By Julia Ioffe, contributor

Ashton Kutcher was not prepared for this. When he arrived with a U.S. State Department technology delegation last week, he expected the screaming teenage girls, the journalists fighting for interviews, heck, he even expected the cold. But sitting with a group of Russian technology executives on Sunday night, the Punk’d star let loose. “When you get into a room without the Russian government controlling the room, the room becomes so vibrant!” he said. “We’ve had to fight to get people to talk openly.”

Kutcher was here, along with a handful of high profile tech execs — eBay (EBAY) CEO John Donahoe (who just launched a Russian version of the site), Cisco (CSCO) CTO Padmasree Warrior, Mozilla Foundation head Mitchell Baker, Twitter co-founder Jack Dorsey, and venture capitalist Esther Dyson — as part of a week-long diplomatic trip to get start ups, students, NGOs and even Kremlin advisors to exchange ideas on the wider uses of social networking technology. In one week, the group set out to help their Russian counterparts figure out new uses for social media, open source browsers, and online garage sales that can help modernize an economy, build a stronger civil society, and help President Dmitry Medvedev with his plans to build a Russian Silicon Valley near Moscow.

Instead, the techies, business people (and a movie star), discovered that sunny Silicon Valley-style optimism and the belief that knowledge conquers all, is a hard brand to franchise in Russia.

The Kremlin is in the midst of a much-publicized innovation push: Its top brass traveled to MIT recently to ask scientists how to build up Russia’s innovation economy. But, as chief strategist Vladislav Surkov recently made clear in an interview with a Russian newspaper, modernization will be “authoritarian modernization.” That is, it will have a distinctly Russian flavor, and it would bring none of the political reforms that would create the kind of breathing space so crucial to Silicon Valley.

So what would it bring? Well, beer pong, which Howcast CEO Jason Liebman taught to high schoolers in Novosibirsk. And altered expectations. “My image of ‘being in Siberia’ is forever changed by this trip … this place has real potential,” tweeted eBay CEO John Donahoe, who had just been cajoled by fellow delegate and Twitter co-founder Jack Dorsey into starting his own Twitter account.

Such connection-building and knowledge-sharing with Russian counterparts are all part of Secretary of State Hillary Clinton’s hazily defined notion of 21st-century statecraft, according to Jared Cohen, a member of Clinton’s planning staff who put together this trip and others like it. (Cohen described the trip in a tweet as: “facilitating peeps-2-peeps”). And when the delegation met with Surkov and Arkady Dvorkovich, another Kremlin advisor on modernization, they talked excitedly about e-governance and transparency. “By no means are we perfect on these issues, and there was no posturing, or lecturing, or badgering of any kind,” White House CTO Aneesh Chopra told me. “Russia is not an aid project,” Cohen says. Instead, this was one more push of the reset button.

But the delegates quickly discovered that Russia’s famous technological talent often finds few outlets at home. Because of the twin heritage of the Soviet criminalization of independent commercial activity and the brazen plunder of the 1990s, businessmen are reviled to this day and entrepreneurship isn’t mythologized in Russia as it is in the United States.

So when Shervin Pishevar, CEO of Social Gaming Networks, asked a group of high schoolers in Novosibirsk how many of them wanted to start businesses, very few hands went up. “It’s as if they thought it was impossible,” he says. And because Russian society has traditionally been very atomized, the strong mentorship community of Silicon Valley is missing, too.

Social atomization – and, consequently, a cementing of old mentalities — was something the group struggled with so frequently as to make it cliché. At the Sunday night meeting with Russian tech leaders, Cohen and Kutcher were baffled to hear that the tech companies had never sat down with Russian NGOs – most of them antediluvian operations – to explain what technological tools were available to them. The problem was lost in translation: Cohen and Kutcher were there to help Russians build a civil society, while everything in Russia was designed to break it down. The Russian techies in the room instantly protested that sitting down with NGOs would compromise the neutrality of their technologies, a banner behind which they hide from the ever-encroaching hand of the state.

And, by the end of the trip, the delegates who had not yet done business in Russia ran up against the full reality of the state of corruption in Russia — a recent study showed that one in three Russians had paid bribes, totaling as much as $318 billion annually, and Transparency International ranked the country 146th out of 180 in its corruption ranking — in their last meeting of the trip, with anti-corruption NGOs. The corruption fighters painted a grim picture of bribe-taking, wanton arrests, and intimidation. Kutcher, who had been broadcasting the panel live from his iPhone, was apparently not expecting such darkness. As he shut off the live stream, you could hear him groan, “That was the most brutal meeting…”

Esther Dyson, who has been a prolific investor in Russia for a decade, was one of the few not surprised, though she says she tried to let the more optimistic delegates form their own views. “They kept saying I was so negative. But I’m as idealistic as anyone. I’m just realistic about the challenges,” she told me. (“You have to be an optimist to keep investing here for 20 years,” she added.)

As a final illustration of Russian reality, the group went from the horror show of the anti-corruption meeting to a lavish farewell dinner sponsored by Digital Sky Technologies, an investor in Facebook and Zynga, which is widely believed to have close ties to the Kremlin. Everyone sat at different tables and, for the first time the whole trip, there was no substantive discussion.

“Well,” says Dyson, hesitating. “The fish was delicious.”