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Kevin Rose
Partner at True Ventures, True Ventures

Anthony 'Pomp' Pompliano and Kevin Rose On Stacks (STX) Future

📅 Feb 21, 2025 Founder School 28 MIN 260 VIEWS 22 SEGMENTS · 2 SPEAKERS
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Questions asked in this interview

8
  1. 0:42Maybe just like, how do you describe where you grew up and how you got into the technology industry?
  2. 3:43How does that feel today or even back then?
  3. 6:08How have you seen some of the decisions that you guys made early on evolve into today's world and just how do you think about content moderation on the internet today?
  4. 9:35Like how do you just think about the evolution of that?
  5. 13:52And both from a moderation standpoint is it different, but also there seems to be more sensitivity and much more anger around I'm being silenced versus I can't take an action on a site, right?
  6. 16:03Like how do you think about almost the magnitude of the person and the weight of the words and how that plays into some of these decisions?
  7. 19:12Or is this just, hey, we're human and we're having short-term kind of overreaction and like the truth is somewhere in between, we have like coexistence between centralized and decentralized systems moving forward?
  8. 26:47Where can we send people to find you on the internet and find out more about your work at True?
Interviewer 0:05 ↗
All right guys, bang bang. I've got a very special guest, probably one of the earliest internet entrepreneurs, Kevin Rose, is with us. We are recording this as part of the Stacks conference, which is H Block Stacks virtual event. And so there's been a ton of great speakers and lots of great information, so highly recommend you go and check out the rest of them. But Kevin, thank you so much for taking the time to do this.
Kevin Rose 0:30 ↗
Dude, I'm so glad to be here. I know we've traded emails over the last like six months or so, or three months, whatever it is, and couldn't find a time. And it's awesome, as a listener of your show, it's cool to actually be on. So thanks for having me.
Interviewer 0:42 ↗
So I have to say that there was a moment where all of a sudden my phone started blowing up middle of last year. And I started looking and everyone was like, Tim Ferriss and Kevin are talking about the Chamath episode. And I was like, wait, what is going on? And so I went and I listened to the episode and I guess you had listened to Chamath Palihapitiya in like the heart of the pandemic and the economic crisis pretty much just say what he meant and he really kind of went off. And so it was cool to kind of hear your thoughts about one of the episodes. But maybe let's start with your background. You know, you've worked on so many important pieces of what I kind of consider the internet economy. Maybe just like, how do you describe where you grew up and how you got into the technology industry?
Kevin Rose 1:32 ↗
Yeah, well, of all places, I grew up in Las Vegas, Nevada. I moved out there, my dad was in finance. He worked for a company called Principal Financial Group and like they had a good paying job and it was like a chance for us to like have a little bit more money. We were like standard kind of middle class family. And so he moved out there, that put me in the middle of all things Las Vegas. Did not really enjoy that, but I got into tech and computers out there and desperately wanted to figure out a way to get to the Bay Area because I just had been reading about how everything was going on, you know, especially in '99, 2000. And so I said, well, I got to get to SF. Figured out a way to get kind of a low-level job working in San Francisco, moved out there, fell in love with the city. Eventually took me a little while to love that city. And then yeah, started my own thing in 2004 when the kind of Web 2.0 was just getting started. And I launched the first social news website called Digg. And so that happened in late 2004 and kind of to my surprise, just people like to vote on articles and tell you which ones are the best and have a say. And that all this stuff was relatively new because there really wasn't a way to do this stuff in a real-time fashion. That type of technology was just coming online. So like a great example is, you know, if you were to dig something back then, or eventually later, you know, about a year later when Facebook added likes, or you upload something on Reddit, people used to forget it would actually have to take you to another page. Like when we first launched Digg, you would have to say like dig something, it would take you to another page and say thank you for your dig because there was no way to do it in line. And so when they came out with asynchronous JavaScript to make that happen, you could actually click something and see the page refresh with the number. And as silly as that sounds today, that was like bleeding edge back then. And so that's kind of some of those early kind of new versions of ways to manipulate JavaScript was what led us to creating some of this real-time voting. And it was right place, right time, lots of luck, and it just took off from there.
Interviewer 3:43 ↗
How did it feel to have built something that really became part of people's habits on the internet? Right, kind of the early users of Digg ended up, a lot of them, going to be very successful technology entrepreneurs as well. But just, I'm sure people would tell you all the time like, oh, I use Digg every day, or literally, you know, I remember using Digg so much. How does that feel today or even back then?
Kevin Rose 4:09 ↗
