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The internet’s homepage

For a couple of years, there was nothing on the internet so simultaneously thrilling and terrifying as having your website hit the front page of Digg. Thousands of people, maybe tens of thousands, would immediately come to your site — and there’s a good chance they’d crash it in the process. Hundreds of commenters would debate the merits of whatever you’d created or published, pick fights with you and each other about it, and make you feel like the internet’s main character. At least for a few minutes, until something bigger and newer and more controversial hit Digg.com and everyone moved on.
In its early days, Digg was something like the homepage of the internet. Any user could submit a link, and then any other user could either promote it with a “dig” or demote it with a “bury.” The best and most popular stuff made the homepage, which was seen by tens of millions of people a month. The most controversial stuff had epic comments sections.
So many of Digg’s features, from its voting mechanism to its commenting system to its occasional teeming toxicity, are omnipresent on the internet now. But in 2004, when Kevin Rose was working on the first versions of his new news platform — back when he was best known as a host on the TechTV network — it was all brand new. And what Rose and others built during that time has changed the way we all use the internet ever since.
I recently chatted with Rose, who is now a podcaster and investor, about why he built Digg the way he did and why he felt like giving users transparency and control was so important. We also talked about the legacy of some of the tools he helped create, the death of the homepage and the rise of the news feed, and what happens when your company goes from a fun idea to a potential cash cow. In the last 20 years, Rose has seen just about every corner of the tech industry, and he thinks there’s a case for Digg to make a comeback now — but only in a very different corporate form.
This interview has been edited for length and clarity.
How do you remember the internet from right before you started working on Digg?
There was some social activity showing up for the first time, where we saw people kind of coming together — Friendster was a big social network, and it was like, “Whoa, I can friend people and kind of see what they’re up to.” And that felt really different. We had email, obviously. We had walled gardens like AOL and all those other platforms that came before that were allowing us to chat. But not everyone was online, you know? It just wasn’t a thing.
So, I was playing around with Friendster, and then I remember seeing Delicious for social bookmarking. That was really interesting: people are actually bookmarking and saving things they want to revisit later. That was another signal. And then Flickr became a place to publicly share photos, and it was a really odd thing to say, “I’m going to expose some of my personal photos.” It felt weird because photos were always such a private thing. People were taking them on digital cameras and syncing their cameras to their computers and downloading the photos from their computers via, like, USB cables.
I just remember thinking, Okay, people are starting to connect in ways that I hadn’t seen before. They’re starting to share information that had previously been locked away. And then I was a big fan of Slashdot. Slashdot was tech news, and they were 100 percent user-submitted stories. They just had no way to rank them. It was an editor that chose which ones were on the front page, and they wouldn’t provide any visibility into what was being submitted. That’s so weird! You’re taking all these submissions, but you’re not showing everybody else all the cool stuff that’s being submitted? It seems like gatekeeping. Why not allow everyone to see that stuff and actually vote on it?
And then, this really weird thing happened where this technology started being supported by browsers, which was Asynchronous JavaScript — they call it Ajax — which allowed you to click on something and see the page refresh without having to go to another page.
That was what made Gmail feel so magical!
Yes, exactly. It was like it was the technology that unlocked so much of what we saw on Web 2.0, because someone could click on a voting button, and we could see the number go up without having to go to another page. In the first version of Digg, if you clicked to dig something, it would take you to another page that was like, “Thank you for your Digg.” Then, when we saw Ajax, I was like, “Oh, wow, this allows us to do inline voting. Let’s add it.” We got that working pretty quick. We made this really cool animated kind of fade-in and fade-out effect, and people were like, “Wow, I just like voted on something and saw the number go up.” It sounds so silly now, but it was a pretty big deal back then.
Digg was all tech news for, like, the first month, and I launched it because I thought, well, this would be an improved, more social version of Slashdot. And as being a geek, I kind of wanted to just figure out: Is there something here? Are there nuggets that the editors of Slashdot are overlooking that the masses would come together and vote on and bring to the surface? Then, we noticed that people were submitting stuff that was just like outside of the tech realm. And the people were just asking for more expansion of our items that we allowed people to submit. It was like, ‘Okay, well, let’s go broader here and just see what that surfaces.” And it just started working.
