An interview with William S. Vincent
  • July 23rd, 2019

William S. Vincent, Author of Django for Professionals: Production websites with Python & Django

1 H 2 MIN
In this Episode

William S. Vincent is the author of the Leanpub book Django for Professionals: Production websites with Python & Django. In this interview, Leanpub co-founder Len Epp talks with Will about his background in book publishing, how the book publishing industry changed in response to Amazon, what a book editor really does and the role that agents play in the current publishing landscape, his experience with startups, learning to program and writing books for people who are learning new things, and at the end, they talk a little bit about his experience as a self-published author.

This interview was recorded on July 2, 2019.

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

This interview has been edited for conciseness and clarity.


Django for Professionals: Production websites with Python & Django by William S. Vincent

Len: Hi, I'm Len Epp from Leanpub, and in this Leanpub Frontmatter Podcast, I'll be interviewing William S. Vincent.

Based in Boston, Will has had a diverse career, starting out as a book editor at the publisher Houghton Mifflin, getting an MBA, working for startups, becoming a software developer and teaching Computer Science. Eventually, he successfully moved into a career doing the roles that he's filling now - of teaching, writing, and self-publishing - which he's been doing for the last two or more years.

You can follow him on Twitter @wsv3000, and check out his website at Sign up for his newsletter at, and you can listen to his interviews on the popular Django Chat podcast, which he co-hosts with his colleague Carlton Gibson.

Will’s the author of three Leanpub books, Django for Beginners: Build websites with Python & Django, Django for APIs: Build web APIs with Python and Django, and his latest book, Django for Professionals: Production websites with Python & Django*. [You can also buy his bundle here - eds.]

In this interview we're going to talk about Will's background and career, professional interests, his books, and at the end we'll talk about his experience as an author.

So, thank you, Will, for being on the Frontmatter Podcast.

William: Thanks for having me on.

Len: I always like to start these interviews by asking people for their origin story. You've got an interesting one, in comparison to the typical guest on this podcast. I was wondering if you could talk a little bit about where you grew up, and how you first became interested in books and publishing?

William: Sure, yes - I loved your intro. I'm still working on the short version of my background. But basically I grew up very non-technical. I grew up in Vermont surrounded by books - no computers. Computers - this was the 90s, were always broken and buggy - and I had to kind of fix it for my family, but I always hated doing it. So I never thought I'd be involved with computers.

I started my career, as you mentioned, as a book editor. And I'm now publishing books on programming, so I've gone kind of full circle.

But I really came to it later in life. I was working in publishing, I was a book editor, a dream job, going extremely well - and then I saw Amazon coming in. So this is 2000 - six, seven, eight. I saw them just completely dominating the publishers. I saw the publishers sticking their head in the sand, and And I saw the colleagues that I aspired to be getting fired, with no good job prospects. So I thought, "Well I'm 26, I'm going to figure something out here.

Len: Just to pause you there, because this is such an interesting moment, I don't really want to sort of get over it too quickly. So you studied history in university, if I'm correct from LinkedIn?

William: Yes, history, econ - lots of stuff.

Len: And you decided to go into the book publishing industry to be an editor, I believe?

William: Yes, that's right.

Most people don't understand what editing is. I have an MBA, so I have years of experience explaining it. It's really not staring-at-a-paper editing. I mean that's a tiny, tiny part of it. Really it’s - this is an abused term now, but really it's a product manager. Except I would say more, because a modern book editor is doing acquisitions. So you're dealing with agents, you're negotiating lots of stuff on that. You're doing the editing, but you're also really in charge internally of the whole publishing pipeline.

You acquire the book, you go through all the edits - and then you hand it off to copy editing. Then there's marketing, publicity, jackets - all the rest. It's published, then a year later you come through for the paperback. And you're doing this for - it depends on the publishing house, but two or three seasons a year. So it worked out for me, I was doing about 15 books a year. But at any one time, I was working on 45 different books.

Len: And when you say, "acquire a book," how did that process work in your experience?

William: This is the traditional "trade" model. I'd also worked in academic publishing in college before, where there's really no advances. But trade publishing is the kind of books you would buy in a bookstore. So I was non-fiction, fiction, the Best American series.

But the way it works in the modern world, is, you have agents. Because there's so much volume. So as an editor, you have relationships with agents. And there's a small number of major agencies that will do a book proposal.

So a book proposal would come in, usually it's 20 to 40 pages, and it basically lays out the background of the book. For fiction, it has a writing sample, and sort of gives hints to the plot. There you're evaluating on, how good is the writer, do they have a platform? Platform's not really that important [for fiction]. Non-fiction is all about platform. So a platform would be - it's a book on psychology, and it's a professor at Dartmouth College, and it's much more about who they are and what the topic is. And then it's just assumed, it's less about the writing quality.

You get proposals all the time from agents. And you're reading those, you have assistant who read those for you. I started off as an assistant and worked my way up.

And then if you like a book, from the agent’s point of view, they will have a book auction. So if they have three editors involved, it's like a blind bid auction. And basically they want to get as much money as possible, and there's a couple levers around advancea and other things you can negotiate - but it's very commerce-heavy, I guess is the point.

The amount of time you spend actually editing - the only editing time I spent was like nights and weekends. In the office it was non-stop product management, and trying to acquire books.

Len: Thank you for that great explanation. It's one of those things that, for a lot of people, they only know it from the other side.

Len: And they will only ever know it from the other side, which is from the side of the aspiring author. From their perspective - it's funny, you bring it sort of modestly, what it's like, explaining what a book editor does, to a sort of stereotypical MBA. But to aspiring authors, a book editor is the gatekeeper.

William: Yes - but it's not the gatekeeper, it's the agent.

Len: I suppose.

William: It's actually the agent. No, 100% - the best editors become agents for their authors. Like, John Grisham's editor became his agent, and I'll tell you why: because agents get a percentage. Agents get 15% usually of earnings from an author, whereas the editor is very poorly paid. So you're crazy to stay an editor - unless you really like doing it, or you don't want to be an agent. And it gets more and more pre-processed. So a lot of times, so John Grisham's agent will - I doubt that that publishing house does much editing to the book, right? That's done. They kind of do it before and present it as-is, because of who he is as an author.

