Tech Brew Ride Home - (Bonus) Joshua Schachter And The del.icio.us Story

Episode Date: October 24, 2020

Joshua Schachter is mostly known these days as a prominent angel investor, but his claim to fame is as the founder of del.icio.us, one of THE sites and startups that convinced me and a lot of other people that the internet space wasn’t dead, in the wake of the dotcom bubble. So, consider this in the spirt of the longreads. A profile of a key startup and entrepreneur, that got the web and the world to where we are today. Sponsors: BitTrustIRA.com/techmeme Monday.com/ride NewYorker.com/techmeme Learn more about your ad choices. Visit megaphone.fm/adchoices

On April 4th, 2023, around 2 in the morning, a man was found stabbed multiple times on a sidewalk in downtown San Francisco. Hey, who did this to you? What happened next turned the story into a political firestorm. Reports have identified the victim as Bob Lee, the founder of Cash App. From Bloomberg Podcasts, this is Foundering, the Killing of Bob Lee, beginning April 16. Welcome to another weekend bonus episode of the Tech Meme Right Home. I'm Brian McCullough. So if you've been listening to this show long enough, then you probably know I got my start in podcasting about seven years ago with the Internet History podcast. I did 200 episodes. My book, How the Internet Happened, came out of that podcast. And in many ways, this podcast came out of that whole project. But I haven't done an episode of IHP in over a year. Folks kept asking me if it was dead. And I was like, it's not. dead when I find the time, when someone is available that I couldn't resist talking to, I would do more episodes. Well, that time is now. Joshua Shactor is mostly known these days

as a prominent angel investor, but his original claim to fame is as the founder of Delicious. One of these sites and startups that convinced me, and a lot of other people, that the internet space wasn't dead in the wake of the whole dot-com bubble bursting. So consider this in the spirit of the weekend long reads, a profile of a key startup. and key entrepreneur that got the web and the world to where we are today. I'm just going to drop the full Internet History podcast episode in here now. If you like what you hear and you've never listened to the Internet History Podcast, you're in luck.

Something around 300 hours of binging is waiting for you. Internet History Podcast. Enjoy. Welcome to the Internet History Podcast. I'm your host, Brian McCullough. So yeah, it's been a while. Over a year, in fact. since we did an episode of the show. Thank you, all of you who asked me when this podcast was coming

back, asked me if it was dead, it is not dead, it was just resting. I kept saying that when I found the time and when someone approached me that I absolutely couldn't refuse, I would take this out for a spin once again, and here we are. And for very good reason, Joshua Shactor, founder of Delicious, is someone I've wanted to talk to from the very first day of this project. As we'll discuss, Delicious was such a standard bearer of the Web 2.0 era of user-generated content of sharing long before Facebook or Twitter or any of that. If my email chain is to be believed, this episode has been over five years in the making. And I'm glad Josh and I finally found the time to put this together and have this conversation. As ever, if you've missed me, I don't know why you have.

I do a podcast every single day on tech news. It's called the TechMeme Ride Home podcast. Search for Ride Home, and you should be able to find it. In the meantime, thank you, Josh, for getting this show out of quasi-retirement. Please enjoy. Joshua Shachter, thanks for coming on the Internet History podcast. Good to be here. It's been a long time coming. It's, in fact, I kind of forget how I used to go into these. But the best way to do it often is, like, Do you remember the first time, what was your first exposure to either the internet or the web? The internet would have been, as an undergraduate, was sort of before the web. I remember, you know, I used USNet. CMU had a fairly active internal USNet, which they called bulletin boards, B boards. We had instant messaging at school and across a couple of universities. It was a thing out of MIT called Zephyr that was sort of years before IM was popular.

I remember Gofer and FTP sites and all that stuff. So, you know, I was a couple of years. I was online a couple of years before I saw a web browser. which was, I remember I was at, I was in, I was in Wien Hall at CMU, which was, because they had the, the deck stations with the really big monochrome screens, so tons of text. You know, it was like 1024 by 768, which is gigantic for the era. And they had these giant screens, and I was there, and I saw someone who had this crazy application, like, you know, like, you know, I mean, it was, the computer. had graphics, but they weren't like, the stuff you did wasn't very graphical. It was just, you know, X terms and you're editing text mostly.

And I remember seeing someone scrolling through, you know, something with pictures and stuff. And I'm like, what's that? And they're like, oh, this is mosaic. So I actually do remember the first time I saw a web browser. Well, and that's interesting because, you know, again, there were things like gopher, and stuff at the time so that, other people have said that. They're like, the web was introduced to me as mosaic as maybe, you know, this was this. I might have known it was a client, but I thought this was this other thing that was mostly

involved with pictures and things like that. I mean, I figured out how it worked and, like, I ended up setting up a web server. Like, I had saved up over the summers and bought myself like a used spark station. Spark 1 and I had a machine so it wasn't just that I was a user but I could actually have a place to run administrative tools and so on. So I actually downloaded NCSA, HTTPD and you know, within a year, I was like, you know, what's a CGI script and what's a, you know, how do I build this stuff? And I, you know, how do I run a web server, that kind of stuff? So very early on, I, sort of figured out what the web was a protocol and not, you know, mosaic.