It was such a smash-up of things. But at the same time, no one had really done voting. There was no way to say, like, “I vote on a piece of content.” And for me, it was such a no-brainer. Like, of course we’re gonna vote on things on the internet later. This should exist. We did a handful of iterations on that stuff. And Daniel [Burka, a designer who eventually worked at Digg] picked a really cool color palette — he made it yellow. And we went back and forth on whether it should be an arrow or a thumb. He designed a little thumb, and I didn’t like the way some of the fingers looked, so we redesigned it. We went back and forth a few times there. And we eventually got to this idea of a thumb going up with a number next to it, which, again, I know it sounds simple, but we’ve never seen that before.
Do you ever wonder, if you had come up with something completely different — instead of a thumb, it was like an alligator pointing upward — if now there would just be upward pointing alligators all over the internet?
It was a very strange thing, where I think it was so universally known as, like, “I like this,” that it was easy for people to copy it, you know?
But the thing that was really interesting is that we started realizing, well, these votes — we can take them, and we can feed them back into our algorithm that we were developing and actually, hopefully, put together a customized news feed based on what you’re liking. And so that’s the stuff that we patented and actually ended up being the most valuable asset that we had. We sold Digg for, like, nothing — half a million dollars or something — that Betaworks bought and took it over. But the patents we sold for millions of dollars to LinkedIn. The patents were so valuable to LinkedIn because they were adding a lot of social elements. They wanted a defensive patent strategy against Facebook, and so they ended up buying the patents.
They’ve never been tested because I think that, obviously, Facebook knows that we have prior art on all that stuff, the like button and all that. Maybe a year and a half or two years later, Mark [Zuckerberg] came to my office and was talking to me a bunch about that because it was a brief period in time where we were larger than Facebook. He was asking me a lot of questions about, you know, digs and how they worked.
To be fair, though, I never wanted to get defensive about it. I thought of this is as something universal that all sites could apply — I didn’t invent voting, so it felt very odd for me to file a patent on something and try to block other sites from doing it. And so our legal folks had told us to get patents just because you’ll want to have them again, for just defensive purposes.
It seems you had to choose, relatively early on at Digg, “How do we decide what’s popular?” I think my assumption was always that whatever gets the most digs win — pure meritocracy. But then it sounds like pretty quickly you run into: okay, this system doesn’t work for a whole variety of reasons. It’s not what you want to be about, it’s a gameable system, on and on. And then you have to start thinking, “Okay, what are the other metrics of success that we care about?” I think you can track the whole course of the next 20 years by the metrics of success we decided to care about on the internet. I’m curious how you thought through that — what else you decided was important.
In Digg V1, I had an admin interface that had every single category listed out, and then it said the number of digs that had to hit in order for it to go on the homepage.
Like a hardcoded number for each one?
Yep, that was all it was. Just kind of thumb in the air — if a category was becoming more and more popular and more people were visiting it, then we would increase those numbers and bump them up every couple of weeks.
And then, to your point, once people started getting a lot of traffic, they started encouraging their own audiences to go and dig our stuff. And then we would see a few things. One, we see that they didn’t discover it organically because there was, like, no referrer. They’d directly to the permalink page, and they would dig from that page, and they hadn’t done anything else on the site. So, that was one signal. Or we saw one IP address would have like 50 digs from it, and so it would be like everyone in the office.
I remember one time, there was a CNET article, and it had like 100 and some odd digs to it. And it was sitting there sitting on the Upcoming section, but it hadn’t made the jump over to the homepage. Because if it all came from a single IP address, we would heavily discount the digs — “karma,” we called it behind the scenes. Karma was a combination of like… my god, it was, it was a nightmare. It was a nest of things. How new are the accounts? How many of them came from finding it naturally through an up-and-coming section versus going directly to the link itself? How many were unique IP addresses? There was just a bunch of stuff that went into it — how long they went and clicked out, and actually, did they click out and visit the article prior to digging it? You know, things like that.
So, there’s probably about 10 or 15 different weights that we had internally. And people were getting pissed. They would think Digg is a scam: “It’s at 115, and it’s not making the homepage!” And we couldn’t say, “Yeah, it’s because everyone at CNET dug this article, and we’re not going to let it get on the homepage.”
It was just a challenging time because then you’re fighting a PR battle, which is like, how do we prove that something is fair? I don’t care if this article makes the front page; I just want to make sure it’s truly wisdom of the crowds.
Honestly, I think that Reddit did the right thing where they deputize people to make those decisions along with an algorithm versus it just being our internal editors that were looking at stuff.
Is that process disillusioning at some point? You come into this because what you want is transparency, and you want everyone to be able to see and for it to be a true meritocracy. And then, oh, a true meritocracy actually just super doesn’t work.
