Web Masters Episode #9: Joshua Schachter

Below is a transcription of  Web Masters Episode 9: Joshua Schachter. To learn more about Web Masters and subscribe, check out the Web Masters podcast page.



How can del.icio.us help promote my site?

Joshua Schachter:

I remember once I was getting on a plane and the website had gone down hard and I was on a Danger Hiptop. This is Andy Rubin’s first company before Android. And it was this little thing where the screen flipped open and had a little keyboard. And I was SSH’d into the server and I’m bringing the site back up. The steward is standing over me like Sir, you have to put your devices away. And I’m like, just one second, please. And I’m like, PS, ox, pipe, grep, mysql, pipe, XR, kill, dash, nine, whatever, restart. And I think I did not manage to bring the site back up. So the site was down while I was crossing the country, oops.

Aaron Dinin:

Oops is probably a bit of an understatement here. Oops, is something you say when you maybe drop your pen or accidentally bump into someone on the sidewalk. But in this case that oops was about not being able to restart a website server before getting on a five hour cross country flight in the early 2000s, back when there was no internet on planes. And it was a big problem because the crashed website was del.icio.us. The social bookmarking phenomenon that helped usher in the age of web 2.0, the person who couldn’t get it fixed before takeoff. Well, that was del.icio.us creator and founder, Joshua Schachter. Are you ready to hear his story? Great. Let’s get dialed in.

[INTRO]

Aaron Dinin:

It’s time for another episode of Web Masters. My name is Aaron Dinin, I’m a serial entrepreneur and teach innovation and entrepreneurship at Duke University. I also research and study the history of the internet.

This is a podcast where the people who created some of the most impactful internet businesses, technologies, and innovations get to share their stories. Today’s guest is Joshua Schachter. In addition to being the founder of del.icio.us, you also had a few other really interesting contributions to the web that I’m excited to share with you, but before we can talk about those things. I want to tell you about something else, I think you’ll also be interested in. I wouldn’t be able to share all the amazing stories about internet businesses here on Web Masters, if it wasn’t for this podcasts sponsor Latona’s. Latona’s is a boutique mergers and acquisitions broker that facilitates the buying and selling of cashflow positive internet businesses.

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I already told you that this episodes guest Joshua Schachter did more than just create the website del.icio.us. And keep in mind, you can’t see me, but I’m putting giant air quotes around the word “just” when I say just created del.icio.us, because that’s obviously a pretty big thing, but that’s also part of what’s so interesting about Joshua’s contributions to the growth in culture of the web. It actually started a good bit before the launch of del.icio.us. In fact, Joshua was among the first people in the world hosting a personal website.

Joshua Schachter:

The web started happening while I was at college. I remember going to the lab and they had these deck station 31 hundreds with this glorious giant, one bit monochrome display and someone was running this thing with… It had pictures and texts and was scrolling and it was Mosaic. And I remember asking what is that? They told me Mosaic, being a very early web browser. And I thought that was cool. And I had actually managed to scrounge up enough money at the time to buy a older generation SPARCstation. I think it was a SPARCstation 1+, which was slow even in like 1994. I was an administrator on it, unlike the school computers. And I set up NCSA HTTPd.

Aaron Dinin:

FYI, NCSA stands for National Center for Supercomputing Applications and NCSA HTTPd was an early type of web server from 1993, that was actually the dominant web server on the internet until Apache rapidly surpassed it in around 1996.

Joshua Schachter:

I had to figure out how to first compile the compiler or get the compiler working, then build the tool chain, and then build the server. I actually got an NCSA HTTPd running and started put up a early website. And it was so early that merely starting up the web server was enough to get listed in the NCSA what’s new weekly webpage. When they listed all of the web servers on the internet, in a little blog format and it was probably a dozen a day tops. That’s where I started learning about the web and figuring out how to build very simple web apps. I think the first thing I ever built was the internet shit list where you could put things on the shit list. The idea being there as a single official shit list that people could add things to. And I made a very poor architectural choice and not long after putting it up, it wiped itself out, so that was the end of the shit list.

Aaron Dinin:

I mean, I think now we just call the internet the shit list, right?

Joshua Schachter:

Well now I just tweet everything I’m unhappy with, which is everything.