You know, it's, I think that anytime you can have a small little impact on the internet and change just a little tiny piece of it, it's a beautiful thing. And I would say the biggest one was probably when Drew, the founder of Dropbox, came up to me and was like, we launched on Digg and that's what really blew us up on that first day. And he's just like thanked me for that. And I'm like, wow, you created a Dropbox, like thank you, like that's awesome. So it was a cool, it was such a small community back then though. Like when Web 2.0 happened, it wasn't like, you know, in today with all the money in the valley and all the startups and, you know, there being thousands and thousands of different startups kind of all competing for the same eyeballs and just a flood of money. Back then it was a handful of folks. So like knew the Twitter folks and, you know, Zuckerberg was really curious about Digg's before he added likes. So he came over to my office and like just sat on the floor with his slippers and like talked about like how it worked. And like there was like all those early days, but no one was thinking it would be this big. It was like, it was just like, well, how can we make our websites better? Like there was still no mobile, like how can we just make our websites better? What features can we add to attract more users? So to watch and see how, you know, Twitter and Facebook and some of the other bigger platforms, Reddit and others, have changed the world, this just, it's so cool. It was a great time and lots of mistakes made. I was in my early 20s, definitely had no idea how to manage people, no idea how to properly hire or fire or prune or any of the things that a good founder and CEO should do. It just, we, it was, I was just so immature. So, you know, I look back on those days and just see a lot of mistakes, but really it's just lessons learned. You know, it's just, I used to beat myself up about them, now I just consider them, you know, really valuable lessons that I wouldn't make today and ones that I had to go through.
Interviewer 6:08 ↗
Yeah, and obviously being a little bit older, having more experience helps in the hindsight. Talk a little bit about the evolution of content moderation, you know, as you built that kind of first site and you had to break a lot of ground and kind of figure things out. I don't know how many really, you know, examples you could pull from, you know, even Zuck had you to go and talk about likes and digs and all of that. How have you seen some of the decisions that you guys made early on evolve into today's world and just how do you think about content moderation on the internet today?
Kevin Rose 6:40 ↗
Yeah, it's funny, I was talking to a friend of mine who was kind of our head of content moderation at Digg and he's now been at Reddit for seven or eight years, something like that now, and does a bunch of moderation over there. And just seeing and hearing about the better, just the technology that they have on the machine learning side and the things that they're doing to identify spam early on that we didn't have back then. But you know, I look at what's happening on Twitter with the issues that they've had around moderation and I really feel, when you've been behind the scenes and you see what happens, you realize just how crazy it is. And the general public typically doesn't see this type of thing. And so like for example, and I'm sure Reddit has to deal a lot with this, is like when you want something on the front page of Reddit and you want to get it because, you know, there's millions of eyeballs there, right? If you can get a story on the front page of Reddit, that's worth a lot of money, right? So spammers are going to go and try every single angle of attack to try and get something on that front page. And oftentimes what happens is they'll go and attack something and then claim foul play and say you are, you know, suppressing the story, this is false moderation. And from just a standard consumer on the site, you're like, yeah, this thing had thousands of votes, why is it not on the front page? But what you don't see is behind the scenes, 80% of those votes came in a not a natural way, but a way that they've determined to be fraudulent. So that can be people going directly to the permalink site without actually naturally discovering it through the kind of upcoming section or any other page. It could be a bunch of new accounts all voting on the same thing. It could be a bunch of accounts from the same IP address. It can be a bunch of accounts all or votes all happening within a very short time window. There's just like a thousand different things to look at. And from a just a consumer looking at the total number of votes, you would say, well, something is wrong, like Reddit suppressing this or Digg is suppressing this or whoever it may be. But in reality, there's just a whole mess that you have to, and you can't come out and say and call them out, right, publicly. That's just not a thing you do. So it just turns into, you know, scandal or quote unquote deep state trying to keep us down or whatever it may be behind the scenes. And in reality, there's a bunch of shady stuff going on. And so when I see that happening at Twitter and other places, and just, you know, when we added like, you know, messaging or the ability to communicate behind the scenes and you see people all getting together in big groups like trying to all zero in on an article to try and promote and hack it, it makes me feel very fortunate that I'm no longer in that game because it's messy. It is really messy.
Interviewer 9:35 ↗
It also feels like there's this constant healthy tension, right? If you're that person who wants traffic, you want to do everything you can to increase the probability of getting traffic, getting, you know, better placement, getting kind of up in the rankings on the various sites. But at the same time, people don't want you to do that who run the site. And so, you know, there's always the trick of like, I love when a startup will email me, say, you know, Product Hunt, hey, don't click on this link, but go to the Product Hunt website, you know, scroll down, we're ranked about, you know, 30th right now, you'll find us on there and then upvote us. And so it's funny to kind of see the constant cat and mouse game, I think. But what that does lead to though is you've mentioned a couple times like almost malicious actors, right, or kind of bad actors. And so how did you guys previously deal with this at Digg or maybe some of the other companies you've invested in? And then now we're seeing more of what I'll call just like deplatforming or kind of completely taking people offline. Is that not really a new thing and that's been going on for a long time, it just maybe people didn't talk about it as much, didn't have as much tension? Or is it something that maybe is a more aggressive response to kind of the ratcheting up of activity from users? Like how do you just think about the evolution of that?