What were you, what were you putting on that server? Home directories and, you know, stuff like that. It wasn't super anything sophisticated. I remember we, we got listed on the NCSA, what's new page as a student, student server, you know, a million years ago. you know, like very early on, you know, there wasn't that much to do. It was mostly text.

We made, a friend of mine made in the official internet shit list, and anyone could add things to the shit list. And because of a poor architectural design, it ruined itself fairly quickly, so we took that down. So, you know, We built a bunch of sort of weird garbage to play with it. You were going to school for electrical and computer engineering, right? Yeah.

If this is not, if this is jumping over stuff too much, you end up on Wall Street, right, in your career? Or did you do any sort of, did you dabble in any sort of like, you know, let me start a small design firm or something like. everyone was doing sort of side gigs like that on the web. I ended up at a bank doing, you know, running the web stuff for a bank. What sort of year would that be? That would have been 96. So, and then I ended up getting recruited out of that fairly quickly, leaving Pittsburgh and getting recruited to New York City,

not doing web stuff really at all at a brokerage. When you say that the banks were doing web stuff early on, was it just the sort of we're putting up a placeholder here? Or I think I've gone into this with a couple people in the past. It was a few years before anyone was bold enough to try to put accounts and stuff like that. It was not online banking. Yeah. It was just a web page.

And by 97, like I said, in 97, early 97, I think I got recruited to a brokerage and moved to New York City and started doing financial stuff and wasn't doing public web stuff at all. Were you a quant as the term is? I was started as a developer working for a trading desk and then I left that bank and went to Morgan Stanley and I was a quant. All right, so then again, please interrupt me if I'm missing anything important here. And I actually don't know the chronology here in terms of Meanpool and GeoURL. Mean pool came first, right? That's still in the 90s. Yeah, I think I started Meanpool in 1998 or so. It was, you know, Meanpool was a very early, I guess would have been called,

called blog. However, that word didn't exist. There wasn't RSS feeds. I ended up, I think when I wrote it in in 97 or 98, like SQL databases weren't easily available, so I had to write my own sort of faux database to generate the site. Yeah, so 97, I think I did URL in the early 2000s, so much later. Okay, right. So then let's focus on Meanpool right now because the way in my poking around what I could find about it, it sounded to me like a link blog, like just things where it's like, hey, I found something interesting, here you go. Yeah, it was sort of a very terse blog. It wasn't a link, it wasn't one link per, but it was just a couple of links in a short

paragraph with a couple of, you know, 20 or so authors. And it was fairly big in its day. I mean, it was, you know, I think at one point it was doing a million hits a month when that was actually like pretty substantial. And an edgy magazine that I won't name tried to hire me, you know, to do the same sort of thing for them. So, you know, it was basically, you know, the, you know, the, weird edges of the internet.

When, uh, if this is like 98, 99 or whatever, are you throwing up, um, you know, banner ads and stuff. I mean, that, that was kind of hard to do because there weren't networks and stuff even, uh, for a long time where you could just throw banner ads and stuff up. But was that earning you any money at all or was it just a thing? No, I, we never, we never did ads. Um, so it was just, uh, you know, it was always, I always, uh, wasn't sure what the, uh, the issues would be with having a job at the same time as earning money elsewhere, especially when you're in finance.

So I just didn't do it. Well, and also this is the time period where that was a huge controversy, the idea that someone could be outed for having this website in the background that maybe your boss wouldn't approve of or something like that. You weren't doing it suit anonymously. No, I wasn't. I did it as a, you know, I didn't keep it. secret.

I, you know, at, um, uh, at, uh, at, at the first company in New York, I didn't tell anyone, but, but later on, like when I was at Morgan, nobody cared that much. Um, but, you know, Mimple was already getting sort of long in the tooth, um, at that point. Um, I went to Morgan, I think in 2000. Um, um, so they didn't, they didn't care too much.

I wasn't paying a huge amount of attention to it. In 2001, 2001, I started building a tool. So what happened is that people would send in links into MemePool. Like, hey, write about this. And many of them were interesting. And I'm like, this is good. I'll write this up at some point. And I'd put it in a text file.

And I had this, ended up having this 20,000 line text file. that had lots of interesting things in it. And that sort of turned into a thing I built called Muxway, which was Delicious's predecessor. It was essentially the same, except it had more functionality than Delicious itself did. For example, it could pull the pictures out of a page and show them visually, which was kind of cool.

I sort of regret not following up on that because we know Pinterest came from that same sort of idea. But I built this, you know, I sort of paid more attention to Muxway. You know, that was probably 2000, 2001, and 2002 I started writing Delicious, which was a multi, you know, after I saw that Muxway was getting more, you know, so basically Muxway was very similar to Delicious. You would be on a page, you'd click a bookmarklet, it would grab the item into the page, and then you'd tag it. Right, which is, we should stop and hit on that for a second.