But the thing is, editors, just from a volume perspective, they can't look at unsolicited manuscripts. And actually often won't. Because someone sends in - this is like movie studios and scripts, they won't look at something that's unsolicited. Because if you send in an idea, and then they do a movie - you can sue them and say, "Oh, I pitched you that idea, and I have proof that your mail office opened that thing - and so you were inspired by it, and so you have to pay me."

There's not enough money, so people don't really get libelous about it. But that's the same reason. So the number one advice for a trade book author, is "get an agent."

Now, for technical books, which we can talk about, you don't have agents involved. But if you want the Great American Novel, or a big pop non-fiction, Malcolm Gladwell thing, if you get the right agent, you will get a book contract.

Len: Okay, I see. I guess I just used the wrong terminology - so, first you need an agent, that person is the gatekeeper for your entry into the book publishing world. But then there needs to be someone at a publishing company that participates in an auction that is initiated by the agent.

William: Yes.

Len: And then, ideally from the agent's and an author's perspective, there's all these book acquirers competing to offer the highest price for the -

William: Yes. And that's the value that an agent brings, is that they understand the marketplace, they understand the editors. They drive up the prices, but they also save everyone time. So when they get a proposal, they know - they're thinking, "Oh, Will at Houghton would be good for this." They're calculating if they should invest the time, because they're not getting paid upfront for their work. They only get paid if they sell something. So they're heavily invested in the success of their authors. And, as in anything, there is a very strong hierarchy of agents. I could list a couple - if they selected your work, you're going to do well.

It may not be a best-selling book, but you'll get a good advance, and it will definitely be acquired.

Len: It's really interesting you bring up this concept of hierarchy. Because the book publishing industry, the trade book publishing industry has its own unique culture. You mentioned there's distinctions between non-fiction and fiction in various ways, and the world of fiction - and especially like high literature, has its own culture.

I bring that up, because I wanted to now get to where I interrupted you. Which is - there you are in the mid-2000s, around the time Kindle is coming out. And you see these publishers with their heads in the sand, a situation which many people feel persists to this day.

William: It does.

Len: I remember being at a conference, at the Book Expo America conference in New York, I think it was 2013? So it's a while ago now. I might get the companies wrong. But there was this panel - and I think it had the CEO of Simon & Schuster, and the CEO of OverDrive waving an iPad kind of aggressively in her direction, saying, "This isn't a science experiment, this is real." And the CEO of Simon & Schuster is on lists of like The Top 50 Most Influential Women in America.

And here you have someone just - he wasn't trying to be rude, he just couldn't believe that the top people at the top of the publishing industry were - and I'm not making any particular claims about the CEO of Simon & Schuster myself. But this guy was clearly exasperated at his situation, that this technology, even in 2013, was being kind of ignored.

William: I have a perspective on this. Further, there's been rapid consolidation in the industry. Houghton was bought, it had been bought and sold once before by private equity groups - which is a whole separate thing I didn't get into. And then it was merging with Harcourt while I was there. So basically - because the industry was sort of on a downward trend, which continues today, they were just firing people and cutting out parking and publicity and sales - and basically making it less fun. Because people always knew that you weren't going to be rich in publishing. But they enjoyed doing it, they enjoyed the work. And then basically these conglomerates came in, and, in my opinion, killed that.

So when I went to business school, I was saying exactly that - "Why don't they see reality?" [Now] I have more empathy for their perspective. Which is that - just as in any field that's being disrupted by technology, someone who's at the top of a publishing house - so they spent their entire career in publishing, traditional publishing, 20-30 years. They're only there for two to four or five years max. So even if they are totally convinced, and even if they think they can start implementing the changes - all they're going to end up doing is firing a ton of people and pissing off all their colleagues, and then the next person's going to get the credit for it.

There's no incentive to make that huge break. Because they see that it's coming, but all their money is made on the traditional way - the whole staffing model. So Kindle was paying to digitize the books, because the publishers, including Houghton, didn't want to do it. Because they're like, "Why would we spend money on this?" The economic side of it too, you make way less on an ebook. Plus, publishers are paranoid about piracy - which as a technical book author, I think is hilarious. Because your average fiction reader isn't able to pirate books.

But yeah, they're just in a tough situation. I'm still frustrated by them, and I think the industry has to change. But, my colleagues today who have stayed in the industry - what's happened is because you can self-publish with Leanpub, or just on Amazon, you can take a Word doc and publish it. So the role of agents, the role of editors - now they just look at the self-published list, and they do book contracts based on that.

The problem is that the value of a traditional book publisher has greatly diminished, in my opinion, from what it used to be. As an editor, you're not afforded the time to spend with authors that you used to have. I was working on 15 books a year, that's 45 books at a time - that's a lot of books. I couldn't spend anywhere near as much time on them as I wanted. So they had to come in fairly polished, basically.

The other issue is the marketing and publicity budgets were just slashed, because that's an easy thing to gut. Plus, publicity - where they used to call up their friend at the New York Times or whatever paper, and get reviews, well, all those people have lost their jobs. So there's really nothing for those folks to do, right? The whole industry is feeling this contraction. You have the book layout people, they love doing beautiful book layouts for print. They don't want to spend any time on the ebook one. Plus, ebook is hard to do, because you had Kindle, Kobo, and all these different ones.

The whole system was designed for the traditional way. And if you're in charge of these organizations, nobody in your organizations, except maybe your investors, is excited about the transition towards electronic. Plus, the costs are lower.

When I was there, you also had the issue of Apple and Amazon, with the pricing wars - so everyone sees the threat, but no one can have the solution. And I don't think the solution is going to come internally.

Len: And just to continue with the pile-on for the unfortunate book publishing -

William: I have empathy for them, yeah.

Len: No, I know. I was listening to a podcast preparing for this, another interview you did, and you mentioned that, even the importance of the publishers brand is decreasing.

William: Oh yeah - nobody cares. think it was always pretty small. But it's like a movie, right? Before every movie, there's a long list of producers and movie studios - that's purely back-scratching for the industry. At the end of the day, nobody cares if it's Houghton who can offer self-published book. If there are any people who care, they're not really who you want to deal with anyways.

