Both Maddow and Thiel went to Stanford. They overlapped for a couple of years in the early '90s. Thiel, who had already gotten his undergraduate degree and was enrolled in law school, had started the Stanford Review, a conservative newspaper, to campaign against the college's move away from a curriculum which favored the great works of Western literature. Maddow was a progressive activist stomping around in combat boots and a shaved head. We hear that Thiel and Maddow had some kind of noisy on-campus altercation. Through a spokeswoman, Maddow says she doesn't remember a run-in with Thiel. Any Stanford grads care to enlighten us on what the two had to say to each other?

Thiel, who has suggested America would be better off if women had never gotten the vote, now calls his views on women's suffrage a "commonplace statistical observation." We think these two school chums are overdue for a reunion. They both now live in Manhattan. Isn't it time Thiel pops over to the studio for an interview on the Rachel Maddow Show? There's so much for them to catch up on!

(Maddow photo by Frederick M. Brown/Getty Images; Thiel by davidorban)

Thiel is the former CEO of PayPal who now runs the $2 billion hedge fund Clarium Capital and a venture-capital firm called the Founders Fund. His best-returning investment to date, though, has been Facebook. His $500,000 investment is now worth north of $100 million even by the most conservative valuations of the social network.

On the side, though, his pet passion is libertarianism and the fantasy that everything would be better in the world if government just quit nagging everybody. But, now he's given up hope on achieving his vision through political means because, as he writes in Cato Unbound, a website run by the Cato Institute, all those voting females have wrecked things:

The 1920s were the last decade in American history during which one could be genuinely optimistic about politics. Since 1920, the vast increase in welfare beneficiaries and the extension of the franchise to women - two constituencies that are notoriously tough for libertarians - have rendered the notion of "capitalist democracy" into an oxymoron.

So there you have it: The problem with women is that they don't vote like their menfolk tell them. We would have so much more freedom, Thiel suggests, if only we'd deprived women of it.

You may wonder: Is Thiel on drugs? The answer, according to Thiel, is yes:

As a young lawyer and trader in Manhattan in the 1990s, I began to understand why so many become disillusioned after college. The world appears too big a place. Rather than fight the relentless indifference of the universe, many of my saner peers retreated to tending their small gardens. The higher one's IQ, the more pessimistic one became about free-market politics - capitalism simply is not that popular with the crowd. Among the smartest conservatives, this pessimism often manifested in heroic drinking; the smartest libertarians, by contrast, had fewer hang-ups about positive law and escaped not only to alcohol but beyond it.

"Positive law" is Libertarian-speak for laws which proscribe certain activities, such as taking drugs. Translate Thiel's language, and you'll see that he's saying anyone in his generation who wasn't taking drugs was an idiot. Which squares with rumors we'd heard about Thiel during his PayPal days, especially while he was fitfully coming out as a gay man. With a life like that, we can understand Thiel's visceral dislike of the government. But what did women ever do to him?

Yammer is a business-friendly copy of Twitter. It's an offshoot of Geni, a Web-based genealogy site started by former PayPal COO David Sacks, which raised $100 million in venture capital last year. TechCrunch50's prize panel, composed of Arrington and a few TechCrunch insiders (shown here, in a spy photo taken at the event), passed over more promising startups like FitBit, the maker of a wellness-monitoring gadget.

Quality aside, a sense of fairness might have led Arrington to give Yammer the skip: Neither Sacks nor Geni needed the $50,000 prize. Arrington's crush on Geni has been obvious since before its launch. (Most recently, he claimed Geni had close to a million visitors a month in August; according to a link to Compete.com Arrington himself included in his writeup, it's actually 400,000, a fraction of the audience enjoyed by established genealogy sites like Ancestry.com and MyHeritage.)

The problem with events like this is no one is unconflicted. But Sacks is in particularly deep: His former boss at PayPal, Peter Thiel, now runs VC firm Founders Fund, one of TechCrunch50's sponsors. Arrington has long been rumored to favor startups backed by the VCs who sponsor his event. He brags that he doesn't charge startups directly to appear on stage. But he seems to like to have them in his pocket, one way or another.

Ignominiously, the botched launch ended up splashing the ashes of James Doohan, the actor who play Scotty in Star Trek's ashes all over the Pacific. Perhaps more materially, three satellites — two from NASA and another form the department of defense — also saw their trips cut drastically short. Thiel's $20 million follows $100 million of Musk's own money already sunk into the project. As friendly as the two are now, Thiel's investment has to be humiliating — a reminder that Musk may have the occasional clever idea, but it takes a Thiel to make it pay off.

