An interview with Jay Hoffmann
  • January 25th, 2019

Jay Hoffmann, Author of The History of the Web, Volume I

1 H 25 MIN
In this Episode

Jay Hoffmann is the author of the Leanpub book The History of the Web, Volume I. In this interview, Leanpub co-founder Len Epp talks with Jay about his background and career, starting and maintaining a popular newsletter, his book, the history of the web, the challenges the web presents to historians, some of the more interesting stories that he's researched, and at the end, they talk a little bit about his experience self-publishing.

This interview was recorded on January 16, 2018.

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

This interview has been edited for conciseness and clarity.


The History of the Web, Volume I by Jay Hoffmann

Len: Hi, I'm Len Epp from Leanpub, and in this Frontmatter Podcast, I'll be interviewing Jay Hoffman.

Based in New York, by day Jay is lead developer at Reaktiv Studios, an Agile VIP WordPress studio that is one of just thirteen VIP service partners globally.

Jay is the author of the book The History of the Web, Volume I, which you can find at The book is based on Jay's popular History of the Web newsletter, which is based on years of his research into, and passion for, the web, which presents particular challenges to historians, particularly because of its rapidly changing, and in many ways ephemeral nature.

You can follow Jay on Twitter @jay_hoffman, and you can sign up for his newsletter at

In this interview, we're going to talk about Jay's background and career, starting and maintaining a popular newsletter, his book. and most importantly of course, the history of the web, and the challenges the web presents to historians, some of the more interesting stories that he's researched, and at the end, we'll talk a little bit about his experience self-publishing.

So, thank you Jay for being on the Leanpub Frontmatter Podcast.

Jay: Thank you for having me.

Len: I always like to start these interviews by asking people for their origin story, so I was wondering if you could talk a little bit about where you grew up and how you first became interested in computers?

Jay: I grew up in New York, not far from where I live right now. A little bit far outside of New York City, in a place called Long Island.

Computers came really early for me. I was playing around with computers in middle school and starting to build my own back when that was a popular thing to do - or customize your own computer. I think I actually came into it from the realm of film, which has always been an interest of mine. It's something I studied a little bit.

In my high school there was a film class. It was very small, but we had a few computers. That's where I learned animation. And from the animations, I created my first website to put those out, and people loved it.

Then I went to college, and I needed some money. A few people were able to pay me to make their websites, and then more of that. I graduated college and just kept going.

It's interesting, because I think when I started, it wasn't a career. It was something people were starting to do, but I had no awareness that it was a full-time career.

By the time I got out of college, it was actually starting to become a really refined profession. And so I've been doing that for a little over a decade now.

Len: What was your first paid job working on the web?

Jay: My first job ever was at Sesame Street - or Sesame Workshop, which is the non-profit that produces Sesame Street and a couple of other things. They actually hired me really early on to work in the marketing department. And I grew there. I got to work with this really great, small team that was tailored towards adults, which is obviously not-- I mean that's not the most common Sesame Street use case, but it was fun. We built corporate sites, but also a lot of fun experiments over the years. So that's where I started.

After that, I worked at Random House, the publishing house. And for the last few years, it's been Reaktiv Studios - which is a really, really small, lean development agency - and I've been loving it.

Len: Since it's in the publishing industry, it's of course a particular interest to me. What did you do for Random House?

Jay: They maintain a few reader-focused blogs. My job was basically to maintain those. They were mostly on WordPress, and so a lot of my work was maintaining and developing those sites, and creating new features and a couple of more experimental things.

Len: This is probably jumping ahead a little bit in terms of timelines, but you worked for a company that produced television shows, and you worked for a company that produced books - but not on things that had to do with distributing the main content, specifically, over the web.

I'm curious - did you get the sense at either company that they were concerned that the web was a threat to their core business, when they started getting into doing these other things?

Jay: I've been really fortunate to work with people that have accepted the web as a foregone conclusion, before I even started there. I think Sesame Street in particular is very, very good about embracing the digital generation, and the way that things are distributed now. They have a core mission, which is to reach as many kids as possible. And so they look at something like YouTube or digital platforms or digital experiments as a way of doing that, rather than a hindrance. Their business model is - I mean, they are a non-profit. So I think they really embrace that.

With Random House, I happened to work with a group of people where that was our job - to explore the fringes of the web and try to figure out how we can reach people in different ways.

Len: Just going back in time a little bit - in your story that you politely glossed over, I think, the humorous nature of your first adventure on the web. I've interviewed a couple of people on this podcast, who got their start in mischief. Particularly in school, and so I was wondering if you wouldn't mind sharing your experience with that.

Jay: It's funny, because I've talked to quite a few people about their own origin stories, and I think the most common thing you hear is a band website. After that, it's fan sites or experimental sites. Mine was in that vein. One of my first few sites was my band's website, which is now defunct - thankfully.

Before that, the very first website I ever did was in high school. There was a policy that was instituted by our principal that said nobody could wear hoodies during school. Really, I'm still very unclear about why that was the case. But I created -

Len: Just to interject - people can't see, but Jay's wearing a hoodie right now. Still protesting years later.

Jay: Who knew that one day I would get a job where I could do it all the time?

That was the school policy. So I made a flash animation, it was 15 seconds or 30 seconds, that poked fun at the whole idea. I created the website so that I could tell people, "Hey, go to this website and view this animation." And then from there, I created - this is like in the Newgrounds times, it was inspired by that and a few games and stuff like that.

Len: I think I'll have some questions for you about Flash in the future, and I imagine many people listening might not have even heard of it, which is actually going to be hopefully a theme that we can touch on a bit in this podcast.

But before we get to the subject of the web and its history, I wanted to ask you a little bit about WordPress. WordPress is something where I think a lot of people really don't quite grasp its reach. I was wondering if you could explain a little bit about some of the ways that WordPress is used that people might not be familiar with.

Jay: Some of the biggest confusion around WordPress is probably that they're really two entities, when you're dealing with it - and is generally how you can think about it. is a site builder in the vein of Squarespace or Wix, something like that, if you've heard of it - it lets you create your own website, buy a domain, all that stuff. It is a service that is run by the creator of the software, WordPress, which is hosted on, which anybody - it's open source, which means anybody can download it, customise it. There's a whole ecosystem around it. That is the more common use of WordPress. And current estimates say about 25% to 30% of the web actually runs on the WordPress server or [other] software.

So it's a huge chunk of the web. If you spend any time in the web development world, it's definitely something that you're going to encounter - it provides a lot of tools for not only creating sites, but at this point it's being used for applications and all sorts of different things.

At my agency, we get to do lots of very, very advanced things with WordPress, but the whole idea behind it is - you and me, anybody can download it, and set up your website. It's got what's called "The famous five minute install." You can get it up and running in no time. Its core principle, I think, is really to democratize publishing. Which it's been fairly successful with doing over the years.

Len: I think we might talk a little bit about that subject in a bit as well.

Just before we move onto that, can you give an example of an advanced use of WordPress that a studio like yours would work on?

