The Infuriating Optimist (And His Blown Deadline)

For a capital manager who's lost $6 billion in assets, Pete Thiel has an awfully rosy worldview: The Facebook investor is calling baby boomers the "dumbest generation" and, we hear, infuriating co-workers by calling for patience at his foundering fund. More »

Where Did the Web Touch You?

Online artist Casetteboy created this funny/brilliant mashup of experts explaining "the Web." In short, the global computer network is an anti-social creep that "nailed some feces to the door," according actor Stephen Fry, Wikipedia founder Jimmy Wales and other digerati. More »

A Tech Idol's Comedown

Remember how brightly Peter Thiel's star was shining just last year? The PayPal co-founder's early Facebook investment started looking brilliant, his hedge fund returns were stellar and he debuted on the Forbes 400 list. My, how things change. More »

Peter Thiel: Too Dignified For Hedge Funds

Peter Thiel is not a clown. The PayPal co-founder and Facebook investor sees right through bubbles and rampant, ongoing Wall Street fraud, or at least says he does. So why is he running a hedge fund, again? More »

ACORN-Buster's Secret Conservative Sugar Daddy

So much for James O'Keefe as the scrappy, independent sparkplug of conservative media. The 25-year-old, who famously embarrassed ACORN on YouTube, got a five-figure sum that traces back to at least one rich conservative, well known to Silicon Valley. More »

Peter Thiel's Rough Summer

The S&P 500 is up slightly since the start of June, rising one percent, but we're told Peter Thiel's Clarium Capital is having a much worse time. In fact, the Pay Pal co-founder should avoid thinking about work this weekend. More »

Elon Musk Wants Another Obama Bailout

Elon Musk is becoming a welfare case. Federal auto-industry loans helped save his electric-car company, Tesla. Now Musk wants another federal bailout for his embarrassing space startup. And he may well get it. More »

How Crowdsourced Porn Failed

Zivity, the much-ballyhooed site where you can buy pictures from amateur models, is stripping itself of most assets and employees. Appropriate, in a way, but if amateur moviemaking and journalism can work, why not user-generated porn? Some clues: More »

Facebook Backer Peter Thiel Wants You to Know Environmentalism Will Kill Us All

Peter Thiel's objectivism and anti-immigration donations were hard enough for Silicon Valley colleagues to stomach. This attack ad he helped fund against climate-change legislation should be even less popular among California's Tesla-driving, cleantech-obsessed venture capitalists. More »

Peter Thiel's Depressing May

Even as Wall Street rallied last month, Peter Thiel's hedge fund lost close to $25 million, according to leaked documents obtained by Valleywag. Maybe this is why the PayPal founder has been grumpily calling people "frauds." More »

Peter Thiel: 'Valleywag is the Silicon Valley Equivalent of Al Qaeda'

Peter Thiel, the Facebook investor and PayPal co-founder, has never been shy about making incendiary statements. Now he's turned his guns on us.

Valleywag: An Instruction Manual

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. More »

Peter Thiel's Richer Than You, But Not as Rich as He'd Like You to Think

It's one of many casually accepted, unchecked assumptions in Silicon Valley: Peter Thiel, the cofounder of PayPal and Facebook investor, is a billionaire, right? Leaked documents from his hedge fund, Clarium Capital, show he's not. More »

What a fight! In one corner, Rhodes scholar Rachel Maddow, the liberal lesbian MSNBC commentator. In the other, arch libertarian chess master Peter Thiel, the gay Facebook investor. Best of all, they've squared off before. More »