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So What Do You Do, Sarah Lacy, Author, Once You're Lucky, Twice You're Good?

In her new book, a tech reporter explores how Web 2.0 startups have revitalized Silicon Valley.

By Greg Lindsay - June 18, 2008
Sarah Lacy's new book Once You're Lucky, Twice You're Good: The Rebirth of Silicon Valley and the Rise of Web 2.0 tells the story of what happened after the dot com eraís implosion at the beginning of the decade. She spent a year trawling startups you might have heard of -- Facebook, YouTube, Twitter, Yelp, Slide, Digg, Six Apart -- and crawling inside the heads of their founders, many of whom had escaped the crash unscathed or even come out ahead, but were desperate to prove their success hadn't been a fluke (or worse, a con). Lacy has spent nearly a decade in Silicon Valley as a reporter, first at the Silicon Valley Business Journal and later at BusinessWeek, where she's retired from the grind of beat reporting but continues to write her biweekly column "Valley Girl." She's since branched out into video as the co-host of Yahoo Finance's Tech Ticker and as a blogger herself. And she continues to climb on stage as a moderator and host even after her infamous fireside chat with Facebook founder Mark Zuckerberg at this spring's South By Southwest conference.
Name: Sarah Lacy
Position: columnist, BusinessWeek; co-host, Yahoo's Tech-Ticker; blogger; author OYLTYG
Resume: Memphis Business Journal, San Jose/Silicon Valley Business Journal, BusinessWeek, all as staff reporters covering finance/tech. Now self employed and contracting
Birthdate: 12-29-1975
Hometown: Memphis, Tenn.
Education: Rhodes College, B.A. Literature
Marital status: Married to photographer/designer Geoffrey Ellis
First section of the Sunday Times: "Ha ha ha New York question! It sits in a bag on my front step. I'll check out business stories online though."
Favorite television show: "I love TV and it changes all the time. Re-discovering Gilmore Girls on the days I work from home. It makes for a nice lunch break."
Guilty pleasure: "Books by Stephanie Meyer. Yes, even the teen ones."
Last book read: The Road
What's it like to attempt (and unlike some, actually finish) a book that tells the story of Silicon Valley? Is yours a sequel of sorts to the ones that came before? And what are the themes shared by your book and the Silicon Valley canon?

A lot of the books that have been written about Silicon Valley are really good. Michael Malone's books are incredible. I think his Infinite Loop is the best book that's been written about Apple. I read it nine years ago, and it really made me want to write my own. You know, these are stories that are so iconic -- American Dream stories. The people who are building these companies are, for all of their flaws, so likeable because they didn't come from money, and they're trying to build something greater than themselves. The complaint is always that these stories are rose-y, but that's because ultimately these stories are so tied into our core values as a society. So you can hate them for a lot of personal reasons, but people really want to believe these guys were flukes. But if you reason how hard these guys worked, you can't help but respect them. And that's hard for me, because it's easier to write about a total fluke.

Is it really accurate to portray these companies as psychological extensions of their founders? Journalists have always made Steve Jobs and Bill Gates act as stand-ins for their companies, and I would think that's an even less effective tactic in the era of Web 2.0 and social media. It's not like Facebook and has thrived because of a cult of personality around Mark Zuckerberg.

You know, I think it really is that easy. One thing I learned in the past nine years of covering the Valley is that they really are outgrowths of their founders. They are very, very personal projects, and they take on the personalities of their founders in the way public companies can't. There's a place late in the book that looks at everyone's offices and how much they mirror their founders. You can blindfold me and put me in any one of them, and I could tell you immediately where I was because of the sounds and the smells. And it has nothing to do with what these companies actually do -- it's because of the founders. If you walk into Slide, you'll see these engineers designing hearts and glitter and weird, frivolous things, but it's a dead-quiet room full of people staring at Macs intensely. Everyone is in battle mode. And whenever Max [Levchin, Slide founder and PayPal co-founder] says something -- he's always surrounded by this group of his main engineers -- it's barely above a whisper. It's very intense. So people have to be incredibly quiet just they can hear what he's barking at them.

Whereas if you walk into Yelp -- which Max is an investor in and which shares a lot of similarities with Slide -- it's completely different, as it's very reflective of [cofounders] Russ [Simmons'] and Jeremy [Stoppelman's] personalities. It's very joke-y, very hip. There are a lot of women who work there, which happens to be more reflective of their site. And if you walk into Facebook, it's a like a gross dorm room. It's changed a little bit now that they've brought in other management, but up until a year ago, the main engineering floor was a dorm, and it was very much about what Mark likes.

"People always tell me the next stage of my career means moving to New York, but I never will. I don't care how that affects my career."

Considering the workaholism that's endemic to the Valley, how much time did you manage to wrangle from each of the major characters in your book, and how did you manage to even obtain so much access in the first place?

