Interview With Valleywag Nick Douglas

Nick Douglas knows everyone — and he knows their secret quirks, too, thanks to the juicy tips readers send for his Silicon Valley gossip blog, Valleywag. So when faced with the disarming premise that we were recording a podcast, Nick opened up his vault, spilling the goods on Oracle's Larry Ellison, Google's Marissa Mayer, and all manner of California reporters, geeks, and venture capitalists.

We got Ze Frank, the future of the internets, and the egos behind the Gawker empire out of the way, and then Nick shared his secret party-crashing strategy (and Kevin Burton's secret dating strategy). He finished us off with some psychoanalysis of Cory Doctorow.

(Coincidentally, Mr. Douglas also talked about his desire, and failure, to get sued. We would have referred him to Michael Crook, but for legal reasons, we couldn't talk about the pending case then.)
To listen to the full interview in MP3 click here.

RU SIRIUS: So Valleywag is sort of thought of as the first gossip site for tech culture. Did any earlier sites inspire you?

NICK DOUGLAS: Well, before Valleywag I was working on a site called Blogebrity, kind of making fun of a lot of big time bloggers including Gawker. And that's the best way to get a job at Gawker. Continue making fun of them, start writing about the personal lives of some of the editors — and then they hire you up to make it safe.

RU: So I've got to find some really good dirt on Nick Denton? The nastiest stuff I can come up with?

ND: The current managing editor of Gawker got his start because he was writing about Gawker. I think there are at least three people who have been hired into the company just because they were writing about it so much. It's a brilliant hiring strategy, really.

RU: Does he have a nasty lifestyle that's easy to get underneath?

ND: Denton? Geez, I doubt it. He probably has some secret lifestyle that he pretends he wants no one to know. That's how Denton works and how all of Gawker works.

JEFF DIEHL: He cultivates it just for it to be discovered?

ND: Exactly, for it to be some day discovered. To the secret delight of everyone involved.

JD: Now, once you sign on with Gawker, do you have to sign some big long form that says you'll never criticize them again?

ND: Oh yeah. I'm not supposed to talk about his secret days in Turkey and what he does at the Turkish baths.

DESTINY: What form does that first contact take? Nick Denton comes to you and he says "Hey! I've been reading your blog, and you're talking about me!"

ND: Well, I first was IM-ing him, just bugging him, asking him for stories. And then he would... you'll notice there's some series of entries where I've "found" and "discovered" things about some of Denton's competitors on Blogebrity — and who knows who had tipped me off to those, but l just happened to be talking to Denton around that time! It's just a fun way to work — a wholly illegitimate way!

D: And then, at what point does he say, "Hey, I like your style, kid. Come work for me."

ND: That was over IM too. That was kind of weird, because he pulled me out of college. I have not graduated and don't really intend to, because I think it's more fun to have one affected failure in life instead of all the unintentional failures — to have one that I knew I was going to fail at.

RU: So if, implicitly, Nick Denton was giving you all these you must be getting all kinds of tips to slag other companies from various sources.

ND: Oh, yeah, totally. There's no one better for gossip than a competitor...That's the thing about Gawker bloggers. We don't really have to write anything. We steal people's jokes! Jessica Cohen, who writes the New York blog, Gawker, said a couple years back that readers love it when she steals one of their jokes when they submit something. They're like "Oh! It's my joke, and it's on a big site!" And she's honest about it. She tells everyone, "Yeah, I'm robbing all the readers' jokes." It's just a chance for everyone to write something. There's just got to be one person sitting in their underwear all day at a computer. That's really my role. I'm just the guy who sits there and lets everything filter in. It's like being a code monkey, but without the computer science degree.

RU: Any influence from ancient sites like Suck?

ND: Um, well, the embarrassing thing is I think I was in grade school when that was coming out. That's my biggest problem. I have to go back and read all the people who did this better back when there was more going on. I'm still reading stuff like "Fucked Company," the little book by Phillip Kaplan.

RU: Right. So you're catching up on ancient history?

ND: Yeah, looking at numbers and thinking "No way!" The YouTube sale for a billion-and-a-half dollars is nothing compared to some of the stuff that went on — and I didn't realize some of that going in. is one of the great ones to read from back then...I like seeing how many names came up about ten years ago and are coming up again. Like reading about John Battelle and saying, "Oh! He was hot shit in the 90s too. Really? And that didn't really pan out?! Oh!" So it's great to see that he's going again. It's quite inspirational, really. Like, if I screw up, this will happen again in ten years. This is great!

RU: We all get to be revenants! I've done it many times myself.

D: So do you have any predictions on what's going to happen in the future? Looking back on ten years, what do you see looking forward ten years.