Kevin Rose 10:50 ↗
Yeah, it's tough because you have to put users, like there's not one universal policy that just apply and work well to everyone. So there's different intentions behind each of these different types of, you know, quote unquote fraud or manipulation of the system. And so sometimes we had, like to your point, like there are people that come in that have great articles that just want to get more exposure. And so they tell their friends, go try and find this organically and vote it up and blah blah blah. And that there's not really a lot of harm in that. There's confusion in that. Like I remember one time when CNET, they had probably 75 of their employees go and sign up for Digg accounts and all dig the same article. And they were pissed that it didn't make the front page. And I'm looking at the data and it's all like CNET email addresses and it was all employees and they'd all created accounts within the last 20 minutes. And I'm like, you guys don't understand, like there's a whole karma system that you can't see behind the scenes that is attributed to each one of these accounts. We know these are new accounts and we're not going to give them the same weight as we say someone that's been on the site for three years. So they just couldn't understand why their content wasn't making the homepage. And so it's frustrating for those people, especially when they believe they're trying to do something good. In this case, it wasn't a bad act, it was like a legitimate article, they were just trying to give it a little extra love. Now there's the other side of things where, you know, you have a spammer, you know, you have someone that is really trying to promote paid content or content that is just like, you know, the typical spam that you would see in your inbox, you know, stuff like that. So we would do all different types of things, including we had a system where you could set a flag on someone's account or a series of accounts or hundreds of accounts and tell them that they were called like silent accounts. And what that meant is they could come and dig all day long and they would actually see the numbers go up, but if they logged out or anyone else looked at them, the numbers would never go up. So they actually were just spinning their wheels. They thought they were like actually positively voting on something. And so this was great because the second you ban a spammer, they see that they've been banned and they go and create another dozen or five dozen or whatever new accounts. And so this just kept them believing that they were doing something when in reality they weren't. So there's just so many different tactics. And then of course the kind of like actual physical banning of people. Like we did that by the, you know, we probably, I don't know how many we had by the time that I left Digg, but it was in the hundreds of thousands if not over a million accounts banned. You know, it's just there are certain times where people are so malicious that you just can't, they can no longer be active on your platform and you have to do everything you can. Like I mean, hate speech, things that, threats. Like I had to have, when I was doing a live podcast one time, 24 hours before we were going to go live, we had a bunch of emails that were sent to saying that someone was going to bring a gun and shoot me and kill me at the live podcast. And so we had to hire personal security to come out and like frisk everyone, check their bags when they came in for the live show. And we talked to the FBI back then and it was just, you know, it's stuff like that where you got to be careful.
Interviewer 13:52 ↗
Yeah, and it feels like there's a difference between if I am maliciously like trying to vote things up and almost not creating content but more so trying to manipulate it, that's very different than if I'm the one who's actually creating the content, I'm saying things that are malicious, hurtful, you know, kind of violent, whatever. And both from a moderation standpoint is it different, but also there seems to be more sensitivity and much more anger around I'm being silenced versus I can't take an action on a site, right? Like to me, the silencing component seems to be where all of the focus goes. But really what you're saying is, hey, for, you know, two decades there's been all sorts of things that these platforms have been doing, not necessarily in a bad way, like they're trying to make the experience and the product as good as possible for the people who are there for the right reasons.

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APA, MLA, BibTeX
APA

Rose, K. (2025, February 21). Anthony 'Pomp' Pompliano and Kevin Rose On Stacks (STX) Future [Interview transcript]. Founder School. CEOInterviews.AI. https://ceointerviews.ai/interview/777249/

MLA

Kevin Rose. "Anthony 'Pomp' Pompliano and Kevin Rose On Stacks (STX) Future." Founder School, 21 Feb. 2025. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/777249/.

BibTeX
@misc{rose2025_777249,
  author       = {Kevin Rose},
  title        = {Anthony 'Pomp' Pompliano and Kevin Rose On Stacks (STX) Future},
  howpublished = {Interview transcript, Founder School. CEOInterviews.AI},
  year         = {2025},
  month        = {feb},
  url          = {https://ceointerviews.ai/interview/777249/},
  note         = {Speaker-attributed transcript with timestamps}
}