So these days, if you're a publisher - and I know this first-hand, because I've helped some people get published - if you go to a traditional publisher, they will say, "Well, you have to bring your marketing with you." Part of the proposal is saying, "I've got 20,000 people on my newsletter." Authors will hire, out of their own pocket, publicists. Not to mention, the cycle is very long and slow.

I had an author who was very prolific, a fiction writer, Rick Bass, and we had to push him back and hold him back, because it didn't fit the sales cycle of Houghton, to have a new book from him every year. We needed some space. Which is crazy, because he just wanted to put it out. But that's just the system that you're dealing with.

I'd say the number one thing though, that traditional publishers do wrong - is they've completely gutted the midlist. It used to be the case that every season, Houghton, Simon Schuster, pick your place - they have one or two books that they've paid millions of dollars for, that's sort of like their lead book. I remember Hillary Clinton's biography was one of them. A book like that, that everyone's heard of - like Barack Obama's, you use that as - everyone the company is excited around that. And you use that in negotiations with Barnes & Noble, which doesn't really exist anymore, as sort of the lead. And then you slowly go down the list of, if it's 40 books you're putting out that term, so everyone's anchored around that big book.

But you never make money on those books, because you pay a huge advance, you pay a seven-figure advance. That's just a cost of doing business, and it makes everyone internally feel good. And at the end of the day, it's not the editors. Editors are not judged on the return, the ROI. That's the messed up thing about the industry, if you have a business mind, which I do - that as an editor, you are incentivized to pay more. Because nobody judges you on the return on investment on your book. All that you can say is, "I'm the editor on Hillary Clinton's book." "Well, how are you the editor?" "Because I paid the most." "Well, how'd you pay the most?" "Because I convinced my publisher." So then agents say, "Oh, Will's a two million dollar guy now. He has up to a two million dollar budget," right?

And then usually I would leave every two or three years and bounce publishing houses. So by the time the book even comes out, I'm long gone. I guarantee you, no one is doing any accounting of all the costs of it.

Anyway, so that dynamic is messed up. But it's the midlist where all the money is made. So the mid list - that's mainly where I was focused as a younger editor at the time. That's when you take a chance on someone. That's when you pay $50,000, $100,000 - and then it sells like a million dollar book.

That's where they make all their money, that and the backlist. But they've gutted out the midlist, because it's expensive, and it's error prone. And all the people there still want to work on those big books. They want to buy the important books, like Philip Roth - we published him at Houghton. We paid a lot for his books, more than almost all of them sold. So you're left with the big books that you lose money on. You gut out the midlist, you gut out marketing and publicity - and it makes for a challenging environment. Still with fantastic people working in there, but at least for me, I said, "Well, I have options at this point, I'm still young - so I'm going to go see what else is out there."

Len: Thanks for that wonderful explanation, it's -

William: Don't get me going.

Len: No, it's great. One of the curious things - I mean, people can be romantic about anything, but there is a peculiar kind of romance around book publishing. Because publishing a book can be seen by people as elevating their social standing in a way that's kind of unique to book publishing, I think?

William: I always ask people, if they ask me for advice on book publishing, if they should self-publish or traditional publish, "What's your goal?" Most people, especially in - I'm curious, in your experience interviewing authors - most people's goal is to publish a book. It is not to make money, and furthermore they need hand-holding. And most people - despite all the things I've just said - will hear me say that, and they will still want to go with whatever press makes a big impression in their mind. If it's a technical press, if it's a fiction press.

So you can't really beat that out of people - and that's fine, it's easier to not self-publish. There's a lot of stuff you've got to do. Even with a great technology like Leanpub, there's a lot of steps you got to do. And if you need an editor to ride you to get things done, there's some advantage there - but it's almost impossible you'll make any real money off it. But that's fine, right? It's about an ego stroke, or it's a marketing expense for a consultant. These are the traditional reasons.

But for me, when I started publishing books - I was doing it thinking, "This will be my business." I also knew how the sausage was made, and there's no advances in technical book publishing, basically. So that's how I opted in.

Now, I'm in a position where, with the sales of my books, all the regular publishers approach me all the time, saying, "Why don't you come publish with us?" And it's like, "Well, I would love to." I always want to hear, I'm like, "Why do you think I would want to do that? Why would I go from 90-something percent to 30% for an already published book - where I've done all the work, I've done all the updates, I've done all the marketing?"

There's no value there. But I think there is value if you're just a professional programmer, and you need the hand holding, and you just want to get a book out. But for someone who's already along the way, the value proposition isn't there.

Len: Thanks for sharing that perspective. I actually have interviewed a couple of people who did have the romance beaten out of them. I remember one guy in particular - he was a technical book author. And he submitted to one of the big-name technical book publishers. And he got the acceptance email, and he's like, "I just went skipping out of the house, and I was on cloud nine." Fast forward a year, and it was a nightmare. What particularly frustrated him was the fact that the book was done, and they're like, "It's going to be six months until it comes out, because we've got to do our formatting and copy editing and stuff like that."

William: Yeah. And they print it overseas, so they can't print on demand.

Len: And he found that just incredibly heartbreaking.

Len: Because he was seeing the technology get older and older, as his book was not coming out. But the words were done, and the code samples were done. Everything was done.

And then he saw that behind the romance of the big name, and seeing your name on the shelf, which is an amazing thing - is this real actual business that isn't romantic, and doesn't necessarily always work very well. And no matter how well-meaning or well-intentioned people are, it can end up putting you in a bad place.

But, as you say, if you are just starting out, then getting a book published by a publisher that can help get you some respect, that you might not have otherwise got - is worth all the money in the world in a way, in the long run. And it's not necessarily for the particular royalties that you're going to get on a book, that you primarily get value out of it.

William: Right, yeah. I think one of the best technical book publishers is No Starch Press, who - I know some of the folks there. They have their contracts online, they're public. So you can go and look at those. But you should never write a book for money. Even though I did that, you should never assume that that's going to make money. And I think - this is probably an existential thing for Leanpub, and actually you guys are probably seeing this, because you have video courses - I often wonder, is the book format appropriate, certainly for framework books?

I've written three books on the Django web framework. Every nine months, a new version comes out. So it's bad enough for programming languages, where there's updates, but it's not a major thing, where it's every couple years. But every nine months - I mean, you simply couldn't publish that with a traditional publisher. If you notice actually, there's almost no Django books out there, partly because it updates all the time, people get burnt out, and peoplejust don't want to do the work.