• Joe Green (top left) has raised $7.3 million for his Facebook application, Causes. Which would be more impressive had the funding not come from Peter Thiel's Founders Fund. Thiel is an investor in Facebook, and has a vested interest in creating the impression that Facebook appmakers are worth something.
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• Drew Houston (not pictured) runs a company, Dropbox, which offers online file storage, a service users can't get from anyone else. Except AOL, Google, Microsoft, and Yahoo, and a good dozen other startups.
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• VideoEgg CEO Matt Sanchez (top, second from left) tried to compete with YouTube and failed. Or "evolved," as BusinessWeek put it, into an ad network for Flash games, a crowded field that so far has garnered VideoEgg gross revenues of $300,000 a month. The magazine lauded Sanchez for raising $27 million in venture funding; it should have asked instead how much is left.
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• RockYou cofounder Jia Shen (bottom left) launched his widget startup while working for another company, Iconix, according to IM chats produced in court. He and cofounder Lance Tokuda settled a lawsuit with iconix last year. They're now trying — so far unsuccessfully — to raise another round of venture funding, or sell the company.

Quantcast is a fine and worthy startup. Its investors include Peter Thiel's Founders Fund. Along with Compete.com, it's bringing a much-needed shakeup to the arcane business of Web-usage statistics. Quantcast's twist is that it measures website usage directly, as well as estimating it from surveys, as others do.

That, of course, is a subject of keen interest to the online media, to which Quantcast has catered expertly. (Gawker Media, the publisher of Valleywag, is a Quantcast customer.) Look no further than its widget-measurement service. Widgets — those bits of website code embedded on other Web pages — are a fad these days among Web publishers, and Quantcast promises to count not just regular website visitors, but users of other sites who see their widgets. Measuring widgets will likely just result in a swifter understanding of their irrelevance, but in the meantime, the flourish garners Quantcast attention from widget-obsessed publishers.

More attention than it deserves, though. Even with $20 million in the bank, Quantcast faces much larger competitors. And who does it serve outside of a circle of midsized Web publishers, too small for the current rating services but big enough to attract real advertisers? The size of that audience is what anyone rating Quantcast's chances should measure.

The San Francisco startup, known for its social apps on Facebook and MySpace, last took funding in 2006 — about $20 million from BlueRun Ventures, Peter Thiel's Founders Fund, Khosla Ventures, and the Mayfield Fund. Maybe now Levchin can get some sleep. (Photo by flawedartist)

Clarium already has an office in New York, and Thiel an apartment there. So the move would have more of an effect on his employees than on Thiel. As brainy as the Valley is, financial expertise is still centered in New York, as are the deep pools of capital Thiel would tap. For Clarium's existing workers who might be asked to move, the prospect is unsettling.

There is one other aspect to Thiel's move that fascinates. I've been told Thiel has been dating Matt Danzeisen, a vice president at BlackRock, for some time and the handsome fellow pictured above to the right of Thiel. (No one has yet confirmed for me if they're still going steady.)

An acquaintance of Thiel scoffs at the idea that Thiel would do anything for romantic reasons. Thiel, he says, is an utterly rational thinker. But the heart is capable of its own rationalizations. The mere possibilty that Thiel might maximize happiness, rather than profit, is a comforting thought.

Technically, the sale makes sense. Plaxo's chief platform architect, Joseph Smarr, is an engineering rock star, with many fans among the Valley's brainiac collectors. And Facebook CEO Mark Zuckerberg is said to admire other members of Plaxo's engineering team. The process of synching multiple address books, Plaxo's specialty, is more complex than it sounds, and would save Facebook some trouble as it tries to become more of a hub for its users' online activities on and off the Facebook site.

Bringing the investors to terms, however, would prove troublesome. Michael Moritz, of Sequoia Capital, is said to be eager to get a stake in Facebook, however small, so it can claim to have had a hand in its success. It's a move he played skillfully in the first bubble when he merged a failing online bank, X.com, into Peter Thiel's PayPal.

Thiel, now a Facebook board member and venture capitalist in his own right, remembers that maneuver all too keenly, and believes Moritz got the better of him in the deal. Then, too, Moritz forced Sean Parker, now a partner in Thiel's Founders Fund, out of Plaxo; he next joined Facebook, and while he didn't stay long, he still owns a substantial stake in the company. Any deal that reunites Sequoia, Thiel, and Parker would produce a moment of boardroom drama the likes of which we haven't seen in a long while.

The talks aren't advanced, and haven't even reached the point of naming numbers. But Facebook's lofty $15 billion valuation gives it a currency for acquisitions. Will Plaxo take Facebook's paper? The decision, if it ever comes to that, will rest in part with Thiel. How delicious it would be to have Moritz at a disadvantage.

Venture capital is a business about risk — but only the right kinds of risk. Unproven technology? Fine. Gay employees? Cool. A founder who quotes Ayn Rand? Oh, hey, wait a second. Not that there's anything wrong with The Fountainhead.

Here in northern California, where John Galt's 60-page speech in the middle of Atlas Shrugged is the only thing we can't tolerate, even alluding to someone's Objectivism is suspect. (Even if, like me, you kinda bought into it as an MIT freshman because it made more sense than either Catholicism or Sartre.) But on Sand Hill Road, Republicans fund Republicans. The clubby ranks of VCs are mostly straight, white, male and support the nation-state as sole arbiter on the use of force.

