: Yeah, exactly.

Len: Because it just wasn’t done or something.

Emmanuel: Yeah… I wish Amazon would release data like once a year. So at least we’d get a better idea since they sell most of the ebooks available. But yeah, I don’t have that feeling…

Len: Yeah, I know that actually–

Emmanuel: Yeah.

Len: They do seem to be able to get quite a bit of Amazon data, do you know how?

Emmanuel: They basically - well they make assumptions basically, to be able to build their model. Which is - it seems to be kind of accurate, but I’m not sure. As much as I like Hugh Howey, I know he’s been working with Amazon a lot, so I have no idea whether the data is accurate or not. But yeah, when you look at the New York Times and when you look at authorearnings, like completely different pictures basically.

Len: As a sort of really high level questionm, where do you see the publishing industry going in like, let’s say the next 10 years?

Emmanuel: That’s a tough question.

Len: Yeah.

Emmanuel: So the publishing industry in the next 10 years, it’s interesting, it’s something we see already at Reedsy. The rule of publishers is changing. There is that need in the world of abundance for curation. And I guess it’s the one thing that I like that publishers are doing. The fact that they curate content. You may not like it. I mean, you may not like the selection, but at least they’re here to say, “Okay, we’re Penguin, we think this is a quality book.” And I think it’s important worldwide there’s so many low-quality books that are being pushed to online stores. And so the rule of publishers is going to change completely.

I was talking to an author who was telling me, Reedsy’s making quality editing, quality design a commodity. So suddenly the rule of publishers is changing completely towards something that’s more about like being a curator mainly. So I think this is pretty interesting. I think we talked about it together last time, but the fact that people are reading more and more, on their tablets, on mobile, in a very mobile way, is very interesting as well. And I guess it’s taking time before ebooks are replacing traditional books, but I think it’s going to happen more and more in the coming years. I can see [mobile] books dominating the market in five to ten years. Maybe that’s just me.

Len: It’s interesting you’ve mentioned tablets and Kindles a couple of times. I used to live in London, and I remember commuting on the expletive Northern Line, and I would have to kind of work out - it was so packed that I would have to make sure that my book could fit into my coat pocket, and that I could pull it out and fold it in half, so that I could hold it right in front of my face to read it.

Emmanuel: Yeah.

Len: And I really wish that back in those days I’d had books on my phone, that I’d had a phone that wasn’t a flip phone or whatever and that–

Emmanuel: Yeah.

Len: So I’ve always thought that actually one of the main ways people are going to be reading books is on phones. And you see this happening in the increasing size of smart phones, right?

Emmanuel: Yeah.

Len: Because people are consuming content on their -

Emmanuel: Yeah, that’s something I’m a bit frustrated - even though I love my Kindle, I feel like the experience for reading content or - even if it’s just colours, it’s very - I mean there’s so many things you’re missing on the Kindle. And I hope there’s going to be new versions of screens that are going to provide much higher quality - a much higher quality experience with the benefits of e-ink technology.

Len: What’s the most important aspect of Reedsy that you’re working on right now, in your opinion?

Emmanuel: I guess it’s becoming more and more full stack. So providing a full stack experience for authors. We’re working on a collaborative book editor for instance. So an editor, where you have the experience of Medium, the blogging platform. And the collaborative features of Google Docs. So you’ll be able to come to Reedsy and start writing your book, go import it from the Word document or rtf or whatever you’re using. And then invite a co-author to work on that, or your editor and then in one click be able to export it into a properly formatted EPUB file or PDF. Something similar to what Leanpub did, but for - say for the mass market. I think this is going to give a much more interesting experience to authors on Reedsy as they’re going to be able not just to send messages with files through Reedsy, but also to collaborate directly with the professionals they hire. So there’s editing, and on top of that, also adding more services to the marketplace all the time. So we started with editing and design, which are the basic services you need to produce a final book. And we’re progressively adding more services; last month we added publicity services, and we’ll be adding marketing, ghostwriting, and a few other services as well.

Len: You said something about the mass market, as opposed to Leanpub, and I guess I’d better push back a little bit on that. I’m not really sure what you meant?

Emmanuel: I meant a tool that anyone, I mean, without using Markdown for instance.

Len: Understood, thank you. Okay, yeah.

Emmanuel: So someone who is not into tech at all can start writing a book on that.

Len: Yeah we’re very - I just wanted to be clear about that, because that’s really good feedback to hear. We are working on something called Markua which is going to be basically - Markdown was written as a way to kind of easily write things on the internet, and we are working on a version of that for writing books called Markua. What we’ll probably end up with - I mean, I know you know this, but some listeners might not know, but with a WYSIWYG editor, which is basically what you see is what you get.

Emmanuel: Yeah.

Len: But yeah, so what Emmanuel is saying is very correct, which is that to date, Leanpub has been made by programmers, and mostly used by programmers. People who are very technical.

Emmanuel: Yeah.

Len: And so, it’s kind of like for a technical person, they’ve seen Leanpub, and they’re like, “Oh my God, that’s - I can’t believe someone built exactly what I wanted.” And for people who are non-technical, they’re like, “Why are you making me learn a markup language to write text?”

Emmanuel: Yeah. It’s almost a different product in some way, but I think it’s got its benefits as well. I mean lots of people will find it much better to write without all the HTML that we are going to have to add for authors in the “what you see is what you get” editor.

Len: Exactly, and that’s the - it’s interesting the position that Leanpub has taken, is to kind of radically - in a fundamental sense, it’s actually a radical simplification of the way things are done. But it means that you need to learn a little bit. The way I refer to it is, it’s like punctuation for digital writing. So in the same way that we all understand, we would see right away if we were writing, and we didn’t close off a quotation with the quotation marks at the end. We’re all trained just like - like programmers would see right away, “Oh, it’s not closed.”

Emmanuel: Yeah.

Len: And we understand that you have to put quotation marks before and after something, that’s meant to be something that is kind of a reference to something someone said or wrote somewhere else, or something that a character is saying. So we’re actually all familiar with a markup language.

Emmanuel: Yeah.

Len: It’s punctuation, but getting people to understand that punctuation can actually refer to the material production of the text, as opposed to simply kind of speech signs. So it’s interesting. And another analogy I use is like - at one point everybody learned how to use like keyboards and typewriters.

Emmanuel: Yeah.

Len: To write better, and so we hope that - this is all getting sorted out in very interesting ways, and it’s so great to see so many people applying different approaches to try and make it easier and better for people.

Emmanuel: Yeah.

Len: I guess the last question I have for you is, where do you see Reedsy being in five years or ten years? I mean you’re already expanding into new kinds of book tools and stuff like that. Where do you see yourself?

Emmanuel: Yeah, so at the moment, our objective is to become - in some way - the foundry of best-selling books. So we’d like to see, some of the most interesting books being produced via Reedsy. So working with our professionals, or potentially with our tools, and then seeing them published. Basically we - our objective is to help the publishing community publish beautiful books, and that’s the obsession. But where we want to be in a few years’ time, well we’d love to provide services to as many self-publishing authors as possible. But we also started more recently to work with publishers, who came to us and told us, “Well we’ve seen the level of quality you can provide, and we love the fact that you can streamline our workflows with the collaborative tools that you’ve built. And so we’d love to use Reedsy as well.” So we’re currently building a product for them as well. So it’s making Reedsy in some way, the backbone of the industry, when it comes to producing books.

Len: That’s actually, I just thought of one more question I wanted to ask you.

Emmanuel: Yeah.

Len: It’s really interesting, Reedsy in many ways is reflecting changes that are happening elsewhere, just in industry in general, right? Where, so for example, people who might have previously been full-time employed - workers at a publishing house, have been booted. Just generally because publishers are doing that to their workers. And then they’re now stuck, now they’re in a situation where they’re freelancing, which means that they are kind of operating independently. Essentially it’s often like one person’s small business or something like that. And so service - when that starts happening, forward-looking people see this happening and go, “Oh well, I mean these people are going to need a way of - they’re still going to need a way of not being entirely fragmented, right? So we need to create a new space for them, that suits this new situation.” And I was wondering, in your experience talking to freelancers, are they - I mean, just asking you to make a blanket generalization, but like are they generally, do they prefer - I mean, assuming that Reedsy is a success at doing its core mission, right, which is creating this new ecosystem - do you they’ll be happier with that new situation than they were in the old one, or–?

Emmanuel: It’s very interesting. We see a lot of things developing for this new economy in some way. So the freelancer economy, you see companies like WeWork, who are going to provide office space or co-working space for all these people who work at - independently. But you also see tons of tools that are emerging. So there’s a really cool tool that I saw recently called Cushion, I think? Where freelancers can basically add all their expenses and get an idea of what the cash flows are going to be at the end of the month or at the end of the year, and how many new contracts they need to sign before they reach their yearly objectives. So there’s a bunch of things that are developing around it, to basically - to help freelancers have a more structured work environment. And I think this is very interesting. Do freelancers like it? Most of the time they left publishing houses because it’s a lifestyle they wanted. They wanted to be able to work at any time during the day or the night. To be able to go on vacation when they wanted. Maybe to sign contracts for six months of the year, and then the rest of year is enjoying the sun somewhere. I don’t know? But it’s much more flexible. It doesn’t mean that they won’t see a traditional work space anymore. Because some of them work still with traditional publishers, and go to their offices as well. So I think it gives them more flexibility and they’re happy with it. And it doesn’t mean that they have to stay by themselves at home, all day. I’m pretty sure there’s going to be like - well there’s - WeWork is an example, but there’s plenty of co-working spaces for creative people in the publishing media industry that are emerging, and I think are pretty cool to work from.

Len: Thanks very much, that’s a really, really great answer. Great balance. I mean it’s - anyone who’s ever worked in the old time-y, commuting-to-an-office kind of world, I think a lot of us see the idea of being more independent as a great change. A great social change.

Emmanuel: Yeah.