Jay: Sure. There's this whole thought process that goes along with WordPress, that it's really only for simple blogs or simple sites. What we really create is entire platforms or applications using the software. So it really runs the gamut.

Len: Did the New York Times run on WordPress, or does it still? Do you know?

Jay: That's a good question. A good chunk of it does. I'm not too sure - it's got a lot of different components to it. [Here is a link with some relevant information - eds.]

Len: So, you started the History of the Web newsletter - I believe in early 2017. I wanted to ask you, what inspired you to begin the project?

Jay: This goes back a while. I was a history major in college, and I wrote a few thesis papers, and really got into research and what that takes. It's always been an interest of mine, generally.

When I got out of college, I poked around the history of the web, just as a way of exploring my own passion. It's a very interesting story. It's fascinating to me, because it's so young. I mean, we're still 30 years, or under 30 years, in terms of how long the web has been around. And yet, the sand is constantly shifting beneath our feet and we're losing things all the time.

So I started to just research things and compile a few notes. I talked to a couple of professors and web practitioners and people that have been around for a long time.

I increasingly got the sense that nobody was really doing much research about it. I mean, there's a couple of efforts here and there, but there wasn't any concerted effort that I could see.

And so, I thought about a few different ideas. A book actually early on was an idea that I wanted to explore, but I decided for time reasons, and also just to get something out, and to start exploring the question of - is anybody else interested in what I'm interested in? Which is, I think a very common question.

I just put out a newsletter, and I said, "Look, I'm going to do the research. I'm going to chunk up that research, and each week I'll pull something out and I'll tell a cool story - and if you like it, subscribe". That's what I've been doing for the last couple of years.

I'm in the process of thinking through a few different ways to expand that. But that's generally been how I came to it. The research part has been going on for a decade. The writing part of it has been the last couple of years.

Len: Thanks very much for that great explanation. It leads me to a couple of questions, and it's hard for me to know which to ask in advance, because the challenge as a historian of dealing with something like the internet is, I think in many ways - unique.

But I guess before I can talk to you about that, I need to ask you about - let's say, what's the difference between the internet and the World Wide Web?

Jay: The internet dates back to more like the 70s, well, early 80s. It actually started as a government research project. I won't get into all the nerdy particulars, but it basically it is the pipes that run between computers. It is the way in which computers connect to one another. It is a collection of different technologies that allow computers to talk to one another.

The web came a little bit laters - really early 90s, late 80s. It was built on top of the internet. It is a layer on top of the internet that makes it easier for me and you to connect to the internet and, more importantly, and I think this is something we'll definitely talk about - publish on the internet.

There's a few different components to the web, that allow it to do that. But I think what's really interesting is that, when it first came out, it was not so clear that the web was going to be the way that everybody connects to the internet. Which is mostly true these days. There were a lot of competing protocols, technologies that were emerging at the time that really had some features that the web didn't. But the web had some early advantages that let it overtake it.

Len: You write on your website, and I'm just going to do a little quote here - "The web's history is fairly unique. It is at once extremely ephemeral and still nascent. The web was born as a document based medium. One of the features of this medium was that documents can disappear, and they often do. So even as the web rapidly advances, pieces of it get lost over time."

There's a couple of interesting threads there to pull on, one of which is the sense that the web was born as a document based medium, invented by Tim Berners-Lee at CERN. I was wondering if you could just take a couple of minutes to tell that story?

Jay: CERN, for those that don't know, they're the folks that created the Large Hadron Collider that was finished, I think, a few years ago? They are a physics lab, essentially, based in Switzerland.

Tim Berners-Lee worked there. He was a computer scientist - it's an interesting story, because he had this dream of the web really early on. I think by the mid-80s, it was something that he wanted to do. He wanted basically a way for anybody to read something or publish something on the internet. That was his goal.

But he knew that CERN wasn't going to just approve a random project. They're very researched based, R&D based. They'll enable their employees to explore things. So what he did instead was, he pitched them a project that allowed everybody in CERN to publish their documentation or to publish their academic papers in a way that was indexable, searchable, easily accessed by anybody on any computer - the biggest problem being that somebody over here might have a Windows machine, someone over here might have a Linux machine, etc. And connecting those computers was a problem.

So the web was actually first created as a way for a bunch of academics to share documents with one another - essentially a phone book with a few advanced listings on it. And that was how Tim Berners-Lee snuck the idea of the web into CERN.

Eventually, a few years later, he convinced CERN - and this is a, huge decision, it was landmark in why we all use the web - he convinced CERN to release it into the public domain. Which means nobody owns the web. The web owns the web, and that's what allowed it to spread.

Len: It's really interesting that it began - the excuse for it was a phone book, but the reason for it was a library, which is something that I think people who we don't really use anything other than our phones for phoning anymore - we don't have separate phone books. And most of use the web for all kinds of things besides storing documents or reading something that's formally understood to be distinct as the document. And so it's just very interesting that it had that beginning.

So with that stage set, as a historian, how do you go about finding the information that you use as the basis of your newsletter and the content for your book?

Jay: I did research papers that covered a period of time from 500 years ago, thousands of years ago. Things like that. I have a couple of advantages - the first being that basically everything I need is digital. It's not all findable, because - again, obviously a lot of things have just disappeared over time, although there are ways around that. So that's one advantage I have, is that I can do it from my computer at home.

The other advantage being that most of the people that started the web are still alive today, and really, really excited about the web. So I managed to reach out and talk to a lot of people about that, and they've given me a bit of a perspective on what things were like early on, and how things have evolved over time.

The trick for me is really getting the facts right. There's a lot of opinions. There's not really like a historical record to speak of. It's really going through people's opinions, going through the way that people saw the web - with today's perspective, and removing that modern perspective and trying to put that new way of thinking on.

Len: When it was released to the public by CERN, who were the first people to pick up on the web and start using it?

Jay: The earliest examples of websites that you'd find were non-commercial, academic usage. So you saw a lot of universities just publish a website which was their own phone book. You saw some government agency start to publish public records, and things like that. They're always looking for new ways to store that. So they would get on the web.

But I would say, in the first couple of years, what you started to see was people just experimenting a lot. Nobody really knew what we could do and what was possible with the web.

There was like a web comic that really early on. It was an academic, it was a professor somewhere - but he also happened to be a cartoonist. And he threw his web comic up on the web and people really liked that. And then somebody experimented with a magazine. And other people experimented with early animations, and things like that.

By 1995 or so, you started to see web designs and web experiments. There was this sense of this indie web, which eventually got glossed over by a real commercialization boom. Which is where the dot com era - I'm sure we can talk about it if you'd like?

Len: Yes, definitely. It's interesting, it was, at least for me, quite a challenge to try to think about how to structure this interview, and maybe that's been reflected in a bit of the meandering so far. Because -

Jay: How I like it.

Len: There's just so much to try and grasp. And so I guess, for the next part of the interview, I'd like to ask about various themes and not just follow random issues through the temporal timeline. Rather, I'll ask about different themes through their timelines.

So, in the beginning was the word. The internet was about text and it was about looking at texts and communicating with text.

