A Conversation with Andrew Smales, Founder of Diaryland

Mary Phillips-Sandy
17 min readJun 25, 2013

Diaryland, launched in 1999, helped thousands of people—me included—learn how to blog. Early internet culture distinguished online diaries (personal updates, day-in-the-life reflections) from weblogs (links and commentary, intended to be servicey and/or witty), but that line often blurred, and didn’t fully account for writers who saw the pure entertainment and literary potential of the medium. From its beginning through the early- and mid-2000s, Diaryland hosted unique, wonderful stuff: ann-frank’s hilarious personal essays, the comic curmudgeon character Uncle Bob (and “Bob”’s Brad Pitt parody diary), Sundaygirl’s captivating, way-pre-Girls tales of being single in New York (and then of being married and a mom).

Unlike its peers LiveJournal and Blogger, Diaryland was never acquired by a larger company and has remained much as it was a decade ago. Perhaps not coincidentally, it has faded from the greater internet conversation, which has moved on to bigger, buzzier things. What happened to Diaryland and its sister platform Pitas? Why weren’t they among the sites that profited from waves of financial interest in online products and platforms? I spoke with founder Andrew Smales at his home in Canada, shortly after news broke that Yahoo had acquired Tumblr, and just before we learned that Xanga was shutting down for good.

Mind if I ask when you were born?

Ahhhh. Ahhhhhh. [Laughs.] I was born in ’74. I’ve gotten to that age now where any time anyone asks “How old are you?” I’m like, Oh god. It’s no fun being old.

How’d you discover the internet?

I went to university for a while and there were a couple people on the floor who used [the internet], but later I switched schools to a college in Toronto, and I was in a course for advertising. There was a graphic design component, so there were a lot of computers and computer use, so- that would’ve been ’95, ’96.

It’s such a crazy change. I’ve thought about it a lot lately because I have kids now, and I try to explain to them, you know, “When I was a kid, you couldn’t just get these answers.” There are so many times they’ll ask me something and I’ll pull out my phone, pull up Wikipedia and get the answer. When I was a kid, I’d ask my parents stuff and they’d say, “I dunno, we can go to the library next weekend.”

When you first got involved in the online world, were you trying to make tools for yourself or were you immediately drawn to the idea of making tools other people could use?

I got interested in graphic design, and then web design because of that, and I fell into an online community of web designers. There were mailing lists, and this community called New Dream. The founders of Dreamhost formed that as they were starting Dreamhost, or just after. It was basically a mailing list, and they had a couple dozen people who they’d give free hosting to.

I became part of that list, and I ended up working for Dreamhost.

Was this when you were still in college?

No, this was just after. I didn’t finish my advertising course, I did the schoolwork but then we had to do a three or four month placement at an ad agency and I thought, yeeeaahh, I don’t know if I want to do advertising. So I got a job at a dial-up provider in Toronto, doing tech support on the midnight shift. That’s when I learned a lot about webpage design. I was writing at night for months, just putting things up on a webpage, and I had a one-way mailing list that I ran.

Did you graduate?

Nope. No. Never got a degree.

So you were working at the dial-up and then you got hired by Dreamhost.

Yeah, I worked there for a while. Then I started running what I didn’t realize was a weblog. I set up a page called Every Link I Went To Today. Every webpage I went to, I’d put the link up and maybe one sentence. One day that guy- do you know Fireland? This guy Josh Allen, he’s had a site for a long time called Fireland, now he’s one of these guys with a lot of Twitter followers. At some point he emailed me going, “Oh, nice weblog.” I had never heard the word. That would’ve been in 1997 or ’98. I looked up what those were and thought, yeah, that’s what I’m doing.

I wrote a tool so I could update mine without having to edit the html all the time. It wasn’t anything sophisticated. At some point I thought, hey, I could make the Hotmail of- I remember distinctly being in my basement apartment and thinking about Hotmail, like, I should do that except with online diaries. At the time there was a pretty distinct line between online diaries and weblogs that were mostly links with a little bit of commentary.

Let’s talk about that. It sounds like the first thing you built was the prototype of Pitas, the tool you created that let people generate a ’90s-style weblog of links. When did you launch Pitas? Early ’99?

Yeah, I think so.

So at some point did you just decide, I want to share this tool with other people who make weblogs? Because then then you made Diaryland, which was very different.

Originally the idea was to do Diaryland, and then Pitas kind of- I mean I have a habit of that sort of- I forget what happened. Oh, I know, I realized I had to change the name of it ’cause there’s a site that’s got a name that’s similar kind of in the same space. While I couldn’t think of a name, I started working on this other site I’d been meaning to do. I’m very, um. I don’t know. My attention sometimes is not good with that stuff.

So I was working on Diaryland, then switched to Pitas.

