An Interview with Reg Braithwaite, Author of How to Do What You Love & Earn What You’re Worth as a Programmer

Published May 16, 2012 by Peter Armstrong

Reg “Raganwald” Braithwaite is the author of four Leanpub books: How to Do What You Love & Earn What You’re Worth as a Programmer, Kestrels, Quirky Birds, and Hopeless Egocentricity, What I’ve Learned From Failure and Steal Raganwald’s Book!

When he’s not shipping Ruby, Javascript and Java applications scaling out to millions of users, Reg “Raganwald” Braithwaite has authored libraries for Javascript and Ruby programming such as Katy, JQuery Combinators, YouAreDaChef, andand, and others.

He also writes about various subjects and sometimes dives into the code. He is known for his popular programming blog.

Follow @raganwald for updates.

This interview was recorded on April 5, 2012.

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

Peter Armstrong: I’m here with Reginald Braithwaite, who is a software developer and well-known blogger. He’s also the author of four Leanpub books, all of which have been created since November 2011. We’re going to talk today about Reg’s blogging, his books, his experiences as a writer and about his experiences using the lean publishing approach on Leanpub. We’re also going to talk about ways we can improve Leanpub for him at the end of this podcast, since Leanpub is a lean startup and we’re doing the customer development process of listening to our customers. So, thanks Reg for being on the Lean Publishing Podcast.

Reginald Braithwaite: My pleasure indeed.

A: So, a few days ago, you wrote a fictional resignation letter which made the front page of reddit and Hacker News — and its clarification also made Hacker News. So, tell me about that.

B: Well, I wrote a parable, some people call it satire, I just thought it was a parable. And I didn’t actually write, you know, put huge disclaimers, “This is Fictional” and so on, I just relied upon the kinds of people who read the kinds of things I write to sort it out. And, yes, the vast majority of people who read it were perfectly aware that it was a parable, or satirical, but a small number didn’t — and my observation is that when people believe something, their personal, emotional investment in that belief is proportional to the amount of, to the size of the leap of faith they have to make to believe it. So if I tell you that, you know, Lisp is a profoundly enlightening programming language that will forever change the way you write software (I’m borrowing something from Eric Scott Raymond there), but I don’t actually provide you with any evidence, but you try Lisp and you feel that way, you can become very emotionally invested in this idea even though you don’t actually have much evidence for it. And this is something I have observed in a lot of fields not just technology. And I did get a bit of a backlash from people who complained that it was fictional. They even used the word “fake” which… I didn’t debate with anyone on the internet, but I think to say something is fake implies an intent to deceive….

A: Right.

B: …as opposed to saying something, the word I prefer is fictional. But I understand how people feel, because there were people who made an emotional investment. They weren’t actually presented with a lot of evidence that it was a true person who had truly resigned. If anything, the opposite: I’d left a number of clues that, you know, in retrospect for most people were quite obvious that it was fictional. But when people make that emotional sort of investment in believing something without a lot of evidence they can get upset when that belief is overturned. I’m sure listeners to this podcast can extrapolate that to a lot of other areas of their lives.

A: Yes. Actually, this leads me into the next idea. Your blog posts often end up on the front page of Hacker News, and there’s quite often a lively discussion of them there and on other community sites as well. How has this feedback loop impacted your writing? Like, I know that for example, they’re not always going to be misinterpreted so much, but you get a lot of feedback right away as you write quite often, it looks like.

B: Yes. First I want to say “it looks like” and I think this, if I may be so bold, I’m not an expert on Lean-anything — my midriff certainly backs that up! — but my observation is that people have asked me: “So, you know, how come all your posts are on the top of HackerNews?” And there’s a remarkably flawed assumption in that question, which is that all my posts are on the front page of Hacker News. That’s not true. Very few of my posts, in proportion, are on the front page of Hacker News–it’s just that I write a lot of posts.

A: Right.

B: I’m prolific. And as a result, say only 1 in 10 makes it to the front page of HackerNews. Well if I write 10 a week, I’d be on the front page of Hacker News every week. I mean I’m just making numbers up; I haven’t actually studied it, but the underlying principle — and I’ve in fact written one of my blog posts, called “Write” of all things, speaks to that very subject. I believe, and I think this is relevant for people who are interested in lean publishing, I believe that one of the things about the way we currently aggregate news, opinions, referrals and so on, whether it be through Facebook, Hacker News, Twitter, reddit and other mechanisms for sharing attention, sharing eyeballs, this bottom-up idea, this idea of crowd-sourcing attention — which is different than the way broadcasting works, where a few people decide what you want to see, a few people decide what movies to watch this weekend, a few people decide what’s printed in the newspaper. When you have this aggregation thing, you sort of ratchet up the “everyone gets their 15 seconds of fame” concept.