ND: I tried making predictions a few months ago, and they're really good at not working out. So no, I have no idea. I'd love to see it get to a huge amount of money again, because I've got ideas, I've got lots of startups I would love to start. The sad state of affairs is that even now, I could probably walk out, go to three little gatherings of startups this week, pitch an idea, and get a million dollars. I'm pretty sure I could do that. And that's pathetic. That's awful. But it's awesome!

D: Aren't you tempted?

ND: Oh, I'm really tempted.

D: Why don't you do that?

ND: Because eventually, you know, they want more money back. And I have ideas; I just don't have ideas that are actually going to make ten million dollars out of the one million. I have ideas on spending the one million.

D: Well, there's a word for that. "Exit strategy."

RU: You need to be more ambitious in terms of wasting money. You need the late-90s level of ambition.

ND: That's true. I shouldn't think about wasting one million. I should think about wasting ten million.

RU: I mentioned in the introduction to the show that, way back when I was doing Mondo 2000 in the early 90s, we'd thought about doing a snarky sort of tech culture gossip column. And one of the things that entered into our conversation was the fact that people in that business are incredibly fucking thin-skinned. Much more so than rock stars or actresses and all that.

ND: Oh yeah. I agree.

RU: So what levels of outrage or prickliness have you run into?

ND: It's usually just really uncomfortable conversations at parties. I'm learning that it's a great art — defusing conversations. I never had that skill before. I was too passive-aggressive to actually have someone confront me at a party. But now I'm able to at least make someone like me for a half hour. And that's all I really need.

We haven't gotten a serious legal threat so far. Well, a couple of minor ones, but we're still waiting for a good solid cease-and-desist and a good lawsuit. We're really trying to get News Corp to sue us. They tried to stop the publication of some article [ed: originally intended for publication by someone else] calling MySpace a spam factory. And the author was revealing some of the background behind the company — that it wasn't really started by these two guys in their basement. And, since News Corp went to such lengths to stop the original publisher from publishing the article, we were hoping that if I actually published it on Valleywag, we could finally get sued. (Sighs) It didn't happen yet. I'm really disappointed about that.

D: So what's your next move? How are you going to bait someone into suing?

ND: Well, the problem is getting sued but also having enough of a case.

RU: You have to know it's one you can win

ND: Like I can't just run out and say, "Larry and Serge are gay lovers! We have photos!!!" And we don't, actually...

JD: Oh, we'll be taking that out of context.

RU: In terms of covering all this nastiness in the tech world, is there anybody that you've really come to despise?

ND: Despise? No. Have a sick obsession with? Yes. It's weird that all the Gawker blogs end up obsessing on someone. We almost make a selling point out of it. We make banner ads flashing out our obsessions. Defamer is unhealthily obsessed with Lindsay Lohan, Gawker is unhealthily obsessed with any number of magazines magnates. For me, Marissa Mayer, this VP from Google — I cannot get over how bizarre she is, and how bizarre the story she presents to the press is. She says things like, "I'll sit down and I'll do my email for about 14 hours in one spell!" Who does that?

RU: Has anybody seen her in person?

ND: I've seen her. She ran away from me at a party. I tried to say hi. I was nervous as hell. We keep running articles on Valleywag... "This is not a real person. She has to be a cyborg. We're pretty sure, she's either a cyborg, or a Cylon from Battlestar Galactica. I'm pretty sure that she's number six."

I think I actually show up in the first 10 search results for Marissa Mayer. And so that's great. I can say, "Oh, I can fuck with you, from your Google results!" It seems like a nasty thing to do to someone...

D: I'm in your house, printing your gossip.

ND: Exactly. But since I'm not condemning her — I don't really condemn Marissa, I'm just fascinated with the bizarre lies she's telling to the press.

RU:Well, other than the fact that she emails 14 hours a day, what else is odd about her?

ND: She claims she holds about 70 meetings a week, which I think boils down to — what, 14 meetings a day?

RU: For a total change of subject, tell our audience who Kevin Burton is, and what he wants. What does he wish for?

ND: Oh, gosh. See, now this came up last week, when I was on vacation. But Rick Abruzzo, who edited Valleywag that week, found some Craig's List ad that seems to be by this local entrepreneur, Kevin Burton. And he was looking for someone with dark hair who likes anime and Zen...

RU: Hey! I have dark hair and I like anime and Zen!

ND: Exactly! It basically looked like someone very awkwardly trying to say they wanted an Asian, but in such a stereotyped way that he would never succeed at his goal. He would only get 13-year-old goth girls who really had a thing for Yu-Gi-Oh. But we found the ad and connected it to him. He, of course, denied it. And then we ran the item, and then he admitted it was him. Then he wrote me an IM saying, "Can you not write about my personal life any more, it's kind of creepy?" And I said, "Yes! Yes, it's kind of creepy. That's why I ran it." That's exactly what was fascinating about it. But the thing is; Kevin has done things like this before. He was in Wired talking about one of his previous dating strategies which is going to a wireless cafe...

