The week of November 23, 2014

Me IRL: Dan Lyons

By Selena Larson

Dan Lyons doesn’t hate Silicon Valley—but there are some things he would do to change it. As a journalist and writer since the late 1980s, he’s seen the Valley transform from a silicon- and hardware-manufacturing hub to a gold rush of startups and brogrammers.

Lyons has worked as a marketing fellow at Cambridge-based software firm Hubspot, the editor-in-chief of ReadWrite, and a technology editor for Newsweek, but he’s perhaps best known as the writer who first satirized Silicon Valley with his popular blog, The Secret Diary of Steve Jobs.

As Fake Steve, Apple’s fearless leader, his commentary as an anonymous insider was both insightful and damning to the industry. You could consider it a proto–Silicon Valley, using humor to critique the industry’s various quirks, so it’s only fitting that he served as one of the writers on the upcoming season of the hit HBO show.

Now Lyons is stepping back into the fray as the new editor of Valleywag, the Gawker-owned watchdog site that skewers the tech sector with investigative pieces, snarky commentary, and a bit of inside baseball. The Kernel caught up with him not long after the announcement.

“The idea we’re all making the world a better place—it’s so idealistic. It might be better if they were honest and say, ‘We just want to be rich.’” —Dan Lyons

What are your plans for Valleywag?

I really missed being a journalist. I’m not sure what I’m going to cover because I don’t start until January, and who knows what’s happening in January. This summer I was working on the TV show with the other writers, and we were having so much fun making fun of all this stuff. And I had to go back to a startup, where they don’t laugh.

Valleywag is more about a point of view that people relate to. I’d like to have people coming in every day to see what’s there, rather than just coming in the side door through a Google search.

You want it to be controversial. Valleywag is supposed to be outspoken and irreverent, but you also have to be smart. It can’t just be cheap shots.

There’s a lot of room for investigative journalism in technology right now. Especially as some of these companies start collapsing financially, and as shit starts hitting the fan, there are going to be interesting stories to pry out of that.

People are going to get hurt. And people who get hurt are going to be willing to talk.

How long have you been covering Silicon Valley?

Since 1987.

What was your first gig?

I worked at a trade mag called PC Week. It was a magazine built around the IBM PC and the IBM-standard PCs like Compaq.

Finish this sentence: The Web would be better if…

I had much, much faster connectivity everywhere.

What’s the worst thing about Silicon Valley?

That smugness. The idea we’re all making the world a better place—it’s so idealistic. It might be better if they were honest and say, “We just want to be rich.”

What would you change?

There should be more diversity, and it should be less self-obsessed, less myopic. More being aware of the larger world.

Let’s talk about Fake Steve Jobs. What was the point of the blog?

It was very much an accident, a practical joke that got out of control. It wasn’t really thought through.

I was working at Forbes on the print side, and I was covering IBM and really boring datacenter kind of companies, and I wanted to learn about blogging. In those days, there were three blog platforms—Typepad, WordPress, and Blogger. I just started creating blogs on each platform, playing around to see how they were different. It was when all this talk about transparency started, and all CEOs should have a personal blog. I thought this was a really stupid idea.

I thought you probably don’t want your CEO just blogging, and what CEO even has time to blog? I thought it would be funny if you had this CEO and he was really obnoxious, really just a fucking asshole, gets drunk and gets high and blogs at night, and the PR people can’t control him.

So I had this idea—I had a Sergey Brin blog; I had one called Random VC that was just a Ken Doll–looking guy who was a venture capitalist. Then I created the Steve Jobs one, and people started reading it, and posting comments. I don’t know how they found it, because I sent the link to a couple friends of mine.

I didn’t cover Apple. I didn’t know much about Apple or Steve Jobs, but I just had this idea of a hippie-dippie poser California dude. I didn’t realize how rabid the Apple community is. That was what really made it take off. They started spreading the word. I did it for a few weeks and then I realized, “Oh shit, you can use this to cover news.” You could have Steve Jobs commenting on stuff that’s really happening. What if Steve Jobs was commenting on stuff in the news?

In 2006, Apple wasn’t as big or as in the news as frequently as they are now. They were an oddball company, before the iPhone. I happened to still be doing it when the iPhone came out—I caught this wave and took off.

How long did you write anonymously?

About a year and a half, and then the New York Times figured out it was me. He got this story that was like, “We’ve unmasked this guy.” There was a period of time where there were a bunch of anonymous blogs and everyone was trying to figure out who they were. I don’t think today it would even be newsworthy. I carried on for another year or so after I got outed. When Steve Jobs started looking really sick, I had a feeling it was pretty serious and I stopped.

When I started, I didn’t know much about him, but the more I got to know him I admired him. He’s a very complex figure, which made it really interesting to do satire. It wasn’t just all good or all bad. It was both. He’s a fascinating and complex person. He was a tyrant. Tyrants are always fun—fun to poke the big mean guy that everyone’s scared of.

Do people in Silicon Valley take themselves too seriously?