I should have learned this lesson several times over now at this point in my career. But anytime there is a financial incentive, you’re gonna get bad participants, and they come out of the woodwork in the tens of thousands. So, you know, when Digg was doing 30-something million monthly uniques, we were banning thousands of accounts per day. We couldn’t even keep up with it. There was so much to be gained from getting your story on the front page of Digg. Once an international audience caught on where they could just hire and outsource people to just sit there and create fake accounts, it was an absolute nightmare.
The thing I remember about Digg is how much that front page was a thing. And I think part of the reason I wanted to talk to you in the first place is I think we’ve lost that idea — homepages don’t really exist anymore, and I miss that. But now I’m wondering if this push toward individualizing and personalizing the experience is just a response to trying to let the system work at scale, and it just doesn’t.
I think that’s right. But we did it the wrong way. It was really challenging because we had grown the team quite a bit, to 50-plus heads. And we had an immature ad platform and advertisers that didn’t know how to or whether they could trust advertising on Digg. And because Digg would get very toxic at times — you’d get a very heavily debated political article that hits the homepage — it felt like we really didn’t have control over the site. So, you would get advertisers that would say, “I don’t know, this content seems a little too dicey for me.”
We had this moment where our investors were like, “You need to clean up the site, and make it more profitable, because you’re gonna have a hard time raising future rounds of financing.” I think what Reddit did, in retrospect, that was quite smart was they kept the team relatively small and kind of let the market mature around them. I feel like we kind of grew the team to an incredible burn, and then we tried to go way too commercial and make it more of a cleaned-up experience. But in reality, the majority of people were coming there for the odd, weird stuff that they couldn’t find anywhere else.
Could you have said back in the day, “This super controversial, political stuff that everybody’s yelling at each other about, is just not what we do here. We’re going to boot this stuff off the platform”? Is that a choice you could have made? Is it just weights you should have made?
It was growing so fast, it was some of our hottest content! It was insane how engaged political users are. They are some of the most hardcore in terms of usage and commenting; they’re just addicted to this stuff. And so it was becoming more of our traffic. I think we should have given them their own area to play and said, “Hey, this is your arena. Go create and have fun.”
Is it possible to do the thing you were trying to do at actual scale? Or does everything eventually get too big to make sense as one cohesive thing?
I think you just hit hard caps on the size you can grow to. There’s only so many people that are gonna be interested in just a singular homepage of content, you know? I feel like we could have been the better version of Slashdot and continued to dominate and been a huge, massive tech source. Techmeme Plus Plus or whatever. I think we could have buckled down and said, “Digg is 10 employees or 15 or whatever, and we’re all about this. We’re not going to do X, Y, and Z. Let’s put some guardrails in place here and just be a great little niche site.”
It’s funny, now, because I actually really wanted it to be a tech news website. And it was the community and others that ended up joining the team that pushed and forced my hand — not forced it but really said, “We should go for something bigger here.” And then once you get investors involved, there’s a lot of people sitting around the table that want to see you have that billion-dollar-plus outcome.
And you push on that idea of bigger things long enough, and you eventually just end up with social networks, which, to some extent, seems like what happened, right? Did you have conversations about trying to go be a social network?
We were being crushed on that side, especially once Twitter started gaining momentum. I noticed pretty quickly that Twitter was breaking news stories faster than we were.
Their simple “What are you up to today?” box was so different from our flow. Our flow was like: give us a URL, give us a story. We didn’t allow text-based submissions — you had to have a URL associated with it.
And I’m not a fan of feature parity or copying other websites. I thought Twitter was doing Twitter just fine, you know? I didn’t want to just clone what they had done.
Kind of an unusual perspective these days.
Well, back then, it was actually frowned upon. When people would launch something new, if it was something where we were like, “Huh, I hadn’t thought about that,” we didn’t copy each other’s stuff. We were like, “Wow, they did a really good job, bravo to them.” I’m not going to take that feature. That’s something they came up with.
Nothing ever really came along to try and do Digg better than Digg or take that idea to the next level. If I wanted to go find something cool on the internet, in 2004-ish, I was sort of spoiled for choice. Since then, I’m just gonna go to one of my news feeds and hope there’s something there. That serves a purpose, but not the same one, and I’ve never really been able to figure out why that idea of the universal homepage just sort of went away.
We like to believe there’s this idea of a universal homepage. But in reality, if any company wants to go for scale, they just can’t rely upon this idea that 40 to 50 stories per day are gonna globally fit everyone’s tastes. And otherwise, you’re just capped at a hard number of users that like that particular angle of things.
