Speaking of which, the crowd included Chuck Phillips, the president of Oracle; Accel Partners' Jim Breyer; Google angel investor Ram Shiram; Gavin Newsom; former California governor Jerry Brown; Jessica Guynn of the Los Angeles TimesBarron's; AllThingsD's Kara Swisher; former Chronicle editor Phil Bronstein; MarketWatch's Therese Poletti; Craig Newmark; and renowned San Francisco socialite Denise Hale, who rather liked my tie.

Zittrain's book is about the tradeoffs between freedom and control, security and creativity. New devices like the iPhone provide a safer, smoother experience than the uncontrolled Web — but at the cost of having a gatekeeper, Apple, dictating what can and can't run on the device. That kind of chokepoint, in turn, makes it far easier for government regulators to get involved. The alternative, though, is not particularly attractive: an Internet ruled by spammers and hackers.

Like his counterparts in politics, Zittrain is seeking a third way. I couldn't help but think this impulse is driven by an early experience he related at the party: Getting beaten up in high school. (He thanked the hostess, Melanie, "for not beating up on me.") Having been bullied, Zittrain doesn't want revenge: He just doesn't want anyone to bully, or be bullied. This moderating impulse is seen in a passage where he discusses how neither governments nor citizens ought to be able to wholly circumvent the law through technology:

Perhaps it is best to say that neither the governor nor the governed should be able to monopolize technological tricks. We are better off without flat-out trumps that make the world the way either regulator or target wants it to be without the need for the expenditure of some effort and
cooperation from others to make it so.

And yet Zittrain's career could well exceed Lessig's. That he was able to fill a room — an impeccably furnished, tastefully modern room in one of San Francisco's wealthiest enclaves, at that — speaks to his draw. Liberal San Francisco politicans, self-made entrepreneurs, and the Web's wacky fringe can all find things they agree on in his work.

The danger for Zittrain is that his work might be nothing more than a justification for compromise and tradeoffs. Will he find a third way for the Web — or just point out the middle of the road? His calls for a "generosity of spirit" are reminiscent of the assumptions that turned eBay, a marketplace of strangers, into a very profitable community of traders. Hoping for the best really can pan out, as it happens. But the answers Zittrain will have to find, or inspire, are far more complicated than asking someone to be on their best behavior.

"It has never been proven that Christopher Wallace was not in Las Vegas on the night Tupac was shot," Philips wrote in response to a reader's question. "Bad Boy produced some computer-generated documents purporting to place him in a recording studio in New York, but they were not time-stamped. Bad Boy said it was going to produce video of Biggie there. They never did that. I have since learned that federal officials conducted interviews in Las Vegas to determine whether Wallace was present. My sources were there and say he and other East Coast figures were in Las Vegas on the night the Southside Crips killed Tupac."

[via MTV.com]