An Interview with Sarah Lacy Regarding her New Book

When I saw Sarah Lacy's name on TheMarker COM.vention guest list, I was truly happy because I really wanted to meet her. As it happens, Sarah wanted to meet me as well, so we ended up having some great geek conversations while she visited Israel last week.

Sarah is the host of Yahoo Tech Ticker, and the writer of BusinessWeek -Valley Girl biweekly column . Between these two interesting jobs, she found the time to write her first book: Once You're Lucky. Twice You're Good. Sarah kindly accepted my request to have a short casual interview with her, so here are my questions followed by Sarah's answers:

Q - Tell us about your book
A - It's the true story of how this generation of internet companies grew out of the bubble and bust of the late 1990s. Rather than just exploring themes of web 2.0 like social networking and user generated content--it's a narrative, weaving together the stories of some of the most interesting and influential web 2.0 pioneers. Everyone from Marc Andreessen--the poster child of the first bubble and now working on his third company and funding many others--to Mark Zuckerberg--the rookie of the group, but one who was closely mentored by dotcom veterans like Sean Parker and Peter Thiel. It's an incredibly personal look at who these people are, what drives them and what they've built, gleaned through hundreds of hours of interviews-- access no other reporter has had during this time.

Q - What was the inspiration for the book's name?
A - It's sort of a saying in silicon valley among the more jaded set. Because things can happen so quickly in silicon valley and because you're so dependent on a lot of factors outside your control, building a company worth more than $1B can mean you are good or lucky. Failing outright can means you are bad or just unlucky. It's agonizingly hard to quantify, particularly if you made it during the Internet bubble. The real elite in the valley are the people who've built multiple companies worth $1B each. Then, people can't dismiss them as flukes. But it's an insane concept to people outside the valley who always wonder why these guys don't just go sit on a beach somewhere.

Q - Did you manage to isolate the journalist in you while writing this book?
A - Not totally sure what you mean, but this book clearly stretched and challenged me as a journalist. There was the obvious challenge of taking on a project so big and, I think, so important. The people in the book have been screwed over by journalists a lot--and it took a lot for some of them to trust me with their very personal stories, and in many cases vulnerable moments. I felt a huge responsibility to really get it right. That's the biggest reason I quit Businessweek to write it, rather than just going on book leave. I didn't want any distractions.

I think you're really asking about journalistic distance though, right? It's a tricky thing to talk about because "objectivity" is such a protected tenant of journalism (and rightfully so). But it depends on what you mean by it. If by objective you mean above bias, then yes I think I stayed objective. There were very hard things for me to write in this book on a human level, but I knew it was a big part of the story and they were true. If by objective you mean without opinion, then it wasn't objective. I argue a case in this book. I picked the handful of people in the book because I believed in what they were doing and in them as entrepreneurs, or web visionaries-- no matter how flawed they may personally be. When you're writing a book in 2006 that needs to be still relevant in 2008, you have to pick people you believe will still be around. So the usual silicon valley haters will say I am too "pro" everyone in the book. My answer would be, yes, that's why I picked them to be in the book. That doesn't mean I think they'll all be $1B success stories though, as I make clear.

At the end of the day there are many kinds of journalism. Writing a Businessweek article takes a stand and argues a case--it's not a newspaper article. Similarly, a book tells a story that takes a point of view. Otherwise it's just a long article. That said, I didn't think it'd be totally fair to go back to covering these guys as a normal beat reporter--either to them or me-- which is why I write a column on the web scene instead.

Q - Normally, people write about Web 2.0 on their blogs. How is a chapter in your book different from a blog post?
A - It's not only different than a blog post - it's different than an article. It's an entirely different type of content, depth of reporting and style of writing. What might be a sentence in a blog post or an "anecdote" in an article might be a 20 page scene. It's not a nitty gritty product stuff or breaking business news. Blogs are about immediacy-- books take six months to come out and need to have some shelf life. So they should never be the same. My book is the story of who these people are. I don't think that can be done in a blog post.