But the other thing is that there is this price ceiling on books, where people don't want to pay more than $40 for a book. They'll pay $60, $80 for a video. And if you look at the amount of content in - I won't name names, but a two three hour video - that's 40, 50 pages worth of stuff. Like, my new book is almost 400 pages, right? It's sort of my fault for putting too much out there, but the value proposition is way off with books, just as a genre. I mean I love physical books. I often ask people - because I sell digital books, I sell Kindle, and I sell paperback, and I ask people, "Which do you prefer?" And I don't really see a strong split based on age - there's a lot of people who like the physical book, but there's a lot of people like updates too, so...

Len: It's really interesting. Normally we save this part of the conversation for near the end. But the view from 30,000 feet here, is that educating people is very important, and that more and more people are learning how to write software - how to program. Programming is becoming a more important part of our daily lives, and how programming is taught, how people learn about frameworks like Django, is actually a really important thing that drives our economy and our daily lives. The whole industry is trying to figure out what to do. We're still - I mean, programming and software have been around for decades and decades. But there's something about our current moment where things are changing, and there was a response.

One sort of response to this was MOOCs, for example - Massively Open Online Courses, which are largely video-based. And one of the things that Will's bringing up is that - and we've actually encountered this with people with Udemy courses, for example, that are heavily video-based. They're like, "Wait a minute. It takes me like 100 hours to shoot the course. And then it's going to change every year?"

There are certain subjects, like the history of Rome, where you're probably not going to have to re-shoot that course more than once every five years or so, and even then, you're being kind of precious about being up to date with the latest scholarship.

But there are other things where the video format, like Khan Academy and things like that, actually seems, at first glance, and for many people, is very useful in their first touch with it. When you're on the creation side, you realize how quickly things go out of - they're no longer current.

William: Yeah, the production cost is way higher than text.

Len: Yeah. And so, one solution to this is the ebook, and platforms like Leanpub, where you make it dead easy to update things. And to issue those updates - not only to all your existing readers, people who've already bought your book. But then, once your book is updated, all future readers have a fully-updated book. So the book remains, as long as you're doing the work to update the words, and the code - it remains current. And it's probably the case that the ebook format, is - if you're monetizing it, right? Otherwise you'll just have a blog or something like that, but, if you want to monetize it as a defined product, then an ebook - as long as it's got this in-progress, or easily updateable publishing side of it - then that's actually probably a really good solution.

But our courses are actually - so, Leanpub has a courses thing. And we spent a long time with some very sophisticated people developing this. It's interesting that when we say, "We've got courses," people often automatically think videos. But in our head - although, you can put videos in them, like you put them up on YouTube, and then you can have them in your Leanpub course - I was kind of naively surprised when people reacted that way. Because to me I was always thinking "text". And because, from our perspective, one of our hypotheses is that every technical book should actually have an [accompanying course].

Let's narrow it down. Every programming book should have an accompanying course that you can take. Because if you've already written a book, if you're the author of it - then turning it into a course is basically like, "Well, now let's create some exercises and assign some grades to the quizzes." And if you're a reader, you get to prove to yourself. But then with the certificate that you get at the end, you actually get to prove to other people [what you've learned].

So n the current state of affairs, you read a programming book, and then you tell people you did so. But if you've got an accompanying course, where someone could get a certificate, then they've got this social and professional proof that they've actually done it. So it actually increases the value of reading and going through the book, to the reader, to have an accompanying course that you can take. This is our theory.

William: I think your hypothesis is correct. I think it's an interesting time, because nobody's quite figured out what people want. And partly it's thinking about, what are the customer buckets? To me there's a very small number of people who can make money from out-of-pocket purchases by individuals who don't care about about accreditation. They just want to learn it and sort of prove it. Most of the money is some sort of accreditation thing, or it's a company account.

So this is the rise of, where now, LinkedIn, Pluralsight, and O'Reilly would be the three large ones - where a lot of companies will just have a subscription. I've been next to people, they're like, "Oh yeah, I can learn Django," like, "I've got a subscription." And there's 30 courses on Django, all from 30 different individual contributors, and I would say, no kind of quality control. But these people, these companies - it's easy to buy, right? They want a one-stop shop. Because the person who's in charge of professional development is HR - even in a tech company, it is not developers.

So while I would like the GitHub model, where they just give developers - I think it's $100 a month, and let them buy what they want with it, that would be great - quality would win out. But that's not how it works. Companies want to have control, and they want this accreditation.

So yeah, I don't know? I think you guys are on the right track. I mean, I find it almost - the disconnect between the value that's being added by technical book authors, and what they're receiving - I mean, I can see the email addresses of people I interact with and buy my books. It's undergrads at, pick all the top engineering schools in the US and globally. It's professors at these schools, it's career people who have been doing Python - in my case, have been doing Python for 10 years, but never done web development, and they're learning Django.

So the value is immense, but it does come down to, why is someone doing it? I think this is the problem MOOCs had. They came out with MOOCs, and it was like all these super educated people who were learning for fun - engineers. And guess what? That's not most people, right? Most people aren't taking artificial intelligence for fun at a graduate level. They need to learn Excel and get a check mark, so they can get a promotion at work. And that's what most MOOCs are finding, and that's why they're sort of transitioning away from that.

Same thing with books. Most people - as a developer, we assume everyone thinks the way we do. And most people are not lifelong learners. They're not really into this. They're just kind of doing what they need to do, and anyway, accreditation is easier to get when it proves something - when someone else pays for it, and when you have to do it.

I'm biased, because the people I deal with are the best students in the world. Because they've already chosen my stuff, and paid for it. So even when I teach in a classroom setting, it all comes down to like, who's the client?

Len: Speaking of lifelong learners, I'm going to use that as a very cheesy segue opportunity to get back to your career - so, you are there in the publishing industry, and you realize that it's not going in the direction you think it should - and you decide to get an MBA. And then I believe, you moved to San Francisco, and started working for a company there. Is that correct in the timeline?