There's so many things that we just take for granted, which is I guess, what I'm trying to get at in this part of the interview. When was the first image viewable on the web?

Jay: There was a lot of conversation about how media in general should be handled. There was this understanding among the innovators of the web that, if it was going to go anywhere, media was going to be a big component of that. And really the reason you didn't see like a lot of images and video early on was bandwidth more than anything else. The imagination was there, just how that was going to be represented was a little bit of a in the air question.

You started to see images pretty early on, but the way that it worked was you would actually click it and it would open in a new window. So the first time you ever saw an inline image, which - again, is something we see - I don't know? a million times a day, and we never even think about - is with the browser called Mosaic, which changed everything. It eventually became Netscape Navigator, which is probably something a lot of people are familiar with.

Netscape Navigator was the first commercial browser, meaning it was the first browser to be sold. All the browsers before that were basically experiments that were cool but very hard to set up. You needed to have technical know-how to download it. And you had to run a few commands, even just to get it installed on your computer. And then Mosaic came around, and it was like - you download it, install it, you can run it on any computer. It's got inline images, which is insane. It's got colors, it's got all sorts of great things. And then that's where people got a lot of inspiration to start experimenting with the different mediums. So that's in the mid-90s, you're starting to see that.

Len: And did GIFs appear around that time, and is that how the word is pronounced? [Len pronounced it with a hard G - eds.]

Jay: Yeah, I say, "GIFs." I think canonically we can say that. It's funny because it was used because it's a lightweight format. You can create a GIF, and it's incredibly small-sized. That's why people used it, and then they were like, "Hey, you can make things move with it." If you were a web designer, a developer in the early days, you probably remember the "under construction" GIFs and, all sorts of flashing tags and things like that.

Len: I'm curious about audio. I guess there's two parts to that. One is downloading it from the web, and the other is listening to it on the web. Could people use Mosaic or Netscape to listen to music?

Jay: Download it, yes. One of the earliest websites was called The Internet Underground Music Archive, and it actually started as an FTP server in the 80s. But once they saw the web - they were enamored with it, and they moved all their files to the web. And what it basically was, was any band in the world could send them files, they would encode those files in such a way that they can be downloaded fairly easily on the web. And then they would put them up for free. It was just a way to trade basically underground mix tapes. Lots of cool bands were coming on and starting out there. That was definitely around.

Len: I had an interesting web experience. I was in Delhi in 1995, and a friend of mine's uncle had a connection at Microsoft. So I got to be at the Indian formal launch of Microsoft Windows 95.

Jay: Wow. With Internet Explorer. I remember being totally awestruck by the fact that you could click play and watch a Weezer video on the computer. Do you have an idea of when people first could watch video on the web?

Jay: On the web? Yeah. There were early attempts to try. You can make downloads available. If anybody remembers the early days of the web - lets say before broadband, you would have to sit there for a while to download something. But there was a lot more experiments with interactivity and animation,like motion on the web, in a way that wasn't strictly video. The idea of being that - I think a lot of people, even early on saw the web, saw it was an interactive medium. It was something that, when you click something, if you have this visceral response - that was eye-opening for a lot of people.

You would click something and the button bounced on the page, and it was like, "Wow." You'd just never seen anything like that. There were a lot of experiments with motion, with little tiny bits of interactivity. Actually in the mid to late 90s, you probably saw more experiments with things flashing around the page and jumping in, and all sorts of craziness, than you do now.

Web design is a little bit more refined and constrained now. I think users tend to like that when they're just trying to get something done. But in the early days, you can make a text bounce all around - if you could do that, it was like a way of showing off. Like, "Hey, look at this cool thing my website can do."

Len: You're reminding me. I just got an email in Comic Sans yesterday. It's funny, we all make fun of Comic Sans now. But you're reminding me that like there was this playfulness at the beginning of the web that was pervasive.

People were, as you say, just so excited to be able to click things and make things happen. I have a philosopher friend who talks about how one of the reasons people love guns so much is that they allow you to do something at a distance. And there's just something really primal about that, being able to exert your influence on this thing - is one of the things that makes the web compelling.

Jay: For me, that's what's the most fascinating part of the web. I think a lot of times in the narrative that I'm telling, that my perspective and my opinion on that, probably leaks out. Because I really do see the turn of the web towards commercialization, as maybe something being lost. I try not to color my entries too much with that, but for me that early experimentation and that early innovation was incredible. It really felt like there were no limits at that time. Like really, we can do anything with this new tool. Len: That leads me to the next theme I'd like to cover. So, now that we've very briefly covered formats that we'd be familiar with on the web, I wanted to talk about commerce.

First of all, you actually mentioned this briefly. It used to be that in order to use the web as a normal, non-technical person, you had to go and literally put on your coat, put on your shoes and go to the store and buy a piece of cardboard shrink-wrapped with a disc in it, that contained the software that you were going to use. And then you had to go home and you had to install it. When did that era end?

Jay: Microsoft actually changed that. They bundled a browser in Microsoft Internet Explorer, which I'm sure everybody is likely somewhat familiar with. They bundled it for free in their operating system. So when you downloaded Microsoft, you got Internet Explorer for free. It was actually the subject of a lawsuit, an anti-trust lawsuit. Because the question was - if they're giving away their browser for free, then are they monopolizing basically the internet?

Jay: When Internet Explorer came out, it really changed a lot. I think Netscape was still the most popular browser at the time. There were a few technologies that were needed in order to make something like commerce available - or possible, let's say. And Internet Explorer and Netscape are the first to actually explore those technologies.

So by the late 90s, you really started to see a lot of advanced technologies enter the browser, and new capabilities which enabled the next generation of websites.

Len: So it was probably around the late 90s that people could start actually like entering credit card numbers and buying things on the internet?

Jay: Exactly. I mean, Amazon was around in 95, eBay 96, 97. You wouldn't enter your credit card on it. It would be more of like a bank transaction or you would mail people - there's all sorts of ways of doing things, even without the technologies.

But by that point, you actually started to see technologies which enabled secure transactions online. And that's the most important part, is that when I enter my credit card, it doesn't get hijacked on the way over to the website. So yeah, by the late 90s, you did start to see that.

Len: It's really interesting - most people take that security for granted nowadays. I mean, we have the concept of hacks and stuff like that - which I'll talk about later. But having your credit card number stolen at the point of the transaction is something we're more or less not concerned about anymore.

It reminds me, I remember explaining to one of my aunts once that - she wanted to buy something, and I was like, "Oh you could just go online and buy it and they'll bring it to your house." And she said, "No, no, I would never put my credit card number on the computer."

To this day, I regret explaining to her that, "Actually, your credit card number is already on computers all over the world. That's how credit card companies work now." Her eyes were just wide and with horror at this idea.

But it is interesting that over time, these technologies have become - I mean, there's so many things that have become commonplace, but in particular, secure, at least at time of transaction ,use of credit cards is something that is only about 20 years old.

Jay: Yeah, for sure. I distinctly remember that too, starting to figure out how to buy things on the internet, and people were being very fearful of that. And it's not a concern at all anymore.