So the idea of tagging it was just for your own self-organization stuff. Correct, and that came out of that text file, in fact. The text file basically had... You know, it was just one link on a line, and then sometimes I would write a comment, which is a hash mark in Unix lingo. I would put a comment and then type in some notes, maybe some text, but often it was just a single word. So I remember when Wi-Fi started to be a thing, and I was like, oh, that's an interesting article about Wi-Fi, you know. So I would paste the URL and then I would just hit space and they write hash Wi-Fi. And I remember a friend of mine sent me a thing and said,

hey, have you heard about this Wi-Fi thing? And I'm like, yeah, I've been tracking it for a bit. Here's everything I've collected. And you, you know, you grep, which is, you know, search, grep Wi-Fi links, links being the text file. And I would get, you know, nine links. and I just pasted it to the other person. And that's sort of the key idea behind tagging.

So very early on, I think the first tag thing that is tagged with a single word, something is hash math. Some mathematics thing. I could probably look at the file. And then the way it would work is, you know, if things had multiple tags, like that's how you... Was there any sort of hierarchy to it, like, where... if there's 11 things tagged with Wi-Fi, one is higher than the other, or is it just returning everything?

It was just a bag of things. There was no order to the collection other than time. But, I mean, you know, I've spoken at length before about the idea of ideas being in the ether, just being in the zeitgeist and things like that. And as I'm sure we'll talk about, like this, you know, tagging and taxing. taxonomies and things like that. Man, that suddenly was everywhere for a couple years. And like, so, and obviously, the tagging came in delicious sort of very early on. Like I didn't, it didn't, you know, like there was taxonomy is not a thing I invented, but for the most part, like it didn't, I didn't get inspired in that from somewhere else. There was no other progenitor of using the list of words, you know what I mean? Like everything else was full. and that kind of stuff at the time.

So what prompts you to put it up as a website as delicious? Well, I mean, what happened was, you know, like I said, I pasted the list of Wi-Fi links to somebody, and then I sort of realized that, like, I wish I could just give them a URL to my list, my list of things, right? So when I built Muxway, it was actually a public thing. Anyone could go in and look at it. And at some point, I realized that Muxway actually had more traffic than Mimple did. For people reading my links. So when despairing about what to do about Mimpool,

I was trying to think about how to reinvigorate Mimpool using something from the Muxi. idea, that sort of spawned delicious. It ended up being sort of more friendster, you know, between Friendster and McSway, you know, the social aspect, although it was a very soft social aspect. Yeah. So actually, I was thinking about that in terms of, you know, what we're talking about here and what maybe we will talk about a lot is the whole web 2.0 idea. And, you know, I'm still not entirely sure what that was, but go on. Yeah, I'll have you speak to that eventually. The idea, I was trying to think, you know, the idea being that when the, when the web sort of took off in the in the 90s, it was a lot of, well, you can put things on here, you can put pictures,

you can read things, you can buy things on here. I was trying to think of what delicious, you know, I remember being a delicious user. What it was to me was, it's sort of the hive mind sort of concept that we're so familiar with now that I want to see what everyone else thinks about whatever this, or what's important for this topic that everyone else thinks is important and things like that.

And I was trying to think, you know, that idea of reaching into someone else's mind, the thing that came to me was Napster where you would reach into someone else's music library. So the idea being that with delicious, I was reaching into other people's minds. I'm not, I'm sure that's not exactly what you were thinking of. No, that's sort of literally the idea was understanding it as a kind of exome memory. Right?

You know, my idea, which I never, you know, really got to deeply execute on because Yahoo, But the idea was that, you know, you memorize something and then you recall it later. And why does it have to be the same person in both of those events, right? So someone else can memorize something and you recall it later. Right? So the idea of group memory became very – and that was a thing that we explored very early on was having a work group version of delicious. But also, speaking of things like being of the moment,

and this was in the ether, it's the wisdom of crowd things. Wikipedia is only a few years old at this point, and obviously things like Flickr come around at the same point. So, again, my memory of it is the powerfulness of it was feeling like I could, again, This is something that I feel like we take for granted now. But I could go find a resource and expertise that I didn't have to know the providence of.

I just trusted that like this sort of aggregation of ideas was sort of, if there was enough of it, it was good to some extent that I could trust it and find value in it. Yeah. And I actually had built stuff in the system. Again, wasn't able to really release it, but the idea of measuring people's skill at organization or expertise was explicitly a thing that we were thinking about. Well, actually, we should back up for a second because I always find this valuable. To describe if I were, if I opened up a web browser in 2004 and I went to Delicious, describe for me what I could do, what it looked like, what I would function as, would I use it,

would you expect me to use it and then immediately leave because I found what I was looking for a search engine. How did it function if I was there in 2004? So in 2004 it would have been very rough. That sort of before, I think before I took venture money. So actually in 2004, there's a good chance it would have been down, simply because it was down a lot, given the amount of traffic that we got. So, in general, a given a given website is dominated by people consuming data,

right, this user-generated content where most people are reading, a much smaller proportion are creating it. Whereas on Delicious, the vast majority of users were there for their own memory and their own memory use. So something like 50-50 instead of like 90-10 or 991. So, you know, you'd go there. There'd be a web page showing some subset of

recently bookmarked things that people had shared. And often people would just go there and see interesting stuff and click it. And that's it. That's their entire use of the site. Just, you know, it wasn't just random links. It was random links that someone somewhere found interesting. The other thing that was heavily trafficked was the popular page where I actually, it wasn't actually, it was like the first derivative of popularity.