The effects are hard to document. But Objectivist entrepreneurs I've spoken to agree it's real. How many VCs do you know who can grasp Rand's basic math that A=A? It explains the valuations for Web 2.0.

I think it explains a lot about Thiel: "The only man capable of experiencing a profound romantic love is the man driven by passion for his work." Like the Jews who founded Hollywood a century ago, an Objectivist investor has no hope of getting elected to anything. That frees him or her to build a rational system for identifying and rewarding talented individuals. Starting with himself.

That's why I think it's important to say this: Peter Thiel, the smartest VC in the world, is an Objectivist. Dude, come listen to Rush with us anytime.

Venture capital is a business about risk — but only the right kinds of risk. Unproven technology? Fine. A host of rivals? No problem. A gay founder? Oh, hey, wait a second. Not that there's anything wrong with that. But someone else, somewhere else, might take issue with it. That's VC thinking.

"Of course he's gay. Why would you mention that?" Here in northern California, where intolerance is the only thing we can't tolerate, even alluding to someone's sexual orientation is suspect. (Even if, like me, you're gay yourself.) Yet as one venture capitalist put it, "The VC industry is headquartered in Menlo Park, not northern California." On Sand Hill Road, like funds like. The clubby ranks of VCs are mostly straight, white and male. They instinctively prefer entrepreneurs who remind them of themselves. At best, it's a wrongheaded sense of caution. At worst, it's prejudice with a handy alibi.

The effects are hard to document. VCs fund so few of the companies they talk to that it's hard to prove a case of discrimination; there are a hundred reasons why they might pass on any given startup. But gay and lesbian entrepreneurs I've spoken to agree it's real. PlanetOut, the gay and lesbian portal, had to buy out Sequoia Capital, which had come to regret its investment in the company, before it found braver VCs and eventually went public. And really: How many out gay VCs do you know?

I think it explains a lot about Thiel: His disdain for convention, his quest to overturn established rules. Like the immigrant Jews who created Hollywood a century ago, a gay investor has no way to fit into the old establishment. That frees him or her to build a different, hopefully better system for identifying and rewarding talented individuals, and unleashing their work on the world.

That's why I think it's important to say this: Peter Thiel, the smartest VC in the world, is gay. More power to him.

But Zuckerberg's most important backer, Peter Thiel, does not work on Sand Hill Road. From his offices in San Francisco's Presidio, he's set about changing the rules of how startups get funding and how founders make their fortunes. Through his Founders Fund, he has begun issuing "Series FF" shares to the entrepreneurs he backs, giving them the right to sell shares alongside their companies to new investors. Thiel, who felt unjustly treated as the cofounder of PayPal, wants to let his protégés build companies without worrying about how to make rent.

Old lions like angel investor Ron Conway will probably view this development with outrage. They feel entrepreneurs, with no capital at risk, should not become rich until well after their already wealthy backers get paid, Today's startup generation begs to differ. The IPO market is still a shadow of its former self, and sales to large companies are an unreliable route to wealth — and a sure way to lose control of one's company. Meanwhile, vast pools of private money are waiting to be tapped.

Zuckerberg still owns nearly a third of Facebook . If the rumors are true, even if Facebook flops, the 23 year old would be set for life.

Update: An unimpeachable source says the sale didn't happen. Was I played? Perhaps so. Read my followup on why I think this rumor spread — and what its purveyors may have hoped to accomplish.

Personal Assistant, The Founders Fund

Two of the GPs are seeking a full-time personal assistant to help them manage their personal lives so they can focus on building The Founders Fund.

In addition to a strong professional track record, the best candidates for this position will be attentive to detail, respectful of confidentiality, very reliable, responsible, and organized, and OK with a highly variable schedule. Experience with basic computer software and access to a car are required.

Primary job functions will include:

* Manage personal travel.
* Manage personal calendar.
* Manage GP residence.
* Personal shopping/running errands.
* Miscellaneous research.
* Event planning.
* Paying bills.
* Misc. and other projects.

Compensation is competitive and negotiable based on experience.

Health insurance is provided.

Please email your resume for any of these positions to me or Ofa Taufalele at ofa@foundersfund.com.

He could simply be showing off, of course. But membership in a network gives you privileges on Facebook not extended to ordinary users; you can view the profiles of people in those networks, even if they don't list you as a friend. What Parker is doing, in other words, isn't just boastful; it's a little bit creepy. (Parker is currently dating Kate Jurkiewicz, a member of Facebook's UCLA network. One wonders how she and Parker met. And if Parker enjoys reading up on her college friends' antics.)

By all rights, Parker should have his Facebook account terminated. The site's terms of service are clear on this point: No user may

... impersonate any person or entity, or falsely state or otherwise misrepresent yourself, your age or your affiliation with any person or entity