A: Right.

B: And because of that, I believe that–and I don’t think this is something that, I mean some people, you know, game it, it’s part of their business — search engine optimization, social media optimization, but I think for people who are looking to write, whether it be software, or whether it be words, or whether it be podcasts, I think there is a real incentive today to turn up the volume. To write more often.

A: Or make extreme statements even.

B: Well, I try to stay away from that to be perfectly blunt.

A; No, I wasn’t talking about you, I was just talking about in general you see, like, you know, “10 Reasons why Apple’s going to die tomorrow”…

B: Absolutely, people do that, people have done that, but that was true when print media ruled the day as well. You know, I mean, trying to be controversial. Rush Limbaugh, Jerry Springer, and so on. I agree with you about that. But I was speaking to the fact that in this day and age I think there’s more of an incentive to try experimenting. To write more often, to try writing different kinds of things.

When you’re writing, and this is an example I gave before I even knew about lean publishing, and please correct me if this doesn’t fit the lean publishing philosophy, but I believe that when you are writing a “dead tree” book there’s this enormous investment in it, which means you have to be enormously conservative. The turnaround time on making a change or an edit is massive. So, dead tree companies spend so much time on, what you might call, up-front quality control. There are editors that review, you have the schedule where you write all the chapters. Whereas when you’re blogging, you just blog. If somebody points out a flaw in your argument, you could take the post down, you could modify the post, you can correct your spelling after people have seen it, after it’s on the front page of Hacker News.

So you asked about the turnaround time, and I believe that there are two factors here. One, the feedback loop is much tighter because you don’t have to wait months to publish a book and get it out there and then read reviews. The feedback loop is tighter, number one. Number two, I think people tend to forget your failures and remember your successes. Now I won’t speak to what happens if you’re writing incredibly offensive things that people, you know, that are notorious, or just notable. But if we’re talking about the difference between stuff that is mediocre and exemplary, stuff that is forgettable and memorable, people remember the memorable stuff. So if you write 10 blog posts and 9 of them are kind of like “eh” or “meh” (I think is what people say on the internet), but the 10th one strikes people’s fancy, that’s what they remember.

A: Yes.

B: And so, I think for whether you’re measuring your success in terms of the influence you’re having over the future of the human race, or the attention you’re getting personally because that gratifies you, or the money you’re making through a venture such as Leanpub, I think the circumstances are such at this time in history and the internet that you’re rewarded for doing things which have a tighter feedback loop, and which allow you to be more prolific. Personally, I find that works for blogging, and when I stumbled upon Leanpub it clicked with what has been working for me as a blogger.

A: Right. Actually, how did you find Leanpub? How did you run into it?

B: Quite honestly, I don’t remember. From the time that you said ‘Hey, let’s talk about this,’ I’ve been sort of, I did some quick searches to try and find out, did someone email me, or something, I strongly suspect I found you through like a Google search or something. But I’m embarrassed to say I don’t remember.

A: It’s interesting.

B: I ought too, but I don’t!

A: Actually that’s really neat in some ways, in the last few months we’ve run into a lot of people who’ve heard of us, and that’s a new experience for us at Leanpub… So, you’re the author of four Leanpub books, and you found out about Leanpub somehow, and then what made you decide to get started with your first Leanpub book, about combinators?

B: Well that one was a very natural fit for me, because what it was, for the benefit of the people that are listening to this and have better things to do than follow my writing, it was a series of blog posts that I actually wrote as a connected series. Combinatorics is a branch of mathematics and computer science, and it’s of deep interest to people who are interested in computer science, but it also has extraordinarily practical applications when applied to programming. It’s not so much a revolutionary ‘you can do things you couldn’t do otherwise’ but it provides a programming style. And people occasionally dip into it, the very popular jquery library for people doing client-side JavaScript, for example, is based very much on combinators, on a subset of the possible combinators. Raymond Smullyan has written a book called ‘To Mock a Mockingbird’ where he exposes this in a sort of recreational math and puzzles form that people find entertaining, and I wrote a series of articles about how this could be applied to Ruby programming in practical terms. And I was already doing that with my blog, and they were already connected,, so every time I wrote a new article about them I always kind of a little table of contents, ‘if you’re interested in this, you’ll also be interested in these other articles,’ so they were already in a form that made sense to package together in a book-like form. I’ve been approached many times since I started blogging to write a book of one kind or another, usually some sort of advanced Ruby meta-programming book type thing, and once I saw the Leanpub concept it sort of clicked for me, literally, that’s exactly what I want to do. I rejected all these all these other things; they just didn’t make sense. I have a copy of a dead tree book by Joel Spolsky, which I like, I mean amongst other things it doesn’t need batteries, and it’s easy to read in the smallish room of your house. But, you know I never wanted to go through the process of writing a dead tree book, and it’s not even a question of the economics — I can always use more money, and I don’t know why I turn down advances — but the Leanpub thing just clicked for me as something I could try, experiment with. The extremely low barrier to entry was a huge win for me. Huge, huge win for me. I currently publish all of my technical essays on GitHub where I was already using Markdown, and I had done this a few years ago, I fell in love with Markdown, specifically because it prevented me from — does this interview have to be safe for work?