It's not what's most popular, but what was most popular recently. And apparently that ended up being a huge inspiration for Reddit later on. But that's where people looked at stuff. There were top tags of the day, which were actually always pretty stable. And you could go look at what's popular within a given tag. And that also, you know, that was sort of a, you know, for a given, like if you were into Java, What are the top Java links for today? You could see 10 interesting, almost guaranteed interesting links for whatever topic you could identify.

And as a contributor, I'm creating an account that allows me to tag things and add them myself. Well, it wasn't, you weren't a contributor, right? I mean, yes, you contributed to the mass as a, you know, as part of doing what you're doing. but largely people were doing it to save items for themselves. So you would sign up, it would give you a bookmarklet, which was fairly hard to install. So that people who were not sufficiently technically savvy couldn't get it working. So that caused a certain bias in the user base.

But basically you'd install the bookmarklets, then you'd go to some random web page, like, ah, you know, I'm going to save this for later. And you'd fire the bookmarklet. And it would pop into Delicious, into a form on Delicious with the page already filled out, the URL in the title, in a form. And then you would, the cursor was already put in the notes, or put in the tags area. And you could say, so you'd click the button and say, this is about Java and web, hit return, and it would drop pop you right back into the page. I remember having that bookmark and the stumble upon bookmarklet.

What about the idea of being able, you know, I'm talking about getting into people's heads, the idea of following what other people were bookmarking? Following came later. We did, you know, it's interesting. We built a version, a more social version. That would have been 05 or 06. We did have the inbox where you could subscribe to a tag, a person slash tag, or a person. And we sort of rename that to following.

The inbox was always a problematic, just architecturally very difficult to work with. But, yeah, basically you could follow, you could see what other people were doing. We didn't call it follow at the time. But we did, it was asymmetric follow, which wasn't really a thing in the social web until, you know, Twitter became big, right? In the past, you know, you would add someone as a friend and they had to accept you. So we did follow, but it wasn't, you know, just follow any source of stuff, basically. I want to contextualize again. So we're talking 2004, 2005, we'll talk about in a second, you know, you're taking BC.

money and trying to really professionalize this. But, um, yeah, we took VC money in 05, early 05. Right. The, the idea being that, again, uh, you know, friendsters there and there's things like aim where, you know, you have to make these connections. Um, you have to, both sides have to agree or whatever. Um, but things like Flickr, things like this, where again, you're saying it's asynchronous like Twitter where it's like I don't asymmetric right sorry sorry sorry I only have to I only have to

you didn't call it following but whatever this tag is that that I'm if I'm interested in Java I can just we're using the term now follow it subscribe to it whatever yeah exactly so that idea that again it's almost like the interests and the memes sort of self-o organize themselves and you find what you're interested in. And then that's how you're, it's the first thing that I can remember of yourself organizing your interest. And we do that for all of media now, where it's, you know, it's not, the days are long gone where we all listen to the same radio station or watch the same TV shows or whatever. Everything is now, I'm curating my own interests and my own whatever.

Right. I mean, if you think about what's happened with media, you know, the, basically the things are exploding into their constituent pieces, right? You know, remember, remember when YouTube got big? This would have been 0506, right? You know, it used to be that if you wanted to see something funny, you'd watch Saturday Night Live. And what happened was that the only the funny bits from Saturday Night Live, which, you know, were less than the whole, would end up on YouTube and someone would email you a link to a YouTube video like, oh, look at this. And it's just the funny scene, right? So this is sort of happening with everything, right? Newspapers exploded into articles and journalists, and you see that now in 2020, right? journalists are leaving newspapers to start their own brand because the aggregation isn't necessarily more valuable than, you know, you can sort of think of it as, as, you know, peak, right? So when you, you know, if you're buying industrial power or industrial bandwidth, you're only billed on like the top 95 percent, right? Your value is only the top peak traffic that that thing got, right? The most popular thing that you wrote recently. So, um,

figuring out, you know, how to navigate that world means that that media started exploding into smaller, more mobile pieces, right? So it only sort of makes sense that if there's lots more pieces, previously the people who were creating the content were also organizing it. But now there's so much more of it that there is this curator role that lots of people play, tastemakers and heavy. retweeters and so on and so forth, right? So you don't just subscribe to content makers, but you subscribe to these creators. Influencers, influencers. Yeah.

