Dear Ryan:

As I head to NBC to run its Bay Area site, I'm leaving you one Silicon Valley gossip blog, used but in good condition. A few thoughts on how to keep it that way.

I still remember the day I called you up and tried to recruit you to Valleywag — only to learn that that sneaky rapscallion Nick Denton had beaten me to the punch by one whole day in offering you the night shift at Gawker. It all worked out in the end — and perhaps better than I could have imagined back in 2007. But the main lesson I take away from that is that you can get Denton to do pretty much whatever you want if you're patient enough.

Denton, who has a weakness for idle truisms, likes to say that gossip is a young man's game. But you're old enough to remember the first dotcom bubble, and how it popped. That's going to be key in the next few years. We may escape a depression, but Silicon Valley is facing a reckoning nonetheless. Too much venture capital chased too few idea for far too long — and a buoyant economy can no longer hide the startup factory's mistakes.

The biggest mistake you can make is getting too close to your Valley sources and fall for their groupthink in order to ingratiate yourself. (You know how I've scolded you for gullibly buying the hype that Twitter is an amazing source of real-time news. Okay, perhaps it was — for five seconds, before the blowhards, spammers, and self-promoters found it.) At least your schooling will help you remain an outsider: As a Berkeley grad, you'll have an instinctive dislike for the Valley's Stanford in-crowd.

At the same time, don't forget that your years living, studying, and working in the Bay Area give you a better understanding of your beat than anyone can have from 3,000 miles away. Gabriel and Nick, though well-intentioned, have the Manhattan media habit of confusing proximity with relevance. Gawker is much more than New York now — and Valleywag's unique place therein must be firmly grounded in northern California's shaky soil.

Remember: Love is far more powerful than hate. Keep a clear-eyed passion for the Valley. Most tech reporters here secretly loathe their subjects, but try to disguise it with a supine gladhandery as they beg for scoops about new startup website features. They hate themselves and the people they write about. Sad, right? By loving the Valley, you can write about it more honestly than any of them. Just prepare to have your heart broken again, and again, and again. To truly love something, you must love it with all its failings.

For example, the Valley's Alice-in-Wonderland economics — why is Twitter worth more than most startups precisely because it has no revenues to speak of? But the thing you must love most about Silicon Valley — the part of the story the local press corps always skips over in favor of buzzwords, punditry, and lazy analysis — is its people.

The Valley's story is not one of chips and code. It is not a tale of technology. It is the always-running tragicomedy of the people who make technology.

Here are a few characters to watch. I hope it helps — but I can't wait to see who you add to the list.

Marissa Mayer Valleywag's first story remains its best. The public face of Google, Mayer also runs search, the only business that matters there. The cupcake frosting of her girly image — one she assiduously advances at every opportunity — may humanize the otherwise robotic computer scientist. But it is a distraction. The real question to ask about Mayer: Does her spreadsheet-ridden management style scale to new problems beyond search? Are her strengths now turning into limitations?

Mark Zuckerberg Ignore the nerd façade. Facebook's 25-year-old CEO is headstrong and ruthless. Here's the grand irony of Zuckerberg's revolutionary venture: He claims to be all about openness and sharing. But his imperious, my-way-or-the-highway management style has created a fractious culture of dishonesty, delusion, and disillusionment at the social network. His underlings either learn to say things they don't believe, or they move on. This is why Sheryl Sandberg is exactly the wrong COO for Zuckerberg. The veteran of the Clinton Administration has forgotten her Google training and reverted to Washington-player form, where staying on message is all that counts. Facebook's best hope is that Zuckerberg learns from his mistakes — but first he has to recognize them as mistakes.

Carol Bartz Yahoo's CEO swears like a sailor. At last, a boss who has found the right language to describe Yahoo's plight! Bartz brings a refreshing frankness to Yahoo. But the already demoralized troops she inherited will need to start seeing results. Otherwise, Valleywag will continue to be a steady recipient of leaks from Sunnyvale.

Elon Musk The CEO of Tesla Motors and SpaceX is living the geek high life, playing with fast cars, rocket ships, and other people's money. It's wonderful that Musk has realized even a small part of his childhood fantasies. But he risks destroying his dreams by refusing to reconcile them with reality. Factcheck everything Musk says. For example, was he actually running either Zip2 or PayPal, the previous dotcom successes he likes to cite in his bio, when they were sold?

Owen Van Natta Everyone is going to give MySpace's new CEO a pass, because the so-called "social portal" is so clearly troubled. If the former Facebook executive succeeds in a turnaround, it will be viewed as an astonishing achievement; if he fails, people will say no one could save MySpace. That's not fair. Hold his feet to the fire, and judge this disturbingly tan rock-star boss like anyone else on the list.

Peter Thiel Thiel, the PayPal cofounder, likes to brag about how he recruits only the best brains from the best schools to work at Clarium Capital, his hedge fund. Oh, really? Take a look at their résumés on LinkedIn. Like so many of this outspokenly harebrained libertarian's theses, the claim sounds good on paper but doesn't stand up to inspection. Valleywag, alone in Silicon Valley, can take a keen look at Thiel's rhetoric without being dazzled by his inflated wealth.

Tim Armstrong Like Van Natta at MySpace, Armstrong, a Google golden boy now charged with running AOL, will be enjoying a honeymoon. Don't worry: There are plenty of disgruntled AOLers who will gladly help you break up the lovefest.

Jimmy Wales Remind me: What does Wikipedia's founder actually do to earn his keep, besides give speeches? In all this time, I was never able to figure that out. Maybe you can!

Eric Schmidt When did Google's CEO turn into such a raging egomaniac? When the blogosphere was the only corner of the Internet that criticized him, he dismissed it as a "cesspool." But now everyone from Hollywood to the New York Times to the Federal Trade Commission is looking askance at his online empire's practices. "Don't be evil" has turned into "don't get caught." He will, though. Be ready when he does.

Larry Page and Sergey Brin Google's wonder twins have achieved geek nirvana, creating a cloistered campus with free food, lava lamps, and exercise balls to spare. They have a fleet of jets to transport them to rocket launches or rendezvous with Richard Branson and Bono. They've even managed to get married and reproduce. Just one question: Are they still sane? Were they ever?

There are many people who will help you — many of the same people who helped me so much, I hope. They include:

  • Nick Denton, for putting up with three years of playing hard to get — and then putting up with much more besides.
  • Brian Lam, Choire Sicha, Noah Robischon and Lockhart Steele, for tag-teaming me into taking the job.
  • Gabriel Snyder, for expertly steering Valleywag into Gawker's welcoming arms.
  • All the Valleywaggers: Paul Boutin, Nick Douglas, Megan McCarthy, Tim Faulkner, Mary Jane Irwin, Jordan Golson, Nicholas Carlson, Jackson West, Melissa Gira Grant, and Tim Woolery. You guys, we've been through so much together!
  • Richard Blakeley: We made sweet Photoshop magic together.
  • Everyone at Gawker Media: How much do I love you? Far more than just five milligrams.
  • Sarah Lacy, Kara Swisher, and Peter Kafka: My peers and fellow purveyors of Valley gossip, you constantly inspired me.
  • Countless sources, tipsters, and fellow scribes: Please understand that I esteem you none the less for not naming you here. In fact, your continued anonymity is the best sign of my abiding affection.

Good luck, Ryan. I'll be reading eagerly.

Don't screw it up.


The Valleywag

(Photos by Brian Solis and Scott Beale/Laughing Squid)