Len: Another thing related to commerce that is commonplace now, is using the web to do your banking. Do you know when banks first started getting into the web?

Jay: I think you just gave me a really interesting topic to explore that I really haven't. I could tell you that banks, they were starting to have websites early. I mean, pre-2000. But there wasn't that concept of online banking yet. I would have to think that that came post 2000, after the dot com bubble - that you started to see stuff like that. But I don't have a ton of details on that.

Len: That's another thing that's just such a basic part of our lives now. I mean, I can manage accounts. Anyone can manage accounts all around the world, from your phone even, very easily now. But I imagine huge battles fought against all kinds of enemies, internal and external, by banks in order to make that a reality.

You mentioned the dot com bubble. :et's talk about that a little bit. Because the web had this impact on commerce in all kinds of crazy ways that became a perfect storm in the late 90s.

ne of my little hobby horses about the dot com crash that happened around 2001 that people rarely address, is the opportunity for people to buy and sell stocks online became a thing. Before that, you had to have a certain expertise or just initiation into the process of buying and selling stocks. But all of a sudden in the late 90s, you could sign up for an account and you could see these dynamic charts changing in real time. You didn't need your own Bloomberg terminal or anything like that.

And so one thing that happened was, at the time, if you had a website that was the name of the object you were selling, or the market you were selling into - all of a sudden, you could have an IPO and be worth billions of dollars. It was nuts. And one of the things that drove that was online trading. I had friends who lost tens of thousands of dollars on various schemes, because they just saw everything going up and up and up - until it went down. What the online trading did, was it allowed the companies to IPO, and then that just became this cycle that built and built and built until it came down.

I guess I'm not sure if I even really have a question to ask, after saying that. But let me try and transition that into another question, which is - when did it become possible to start your own web-based company, without needing to buy and maintain your own servers?

Jay: That was a big turning point. Honestly, you didn't really see that until well into the dot com era. Which is 1998, 1999, 2000.

Basically what happened was, any company that - they were called dot coms. It's literally any company that had a .com, was all of a sudden worth ten times, 100 times, 1,000 times what they would be if they were a brick and mortar store or just a normal agency. So you saw like digital agencies like Razorfish with 100 million, 200 million dollars' worth of investment.

There was a site called iVillage, a community site tailored mostly for women. At its peak valuation, it was valued at more than General Electric. Which is just insane. The founders of the sites knew that it was crazy. But what happened was, there was this surge of investment. And eventually there were no business models behind any of these sites, and they weren't making money - and they just hemorrhaged all this money, and that's where you get a bubble burst - and you got a bit of a crash in 2001-ish.

Even at that point, one of the costs of doing business was creating your own servers. And you had these in-house IT people that were maintaining them, for a company of most sizes.

What you did start to see was a little bit of time-sharing networks. These big companies, the oil companies or something like that, would have these servers that would not need to run anything during the summer, or they would not run anything overnight. They would actually lend out the servers for people to use, and that was like a way of hosting various networks and things like that. So you did start to see that.

But if you were, let's say, - which is, I think one of the most famous examples of a dot com company - you definitely had like a basement full of servers, or likely an offsite server farm essentially. And there were plenty of plenty of people on staff that were tasked with just maintaining those.

You saw a lot of outages at that point, because people didn't really know what they were doing. They didn't know what would happen if a million people visited your site in a day. So they were still figuring that out.

Len: That actually leads me into the next theme I'd like to cover, which is - we've talked about the file formats and all of the things that that's enabled. We've talked about commerce and some of the various dimensions to that. One of the things the web has introduced into our lives is some bad things, that we just take for granted. One of which is distributed denial of service attacks.

Do you recall when that became a phenomenon? Where malicious actors would deliberately flood a website with a lot of attention, essentially, in order to shut it down?

I mean to this day, I think the intentions behind it are unclear at best. To overload a server to the point of taking it down, there's not really a business case for it. It really is a malicious attack. It could just be people that think it's funny, which is unfortunately like a good amount of the bad that happens on the web is for that reason. But it could be more a more calculated attack, which sometimes happens as well.

I think you don't really start to see that. I mean, hacking goes back to computers, literally with basically the first computers. There were all sorts of different way - both with good intentions and with bad intentions - to hack computers. You don't really start to see that though until bots become really popular. I think that's only in the last 15 years or so that people have taken the idea of making a computer literally a robot that operates on the web but with malicious intent, and aggregating that to the millions and billions that we see today. You're probably seeing it more now than ever. And it's something that's only very recently, maybe in the last decade, matured to the point of being very, very calculated.

Len: It's a really fascinating thing. Hacking and things like that existed before the web, but most people got onto the internet because of the web. And that's the reason they got exposed to things like the subject of my next question, which is viruses.

It's something that I think a lot of us aren't as concerned about now as we used to be, because like fortunately, not only technology on the good side has advanced, but also people's habits and awareness have improved.

When was the first big virus that came into public consciousness? And perhaps - maybe to narrow it down, I mean I don't expect you to be able to answer this question precisely, but, the first time there was a news headline about people getting hit by a virus.

Jay: I can tell you one thing I've written about in the past. To me it's very interesting, because it happens in the specter of Y2K. Which is, again, something I don't think people are thinking about today, but Y2K was this whole idea that like at the turn of the century - literally on January 1st, 2000 - because of the way that computers were programmed, they were programmed with dates that only had the last two digits, so like 89, 90, 91. And when 2000 turned over, like every server in the world was going to crash, and banks were going to lose all of our money and nukes were going to launch.

And nothing happened. I think there was like two reported instances of like a gas pump malfunctioning. Something like that. But that was all over the press.

And then, I want to say a few months later, we got something that was called the ILOVEYOU virus. It's fascinating to me, because the viruses themselves aren't all that technically advanced. Their goal is to get you to download them. And when you download them, they do something pretty simple. With the ILOVEYOU virus, the - the reason that it spread and it really did spread, was because it was bundled in an email that said, "ILOVEYOU," right? That was the subject line.

And that preyed on people's natural inclinations and instincts and curiosity. And it was self-replicating. So what it did was, it would invade your computer - you would download it, it would invade your computer, and it would start, I think, duplicating or removing all the files on your computer. And then it would go to your contact list, and it would send that exact same email to everybody that you had stored on your computer - and that would spread and spread and spread. Government agencies had to shut down, because all of a sudden 30% of the computers in the agency had downloaded this virus.

I think that remains true of hacking today, in that the most elaborate hacking techniques have very little to do with technical proficiency, and much more to do with what's known, these days, as social engineering. Which is - how can we prey on people's human side, in order to trick them into downloading or getting a virus?

Len: Speaking of the human side and email, I wanted to talk a little bit about that. To this day, my parents - I'm going to pick on my parents a little bit. I love them very much. But they have a landline telephone, and they will answer it whenever it goes off. I find it both cute and interesting at the same time, because that behavior is a remnant of a time when if you missed a phone call, you really missed it.

You really needed to answer the phone when it went off, basically. And also, you knew that on the other end of the line was a human being who knew your number, who was calling you. And so when they get a communication from someone that way, they just assume there's a real person on the other end of it.