Why’d you call it Pitas? Did it stand for pain in the ass?

No, I’d never heard that before. The day it launched, there wasn’t much going on on the internet then. So a lot of the bigger names in weblogging were linking to it and talking about it. I had kind of made fun of the weblog world, written something about it. One guy thought it was a joke site because it was called Pitas. He thought it was a parody site.

The actual reason for it was that I bought the domain name pitas at some point before that. I’d sit around—I think a lot of people at the time did this—and I would look up domains to see if they were taken or not. I’d pick common words. So I’d already purchased [pitas.com], thinking, whatever, it’s a common word, a short word, it’s a thing, it’s an actual product. And it’s just kind of neat to own. There wasn’t a lot of thought in it. There’s no metaphor.

When you launched Pitas you’d been using it on your own for a while. Did you have any expectations about how other people might use it? Did you feel like you were innovating in some way?

As far as I knew, such a thing did not exist. I was excited when I made it. I remember getting it done and putting the finishing touches—it was the same thing with Diaryland—it’s a very odd feeling of, oh yeah, this thing is all done and I get to launch it now.

I definitely wanted a lot of people to use it. I know so many people who launch websites or products, and everybody always thinks that it’s going to be a huge thing. And then after the fact I think people probably lie a bit, and say, “Oh, I didn’t know.” I’m sure the Tumblr guy doesn’t say this, but people say, “I just made it for me and my buddies, and then it took off.” Maybe now people don’t say that so much. But at the time, I was thinking, ahh, I’d love for a thousand people to use this.

How many people used Pitas at its maximum?

I never was great at tracking, like, actual active users. I would count how many people had signed up. I did check active users now and then. I don’t know, maybe 50,000.

That’s a lot for back then.

It is. That would be, active in the last three months. It wasn’t like every single day 50,000 people were on it.

You had this intuitive little tool that was easy to use, that no one had done before, and clearly it resonated because at least 50,000 people took the time to sign up and play with it. At that point, given that Diaryland was also on your mind, did it occur to you to go to an investor and try to build a plan?

Noooo. [Laughs.] No, not at all. That’s like- my biggest failing or something is that that’s not my- even the sites that I’m working on now, I’ve got a couple things I’m going to put out. One in particular, this site would probably benefit from an investor, I guess. But it doesn’t appeal to me that much because then I’d have to hire people, and get an office, and do all this stuff that is not something that interests me or that I think I would be any good at.

Once [Pitas] started getting popular, originally I ran it on a Dreamhost account, on their server, and within a month or two I had to get a dedicated server. But I never tried to approach anybody to invest in anything.

And a little while later Diaryland came into being. I remember I discovered Diaryland a few months after it launched, that was late 1999?

Oh, man. Hold on. I gotta look. I feel like it might’ve been September, except I know I went to a Greek restaurant after it launched, and we sat on the patio. That was the day after. It wasn’t related, I just remember that. Oh shoot. I thought on my user info page it said when somebody signed up and I was gonna look it up for myself. Well, I think it might’ve been September. Hang on, let me check. Okay, it was definitely five-ish months after Pitas launched, maybe. I’m not sure why it would’ve taken that long. I guess- hold on a second here. [Andrew is typing on his computer.] Yeah, that sounds about right. I think it was September.

Diaryland and Pitas had such a specific aesthetic. It was simple, twee, but it was smart and funny, everything from the sign-up instructions to how the graphics looked. I had the sense that the site was a distinct and direct expression of you and your personality—you even wrote a Diaryland theme song. Were you trying to put your stamp on it?

That song, somebody linked that the other day on Tumblr. Why can’t that go away? One day I was messing around and made that. It was more like, haha, why not? This is so dumb. I definitely was aware that this was not something a professional site would do.

But you could’ve turned Diaryland into something very different. And I’m wondering why.

There were times when I tried to cash in to some degree.

Did you reach out to people or did they reach out to you?

I’m trying to remember. The first thing was in, it might’ve been in early 2000 or maybe late ’99. There was a guy [Bill Martin] who had started a huge investment site, it was a message board for investing. It was called RagingBull.com. It got big, huge traffic. The guys who ran it, or one of the founders, sold it.

So he had a bunch of money and was a savvy business-y guy, and he started a company that was going to buy a bunch of sites and create a network, have them all intertwined. They did buy a site, Ironminds it was called, it was a web magazine. This company, Novix, they had all this money, and I was wrapped up doing this deal with him for quite a long time.

Martin made an offer for Diaryland as part of the network Novix was building?

We had a deal for Diaryland and Pitas. They would own it, and I would still run it. I think they were gonna have, like, technical people helping out. In retrospect, I’m not really sure what that would have entailed. The theory was that it was still gonna be the site that it already was.