Aaron Dinin:

As you heard, Joshua was literally launching a personal website back when there was still a directory listing all the new websites getting launched that week. How quaint is that. These days it’s hard to get exact stats on the number of new websites being launched each week, but there are currently an estimated 2 billion websites in the world give or take a half billion. Being early enough to get himself listed in a comprehensive director of newly launched websites seems to make Joshua an early adopter. At least it does in my book. Now that early experience on the web is also what got him a job being well, an early web master.

Joshua Schachter:

My first job, I actually interviewed at a bank and got a job as webmaster. Graduated, but didn’t leave Pittsburgh and was running the website for a bank. This is sort of back when it was all informational. There wasn’t online banking yet, and this would have been 1996. And then I ended up getting recruited onto Wall Street and leaving the web behind and moving to New York City.

Aaron Dinin:

Now here’s the cool part. While Joshua is working at the bank in New York, he starts a little side project called Memepool. Memepool goes on to become one of the most popular web logs of the early internet. And yes, I’m intentionally calling it a web log instead of a blog, because Memepool was launched in 1998 and the word blog didn’t even exist until 1999.

Joshua Schachter:

They started that up and it was pretty heavy traffic. It got like a million hits a month, and that was a long time ago, that was a ton of traffic. I remember getting booted off hosts because a million hits was too much traffic for them. And I remember that someone decided to get all the bloggers in New York City, except they weren’t called that yet, and it was weblog going by Peter Merholz. And I remember he was at a dinner that like all of the bloggers in New York City went to, it was only like two tables worth of people.

Aaron Dinin:

Again, when I say Joshua was contributing to early web culture, I mean, super early web culture and Memepool had a significant following for its unique brand of eclectic and weird content.

Joshua Schachter:

Memepool was this sort of very terse multi-author blog. There was no identity, but there was probably 20 or 30 sort of regulars posting stuff on it. And it was just a couple of sentences about some weird thing over and over again. Some absurd thing on the internet, the world’s largest doorknob collection.

Aaron Dinin:

Memepool was also the foundation for what would eventually become del.icio.us. In other words, as happens often in the world of innovation, the really big paradigm shifting technologies, don’t just spring up from nothing. Instead, they’re evolutions that usually develop out of some precursor with vague hints of what the new technology might ultimately become.

Joshua Schachter:

People would send in links to Memepool saying, Hey, you should write up this crazy thing I’ve found. And I get three or four a day and I didn’t know what to do with them, so I actually had a text file in my home directory that I would add them to, this file called links. That was eventually 20, 30,000 lines long. I wrote a web based tool so that if someone sent me a link, I could click a bookmarklet, which was a little bit of JavaScript in a bookmark. And it would go to a new page and submit the title and URL of the page I was on and bookmark it, right. I’d be at work. I would read my email like, huh, that’s interesting. Okay, I’ll look at it later. Snap it into the software that I wrote. It would grab the URL of the page and save it off. I made it so that there was nothing private in the bookmarks.

I could send the summary of the links to somebody else. And then it turned out that the bookmarking thing had as much traffic as the blog. It was just me using it, it wasn’t multiplayer at the time, so 10, 20,000 users a day were logging in and reading the various weird crap I found on the internet.

Aaron Dinin:

Did you hear what Joshua revealed. He just explained how he invented social bookmarking. Bookmarking of course existed early on in web history. It was how people saved the websites they thought were interesting and might want to come back to. Social bookmarking meant saving your bookmarks in a public space, so other people could see what websites you were interested in and might want to come back to. And Joshua was the first person to do it. Social bookmarking was of course the phenomenon that would go on to become the foundation for del.icio.us. And we’re going to learn more about that in a minute or so, but before we do, I want to share something even cooler happening at the time, though it wasn’t as obvious in the moment while social bookmarking is no longer as culturally relevant as it was during the peak of del.icio.us’s popularity. Joshua was actually inventing something else that remains important to this very day. And there’s a good chance you probably use it a lot.