When email came out, people related to it the same way. If you got an email in your inbox, that said, "ILOVEYOU," that said anything, "Business Opportunity," you might not have been naive about the content of it - but most people just naturally related to it, like this is a person who knows me, who's a real human being, who's contacting me specifically. And so my specific question on that is, do you remember, or do you know when the Nigerian Prince scam emerged?

Jay: I don't.

Len: Which is something people cannot remember.

Jay: No, I can't tell you an exact date on that, unfortunately. I could tell you - email spam predates the web actually. The first incident of email spam - because email also predates the web by nearly a decade - the guy actually got in a lot of trouble, but it was still a small community of internet people. He was like throwing a party, essentially, like a networking event, and he spammed everybody that he could get his hands on, got this random email.

It was a break in trust. People were still operating under the landline assumption of, "If I get an email, it's because you know my email and this is a correspondence between just the two of us." There wasn't an expectation that you would get something like a newsletter, for instance. Or in his case, spam. So he got banned from a whole lot of mailing lists and things like that for trying something like that. But obviously we couldn't curb the tide. I'm not exactly sure when that stuff started, but I can tell you that, with every technology, spam is early. It's always early. People are trying to figure that stuff out.

Len: Another bad thing that we're accustomed to in our day to day lives now is online shaming.

Shaming of course is nothing new. But the ability to, say, send out a tweet and get on an airplane, and then get off the plane and realize your life's been ruined - is something that we all witness almost on a daily basis now. Do you have any idea of when that became a thing?

I know these questions I'm throwing at you are actually quite random, so thank you for being so game. But there are examples of things that would happen, like in offices. Emails would start going around, where someone had written say a cruel email or a stupid email or just said something dumb.

And then those would leak out of the company that they originated in, and then suddenly everyone around the world would be like, "Oh my God, look at what this person did."

Do you have any idea about when that became a phenomena?

Jay: So on a personal note, I'd say this is - to me, it's one of the biggest failures of the web - is that behavior like, and to be honest - like the shaming is probably the least of the, let's say, abusive or harmful version of that. There's a few other things that are done on the web that stem from that.

I think what happened was early on, and even pre-web - there was this sense that in a community, there were layers of protection. And one of those layers, for instance, was that everyone was anonymous. Which I think is really funny, because I think on Twitter and Facebook etc., there's this assumption that if everybody was anonymous, we'd be all spamming each other all the time, and that there'd be a lot of this abusive behavior. Which, by the way we see plenty of anyway.

But actually, being anonymous was also a defense mechanism. It allowed you - like if I tweeted something out, you couldn't then find my address, and send a SWAT team for instance. Or something like that. You could come out with your identity, if that was something that you were comfortable doing - but you could also hide behind this veil of anonymity.

There was also this idea that growth and community should be small. That growth should be deliberate and that every person should be protected and feel safe, and that banning somebody from their community because they were being harmful wasn't seen as a violation of free speech. It was seen as a way of protecting the community from bad actors, essentially. And starting with the dot com era and continuing on until today, the goal shifted.

Your goal became not - how can I foster a community that feels safe and inclusive and big, but perhaps not for everybody? Some of the earliest social media sites - like BlackPlanet and AsianAvenue, were actually tailored for certain communities for people of color - specifically. And then you've got Facebook and MySpace and a few - Friendster started the trend, and the idea became, "How can we get everybody? I want everybody in the world to be on my network."

And what that did was, it made it impossible to control and to moderate - anybody can join. Anybody can come in. And the mechanisms for creating an account became so simple. You didn't have to pay, you didn't have to do anything, you just need an email address. It became so simple that creating fake accounts became possible. And creating pseudonymous accounts. Now the bad people can hide behind anonymity - but the people that are trying to protect themselves cannot, for instance.

You started to see that shift, I think in the mid-2000s, with the idea that the goal of every website should be, "How can I reach a billion people? How can I reach more than a billion people?" Rather than, "How can I keep people on my site? How can I create an engaging and thoughtful and sustainable community?"

I think it's unfortunate. I don't think it's the fault of any one site or any one person, or any one moment in time. It's just the general commercialization of the web made that inevitable. Because the idea was - if you can get lots of people, you can get lots of money - and that's mostly turned out to be true.

The bottom line is though, you can run a website for - at this point, I don't know? - $100 a year, let's say. And so I don't know why you need a billion dollars a year in revenue, in order to run a community. You really don't. But that became the goal, and I think attitudes started to shift.

Len: Hopefully I'll get a chance to ask you about the huge issue of the public and the private, and the way that's changed our lives online.

But before moving on, I wanted to ask you about another - I'll characterize this a negative thing about the web, that touches on what you just talked about, which is - in order to get and keep a billion people on your site, companies constantly deploy methods of fucking with you.

I'm going to pick specifically on Facebook here. Facebook is a company comprised of people fucking with you.

They're given an assignment. They're like, "Increase the number of interactions with this part of Facebook." And when you open it up - particularly on the web, and you look at it, if you understand what's going on behind it - behind each little part of the 150 ways of interacting with that website, is one or two, or often more people, who are just sitting around all day being monitored by the company itself for the results of their actions and fucking with you.

I'm going to get a little bit mad here, because it really does impact our lives.

For example, Facebook used to be one thing on your phone. Then it became two: Facebook and Messenger. I turned off notifications for Facebook, because they're useless. They're just there to hit me and make me click on something. But I kept Messenger notifications, because at least I knew that was a human being trying to communicate with me.

And then one day, not to long ago, all of a sudden I got, essentially, a Facebook notification through Messenger notifications - saying, "You've been friends with so and so for ten years."

Is there any way forward that you can see on this general topic, of what you were saying? Like the companies don't need to be doing what they are doing to actually run good communities. But at the same time, they're extremely successful and a lot of people spend all day on them.

Jay: I hear anger in your voice. I think you're not alone. It makes me angry. I think it makes a lot of the creators of the web - it makes a lot of the people that understand what's going on, and even a lot of people - and that number by the way, of people that do understand what's going on, it's increasing every day. But it makes a lot of people angry.

I could say a few things about it. One is that there's competing theories on this. Which is that - have we entered a time when the biggest internet companies of today - Facebook, Google, Amazon, etc. - are now institutions? Like General Electric or just behemoth companies that aren't going away for the next 100 years.

Or is it possible that we can enter a time when there is no Facebook anymore? When literally the tide shifts to a point - I mean it happens all the time on the web. It literally happens every five to ten years, where there's just a seismic shift and something different comes around. I don't know if that's possible, because we've entered a phase where it's a given. It's a given that like you have a Facebook account. It's essentially like having an ID. It works and operates in a similar way, and they know that - and they are preying on that for sure.

But I optimistically like to imagine a day in which that whole paradigm is upended. I think there's this idea that they'll be around for the next 50 years, let's say. But there's no proof of that. I mean, we're 30 years into the web. There's no way to tell what the next step might be. There's an entire new generation that understands the dangers that come with everybody being on the same place, in a way that our generation just doesn't understand. And they're going to build solutions that accommodate that. You're starting to see that unfortunately with the same old business models.