Len: Away from the kind of like factory floor with a kind of overseer, making sure everyone’s there on time and working hard all day. I mean this is something it’s - I think it’s great that we’re moving away from this and that -

Emmanuel: I think the book, Rework by Basecamp or 37Signals is like, that was pretty forward thinking, like just publishing it a few years ago, and now it seems like the normal thing to do for an old stage company. But like, even just a few years ago, that sounded weird. But like now you have the staff everywhere and more freelancers, and that’s fine.

Len: Yeah it’s interesting. I’ve got a joke that I tell where - for thousands of years, we had the concept of bastards. And that just went away, and we didn’t even really notice. It just went away, because it was dumb. And it’s amazing how these changes can happen where one day kind of people wake up and realize that - for example, like the stress and insanity of making an entire city’s employees at the same time in the morning all trying to get to specific places in one area. Is kind of ludicrous.

Emmanuel: Yeah.

Len: And that there’s much better ways we can organize our work together and to do higher quality stuff.

Emmanuel: Exactly.

Len: So thank you very much for being on Lean Publishing Podcast. This was a great chat, and I really appreciate you giving us your time.

Emmanuel: Pleasure.

Len: Okay, thank you very much.

Emmanuel: Thank you, bye.

This interview has been edited for conciseness and clarity.

Leanpub Podcast Interview #25: Jeff Geerling

by Len Epp

published Jan 11, 2016

Jeff Geerling is a full-stack developer, author and blogger. In this interview, Leanpub co-founder Len Epp talks with Jeff about his career, open source projects, his book Ansible for DevOps: Server and configuration management for humans, and how he made over $25,000 in sales before his book was finished.

This interview was recorded on October 16, 2015.

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

Jeff Geerling

Len Epp: Hi, I’m Len Epp from Leanpub, and in this Lean Publishing podcast I’ll be interviewing Jeff Geerling. Jeff is an experienced full stack developer, who creates websites and applications for organizations ranging from small businesses to large enterprises. Based in Saint Louis, Missouri, he’s involved in a number of open source development communities and maintains the Drupal VM project at Jeff also blogs, writing on various sites including his personal website,, and he is also a photographer whose pictures have been used in news publications, documentaries, and various places on the web. He currently works as a technical architect at Acquia, a cloud platform for building, delivering and optimizing digital experiences.

Jeff is the author of the Leanpub book, Ansible for DevOps: Server and configuration management for humans. In this interview we’re going to talk about Jeff’s professional interests and his experience writing and self-publishing a Leanpub bestseller.

So, thank you Jeff for being on the Lean Publishing Podcast.

Jeff Geerling: Thank you, Len.

Len: I usually like to start these interviews by asking people for their origin story. So, I was wondering if you could tell me how you first became interested in being a developer, and how you ended up with your particular specialties and interests.

Jeff: I like telling people about it because - and I love hearing also from other episodes of this podcast, other people’s stories - because it’s so amazing in our field of basically anything technical, how varied people’s backgrounds are.

When I was growing up, my dad worked for a radio station - actually a set of radio stations - as an engineer, here in Saint Louis. He would bring me to work sometimes and I got the opportunity to learn right as the internet was becoming a thing. The radio industry was picking it up, and they had a lot of local networking. They started connecting their offices together and they started needing more IT operations. Basically I went from a guy who liked playing games on an old Macintosh, to a guy who had experience with Novell and Microsoft and early Linux-based networking - in the course of a few years, when I was just barely able to work.

So he let me work on different projects that he had there, he helped me to build computers until the point where I could build them and I started selling computers. I was helping schools and organizations with their networking, and with their server set-up. Eventually that all led into being able to do some early web development back when it was using like Claris Home Page to build yourself a web page, and sticking a picture in there, that kind of stuff. I actually had a website with some pictures of mine on it, I think it was 1996, an IP address somewhere. I don’t remember where it was, but it was on an old InterJet. So I got into networking and computers mostly from the hardware side, that was my fascination back then.

As time went on, I went to seminary. I was studying to become a priest, actually. And when I found that that wasn’t for me, I was still doing stuff with computers at that point, and learning a little bit of programming. After getting a degree in philosophy, I started getting into Drupal, which is an open source CMS for building websites. And I just so happened to get into it at a good time, with the field of turning the web into content-driven websites that all interacted with each other. Drupal was hot at that point, and I kind of just hitched my ride on that bandwagon and started learning a lot more about Drupal.

And then, as time went on, I also was getting more interested again in infrastructure, and building sites and high availability environments on the cloud. And so, as time went on and I did shell scripting and I learned some Puppet and I learned some other configuration management tools and systems. Ansible came along right at the right time for me, because I needed to grow some of the sites that I helped with, a lot bigger. And once you get beyond a couple of servers, you need tools to interact with the services that you use and automate everything.

Ansible was introduced in 2012, and I got into it in early 2013. At that time there was no book on it or anything like that, so I decided, “I’ll start blogging on it,” and then the rest is history. The blog turned into a few chapters of a book, and that few chapters of the book turned into a Leanpub project, and now I’m here today with this book and a lot of involvement in both the Ansible and Drupal communities.

Len: You have a particular interest in open source projects. I was wondering if you could maybe tell about your first experience with an open source project, and how you became interested in that?

Jeff: Yeah, actually, I’ve been involved in a few here and there, smaller open source projects, and I’ve used Linux for anything server related for years so…. But I never really got involved in communities that much. I read The Cathedral and the Bazaar, and that got me interested in the whole idea of the movement of open source. I wouldn’t call myself a purist, by any means, but I do appreciate the value of having your work be open and free and available - free as in beer.

So when I got into Drupal and I noticed that the community had such a strong base of smart people working together, there were no real boundaries, like, you didn’t have to be a certain type of person, or you didn’t have to do certain things. You just had to have an interest in making Drupal better, and people would accept that. I found that to be awesome in that community. And I can’t say that every community has that, but a lot of the open source software communities do have that kind of atmosphere, which I love because you get to work with such varied backgrounds, and you get to do things that you’re interested in. As long as it’s something that’s helping the project, you’re going to have a future, and you’re going to get people to help you and you’ll be able to help other people.

So I really got involved in Drupal first, and that community is huge. There’s, I don’t know, like fourteen or sixteen hundred people that helped with the Drupal 8 release, that just is about to be released. They’re in release candidate stage right now. And Ansible also grew from when I started. There were may be a hundred or so different people contributing, to now there’s twelve or thirteen hundred people contributing, from a lot of different backgrounds, from big enterprises to little one-man shops. It’s really cool.

Len: You’ve brought up the fact that people can come to development and to different open source projects from different backgrounds a couple of times. It was actually something, when I was reading your resume before - when I was preparing for this interview, of course I noticed that you have a background in philosophy and theology, which is relatively unusual at least in my experience for developers.

This is slightly left-field, but I thought I’d take the opportunity to ask someone with a background like that, and with obviously deep IT experience, what you think about recent developments in AI and the discourse around AI. Because we hear from people like Stephen Hawking or Elon Musk, but not necessarily from people who have a deep background in different subject areas or - it’s a bit of a trivial way of putting it, but like you do.

So I was wondering what your thoughts are, given your background in philosophy and theology, on what’s happening with AI and where it’s going to go and what it needs?

Jeff: Yeah, it’s especially relevant now that were seeing things like Elon Musk announcing that A, we need to be cautious about AI, and B, all of his cars are now talking to each other and building up traffic networks and things like that. I think we’re at an interesting moment where AI is not just science fiction, but we’re seeing kind of small bits of it here and there being developed. And it might not be AI in the sense that something is going to take over the world and kill all the humans at this point. But it’s already to the point where we can create networks that evolve themselves, and do things like fix themselves or build something entirely new. But not to the point where you’d recognize that it’s human intelligence.

So you know, I have a background where I believe that the ends don’t justify the means, so I think, in my opinion, it’s always about taking it as far as you can go - but also taking the time in all your research and things that you’re doing to make sure, “Is this going to be supportive of the human race and the ability to be a human?” And really it all stems down to what you believe it is to be human. I could probably get into a long debate with most of the people listening to this podcast, because they’re all technical people, and technical people love getting in to the detail about, you know, morality and what it is to be human and ethics and things like that.

But it really comes down to making sure that you have some sort of morality that guides your decision-making, and I think whenever we run into problems, it’s somebody who kind of mutes that part of their life because they’re so interested in developing something further, going down a path.

On the flipside, you need to go down those paths, but you need to use caution and it seems that like every disaster in history is due to more hubris than anything else, the idea that we can take something further without worrying too much about the consequences because it’s science, you know.

Len: That reminds me of one of the potential consequences of AI. I’m sure that most people listening to this are probably familiar with the conventional understanding of the Turing test. Where you know, Alan Turing proposed this test that where if you’re interacting with a machine, and you can’t tell if on the other end, where there’s a thing in between you and the thing you’re interacting with, if it’s a person or a machine, then if it is a machine and you can’t tell if it’s a machine or person, then it’s passed the Turing test. I wrote a blog post about this from another direction a while ago, but when I was reading about you, and on your blog, I sort of thought that there’s an interesting metaphor there, for a priest being on one side of the confessional and not knowing who or - and potentially, in the future, what is on the other side of that?

For example, in a more trivial way, if we actually have computers, whether they’re actually thinking or not - if they’re sophisticated enough that they can mimic people, and we can’t tell the difference - what do you do, let’s say in a customer service situation? Or let’s say on a 911 call? It seems to me there’s a fundamental issue about how, and when you bring up, what makes us human. If we’re going to be in this very strange situation where relating to something that might or might not be a human, what kinds of decisions do we make about what to do? Especially if, let’s say, we can get kind of a denial of service attack or something, with all these things that actually look and sound like humans. But what do we do?

Jeff: That’s a good question. It’s one of those that I’ve - I try to spend more time not thinking about it, because, almost every road that my thoughts go down ends up in some sort of disastrous, crazy end-of-the-world scenario. But, I think it’s a question that all of us in the tech industry have to ponder at least somewhat, because unless you have your head in the sand, you see there are advancements everywhere - like the robotics, like the Big Dog, I forget what lab it’s from–?