To this day, I don't know, because these are people that won't even do an hour interview with a reporter. And my average interview was four to six hours -- it was an incredible amount of time. I think that these guys think people get them wrong a lot of the time, and that's frustrating for them. They knew me well enough to know I live in the Valley and I'm not just a New York reporter parachuting in and spending an hour with them before trying to write a book. And I think they had a vested interest in wanting the story to be told correctly. The shocking thing for me during the time that I was writing my book was seeing how much of the coverage was wrong. I was frustrated by it, so I can only imagine how they felt. Beyond that, I think we just had a lot of fascinating conversations. It was almost like a therapy session for some of these guys. We talk about childhood, about relationships, about what drives them. They are so locked in, fighting for day-to-day survival as a startup that they donít get a lot of time to sit down and be forced to be so reflective. I think a lot of them enjoyed it. I was always surprised at how much time I would get. I would show up thinking I would be there for an hour, and then I would be in someone's office until they kicked me out six or eight hours later. And that was necessary -- everyone can hide who they are for an hour, but beyond that, it becomes difficult.

In the past, reporters like The New York Times' John Markoff and Fortune's Brent Schlender leveraged their early access to Jobs and Gates into sterling careers as chroniclers of the Valley. Is that your goal with this book?

Yes, and no. I always want to have San Francisco as my home and my base. I'm a business reporter -- that's what I do, and what I enjoy -- and I don't know another place on the planet that would be as fascinating to cover. The reason I enjoy being a business reporter is that it's basically about people playing a huge role in our day-to-day lives, ultimately, and I don't know where else you'd find that besides Silicon Valley. I have such an issue with people covering the Valley who aren't actually here that it would be hypocritical for me to leave and continuing to cover it. People always tell me the next stage of my career means moving to New York, but I never will. I don't care how that affects my career, and I think it's stupid that it would. But I would never call myself the next John Markoff because I think that convention has been broken; the media has changed too much. And I'm in a fortunate position where I don't have to be a staff reporter or in New York to have a steady salary and have access to write stories with a wide distribution. I'm in a position now where I can write a column for BusinessWeek in which I can choose to write about Facebook or Slide or Digg. I also have my Yahoo job, where I can tell stories in video that are completely different, and then I also have my own blog, which is more narrowly techy and insidery than the Yahoo audience. So I have more freedom and I make way more money then I would anywhere else. Ultimately, this is the only way we as reporters have any leverage in the business, because revenues are shrinking and shrinking and our responsibilities at any given publication are growing and growing.

If you were starting your career over right now, would you even attempt to work at a major publication and pay your dues, or would you hook up with some blog network or similarly newfangled enterprise? What would be the fastest path to where you are now?

I've been thinking about that a lot because I think a lot of those blogs are having trouble expanding from one voice or personality, and the main problem is that it's hard to hire away the top people from certain publications -- if they're going to go to a blog, why don't they just start their own rather than work for you? By the same token, there's a temptation to hire young people who are very enthusiastic, and then give them a voice and training, and that's probably the way I would go. But that being said, you can really tell the difference between someone who's worked at a mainstream publication and someone who hasn't. Someone who's worked at a major publication or daily goes through certain rigors and knows the rules of the game. You know when someone is trying to exploit you, and because there's such a high bar of what you can publish in any given issue, you learn how rarely rumors turn out to be true.

I do worry about people who come right out of school and just start blogging, and it's not because they aren't good at what they do, but because I would never have learned as much as I did. So, if it were me, I would go about it the same way I actually did, working very intensely at different publication, and working my way up. But I would blog at the same time, and I would probably try to do some sort of video at the same time. But I didn't necessarily have a glamorous career. I worked for maybe six or eight years in business journals and at the Silicon Valley Business Journal. And one of the reasons I have the career that I do is that all I covered was venture capital, day in and day out. If I was working at a bigger publication, I wouldn't have done that because no one would have cared, and working at small publications is great because you get to learn a lot and make mistakes on a small stage. You also don't get access granted to you. You learn how to steal it from large titles and you know how to see through a lot of things and behaviors when you do go to a large publication later. The one thing I didn't do that was kind of controversial was go work for a daily paper, because I didn't like that kind of journalism and I'm glad I didn't, because that's the business model that going totally extinct.

Your awkward interview with Mark Zuckerberg at South By Southwest this year raised the ire of an audience that was transformed into a virtual mob by the use of Twitter, thus making the event something like a scandal online. Did you find it ironic that the very phenomena you praised in your book and have spent years covering was used to tear you to shreds in front of a live audience?

It was funny. My husband had a really different reaction than mine. He wasn't in Austin, but he was obviously horrified and upset and he never wanted to use the Internet again. I guess in covering the book, I had come across so many other examples of things like that happening to other people that I wasn't particularly shocked by it because I was very aware there is an ugly side to empowering people so much. It was more hurtful and stunning on a personal level then it was a case of "Oh my god, how did this happen?" There was no real awakening about social media.

I think this was very exclusive to SXSW. I've been on stage several times since then and never been abused. I mean, SXSW is known as "Internet spring break." There are a lot of CEOs who are very big into that crowd, and then there are stuffy business people who would never speak there for that reason. A ton of powerful Valley CEOs and others wrote me after the conference and said 'I never want to do that conference after watching what happened to you.' I'd be stunned if Mark Zuckerberg did it again.

Greg Lindsay is a frequent contributor to He's currently working on his first book.

[This interview has been edited for length and clarity.]

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