But there's going to be hackers of a new generation that are - and again, this is my optimism speaking - there are plenty of people, much smarter than me, that are saying I'm wrong. But I like to think that we'll start to see people use the web to create more open, more inclusive, less centralized tools that enable maybe a more fractured landscape.

But certainly, just a better one. I think if we stay on the path we're on right now, we're, it's only going to get worse. There's no question of that. It's getting worse all the time. But I like to be optimistic and think that it's overturnable.

Len: Maybe moving onto a lighter subject - it's easy to get lost, but there's so much fun on the internet as well.

We touched on it earlier, but I'd like to talk about things that are gone now, and things that we have now - things that are gone now, I mean, in a spirit of nostalgia.

I'm mostly referencing the developed world here. But even that's no so true anymore.

What were internet cafes, and when did they get started? This is one of the things that are gone now.

Jay: So the exact time, I'd actually have to check my website, but I did write a story about internet cafes. They're fascinating to me.

They really didn't get started until the web got started, even though technically they weren't constrained to just the web. There's a lot of internet cafes, for instance, that are tailored towards internet games, even early on. Or internet chat rooms. What was really interesting, was that - so, internet access in the early days was not like it is today, where, at least in the United States, a fairly low monthly fee gets you connected to the web. And obviously, it's on our phones and things like that.

But getting connected was not as simple in the early days. And so these internet cafes took that idea, and they basically made the internet and the web available to everybody - you could just come in and you would basically pay by the hour, and just do whatever you wanted on the internet.

They actually became centers of social activity. So you started to see early versions of what are now basically meetups, where people would meet every week and just like chat. Or you started to see people come together around different technologies, or create new projects inside of these cafes. It's interesting because we're incredibly social these days on the web, and yet we don't really have a community anymore. And just literally being in the same physical space created that.

There's this fascinating component of it, which I wrote about. Which is that, there used to be these web cams, and they would put them in the internet cafes. So when you were away from the internet cafe, you could sit and you could watch what was going on in your internet cafe of choice. You'd sign on to the internet in order to get a window into your internet life that was in many ways physical and social.

They're actually still very, very popular and they're a little bit different - they are still very popular in Korea, for instance. But you don't really see them these days in the US or Europe.

Len: One of the things that we have now is memes. Can you recall what one or two of the first memes were? I think that it might have been the dancing baby?

Jay: The dancing baby was really early on. It was an animation experiment. If anybody doesn't remember it, it's literally a dancing baby. It was on Ally McBeal, it was a big deal.

I think there were a bunch of sites that were meme factories. It was sites like Deviant Art and Newgrounds that were all about creating spreadable, viral content. Which is really just for fun, especially in the beginning. And then the nice thing about memes is they've retained that.

There's ways to weaponize memes. But in general, it's still just a way of having fun on the internet.

In order to understand a meme, it requires inside baseball knowledge of a lot of different things simultaneously, which is just endlessly fascinating, I think. That was true even in the early days. There were these fun games or just short videos and things like that that - it was the kind of thing that's like, my parents don't get it, and that's why it's cool. I think that continues to be true.

Len: One thing we don't have any more is video stores, more or less. Do you have any thoughts about at what point the tipping point came?

Jay: Recently. I think more recently than you might think. Obviously now with Netflix and Hulu and all sorts of streaming platforms, we've been able to move things online. It was only in the last five years or so that we had the broadband capacity in order to do that. I mean it's a crazy amount of data that Netflix alone is exchanging every day through the pipes of the internet.

There were lots of experiments with it. One of Microsoft's earliest experiments was to create an online news channel, essentially. They wanted to create these little videos online. And that actually eventually became MSNBC, the cable channel, which is Microsoft NBC. MSN was their network.

Everybody that tried it in the 90s and early-to-mid-2000s was just ahead of their time, and it just didn't take off. There were experiments, but I think we only just got there recently.

Len: One of the things that we do have now is easy, truly working and dependable video calling. Do you have any sense of when we turned the corner on that? Because that also seems to me to be actually more recent than it might seem.

Jay: If I have a sense of it, it's really only because I've been doing video calls for the last decade, and I remember what it was like at the beginning. There were drop-outs and it was really fuzzy, and it was a lot to deal with.

Again, I think the issue's here mostly with bandwidth, and the infrastructure part is something that I'm aware of, but I don't have like a lot of knowledge about. I can't speak too much about it.

Len: Going back to big serious things. For the next part of the interview, the theme I'd like to talk about is government.

You brought up earlier on that governments got involved with the web when Microsoft started including Internet Explorer for free with its operating system. Now, of course governments have been involved since the beginning. The internet itself was a government project. The web came from CERN, which was funded by various governments itself. But do you have a sense of when governments first started seeing the web as something to regulate?

Jay: One of the earliest examples of regulation - the Microsoft case is an early attempt at that, although it was really more a focus on whether or not Microsoft was becoming a monopoly, and it was an anti-trust suit. Which Microsoft won.

One of the earliest attempts to regulate was a law, it's called COPA, Children's Online Protection Act. It's basically a way to ensure that when children are online and viewing things, we're not collecting data about them. And there's a lot more rules.

I have some experience of this after working at Sesame Street. There are a lot more rules when you're building a website that's tailored for children, that you can get fined, or you can get your site taken down if you don't follow them - than there are for building a site for adults. That was in the late 90s, you started to see that.

Then more recently you've seen a lot more, maybe going the other way. Things like SOPA, which attempt to regulate what can and can't be on the web. It's a tricky territory, because you do want to protect people's intellectual property, to the extent that you believe in a concept like that. But you also want to - the web is a decentralized open platform, and to infringe on that is to threaten its very existence.

I think we're in a period of time right now when there's a lot of people that would welcome government intervention - myself included - in terms of, especially issues related to privacy and things. But the government moves slow, and the internet moves fast, and there's a lot of misunderstanding about how the internet works. I think we just need to be careful about what, what goes on there.

Len: That's interesting. While preparing for this podcast, I listened to another podcast when it was published recently - 2 Girls 1 Podcast. It's a really good episode. And in that episode, you talk about being a supporter of GDPR, the General Data Protection Regulation, that was big news around mid-2018. I had to become formally Chief Data Protection Officer for Leanpub, and I wanted to ask you, what is it about - I mean, there are lots of complexities around it, but what is it about it, if you could speak at a general level, that you're in favor of.

For me the most important part about GDPR - never mind the, let's say, execution of it - is that it puts users back in control of their data. So if my data is up on a site, I can request to have that data removed completely. I should be able to tell Facebook, "I don't want you to have any of my activity, any of my friends, nothing I've ever done. I want you to delete it from your servers." It offers really, really intense technical challenges, because it's not something people have thought about.

I'm massively in favor of giving people the mechanisms needed in order to have some control over how their data is being propagated and used across these massive advertising networks and social networks. I think if you take that and you combine it with digital literacy and education - then you start to have a much more informed consumer, and you start to have people that take control of their digital lives a little bit. I think that in the long run, it could help solve some of these privacy issues ahead of time.