Did you have lawyers or representation? Or was it just you on the phone with these guys?

It wasn’t that formal. I talked to Bill a lot. We had papers, I’m pretty sure I signed some stuff. Pretty sure. I made one big mistake when things were dragging on a bit and this guy said, Listen, do you want me to send you a bunch of money in advance? Like ten thousand bucks, since it’s taking longer. I don’t know what I was thinking. It might have been less than that, but I was like, yeah no, whatever. I was paying a couple hundred bucks a month for a server. I think I was just like-

Hold on, Andrew. Someone offered to send you several thousand dollars up front and you said not to bother?

I think so. I could be wrong. I’m probably getting it wrong because it probably wasn’t- it couldn’t have been ten thousand. It must have been something else. Thinking about it now, I can’t really imagine saying don’t bother, but- maybe it was that he wanted to change the deal or something, change the ratio of stock to cash. Ahhhhh. I can’t remember.

It does sound really dumb.

It also sounds like this was very casual. Do you think part of that was because there wasn’t constant coverage of the day-to-day of internet deals? Did you have any sense of what this game was? Did you even realize it was a game?

That’s totally true. The amount of knowledge out there about how acquisitions worked was nothing compared to now. Now, if you want to find out what’s a standard deal, you go on Quora or something, everything is completely laid out.

What happened with [Novix] was the company went under one day. There was no money. I remember thinking I should find somebody else to buy these sites, because I had my heart set on it at that point. I didn’t like the idea of having to wake up in the middle of the night. One of my big hassles at the time, especially when traffic was exploding, every once in a while the site would go down or the database would get slow. I’d have to go in to chill things out on the server, and it was hard to get online remotely, like away from my house. If I wanted to go on a trip, I remember being like, oh my god, I can’t go somewhere if I’m going to be off the internet for eighteen hours while I travel. I couldn’t get internet at airports or anything like that.

I remember those database slowdowns. How many people were using Diaryland at its height? Do you have any sense of the maximum?

It was much higher than Pitas. This is over, what, 14 years, but there are like 2.2 million registered users. Probably 20 or 30 percent of them, maybe 20 percent were active for a period of time.

Diaryland wasn’t one of those sites where you couldn’t tell what it did or see why anyone would want it. In that era of the internet bubble, you had built something that had actual value to users, something that could be monetized. Did you see it that way?

I think I underestimated it, in retrospect. Back then people weren’t paying for things [online]. There were discussions about, Can you charge to use a service on the web? These days people set up sites all the time, it’s five bucks a month, seven bucks a month. Back then, that was almost crazy talk. Originally the thing with Diaryland was that I was going to run ads in the members’ area, not on the diaries. When the dot com crash happened the ad networks disappeared. That’s when I switched to having the gold membership and the super gold membership.

Did a lot of people buy those?

Yeah, they did. It wasn’t a crazy amount. I’ve occasionally gotten angry emails from people saying, “I’ve used the site for years, and I know you’re rich because all these people pay you,” and I was like, what are you talking about? But enough people signed up that it covered the server bills in the first couple of years, and then made a pretty decent profit.

Diaryland was a social network as much as it was a platform. You could follow people, people would follow you back. Was that a strategy that you thought was going to be important to the web later?

It was more like, I think that’ll make it a better product.

A lot of things on the site were kind of like, Oh, I’d like this. But always in the back of my mind was, will other people want this too? I never put anything on the site that was really esoteric that only I would want.

The social aspect was there from day one. It had a life of its own and the tools enabled it, and then people ran with it.

Do you see Diaryland as a thing that’s still going, that’s still part of your life? Or do you feel like it ended at a certain point, or that there was an era that ended?

There was definitely an era that ended. In the early days there was such an explosion of blogs. Every week, there’d be a couple of reporters who would write, saying “We’re doing an article on online diaries.” They’d all have the same angle, which was, “Why are people putting facts about their personal lives on the internet?” Yep, wait till Facebook comes along.

So I was getting 2,000 people a day signing up, around 2,000 or 2,500 for a good part of that time. After that cooled off, after a couple of years, it started being back to 200 to 300 people a day.

Also there was an incident in, like, maybe 2008- there was an acquisition that went bad. That bummed me out. I still ran the site, I was online every day, but I wasn’t keeping up with what was going on in the web world.

What happened?

It was annoying, because it dragged out for so long, it was like a year where I visited San Francisco three or four times, I went to New York City to meet with people from San Francisco who were there for some reason. It was that company Six Apart. So I’d go to them in San Francisco. They really wanted me to move there. It was at the point where me and my girlfriend at the time, my wife now, we were driving around with them to get an idea of neighborhoods for when we moved.