JD: Wait, I'm getting my notepad out.

ND: ...opening up something, Etherial, and sniffing the IM traffic of other women in the cafe. And he will find their IM name and IM them. And somehow, he claims, they find this impressive. "Oh! You stalked me! In a cafe!"

RU: So has anybody accused you guys of entering Jason Fortuny territory with this?

ND: Well, the thing was, we just originally posted that this looks like it's Kevin Burton. And then someone else tipped us and said, "Look. This screen name happens to be here." He put up his screen name. We did not post anything that he hadn't put out there openly on Craig's List. This wasn't some private email he had sent or anything.

JD: Jason Fortuny would say the same thing.

ND: But we didn't condemn. We never condemned. You know? If Burton had been doing something really illegal or something, that would've been more of a personal thing. I would've probably approached Kevin. I know him personally, you know? But it was nothing like the Fortuny thing. It was just some guy doing a weird Craig's List ad. It was fun.

D: So is there anything you won't print? Anything where you'd say, "Oh, this is too sensitive, I can't touch this."

ND: Well, there's stuff that's sensitive enough where I'd have to get actual confirmation. If someone accuses someone of doing a crime, usually I try to check that. If something that's libelous gets out, it's usually just me not thinking, "Wait a second! I'm accusing someone of fraud! I probably should check that before I publish!"

RU: But this is something that you can do here, on our show. So go ahead!

ND: Right. Brilliant! Well, usually there's not that much. I guess I'm just not a good enough investigative journalist yet. I haven't found stuff that's too good to print.

D: Would you like to?

ND: I would! I'm actually looking at something. It's kind of been known that Eric Schmidt is married and also goes on certain vacations with this other girlfriend. It's been in the news. He's been spotted with her. The real question is: is he actually planning on getting divorced and has he told his girlfriend that he's getting divorced? There's this great thing about following some of these techies. It's not like following Lindsay Lohan. Everyone knows Lindsay Lohan is trashy, and you just get to have the glee of pointing out how trashy she is. The thing about the guys from Google is they want to be dorky, they want to be sweet, they want to have really innocent photos everywhere, and here's Eric Schmidt taking his girlfriend out on vacation while his wife is somewhere else. These guys really are just like anyone else, and that's what's really fun to show.

Larry Page, one of the co-founders of Google, when he's onstage somewhere, he always appears in this lab coat, and he acts really nerdy and he's not a good speaker. But at this one party that I kind of snuck into, he was there looking so L.A. and looking so slick. I was like, "Oh my god, you've really fooled everyone, haven't you!" That's great!

RU: Speaking of rumors, Dave Winer is spreading a rumor that you're leaving Valleywag (I have the quote)... "To do a web video show with one of the big video producers." So what about this gossip about you?

ND: First off, I'm surprised that — if Winer is still blogging — that anyone reads him.

JD: Ouch!

ND: Secondly, I'm surprised that people believe him. (A lot of people were IM-ing me about it.) But Rocketboom is hiring, and so there are always rumors about that. I'm working on a project...

RU: Now you guys are going hammer and tongs after Rocketboom on the site, on their figures. Talk about Rocketboom and their figures.

ND: Well, actually, this has more to do with the vlogger, Ze Frank. Usually, in any argument, I'd always take his side. Great guy. Never met him in person, but I just love his work. Huge fan. But lately, he's started going off on this campaign against Rocketboom because he noticed they had a lower Alexa score. He kind of has a point. They're inflating their numbers a little. Rocketboom is not the most popular show out there. It's just a lot of people know about it because they're so good at promoting themselves. And they pretend they're the Moses of some new culture that's going to totally shatter everything.

That's why Ze Frank makes fun of them. Rocketboom thinks that just because they have a daily news show, this means it's the end of CNN. The end of old, dirty, nasty, wretched media. Andrew Baron can't pile on enough pejoratives about what he's overthrowing.

RU: But they don't really believe that either. That's hype...

ND: They're another show. They're another show with a pretty girl that covers news. They're kinda good, but revolutionary? I don't know what's really different there. They could get picked up on TV and they'd be another little slot on TV.

RU: I would put them somewhere below the Daily Show in terms of their entertainment value.

ND: Oh, hell yeah.

D: Their real claim is that they're hugely popular. "Whether we're good or bad, we're hugely popular! We've got 300,000 visits."

ND: Right. They got 300,000 downloads started. Ze's argument is, how many of those people watch it the whole way through, and how many people give up after 30 seconds and say, I'm gonna go watch Ze Frank instead!

