Tech Loves Obama, and Obama Loves Tech: The Campaign Roundtables

Barack Obama is not known for being a schmoozer. In fact, he seems to have an aversion to kissing up to donors. But over the course of last year’s U.S. presidential campaign, he repeatedly made time for an unusual set of open-ended conversations with the technology industry.

At fundraisers with prices in the tens of thousands of dollars, Obama and his team met for roundtable discussions with small groups of tech entrepreneurs and investors.

Rather than the usual prepared opening remarks followed by handshakes and photo ops, the events were held at large tables, with each of 20 participants given time to address the issues of their choice.

(And then of course there were official photo ops, though attendees were asked to not humblebrag too hard on social media about meeting the president.)

It wasn’t cheap. Attendees paid $35,800, the legal maximum amount for campaign donations to the Obama campaign and the Democratic National Party.

But even at that price, putting just 20 people in a room isn’t the most efficient way to raise money.

“It wasn’t about the fundraising ROI for him,” said investor Chris Sacca of Lowercase Capital, who helped organize the dinners. “You’d do better if you were in a larger room high-fiving everyone.”

And Sacca argued that the fundraisers weren’t as elitist as they might have been. “Before these roundtables, President Obama had no forum to hear from tech guys who weren’t Eric Schmidt, Steve Jobs or John Doerr,” he said.

The roundtables were born from a partnership between longtime campaign organizer and Tech for Obama founder Jim Green — who has been working on Democratic campaigns for the past 16 years — with participants drawn from the networks of three politically active tech guys: Sacca, Salesforce CEO Marc Benioff and investor Shervin Pishevar.

“I’ve always wanted to create a forum for two-way conversations, but I’ve never found a campaign as willing to go there,” said Green. “And it just so happened it was the president in office, because Barack Obama enjoys talking to smart, thoughtful people.”

Some 140 total techies participated in the roundtables, with the first held in December 2011 in Washington, D.C., and the final held in October 2012 in San Francisco (others were in Oakland, Calif., and Chicago, Ill.).

But the roundtables were not set up as a series of eight events — rather, each was successful enough that Green was able to convince the Obama team to commit to do another.

“The president really enjoyed it, so he continued the dialogue,” said Pishevar.

Participants at the Obama roundtables included 140 different individuals, among them Sean Parker, Shawn Fanning, Troy Carter, Gary Vaynerchuk, Tom Katis, Jeremy Stoppleman, Tony Robbins, Geoff Ralston, Garrett Camp, Dave Morin, Ron Conway, Reid Hoffman, Jason Putorti, Kevin Lynch and Matt Mullenweg. (Indeed, a lot of dudes.)

All told, the series raised $6 million to $7 million, according to Green. That’s out of more than $1 billion raised for the Obama campaign altogether.

The events were never publicized, but they weren’t secret, so the organizers agreed to answer my general questions. The White House did not reply to requests for comment.

The most popular issues, said those who attended, included immigration reform, education and the red tape of government technology deals — along with some mentions of climate change, patent reform and regulatory constraints.

Face time with the president wasn’t a hard sell, said Pishevar — though Republicans do in fact exist in Silicon Valley. “There are some people in the venture space, especially the older-school guys, who were Romney people,” Pishevar noted.

The organizers said other techies who wanted to be involved but didn’t feel comfortable throwing down big bucks participated in more practical sessions without the president, including a visit to campaign headquarters in Chicago to talk best practices with members of the Obama messaging and policy team. And others got even more involved as in-house technologists on the campaign’s now-famous data operation.

Roundtable participant Geoff Ralston, a partner at Y Combinator, asked Obama a question about education, and said he came away more impressed with the president than he’d expected.

Prior to the roundtable, he felt largely ignored by national politics in a state that’s solidly blue. “Who comes to California, who gives a fuck? California’s done,” Ralston said. “We’re completely disenfranchised here. Just look at the TV, there’s no ads.”

After Obama talked to a range of other topics and answered his education question, and then came up to Ralston at the end of the event and asked how he did on that specific issue, Ralston was sold. “I don’t know that he was Clintonesque, but he was on the issues. He was good.”

So, now that Obama is reelected, can techies still expect him to come courting Silicon Valley every few months? Probably not, said the organizers, though Obama’s staff may maintain the relationships.

But the participants have their photos to cherish and their virtual shout-outs to imagine — as Obama tackles issues such as immigration — and perhaps they have a newfound sense of civic responsibility.