A Valleywag reader recently asked us what reading material best explains the players and games of the tech world. We decided to come up with a list—and ask for your input as well.
A writer, new to Silicon Valley, recently asked us how to understand the young Turks of Silicon Valley through books, magazine articles, etc. We also thought he might like to know about some of the tech world's more grizzled veterans—the ones with stories about old battles that seem to keep repeating themselves. And, oh yeah, maybe a bit about technology and social change while he was at it.
Below we've listed some of our selections, a mix of books, magazine articles and online essays, with a decided focus on the gossipy, the blunt, the obsessive and the power-mad. If you've got something to add, post in the comments or shoot us an email—we plan to update this post.
On Facebook: Accidental Billionaires, Ben Mezrich.
Valleywag take: We admit we were skeptical, given Mezrich's truth-challenge authorial history and his over-the-top book proposal. But it turns out the slipshod fact-checking and occasional fictionalization help Mezrich paint a fast-moving and broadly interesting story about Zuckerberg, which turns out to be a great thing for readers who know little about the Facebook CEO or the social network he founded. And Mezrich's past communions with Hollywood help the writer see past technical nerdery into the personal stories and power struggles that shaped Facebook into what it is today.
Bonus reading: If you read this as quickly as we did, you might want to pick up Fortune writer David Kirkpatrick's widely-excerpted The Facebook Effect when it drops next month.
On startups: Founders at Work, Jessica Livingston
Valleywag take: Page for page, this underhyped book is probably the best primer on Silicon Valley startup life going. Livingston, a partner at startup incubator Y Combinator, interviews more than 30 startup founders (listed here), including PayPal's Max Levchin, Twitter's Ev Williams and Flickr's Caterina Fake. But what's surprising about the book is how fascinating it is to read founders talking about startups you've never even heard of. By going straight to the entrepreneurs behind Silicon Valley's success stories, Livingston managed to get a taste of everything, including the grinding day-to-day operational struggles glossed over in the mainstream press, plus some of the behind the scenes bloodsport ignored in the officially-sanctioned hagiographies.
Bonus reading:: The similarly structured Coders at Work, by Peter Seibel, is a fun follow-on read for those with a technical bent.
On Google: The Search: How Google and Its Rivals Rewrote the Rules of Business and Transformed Our Culture, John Battelle
Valleywag take: Still the definitive take on Google's high command, Batelle's 2005 book was a savvy, insider's look at the company, offering glimpses into how the top three Googlers share power (two-against-one votes are common), hold the rest of the world at arm's length (the co-founders display a surprising apathy and ignorance toward the Patriot Act), and started their juggernaut while stil graduate students (a porch, a demo and a $100,000 check to a non-existent corporation were all involved).
Bonus reading: Longtime technology journalist Richard Brandt's Inside Larry And Sergey's Brain is thoroughly reported, well reviewed and, since it was published this past September, packed with information on more recent happenings at the Googleplex, like Google Books and the increasingly elitist internal culture.
On Apple: The Second Coming of Steve Jobs, Alan Deutschman
Valleywag take: Jobs has become something of a business and technology messiah lately, but there was a time when Jobs was lost in the wilderness — cast ouf from Apple, struggling to make money at NeXT and pumping his fortune into this thing called Pixar no one had ever heard of. By focusing on this dark period and on Jobs' messy reconquest of Apple, Deutschman got a darker and more revealing portrait of Jobs. Not just the polished Jobs from the keynote stage, but the Jobs who screams insults at reporters, fires employees with breathtaking speed and who could deliver profane critiques that reduced underlings to tears. Needless to say, Jobs went nuclear when the book was published in 2001, calling the CEO of Random House and possibly derailing the original cover photo and an excerpt that had been planned in Vanity Fair.
On Web 2.0: Once You're Lucky, Twice You're Good, Sarah Lacy
Valleywag take: This iteration of Valleywag hasn't read the former BusinessWeek writer's book on the Valley's young social media savants, but any work that's received so much coverage in our own pages must have some worthwhile relevance to our readers.
On dealmaking: High Stakes, No Prisoners, Charles Ferguson
Valleywag take: An MIT professor started the company that created FrontPage, the early Web-page building software, sold his company to Microsoft and then wrote this detailed, scathingly brutal book about everyone he met along the way, amid the insanity of the first dot-com boom.
Bonus reading: Michael Lewis' Burn Rate is in a similar, "now I can say what I really thought" vein, but with more of a focus on New York than Silicon Valley and on media rather than tech. Wolff is arguably a better writer, with a better ear for humor, while Ferguson has a better grasp on the technical ramifications of his product.
On MySpace: Stealing MySpace, Julia Angwin
Valleywag take: Why MySpace is dying, and why you should sell your startup to News Corp. for the money but not for its future — all the answers are here, along with the inspiring story of how some porn-trafficking scam artists started one of the most successful social networks ever devised. If Chris DeWolfe can do it, anyone can!
On old media-new media mergers: There Must Be a Pony in Here Somewhere, Kara Swisher
Valleywag take: The definitive, and darkly hilarious, story of how an epic corporate merger, between AOL and Time Warner, went so horribly, horribly wrong. The trainwreck of a merger you probably should stare at for a clue as to why companies like Facebook are so reluctant to sell.
On technical battlefields: How Microsoft Lost the API War, Joel Spolsky
Valleywag take: One of the best tech essayists going — and a former Microsoft program manager — explained how the software company in Redmond, Washington fumbled its future so badly, and why we'll all be writing Web apps for the foreseeable future.
Bonus reading: Joel's "Top 10" essays, as listed in the right margin of the homepage for his website Joel on Software.
On social networking: A Group is It's Own Worst Enemy, Clay Shirky
Valleywag take: An heroic and prescient look at the patterns that keep repeating themselves — and the lessons that keep getting unlearned — in the surprisingly long history of social software. Useful to anyone organizing or investing in online communities, which these days is a lot of people.
Bonus reading: Shirky's influential book Here Comes Everybody, and another essay, Situated Software, which explains why no one talks about "scalability" any more.
Surely we've missed something; you'll notice there's nothing on Twitter in here, and somehow we managed to include nothing by Paul Graham, an entrepreneur turned angel investor and essayist, or by Philip Greenspun, an influential startup founder and pioneer in online communities. If you've got suggestions, send them our way.