Len: It's a really fascinating issue that you touched on there. The way that it's meant to give people a sense of control over what's happening to them in their lives.

I think this is somewhat related to my rant about being fucked with earlier, but I remember not too long ago I moved to a new city, and I found a place to buy cookware, and I gave them my email address. And when I got home and fired up Google, there were cookware advertisements in my search results for that store.

Jay: So many stories like that.

Len: I really felt fucked with. And although there are many things about - particularly as you say, about the execution of GDPR and the communication to the public about it that may have been imperfect - in many ways, it was a response to the fact that people were feeling like, "It's not just happening on the web anymore. It's like I go to a store and something I do there has an impact on - like, verbally something I do there then has an impact on my life."

On that note, and you brought up copyright earlier. One of the controversies of the past year around the web was something called Article 13 in the EU's Copyright Directive. Is that something you followed, and that you have a particular--?

Jay: Not really, please, explain it to me.

Len: So, the controversy was that article 13, for the purpose of protecting copyright, might actually force everyone in the world using the internet to place a filter on anything they upload to it, essentially. This would be not just the web. It would be anything you're putting out there - it should go through a filter, to check to see if it contains copyrighted material.

This is a bit of a digression, I suppose. But this is an old, old battle between companies that own intellectual property, and people who want to listen to music or watch movies or make memes, and things like that.

I remember - I don't think this is an invented memory - there was a time when organizations that represent people who own intellectual property, wanted to install, in all computers, software that would look at what you're doing and prevent you from doing things that they didn't want you to do. An example would be, if you're running video, installed in the hardware, is something that can check to see if you're looking at something that's been pirated.

Do you see this battle continuing?

Jay: Oh yeah. I could tell you, one of the hotly contested debates of now is the W3C, which is the organization that regulates and maintains the standards of the web - and not in a formal way, they can't force anybody to do anything. But it's a way for a bunch of browsers and websites and stakeholders to get together and basically talk about the future of the web.

And one of the things that they're debating right now, is whether or not to introduce DRM into the web. So right now, when you view something on like Netflix or Hulu, theyr'e using all this weird, proprietary technology, as a way of preventing you, the consumer, from downloading that. There's a lot of opinions on both sides.

I personally - if I'm just going to like throw my opinion out, I believe very deeply in open source and creative commons and open content like that. I think DRM would endanger the web in ways that maybe we don't see right now.

If you're interested in opinions about that in particular, I think Corey Doctorow's probably the person talking about it the most these days. All of which is to say that - yes is the answer. This is going to be a question. I think it's taken a back seat for a little while, because there's these much larger issues going on with the web and the internet in general, that are being debated in public spaces. But eventually we'll come back to this DRM question, and copyright in general, and how copyright and intellectual property is managed online.

Len: There's a really interesting example I like to bring up when having this argument. My opinion, just to throw it out there - is that I'm very much against DRM, in all circumstances.

The analogy I like to use is - imagine if every parcel that you sent, or in the olden days, paper letter that you sent - were inspected to see if there was something copyrighted in there, that you hadn't paid for. Nobody, nobody, would approve of something like that. Because we understand the implications of having everything we do inspected in that way, in the physical realm.

Len: But there's a lingering sense that I think - I'm going to make maybe a controversial claim - there really is a deep generational thing, where some people relate to what happens on the computer, like it's not real in the way other things are real, and it doesn't matter in the way that other things matter. And this manifests itself in things like Senators in the United States who boast about being unable to email.

Jay: Yes. There is a weird concept. I think it started because you really used to have this whole - you would talk about your digital life with like wonderment and amazement. Like, "I have this fantastic digital life." I think over time, that wonder faded away. But there was still this idea that there's a digital life and there's a real life. And that's a concept that continues to this day.

Sometimes I'll talk to, let's say my parents or my in-laws. And they'll be like, "Why are they putting these stupid pictures on the internet?" Or, "Why are you putting your business out there?" thing.

Me, people I know, like a whole generation, and honestly, the generation under me is even worse, you would say. But the concept I think is interesting. Because I understand the idea of public and private in a way that my parents didn't. And the generation under me understands public and private in a way that I don't. There's this sense that everything is public by default, and it's because our digital lives are our real lives. So everything in our real lives emanates out into the digital world and becomes public - and you should operate accordingly, basically.

I wrote recently about danah boyd, the researcher. She currently works, I believe, in Microsoft. But she's done research for the last 20 years on the web and the internet and all sorts of interesting things. Highly recommend just checking out anything by her.

She has this concept of super publics, which is the idea that when we say something online right now, we are saying it always. We are saying it forever in the future. We are saying it to everybody simultaneously at once. And obviously in practice, that's not necessarily true, but theoretically it is.

There's all sorts of techniques that the younger generation is developing. I think memes are a really interesting example of this, it's like a way of communicating with one another in a way that is coded, to the extent that like people actually can't understand it unless they're in on the reference.

If you ever watch like a teenager use Snapchat, you'll know exactly what I'm talking about. Basically, they're communicating in a way that is foreign. I think danah boyd refers to it as social stenography, which is this idea that it's essentially coded for just the generation. You're going to start to see more of that, I think.

Obviously digital natives are now in their 30s and 40s. So, you're just going to start to see that concept of public - I think, and private - shift, and that's why I said before I'm very helpful about what could be done, once that's just like a foregone conclusion. Len: I read that great post that you wrote, and I'll definitely link to it in the transcription for this interview - it leads me to try and touch on something, I guess what might be a good way to end this part of the interview, which is that there's no distinction between public and private for, let's say, people born in the last 20 years or so, in the way that there used to be in the past.

One thing you write about, for example, is the fact that anything you do online can be screenshotted, for example. This became a Colbert Report joke when he was interviewing the founders of Snapchat, where they're like, "Yeah, it disappears." And he's like, "Can't anybody just take a screenshot of it?" And they're both like - if I remember correctly, I might be inventing this - but they both went red and were like, "Yeah."

There's a saying in business and publicity - don't ever send an email that you don't want the whole world to see, because even if it's somehow in a network where it can't be forwarded out of there, it can be shared with anyone else in that network, and it can be screenshotted. And then that can be spread around, and if it's believable, people will believe it. And if it's not believable, some people will believe it.

This might seem like an odd thing to bring up, but it reminded me of a story I was told by someone in DC who'd just had a child born. They'd been looking into schools, and one of the schools they looked at gave all the kids iPads, and one of the things that the kids did with the iPads was record themselves giving reports, so they could then watch themselves afterwards and then refine their performance.

I think there's a really interesting shift that's happened, and this is very recent, that this reality that we faced, about the possibility of anything you do online becoming public at some point. Like instantly, which is one danger. Or like 20 years later, which is another danger. This is actually now true in public as well. Because anything you do could be recorded either by a camera that's fixed to a building, or that's being held by a person.

Are you optimistic about the new generation dealing with that issue?