A: No, go for it.

B: It prevented me from dicking around with formatting. Markdown is just like, this is what you can do with it, and it makes sense to know what to do about bolding things and emphasizing things and doing quotes and headings, and after that, stop dicking around and write.

A: Yeah, exactly. We added support for images, but similarly it’s like, we don’t support layout options or anything, you should be writing, not laying out your pages, this isn’t a newsletter, like stick it in a cafeteria, right, it’s words.

[Editor’s note: Markdown supports images obviously. What I meant was that we added support for external code samples using a similar format to the syntax for images. The full podcast audio had this correction at the end of it, after the interview ended.]

B: That’s exactly what attracted me. I used to have a conventional blog, where I could do tons and tons of formatting things, and I switched to blogging on GitHub for a number of reasons, and one of them was it forced me to just focus on the words.

A: Right.

B: It was a worse-is-better, sparse, simplified approach, and it really worked for allowing me to be more prolific. I could just bang out more words. I now also use Posterous, I have two blogs, the technical stuff is still on GitHub, and the non-technical, social observations — I don’t know why a guy who has some expertise with programming thinks he also knows about freedom, or politics or something, it’s really ridiculous hubris, but that stuff, I use Posterous, because it works in much the same way. I send it an email.

A: Yeah.

B: And my email client, it does allow me to bold things and so on, and actually if I hunt through the menus I can find other ways to format emails, but my brain sort of thinks that emails are mostly text. My brain doesn’t try to format things and how they’ll appear on the page and whether I could stick an Amazon affiliate ad link on there or whatever, my brain doesn’t do those things when I’m in an email client, and that allows me to write more.

A: I know exactly what you mean. We actually, at Leanpub we used to support HTML or Markdown, because we figured, well Markdown, some people might not like it, but then people tried to do lots of formatting, with their HTML, and we’re like, No, you only need the HTML that you need in Markdown, and it’s like, well then why don’t we just use Markdown? Okay… yeah.

B: Exactly. My theory is that if any of my books become extremely successful, then I will be able to do a royalty split with a designer, who can fiddle with things, and if they’re not successful enough, then I’m not going to do that, and I don’t believe that there is the case of a book that I write, where if only I formatted it beautifully, then people would buy it. I’m not in that business. There are such books, coffee table books, children’s books can be incredibly effective when you pay a great deal of attention to the design and layout, and so on, to create interest, this is not a general-purpose piece of advice for people about writing, but I think for my writing it’s perfectly appropriate to just focus on getting the words out, and then you know in the fulness of time, and I believe this is part of your philosophy, if any of these things become a huge hit, then I can reconsider going to a different system, where they are more laid out, more formatted, and possibly monetized in a different manner that can take advantage of their layout.

A: Yeah, exactly. For us, it’s like, we see Leanpub as the best way to self-publish in-progress ebooks, and, we feel that publishers have some value, but the value they offer is at the end of the process, in terms of taking something that’s good and adding polish to it, but that if you take them and bring them in at the beginning of the writing process, it can have effects that you don’t necessarily want. And also publishers are good at putting physical books into channels, something that we don’t have any interest in doing. So, what you’re saying is completely the Leanpub philosophy…

So we’ve talked about your first Leanpub book. Tell me about the other three that you currently have on Leanpub.

B: Well let’s see, from memory, I have one called Steal This Book, this is my favourite and I believe least popular.

A: Yep.

B: That one I am trying to give away, and not making much headway. So, my observation about that one is that people like free stuff when they think that it has a monetary value and they’re getting it for free.

A: Yes.

B: If you tell them…

A: If you had a one-day sale on Steal This Book where it normally cost $20, I’m sure you’d have about ten times as much.