Yeah. The, so as we said, I guess you quit your day job at Morgan Stanley in early 2005. So Delishus started getting a ton of traffic. Yeah, yeah. And we should say word of mouth. Like you're not, there's, you're not investing. anything in like advertising or marketing or anything?

I think, so no, I'm not using traditional media marketing in any way. And this is actually how I met Paul Graham where he wrote an essay saying, and I remember because it was called The Submarine, where, you know, Delicious was just in an article by Businessweek and it says that they're a new growing blah, blah, blah. But what I learned from this is that Delicious hired a PR agency. And I'm like, no, actually, I didn't because I didn't have any money. However, I was sort of very deliberate that any time I made things that someone was organizing their stuff on Delicious, it was at least somewhat obvious that they were using Delicious to do it.

So, you know, if whatever they were doing was the message, I was always the same. subcarrier. Right? So if you had, you know, like I had a thing that you would put your, and again, in 2020, this doesn't fly at all, but you would put your blog username and password into Delicious and it would once a day post your bookmarks to your blog with the links to the thing. And if you tag them, links back to Delicious, right? if you had a blog widget that showed, you know, what you were doing or, you know, whatever, it would link back to Delicious, right?

So Delicious is always the carrier for the actions that you would take on it, right? You know, I made the Save This button, right? So you remember the little buttons save this on Delicious, right? I actually wrote the original patent on that. Oh, really? Yeah. I've talked about this before where all of a sudden there were dig this and saved, you know. Yeah, that came from delicious. That was just a version of the bookmarklet. I realized you could put that link just in the page. And the idea was that that would be a user acquisition method because it would say, okay, you're trying to save this. You don't have an account. Why don't you sign up? The reality was nobody clicked on those. That was more of, a performative thing from the role of the publishers, which was, please save this.

This is a thing we would like you to save and share. But, you know, I mean, a surprising number of those things from that era came from Delicious, right, to save this button, the having the username in the URL directly after the domain name. You know, it's sort of gone now, but lots of YouTube features were sort of modeled on the way delicious did stuff. Twitter still is, you know. Well, I mean, I'm thinking of, you know, the stupid like button, which, you know, I'm not, believe me, I'm not trying to be pejorative or blame you for this.

But there's a direct lineage between that. What you're describing is you're sharing your intentionality and your interests. And so. Well, the like button itself, you know, in a Facebook page or whatever, where you would click like on something, that actually came from friend feed. I'm talking about in some other site. Right, right, right. Right, it's embedded and it's like, right, you're describing a growth hack where it's in the sense that the publisher thinks that by doing this, they're going to increase their distribution. Yeah, and they didn't.

No one used them. I mean, that's the good news because they were sort of ugly. But, you know, it was a thing. People tried. But it came from us originally. All right, so early 2005, it's taking off in the sense that you're like, are people telling you you could make a business out of this? Are people knocking on your door to give you money?

What's happening? The site is doubling in size every couple of weeks or a month, and the site is always down. You know, people are giving us hardware. So, I mean, so I knew it was growing enormously. And then VCs started, I got a couple of pings from VCs. And I started exploring that, so early 2005. And it's right around.

I started talking to them a couple of months before the Flickr acquisition, because I remember the Flickr acquisition getting done while I was at talking to VCs. and then we started, we actually had, we got acquired while we were in talks with VCs to raise a second round. Because, you know, the numbers of that day were much, much, much smaller. And you're here in New York, right? Because you took money from Union Square, right? Yeah. So there's also the whole.

It was Union Square in Amazon, but yeah. But what I'm trying to point out is there's still that idea. of New York is a different place where it's harder to raise and, you know. It was also a world I wasn't really at all familiar with. I was largely disconnect. You know, I was in finance, but I didn't talk to VCs at all. I didn't know any at the time. Well, it's also a compressed period of time.

I think you quit your day job in March, and then the sale to Yahoo is December. So in that nine months... So I had been talking to VCs for months and then finally when they when they, when we reached an agreement on the term sheet, I quit my job on a Friday, sign the paperwork, started delicious on a Monday. And hired people or like how big did the team get? We started hiring people. I think we had seven or eight people, max. So someone to do ops. We actually did a tiny acquisition and to hire the guy who built that, who had built a tagging version of Craigslist that used tags.

We had, you know, a couple of engineers. Ops was super important because the site was down all the damn time. Just, you know, anytime we'd buy so. servers, I'd call up Dell, figure out what was cheap enough, buy it, rack it, set it up, and then immediately the capacity would be filled. Like, it would last a week, and then we'd have to buy servers again. And you're physically installing them. There's no AWS.

There's no push button. Oh, yeah, yeah. No, there was there. I mean, I remember when I put my hand into the fan at the top of the rack and caught a fan blade under a fingernail and had to get a tetan shot. I mean, I literally anointed that machine with blood. which I still have in a box in the basement, actually. That was Mark Andresen had sent a server out of the blue.