Joshua Schachter:

The original version of the links.txt file, there was a little room to write notes. My format was the URL and then I’d type notes, and the notes were often very short so I would write #Wi-Fi. And that was the first tag. I remember someone said, Hey, have you heard about this Wi-Fi thing? And I said, yeah, I’ve been tracking it for a few months. And then I would grep #Wi-Fi links and it would give just 10 or so links. And I’d often send here’s everything I know about this topic. When I made the software version of the links textfile, I made it so that I could link to everything with one tag, like here are all the Wi-Fi links. And I actually called this thing Muxway. I don’t remember exactly why.

Aaron Dinin:

And that right there was the invention of tags online. How cool would it be the person who invented tagging.

Joshua Schachter:

Curiously enough, I actually many years later interviewed for search at Instagram, but they didn’t find my experience very relevant. Which I thought was completely hilarious, so that didn’t go anywhere.

Aaron Dinin:

How about that? The person who literally invented searching by tags didn’t have enough relevant experience for tag based searching at Instagram. Talk about some high standards. Regardless, as cool as it is to be able to say, I invented tagging. There’s really no business in that. The business was in Joshua’s Muxway tool and social bookmarking, so that’s what he started focusing on.

Joshua Schachter:

When Memepool started to wane in popularity. I’m like, I feel like I should revitalize it somehow. Peter who started del.icio.us with me said, well, why not do something between Muxway and Myspace? Or maybe it was Friendster? I don’t remember a social version. And I thought that was a good idea and I started building that.

Aaron Dinin:

And that’s how he started building del.icio.us. Now obviously I keep calling it del.icio.us because, well, that was the name of the site. Unfortunately saying the name of the site allowed in a podcast glosses over it. You get another important contribution Joshua made to internet culture. You’ll see the site wasn’t originally delicious.com. It was just del.icio.us and del.icio.us was actually a full domain name, spelled D-E-L.I-C-I-O.U-S, so the actual TLD top level domain is .US, which is the United States country code. And then the domain is I-C-I-O.U-S and then D-E-L is actually a sub domain. Altogether that spells del.icio.us, it’s what’s called a domain hack. And Joshua appears to be the person who invented the concept or at the very least he’s the person who popularized it.

Joshua Schachter:

I had also always had a habit of getting weird domain names in like 1996 Tonga, the first country TLD did open registrations. I thought about .TO, what’s the funniest word that ends in TO. And it occurred to me that burrito was the funniest thing, so I registered B-U-R-R-I.TO. And I remember getting hate mail, like people like you’re using up space on the internet for stupid things. And then my friends were like, Oh, you should sell that to Taco Bell for a $10,000 or whatever. A few years later .US became available. And I thought, what’s the funniest thing I could do with .US, so I actually wrote a quick little program, a shell script to look at the dictionary. Not just look for words that end in US for every word that ends in US chop off the last six letters. And I calculated that ICOUS. I-C-I-O.US had the most words that can be created, so I registered icious and acious ACIO.US and I think someone else got itio.us.

I could actually make all kinds of things like vicious and suspicious, and so on, and so forth. Later on when del.icio.us was a company, we actually set up a development site, which was running the beta software and it was actually @suspicious.

Aaron Dinin:

Okay, so you have launched this site called del.icio.us, and then what? How’d you get people to actually start using it?

Joshua Schachter:

This Muxway thing, it had a fair amount of traffic, 10, 20,000 users a day. I was still using it. I hadn’t actually switched to del.icio.us yet. And then I wrote a note at the bottom, get your own Muxway here and you’d go to del.icio.us and get one. I got an acquisition offer from Yahoo!, and then I started talking to some VCs. And when I started talking to them, I already had 20,000 users. del.icio.us, made it to 40,000 users in 30 days, it doubled in size. And then I took venture funding at that point, so I raised $1 million from Union Square Ventures.

Aaron Dinin:

And can you give us a bit of historical context here? del.icio.us, obviously didn’t invent bookmarking, so who else was playing in the space?

Joshua Schachter:

I think Yahoo! had toolbar bookmarks, and I forget the name of Ari Paparo’s site, but none of them were social. They didn’t have significant social components. In fact, del.icio.us didn’t have a private bookmark until after the acquisition, 2006 probably, it was all social.

Aaron Dinin:

That was kind of the key feature though, right? Because say this would have been 2003, so it’s before social networking really becomes mainstream. And it’s almost like the precursor or maybe a stepping stone into the web 2.0 social media revolution.