B: That is my exact experience because I did have a one-day sale on one of my other books which was How To Do What You Love And Earn What You’re Worth As A Programmer. So, I’m going to come back and talk about that, or I assume you’ll ask me about that, because I think we both learned something from that one-day sale. The third of the other three books is called What I’ve Learned From Failure. That book I believe is the most valuable book I’ve written so far. That, I started blogging at a time when, it wasn’t even a blog, it was just essays on my own personal website, and they would get discussed in like Google Groups, the equivalent of, Usenet groups and stuff like that, and people could just follow them and could read them and then tell me what an idiot I was and so on. I was mostly writing about Agile methodologies and my experiences as a software development manager, and I wrote a book called What I’ve Learned From Failure where I listed four software development antipatterns and talked very frankly. I mean, it was one of those, sit down in front of a keyboard and open a vein, essays, it was very heartfelt, and it was my first, sort of, big internet hit. And, over the years I’ve continued to return to the theme of software antipatterns, not always in a nasty way, sometimes in a very positive way, but about things that we believe to be true about developing software, that aren’t really true, and why. And What I’ve Learned From Failure is a collection of essays that meet two tests, number one they were all popular, one kind of another, Reddit or Hacker News, I mean some of these go back to before there was a Reddit, and the other test is that I personally have a big emotional investment in them. And I think if I remember correctly that was my second Leanpub book, after Combinators.

A: Yeah.

B: And, that one, I actually, if I remember correctly, I originaly charged like ten dollars for the Cominators book, and twenty dollars for What I’ve Learned From Failure, and my theory was that the kinds of people that are interested in software development, at that level, are tech leads, software management managers, working programmers, and therefore they ought to be able to afford one.

A: Right.

B: And, you know, I have no complaints with the people who bought it for fifteen dollars or twenty dollars, or whatever I charged at the time. Over the years I also constantly got asked for advice about getting a job as a programmer, and some of the most discussed — discussed, not disgusted! — commented upon things I’ve ever written have been around either a personal passion for software development, or around getting a job as a software developer, they’re deeply related issues, or about interviewing people, and I hastily threw together a collection of those articles, which is, which formed the basis for How To Do What You Love And Earn What You’re Worth As A Programmer. But I didn’t put nearly as much work into sort of fixing up the essays and it was kind of the red-headed stepchild compared to the other two books, and sales weren’t really going anywhere with it, so what happened? Well, I wrote an essay in conjunction with your excellent work, the name of the book fails me, but you wrote a book in support of the EFF?

A: Yeah, Uncensored. We did a…

B: …Uncensored, yeah, that’s right, pardon me, having a senior moment here, you know, ready for another espresso, but — I wrote another essay for Uncensored, called ‘I have a bad feeling about this,’ and that one, not quite at the level of ‘I Hereby Resign,’ this week’s thing, but it actually got a tremendous number of retweets, views, discussions on Reddit, discussions on Hacker News, it really struck a nerve with people. Unfortunately as far as I can tell, they didn’t really all rush to buy the Uncensored book, which is really bogus…

A: …yeah, I don’t know…

B: …but that’s, those are the breaks, and you know I mean, our job is to lead horses to water. But it really struck a nerve with people, and I sat there, after writing it, and I had a real impostor syndrome feeling, like here I am, talking about intellectual property cartels and freedom, and I do write, I’ve written a number of free sort of programming libraries that I give away, and all of my words, I don’t think there’s a single essay or anything in one of those books that isn’t also on the web somewhere, for free. I like to think of myself not so much as selling the ideas, as selling a convenient format for them. Like I sell packaging but the ice cream’s free.

A: Yeah, I know, exactly. Basically your selling the blog, like if you just do a vanilla import into Leanpub, we’re just taking your blog and just reversing the order, basically.

B: Yeah absolutely, that’s it exactly. So I had, I’m not going to say a pang of conscience, which makes sound like I shaved my head and became a Buddhist something, which is ridiculous hyperbole, but I did have a kind of feeling about it, and I wanted to give something away. And uh, the How To Do What You Love wasn’t really doing well financially, compared to the other two, you know, first world problems here! And you know when I thought about it, it kind of had the most value in another way, different than the value of the Combinators book… I mean fundamentally that’s a, you know, you’ve already got a job, you’re already doing something, here’s a way you can do it better; but it’s not going to like help you get a job to read my Combinators book — that’s not what it does.

A: No.

B: That’s not what it’s about, it’s for people who really love their craft, and they’re like interested in it, and the What I’ve Learned From Failure is a book for people who are leading teams or aspiring to lead teams, or who are influential in that process, and again I’m sure there are some people working in not for profits and so on who don’t have a lot of money to spend on a book, but fundamentally, there’s a real economic value their that you can touch, and you know honestly if someone doesn’t want to buy it, I don’t need to give it to them to make the world a better place.