So I was trying to set that up. But it ended up costing me a ton because it didn't have enough parts to actually run. He has priors for doing that. I think they were sending the Yahoo guys servers from Netscape early on. Or maybe it was the reverse. Maybe it was, yeah, I don't remember. Anyway, so in the nine months where, okay, we're taking some money, we're going to do a business out of this. Do you have any idea of a business model, business plan?

So we were just trying to keep the site up for the most part. Like maybe add features sometimes. You know, we were able to do a bunch of sort of little superficial stuff. Like we built a thing that turned a set of bookmarks of MP3s into a podcast and all sorts of things like that. But that wasn't core engineering. Like I was basically doing core engineering to bring the thing to scale over and over again. It just grew so fast. We thought about doing advertising or something like that.

But I mean, literally we raised in March, spent most of the time trying to scale the thing. And we had like a bunch of employees and stuff. And I was trying to figure out how to hire. We started raising again sort of six months later. That went pretty poorly. You know, what's it? It wasn't clear that Google was going to be the blockbuster hit that it was. So a bunch of VCs were like, this is just search.

Why is that interesting? Which is, you know, in retrospect, hilarious. Even that late, yeah. Yeah. I mean, I did a week on Sand Hill Road, which is where all the VCs are. We ended up getting two term sheets, one from a New York fund and one from a San Francisco fund. And even, you know, the first funding in Delicious was like a $1 million on a $3 million valuation, which you never see anymore, right? even not climbing, aggressively growing companies are raising, you know, at 10 or 12 pre-money

valuation frequently. So, you know, we hadn't raised very much. I'd already given a bunch of the company away. And then the big guys got wind that we were trying to raise again, and then they came in and started nosing around. So I think it was Microsoft that expressed an interest. ended up being Yahoo that ended up making an attractive offer. But I had something like 10 or 12 or 15 offers along the way.

I mean, Yahoo had made an offer before I started it as a company that was basically a sort of nice job offer. I mean, luckily, I was working at a job that paid well and I didn't have to be forced into a choice. So, well, a mutual friend of ours, I reached out to him to ask me what to ask you and or ask him what to ask you. And he said, what was the meeting with Jeff Weiner like in the wood paneled Allen and co offices? Like what was the pitch from Yahoo or what made you go with them? I mean, I was very frazzled at the time. Like the site was always down. It was just, you know, so there was a lot about, you know, We'll help you scale.

We'll help you. We have resources and so on and so forth. And I was burned. I mean, I remember once I was on a plane, I had a T-Mobile, like a danger sidekick hip-top. I forget what it was called, but that little flippy phone with a full keyboard. And I had a S-SH client on it. And I had, the site had gone down.

And I was trying to bring it back up. and I'm typing on this tiny little tiny terminal and the airline attendant is standing over me like, sir, you have to turn off your phone. And I'm like, one second, please. And I think I ran the script to reboot the site and then I turned off the thing. And the site didn't come back up.

So the site was down the entire time I was in the air, you know, three or four hours and it just had to wait. And of course, I'm, I'm, upset the entire time because I failed everybody, you know? Yeah, go ahead. No, I mean, it was, it was just, I was, I was frazzled. What I'm trying to get towards is why Yahoo, and I'm going to, I'm, if you'll forgive me, I will contextualize because people forget this, that after the bubble burst, like, you know,

eBay is one of the big winners and survivors, but also Yahoo in this period, does sort of resurrect itself with this sort of like Hollywood for a new generation model. It wasn't very technical, but it worked. But this is before some of that. I mean, like Google was already dominant. I mean, I remember Yahoo sort of already not being a thing by the time they did the acquisition. You know, they, you know, and again, this is, this is to me a New Yorker. not in tech in the same way that Silicon Valley was, right?

Like, I remember I had lost access to my Yahoo email address and was never able to, you know, jump through the hoops. Like, as part of the acquisition, I got my username back because I made them fix that, right? And I hadn't bothered to fix it because I could, you know, it was too much work, right? I kept saying Google in meetings instead of Yahoo, and it took a long time to train myself not to say that,

So even then, they weren't like a super dominant powerful org, right? They had, I would say it was an attempt to regain. You know, it was already slipping heavily by that. Right. They go on this many acquisition spree that Delicious is a part of, Flickr's a part of, but I feel like there was like a dozen or so in a period of like a couple years that they do. I mean, I think the three big Web 2.0-1s were upcoming Delicious Flickr. and I remember like so for example upcoming I was already friends with Andy Beow and I'm like

and he's like hey you know we got this this acquisition offer what do I do and I'm like well first you need a lawyer and he he used my lawyer right um so um you know it wasn't you know they were they were making moves at the time I remember the Flickr acquisition being sort of shocking um they were So they were trying to regain it. And then what happened was, after we got acquired, Yahoo Answers took off. And then they basically completely pivoted to focus on that and not the other stuff. So internally, there wasn't a huge amount of focus. Well, yeah, I mean, to the extent that you want to go into this or rehash it, can you tell me,

because you're with Yahoo for two or three years? Two and a half years. to the extent you want to go into Yahoo's culture, your sense of that company in that period from the inside? I mean, I pushed on people a lot. I was called a whiner a lot. And it was very frustrating because I basically went from Morgan Stanley to startup to Yahoo.