Joshua Schachter:

I do think there was Friendster, but there was no wall, there was no timeline of stuff happening. I think friend feed sort of pioneered that. The core of web 2.0 was sort of del.icio.us, Flickr, Upcoming.

Aaron Dinin:

Here we’ve got Joshua again. Now helping basically invent web 2.0. Seriously, talking to this guy makes me feel like I’ve done nothing useful in my life. But anyway, it becomes clear pretty quickly that del.icio.us is a big hit. People really want to be able to share their favorite bookmarks with the world. When I asked Joshua why it was so popular, he got interestingly philosophical.

Joshua Schachter:

It was a product that humans desperately want it to be able to use, right? The users loved it, they needed it. And I think that I managed to harness one of those key drivers, not just a thing that people think they want, but they desperately know that they need. They want to remember better, they want to be more productive. There’s a lot of things that people want to be better at that you can amplify. I mean, that’s something I spent a lot of time thinking about, which is how do you augment people? The idea for del.icio.us was something like a memory is something that I save and then recall later they both have to be me. It turns out to not be true, right? And someone else might save off a thing that is the memory that I wanted to recall.

Aaron Dinin:

Not only is Joshua, right? The desire to take better notes and have better memory. Isn’t even a recent phenomenon. For example, there’s a play you’ve probably heard of called Hamlet by a playwright you’ve also probably heard of called William Shakespeare, ringing a bell. Now bear with me for a minute, for this example, to make sense. I promise you don’t have to remember everything from your 10th grade English class. All you have to remember is the basic plot. Hamlet’s father the King was killed by Hamlet’s uncle who you usurps the throne and marries Hamlet’s mother, you know the usual. Near the beginning of the play, the ghost of the murdered King visits his son, explains what happens and commands Hamlet to avenge his death. As the ghost of the King vanishes. His final words to his son are remember me to which Hamlet replies.

Hamlet:

Remember thee? Ay, thou poor ghost, while memory holds a seat. In this distracted globe. Remember thee? From the table of my memory. I’ll wipe away all trivial fond records. All saws of books, all forms, all pressures past. That youth and observation copied there. And thy commandment all alone shall live. Within the book and volume of my brain. Unmixed with baser matter.

Aaron Dinin:

Here we’ve got Hamlet assuring the vanished ghost of his dead father, that he’s going to do everything in his power to remember him and his final request. One of the things he says he’s going to do is wipe away the table of his otherwise cluttered memory. To a 21st century audience, that would seem to mean something like wiping off a messy kitchen table or a desk to keep it clear of kind of all the other distractions, but to Shakespeare’s Elizabethan audience a table was actually a state of the art memory device. It was a pocket sized Almanac with blank pages that were specially coded, so they could be written on with a metal stylist and then erased with a sponge later. They were hugely popular in Shakespeare’s lifetime.

Aaron Dinin:

As a way of you guessed it, helping remember important things, like say remembering to kill your uncle who murdered your father and married your mother. Which is good because it can be easy to forget those kinds of things. Anyway, hopefully you get the point. Even back in Shakespeare’s day, people were turning toward technology to help them remember important things, which is exactly why according to Joshua people loved del.icio.us.

Joshua Schachter:

Lots of consumer products, especially for free sign up consumer products are driven by our emotional state rather than intellectual needs, right? People worry about losing their bookmarks. They want to save things for later, they want to be able to recall stuff, they want to be able to get their notes back later, right? We’ve seen billions of dollars worth of companies start and exist in this space. Evernote, I always say Moleskine, but apparently that’s not how you pronounce Moleskine. Anyway… People want better tooling.

Aaron Dinin:

But it wasn’t just about improving people’s own memories, was it? Because these bookmarks were public, it was social bookmarking, so are you trying to say del.icio.us was valuable because it allowed people to share memories?

Joshua Schachter:

Well, what was interesting was there was a fundamental tension between saving and sharing that I never really resolved and I think never really has been resolved, right? When people put tags on stuff, the way I intended it was when you tag something, it’s like you’re saving off the search terms you might use to find this again. Even when I email people now, I put stuff in the subject line so that they can find this email later, so I can find this email later, right? del.icio.us was first and foremost, a way for you to talk to your future self, and you typically don’t spam your future self.