A: And most of the readers of that book are already successful. If you’re reading this, you’re a software development manager.

B: Or you’re an employed developer who wants to print it out on paper, roll it up into a tight tube, and then hit your manager with it. READ THIS BOOK!

But, How To Do What You Love had some stuff in there that really I felt like, man, if there was anything I should give away, this is it. I mean there are some people it’s ridiculously arrogant to think that there people you know whose lives will be horrible if they don’t read my words on how to get a job or how to be passionate about your work, I mean no, not at all, and you know especially when you consider that I hadn’t really put a lot of work into making it a great book, but I really kind of felt like, you know what, if this isn’t really like taking off, like give it away, let people just use it, they’re already free, but you know here’s another channel by which people can take advantage of these, and hey, if there’s one person who gets it, you know a bunch of people download it, if there’s one person who gets a job because of it, you know, or who gets another $5000 a year because there’s a tip in there about negotiating your salary, you know, or something, it’s like yeah, the world’s a better place and that’s much more important than making another fifty bucks or something in royalties. So I said yeah, let’s do it, and don’t ask me why but like I had this idea, one-day sale, you know just like, tomorrow it’s free! Go get it! And for some reason, that struck a nerve with people, it was like, ridiculous.

A: My cofounder Scott submitted it to Hacker News. We normally don’t submit any Leanpub things, but he submitted that one, because usually your stuff ends up on Hacker News anyway, and we try not to be like annoying about things. But he submitted it because wow, this was cool, and it just took off. Like, you had thousands of sales that, in terms of thousands of downloads of free sales but also paid sales that day.

B: A ton of paid sales that day. And there were people who were commenting that they felt guilty, they felt pressured, and so on, and I had to go on Hacker News and say honestly ‘No, I’m sincere, take it!’

A: One person was made about our slider, like, ‘The slider makes me feel guilty’, it’s like “yes!” We brought a designer on, and the first thing I asked him to do was, I want a royalty slider, I want it on the purchase page, I want you to drag it to see how much you’re paying, I want you to see how the royalties get affected, and we were joking about how when you drag the price down, you should like show like food being removed from an author’s plate or something, or else, we were joking about making the colour of the slider all red… And we’re like no, let’s just go for a light happy green, light grey, meh, as it gets cheaper, and I think we hit the right balance there, where most people thought it was cool, some people got angry but lots of people kinda liked it, and you got a lot of revenue from that, it was like the best day for a book, it was pretty fantastic.

B: Absolutely. It did in fact blow up, and I told people, hey, you know what, if you really feel like sending me any money, you don’t even have to like pay for this book, take it for free, and buy one of my other books. Get a twofer if you feel like spending, but — it was financially successful, which was great, and it did get — I haven’t checked this morning, but I think maybe 7600 people have downloaded the book, in total, and there have been continued, and it actually motivated me to go in there and clean some things up, and tidy it up… And then when you worked on the EFF thing, that you know it sort of struck a chord with me again, and I made the fourth book, Steal This Book!, you know there’s been a theme on my blog from time to time about freedoms, it’s something I believe in very very deeply, in the importance of information, and opportunity being accessible to everyone. I recently wrote something, which is now in Steal This Book!, it’s the latest chapter of it, which is called A Woman’s Story, which is about my mother, and about her becoming an early programmer. Some people said the first black woman programmer in Canada, I don’t know if that’s true, I haven’t done as survey, but certainly one of the earlier ones, I think she got started in the late ’50s, in programming, and you know the machine has the power to democratize us, it as I said in the essay, which is something that she told me, you know it didn’t care that she was a woman or that she was black. The machine doesn’t care that you’re in, if I remember correctly, in British Columbia as opposed to being in Silicon Valley. I mean, humans care, you make deals, and you bump into people at the coffee shop and so on, but you know the machine does give more opportunities. It’ll never be a perfectly level playing field for everybody everywhere regardless of where they came from, but the Internet and openness do create more opportunities and they give us more chances and they make it more possible for small businesses to grow into really huge businesses and so on, and I think those all of those things are important both for moral ethical reasons and for economic reasons. I think that the more open our societies have been, there are a bunch of reasons why North America has become very successful economically in the last fifty years, cheap oil for example should not be ignored, but, a certain amount of that does come down to people’s freedom to be able to start a small business, as you do, that can sell books to people all around the world, and to do so with very little friction, and you know that’s the same thing that, it’s connected in a deep way, in my opinion, to being able to get on the net and read books, and learn things, without having to pay a university to teach you something, or without having to buy a book, that you can get something for free, you know the Internet will be my childrens’ library system, and you know I’m sort of really, deeply, deeply, deeply impressed by Leanpub in that aspect, it’s not like I’ve been to your offices and looked at them, or met you in person, it’s like, wow, this is, you guys are gonna change the world — I can’t say that, but I can say that Leanpub to my, in my opinion, is emblematic of, or symptomatic of, or an exemplary example of what makes this time and place in history with the Internet, and openness, and accessibility, so special, and so wonderful, this idea that people can write words, very simply, create a book, maybe make some money, maybe share it, you know maybe make their reputation for something else, and do so with very little friction, without needing an editor, a selector, and trucking physical books, or you know, an ISBN number that you have to apply for and so on, all those things to me you know they resonate with my personal beliefs, my opinions! Let’s face it, I’m not an economist, I’m not a futurist, I’m not an expert, but I believe it’s important, and so it clicks with me.