Len: Oh -

Jeff: Boston Dynamics -

Len: Yeah.

Jeff: Their research, these robots are being built that can do things and manoeuver in ways that humans even can’t. And you mix that up with the networking and the brains that are being developed for other projects, and you start thinking, “It’s not going to be too hard to think of” - even if it’s not full AI, what happens when somebody can change the algorithm that detects human versus something else that needs to be cleaned up, or things like that?

For me, I’m always just trying to think, “Is what I’m doing right now going to advance the human race?” I don’t have that grandiose of a vision of this book, but you know in general, when I work on things I just, you always have to pull back and make sure, “Is this something that matches up with what I want the future to be - for me, for my family, for everyone?”

Len: There’s just one last question on this topic. Generally I know that there is a discourse amongst - sort of religious intellectuals, especially in the United States, about how the predominance of screens and the internet is leading to a form of isolation, where people are not interacting with each other as it were in meat space as much as they used to be. There’s a sense that there’s something about relating to these objects, even if there are people on the other end of them, that somehow distances us from other people. Do you think that that’s something that is happening and that it’s something we need to be aware of? Because all of this technology and this way of relating to things is actually quite new.

Jeff: Yeah, I mean, it definitely is a thing that is happening, and the question is, to me is - is it something that’s bad, or is it an opportunity? And I’m a Catholic, I’ll disclose that here, but both Pope John Paul II, Pope Benedict and even Pope Francis - who are the three most recent leaders of the Catholic Church, they’ve all seen this revolution coming. And it’s interesting because each one had a different perspective on it. But all three first identified it as being something good, and then they identified it as something that presents an opportunity for every individual to kind of - you can use that to increase your relationship with someone, or you can use it to close out your relationships with other people. It’s really up to the individual.

Also, as developers, we make these tools that can bring people together, but I think all three of them also emphasize the point that real human interaction is important. And that’s why all three of them also said - when you have things like the sacraments and the church, where you kind of come together as the church community, it’s important to have a physical presence, because there’s something different between a physical presence with someone else - and something through a screen or through an email or through text, that kind of thing. There’s something metaphysical there that just doesn’t happen. And it brings up some interesting discussion, because it’s definitely, everybody sees it happening today. People sitting at the same dinner table, all of them on the phone, none of them talking to each other. Or even worse, everyone on the phone talking to each other at the dinner table, with their phones instead of their voices. It’s a strange thing, and I think as a society we’re dealing with it and figuring out our best step forward at this point.

Len: When you speak about opportunity and looking at it with some optimism, is there anything in particular that you think of when you think about the opportunities for new forms of interaction that we’re being presented with now, or that we can develop in the near term?

Jeff: Yeah, one thing especially that I see is people who have any kind of mental delays, or physical problems that can interfere with their ability to interact, some of these people already are seeing the benefit of - they have these tools now that are so much cheaper than they used to be, or that they didn’t even exist ten or twenty years ago, to allow them to communicate and be more personable with people. And it’s the same thing with science and drugs and medicine. Coming up with new ways that people can combat situations and illnesses that have made them unable to be part of, like, the human experience, and have real deep human interaction. And again, there’s always two sides to it. If you take somebody’s - what we call an illness, that might also enable them to be somebody different, who they really need to be. You need to make sure that you’re not just muting that part of them; that you’re expanding their abilities to interact and be part of the human race.

Len: That reminds me of one time, actually relatively recently I was watching a research documentary about the history of the computer, that I think had been made in the early 90’s. And it included just an amazing scene that almost brought me to tears actually, in which a bunch of young people are in front of computers - and they’re actually able to read books on their own for the first time, because they were unable to hold them and turn pages. So reading with a paper book was basically an impossibility for them. But now, when they can read on the screen and they could turn pages with voice commands - all of a sudden this whole world of human thought was open to them for the first time in an independent way. And yeah, that just struck me as a really powerful way of sort of using technology to increase people’s ability to interact, not only with other people but with, you know, people from the past and our history.

Jeff: Yeah and a lot of it seems to come from the ability and the desire for - a lot of people have a lot of disdain for the idea of capitalism. But in a sense, some of the reasons why some of these technologies have been opening up people’s lives, especially people who might not be as well off as the top 1%, or whatever, is that since these devices are now in the hands of all consumers and are becoming cheaper and cheaper - devices that have what would be considered supercomputing abilities years ago - we can now write software and put the software in the hands of everybody to do these things and to enable new interactions. Especially for people who - like I said, ten or twenty years ago, they would have to spend $50,000 or more to have a device to let them communicate. Now that’s on your tablet in your pocket. Where you can mount the tablet to a new kind of mobile platform that you can use, if you have a physical debility - to get in places you never could before.

On one side, we see people sitting with their phones and blocking themselves out from other people. And on the other side, we see people with these phones that are opening up a whole new world. And being able to converse online and converse in person even, with other people.

Len: Just circling back to your book. You mentioned that it started out as a blog, and eventually you decided to turn it into a book. Was there any sort of particular moment? Like did someone ask you, “This would be great if you wrote a book about this” or “Can you expand on this because it’s really helping me do my work”?

Jeff: It was for me mostly a personal goal. I actually have been blogging regularly since about 2004. And probably around 2008 or 2009, I started thinking, “I really want to write a book someday. I have no idea what I want to write it about. But I want it to be something I’m passionate about and I’m interested in, and I feel like I could contribute something to people”. And for a long time I’ve done a lot of technical documentation. Like I said, I used to work with the local radio stations. One of the projects I always would get texts with is, “We have this new phone system, or we have this new whatever. Go sit down, sit through all the tutorials, and then write up a guide that will help people to quickly get up to speed on it”. Because the manuals you get with the manufacturer are pretty much junk.

So I’d spent a lot of time doing technical writing and documentation. And I’ve spent a lot of time blogging. Early on, it was more about personal things and religion, and philosophy, and those kind of things. But I started writing a little more about computing, and when I got into Drupal, I started doing more tutorial type posts on, “Here’s how you do this and that”, documenting how to do certain things in Drupal that I didn’t find were well documented. But there’s one platform for documentation and then there’s another platform for guiding people, really. And I’ve seen books are usually the best way, at least for me, but also for a lot of other developers to get into a technology.

So I think after I wrote four or five, six hundred to a thousand word blog posts on Ansible, I realized, “I can keep doing these short posts that kind of are disjointed, and don’t really guide somebody through things. But they give somebody a few nuggets to kind of get started with.” And instead of continuing to do that, I wanted to write more of a comprehensive guide of, “You’re a developer who might know a little bit of shell scripting and how to turn a web server on in a cloud environment”. I wanted to take that person and bring them through to, “Hey, it’s not that hard to build an entire infrastructure with fifty servers in Amazon or in Digital Ocean or something like that”.

So I figured the best way to that was a book and so I took those blog posts, kind of wrote a little introductory part to it, reorganized them. And that was the first published edition. Which at that moment, I said it was 30% of the book’s completion, when I first published it on Leanpub. Now, little did I know that after those, like, 30 pages were published, I’d be writing another 370.

Len: How did you find out about Leanpub and why did you decide to use us?

Jeff: I’ve been on Hacker News for a while, and I kept seeing every now and then somebody would post, “Hey, I have this new book and it’s on Leanpub” and I’m like, “That’s interesting, I’ve never heard of this Leanpub thing”. And a couple of them, I think it was actually right around the time where Node.js was getting popular. The Node - I forget was it the Node Craftsman book or The Node, one of the node books on there–

Len: Yeah, Manuel Kiessling, I think?

Jeff: Yes. Yeah, it’s one of the more popular books on Leanpub. I bought it on Leanpub and I’m like, “This is amazing. Like I bought the book, it wasn’t finished, but it’s already really high quality - and I get the free updates forever, and there’s no DRM. Like where’s the catch?” So it was really from a consumer perspective.

As a technical person I hate the idea of DRM on a book. Because it’s like, when I go to a bookstore and buy a book, I don’t have like a locking mechanism that I have to unlock to read it. And so I liked that aspect, and I liked the whole user experience of buying the book and getting updates, the author could communicate with me. So it really attracted me to the platform.

But that was probably six months to a year before I decided to start writing. And when I started writing I looked into the options and it was basically - Leanpub was awesome and everything else was like ancient history. And nowadays there’s other, there’s like Gitbook and some other platforms you could write with, but Leanpub is still, from what I’ve seen, it’s still the most like actual publishing workflow friendly tool out there. And I’m glad I’ve been sticking with it because it’s - right now I’m working on actually publishing a printed copy of the book and the whole process was basically, scroll through those couple of things, click a button, and you have the PDF, and you’re done, instead of having to reflow things and lay it out manually and all that kind of junk.

Len: Yeah, thanks very much for that. Yeah, we worked hard with a few of our early adopter authors to build our print-ready output features. We have one for PDF, and we have one for InDesign as well, which is a little less mature. But yeah, that’s a really important part of us. What we’re doing is that we want people, when they’re done their book, to be able to hit a button and then have something ready to put up on CreateSpace which I think you’re using–

Jeff: Yeah.

Len: Or Lulu or something like that, so that then they can do print. I have a question about that. Why are you making a print book?

Jeff: One thing that I’ve realized, for this book in particular, it’s more of a guide for somebody who’s never seen Ansible before. They can pick it up and by the end of it, they’ll be hopefully able to make their entire infrastructure and do everything automated - so they’re never logging into servers again. For that kind of a guide, I’ve had a lot of emails from people asking, “So when can I get a printed copy?” because they want to sit there and mark it up, they want to dog ear some pages and have it front of them while they’re doing their work. And that workflow is what a lot of people like for more of a guidebook.

If it’s more of a novel, where it’s a story about the software you’re using, or if it is actually a novel, a lot of people are more prone, I think, to get the ebook version. But there are some developers who like to mark their book up and like to have that physical interface a book has, that so far no kind of e-reader can give.

The other reason also is - I got started in web development through design, and so I’m a little bit more designer-oriented than developer-oriented, even though I don’t do as much nowadays. So I really wanted to get a physical copy, just so I could have it in my hands. It’s kind of like a physical reminder.