Aaron Dinin:

Even though the content was shareable, and that was like the unique thing about del.icio.us, you think the biggest value was still helping users store stuff for with themselves? I mean, I guess what I’m wondering here is what made this a valuable business to build, as opposed to just kind of an interesting tool to use?

Joshua Schachter:

After Yahoo! acquired it. And we had real researchers, we realized that it was basically this great source of human attention data. Stuff that people bookmarked was like 100X, more likely to be a high quality page in search. It was beyond just what the people do, but what do people worry about having access to again later?

Aaron Dinin:

Okay. I’m glad you brought up the Yahoo! acquisition because that’s a huge part of the story, right? I mean, del.icio.us was bought by Yahoo! relatively quickly, if I’m remembering correctly.

Joshua Schachter:

At the beginning of 2005, I think I had already had two acquisition offers, at that point. We raised the million dollars from Union Square Ventures. I started hiring, I think we had another five, six, seven, eight acquisition offers, or connections, or someone was interested in buying the data, or the company and so on and the numbers were going up quickly. We made it to about eight people. And at the end of 2005, someone came back with a much more serious offer, ended up in proper conversations with Yahoo!. I spent the entire time just trying to get behind scaling, but I think that the company was only a company for like eight months.

Aaron Dinin:

And why did you sell so quickly as opposed to keep building it on your own? Was it money, or resources, or something else?

Joshua Schachter:

It was definitely a resource constraint. We had started fundraising again, even then… I mean, it’s hilarious, the numbers were so different. Our first raise was $1 million on a $3 million evaluation. We were looking for, I think, three on seven for our series B. And we did not have a great time of fundraising, even though the growth was crazy. I mean, I remember we pitched Kleiner Perkins and they’re like, isn’t this just Search? And meanwhile, in 2020 we know just search is a fantastic thing to have been, but the shine was a bit off the rose on Search for whatever reason at the time, so we did not have awesome offers. If I recall it was something like Microsoft had a very direct conversation and then Yahoo! got wind of that. People who knew what Search was worth were very interested. And at the same time the fundraising went not awesome.

It had only been a couple of months, so if we’d started doing advertising or turning on revenue and it didn’t go awesome, that would have lowered the value of the enterprise, right? It was sort of tactical do we start advertising now or not. And we decided not, we had acquisition interest, so that’s the direction I decided to go in.

Aaron Dinin:

And what was it like trying to continue building inside of Yahoo!?

Joshua Schachter:

I stayed at Yahoo! for two more years. Yahoo! made a lot of big promises over in technology, and resources, and so on and so forth. And I was sort of tired of getting up at two in the morning and rebooting the servers. And our ops guy was at band practice and couldn’t bring the site back up and that kind of stuff. I was sort of worn out at that point. I continued running product for a while. Yahoo! obviously did not have a great track record on not interfering with this kind of stuff, so it was tough.

Aaron Dinin:

Doing a bit of math here, if Yahoo! acquired del.icio.us in 2005 and Joshua stayed around for a couple of years to run it, that brings us to late 2007 or early 2008 when he left, according to an archived post I found from the del.icio.us blog by 2008, they claimed to have a bit over 5 million users. 5 million users in 2008, wasn’t nothing. Heck, 5 million users in 2020, isn’t nothing. But by 2011, Yahoo! had sold del.icio.us to another company, so I guess whatever happened between 2008 and 2011, it’s safe to say del.icio.us didn’t fit into Yahoo!’s overall strategy, which looking at Yahoo!’s trajectory might be more an indictment of Yahoo! than del.icio.us. After that the company bounced around for a while as different people tried to rekindle its once loyal following all the while Joshua’s actually been keeping a little bit of an eye on it.

Joshua Schachter:

Yahoo! tried to sell it back to me. And they wanted a huge amount of money with no understanding of how venture capital actually works. This is something I’ve found repeatedly is that big Corp’s don’t actually understand how VC works at all. Oh, you’ll buy it for this much. And I’m like, okay, well I would have to raise twice as much as that because the company would need money to operate with, so they ended up selling it and weirdly they sold it at a much lower price to the YouTube guys, Chad Hurley and Steve Chen formed a company called Avos and bought del.icio.us from Yahoo!. And they ran with it for a bit and they tried to make it into something like Pinterest, I guess.