William: Yes, that's right. I wanted to move to other side of the country, and move from a very traditional industry to a startup. While I was in business school, as I was leaving publishing - I noticed that we were spending thousands of dollars. Our marketing budget was just for someone to build a website for these authors' books. And I thought, "Well, I could learn that." So I actually learned that, and had a side business throughout business school, building websites for authors. So when I then applied to jobs, I wasn't a programmer, but I had some technical ability and I ended up joining -

I was fortunate enough to have a couple offers, and I chose by far the riskiest one. It was a small education startup in a room, one of the founders was still in college, and that was called Quizlet - which is now the largest education sites in the US. That was a whole separate story. But I was there for three years, and at the end of that was like, "Okay, now what do I do?" And I decided the one gaping hole in my background was being truly technical.

I could sort of build stuff, but I couldn't really build it. And all my MBA colleagues were raising, this was go-go time - so, raising money and hiring developers. I'd worked a lot on hiring out the initial team at Quizlet, and I didn't really want to spend two more years hiring out people. Because most startups fail, so I thought, "Well, I'll learn how to code for real. And then even if my startup fails, I've got another feather in my cap in terms of knowledge."

So I did that, and ahd a couple ups and downs with startups. One failed, another didn't do as well, another was acquired - it was the last one that was acquired. After that was acquired, was when I started writing the books.

Len: Were these all in the education space?

William: One of them was. The first one I did was a school rating site. This is the one I went off and did on my own, initially. So, competing with great schools. Because if you're moving, as I was - you want to know what's the deal with local schools. All the data is publicly available. I could go on and on about that.

So I built, I would say, a better product than Great Schools. But people don't really want ratings, they just think that they do. And the companies like Zillow and Trulia, at the time, were in a marketing war. The affiliate fees that they were paying were quite high. But then they decided to stop fighting, they merged. And Great Schools is a non-profit that does an okay job, and that's sort of enough for people.

In the two startups - after that, I taught at Williams College. And then had a little bit of space after this acquisition, and I had found learning how to program - because I came to it later in life, and I'm certainly not a genius, but I have a brain, and I found it the most frustrating thing I'd ever done in my life.

I largely came to the conclusion - it was because the resources for learning it were terrible. They just made no sense, and most programmers learned at such a young age that they'd just totally forgotten, had zero perspective on what it was like to be a learner.

Because when you're 10, or 13, or 14 - everything just seems normal, and you forget what you've learned. But I came to it as an adult - and I had seared into me, the pain points of learning. I basically had all these notes that I'd written for myself, just to not forget things with different frameworks. Django was one of several frameworks I worked with professionally, and I just happened to like Django the best. And so the first book I wrote, Django For Beginners, I put it up on a website, it was my own notes. And then that started really good traffic. And at some point I thought, "I'll make it a book. I mean, nobody can stop me."

Len: One of the things I heard you say - and I might get it slightly wrong - in an interview that I was listening to before this podcast, was that. endemic to programming culture, is often a lot of posturing about how smart you are? And even worse than posturing, sometimes people are fully convinced.

Now, I've got to say, personally - I'm a former investment banker, so I'm familiar with the phenomenon, but one particular manifestation of it is, people don't want to ask for help, because then that means you're not smart, and people will take the opportunity to represent you as not being smart. And it can often be an environment in which questions are answered aggressively, and where people will not go into detail. Because, again - that's not something that a really smart guy would do.

But on the flipside, in programming - because people often have an engineering mindset, they do kind of like helping. So there's this weird -

William: I'm trying remember where I said that comment. I mean, so I often think - because I came from a sports background, in business, and so I love the engineering mindset of helping, and not caring about anything other than working on the work. But there is - and this might be specific to the startup scene in San Francisco in 2010 onwards, when I was there, where you had a lot of people who were special, because they knew how to program. And you have companies like Google, where it's just completely tiered. Well, it used to be two tiers, now it's three tiers with the contract people. But if you're a programmer coming out of college, you made $100,000, and if you came in as an ad rep you made $50,000. And it just went from there.

So if you're young and impressionable, you feel like you have a superpower. This was before bootcamps came around. So you really only could learn programming if you - I'm going to generalize here, but if you basically had spent your teenage years with a computer and not playing sports, not doing these normal things - because you had to have spent that time to learn all these things, and so you just learned by osmosis and chat rooms. And so you didn't feel the pain of - there's no learning, there was no learning structure. You just sort of absorbed it. And you felt different and probably a little bit ostracized. And then you come to San Francisco, and you're like special. I was hiring developers right out of MIT and Stanford for more than I made as an Ivy League MBA, right?

That's partly why, again, I was like, "I've got a brain - I could learn how to program." And it hasn't gotten better. I mean, programmers are underpaid. So for the value they provide, even at Google, if you're getting paid mid-six figures, you're getting underpaid for the value you're providing to the company. But just because did a bootcamp, and now you make six figures - experience does matter. But in the programming field, experience is often not valued. I'm 38 now, so it's not like medicine, where you get older, or finance, right? People tend to, maybe not investment banking. I think in investment banking they like experience. But in tech - experience is sort of a dirty word, actually.

Len: I never made it to the upper echelons, but at the top it's all networks.

William: Oh, everything is sales.

Len: That's what you build up over time, is influence and people you can call upon, and things like that.

William: Right, well that's what I would tell my - there were a number of classmates in business school who had been engineers, specifically software engineers. And they loved the advanced modeling classes in finance. I was always telling them, "You need to go out for drinks with your classmates. The work we're doing in this first year class is more than you'll do at Goldman Sachs." I actually spent a summer as an investment banking analyst too, but -

Len: That's really interesting. If we ever meet in real life, we can have some beers over that kind of thing. That's an intense experience.

William: Yeah, so basically, I love engineers. And I did say that because I do see that posturing sometimes. But I think on the spectrum, it's less so than other industries. And that's one of the things I like about coding, is, at the end of the day, it's like - you can prove it, show it - or not. And generally, now that I have more experience, if someone comes across as super braggy to me - I mean, in the Django world, I know all the top people. Not a single one of them is braggy. They are modest to an incredible fault. So if I see someone who - as an engineer, who's bragging, that's an immediate red flag for me - and I think most other engineers. Whereas it's sort of a prerequisite sometimes in other fields. But in engineering that's like a "Huh? Well, the best people don't think they're the best, so not sure where you're getting that idea about yourself."

