John Roos, CEO, Wilson Sonsini Goodrich & Rosati: When many of us first met with him, Obama was a classic Silicon Valley startup. Literally, he had to make the decision to run within those couple of weeks from Christmas 2006 to the beginning of January 2007, and in that period he sought startup financing to get off the ground. You had an unbelievable political brand in the Clintons, and this young rising star taking that on as a long shot. If you look at any startup, Google being a prime example, the initial odds are typically viewed as being almost insurmountable. But we take those kinds of bets.
Tony West, partner, Morrison & Foerster: I had met him during his U.S. Senate campaign. He’s  always had a very natural tie to Silicon Valley that he’s cultivated. In 2004, he came out here for a day to campaign for my sister-in-law Kamala Harris, who was running for San Francisco district attorney, and he was intensely curious to figure out what was going on out here that was so exciting. He has a philosophy of approaching challenges that is very entrepreneurial. That’s something you have to develop as a community organizer, because it’s such a difficult job.
Steve Spinner, startup investor: I think Barack spoke to us because we live this every day. Most of what we do has never been done before, and people tell us we’re crazy to even consider it. But this valley knows that if you have a well-thought-out idea with a good strategy and plan, and you surround that with a clear vision, a passionate leader, and an experienced management team, you can be successful.
John Roos: A friend told me that Obama was heading toward a potential announcement and asked if I would be willing to sit down with him. I went to D.C. for Nancy Pelosi’s swearing-in and met with him then. His vision was that the change would come from all of us and not from him. He was the person who was encapsulating the energy, the message, and everything else, but it was going to be an election from the ground up.
Christine Pelosi: Necessity being the mother of invention, he had no choice. It had to be done from the bottom up. Why? Because Hillary Clinton was the juggernaut.
Peter Leyden: She had all the big donors. She had all the special interests. She had basically every relationship locked down—more than any candidate before that. Even frickin’ Gavin Newsom, she had him by the balls. Obama had to have a new way to raise money and blow her away.
Andy Rappaport: Campaigns tend to be lumbering, hierarchical things that succeed despite their inherent ineffectiveness. And Obama’s team said, “You can’t out–General Motors Hillary Clinton, right? So if there’s a means by which the upstarts take on the establishment, we should learn that. What’s that Google thing? How did that happen?”
Joan Walsh, editor-in-chief, Salon.com: Hillary sorta missed Google and Silicon Valley. With all of Al Gore’s connections down there, that might be why. She relied on a somewhat outdated approach to California donors and where the money was—Hollywood more than the Valley.
Steve Spinner: Other candidates had gone to all the leading fundraisers in the Valley. But the Obama campaign did a much better job of meeting and exciting them.
Chris Lehane, former Bill Clinton aide: I mean, the 415/650/510 is not only the latte-liberal capital of the world, it’s the epicenter of the online world that is reshaping how the world looks and interacts.
Mark Gorenberg, managing director, Hummer Winblad Venture Partners: Obama looked at technology as a differentiator, just like startup companies do.
Christine Pelosi: He is a man who, in his mid-40s, came up professionally online. I worked on Capitol Hill, and some people there still think BlackBerrys are for jelly and not for communications.
Tony West: He was never without his BlackBerry.
Christine Pelosi: It’s the difference between having someone who leaves tech stuff to the interns and someone who understands the Internet’s libertar­ian streak.
David Talbot: There was also the racial mix. To me, the Bay Area is the land of the racial mix. The first event I went to, a big percentage of the crowd was wealthy Indian entrepreneurs.
Joan Walsh: I heard Maria Shriver say that if Obama were a state, he’d be California. It’s kinda hokey but true on a lot of levels—mixed and young and forward-thinking.
Mark Gorenberg: It was very fast. There was this almost instantaneous combustion in Silicon Valley.
Andy Rappaport: It was, “Wow, this Barack Obama guy, he looks terrific. Let’s get behind him. Let’s make it happen.”
Tony West: The very first event held for him in California was a huge gathering at John Roos’s house, where checks were written to his exploratory committee.
Mark Gorenberg: We raised $300,000 with the candidate on the speakerphone. That, to all of us, was a revelation of how many people really wanted to get involved.
John Roos: That now looks like peanuts—we later did over $8 million at one event in San Francisco—but I remember Barack saying at the time, “Boy, you raised $300,000. That’s pretty good.”
Peter Greenberger, advertising executive, Google: Another thing that impressed us about Obama: He had a very skilled team. He hired several search-optimization experts, which is rare.
Mark Gorenberg: Chris Hughes, who was one of the founders of Facebook, left the Bay Area to go work in Chicago just after Obama announced.
Joe Garofoli: That guy’s 25 years old. He’s a genius.
Mark Gorenberg: Obama’s friend Julius Genachowski had a huge influence. He was a law classmate of Obama’s at Harvard, worked at a bunch of major tech companies, and galvanized people around the country to make sure the campaign had tech and businesspeople involved, regardless of their ideological beliefs.
Nick Thompson, senior editor, Wired: We had a Wired get-together, and one friend came up and said, “You know, I shouldn’t tell you this, but I’m about to go work as CTO for the Obama campaign,” and I thought, “Great.” Then another friend comes up and says, “Hey, I’m about to go work as CTO for the Obama campaign.” If all these friends of Wired wanted to go work for this campaign, he was clearly doing something good.