Like, now, if you want to know about the best, weirdest programming shit, it’s Hacker News. If you want to just see globally what’s happening in tech, Techmeme’s the spot. Product Hunt probably still serves up-and-coming new things on the app side. So, there are certain ways that we get that information. But for me, because we have so many different varying interests, social networks just serve us so much better. I can be on a social network and get the craziest news around the Klotho protein and how it extends life and, at the same time, get wacky, crazy poodles jumping over plastic cups to the Zelda theme music — I have an account that does just that, which is amazing. I can get all of my personal uniqueness that is me, solved by just following a handful of accounts that represent me.
There’s a theory there, though, that says the whole “wisdom of the crowd” idea has just gone away. And now it’s been replaced by individual people but also this amalgamation of stuff I’ve signaled that I care about. And what matters is the system getting better at giving it back to me. But it means the idea of “the internet” being one thing has just died.
I think just the internet got too big. And also, honestly, I believe the wisdom of the crowds can produce really boring, non-sophisticated results. So, for me, it’s about personal curation of tastemakers and people that I trust, and that circle can expand or detract depending on the year or my interest over time.
But I feel you in that, sometimes, I wish I could just get a better zeitgeist of what’s going on globally that is outside of my bubble, right? Because the danger here is that we’re just being kind of spoon-fed the stuff that we already love. And so, how’s it introducing new perspectives and new ideas and, you know, turning me on to new information that I wouldn’t normally see, right? And I think that that is the downside of and the bummer to all of this, you know, is missing out on some of that.
How do you do that now? You’re a curious guy learning lots of new things — when you’re like, “What cool stuff is happening?” — where do you go?
I bounce around. I use Glimpse a lot; it’s a great way to see trends as they’re starting to pop off. I have a handful of newsletters I subscribe to that I consider high-quality.
It’s funny: there are two sides of my personality type. One is to play at the edges and break things and make sure I never lose that because that has served me well as an investor and allows me to hopefully see around corners early. And then there’s another part of me that, literally, I’ve spent the last two weeks just going deep on dumb phones and how we can disconnect from this technology.
I’m toying around with this idea of touching grass more, but yet figuring out the time and ways to play and have fun at the edges as well. I think most of us are leaning way too far in on being just always on our devices. And I’m getting really serious about trying to figure out what that balance is for me. I’d like for it to be the next chapter of what I work on, being really thoughtful about trying to encourage people to find balance, because I think we’ve gone way too far on the other side of having to say to ourselves, Am I missing something?
It’s kind of the end point of that 20-year cycle, right? We went to everything being endless all the time, and everyone is slowly realizing why that’s a problem. I hear more and more people all the time talking about dumb phones and talking about curation. And it’s why everybody loves email newsletters now. It turns the internet back into a thing that I do. And then I put it down. And we spent 20 years forgetting how to put it down.
As I think about the universal homepage thing, part of me thinks we need that more than ever now. Instead of having to go to 50 websites and 10 different forums and read 20 newsletters, how can I just get a quick sense of what people care about and what they’re saying… and then move on to my life?
I think you’re absolutely right. If you can find out who owns Digg, I would love to buy it back from them and turn it back into that old-school homepage. So, I don’t know if you have any connections…
I’ll look into it. But let’s just quickly reboot Digg right here, for 2024. What would you do?
I would heavily lean into AI on this front — AI for vetting and AI for a bunch of different things. If someone posts a comment, you could instantly run it against AI and say, “Is this comment additive to the article of substance, or is it attacking someone?” There could be some really interesting positive use cases for AI here to help with keeping things civil. I would lean pretty heavily on AI for both summaries for content moderation.
I would not want to embrace an ad model. I’d much rather have it be almost more Wikipedia-style, where it’s community-supported in some way. It wouldn’t be about building the next billion-dollar, publicly traded company, but more like a utility for good. I would want to really lean in heavily on this idea of providing a safe place for people. It’s unfortunate to me that I’ve had to step away from several different social networks out there because they just can be so toxic at times. And so I would want to spend a great deal of time thinking through those issues.
It would be important to go out and probably sit down with 50 or 100 of the largest moderators on Reddit and ask them what features and functionality they’re missing that they would like to see and have it really be community-driven features and functionality on the site versus top-down telling you what you should have. I don’t know. I think that’d be a good place to start.