Len: And you then decided, at a certain point, that you wanted to make a go of a career teaching people and writing books about things like Django. What was your first step? Was it writing a book?

William: The first step was, I taught. At Williams College, I taught a web development course, actually with MeteorJS, which as a JavaScript framework. And I loved doing that. But as all adjuncts will know, you're paid nothing. You're paid nothing, and it's a lot of work. So it doesn't really work in a professional setting.

But I've always loved teaching. I mentored and tutored throughout school, and actually, after graduating, for a summer I taught middle school. So I've always had that in me. And you kind of have to, because there's no economic reason to teach. It doesn't make any sense. But I started putting my stuff online, on websites.

I had the site. And really I got community proofreading, because people would spot things, and add comments. It was a while before I turned that into a book. And then when I thought, "Oh, I'll make it a book," that's - I forget how I came across Leanpub. But I was used to the traditional way of using InDesign, and realized like, "Oh God, it's a lot of work to do this." And then when I saw Leanpub, I think it was one of the authors, an author I respected - I asked him, and he said he used Leanpub. That's how I came across your service. And then it was just like, "Wow, this is a total no-brainer. It makes everything so much easier." And there are some - what is it? OpenLibre - there are some open source options, but I found you guys provided a lot more value.

Len: And you, as I understand it - now we'll transition to the last part of the interview, where we talk sort of in the weeds about the self-publishing and how to be a self-published author. As I understand it, your approach is to use Leanpub to make the books and to update the books, but your primary sales channels are not the Leanpub bookstore?

William: Yes. Len, you can decide if you want to include this or not.

Len: Just to preface this. So, of course we would like it if everybody sold all their books and put all their effort on getting attention to their Leanpub book landing page, or your Leanpub profile page. But we welcome authors of all kinds, who might even have no intention whatsoever of selling their books on our bookstore. That's why we have subscription plans and things like, and we offer all kinds of features, like, output in PDF, output in EPUB, output in MOBI, output in Print-Ready PDF, so that you can use Leanpub, and we will love you very much if you never sell a book on our bookstore.

William: I actually had a lot of emails with Peter, which I give him credit for - actually, I think you too, maybe? Now that I think of your name. So, the royalty change. You guys had that big one page thing, and the royalty rate changed from 95% to - what is it? 90% or 80%? And then you were like, "Okay, but we're going to grandfather it in." And then you're like, "No actually, we're just going to go across the board." And so that's when I switched to Gumroad predominantly. Because they pay more, they pay every week - and they give me the email addresses. And those are three things Leanpub. at the time, didn't. I'm not here to slag on you guys.

Len: No, that's perfect, I'm glad to have a frank discussion about it. So, the way it worked, was Leanpub - from its inception, paid 90% minus 50 cents per transaction.

And then we decided at one point that, for the sake of sustaining Leanpub in the long term, 80% was a better model than 90% minus 50 cents. We were very trepidatious when we did this. And what we did was, we grandfathered in the old books. So if you already had published a book, and you were already earning 90% minus 50 cents - we left you with that royalty structure.

But then we decided - no, we want just all books to be 80%. And we knew some people would decide that that, plus other things, like, say for example in the case of Gumroad, weekly payments, which - and just to get into the business details of things like that. So, for example, one of the reasons we don't do weekly payments, is because we have a 45=day refund yeah period, which is a very important part of how we position ourselves, and how we brand ourselves. It's that you can buy a Leanpub book - and if you don't like it, you can return it with a couple of clicks. We give you 45 days to do that. And the reason for that, is that Leanpub is focused on optimizing the self-publishing process for in-progress published books.

It just wouldn't fit our business model to have a refund window that was much shorter than 45 days. Because then we're saying to authors - in order to prove to people that you're still working on your book, you have to sort of publish a new chapter every month, or something like that.

William: Oh, huh.

Len: That's one of the reasons for the 45 days. And the emails thing - so, when someone buys a Leanpub book, or they sign up to be informed about when one is published - they actually do have the opportunity to share their email address with the author. But we don't make it mandatory, and believe - we've had discussions with people who were much less friendly about it than you are.

William: Oh, I felt like I wasn't that friendly. I feel bad, but I gave it to you straight.

Len: No -

William: I understand - emails are a hard thing on both ends for stuff. Well I mean, I'll say - one thing you guys do do, which I really like, is the ability to pay more. Because that's something I had heard from other authors. It doesn't happen all the time, but it does happen. And actually, as a feedback for you all - I would love to be able to send a personal thanks to someone who does that. I don't have any way - it’s anonymous to me. I’ve had some people who spent $100 on my book. I would love to send them a thanks, but I have no way of doing that.

Len: Just for everyone listening - another thing that we do that isn't very common, is we have a variable pricing model, which means the author sets a minimum price for their book, and a suggested price for their book. And so when someone goes to a Leanpub book landing page, there's this pricing slider that's set at the suggested price. And you can move it to the left, all the way down to the minimum price - or you can move it to the right, and you can pay more than you have to for the book. And this actually does happen. It's something that I think a lot of industry stalwarts find quite - or even just normal cynical people - find surprising. But actually, giving the author an opportunity to send a thank you message is a really good feature suggestion, I don't think we've had that before.

But one thing we have had before that's related to this, and many people have asked for it over the years - and we do intend to do it someday - is basically, a tip jar. Because often what someone does, is they might buy a book - the minimum price might even be free, and then they read it, and they're like, "Oh, I really wish -" or, they paid five bucks for it, and they're like, "You know what? This is actually worth 20 bucks to me, what can I do?" Currently, our sort of hack is to buy a new copy of the book, and then just archive one of the two copies in your library - which is what we recommend.

William: Oh, interesting.

Len: But one thing - now that you've mentioned this - when we do implement the tip jar, we'll definitely think about how we can facilitate a thank you from the author for that. Because, especially if someone's directly going out of their way to come back and pay again - that's a very good idea. Thanks for that suggestion.

William: I think my case is specific. One of the things that Leanpub does do, is provide a platform. So beyond the book creation - which I use and is by far the best. There is that discovery aspect. So I still have sales on Leanpub, from people just coming to Leanpub. I mean, meaningful sales. And there's the Shelf feature for advertising, which I did. I got the yearly thing, and that's been helpful.