I actually just got a proof. The proof had some problems in it so I’m going to get another one. But I got a proof, and it was so amazing to know that two years of time that went into this book is in my hands. It’s like a tangible - it goes back a little bit in our conversation - it’s like when you have it in your hands, it’s different than having a file. You can flip through the pages that you spend so much time working on.

And the coolest thing is, with the feedback that I can get through Leanpub, it only takes a couple of minutes to build a new copy. So I can keep working on that physical printed book almost at the same rate that I can work on the online editions and the ebooks through Leanpub and CreateSpace. It’s a lot better I think even now than it was a couple of years ago when I started the book. I looked at the workflow back then and it would have been a couple of days’ worth of work just to do each new iteration, but now it takes less than a day to take something you wrote in a Markdown file or LaTeX, and then get a proof to your doorstep. It’s pretty cool.

Len: So were you interacting a lot with readers while you were writing the book?

Jeff: Yes, that was the other thing that really got me into the book, and turned it from 30 pages to 400 pages. When I started the book, I put up a little page that said, “I’m starting writing on this, sign up here if you’re interested”. And I think I got like 40 or 50 people’s email addresses. And that was already getting close to my goal. My goal was to sell 200 copies of the book. If I did that I think I would have been pretty happy. It would’ve been fun - write like 80 or 90 pages, be finished with it. But I got 50 then, and then when I published the first version - which only had like 30 or 40 pages and only a couple of introductory chapters - all of a sudden there were a couple of hundred sales. And as I’ve already sold the quota that I set for myself, and I haven’t even started the book barely. So that really motivated me to start writing more and giving a little more structure to the book.

Once I did that, I started getting a lot of readers who were taking my examples and putting them into situations I never would have thought of, and being like, “This broke. This broke. This broke”. So really they were being my QA and reviewers early on. And I have - I even put a list of the people who helped make the book better in the afterword. If you get the print copy, it’ll be in there. And it’s actually up, I just updated it last night with that. But those people are awesome. They, a few of them even sent me 10 or 20 emails throughout the writing of the book. Every time I’d put out a new chapter, they would sit through and find like every little detail, when I would have a grammatical error or whatever. And it was awesome, because that made my editorial process be a lot more of optimization rather than fixing my stupid grammar.

Len: That’s fantastic. I noticed you also include in your book a changelog, which I imagine won’t be in the print version. In your change log, with each new version you document what the sort of major changes were that you made and improvements in editions. I was wondering if that was something that you think necessarily belongs in the book itself, or if Leanpub could provide a feature like that, would you prefer to have that over a changelog that you manually create in the book itself?

Jeff: I can go either way. The thing that I liked about having it in the book itself, was that somebody didn’t have to refer somewhere else when they wanted to see what was new. It was also a good kind of barometer for the readers to see what’s been going on - or has anything been going on? Because there were a couple of points where I had some dry periods, and I didn’t write anything for a month. And some readers would go on there and they’d see - if they didn’t have a changelog, they wouldn’t know like, “Is this just abandoned, or what?”

I don’t know what the statistics are on your end, but I know for myself, if I start a book and there’s not a lot of interest, I might not ever finish it. But somebody who buys the book might not know that. So I wanted to give them that idea of, “This book is still active, and I’m still working on it.” And there’s an indicator on the page that says the last time it’s been updated. But I also like giving a tangible guide for, “Here’s what’s been updated.”

So if it were integrated into Leanpub itself, that might be nice. I’d just want to make sure that there’s a way that that can be updated easily. Because it’s really just for the reader to see, “Here’s what’s changed. Here’s what you might be interested in,” and sometimes the readers - like I said - there’s dedicated readers - would even go in the changelog, and they’d be proofreading my changes for me. I don’t know what drives them to do that, but they’re awesome people.

Len: That’s amazing. I hadn’t quite thought of that use of a changelog within a book before, that even if there’s been a dry spell, it gives you a very confident sense that this book is being worked on, and how it’s being worked on. That the person’s being rigorous about it.

One idea we did have for what we call our “library”, which is where your Leanpub books are kept - which we now see either in the browser or our iOS app, which is still a baby - it’s an interesting idea, like “What does a library of in-progress books look like?” We were thinking one interesting feature might be if you click on a book and kind of opened it up, that you would see a timeline. So it might be a line, and then there might be little circles along the line, that would indicate when the author had made a major improvement, or something they thought was significant enough to surface in a timeline, and then click on it or something and see basically, yeah, what those changes were. So that was what we were thinking, something along those lines. But I take your point about how important it would be to actually have something like that in the book itself. So that’s something that we’ll definitely think about.

Jeff: Even as motivation to me as an author, I know one reason I thought about going with a traditional publisher was just the forced pressure of - you have this deadline, you have to get the first draft in by here and that kind of stuff. Without those forced deadlines, you aren’t really motivated sometimes to get through the hard parts. There are some chapters in the book where I’m writing it more because people need to know about it, not because I love it. And reading through the book, you might see a couple of those kind of sections.

But having some sort of metric to show me too, “Here’s where I think I’m at and here’s where I’m going.” That’s pretty helpful. So I’ve even built my own little bash script that will count the words I’ve written in a given period, and give me a nice little graph of it. So I can see, I run it every month or so, and I just make sure that I haven’t just dropped off completely in terms of how much I’m writing.

As a writer, you have to motivate yourself to write something. Even if it’s horrible and you’re going to throw it all out, if you’re writing something your brain keeps going, and you keep moving forward instead of just stopping. And I know that from writing all the big blog posts I’ve done, and all the articles I’ve written. Even if it’s only a 500 word article, you can get stuck and then you just give it up. But if you just keep writing - I think there was a blog post I did a couple of weeks ago. I wrote it, four times I think in full, and deleted it each time saying, “This is just terrible.” And then finally it’s like, “Ah, there were go. I have it. I feel that that’s the right way.”

Len: Well, it’s a fantastic post and obviously we noticed it right away. And yeah, when it comes to motivation, I was just describing it to some of our developers, the post - and one of the things I really liked about it was - you talk about how successful your book has been, but you also talk about how much work went into it. I think you said something like 1000 hours? Is that right?

Jeff: Yeah, it’s close to that. Early on I was very strict about tracking the hours. Now I’ve kind of dropped off, and now it’s like one evening I’ll spend four hours on it, and then the next night I spend zero time. So there’s still five to ten hours a week at this point, as I’m trying to get the book on Amazon and iBooks and paperback and all that kind of stuff.

Len: Did those hours, did you include - I forget, perhaps you did mention this in the post - did that include time you spent marketing the book? Did you spend any time marketing the book?

Jeff: Yes, and I’ve actually spent pretty minimal time so far marketing the book. That’s one thing where some developers can - I’ll call it “pimp themselves out”. And I can’t do that as much. It’s hard for me to do it, but I force myself to do it. Because if you don’t do it all, you’re not going to get any sales. So I’ve probably spent maybe 2-3% of my time on the book doing marketing - either talking with a couple of different organizations, trying to get them to promote the book internally, and working with a few groups that are doing similar, doing related Ansible projects, trying to get them to cross-promote the book a little bit.

But the main thing for me in terms of marketing has just been having a Twitter feed just for the book. And I had that early on, I think the first week I was writing the book, I created it. And that’s up to at least 500 or 600 followers. And that’s been a good platform for getting people to retweet information about the book and getting reposts.

But really the number thing has been that email list. Early on I had 50 or so people subscribed, and as the book has gone on and more people buy it on Leanpub - every time I do anything through email, I get an immediate small spike in sales. It might be one to two sales per day for a while, and then I’ll do an email and it goes up to five to ten for a few days. And so it seems like, at least for things like books, reminding people, “Hey, this book is out here, and here’s a coupon for half off for your friends,” or something like that - those are the things that get the most in terms of tangible spikes in sales.

The other thing is getting closer to finish. I think a lot of people are less comfortable buying before the book was 70 or 80% finished. But once I reached some point, the sales started going up a little bit, to the point where it was more steady over time. There weren’t little spikes here and there from the emails. It was more steady with a small spike.

Len: Okay. I’m curious - if you were approached by a conventional publisher who wanted to buy the rights for Ansible for DevOps - is that something you would consider doing?

Jeff: It’s something that I would consider depending on what they were talking about. One of the best advantages of having the book through Leanpub - and especially Leanpub, because it’s really the only platform that’s like this - is, Leanpub is more about getting the book to the readers, and it’s not about making money for Leanpub. At least that’s - every organization that sells something, you have to make some money. And I get that, but Leanpub has the least restrictive licensing terms, the least restrictive operating agreement with authors, out of any place that I’ve seen short of just posting the book on Github. And so that’s really what attracted me there, and the fees are nominal basically, and the capability to take your book and go to CreateSpace without having to do any extra work. That alone is worth whatever fees that I’m paying, which is again pretty nominal for this book.

Len: Just to be clear to anyone listening. We pay a royalty rate of 90% minus 50 cents for every sale, so it’s not exactly - we don’t, what I’m trying to make clear is that we don’t actually charge authors fees. What we do is we take a cut of sales, if they get any.

Jeff: Yeah.

Len: And so that’s 10% minus 50 cents per sale. [Editor’s note: the fee is 10% plus 50 cents per paid sale, which includes the transaction fees we are charged from PayPal. There is no fee for free sales.]

Jeff: Another cool thing about the platform is Leanpub seems to have a little more uptake with a technical audience. And so a lot of books on Leanpub are good opportunities to work together with other authors. I have a few bundles that my book is in, and those bundles have also helped to produce extra sales. So it’s cool, because sometimes a bundle - like somebody with another book in the bundle will promote their book, and then I’ll get a spike in my sales because people are, “Oh, that’s a cool book,” but I don’t care about this one. So it’s neat to have that. It’s kind of an informal community of authors at Leanpub.