For a couple of years, there was nothing on the internet so simultaneously thrilling and terrifying as having your website hit the front page of Digg. Thousands of people, maybe tens of thousands, would immediately come to your site — and there’s a good chance they’d crash it in the process. Hundreds of commenters would debate the merits of whatever you’d created or published, pick fights with you and each other about it, and make you feel like the internet’s main character. At least for a few minutes, until something bigger and newer and more controversial hit Digg.com and everyone moved on.

In its early days, Digg was something like the homepage of the internet. Any user could submit a link, and then any other user could either promote it with a “dig” or demote it with a “bury.” The best and most popular stuff made the homepage, which was seen by tens of millions of people a month. The most controversial stuff had epic comments sections.

So many of Digg’s features, from its voting mechanism to its commenting system to its occasional teeming toxicity, are omnipresent on the internet now. But in 2004, when Kevin Rose was working on the first versions of his new news platform — back when he was best known as a host on the TechTV network — it was all brand new. And what Rose and others built during that time has changed the way we all use the internet ever since.

I recently chatted with Rose, who is now a podcaster and investor, about why he built Digg the way he did and why he felt like giving users transparency and control was so important. We also talked about the legacy of some of the tools he helped create, the death of the homepage and the rise of the news feed, and what happens when your company goes from a fun idea to a potential cash cow. In the last 20 years, Rose has seen just about every corner of the tech industry, and he thinks there’s a case for Digg to make a comeback now — but only in a very different corporate form.

This interview has been edited for length and clarity.

How do you remember the internet from right before you started working on Digg?

There was some social activity showing up for the first time, where we saw people kind of coming together — Friendster was a big social network, and it was like, “Whoa, I can friend people and kind of see what they’re up to.” And that felt really different. We had email, obviously. We had walled gardens like AOL and all those other platforms that came before that were allowing us to chat. But not everyone was online, you know? It just wasn’t a thing.

So, I was playing around with Friendster, and then I remember seeing Delicious for social bookmarking. That was really interesting: people are actually bookmarking and saving things they want to revisit later. That was another signal. And then Flickr became a place to publicly share photos, and it was a really odd thing to say, “I’m going to expose some of my personal photos.” It felt weird because photos were always such a private thing. People were taking them on digital cameras and syncing their cameras to their computers and downloading the photos from their computers via, like, USB cables.

I just remember thinking, Okay, people are starting to connect in ways that I hadn’t seen before. They’re starting to share information that had previously been locked away. And then I was a big fan of Slashdot. Slashdot was tech news, and they were 100 percent user-submitted stories. They just had no way to rank them. It was an editor that chose which ones were on the front page, and they wouldn’t provide any visibility into what was being submitted. That’s so weird! You’re taking all these submissions, but you’re not showing everybody else all the cool stuff that’s being submitted? It seems like gatekeeping. Why not allow everyone to see that stuff and actually vote on it?

And then, this really weird thing happened where this technology started being supported by browsers, which was Asynchronous JavaScript — they call it Ajax — which allowed you to click on something and see the page refresh without having to go to another page.

That was what made Gmail feel so magical!

Yes, exactly. It was like it was the technology that unlocked so much of what we saw on Web 2.0, because someone could click on a voting button, and we could see the number go up without having to go to another page. In the first version of Digg, if you clicked to dig something, it would take you to another page that was like, “Thank you for your Digg.” Then, when we saw Ajax, I was like, “Oh, wow, this allows us to do inline voting. Let’s add it.” We got that working pretty quick. We made this really cool animated kind of fade-in and fade-out effect, and people were like, “Wow, I just like voted on something and saw the number go up.” It sounds so silly now, but it was a pretty big deal back then.

Digg was all tech news for, like, the first month, and I launched it because I thought, well, this would be an improved, more social version of Slashdot. And as being a geek, I kind of wanted to just figure out: Is there something here? Are there nuggets that the editors of Slashdot are overlooking that the masses would come together and vote on and bring to the surface? Then, we noticed that people were submitting stuff that was just like outside of the tech realm. And the people were just asking for more expansion of our items that we allowed people to submit. It was like, ‘Okay, well, let’s go broader here and just see what that surfaces.” And it just started working.