They sold it to a sort of venture firm in LA called Science, and they tried to make a run with it and then they sold it to some guy in Vancouver. They stripped the domain name from it. They kept del.icio.us.com and sold the rest of it for some reason. And then the guy in Vancouver couldn’t run it, so they sold it to Maciej Cegłowski who runs Pinboard. I’ve been friends with Maciej since before del.icio.us. He’s got it now and Pinboard is basically del.icio.us as it once was.

Aaron Dinin:

For all you former del.icio.us fans out there still hoping to scratch that social bookmarking itch, I guess check out Pinboard. For everyone else Joshua seems to think that even though the age of social bookmarking is past, the fundamental principles are alive and well.

Joshua Schachter:

I think that people’s memory is still important and that there’s still an opportunity to build shared memory amongst people. Products of that era of that idea like Wikipedia still are going very strong, right? Others are forums. YouTube is a wonderful repository to learn how to do something, so I think the idea is still with us. I figured something out or I memorized something and someone else can recall it. We see that lots of places, so I think this was an early version of this collective augmented intelligence. And I think we’ll see more of that. del.icio.us was just the first pass at the idea, there will be others. We’re seeing sort of the next generation now and we’ll see more.

Aaron Dinin:

Out of curiosity. Do you ever find yourself looking back and thinking maybe del.icio.us could have been more? Is there something you I guess, could have done that maybe kept it going?

Joshua Schachter:

del.icio.us never had comments. If I had added comments, del.icio.us would have been 10, 20 times more active just in terms of people fighting, and discussing stuff, and so on, and so forth. I wonder if that was not the critical mistake that it would have been a much bigger thing if I had been okay with people fighting it out, right. And we see this now clearly on Facebook where the entire value of that platform is that people hate each other mostly, people hate each other at scale. The problem I wouldn’t have been proud of having built that product. I remember when Digg, remember Digg, you could upvote or downvote things. And when they expanded from tech to politics, they found that people who disagreed with the politics stuff would try and delete and downvote stuff that they disagreed with, rather than they didn’t think it was interesting.

Joshua Schachter:

And they could never resolve that fight. And even then it was sort of obvious to me that that essential conflict was actually a driver of traffic that could be harnessed. They just sort of flubbed it. And I sort of decided to avoid it. My core thought was that it was a memory product. And if someone could show up and take a shit inside your brain, that’s a problem, right? That makes people hate your product a bit. I had always made the decision to make the product that was harmonious, not the one that was the biggest, fastest, traffic-iest thing. And that was probably my mistake, but I think I could have profited it, but lost the soul of the product.

Aaron Dinin:

There’s definitely something strange about hearing the founder of a wildly popular social media app say he’d rather sacrifice growth in order to preserve the soul of his product. And quite frankly, I think I speak for a lot of people when I say I kind of wish it’s something I heard more often. But let’s save that discussion for a future episode. For now I want to thank my guest Joshua Schachter for taking the time to share the story of del.icio.us. If you’d like to see what he’s up to these days, you can find him on Twitter. He’s @joshu. I also want to thank our sound engineer, Ryan Higgs. And of course I want to thank our sponsor Latona’s. If you’re interested in buying or selling an internet business, be sure to check out latonas.com.

And if you’re interested in reading more about entrepreneurship, you can find me on Twitter. I’m @AaronDinin, that’s A-A-R-O-N-D-I-N-I-N. Or you can search my name on medium.com to find all my articles about startups, sales, marketing, business, fundraising, any of those kinds of things. The podcast is on Twitter too, so find us there to send any feedback you’ve got on this episode. We’re @WebMastersPod. And if you enjoyed the episode, be sure you’re subscribed. Maybe even leave us a great review on your podcasting app of choice. And we’d really love it if you told your friends or honestly you could tell your enemies too. We’re not that picky. We think everyone deserves to hear these stories and that’s why we’ll be back again soon with another episode featuring another amazing web entrepreneur. Until then well, I guess it’s time for me to sign off.

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