Jay: My short answer is, "Yes." I don't want to speak about things that I don't necessarily have a lot of like expertise on, but I think it's a net positive. I think this idea that everything is public is exposing a lot of things. It's one of the reasons we're starting to see movements around upending old social orders and exposing people for who they truly are, and things like that. I think ultimately that part of it is a net positive.

I am always optimistic about the social aspects. I think there's a lot of this idea of like, "Get off your computer, get off your phone and go outside." Which - let's say from a biological perspective, I guess, does make sense. You can't just sit on the couch all day.

But I do think that's a misunderstanding of the current mode of how people operate - in that our social lives are very much online, and that you're starting to see kids, like younger kids and teenagers, and just people that are experimenting and opening up their eyes, to new perspectives really early on - reaching out to communities and understanding the world in a way that maybe they wouldn't even get a chance to do until college or later normally.

Importantly, they're talking to people that aren't like them, with perspectives that aren't like theirs - and trying things out - not feeling constrained by the way that things currently operate. I think in that sense, that part is a net positive. Obviously there's plenty of negatives that come with it, and I think those are being well covered, and we need to think about them constructively. But I like to remain optimistic about it.

Len: I'm going to take the opportunity on that somewhat optimistic note, to move onto the next part of the interview.

There are lots of things I brought up, saying we'll be talking about later in this interview, that we didn't get to touch on. One of those was publishing. But your book is called, The History of the Web, Volume 1, so maybe we'll have a chance to have another interview and cover those topics when your second volume comes out.

For the last part of the interview - when I'm interviewing a Leanpub author, I always like to talk to them about their experience self-publishing a little bit, because quite a few of the listeners to this podcast are authors themselves, or people who are considering publishing books. So I guess my first question is, why did you choose to publish your book on Leanpub?

Jay: I'd been thinking about doing an ebook for a little while. It's something that I've had requested from me from a few different people. I thought about it. I'd been giving away this content for free for the last two years, and I did want to make it available to people, but I've also been asked, "How can I support you?" People like to throw me a few dollars or just show that they are very interested, or they want me to keep going with it. It's my promise - I will be keeping going with it for a while.

I researched a few different things. For me, the biggest draw to Leanpub was the ability to set a price so that people, if they wanted to - I've had a few people that contributed because they were really just contributing to me, and the ongoing project - and the ebook is a very nice keepsake. It's a way for them to hold on to that content, and read it independent of their email inbox.

So that was one draw, the other being that it's the only tool I found ebook publishing-wise that basically allows you to take massive quantities from a blog and convert it into an ebook really simply. Again, I'm very much in favor of openness and things like that. So I like that I can just download my files. I mean, if I published on Amazon for instance, that would be locked into their network. So, a mixture of reasons I guess.

Len: Speaking of openness, actually that reminds me. There was just an article that I read yesterday, I think it might have been published yesterday, on Vox, about a little mini-scandal in the book publishing world that's going on right now, where someone well-known in journalism had a book come out - or at least had early drafts of a book circulated, that appeared to have a lot of errors. This article on Vox is about the fact that the conventional publishing workflow more or less leaves fact checking to the author, and if they have a staff, perhaps someone in the publishing company.

One of the interesting things, is that that would seem to imply for a self-published author that - oh no, you're doubly screwed, because you don't even have the possibility of a team fact checking you.

But the thing about Leanpub in particular, is that it's not just a technology, it's also a publishing workflow philosophy. Because you can easily update things, and because you can publish in-progress, the fact checking happens organically as you reach out to your audience. Is that something that you've experienced?

Jay: Fact checking for me is extremely important. Every single one of my entries has a list of sources. Whenever possible, I literally try to verify it with people that lived the experience that I'm discussing. So it's important to me generally.

I think with Leanpub, what was nice for me, was I basically converted my blog into Markdown files, which gave me a way to go through everything.

Once again, I was able to actually find a few things and clean up a few things. I would manage to rearrange the order of things as well, to make it chronological, which is not how I do the newsletter. I think for me, being able to like quickly preview things was massive. I just generated a PDF and checked it out. It gave me a chance to review. And it's something that I'm obsessed about anyway.

Len: And have readers contacted you with errors that they've found?

Jay: Sure.

Len: Is the most direct thing -

Jay: It's the web. I've been so fortunate, because I have been contacted many, many times. Never with malicious intent, never in a patronizing way. Always helpful. I have a friend that basically Twitter messages me every few weeks with typos. So it ranges from that, to people that are like, "Hey, I lived what you just talked about and you got this a little bit wrong." And so I always go back and fix those up. I've managed to have great conversations from those. So I encourage it, always.

Len: It's great to hear you say that. That is consistent with what we've heard over the years from a lot of different authors, in a lot of different areas.

One of the canonical types of books to be published on Leanpub is programming books. And if someone's got some code snippet in there, that actually doesn't work anymore, or didn't work at all, readers not only love contacting authors and hearing back from authors, they love helping make the books better. And they particularly love seeing a change that they pointed out made to the actual book. It's something that I think a lot of people are actually quite - they're a little bit scared when they publish something, that they're going to get this negativity, they're going to get negative interactions, patronizing interactions, attacks.

I can't make any guarantees, but for the most part that's not the experience that authors have. They're are a lot of instances comprised of people who are interested in what they're writing and in who they are, and in helping them and in helping improve their books.

Jay: I will say, for me, I have been terrified on occasions, for various reasons. Maybe I'm inserting my opinion, and it's a controversial one, or maybe it's just like - it's something that's not talked about a lot, and I'm worried about getting it wrong.

For me, getting feedback from readers has actually helped with that. Because it's like somebody's checking me, and I like that. I like that. If someone's going to call me on it and I'm on the web, I get to change it.

Talking about Leanpub, that's another nice thing - I can always issue a correction and send out an email to all my readers and be like, "I'm very sorry but it's updated now, and you can get the newest version here."

Len: The last question I like to ask on this podcast is - if there was anything we could build for you, or anything we could fix for you, is there anything that comes to mind?

Jay: I feel like early on, I think there is a way to import directly from WordPress, I'm not 100% sure on that. But I do remember not having a good experience with that. I'm a programmer, so I created a script that converted all of my posts to Markdown, and just did it that way. Progamatically, I understand how complicated it is, to like crawl a site, and pick which articles you want, and possibly even rearrange them and just import them that way. That would be a dream, I think.

Len: Thanks very much for that. It's not exactly a flashback, but it's inspiring me - Leanpub actually started out as a blog-to-book service. The first book was Startup Lessons Learned by Eric Ries, from his pre-Lean Startup days.

Importing from blogs is actually not something that we've touched in a long time, because we've just become focused over the years on building other tools. But I'll definitely communicate to the team that maybe that part of Leanpub maybe has a few cobwebs around it, that we might want to improve.

So thank you very much Jay for taking the time to do this interview, and for your amazing newsletter and for your book, and all the best for a great 2019.

Jay: Great, thanks for having me, and it was a blast.

Len: Thanks very much.

Podcast info & credits
  • Published on January 25th, 2019
  • Interview by Len Epp on January 16th, 2019
  • Transcribed by Alys McDonough