It was such a smash-up of things. But at the same time, no one had really done voting. There was no way to say, like, “I vote on a piece of content.” And for me, it was such a no-brainer. Like, of course we’re gonna vote on things on the internet later. This should exist. We did a handful of iterations on that stuff. And Daniel [Burka, a designer who eventually worked at Digg] picked a really cool color palette — he made it yellow. And we went back and forth on whether it should be an arrow or a thumb. He designed a little thumb, and I didn’t like the way some of the fingers looked, so we redesigned it. We went back and forth a few times there. And we eventually got to this idea of a thumb going up with a number next to it, which, again, I know it sounds simple, but we’ve never seen that before.

Do you ever wonder, if you had come up with something completely different — instead of a thumb, it was like an alligator pointing upward — if now there would just be upward pointing alligators all over the internet?

It was a very strange thing, where I think it was so universally known as, like, “I like this,” that it was easy for people to copy it, you know?

But the thing that was really interesting is that we started realizing, well, these votes — we can take them, and we can feed them back into our algorithm that we were developing and actually, hopefully, put together a customized news feed based on what you’re liking. And so that’s the stuff that we patented and actually ended up being the most valuable asset that we had. We sold Digg for, like, nothing — half a million dollars or something — that Betaworks bought and took it over. But the patents we sold for millions of dollars to LinkedIn. The patents were so valuable to LinkedIn because they were adding a lot of social elements. They wanted a defensive patent strategy against Facebook, and so they ended up buying the patents.

They’ve never been tested because I think that, obviously, Facebook knows that we have prior art on all that stuff, the like button and all that. Maybe a year and a half or two years later, Mark [Zuckerberg] came to my office and was talking to me a bunch about that because it was a brief period in time where we were larger than Facebook. He was asking me a lot of questions about, you know, digs and how they worked.

To be fair, though, I never wanted to get defensive about it. I thought of this is as something universal that all sites could apply — I didn’t invent voting, so it felt very odd for me to file a patent on something and try to block other sites from doing it. And so our legal folks had told us to get patents just because you’ll want to have them again, for just defensive purposes.

It seems you had to choose, relatively early on at Digg, “How do we decide what’s popular?” I think my assumption was always that whatever gets the most digs win — pure meritocracy. But then it sounds like pretty quickly you run into: okay, this system doesn’t work for a whole variety of reasons. It’s not what you want to be about, it’s a gameable system, on and on. And then you have to start thinking, “Okay, what are the other metrics of success that we care about?” I think you can track the whole course of the next 20 years by the metrics of success we decided to care about on the internet. I’m curious how you thought through that — what else you decided was important.

In Digg V1, I had an admin interface that had every single category listed out, and then it said the number of digs that had to hit in order for it to go on the homepage.

Like a hardcoded number for each one?

Yep, that was all it was. Just kind of thumb in the air — if a category was becoming more and more popular and more people were visiting it, then we would increase those numbers and bump them up every couple of weeks.

And then, to your point, once people started getting a lot of traffic, they started encouraging their own audiences to go and dig our stuff. And then we would see a few things. One, we see that they didn’t discover it organically because there was, like, no referrer. They’d directly to the permalink page, and they would dig from that page, and they hadn’t done anything else on the site. So, that was one signal. Or we saw one IP address would have like 50 digs from it, and so it would be like everyone in the office.

I remember one time, there was a CNET article, and it had like 100 and some odd digs to it. And it was sitting there sitting on the Upcoming section, but it hadn’t made the jump over to the homepage. Because if it all came from a single IP address, we would heavily discount the digs — “karma,” we called it behind the scenes. Karma was a combination of like… my god, it was, it was a nightmare. It was a nest of things. How new are the accounts? How many of them came from finding it naturally through an up-and-coming section versus going directly to the link itself? How many were unique IP addresses? There was just a bunch of stuff that went into it — how long they went and clicked out, and actually, did they click out and visit the article prior to digging it? You know, things like that.

So, there’s probably about 10 or 15 different weights that we had internally. And people were getting pissed. They would think Digg is a scam: “It’s at 115, and it’s not making the homepage!” And we couldn’t say, “Yeah, it’s because everyone at CNET dug this article, and we’re not going to let it get on the homepage.”

It was just a challenging time because then you’re fighting a PR battle, which is like, how do we prove that something is fair? I don’t care if this article makes the front page; I just want to make sure it’s truly wisdom of the crowds.

Honestly, I think that Reddit did the right thing where they deputize people to make those decisions along with an algorithm versus it just being our internal editors that were looking at stuff.

Is that process disillusioning at some point? You come into this because what you want is transparency, and you want everyone to be able to see and for it to be a true meritocracy. And then, oh, a true meritocracy actually just super doesn’t work.