People are just running into the problem that you're never really going to be able to tell exactly how many people are watching your show. Unless you have an ad at the end. That's what Ze has. He's hosting with Revver and he can say this is how many ads were shown. Which is pretty damn great, because that's what you really need your numbers for.

So right now, Rocketboom can just inflate their numbers and Ze is trying to fight it. But at the same time, I don't think anyone wants to hear that from Ze. Mostly we want the monkey to dance. And maybe he has a good cause. He's funnier than Rocketboom. He's much better than Rocketboom. I don't watch Rocketboom, I watch Ze every day. But do I really want to read an essay by him, about Rocketboom?

D: So what do you think of the whole video-blogging space? Do you think that's the next big thing?

ND: It's a next big thing. It's not like text blogging's just going to disappear. "Oh, there's video! Can't write any more!" Or, "We can't podcast! Damn!"

D: "Curse you, video bloggers!"

ND: Right! It's just another cool new thing. But yeah, it's going to get much bigger than it is now, just because more people need to switch over to new broadband connections, and more people just need to get used to the idea of watching a lot of video. It's this gradual thing. As people get used to it, and it becomes a not-nerdy thing to do.

RU: You emailed me that you do have some project ideas. Why don't you talk a little bit about those.

ND: There's one project I've been working on that... there's a sort of video news thing that I'd love to do, because right now we get stuff like Rocketboom. And we get stuff that kind of tries to do video news every now and then. It turns into talking about other video bloggers. That's not going to fly, long-term. I think there's not really a show out there yet for your average person who goes to Yahoo as their home page; they get their news from Yahoo; they do their email from Yahoo... The typical example is your mom, right? Or like the average guy on the street. There isn't a show online he watches all the time. He probably watches some YouTube clips of The Daily Show. So there really needs to be one show that comes out that is like The Daily Show for the internet. I think if one show came out that was half as witty, and probably shorter — that would be good. It has to be short because it's like watching porn. I think Slate said that it was like watching porn. It's not the same as watching TV. You're really only interested for quick blips. So if I did anything in video, it would probably be something short like that.

RU: So therefore actual sex is like watching TV.

ND: I think Baudrillard just spittled in his grave.

RU: You promised in your email to psychoanalyze Cory Doctorow.

ND: Okay, right. In all his science fiction, he seems to have this one thing going on. In all his stories, he has this male lead, And almost all the time, the character has some sort of cocoon-like space that he goes to. In this one short story that's a continuation of "Down and Out..." this kid goes to some re-charge station. And it seems like it's like those egg-shaped chairs in Men in Black. So he's in this sort of cocoon-like space, and one day he finds this female friend of his in that space. And in another story, this kid grows up in a cave. What's the one where the kid is the son of a mountain and a washing machine? I forget which book it is, but this kid brings his girlfriend to this cave where he grew up. And so that's his home. I have more examples, but I forget them all. But there's this pattern of females intruding in some male cocoon womb-like space. And the English major in me just can't get that out of my mind, or stop thinking, "Cory, is there something, something going on there? Something you want to share with the rest of the class?" Which is probably not the first thing I want to say to him, I hope this isn't the first thing he ever hears from me, is me psycho-analyzing him.

RU: Well, there's a fairly good chance he will read this, actually

ND: Damn. Great. [General laughter] Hopefully he's open to it. He's going to have some asshole 22-year-old blogger in his next story.

D: In a cocoon-like space, all alone....

ND: Trapped somewhere, for the rest of time. That'd be kind of flattering.

He also has his female characters — who are almost always the love interest for the main male character — and they always abandon or betray the main male character with the secondary male lead.

RU: Yeah. That came up when I interviewed him, actually. I noticed that theme.

ND: Really? What did he say about it?

RU: Well, he went into a discussion about the importance of trust and betrayal as a theme within the context of digital culture, and so forth.

So before we let you go, I want to bring it all back around to gossip. Is there a particular sector within tech where the weirdest behavior is observed?

ND: It seems like the weirdest behavior will always happen in the dotcoms, because that's where you get the people who don't necessarily know a thing about tech. It's kind of a random mix. You've got these start-uppers who aren't really sure how to handle all this money, the young kids who aren't really sure whether it's smarter to play the punk rock kid or the really humble kid. And the journalists don't know quite how to handle it, and they all get starry-eyed. It's fun, actually.

See also:
Sorry 'Bout That, Nick
Where in the World is Nick Douglas?

One thought to “Interview With Valleywag Nick Douglas”

  1. I really liked TMZs coverage of Lindsay Lohan in court yesterday. She was having a complete meltdown!

    I almost felt sad for her.

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