That’s why the Silicon Valley show on HBO caught on. They caught that aspect of it. The whole thing about “changing the world.” That satire of the Valley is a big reason it caught on.

They’re going to make 10 episodes next year, but I think there could be something that’s more persistent all the time. I miss doing Fake Steve. In some ways these companies really are changing the world, so it’s not all about this. But there’s a certain amount of sanctimony involved, and it’s so easy to make fun of that.

Are you currently working on Silicon Valley?

They hired six writers, and there’s four main people, the showrunner and Mike Judge, and coexecutive producers—it’s really their show. The six of us come in for 14 weeks and we just brainstorm and write and help block out plots and go to the whiteboard and figure out what’s going to happen.

Each of us writes one episode, and we get one credit. I have episode 8 of next season. It’s really the showrunner’s show; he writes a detailed outline for each episode. The episode I wrote, most of it is thought up by other people, but I get to go write it up and add stuff of my own. It’s a shared thing.

We all left in September and they start shooting in October. So they’re shooting now. The table read for my episode is this week—the 21st. I’m not going to go, because I’m in Boston. We’ll all go back and write the next season.

Do you think the show Silicon Valley amplifies or plays off the quirks of Silicon Valley that people hate or make fun of?

Yeah. I know the people working on the show, at least the writers, they don’t hate Silicon Valley. These guys are comedy guys—they look around for things to make comedy out of. They look at Silicon Valley and say, “That’s ripe for satire.”

But I think it’s a love-hate thing. People might be appalled by some things, but there’s also a huge fascination. I can’t tell you how many people have asked me, “Have you ever been to Google? What’s it like? I’ve heard the cafeterias are amazing.” It is a very cool world that most people don’t get to look behind the curtain on.

Part of it is just jealousy. There are huge amounts of money made there by these relatively young kids who you made a tiny app and are now billionaires. There’s this gold-rush mentality, which is appealing to some people and appalling to others. To me, it’s a little bit of both. On one hand, I’m like, “Shit, how can I get some of that?” And on the other hand, it’s like, “God, these guys are so pompous.”

“There are problems with racism, problems with ageism, sexism. You get these big companies full of dudes in their 20s who don’t deal with other people very well.”

In San Francisco, you have all these protester people that hate all the techies and throw rocks at the buses. They pretty much hate Silicon Valley, don’t they? In the sense that they’re smug pricks who make a lot of money and are ruining the neighborhoods.

In Boston, I have a lot of friends; some of them are kinda techies, but a lot are scientists, academics. In Silicon Valley, there’s a real myopia. They think the world revolves around them.

What do you think about brogrammers?

I have a hard time getting my arms around it. On the show, they had these characters at Hooli, but we kept hearing from people that those aren’t really brogrammers. Well, what is a brogrammer then?

To me what it means is it’s sort of these guys who aren’t the most well-adjusted guys and they live in a world where there aren’t very many women so they can be sexist. It’s not like a frat boy who played lacrosse in college. It’s not the same.

Yeah, they’re different. One thing you mentioned though is the sexism—many women can feel uncomfortable in that stereotypical brogrammer environment.

The stories that have come out in the last six months are shocking to me. One of the most shocking things I read was Heidi Roizen’s essay. I interviewed her back in the ’80s. She was one of the pioneers.

She said she didn’t want to speak publicly about it before now, but she told some of these anecdotes, and it’s like, this is what women have been dealing with all these years? I had no idea. I felt clueless.

There are problems with racism, problems with ageism, sexism. You get these big companies full of dudes in their 20s who don’t deal with other people very well. Having once been a dude in my 20s, I can imagine how horrible it would be.

You’ve written a lot about products and services that have a bit of a cult following. What’s it like being a critic of technology, and especially widely popular technology?

It’s not always fun. But you’re touching on something I find really interesting—why and how do people get personally invested so their identity is really tied up in some piece of technology? Whether it’s Linux, and they become rabidly “I love Linux, Linux is the greatest,” and there’s the other side, like, “Fuck you open-source assholes.”

There’s a psychological phenomenon there. It’s the same reason that people become rabid fans of football teams. They’re almost always guys. It’s the same thing with Linux and Apple communities. It’s a male psychological phenomenon, though there will be women in there.

I listen to them like, “You’re arguing about a football game like it actually matters.” I wish I knew something about psychology or anthropology to study this. There’s a sort of tribal mentality there, like being a Linux guy, and belonging to the Linux community.

Do you experience that?

Yes. The ones that attract the most hate are whenever I write about women in tech. I call out Apple every time they don’t have a woman on the keynote stage, which is always.

I used to do this thing at Fake Steve where I’d be like, “At Apple, we’re really proud of our diversity,” and then hyperlink the word diversity to the management page—20 middle-aged white men. All of them.

I was always super critical because Apple’s ads were always diverse—the iPod ads were diverse people dancing, but fuck you! You’re just a bunch of white guys in California. There always seemed to be a very strong, targeted dissonance between the image of Apple they presented to the world, and the reality.

Illustration by J. Longo