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The Rappaports and others are pouring money into organizations created in 2003-2004, and are even founding new independent political advocacy groups, which they say are devoted to developing a new liberal "idea infrastructure" that will shift America leftward during the next 20 or so years.
"We're like a farm team for the future of the Democratic Party," Deborah Rappaport told me at a liberal-group cocktail party in San Francisco about a month prior to the San Mateo gathering.
With even more intensity than before, the groups are being rewired with concepts, jargon, and personnel from the hard-nosed tech business world.
"The philosophy is we're looking for growth markets," Seitz Gruwell says.
Somehow this talk seems to have a texture similar to the grains of truth buried amid boulders of wishful thinking that characterized the venture-capital-funded dot-com boom. Then, as now, rich financiers threw money at talented kids based on a story about a new and different future.
Back then, wealthy patrons and young entrepreneurs repeated a story about an emerging New Economy based on widespread broadband access to the World Wide Web. Nobody seemed to notice that telecom monopolies were delaying broadband rollout, and choking off dot-com dreams.
The new liberal-money-matrix story seems faulty in similar ways. There's a devastating phenomenon that's choking off these vast-liberal-conspiracy dreams that nobody seems to pay much mind to. It's called urban sprawl.
America has been turning rightward for the past half-century not because of Cato Institute policy monographs.
America's becoming more conservative, and Republicans have seized power, because the real $300 million conservative message machine is America's expanding suburbs and exurbs. They've been growing as Democratic heartland cities have stagnated for 50 years.
All the talk of animating young voters, of creating a progressive idea infrastructure, or of applying the virtues of the high-tech investment business to leftist political entrepreneurialism is at best a sideshow compared to this. It's a phenomenon nobody in the world of multimillionaire-funded liberal activism seems interested in addressing.
This demographic shift is the result of hundreds of thousands of local political decisions to prevent new homes from being built in cities, and thus divert housing demand into cul-de-sac construction in formerly rural areas. Building new apartments inside cities, and next to residents with the money, savvy, and leftist rhetoric to prevent them, means developers must run the equivalent of a political campaign. It's the type of campaign that would be well served by armies of young idealistic liberal operatives funded by progressive billionaires.
Somehow, though, I find it hard to envision the Rappaports telling Neitzel and Music for America founder Dan Droller, 25, to report to a city council meeting to speak on behalf of a high-rise condominium developer after they've finished passing out anti-military-recruitment fliers at a SambaDá concert.
Instead, these outside efforts to reinvent the Democratic Party are taking an easier, more enjoyable, but probably less effective path and ignoring liberalism's giant demographic problem.
Standing, red wine in hand, in the San Mateo fern bar with smart, talkative, venture-capital-backed young people, I sensed déjà vu. After hearing the term "$300 million conservative message machine" for the umpteenth time, I realized I was breathing that old venture-capitalism byproduct called vaporware.
The online encyclopedia Wikipedia, despite its faults, is a useful guide to agreed-upon popular wisdom among Internet-savvy people who feel strongly about a particular topic. Under the heading "Republican," a Wikipedia article suggests the existence of three possible scenarios under which the current, more or less 50-50 standoff between America's two political parties could tilt long term in either direction.
One possible wild-card scenario is the emergence of more young voters. John Kerry received 56 percent of votes from 18- to 29-year-olds in 2004, one of the few significant demographic groups whose behavior changed in the Democratic Party's favor that November. More young Americans go to college than used to, and college grads tend to vote Democratic. America's current crop of youngsters includes more minority group members than previous generations, suggesting this traditional Democratic constituency is growing.
"There's a belief that young people don't vote, so why should we spend money on them. We have a huge opportunity with them because of their size, and because of their demographics. It's a real opportunity for Democrats and progressives to motivate this generation," Seitz Gruwell says.
With this in mind, liberal advocacy groups focusing on young people sprouted up all over America in 2004, and more seem to be announcing their birth every day. Music for America, which helped get out the 2004 young vote by helping politicize rock musicians, is an example of this kind of group.
Another key factor could be Hispanics, a group that voted 64 percent for Al Gore in 2000, and, according to different exit polls, somewhere between 54 percent and 58 percent for Kerry in 2004. Republicans hope this rightward trend will continue. Democrats hope it won't, and that a growing overall majority-Democrat Hispanic population will bolster party fortunes. To this end, the party, and left-wing independent groups such as the New Democrat Network and People for the American Way, are targeting the Latino vote.
In scenario three, the half-century-old expansion of U.S. suburbs, whose residents tend to vote Republican, continues apace, smothering Democrats' national prospects.