New York: The comedian Samantha Bee kicked off the new season of her TBS show, Full Frontal With Samantha Bee, last week by introducing a smartphone trivia app designed to spark voter registration. Bee copped to being a tech novice, and laid out her insecurities about her first product launch in a media preview. “We don’t have a clue if it’s going to succeed or fail," she admitted from the stage.

Sure enough, Bee’s app—This is Not a Game: The Game—crashed almost immediately, and was broken for days. It’s back online, and so declaring it a failure for Bee is premature. But it sure didn’t reflect well on Win The Future, the group that developed the game for her.

This isn’t the first setback for Win The Future, which also goes by the unfortunate acronym WTF. The group, founded last July, was the brainchild of Zynga founder Mark Pincus, who initially described it as “a new movement and force within the Democratic Party, which can act like its own virtual party." WTF set out on a series of tech-themed political experiments to engage disaffected populations by crowdsourcing policy ideas on Twitter. At one point, Pincus considered fielding a primary challenger to run against US House minority leader Nancy Pelosi. Now the group’s sole project is Bee’s app. Even if WTF can overcome its technical issues, it seems like quite a comedown if the sum total of its output for the 2018 midterms is a civically minded clone of last year’s hottest smartphone app.

WTF’s path echoes a dynamic that has played out repeatedly when the technology industry gets into politics. People who have made fortunes in Silicon Valley periodically create tech products aimed at civic engagement, confident they can maximize their impact by leveraging their technological skills and theories of disruption. Most have had no long term impact.

Sean Parker, the former president of Facebook, has spent years trying to build civic tech, most recently with an app called Brigade, which he launched in 2014. The app, intended to be a kind of social network to spark political activity, has never been one of the top 1,300 iPhone apps in the US, according to research firm App Annie. Last fall, Parker acknowledged that there probably wasn’t going to be a Facebook for democracy. “We have got to get this online group forming behaviour to translate into the offline world," he said at a panel discussion at New York University.

Sam Altman, president of the prominent tech incubator Y Combinator, raised money in 2016 for VotePlz, a non-profit with aspirations to become the TurboTax of voter engagement. It dove into software development and policy analysis, and was one of several groups to mention the idea of subsidizing ride-hailing trips to the polls. The group’s impact was unclear, but its founders apparently didn’t think it was effective enough to keep going. It shut down soon after the election. Altman headed out on a national tour where he interviewed Trump voters to find out what made them tick.

The election of Donald Trump as US president led to an unusually large wave of political activity from liberal-leaning Silicon Valley. Technologists set out to aid the Democratic Party, or build products that would address what they perceived as the problems in national politics, with varying levels of partisanship and success. Grassroots organizations like Indivisible and Swing Left have used tech-inspired organising tactics and risen in stature.

Other people dabbled, then drifted back to their startups. Jesse Pickard, the chief executive officer of San Francisco-based startup Elevate, helped organize a series of hackathons to develop civically minded tech tools in the wake of the 2016 election. By this summer, he said it had run its course, and knew of no active projects that had come of it. “There is always going to be this natural wave, then it will die down and only the hardcore people will be there at the end of the day," he said, adding that he is no longer involved in any political tech projects himself. “I run a company," he said.

Many people already in politics saw the newcomers as clueless and arrogant. “Enthusiasm lacking expertise isn’t going to get us a lot," said Debra Cleaver, founder and CEO of She voiced a common refrain that the time since the last election has been largely wasted. “It’s been two years, there’s nothing new, and there isn’t much new funding for technology," said Cleaver. She said the money could have been better spent on projects run by long-standing groups.

People familiar with the disconnect between the tech set and the political class find fault both with Silicon Valley’s techno-utopianism and Washington’s insular culture. Entrepreneurs have remained naive about the specific challenges of political activity, often building products that serve no real purpose. When they try to build tech specifically for political campaigns, they complain that it’s hard for Democratic candidates to strike out beyond insiders. The Democratic National Committee has attempted to address such critiques by rebuilding its tech operations. “We have made it our priority to introduce new players into the Democratic ecosystem,’ said Raffi Krikorian, the Democratic National Committee’s chief technology officer.

Both dynamics undermined WTF’s effectiveness. The group’s launch was “archetypical of the tech saviour syndrome," said Julie Menter, managing director of New Media Ventures, an investment firm focused on civic technologies, in an interview with Bloomberg. Others were less kind. WTF was subjected to a brutal round of ridicule in liberal political circles and the tech press, and the group almost immediately retreated from public view.

WTF’s most direct political activity was its work for Donte Tanner, a candidate for the Virginia House of Delegates last fall. WTF identified Tanner as someone who could benefit from a modest amount of targeted support, and attempted to rally college students to his cause by creating memes and trying to get him trending on Twitter. Tanner lost in a race that was decided by about 100 votes.

“That was pretty frustrating," said Adam Werbach, a co-founder of WTF and the former president of the Sierra Club. Werbach said Tanner’s campaign was hampered by the local Democratic party’s requirements to spend money on a direct mail campaigns run by party-affiliated vendors, when cheap digital ads would have had bigger impact. “It’s what the corruption of mediocrity looks like in the Democratic Party," he said. “It seemed obvious pretty quickly that the gap was not technology, which I think we can bring, but the political ability to sell that within the Democratic Party." Tanner’s campaign manager didn’t respond to interview requests.

It’s tempting to look at Brigade’s lack of impact and WTF’s wandering in the wilderness and conclude that their founders would get more political mileage out of their personal fortunes by cutting checks for civic tech groups. It’s no secret that such groups are always scrambling for money. Pincus doesn’t want to hear this. “I don’t think the biggest contribution I can make is just to pass out my dollars passively. I have more to offer than that," he said. “People can agree, or not."

In its work with Bee, WTF has reverted to the specific skill that Pincus can lay the greatest claim to: game design. Bee’s staff reached out to WTF earlier this year, and begun spitballing how best to design a game to encourage political participation. The end result was basically a clone of HQ, a quiz show where contestants compete for daily prizes by answering a series of 10 questions in real time. TBS, the network that airs Bee’s show, offers up a nightly prize of $5,000.

The dose of political engagement is intentionally kept low. As host, Bee asks questions that are politically flavoured, even if they’re not really about the subject. (Sample clue: If politicians were literally spineless, they’d have none of these tiny bones in the spinal column.) Players can earn extra lives by doing things like signing up for election reminders on through Bee’s app. On Wednesday night, about 15,000 people participated. Werbach said that lots of people have signed up for voting reminders, but declined to provide specific numbers.

For Pincus, the backlash to WTF still stings. He feels like potential allies in the political sphere rejected a chance to work together. “Nobody from that world tried to reach out and engage with us," he said. To him, the story of the last year not one of his group reigning in its ambition, but of it going out into the world and finding its place. “In retrospect, I agree we would have done better finding a narrower spot, I just don’t know we would have found the narrower niche on day one," he said. “We had to go through all this to get here."