Len: Oh, that’s awesome. I’m so glad to hear that. Yeah, our work on community is something we really want to focus on in the future. And yeah, we’ve got a feature where if you’re a Leanpub author you can reach out to another Leanpub author and ask them to make a bundle with your book, and they can accept or decline. That way you can have people make connections with each other - especially if they share interests or specialties, and then they can kind of cross-promote. And it can be a really fun thing to do.

I guess my last question for you is is there anything that stands out with your experience with Leanpub that we could improve? Is there anything that isn’t there that you think should be there? Or something that’s there that hasn’t been done the right way? Or another way of putting it is - If you could have your ideal “Leanpub give me this one thing”, what would that be?

Jeff: I think one thing that would make things a little simpler for me is the ability to more quickly preview changes, especially to the full book. If there was some local tool that could produce a PDF copy, so I could have a continuous integration process for my own book, that would be cool. I wouldn’t expect that, because that’s the bread and butter pipeline that probably takes the most work to maintain on Leanpub.

But that being said, the other thing that’s been tough - and the reason why I asked for that is, sometimes, when I’m writing in Markdown, which is my preferred format for writing, sometimes the way that the syntax behaves can be a little surprising. And even when I look at the Leanpub manual, there are some times where the examples don’t exactly match up to what I’m trying to do. Right now I think the Leanpub manual has a formatting that’s a little funky if you look at it in the front end, in the browser. So things like, when you put code blocks in lists with a certain language, with text surrounding it, with multiple indentations in that list - then those kind of things are where you find these little edge cases. And it just takes my brain a little bit out of the writing when I’m trying to work on the syntax stuff. But the ability to quickly preview those things, and maybe even have like a tool that can show you, “Here’s how it’s gonna look.” You can like paste a sample in, that kind of thing would be cool. But the thing that I–

Len: Oh, that’s very interesting. Yeah, thanks for that suggestion.

Jeff: Yeah, the thing that I like most about - in the time that I’ve been writing this, Leanpub’s interface has improved, at least three times, in a major way, to the point where it looks so fresh, the author dashboard is a lot easier to navigate, and has more useful information on the front of it now. When I started it, a lot of times I would go in there to change something, and I would sit there and I would click through every single menu, because there was no organization to it. So now it’s a lot easier to find, “Oh, it’s under ‘Writing’, and then this section.” So that’s been really helpful.

Len: Thanks very much for that. That’s really great feedback. The explanation for - there’s sort of a two-part explanation to why Leanpub was that way, and why it’s been improving. The first explanation is we’re a bootstrapped startup, so Leanpub is our baby that we would love to be spending 110% of our time on, and hopefully we will be in the future. The second explanation is we really believe very deeply in customer development. And so often, adding a feature and making it work for an author who’s desperately in need of it, is more important than necessarily optimizing the design or organization of things. But as we’ve grown more mature, we’ve been able to then focus. When things become more stable, we’ve been able to focus more on organizing things properly, and presenting them well. So I’m glad to hear that the work we’ve been doing on that has actually been an improvement. Because when you’re sitting on this side of things, you’re often just - you just hate yourself because things aren’t perfect. So it’s nice to hear that.

Jeff: Yeah, it’s been much better.

Len: Okay, I just wanted to say, thank you very much for being on the Leanpub Publishing podcast. This was a great discussion, and thanks for being a Leanpub author.

Jeff: Yeah, thank you very much.

This interview has been edited for conciseness and clarity.

Leanpub Podcast Interview #24: Obie Fernandez

by Len Epp

published Jan 06, 2016

Obie Fernandez is an author, consultant, traveler and photographer. Currently the Senior Vice President of Engineering at 2U, Obie is the bestselling author of Ruby on Rails books, and he has been involved in a number of successful startups and other projects. He recently launched his latest book, Serverless: Patterns of Modern Application Design Using Microservices (Amazon Web Services Edition), on Leanpub. In this interview, Leanpub co-founder Len Epp talks with Obie about his career, his books, and the inspiration behind Serverless.

This interview was recorded on December 28, 2015.

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

The audio for this podcast has some blips in it and you’ll see these reflected in the occasional “…” in the transcription.

Obie Fernandez

Len Epp: Hi, I’m Len Epp from Leanpub, and in this Leanpub podcast, I’ll be interviewing Obie Fernandez. Obie is a New York City and Atlanta, Georgia-based author, consultant, traveler and photographer. He has been involved in professional software development and consulting for over 20 years, and most recently he’s been involved in the startup world with a variety of projects. Obie is currently Senior Vice President of Engineering at 2U, a New York City-based platform for delivering quality online degree programs. Obie is a serial entrepreneur, and in the past he has been the CTO and co-founder of a number of companies, including Andela and Lean Startup Machine. He’s also Series Editor for Addison-Wesley’s professional Ruby series and an avid EDM DJ.

Obie is probably most famous as the bestselling author of Ruby on Rails books. He’s also the author of a number of books that have been published in various states of completion on Leanpub, including The Rails 4 Way, The Lean Enterprise, and How to Eat Nachos and Influence People. He’s also currently working on a new book called Serverless. Patterns of Modern Application Design Using Amazon Web Services, which will be launching very soon, and which we’ll be talking about later in the interview.

In this interview, we’re going to talk about Obie’s professional interests, his books, his experiences using Leanpub, and ways we can improve Leanpub for him and other authors. So, thank you Obie for being on the Leanpub podcast.

Obie Fernandez: Thank you Len.

Len: I usually like to start these interviews by asking people for their origin story. I was wondering if you could tell us how you first became interested in software development, writing, and eventually in consulting in startups?

Obie: Sure. Well, I think I’ve been really lucky, like a lot of technologists of my generation. I’m 41, almost 42, and grew up in an era where it was cool to tinker with electronics and take things apart. At school, we got taught programming as early as third grade. So I was working on an Apple 2E and learned BASIC and learned Logo, and I think that that’s a real advantage, because the concepts of programming at such a young age, it just - I think has an amazing effect. Because - I don’t know, it just feels like I can’t even remember when I started programming, right? It’s like something that’s been with me for a long time.

I did eventually start getting into commercial software development with my friend Nate. He is my same age, he’s been my best friend my whole life. He started a TV and VCR repair business at a young age - always entrepreneurial - and he had a storefront selling beepers, which were like the pager things that people wore on their belts and whatnot which are not really used anymore, but at the time they were all the rage. Being responsible for the billing, and since we were both kind of hackers and whatnot, we wrote a software package that ran on his PC and used his modem to page his customers when it was time for them to pay their bill. They’d call back and they’d hit a message that said that their account was due and whatnot. We expanded that into kind of an account management system for beepers, called Beeper Pro. Unfortunately never went anywhere. We could have been like software magnates of the beeper world, or whatever.

But the little startup that we put together with a friend of his kind of leveraged that. It didn’t pan out, mostly because I think we didn’t have the attention for it. We ended up doing some early web hosting, and I learned some Smalltalk and I learned Java. We got involved in a whole bunch of other things. I was DJ’ing at the time, so I was having friends from New York come over and record sets for me to stream in 22K WAVs at A lot of interesting little projects.

Eventually, I was able to get a job at a professional business. This was back in 1995. I claimed expertise with Java, which I’ll admit now was a little more fake than the interviewer [would have gathered]. But I had basically read, Java in 21 Days, which had just come out, or something like that. I think it was my first lucky break. It was a professional job doing programming when I didn’t have a computer science degree and I didn’t really have any sort of formal credentials to get a job doing so. But I was able to turn that into a series of jobs in professional consulting and over the years have had a number of lucky breaks which - together with hard work, got me to where I am today.

Consulting in general, I think is a great place if you really want to keep your skills from stagnating. Especially if you’re good and ambitious. I did a lot of consulting, then I was at a startup for 4 years in the early 2000’s, that was good, because I rode out the dotcom bust, the original dotcom bust. And then I ended up at ThoughtWorks. ThoughtWorks, during the early to mid-2000’s was the place to be. I got to work with Martin Fowler, Neal Ford and a bunch of other notable people - Fred George, who has influenced me a lot on microservices. It’s amazing what you can do.

Actually one of the common themes throughout, especially since the early 2000’s, has been kind of constant self-promotion and blogging and that sort of thing. Maybe it’s common with some of the other Leanpub authors. But in the things that I point to when I’m coaching people or advising my friends. Like, “Hey, if you really want to get ahead, pay attention to the way that you present yourself. Pay attention to the way that you credentialize yourself online. And I’ve done that. I’ve had a blog since the early 2000’s. First I was talking about Java.

I had some, a little bit of notoriety in open source Java. I worked on some dependency injection framework stuff in open source. That was kind of my first real dip into open source. And it just set me up to be in a position to talk about Ruby on Rails in a significant way in 2005, and I was one of the loudmouths that was saying, “Hey, this gives 10x productivity gains over Java. Java sucks.” and all this stuff, and being really controversial and brash and attracting attention.

That got me my first book deal with Addison-Wesley, to write, The Rails Way. Later on that led to getting the series editorship, and then being involved in all the other great books in that series. So it all points back to always being active about wanting to share the knowledge that I’ve got. Wanting to credentialize, wanting to blog, wanting to write. I mean, the first book was mostly due to something that a lot of us had or have, which is, “I’d like to write a book someday. It’d be nice to see my name on the cover of a book.” And then afterwards it turned into like, “Wow this can be a really important fuel for building your career. Because the more that you credentialize, the more that people view you as an authority, and the easier it is to get the kinds of jobs that you want, To work with the kind of people that you want. To attract other people who are also very talented and ambitious and going places.

Len: That’s a really great story. Especially the way you emphasize your own activity when it comes to gaining notoriety and getting attention. I was wondering, did Addison-Wesley approach you, or did you approach them with the idea for your first book?

Obie: Deborah approached Curt Hibbs who was an early figure in the Ruby blogging community, and who I think wrote some of the early … that were popular. He worked at Boeing and I haven’t heard from him in years, I hope he’s okay. But Deborah Willings is an editor at Addison-Wesley, who I adore. I owe her a lot. She approached him, and then he recommended me, because he just knew me from my blog. So she walked up to me and just cold-presented me with an offer to get involved in writing a book at a conference in San Diego.