In my case - because I'm focusing currently on this full time, and I have personal sites and I have a lot of SEO - I have seven figure annual traffic to my personal site, that's not common. So, for that reason, as a content creator, I often think about it. I often ask people, like, "How did you find my work?" Someone - did they go directly to Amazon and stay within that world? Are they at my site and then they read a blog post, and they go to Leanpub? Or they go somewhere else, they go to Amazon. As a creator, I would love to know. Because that would be helpful.

And this is another thing, that "just the book" paradigm - I increasingly wonder if it's the best format for - certainly framework books, versus a website. Where people log in, and you can track better. But then that's a whole ton of work. And for me as a content creator - I want to create content, not do all this other stuff.

Actually, one point I want to make, is that I think - the reason why people don't create technical content, is you need three things to do it. You need to know how to code, you need to know how to teach - and then you need to know how to market.

Almost nobody has all three; they certainly don't have the third one. And if they have the first two, generally they can do consulting or other things that pays way better and is more fun. So I'm sure for you guys as well, you pump out a great feature - sometimes it's hard to understand how important marketing is. But the more you do any business, you go, "Oh yeah," like marketing. For me, I would love to write ten more books. I've got ten more planned. But I should be spending my time promoting the three that I have.

Len: Thank you very much for saying that - that's really excellent advice, and a really excellent way of putting it. There's different types of work that you have to do, and marketing is not - it's not being lazy or whatever, this is just another phase of the project - and a bigger part of what whatever it is that you're up to. People who want to create stuff, and want to learn stuff, and want to teach stuff - find it hard to sort of put all those tools down, and just go do the marketing.

William: It doesn't feel good, and you can't track it easily.

Len: But you do need to understand that there will be periods of time in your campaign, let's call it, when you're doing very little of the learning and the teaching and the writing, and you're doing a lot of the promoting.

In that note - so I know that you have also experimented with selling on Amazon as well.

William: Yes, it's a very meaningful sales channel for me. And I use the create PDF feature that you guys have.

Len: For selling print books on Amazon?

William: For selling print books. So, Amazon has made a lot of changes recently. And actually I've emailed with your team, that's been receptive to - they switched over from - now they're doing KDP, they're doing their own self-publishing thing. So the format sizes have changed. It used to be that you couldn't do 7" by 9", which is the technical standard book size. It was only 8" and a half by 11". But yeah, so I can create the files. And because everything on Amazon is print-on-demand, my books are always up to date. Which is fantastic.

Len: And do you also sell ebooks through Amazon?

William: I do now. I sell Kindle there. The hard thing about that - so the royalty rate really matters. And this is something that doesn't matter to readers - but as a creator, it's really a kick in the nuts. Because basically a print book is 60% minus printing costs. That works out to about 50%. So a $40 book, you get $20. For a Kindle book under $9.99, you get 70%, minus the transmission fee - which is totally bogus. So if you have any images in your book, as I do - that's another like dollar they're going to subtract out of it.

Len: What?

William: Yeah, they charge a transmission fee for the network. So for example, if I charged $9.99 for my book - it wouldn't be that I get $7 dollars, it's more like $5.50 - because I have images in it. Now anything over $9.99, they switch to 35%. So on a $40 book, 35%. What is that? Like $14. So I make $20 on a paperback book that is print-on-demand, shipped - and no returns. Whereas a Kindle book, which has returns - and actually there's quite a lot of them, I make $14 on. So going forward, do I want to do Kindle? I kind of don't. But for now I'm just putting it out there.

And another thing too - unlike Leanpub, I've emailed with Amazon. It is possible to do updates, but it is incredibly tricky and not designed to do updates. So if you have a book that stays up to date, like mine - again - I recommend they go like Leanpub or another ebook route, where they will get the updates - than to go through Kindle itself.

Len: I did not know about that transmission fee - that's incredible.

William: It's lovely.

Len: But for those listening who might not know, Amazon discourages sales of ebooks for more than $9.99. And they do this by paying you a lower royalty rate when you cross that threshold.

William: Yes, a $20 book makes the same as a $10 book.

Len: Yeah. I mean, you would know a lot about - more about this than me. But there is a deep fight in there about the concept of what the value of a book is. We could talk about this for a long time. So, someone would ask, why would someone price an ebook at $15, when they could make more for $9.99? When they would actually make more money if they sold it -

William: Oh this is another good point, yeah.

Len: And the reason is that, the big publishing companies didn't want people to think of books as being worth $9.99. They wanted to think of them as being worth $15.99, or whatever. And so a lot of publishing companies would actually set a higher price of dinging the customer more than they would otherwise, and get less themselves from that sale, because they were trying to do some high-level positioning around what people's sense of what a book should cost, would be.

William: Right - and if you publish on Amazon, as I do - you are not allowed to offer it for less anywhere else, or they have the right to yank your book.

Len: Yeah.

William: So I'm not allowed. If they find it, they will - and they're pretty good at finding it, so my book is the same price. It limits your pricing.

On the other hand - I mean it's easy to demonize Amazon, and I've done plenty of it. If you think about it as a self-published author, it is astounding that I can send a file - in seven countries currently, it will print on demand, handle everything for me, and just give me a check. And then 13 countries for Kindle, that's pretty amazing.

Len: Yeah.

William: But there is this tension in the format of all books, and then - especially technology books, with updates and all these other things.

Len: Amazon - just to be clear, it's an amazing company in a lot of different ways. And like, Leanpub probably wouldn't exist if it had been for Kindle, for example - the device, I mean, and the normalization of the reading of ebooks, and things like that. But this $9.99 pricing thing comes out of the non-technical book world.

William: Yes, like romance fiction.

Len: In the non-educational book world. With a technical book, one of the reasons technical books - by tech, we mean programming and things like that. One of the reasons they can fetch a higher price than other books can, is because the person who reads it makes more money after they read it. Or it saves time. Which people, professionals often equate with money, right? So if I can say to you, "Hey, buy my book for $40." They're like, "$40 sounds like a lot for a book." You're like, "You can now bill yourself out at a higher level as a consultant." Or, "Now you can get work done in an hour that would have taken you two before." Most professionals will be like, "I'd give you $400 for that."