A: Thank you very much. That’s really nice to hear. Wow.

Speaking in terms of Leanpub, for us you, our opinion about what we’re trying to do in the world, is the writer and the readers, for the writer it should be you sitting at your computer, writing words, and then you click a button, and then everything else should just happen magically, and readers should be able to get your book instantly and as often as you want, you shouldn’t have to have approval from anyone, you shouldn’t have to wait on anything, we want to be this sort of thing that enables authors to connect with their readers a lot earlier than otherwise and a lot easier… That’s what we’re trying to accomplish. And I think it’s, from what you said, it sounds like we’re getting there.

So, is there anything that you wish that we’d improve, in terms of what we have now, feature-wise, or in terms of for you as an author, or for your readers?

B: Good question. I do have a couple of ideas. First, I love the Dropbox integration, I’m crazy about it. I actually, I mean this is maybe just me personally, but I would like to see either something like GitHub integration, or in the fullness of time, with your you know staggering software development resources -

A: Ha!

B: I’d like you to build something like that…

A: We actually already had it! We had GitHub integration before Dropbox. At one point, before you showed up to Leanpub, we had two choices: you could write the book using Markdown and sync with GitHub, or you could write the book in a web browser. (We’d forked WordPress.) And what we realized was that the GitHub thing was not accessible to everyone, and the in-browser experience was terrible.

B: Yes.

A: …for a book. Like it’s fine for writing a blog post, but for writing a book it’s terrible. And so we thought, well, they both suck. Well, the GitHub we really liked, because we’re geeks too right, and GitHub made sense for us, but it’s, so, but I couldn’t tell, like my father to use GitHub.

B: Yes.

A: So, we’ve had some Dropbox flakiness recently and I’ve considered thinking hey, should we bring back Git and GitHub as an option for the technically sophisticated authors who want to be able to, say, git push, and have that trigger their book generation. Is that what you’re going for?

B: No, actually. Personally, I’m actually one of the most ignorant programmers I know. I’m just terrible with all sorts of tools and git push and forking and so on. I was thinking more, I’ve been talking to the Mozilla Foundation people lately about some of their visions, something really exciting they’ve done recently called Boot to Gecko for, boy if I use an expression like ‘low-end phones’ you know it’s like so emotionally laden.

A: [laughter] ‘Ghetto phones.’

B: For, yeah exactly, but you know what, let’s use that word, ‘ghetto phones’, because the fact of the matter is that of the six and whatever billion people on earth, at least three billion of those live in what we would consider ghettos.

A: Right.

B: So, a ‘ghetto phone’ is actually a really important thing. So, what they’re doing in Boot to Gecko, and I don’t speak for them so anybody listening to this, you know, if you in any way think ‘that might be neat but it sounds like it sucks because A and B and C,’ assume that the ‘might be neat’ is true and you should look up Boot to Gecko, and ‘it sucks because A and B and C’ is just my misunderstanding. So, if it sounds interesting, go find out more.