Len: I’m curious, it’s something you mentioned about starting to learn programming when you were in grade three. I think this is something we’ll probably return to later, because I know that education is something that’s been an important part of many of the projects that you’ve been involved in. I’m wondering, I think there are probably people listening who wish they’d had the opportunity to start learning programming at school at grade three. Were you at a special kind of school in some way, or was it just a kind of unique circumstance?

Obie: I don’t think it was that unique for its era. I mean it was elementary school in New Jersey in Hackensack, which is the county seat of Bergen County, which is a somewhat well-to-do county - I guess. I mean, I didn’t grow up in a well to do area, I was in a working class neighborhood and working class parents. I once saw that, that particular era, there was a population dip. I guess it was kind of like an after-the-boomers sort of thing. The schools were relatively well funded in relation to the amount [of students], because the population dips, which kind of gives you a little bit of insight into how macro trends kind of play out in people’s lives. It’s kind of amazing to think about.

Len: Yeah, yeah, that’s really interesting. One of the companies you’ve been involved with is Andela - am I pronouncing that correctly?

Obie: Yeah, Andela.

Len: Yeah, Andela. I was looking at it, and on its website it says it “integrates full time genius level remote software developers into your team”. And I remember, I read a little bit about your involvement. It says it works with Fortune 500 companies to find untapped talent from around the world. I was wondering if you could explain a little bit about what your contribution was to the company when you got there? Beause I read that you sort of changed things a little bit.

Obie: For sure, happily. I joined very early on as CTO, and brought kind of that real-world experience in running a consultancy. The business model is to find very, very intelligent - I don’t know about genius level, but certainly top five to ten percentile in terms of problem solving capability, in Africa. So we operate in Kenya and Nigeria. I’m still involved as an adviser, I’m very close to the CEO Jeremy Johnson. What we did there was to find a way to put some of these young Nigerians, and now Kenyans to work, giving them opportunities that they clearly do not have on their own. It’s very hard without access to stable power, stable internet.

And then I think, one of my significant contributions there that I’m most proud of is that we realized early on that it was wasn’t just the structure concerns, right? It’s not just safety and electricity and internet. Once you have the access it’s easy to figure out the technology on your own, there’s so much wealth of information online that you can get. I mean it’s a dirty word to authors and media in general, but I mean, with piracy and whatever, where I can get a complete library of pretty much any classic book that you want to get in the field - it might be an outdated version or what not, but the access is there if you have the internet.

What you don’t have, and this is what I started figuring out about six months in, in a very vivid way, is a lot of “common sense”, what we would consider common sense - about business environment, how to deal with Western clients. What expectations are around creativity and problem solving? What kind of push back you can give if someone’s telling you to do something that you think is not the right thing? Or if you are not capable of doing what they’re asking you to do.

So that changed my whole pedagogical approach. I pretty much flipped it on it’s head, where we were putting a lot of emphasis on basic technology training and basic computer science concepts in the beginning. I started realizing now we need to really put a lot of emphasis on “soft skills” - communication skills, how to build trust, how to keep trust. How to learn, how to function on a team. How to apply creative problem solving. How to trust your own intellect when it’s appropriate, or lean on others. That sort of thing.

The mechanism for doing so was a very, very heavy curriculum of improv training, actually. A lot of people are familiar with comedic improv - the show, Whose Line Is It Anyway? with Drew Carey was very popular in the United States, and whatnot. What less people know about is a field called applied improv - implied, applied improvisation probably has a couple of thousand practitioners around the world. Consultants who come, a lot of times from the comedic improv background, but they do business consulting, and they go to companies and they do these improv kinds of activities, improv games. Some are very basic, but the idea is to get people to open up, come out of their shells.

In Nigeria, that was especially important, because the young people, and in particular young women, are just kind of culturally trained to be very quiet and shy, especially around any sort of authority figure or anyone that they look up to. It’s very hard to get them to come out of their shell. So we did a lot of work - five to six hours a day for 30 days, a program called “Month One”, where we went over, everything starting with the basic “yes, and” principle of improv. Which is that you - being constructive. So finding a way to build on what someone else is adding, trusting their intentions and then finding a way to build on the tearing down. All the way through these opening up exercises that I’m talking about, all the way towards things that we kind of learn naturally here in the States, even around some tough topics like sexual harassment and what’s appropriate and what’s not, things like that. And just basically not taking anything for granted.

The results have been remarkable. I think that the - our Andelan consultants that are now remote team members to about 50 companies here in the States and in Europe, they fit in very naturally. The way that other remote team members would fit in. It’s not the experience that people may be used to with working with offshore teams.

Len: And how does Andela find people?

Obie: Actually, the population dynamics are such that it’s not hard to find people. They have less than a 1% acceptance rate. So it’s just the combination of social marketing and whatnot. And now there’s a lot of word of mouth, because the opportunity is so awesome. You don’t have to have any sort of formal education in computing. You don’t have to have any particular family connections. You don’t have to have money. You don’t have to have anything. If you pass a battery of tests, then there’s an interview process. That knocks the pool down significantly. And then those people are invited to come to one of our facilities and do a two week workshop, where they get very intensive and fast-paced training in JavaScript or Ruby or now Python.

The idea there is not so much training, as to see what their grit and determination is. Because you push them really, really hard, and the vast majority of them don’t have real programming experience that they’re bringing to the table. So you push them really hard, and then you see who comes out the end. So out of a class of 20 in the boot camp, we may hire five to ten. But at that point, we give you a four-year contract. And you have a job paying a middle-class salary. You get subsidized food, subsidized housing. A lot of them get to live on our campus. The audacious goal is within ten years to train 100,000 of these young Africans and inject them into the global workforce. If we achieve that, or even a fraction of that, it would make a pretty big social impact in Africa. So it’s really one of those startup situations that was very exciting and rewarding, personally, not just in a monetary sense, but also in terms of purpose, that’s what we’re doing.

Len: That’s fantastic, I didn’t know that the goals were so ambitious and positive. That’s great. And that leads me to ask you about 2U where you’re Senior Vice President of Engineering now. I was wondering if you could tell me a little bit about what 2U is doing, and what your role is there?

Obie: Yeah sure. So, as I was starting to get kind of exhausted with the travel and the intensity of working with Andela, I needed to take a little bit of a break. And I got married, I moved to New York from Atlanta. I had a bunch of life changes. My daughter Taylor went to college. So 2U is kind of a sister company to Andela, a lot of the same early investors. The CEO, Jeremy Johnson, was one of the founders of 2U. So the CTO of 2U made me an offer I couldn’t refuse. To come, help, really take their engineering department to the next level over there.

2U’s a successful startup. It’s a successful New York startup story. IPO’d I think about 18 months ago. So about 8 years old. Lots of market traction, a lot of credibility. A lot of really good brands associated with us - Yale, NYU, UNC. We have a good thing going on. We have a platform, along with the services that we provide to these schools so that they can get their graduate programs online. And what’s amazing about what’s happening there, is that … of graduate education. The best graduate program is one that has some real world experience, that one has gone out and gotten some maturity and … their career and their life to the next level.

But at that point, a lot of them have lives already. They have budding careers, or maybe established careers for a lot of the executives and professionals. They may have kids. They may not be able to move and do school full time in a particular geographic region. So what we give them is the ability to just work on it from home, remotely - while still getting the full experience, in a lot of cases, with better outcomes that they would get in person, on campus.

We now have programs that have been going on for over five years, and we can start to track the outcomes, and we see people actually having better outcomes. So the challenge there for me personally, what keeps it interesting is that it is a startup that went big and has done well. And we now have a technology department with over 100 people. The vast majority of whom are really great, really talented, really energetic. And then it’s just a question, how do you harness that talent to take us to the next level? We have a certain amount of partnership programs now, but how do we increase that by multiples?

And that - scaling technology is always kind of a fun challenge. And for me, coming back to an environment where there’s bigger teams, there’s bigger coordination and orchestration of effort, where there’s more room for applying enterprise technology or if you’re looking at the big picture, looking at strategy around it - that kind of takes me back to my days at ThoughtWorks, working with bigger Fortune 100 companies and CIO’s offices and CTOs, doing some pretty interesting large scale work.

So, it’s been amazing. I wouldn’t have necessarily predicted that it’s something that I would have been super interested in. Like especially like, let’s say five, six years ago when I was running around and doing mostly kind of smaller start up stuff. But life is more interesting when you move to different kind of areas of interest, of pursuit. And in this case, these larger scale systems are starting to become really, really interesting to me.

Len: Before I move on, asking you about some of your book projects, I’d just like to go back a little bit to what you were saying about piracy. You know that at Leanpub we’re very - we have strong opinions about things like DRM, Digital Rights Management.

Obie: Yeah.

Len: Around ebooks. And I was just wondering if you could - because I have no idea, but what’s your opinion about DRM and ebooks?

Obie: I think that one of the beautiful things about Leanpub is that it makes it real easy to get the material into people’s hands. And if the author wants to put it at an affordable price point, that puts it into even more people’s hands. But having firsthand experience with developing markets, it’s not the fact that a young person in Nigeria can go to one of these piracy websites and download the latest book on JavaScript or whatever - that’s not taking money out of the author’s hands. Because they don’t have the money to pay for it anyway. And there’s no one to pay for it for them.

So in terms of just kind of the bigger picture of global equality - I mean, the fact that a lot of people - I mean there’s not - you don’t necessarily have to go to Africa to see this, you know. I know that a lot of us, when we were younger, pirated things like Photoshop. Because it was too frickin’ expensive to actually pay for it… But you know what? Now, if you use it, you pay for it. It sure helps that they created a subscription model, where you can pay ten bucks a month or something like that.