William: Right, it's - if I save you five hours, what is your billing rate.

As a teacher, basically you're selling to intermediate developers or professional developers who are in a time crunch. Beginners won't pay for anything, because they don't know anything, they don't value stuff - so they're kind of out. You can use them for SEO. I mean, I write tons of stuff for beginners. I actually prefer total beginners, but they're very hard to monetize.

Experts are very much like, "read the manual" types. It's someone who's an intermediate leveling up developer, or who's new to the technology or framework. Or it's someone who-- and I think there's more of them - who knows what their time is worth, and will say. "Okay, I trust this author." And, for me - I buy books and resources all the time, because I value my time - and this stuff is hard. But you can't help people who don't want to be helped. That's sort of the hard thing as a content creator. It's not really useful to bemoan the state of who will purchase content.

Len: Speaking of wanting to be helped, that leads me to the last question that I always like to ask people on this podcast. So, bracketing our royalty rate, and how often we pay people, and making people give their email address up in order to get a product - if there was one thing we could change for you - like say build for you, or one thing we could fix for you - what would you ask us to do?

William: That is a really good question. I'm tempted to say one of two things. One is around the market side of Leanpub- promoting books, other than the Shelf, if there were more targeted advertising or marketing where, maybe someone bought a Python book, or maybe someone bought another Django book? Is there a way that they, on the Leanpub site, or through some other mechanism,can be told, "Hey, maybe you'd like you like -? You liked that book, maybe you'd like something else?" That would be something that would probably help sales in general - and certainly as an author, would have value to me that I would pay for.

On the creation side - so my books, using Leanpub - I've only once had a complaint on the layout of my books. I don't know the answer to this, but sometimes because of text, and especially images - there are gaps on the print books. I don't know what the answer to that is? Maybe if there was some custom way I could go in and fix - an image or spacing here? But sometimes in some of my books, there is spacing issues where, largely it's like - oh, there's three paragraphs left, but an image is six paragraphs long. So it just bumps down. And that wouldn't happen on a professionally-designed book, but the professionally-designed book couldn't be updated all the time. So it's a tension I'm willing to take. I don't know if there's a way to spot or give an option to clean that up, but that would be something nice.

Len: Thanks very much for both of those suggestions. The first one is something that we're working on.

William: Okay.

Len: And the second one is - if you come across that issue in one of your books, if you could send us = I guess if it's a print book, you might have to send us like a picture of it or something like that. But if you could -

William: Well it's in the PDF, right? It's in the Print-Ready PDF.

Len: Print ready PDF, okay. If you could--

William: Well it would be, right? Of course it is, because it's just -

Len: Yeah, that's right. You're exactly right. If you could point us to an example of that, then obviously we have the underlying manuscript as well. So we can then look - I can talk to my colleague Scott about it, who's the expert on this kind of thing. So if you could just flick us an email or something like that, pointing us in the right place - we'll definitely look at that, because that's the kind of thing we like to keep on top of.

William: Okay.

Len: The more detailed the example, the better, so -

William: Sure. Well, and I know from experience, I've had other things that I've emailed your team about, and I've always gotten - actually I recognize Scott's name as well as yours and Peter's. So to the listeners, they really do listen. It's sort of like, when I wrote the slightly angry letter back in the day - the reason why I'm still using you guys, is because you engaged with me and responded. And I know from working at startups, that when someone is unhappy, and takes the time to write you - if you acknowledge them and answer their questions, they will then become your fiercest advocates. Because they're basically - writing the letter says, "I want you to make this better." Not, "I've given up." So you must have that as well, right? Like when you're dealing with customers, it's always - when they're really angry - I always try to think, "This is a really good thing. Because there's something I can do to make them happy." They want to be convinced to stay.

Len: What I would say is, first of all, we don't enjoy getting angry letters. But - and I actually didn't remember that you'd -

William: I can send it to you after this. I don't know if it matters, but I remember it.

Len: That's okay. But we do like it when people are passionate. And one particular thing about being - to circle back - to being in the book business. A book is something that someone spends a lot of time on, and it's very important to them, usually in a lot of different ways. Like it might be, "This is how I'm going to get ahead in my career." It might be, "This is going to be my platform for getting to give conference talks." It might be, "This is just something I really care about." And so, we maybe face a little bit more passion than people do in other businesses, or a different kind of passion. Because someone's like, "I've spent 200 hours on this, and I told my grandma about it - and now it came out, and it looks bad or it's broken," or something like that. Or, "I'm on a deadline," and things like that.

So we welcome feedback, we welcome impassioned feedback. And if we do something that makes you mad, we do want to hear that. And when someone takes the time to - I mean, if it's just a "fuck you," then like that's not useful.

William: I was going to say, if it's concrete. Yeah.

Len: If it's a detailed argument. And particular - maybe one of the reasons I didn't, when you brought that up, it didn't have any kind of emotional residue for me, was because, when we make big changes like that, we know there's going to be a reaction, an if someone comes back at us at length - like yours, and they're smart, and they know what they're doing - that’s really important to us. Because one thing - I'm not saying we're going to reverse any of these decisions, but one thing we're always open to, is what the future’s going to look like. And getting feedback - whether it's happy or not, is really important to us, so yeah - that's good.

William: Well it's a strength of a company, because you always want to know what people think and, again, at least for me - when I do give feedback, I find that almost every tech company - even if it's the top person, I will get a response. And usually a pretty good one if it's some sort of detailed - it's not just a rage thing, it's, "I think this is off in some way, and this is why." Yeah, so it's a kudos to you guys that -

Len: Well thanks for sticking with us, and thanks for taking the time to do this interview. I really appreciate it - and thanks for continuing to be a Leanpub author.

William: Thanks so much. I don't get to talk about publishing with anyone anymore - it is brings me back to my old days, so it's fun.

Len: Thanks.

And thanks, as always, to all of you for listening to the Frontmatter podcast. If you like what you heard, please rate and review the podcast wherever you found it. And if you'd like to be a Leanpub author, please visit our website at Thanks.

Podcast info & credits
  • Published on July 23rd, 2019
  • Interview by Len Epp on July 2nd, 2019
  • Transcribed by Alys McDonough