Q - How do you think people from the blogsphere will react to the book, and the fact that it's written by a journalist?
A - Depends on the blogger! That's what's great about the blogsphere! I know people will love it and I know people will hate it. I hope that's the case, otherwise I haven't done anything interesting. That said, it's always crushing when someone takes a cheap shot against something you poured your heart into. But that's the internet. I'm confident more people will like it than will hate it.

Q - Who is your target audience? Silicon Valley only?
A - No, not at all--the book is written for people outside silicon valley. People who have no idea what web 2.0 is, people who never heard any more about the web after the bust and then all the sudden saw MySpace YouTube and Facebook everywhere. It's the story of how we got here and why these sites are so powerful. I think silicon valley will enjoy it because there's a lot of detail and insight about these people. But that's really not the target audience (which is another reason I fully expect certain bloggers to be snarky about it--i didn't write it for them).

Q - Assuming it was part of your life for the last year, would you say it influenced the way you use Web 2.0 applications?
A - I think so. Although I already was using a ton of web 2.0 stuff because of the cover I did on Digg, that the book crew out of. I always think you have to use everything if you're going to write about these areas because they are free tools first of all, and second you don't "get" why a lot of them are so powerful unless you use them. I know so many people who've spent years SWEARING they would NEVER use Facebook and are on there now. People fight this stuff for too long. You don't have to use it all, but it's fun to try new things.

Q - When you interviewed the people that you write about in your book, did you had have the feeling that they themselves think sometimes that web2.0 are is a passing fad?
A - For most of them, i think there's always the fear--not so much because they don't believe in what they are doing, more because this sense that it can all evaporate is so ingrained in them because of living through the late 1990s. that's a big reason a lot of them sold so early.

Q - What is your next project?
A - Well, I'm a little busy right now. I am really enjoying writing a column for Businessweek. there's a certain art and challenge to doing a column and it's something I've never gotten to try before. I'm getting better--some really hit a nerve, and promote tons of love and hate mail and conversation. Then there are some no one seems to care about! It's more long-form, polished blogging. I also love working with Tom Giles, who is my editor on the column. A great editor you click with is very hard to find and can help your writing and thought process so much. I also have this 3-day-a-week show on yahoo finance, tech ticker. It's different than anything I've ever done before and has it's up days and down days, but I've learned so much in just six months about the world of video, and I think it's such a huge part of the future of journalism as it moves online. Again, I have a great mentor there in my producer Diane Galligan, who is a huge reason I took that job. I've got another year and a half on my yahoo contract, so diving into another book is pretty hard! I've also got my own blog on www.sarahlacy.com, which is only a few weeks old and is looking for its identity a bit...I'm stunned so many people have found it and are reading, and commenting on it!

That said--I do want to write another book. It was the best year of my life. Of everything I'm doing in media: book writing, on camera work, blogging, columnist- author was the role that suited my style and passions the most. I know exactly what I want to write it on, and I've even started writing the proposal. But it's a huge undertaking and I need a break before diving back into it again. So I'm sort of grateful I have this yahoo contract in place! My most important priority is making sure this book is a success--because that will determine a lot of my opportunities in the future.

Q - Finally: What are you reading right now?
A - I have been trying to get through Anna Karenina by Tolstoy for a while now. My Mom--a Russian lit scholar--got me a new translation and wanted me to read it. It's tremendous but doesn't exactly fly.... this trip I've been reading "The Israelis" by Donna Rosenthal. The Israeli consulate gave it to me before our "traveling geeks" blogger trip and it's amazing to read it as I've been in Israel for the first time.

Book due to be published in May 15, 2008 -Available for pre-order at Amazon or Barnes & Noble.

Being connected to the web 24/7 (almost), I don't usually have time for books, but I'm planning on finding special time for this one. Although... it would be helpful to get it on an audio-book and listen to it on-the-go.. (just an idea)

Stay updated through Sarah's Facebook page, and be sure to subscribe to her new blog, simply because it's good.