And I was frequently told, like, that's not how big companies work again and again. and I'm like, not really, because I'd been at a functional large organization, you know. So unfortunately, you know, it was a, you know, a bunch of sort of broken fiefdoms, lots of politics, not lots of getting things done. So it was a shame. And I'm not really wired for doing office politics stuff. I want to sit down, get on to the next thing, and chip, you know.

And I just remember the, you know, one week I had a not incredibly minor, but relatively minor feature that got sunk by PR and HR and legal over some stupid shit. And I'm just like, what is the, you know, and I'm judged on my ability to get things done. But you put all these people in the way. And I think large organizations tend to be like that. but you know it's I don't know

it was rough it was not something I was used to operating in and delicious just sort of withers on the vine within yah

yeah I mean they they I mean there was a bunch of sort of local politics that wasn't so much corporate stuff

so much as you know the local organization that was incredibly difficult, a bunch of stupid hurdles. So we never sort of regain the momentum. I mean, this is something I, you know, when I talk to a startup and their competitor gets acquired, I'm like, great, they're going to now spend a year fucking around arguing

with people over servers and other shit and not like actually working, right? Sort of takes them out of the game for a little bit, so it's an opportunity for you to or often permanently. And that's what happened to us. And Flickr did a better job of isolating themselves and just not tolerating Yahoo shit, I think. But, you know, I was never super close to them. So it was hard for any of that to rub off. Back to our mutual friend here.

But this is, you know, sort of the right time to ask it. With the benefit of hindsight, with, you know, however, what is it, almost 15 years now. Do you see, and this is impossible because you know what you know now, but if you could go back in time and tell 15 years ago you, is there an alternative universe where Delicious could have become a large standalone company? Yeah, I think that there is still a couple of big opportunities. There are no companies that really stand. for the user, right?

They're not, you know, like, when you, when you use a browser and connect to a server, it identifies itself. You know, my user agent is Chrome, right? And that sort of always stuck with me. Like, the browser is my user agent, right? So, so Delicious, first off, addressed a failure in, directly in the browser, in that the browsers were just not capable of dealing with large amounts of memory,

remembering lots of things for you on the web. But, you know, it's sort of very obvious in retrospect that you need amplification, right? We need mental amplification for memory, for learning, for interacting, you know, all these things. And what happened is that the browser is sort of firmly under the control of the site, right, the places you connect to, who often don't have the user's best interest at heart. So I think that there was a big opportunity, and still is, a big opportunity to be the user's agent in the world, starting in memory and extending out from there. The second is that we barely have any functional cross-person memory or organizational systems, right? you know, Slack, which is a, you know, an IRC chat room, I guess.

And it seems to be sort of, you know, across between a digital water cooler and a broken wiki. Right. And I can't, I can't, I've never had to use it in a professional sense, but I can't imagine it being, you know, a net positive for productivity. No comment. So, you know, I think that there were a bunch of opportunities there. That said, you know, a product and a company is functionally represented by the time it comes from in its context, right? So, you know, I may have played it as well as I could have given what I know at the time and my skills and, you know, what the financing environment was like, right? you know, the investors were not super excited about it. They were certainly not as excited about it as the acquirers were, right?

None of the investors for a second round came even halfway to the valuation of the acquisition. Right. So it was sort of a natural choice to turn away from doing it as a second round, just because, you know, the lack of enthusiasm of the, you know, investors. So, yeah, I'm not sure I could have played it better, but that's, you know, that's not the answer to the question. Like, what could it have turned into?

What, how big could it have been? Especially given how many of the little things we did continue to influence the way stuff is built now. Give me some of those. I mean, you still see tagging everywhere, lots of little user interface things. apparently my bitching about the way RSS worked and my initial suggestions, I had this idea of, you know, instead of just hitting a site to get the data, it'll call you back with the data. That turned into web hooks. So, you know, I see little bits of influence sort of everywhere. So it would have been nice to continue to be able to innovate and build things. you sort of mentioned this earlier

and I cut you off but you know Delicious was this sort of poster child for Web 2.0 and you said you don't even know what Web 2.0 means

so thoughts on that in terms of like being a part of this era as you're saying and a part of a startup in this time I mean we were

we were trying to build the new thing right what is what is the product that people need and want. And that's, that's, you know, sort of all I tried to do. You know, even then we're like, what the hell is Web 2.0? And I mean, I think it was just a context for explaining the world for, you know, people attending O'Reilly conferences at the time, right?

There was, you know, it was, you know, the kind of people who went to the Web 2.0 conference. Well, I feel like I've said before, it was just, it was a shorthand for telling people, the web and the internet's not over. It wasn't just a fad. It's still a thing. I mean, it's interesting because delicious at the time, at that time, it was, you know, it wasn't done yet.