But, what they’re doing is creating phones that boot into a web browser. There’s nothing in between there’s no, like you boot an operating system and a web browser is one of the 27 application icons on your screen — it’s all a web browser, if there are 27 application icons, this are images that you tap on, you know, just like you were faking an iPhone in a web browser. And one of the things that’s super interesting about that of course is that it bypasses all of the big questions about application distribution and blah blah blah and so on. So, why I mention that, is that in a world where half the population of the earth had things like this, maybe they had a boot to Gecko tablet, and when I think about that, I say to myself, What are all of the things that you can’t do on a tablet easily? Well, actually, fooling around with Git is something that you can’t do on a tablet easily, it just, Git is just so tied to our conventional notions of file systems and so on it just doesn’t work. I realize that WordPress, a custom forked version of WordPress or plugin that published to Leanpub or whatever it is, you know is not appropriate, especially the way I think about Markdown and so on. But, I do hope that one day it will be possible to write a book entirely in a browser in a way that is actually closer to the philosophy of what you’re trying to espouse now. Not fooling around with all sorts of styles and so on, but being able to have various chapters, to organize them, being able to create new content, Git right now, GitHub you go online, they don’t allow you to tap a new Markdown file button

A: Yes!

B: …they allow you to edit one that exists, but they don’t allow you to tap a ‘New Markdown File’ button.

A: Yes.

B: So, I, when I say GitHub, I mean to my mind, that’s like three steps backwards one step forward, but I do hope that one day it’s possible to be able to do something like Leanpub entirely from within a browser, and I think that would make the concept instantly that much more accessible to people.

A: The funny thing is it’s actually not technically that hard. We actually use Git internally as well. Like whenever you click publish, like, we had to wipe some of our old history because we used to do this badly, but whenever you click ‘Publish’ or ‘Preview’ for you book we make a new Git version of your book. So one of our ideas is that, for example, you know, imagine someone writes a great work of literature on Leanpub.

B: Right.

A: …imagine if like Ulysses had been written on Leanpub. You know how many PhDs would come out of looking at the diffs?

B: Exactly.

A: You know, you can say well here, in this version he said this, and then 22 versions later… But, the notion of version control, trying to explain what you do as a software developer to someone who’s not a software developer, I can say look, I can look at a file from nine months ago, compared to now, I can see exactly what changed in my writing, in my code, why can’t I do that in my writing? It’s like science fiction, right, and then you say, well the answer is the reason you can’t do this, is you’re storing your writing as a bunch of ones and zeroes like as a Microsoft Word document, instead of storing it as text.

B: That’s right.

A: So, to come back to your suggestion, I think it’s really doable, in that we could just, now that we’ve just decided, Leanpub has bet the company on Markdown, we think Markdown is the way to write a book, we could expose a new ability to edit Mardown files and create Markdown files in a browser quite trivially, I mean I think there are already perfectly good, because it’s just plain text right, we could do that without a problem.

B: And there are Markdown preview libraries out the yin-yang.

A: Yeah, live preview, HTML and Javascript, you just, there you go, it’ll show you exactly what it is.

B: And you can always use the GitHub API in the backend, to continue to store these things in GitHub…

A: …h no we don’t store it in GitHub, we store it ourselves, in our own Git repositories.

B: Oh, in you’re own Git repositories.

A: We don’t use GitHub for that. What we did before — the only thing we use GitHub for is so that we didn’t have to do a huge hassle around like Gitosis and whatnot. We figured anyone who’s already using Git already has a GitHub account, and so we’ll have them add us as a like a deploy key or something.

B: Perfect.

A: Yeah, whatever, but if I tried to explain myself how to add as a deploy key you can see why this is… it’s very elitist.

B: And a lot of it doesn’t even serve programmers very well. They’re you know they’re just artifacts of history, what we’d call accidental complexity in design — you know the way these things work. But I think you get my underlying idea — I’m really excited, and I’m not saying, you know it’s sort of trivially easy if you sort of write down the raw features, you need to be able to do this and do this and do this, but to be fair, you could say the same thing about creating a touchscreen telephone, but you know there’s a palpable difference between well-designed touchscreen phones and poorly-designed touchscreen phones. And I think the concept of ‘I need to be able to write a book online using Markdown’ is a tremendous design challenge, and you know I personally would be phenomenally impressed to see it done well, and I hope you guys can pull it off. I just wouldn’t want to promise anyone, oh yeah, yeah…

A: Yeah, I’m not gonna say ‘Yeah, I’ll launch that tomorrow’…

B: Maybe you should test it, you know, that’s the ‘lean’ thing to do. What’s the smallest thing we can do that can test our ideas, that can validate this business proposition, or the value proposition, and so on. You know, more to the Lean Startup concept. But I’m super excited about that being the future of communicating.

A: Excellent, wow. Is there anything else that you can think about that, in terms of… So one thing, for example, you obviously already have a lot of people commenting on your books in places like Hacker News, Reddit etc. — do you want Leanpub to do more to try to facilitate community around your books specifically? Or, do you find that you get enough communication through all the existing channels…?

