From a distance, it must be hard to comprehend Silicon’s Valley position on the 2008 presidential election. Isn’t Stanford University, the heart of the region, a private, capitalistic university? Aren’t all rich investors and entrepreneurs siding with the party of money, Republicans? This is the capital of capital, the world-center of free enterprise, how can we support Tax & Spend Big Government Liberals? There are many answers to that, suspiciously too many, perhaps.

Let’s start with the Caviar Left posture: now that we’ve made our money, we tell others to make sacrifices. See Al Gore pontificating about carbon footprints while traveling by private jet and living in a huge energy-hungry mansion. A note in passing: Al is a partner in a Kleiner Perkins venture capital fund. John Doerr, one of Kleiner’s lead VC is a hyperactive fund raiser for Democrats. And while we note things in passing, see Colin Powell on the masthead as a Strategic Limited Partner.

A year ago, we were all for Hillary. Out with Bush and the litany of Iraq War, frightening deficit, torture, domestic spying, healthcare, education, infrastructure neglect. Not that we were in love with Hillary but, based on her and Bill’s track record, we knew she could be bought, we could do business with her. In a not so perverse way, we like Obama for the exact opposite reason: he can’t be bought. Hillary took money from big donors, from the lobbies our elected officials sold us to. Barack, on the other hand, handily outraised Hillary by an almost two to one margin, getting money from small donors, mostly on the Web. This gets us in what I think is the real reason we like Obama: He’s one of us. I’m not saying this because he’s been spotted using an iPhone. No, what we see is someone who connects with the connected generation. We see someone like us, venture investors and entrepreneurs, who holds an optimistic and meritocratic picture of the future. The latter adjective, meritocratic, got him in trouble. Used without enough discretion at a San Francisco meeting, it upset the more pessimistic market segment, the white lower middle class with a justifiably gloomy view of their prospects.

Then, while Hillary banked on her inevitability, Barack out-strategized, outraised, out-organized and outspoke her. And as inevitability switched sides, so did we. The really real reason came into play: visionary sheep that we are, we flocked to the winner. Hillary tried every dirty trick in the Clinton playbook to try and stop him. From raising prospects of Kennedy and Martin Luther King-like assassinations to bad-faith answers to questions about Obama’s own faith. What do you think of rumors that Obama is a Moslem? Instead of saying such libel had no place in a campaign for the highest office of the land, she replied she took him “at his own word he is a Christian”. The interviewer insisted: Come on, you know these rumors are false. “I take him at his own word.” Hillary had one more opportunity to rise above the gutter, to look presidential. Instead, the highly visible low blow, this was on 60 Minutes, strengthened her reputation for being Bill’s even less principled half.

I was half-kidding when I wrote above we back Obama because we like to back the winner. To us, he looks like a mestizo of JFK and MLK, minus the women and the pharmacy. To us, he looks like he will return the US to a position of exporting hope instead of exporting fear. That’s why we allow ourselves to hope we’ll make history together. In the end, how could we support the Clintons in their re-conquest of the White House, they don’t email, they don’t use Blackberries… Seriously, the BFD (Big Fundable Deal, in VC parlance) this coming week is the iPhone Applications Developers Conference in SFO. Watch this space next week. — JLG

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