Thomas Gensemer, managing partner, Blue State Digital: Ten days before Obama’s official announcement, we got hired to do My.BarackObama.com. I had been with Dean in 2004. The campaign’s idea from the start was to allow traditional community organizing to scale nationwide. So with MyBO, we took a hyperlocalized effort—much like door-to-door community organizing—and supercharged it.
Tim Dickinson: Obama came in and said, “If this works for Facebook, why wouldn’t it work for us? This is a powerful thing. Why is the political world operating like it’s still 1998?”
Mark Gorenberg: A lot of the Valley’s newest technologies were being brought to My.BarackObama.
Steve Spinner: I thought it was absolutely brilliant to not have the website be all about “donate, donate, donate.” It was about “If you’d like to read policy, here are all these incredibly robust policies; if you want to make phone calls, make a call; if you want to canvass, go canvass; if you want to go see Barack or Michelle speak, here’s where to go; if you want to hold a house party, here’s how.” It was so inviting for people to play their own role—here were all the tools you needed to do it in a very successful manner.
Thomas Gensemer: From the first day, the traffic of people who expressed an interest in owning a piece of the campaign—either through giving, volunteering, or creating their own network—was huge. So any naysayers were convinced pretty quickly that the website was going to be the centerpiece of the campaign, especially if we kept investing in more tools, making things more localized, having it play a role in every field office and state office and state strategy.
Andy Rappaport: Usually, we look at political campaigns and say, “My god, they’re so primitive,” or, “They just don’t get it.” But none of us could have come up with a better way to use technology than Obama did.
John Roos: By mid-2007, the ideas from the startup community were coming from everywhere. Cleantech for Obama and Entrepreneurs for Obama both sprang up here and went national.
Steve Spinner: In May, about 120 of us had an Entrepreneurs for Obama video teleconference with Barack. Afterward, Steve Westly and some other senior Silicon Valley executives stayed and put forth their ideas on tech issues and initiatives and the campaign. I really loved that I could help differentiate this campaign’s technology from any other’s in history. I knew most of the venture capitalists and entrepreneurs, and if there was something good, I could bubble it up to the campaign. My personal favorite was the relationship we forged with LinkedIn.
Mark Gorenberg: My.BarackObama started to mirror what was happening on the general web.
Tony West: The Chicago headquarters was unlike that of any campaign I’d ever seen. It was so quiet—mostly young people on their own laptops. It had that very familiar hum of people just typing, like a startup you’d see in Silicon Valley.
Tim Dickinson: There was a foresight and deter­mination and seriousness about it. It was that progression we’ve seen in the tech world where the proof of concept happens—that was the Dean campaign—and then someone else swoops in with the killer app.
Andy Rappaport: It was like Lotus to the Dean campaign’s VisiCalc. Wait, I’m showing my age a little bit. I’ll give you a more contemporary example: It was like Google to the Dean campaign’s Infoseek.
Tom Rosenstiel, director, the Project for Excellence in Journalism: When the political establishment is trying to figure out early on whether someone is a serious candidate, one proxy is, how robust and sophisticated is the website? Another is fundraising, where the mainstream press says, “Barack Obama, he’s not showing up in any polls yet, but look at all the money he’s raised.”
Mark Gorenberg: From a fundraising point of view, we knew right away. Obama nearly caught up to Hillary in the first quarter of 2007.
Tony West: A lot of these fundraisers weren’t sanctioned events. People were spontaneously using the online tools to organize their own.
Peter Leyden: I went down to South Carolina for the first YouTube debate in July 2007. Everybody in the traditional press was saying Hillary was anointed, she was a steamroller, there was no way you could beat her. Obama was flatlining in the polls. But I told the Washington Post guy, Jose Antonio Vargas, “No way this is over. No one has any idea how powerful this fundraising and other stuff’s going to be.” Then I made a rash prediction: Obama would probably beat her and then win the presidency.
Tim Dickinson: The funding problem was finally being solved. Instead of having to rely on the party establishment and their friends—the Barbra Streisand circuit in Hollywood, the Susie Tompkins Buell types here—there was now a different way for a more democratic Democratic Party to assemble itself and mount its own campaign, to be self-funded and to free the party from the special interests.
Peter Leyden: Obama went to Google in November 2007 and gave an amazing speech about the centrality of technology not just in his campaign, but in his vision of what to do with the country. That was a huge moment, to see that this guy was really going to swing for the fences. This unlocked another big surge of support here.
Andy Rappaport: I see business plans all the time that are well written and well reasoned, but the business never develops until the market instructs, “OK, here’s your opportunity.” Obama started out with pretty good underpinnings, but what made the difference is that the public got to know him. The tipping point was the candidate himself—this is the guy that we’ve been waiting for.
Molly Kawahata, national high school codirector, Students for Barack Obama: I joined the campaign because Obama represented a progression from the pundits and party politics, and I saw that come to life in Iowa. It was freezing outside—at least, it was for me, because I’m from Palo Alto—and among those lining up and caucusing for Obama were Republicans. That was inspiring. We were all just Americans coming together.
John Roos: Walking the streets of Iowa, the energy for Obama was just amazing. That was the first validation that we had moved from the startup stage. This had the potential to really take off and be something big.
Steve Spinner: I couldn’t stop crying for three days after Iowa.