I should have learned this lesson several times over now at this point in my career. But anytime there is a financial incentive, you’re gonna get bad participants, and they come out of the woodwork in the tens of thousands. So, you know, when Digg was doing 30-something million monthly uniques, we were banning thousands of accounts per day. We couldn’t even keep up with it. There was so much to be gained from getting your story on the front page of Digg. Once an international audience caught on where they could just hire and outsource people to just sit there and create fake accounts, it was an absolute nightmare.

The thing I remember about Digg is how much that front page was a thing. And I think part of the reason I wanted to talk to you in the first place is I think we’ve lost that idea — homepages don’t really exist anymore, and I miss that. But now I’m wondering if this push toward individualizing and personalizing the experience is just a response to trying to let the system work at scale, and it just doesn’t.

I think that’s right. But we did it the wrong way. It was really challenging because we had grown the team quite a bit, to 50-plus heads. And we had an immature ad platform and advertisers that didn’t know how to or whether they could trust advertising on Digg. And because Digg would get very toxic at times — you’d get a very heavily debated political article that hits the homepage — it felt like we really didn’t have control over the site. So, you would get advertisers that would say, “I don’t know, this content seems a little too dicey for me.”

We had this moment where our investors were like, “You need to clean up the site, and make it more profitable, because you’re gonna have a hard time raising future rounds of financing.” I think what Reddit did, in retrospect, that was quite smart was they kept the team relatively small and kind of let the market mature around them. I feel like we kind of grew the team to an incredible burn, and then we tried to go way too commercial and make it more of a cleaned-up experience. But in reality, the majority of people were coming there for the odd, weird stuff that they couldn’t find anywhere else.

Could you have said back in the day, “This super controversial, political stuff that everybody’s yelling at each other about, is just not what we do here. We’re going to boot this stuff off the platform”? Is that a choice you could have made? Is it just weights you should have made?

It was growing so fast, it was some of our hottest content! It was insane how engaged political users are. They are some of the most hardcore in terms of usage and commenting; they’re just addicted to this stuff. And so it was becoming more of our traffic. I think we should have given them their own area to play and said, “Hey, this is your arena. Go create and have fun.”

Is it possible to do the thing you were trying to do at actual scale? Or does everything eventually get too big to make sense as one cohesive thing?

I think you just hit hard caps on the size you can grow to. There’s only so many people that are gonna be interested in just a singular homepage of content, you know? I feel like we could have been the better version of Slashdot and continued to dominate and been a huge, massive tech source. Techmeme Plus Plus or whatever. I think we could have buckled down and said, “Digg is 10 employees or 15 or whatever, and we’re all about this. We’re not going to do X, Y, and Z. Let’s put some guardrails in place here and just be a great little niche site.”

It’s funny, now, because I actually really wanted it to be a tech news website. And it was the community and others that ended up joining the team that pushed and forced my hand — not forced it but really said, “We should go for something bigger here.” And then once you get investors involved, there’s a lot of people sitting around the table that want to see you have that billion-dollar-plus outcome.

And you push on that idea of bigger things long enough, and you eventually just end up with social networks, which, to some extent, seems like what happened, right? Did you have conversations about trying to go be a social network?

We were being crushed on that side, especially once Twitter started gaining momentum. I noticed pretty quickly that Twitter was breaking news stories faster than we were.

Their simple “What are you up to today?” box was so different from our flow. Our flow was like: give us a URL, give us a story. We didn’t allow text-based submissions — you had to have a URL associated with it.

And I’m not a fan of feature parity or copying other websites. I thought Twitter was doing Twitter just fine, you know? I didn’t want to just clone what they had done.

Kind of an unusual perspective these days.

Well, back then, it was actually frowned upon. When people would launch something new, if it was something where we were like, “Huh, I hadn’t thought about that,” we didn’t copy each other’s stuff. We were like, “Wow, they did a really good job, bravo to them.” I’m not going to take that feature. That’s something they came up with.

Nothing ever really came along to try and do Digg better than Digg or take that idea to the next level. If I wanted to go find something cool on the internet, in 2004-ish, I was sort of spoiled for choice. Since then, I’m just gonna go to one of my news feeds and hope there’s something there. That serves a purpose, but not the same one, and I’ve never really been able to figure out why that idea of the universal homepage just sort of went away.