I’m generally not a fan of DRM at all. I was involved in the hacking scene, BBSs and things like that early on. So I come from a hacker background. Never really been that super concerned about it. Because the market is out there. I went with a traditional publisher with Addison-Wesley, because it was just the thing that you did. And then I continued going with traditional publishers after that; Lean Enterprise is on Wiley. There’s a big professional market out there that pays for it. Safari’s great, subscription income from Safari’s great. Stuff like that. If you’re trying to credentialize, if you’re trying to get started, it’s great to go with traditional publishers. They’ll do whatever they’re going to do. I default to getting the material in people’s hands, helping them out and basically looking at it as, if people are not paying for your material, it’s probably because they can’t afford to pay for it. Or they’re just checking it out, and you’ll get it back to you somehow later.

Len: Yeah, that’s great. I mean, that’s very - I’ve got to say, that’s very consistent with our experience as well. Especially over the last year, where some of our most successful books have been by people who are providing courses online, in particular through Coursera actually. And for them, the variable pricing that you can do on Leanpub was a necessary condition, because they had a lot of students who couldn’t necessarily afford to pay for books, and they did not want to exclude them from participating. But they also had a lot of people who wanted to pay. And so, allowing the reader the choice to pay when and whether they can or not, was really crucial. That seems to be an interesting thing that people are kind of coming to terms with, with the globalized marketplace that the internet offers, and especially in education.

Obie: I think it’s a really smart move, and I can tell the listeners from experience with variable pricing. Just because you set something at a low price, doesn’t mean that people won’t pay the higher price.

Len: Moving onto your books, some of your books on Leanpub have had interesting histories, and in some ways, they’re the ideal Leanpub books. I’d like to ask you first about, The Lean Enterprise: How Corporations Can Innovate Like Startups. First, I’d just like to ask you what the book’s about and why you chose to write it?

Obie: Yeah, so my partner, Trevor Owens and I - we have a company called Javelin. I’m not actively involved with it anymore, but before that it was called The Lean Startup Machine. Tens of thousands of people did the Lean Startup Machine experience over the weekend, over the course of the last five years, and have gotten a taste of what lean startup is about. Eric Ries of course wrote the best-selling book, The Lean Startup. If you look at the way that he launches his books - everyone has a lot to learn. All of us have a lot to learn about that sort of thing, he’s certainly one of the biggest success stories for doing that sort of thing specifically with books. Seriously, look at his latest book.

We started a whole business on applying lean startup and helping entrepreneurs and want-to-be entrepreneurs to figure out how to not waste their hard-earned savings and years of their life pursuing ideas that didn’t make sense. And then over the course of the years of doing that and getting involved in building some enterprise software around it, like basically trying to set up the go-to kind of web application for running your lean startup experiments, we talked to a lot of corporations like Nordstrom, GE, etc. that do lean startup at a large scale. And we started learning a lot about how to apply lean startup. One thing led to another, and we pitched this book idea to Wiley to basically talk about how to apply lean startup, with the target audience being senior management and the C-suite. Basically, how to establish what we call “innovation colonies”, essentially taking the experience that you would get at like, let’s say a Techstars accelerator - but doing it within the context of a corporation.

So it’s a very business-heavy topic. It’s not for the average consumer or the average technology programmers, they’re not necessarily going to get a lot out of that book, other than, maybe, things that they can pass along up the chain? But we do see it as our contribution to trying to create friendlier environments in corporations for innovation and for entrepreneurship in general.

Len: On that note, how does one get around the bureaucracy in large companies where it is not necessarily explicitly, but sort of systemically hostile to lean startup philosophies? I mean, I know Nordstrom, for example, is just fantastic. I’ve had some experience with people from Nordstrom, and they’re just great about innovating and looking for new things. But we’ve all had encounters with companies that aren’t like that. And so how does one - for example if I were say in the C-suite in a company that had a foot-dragging bureaucracy, how would I go about introducing lean startup technology?

Obie: It really has to be introduced. I mean you can do it - so there’s two answers to that. You can apply lean startup as a product manager or as a general manager. Someone who’s responsible for describing the parameters of success, the more objective that you get, the more that you rely on, build-measure-learn cycles within your business - that’s how you introduce it at the grassroots. And that’s generally successful. That’s generally viewed as a good thing, and it’s something that managers and middle executives can play up as doing things the right way, let’s say. And it can have concrete business benefits.

As far as doing an end run around bureaucracy, I mean that really has to come from the C-suite executive level. The bigger corporations are all tuned into it to some degree or another. I have a friend named Alan who’s the CTO at Coca Cola. He’s been heavily, heavily involved in innovation kind of activities. And you’ve got to realize, these sorts of things take different forms. Sometimes it’s kind of - it’s skunkworks, sometimes it’s … sort of things. But where it really starts getting, I think, super interesting and what we talk about is when those companies start sharing a significant amount of equity. So when they hook … in, they stay hooked in at the level that a VC would be hooked into early stage startups. The idea is to give people the actual freedom.

The reason we call it an “innovation colony” is because we think it’s a throwback to people leaving motherlands and going on long and dangerous journeys out to the colonies to strike their fortune. Did the colonial empires benefit from that? Sure, yeah. They would occasionally get ship loads of goods and gold coins and shit going back home. Was it dangerous and they’d occasionally lose people? Yeah sure. All the time. But it’s the whole risk/reward thing. We think that big innovation cannot happen in the bosom of a big enterprise where you really can’t fail. You have that big safety net like, “Hey you tried. Move onto something else.” You really have to go out and take the kind of risks that startup entrepreneurs take.

Len: You’ve taken some of these principles, I think, and applied them to your books. You mentioned Eric Ries before. The first Leanpub book was an Eric Ries book that was from his blog, and was sort of the - in a sense, a kind of predecessor to The Lean Startup. And I know that your books in particular - so you said, The Lean Enterprise, obviously it’s a Wiley book, you said you pitched it to Wiley. But if I’m not mistaken, it was published in-progress on Leanpub before it was completed?

Obie: It absolutely was, and I’ve blogged to prospective authors saying, “Hey do that. That’s the way to do it.” Because the traditional publishers don’t see it as cannibalizing their sales. So it provides a way to get a significant amount of income. I mean if you are already a known entity and you have the ability to market your Leanpub book - as you well know, you see the actual numbers, right? You can make tens of thousands more before the book is even anywhere near a formal publisher. And then you put it in the hands of the publisher, and they put it through their own marketing channels and whatnot. You make a substantially less percentage on a royalty basis, but I think you reach a bigger audience, so it kind of equals out.

Len: So did you have the deal with Wiley for The Lean Enterprise before you started publishing it in-progress on Leanpub?

Obie: Yes. I mean we went through a very compressed cycle. The whole thing started and was in print in six months. Maybe not in print, but kind of finished in six months. So yeah, I believe we did. I mean, I already had The Rails 4 Way on Leanpub at that point. I had already negotiated that with - at least I was kind of familiar with how to do that.

Len: I’m just really curious. Obviously we were so excited to see it when The Rails 4 Way popped up on Leanpub, and when you came on board. And of course, The Lean Enterprise as well. Was that a difficult argument that you - or case that you had to make for this process? Because it’s something that we think all books should do. Publish in-progress on something like Leanpub before the book gets taken up into the machine of the large publisher. Was that–?

Obie: It didn’t, but I’m going to try to be humble and admit that I’m probably a little bit of an outlier. I mean I have a very good relationship with them. They trust me, I trust them. So I don’t know what that experience would be like for someone who didn’t already have a track record and relationships in place.

Len: Yeah, that totally makes sense. Our hope is that it becomes somewhat conventional and an understood thing, especially for someone who’s starting out and doesn’t have a profile yet. To publish, to start publishing their book in progress, and hopefully get taken up by a publisher - if the book gets traction, and if they can demonstrate that they’re a good writer.

Obie: Yeah, the biggest challenge I think is getting that traction, and actually attracting… Like if you engage with a traditional publisher, at least in the technical world… Well first of all, actually it’s not that hard to get signed to a traditional publisher these days. I feel like a lot of the editors out there are actually following blogs and things and reaching out. And, myself, I got a lot of traction on the first blog posts I did on Serverless. On Medium I had like 15,000 reads. I got a couple of different cold emails from publishers saying, “Hey, would you like to put this on our…” You know, I got reached out from No Starch and from Apress. People who I didn’t have relationships with already. And it’s like, “No, it’s okay, I’m good.” So I can’t be the only one that’s happening with. I’m guessing that they’re going out and reaching out. Because it doesn’t really cost them very much to develop an author, to sign someone.

I think that increasingly you don’t need them as much. Because there’s this great eco system of blogs, and Leanpub is certainly part of it. That can credentialize you, you can succeed and reach a wide audience without needing them. So I think that traditional publishers are going to be increasingly, in that somewhat of a difficult situation, moving forward. The same as the case of record labels and any sort of traditional content curators.

Len: On the subject of Serverless, so you’re going to be launching it within the next week or so.

Obie: Yeah.

Len: I was wondering if you could tell us about what it’s about?

Obie: Yes, of course. So this is rapidly becoming one of my favorite subjects. I love catching new technology waves while there’s still a chance to get really good momentum out of it. And this is certainly the case of a movement, that being microservices, which is very rapidly ascending the Gartner hype cycle. It’s just kind of starting to be on everyone’s minds. I’ve been a fan of the concept for years now. It’s certainly not something totally new. In the earlier stages of my career, I was involved with distributed computing and SOA. And one of my earliest applications that I worked on used Forte, which at the time was one of the most advanced object oriented distributed application environments. You wrote your objects and then they had this whole UI for distributing over different nodes in your network and things like that.

So I know a lot about stuff over the years, and what I see is that it’s really kind of coming together in a way that is enabled by current technology that we haven’t seen before. Lambda is really kind of at the heart of it. It’s a new product from Amazon Web Services that lets you upload functions and run them in the fabric of Amazon’s cloud computing platform, without needing to provision servers. And that is - for someone like me, that’s very, very powerful.

Over the years I’ve gotten involved in kind of countless ventures, the whole lean startup thing, like wanting to put things out there. But you want to know that they’re capable of scaling without having to scramble and lose whatever… But you don’t want to invest a whole bunch either. And there’s this notion of T approximating, with the T variable representing development time or cost. And what happens as it approaches zero. So with technology and everything going the way that it is, you’re able to throw together software in a postmodern way, cobble together third party SAS services and APIs and libraries and open source and things very rapidly. But the final missing piece is - how do you pay for it if you want something that’s capable of scaling? And I think this answers that effectively. And this applies both to startups and also at a place like 2U, where I want to build systems that scale.