B: Right. So there’s something. So I’ve noticed, so I’m a bit of a slacker, and I just give out the Leanpub homepage. I notice other people like build their own home pages for their stuff, so, you asked me about community, and I think in order to answer, I think that’s kind of a step two, the step one is branding. Now I’m not sure everyone needs to have their own custom home page for their book. I mean maybe that’s an advanced feature where there’s a tab, for the super advanced people, down the road for you, but before I would get to community, I think a really easy way to be able to say, for me to be able to go get, you know,, or .ca or whatever, and then have to go the page you already host. GitHub has found a way to do that in some sort of awkward, nerdy programming way. And now if you go to it’s actually going to take you to a page hosted on GitHub’s servers. And I would say in order for me to be excited about building a community, I’d want to control my brand, and if you could facilitate that, then I’d be super excited about tools that would allow me to build a community.

Now, all that being said, you’ll notice it hasn’t stopped me from publishing books with what’s already there, so…

A: And today you could just redirect, if you wanted to make, like a sort of no-brainer solution where we do nothing is someone can make a URL and point it, direct to like their book is. But I see what you’re saying, that you want to mask it so that you, you’re saying so that if someone goes to then they end up on your book page, or if someone goes to then they end up on some sort of author page featuring you and all your books, or…?

B: I think, I’m not an expert on DNS. Given that is hosted somewhere else that might not be a good example, but let’s take as an example. So I’m getting a brand new domain. I believe that this can be handled now, if instead of giving me, you give me

A: Oh, we could do that today. You don’t have to do anything. That was, ironically, we went back and forth on which is better, that’s like, the subdomain, like, that, at one point we had that approach, I’m not sure if it’s when we had the forked version of WordPress, or… actually, I think we might have even at one point not have been opinionated and we may have supported both. I know that, it’s just Rails routing, we can just do that, it’s not a problem. But the thing is, we decided people, we erroneously possibly decided that people wouldn’t care whether it’s or, we felt they both kind of were roughly as good, like in terms of number of characters, but for you actually, for you it’s better the other way?

B: Well, if you support, my understanding is that you can then, you need to do one other step, and if you do this one other step, then it makes it very easy for me to create If you look at the way GitHub pages works…

A: Oh…

B: All you have to do is create a file called CNAME…

A: Yeah, I get it now.

B: Yeah, so that’s what I’m imagining. I’m imagining you give me and then in your instructions you say ‘And oh, if by the way along with your Book.txt, you upload a CNAME file with this format, then it would work exactly the same way.

A: Interesting. We’ll have to talk about that, it’s quite possible.

B: Because I know people like our compatriot The Grumpy Programmer, I think he has a custom website for his book which you then click a link to come to your site.

A: That’s funny, one of our first successful books was Manuel Kiessling’s Node Beginner Book, and he set up a whole blog based, well before he made a Leanpub book he had a free tutorial, but then like he’d set up like a really nice blog… Basically, the requirement for us turned into: Leanpub book pages should not be so ugly that people set up an entire WordPress blog just to say ‘Yeah, ok, click this button!’ and that’s the point of the WordPress blog, is to click the button and then that takes you to Leanpub and then you buy it. Because like our book pages used to be horrible, and now they’re passable…

B: They’re beautiful! I like it!

A: …and, I think that, you can see that our book page looks different than the whole rest of our site, because, well, we have Steve doing design work for us, and it’s like well, what’s the most important page on Leanpub’s website? And the answer is the author’s book page, so….

B: The page that holds the ‘Buy’ button!

A: …the page with the ‘Buy’ button! Right, and the page that the author, is their face to the world in terms of their book. Right, that’s the most important thing, and so that’s what we turned Steve loose on first, and then everything else, is sort of, our sort of programmer design, and it will, you know, the rest of Leanpub will end up looking that good as well, it just has to take a little while.

…Um, wow, so, I think we’ve probably gone pretty long.

B: Yes, I’ve used up a lot of your time!

A: No, it’s been really fascinating for me, and I think for our listeners as well. Reg, thank you very much for being on the Lean Publishing podcast and for being a Leanpub author.

B: Well, thank you guys so much for creating this, and as I said, and I’m not kidding, obviously I’m not a venture capitalist, I can’t pick winners, I can’t tell you who the next Google is going to be, but I do know that what you’re doing is important, and I do know that what you’re doing is, I believe, the future of publishing. And if anybody’s gonna become, you know, multigazillionaires with yachts and so on, I sincerely hope it’s you guys.

A: Well, thank you very much.

Originally published at

One clap, two clap, three clap, forty?

By clapping more or less, you can signal to us which stories really stand out.