We like to believe there’s this idea of a universal homepage. But in reality, if any company wants to go for scale, they just can’t rely upon this idea that 40 to 50 stories per day are gonna globally fit everyone’s tastes. And otherwise, you’re just capped at a hard number of users that like that particular angle of things.

Like, now, if you want to know about the best, weirdest programming shit, it’s Hacker News. If you want to just see globally what’s happening in tech, Techmeme’s the spot. Product Hunt probably still serves up-and-coming new things on the app side. So, there are certain ways that we get that information. But for me, because we have so many different varying interests, social networks just serve us so much better. I can be on a social network and get the craziest news around the Klotho protein and how it extends life and, at the same time, get wacky, crazy poodles jumping over plastic cups to the Zelda theme music — I have an account that does just that, which is amazing. I can get all of my personal uniqueness that is me, solved by just following a handful of accounts that represent me.

There’s a theory there, though, that says the whole “wisdom of the crowd” idea has just gone away. And now it’s been replaced by individual people but also this amalgamation of stuff I’ve signaled that I care about. And what matters is the system getting better at giving it back to me. But it means the idea of “the internet” being one thing has just died.

I think just the internet got too big. And also, honestly, I believe the wisdom of the crowds can produce really boring, non-sophisticated results. So, for me, it’s about personal curation of tastemakers and people that I trust, and that circle can expand or detract depending on the year or my interest over time.

But I feel you in that, sometimes, I wish I could just get a better zeitgeist of what’s going on globally that is outside of my bubble, right? Because the danger here is that we’re just being kind of spoon-fed the stuff that we already love. And so, how’s it introducing new perspectives and new ideas and, you know, turning me on to new information that I wouldn’t normally see, right? And I think that that is the downside of and the bummer to all of this, you know, is missing out on some of that.

How do you do that now? You’re a curious guy learning lots of new things — when you’re like, “What cool stuff is happening?” — where do you go?

I bounce around. I use Glimpse a lot; it’s a great way to see trends as they’re starting to pop off. I have a handful of newsletters I subscribe to that I consider high-quality.

It’s funny: there are two sides of my personality type. One is to play at the edges and break things and make sure I never lose that because that has served me well as an investor and allows me to hopefully see around corners early. And then there’s another part of me that, literally, I’ve spent the last two weeks just going deep on dumb phones and how we can disconnect from this technology.

I’m toying around with this idea of touching grass more, but yet figuring out the time and ways to play and have fun at the edges as well. I think most of us are leaning way too far in on being just always on our devices. And I’m getting really serious about trying to figure out what that balance is for me. I’d like for it to be the next chapter of what I work on, being really thoughtful about trying to encourage people to find balance, because I think we’ve gone way too far on the other side of having to say to ourselves, Am I missing something?

It’s kind of the end point of that 20-year cycle, right? We went to everything being endless all the time, and everyone is slowly realizing why that’s a problem. I hear more and more people all the time talking about dumb phones and talking about curation. And it’s why everybody loves email newsletters now. It turns the internet back into a thing that I do. And then I put it down. And we spent 20 years forgetting how to put it down.

As I think about the universal homepage thing, part of me thinks we need that more than ever now. Instead of having to go to 50 websites and 10 different forums and read 20 newsletters, how can I just get a quick sense of what people care about and what they’re saying… and then move on to my life?

I think you’re absolutely right. If you can find out who owns Digg, I would love to buy it back from them and turn it back into that old-school homepage. So, I don’t know if you have any connections…

I’ll look into it. But let’s just quickly reboot Digg right here, for 2024. What would you do?

I would heavily lean into AI on this front — AI for vetting and AI for a bunch of different things. If someone posts a comment, you could instantly run it against AI and say, “Is this comment additive to the article of substance, or is it attacking someone?” There could be some really interesting positive use cases for AI here to help with keeping things civil. I would lean pretty heavily on AI for both summaries for content moderation.

I would not want to embrace an ad model. I’d much rather have it be almost more Wikipedia-style, where it’s community-supported in some way. It wouldn’t be about building the next billion-dollar, publicly traded company, but more like a utility for good. I would want to really lean in heavily on this idea of providing a safe place for people. It’s unfortunate to me that I’ve had to step away from several different social networks out there because they just can be so toxic at times. And so I would want to spend a great deal of time thinking through those issues.

It would be important to go out and probably sit down with 50 or 100 of the largest moderators on Reddit and ask them what features and functionality they’re missing that they would like to see and have it really be community-driven features and functionality on the site versus top-down telling you what you should have. I don’t know. I think that’d be a good place to start.

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