But I also want to build them in a maximally modular and maintainable way. And I want my developers to have a lot of power over those environments, and being able to really leverage all the tools at their disposal. And maintaining big, monstrous monolithic applications that have been in service for years - now, you don’t know that you’re not going to break them. You know pretty much any time you touch them, no matter how good your test coverage is and whatnot, things become very brittle after they’ve been in production for a while.

Microservices supports that; what we’re advocating with the book, is just an amazing new world, right? The microservices are basically disposable. You don’t really modify them - once they’re in service, they have a long lifetime. They’re kind of a cell, until they become obsolete. When they become obsolete, because you need them to do something differently - in the best cases, you just deploy the new version alongside it. And then you can go about in a very methodical way, testing whether it does what you need it to. Whether it doesn’t introduce regressions. Whether it performs. You can start shifting traffic over to it. You can leave the legacy microserver in production to service old clients. I mean it’s just a - it’s a very, very different world than the one we’re used to.

Len: For people listening who might not be all that familiar with microservices, can you give me maybe an example that you’ve had in your experience with something like that, where it made a big difference?

Obie: Yeah. At 2U, we do a lot of transformation of files from - basically we integrate with these legacy systems at schools. Without getting into too much details, you can think about it as 20 different partners that all have their - it’s all a very similar process, but each slightly different. So do you develop a monolithic application and clone it 20 times, and then tweak each one? I mean that’s one way of going about it. Or do you spend the time engineering that monolithic application to have all the different adaptors and configurations and strategies and all the things that you need it to have in order to be configurable for each case? But then every time you deploy it you’ve got to worry that - you’ve got to test every single integration. Or do you decompose the problem into a set of microservices, each of which does what it does really, really well? And collaborate with each other over a messaging bus, which is my favorite approach.

So that one can add - one can take it, read the format, and go, “Oh yeah, I know this format.” So it translates it, puts it back on the bus. Another service goes, “Oh here’s a translated - here’s my transcript.” And it can know what to do with this. So it grabs it and it dissects it and identifies, who is the student involved? That sort of thing.

That’s sort of decomposition without getting into too much detail. The example I use in the book is this venture called Food Button, which is the easiest way to get a meal. Some of you can probably imagine being at your desk, and you’re working and you’re in the middle of something. The last thing you want to do is stop and think about what you’re going to eat. But you need to have lunch. So I’ve dreamed about this ideal time of just being able to hit a button on an app or a physical button on the desk or whatever, on my Apple Watch, and 30 to 60 minutes later, magically food appears - cool. I’m not a picky eater. If you’re a picky eater, you will not like this idea. But if you’re not a picky eater, like me, you will love this idea. Which is press a button, 36 minutes later, magically food appears. It’s like, I don’t have to pay for it, it automatically gets charged like that.

Len: That’s a really fantastic idea. I was wondering actually when you were describing some of the issues with say dealing with 20 different systems, that reminded me of a friend of mine who works in government healthcare startup land. And it reminds me of a lot of - and I know you’ve had some of these sort of scandals in the States as well, where people trying to deal with legacy government systems find it’s very, very difficult often to change things. Because there are so many legacy systems with technology from different decades. Is microservices the kind of thing that people engaged to those kinds of very, very large projects could use to solve some of those problems?

Obie: Yeah well, I think decomposition is a trend that predates microservices. And generally speaking, that’s part of the life cycle of a large project anyway, is that eventually you start breaking pieces off of it into smaller bits and pieces. It might be new versions, a functionality, or it might just be things that make sense to partition logically. If you read Microservices by Sam Newman, it’s like, basically he makes the case for never - or maybe not never - but not starting with a microservices approach from day one. Basically, starting normally with a monolith and then breaking it off. Just really have to do not so much with the approach overall, but like the details of what’s involved.

So, for instance, when you go microservices, you decentralize your data. You no longer have kind of a one repository to rule them all. One relational store behind everything. Each microservice has it’s own repository. You get into these so-called polyglot persistence situations where one microservice is backed by MySQL, another one’s backed by Mongo. Another one’s backed by Cassandra. You’ve got your user sessions, is backed by Redis, and whatnot. And you start having this data that’s fractured over different kinds of stores in different ways, different schemas. It’s no longer clear how you do a transaction. And the truth is, you probably don’t. Which means that your developers have to be familiar with the CAP theorem. You now have to understand how these new breed systems like Dynamo favor partitioned data and cluster over consistency. So it means your systems have to accommodate eventual consistency.

These are heady topics for your average developer. This starts to take them beyond their comfort. Imagine kind of like your average Rails developer going, “But I just want to write a controller and some active record”. Whatever. And I’ve had some pushback already from friends who are kind of Agile fanatics and default to YAGNI. You ain’t going to need that, right? You ain’t going to need it. And like, “What are you doing, kind of over-complicating everything?” Well yeah, I agree, I mean you can definitely start with that approach, but there are some problems that, by their very nature, right off the bat, you know that you’re going to need to scale. You know that you’re going to be able to decompose. There’s just a talent to be able to execute that. And I think that the mix of skills that you have to pick up, like the mix of skills that we discuss in the book, basically - planning for this book to be a general reference and also a really solid primer into microservices.

I called it “patterns of modern application architecture”, because I see that this is kind of the way that the future is going to be built. Your application is no longer just a simple three layer beast with a front end and it talks to a database on the other side. We’ve got the internet of things, where you got RESTful APIs for everything. You’ve got mobile clients. You got web clients. You’ve got teams that are actually smart and want to test their shit. So you have to be able to mock things. There’s a whole modern realization of what Alistair Cockburn called hexagonal architecture, and making sure that your application has ports.

And that was in a way in that I really haven’t seen before with this serverless microservice approach for you at the functional level. You deploy them independently. You pay for them in a metered way. More and more, I just think that in the future, people are going to look back at what we did with servers. And they’re going to think it’s like contacting the electric company because you need service. And they arrange with you to set up a little power plant on their premises. It’s ridiculous, right? Like you wouldn’t think it that way. But it’s very similar to what we do now. The abstraction of a server is not part of my domain. Why do I need to think about it?

Len: So is the target audience for this - I mean, is it - is it everybody who works in software?

Obie: Everyone.

Len: Yeah, okay. That was one of my questions.

Obie: My favorite kind of book.

Len: It sounds like it’s making an argument as well. Which is fascinating, and those are the best books, right?

Obie: Yeah, and I’m also trying to write it in an evergreen way. So my biggest agitator so far has been whether to make it specific to Amazon Web Services. But they have a million customers, they’re dominant. I’m not too afraid to go that route. And they’re really killing it when it comes to the pace of innovation there, like Lambda, API Gateway, Dynamo. The whole story that they’re putting together and the way it ties together, I think it’s an amazing platform, and it’s not one I mind aligning with.

Len: Just for any authors listening, or potential authors. I was wondering what your plans are around the launch?

Obie: Yeah, so I’ve been - I have my personal mailing list, which is in the thousands. I have a Twitter following, stuff like that. I’ve been heads down working on the book, so I honestly haven’t thought too much about the launch. Other than to reach certain people, yourself included. I’m also going to have friends and allies that are aligned with the book tweet about it. Tim Bray is high up over at Amazon Web Services. He’s a figure that a lot of us know and love. So I’m sure he’s going to support the book. Other people that I can call upon.

So in all, just kind of leverage my network. Get the word out. And then we’ll continue to work heavily on it. It’s strategic for me in various senses. I’m also writing it for my team at 2U, because I expect that it’s going to increasingly be a part of our future there. So it helps to have your different - your work and play interests aligned in that way. It’s kind of the optimal way to do it I think. If I was trying to do this well running Hashrocket or doing a monolithic Rails app, it just wouldn’t happen. Leverage your strengths, that’s my advice to the authors.

Len: Fantastic. Thanks for that. It’s funny, when one’s already done things a few times, it can often be easy to underestimate one’s strengths and what one’s learned, and advice like that is actually really, really helpful for people who are just figuring things out.

Obie: I think if you’re struggling with your first book, realize that it does get easier. That much already I can tell. This book, I kind of launched into it, and yeah I had a lot of energy, but like just knowning the workflow, knowing how to assemble a team. Have a small team of collaborators. And I’m probably going to build it. Realize that books are generally team efforts. You need competent reviewers and collaborators to give you feedback.

If you want to write a quality book, I guess that’s the disclaimer. And I’m generally very happy with the books that I personally bought on Leanpub. But there is differing levels of quality I suppose. If you go into some of the Kindle books, like I checked out some of the Kindle books on microservices, and they were terrible. Kind of the low budget books. If you want to build a quality product, you can’t just do it on your own, you need people to review it and you need people to check your - to do the editing and stuff like that. You need a cover designer. It’s definitely a team effort to get the best result.

Len: I just have one more question. Customer development is very important for us at Leanpub. If there’s one thing or maybe even more than one thing that we could do to improve Leanpub or add to it, that occurred to you in the production of this book, what would that be?

Obie: I sent a note over to Peter. The - and I think it’s coming in Markua, am I saying that right? The ability to pull in source code from a URL would be awesome. Because in this book, I’m co-developing the Food Button source code together with the book. And at first I was like, “Oh wow, if I could only do like a Git submodule”. Beause I developed a book in Leanpub Flavored Markdown with Git - if I could pull in a submodule, it’d be great, because then I could have the source code up to date. But then that’s complicated even from a personal workflow standpoint. So I was like, “Hey what actually would be good would being able to reference a GitHub URL.” Looking forward to seeing that.

Len: Great, cool. Alright, well thanks a lot for a really great talk, and thanks for being on the Leanpub podcast and for being a Leanpub author, Obie. This was great.

Obie: Thank you guys, I love you guys for real.

This interview has been edited for conciseness and clarity.