It was just one of those things where it was so disruptive, because before they’d approached me, I had decided, well, I’ll keep running this. I wasn’t out looking for investments.

And you still had no lawyers or representatives? It was just you talking to people you knew?

By this point I knew more people in the web world who I could talk to, and I had a feel for what a decent deal was. I think I negotiated a pretty- I was happy enough with the deal we’d negotiated. Even now, I think it was fair. Lawyers were going to come in once we got down to signing papers.

We ended up making a deal and shaking hands, and then I didn’t hear from them for a couple of weeks. One day they called and were like “Ah, our board voted against it.” I was like, Um, you know we shook hands on that, you didn’t mention anything about a board. So that was really annoying.

Right after that, now I think about it—I forgot about this, actually—just after that I had another deal come up, but this one was very exploratory. It was a web company I knew, we met and talked about the idea, blah blah, but I think they were more interested in flat-out hiring me. Then they were like, you gotta move into California. When I heard that I said, nope, no.

Were you committed to staying in Canada because of your girlfriend, now your wife, and wanting to raise kids there?

I wasn’t super against going to the States, but I would’ve rather stayed here and traveled there every couple of weeks or something. I didn’t like the idea of only seeing my family every nine months, or at Christmas. We didn’t have kids then, but we did have a dog. We were kind of settled.

You didn’t want to be one of these startup guys who lives and breathes the startup and does whatever it takes, 24/7, to make it successful both at a product level and at a financial level.

I never had that instinct, unfortunately. I think a lot of people who are like that, they have people around them who are like that. Either they’re from a successful or rich family, or they go to school with a bunch of people who are like that. I’ve met a lot of people in the last couple of years who do startups in Toronto who are like, “Oh, me and my two cofounders, we went to high school together, then we went to university together and now we do this.” Having like-minded people gets you into that mode, but I never was in that mode at all. I didn’t feel like the people who were doing that were like me. They all seemed a bit older, a bit more business-y. I’m definitely not a business man.

So are you freelancing now?

To some degree. I’ve been doing some work for people, consulting in- I don’t want to say traffic building. I’m just helping out some people with improving their web sites to the point where people will enjoy going to them.

And you run Castmate.fm, a podcasting tool.

That’s the big project, yeah. It’s not insanely busy yet, but I think I’ve had that open for maybe a year and a half. The first year I had some other stuff going, so it was functional but I didn’t really work on promoting it, but lately it’s taking off a little more. Yeah, that’s the thing I am most hopeful about, or most concentrated on, I guess.

Are you going to take some of the lessons you learned from those Diaryland years and approach Castmate a little differently?

I don’t know. Yeah. No. Yeah, probably not. The thing is, I’m more into the approach of- are you familiar with 37signals? Their whole thing is they make amazing products, and they’re all self-funded, or I think they are. They don’t- oh shoot, do they have investors? My understanding is that they do it themselves, and make all their money from customers. They’re not venture capital-backed or anything like that, they’re just making a really good product and people are paying for it. That’s my plan for Castmate: Make the best product I can. My whole plan for it is the subscription fees. I’m not looking to get a bunch of funding. It’s kind of the same plan I had in the early days of Diaryland. Just run the site, make it good.

Will that turn out to be the savvy choice, perhaps? There are only so many multi-million deals that are going to happen, so do you think your approach may be what determines who succeeds and who doesn’t, in the long run?

Do you know Y Combinator? They want to have a big home run or a strikeout. A very small percentage of their sites become million-dollar things, like Airbnb. That might be fine for them, but trying to create something that’s going to be in that one percent is a worse idea than coming up with an actual useful good thing.

The other thing is, it takes a certain personality type or set of skills to become the guy who’s going to Silicon Valley and schmoozing and getting some ridiculously advantageous deal that he shouldn’t be getting, or that doesn’t really reflect the value of your site. You have to be a certain kind of person, and if you’re not, it’s probably not going to work. So even if I, in 1999, had moved to San Francisco and tried to go to a bunch of events and do whatever people do to schmooze, I don’t think it would’ve worked anyway. At least I like to tell myself that.

There’s a certain amount of nostalgia for Diaryland out there, whether people miss their younger selves who used it, or the web that was a little more secret, since now it’s open to everybody. Do you feel that too?

I don’t feel any nostalgia, personally, but that’s because my interactions with the site are mostly from the point of view of an administrator. That hasn’t changed much.

There was a cool feeling at the time, even as the internet was starting to take off. That was when I looked back, a year or two into it, and thought, this felt a little more enclosed back then, like an actual culture or subculture.

On the whole, I don’t miss that time because everything on the internet is so much better now. You can get on it anywhere. I know what you’re talking about, and there was a neat feeling back then, of that little close thing, but what can you do? The internet is so much better overall. It makes up for losing that.