It wasn't as calcified. You know, now the idea of, you know, changing the world in the context of the web is much harder, right? Like, imagine, I mean, imagine, I mean, when I can send you the screenshots for delicious, it was super rough. I had to learn C. because I wanted to put a thing on the right and not put it in tables.

You know, it was super rough when it launched and people were tolerant of that. Now, if you go to a sort of crappy looking website, people judge it because they expect things to look much better. Like the bar is higher, even though the things that we do are less, you know, more calcified closer to the, you know, you know, you see unusual things less often, right? So the audience is huger, but that audience tolerance for novelty is probably lower, right? On average. So, you know, if you do something weird,

not only does it not find its audience, but it's drowned out by something that's, you know, more flashy or even worse, designed to be abusive of people's attention and, you know, that kind of stuff. So, so it's, so, you know, I think, I think what's, what's happening is that sort of the, the, the, the attention moves elsewhere. You know, you see Web 3.0 mentioned a lot, and it was sort of jokingly said at the time, you know, when we were like, oh, we're Web 2.0, what's Web 3.0? But now, you know, people are talking about it's these these Ethereum-based distributed finance things that I'm not convinced anybody except crypto people use.

You know, and maybe that's the future, but, you know, it doesn't feel like the transformative in the same way. Or at least not yet. Maybe it's too early. I don't know. Right, right. Listen, that's my other podcast going on and on about that. Yeah. I mean, I've spent, you know, I am a, I still build things. I still write code. I am an active tech investor now. Right, right, right. I was going to say. I'm trying to keep my finger on this stuff and I still struggle on some of these things. Like, does anybody want that? For, you know, you worked at Google for a bit, advised Walmart labs, but, but mainly you've been an investor these last few years. So, yeah, I have mainly been an investor. I've,

I've built a bunch of stuff. I actually re-hired some of the original Delicious team, and we're working on some ideas. I have some crazy ideas that I'm trying to prototype. Many of them are too weird to actually be built. So that's a challenge. So see, there's no way you're going to reveal any of that to me right now, are you? If I explained what I think about it now,

I'll just sound crazy rather than clever. So, you know. But see, that's what I want to know about. But all right. Reveal it in good time. Yes. Well, I mean, the last thing we built ended up, you know, it was an interesting idea, but it ended up one of the structural ideas ended up being infeasible or in conflict with one of the other ideas.

So it didn't actually work. Right. So that's the kind of stuff I'm trying to build is prototype these interesting things. because many of them don't actually make sense. Many ideas don't make sense when you get into the details, right? And that's not always apparent when you just tell someone the idea. So I want to have a better basis of something working. I mean, that's the hard part of engineering.

Real quick before I get my favorite final question, you were an advisor to the HBO show Silicon Valley? Yes. Was that fun, crazy, interesting? What was that like? That was a lot of fun. I did probably, and everyone's like, you did a great job advising them. And like they knew what they were doing.

The questions were often very tactical. Like, do you know someone in blockchain doing this? Because we want to ask about that. And I'd make an introduction. Or, you know, I'd get snippets of scenes. Like, do you know who we're referencing in this? I'm like, yeah. The interesting bit is the producer.

told me that some of the actors were interested in angel investing and could I talk to them. And I did. And I actually dragged some of them on to some of the meetings with me, with startups. And I often wouldn't tell the startup who I was bringing. So that led to some really awesome, briefly confused reactions. That's funny. I was just listening to a podcast right before we did. did this with Kamail. He's often the Marvel universe now. But, all right, my favorite ending question, and you were sort of starting to get into this, is what are you interested in now? And it can range from, you know, some people have said, oh, it's blockchain, you know, O'Mallek, it's photography or whatever. But like, it could be business stuff. It could be

personal stuff. Like, what is the thing that you are most fascinated or passionate about? right now. So I have a couple, so my, my sort of day-to-day goof-off activity, I do plotter art. I do, I, you know, make machines and write software that draws interesting, complicated patterns. I usually tweet them. I've been trying to, I'm actually helping someone do a music video, but because the actual raw video of the music video is not available, I decided to use the the Rickroll video. And what happens is I will, you know, I'll write my code. It will run for a few hours and then I'll hit play to see the result.

And then Rickroll myself sort of full in the face repeatedly. So that's been a bit traumatic. I also run an event called self-racing cars where I, I, I, so I'm a very amateur race car driver. I drive a vehicle in the low thousands of dollars. You know, it's not like the super high-end stuff. But I'm familiar with how to operate and run a day at the track. So what I do is I actually rent out a track about three and a half hours north of San Francisco where I invite companies and startups and universities to come to the track and try to get around the track.

So that's been a lot of fun. I like robots. Who doesn't like robots? I'm not really at the point where I could be building them safely. But, you know, I sort of want to see the future of that anyway. I'm generally fascinated with robots and CNC and fabrication. So I like that a great deal. So, you know, lots of 3D printing and CNC and that kind of stuff.

Well, Josh, listen, thanks for bringing the internet history podcast back single-handedly, and thanks for coming on and remembering all that for us. Thank you.