The Trump Resistance Will Be Incubated

At the ripe “old” age of 38 with a pair of toddlers and more than a decade into a career as a public defender, Rita Bosworth doesn’t conform to the stereotypes of a Silicon Valley startup founder or a slick Beltway operative experienced in the ways of manipulating American politics.

“I never ever planned to, wanted to, or felt that I would be any type of entrepreneur,” she recently admitted to me over the phone. “I’m an attorney, and I like doing it. It’s not even a space I’ve ever worked in.”

Yet seven-and-a-half months after Donald J. Trump’s shock election to become the ultimate leader of her country, Bosworth finds herself leading an ambitious (and some would say long shot) grassroots campaign to win back state legislatures—and thus national power—for Democrats. Bosworth is the executive director of Sister District, a tech-enabled political action committee. It’s one of the 14 projects that on Tuesday won $50,000 apiece from New Media Ventures, a Bay Area network of angel investors and clearinghouse that vets promising technology and progressive startups for philanthropic foundations and individuals. It’s the progressive, philanthropic version of Silicon Valley’s more famous commercial counterpart YCombinator in some ways, in its approach to risk, mentoring and investment. Unlike YCombinator, New Media Ventures is a nonprofit. It both invests in companies and provides grants.

Sister District’s Rita Bosworth (Photo: Colin Campbell)

The funding is a vote of confidence in Bosworth and her three other colleagues’ project. It’s also a chance for her team to learn from New Media Ventures’ portfolio of other tech, media and political startups (her three other full-time colleagues are also lawyers). New Media Ventures’ commitment to these 14 fledgling projects and their often unconventional leaders also means that the founders have passionate advocates hitting the phones, pounding the pavements, and schmoozing their way through fundraisers to persuade wealthy individuals and foundations that they’re worth follow-on grants and investments. For instance, both Sister District and Indivisible, another funding recipient, have already received a commitment for further funding from the Propel Capital Network, a philanthropic and impact investing fund in New York City.

New Media Ventures dubbed this financing its “Resist and Rebuild” round. That is, it wanted to fund startups that would help progressives “resist” the negative trends in the current political environment, and to bolster partisan and nonpartisan democratic infrastructure with the goal of lowering the boundaries and costs of running for office. They’ve pledged to invest a total of $1 million this year on new projects.

The network is jumping in to harness the political awakening among citizens that manifested itself after the presidential election, explained Julie Menter, the New Media Ventures principal who sifted through the 500 applications for the project financing—nearly double the number it received in its last call open call for projects. As one barometer of this awakening, political scientists estimate that between 3.2 and 5.2 million people participated in the Women’s March this January, making it the largest single-day demonstration in U.S. history.

“In the pre-election context, getting large groups of people to do stuff was really, really hard, and particularly getting a large group of people to do something about politics was really, really hard,” Menter said.

As Bosworth discovered, this is no longer true. In the few months since the 2016 election, Bosworth discovered that there are literally thousands of people—many of whom were not politically active before—who share her thoughts and goals. Twenty-one thousand people have signed up for the group’s emails. Bosworth estimates that Sister District has 25,000 volunteers spread out across all 50 states. And Erik Raser-Shramm, the campaign manager for Democratic Delaware State Senator Stephanie Hansen, attributed Hansen’s late February electoral victory to the help the campaign received from the surge in volunteers and money generated by Sister District and its partner grassroots group Flippable, another recipient of the $50,000 in seed funding from New Media Ventures.

Flippable, Indivisible, Sister District, Swing Left, and Townhall Project are all different political iterations of new groups that are capitalizing on local grassroots energy, started by individuals who saw how certain political processes could be improved upon.

“We have millions of people showing up for these marches, and you still have fairly low awareness of the underlying dynamics, and understanding of the way the system works, the underlying causes of the reasons for why we are in such an overwhelmingly Republican country,” Flippable CEO Catherine Vaughan told me over the phone. That’s despite Democrats winning more popular votes in presidential elections, and some House and Senate elections too.

Vaughan and her co-founders want to change this on two fronts: Using data to analyze and target attention and resources to the most winnable races in state legislatures across the country, and to create consumer-level communications channels to enable all those activated, not-usually political people to easily participate and engage in the wonky practice of supporting Democratic candidates in state legislatures other than their own.

“I think there’s a massive untapped potential for telling the story of gerrymandering,” Vaughan said. “We put out a video about gerrymandering 11 days ago and it’s already gotten 500,000 views.”

YouTube video

Flippable currently operates a website, but wants to build an app that “would combine convenience and customization,” said Vaughan. “You can see who we’re supporting, but if you are also interested in supporting women of color in the Midwest who care about the environment, you’d also be able to filter in those ways to find those candidates, and have an easy way to get updates and close the feedback loop with their campaign.”

Vaughan, who led Ohio’s out-of-state volunteer team for Hillary Clinton’s presidential campaign, said that she found that out-of-state volunteers want to know that the time that they spend campaigning is effective, which is one of the reasons why working on an accurate data model for winnable seats is so important. She also says that millennials like her want more information, context and engagement about the political process from campaigners, instead of patronizing boilerplate fundraising emails populated mostly by donate buttons.

To be sure, Democratic party officials are working on the problem as well. The Democratic Legislative Campaign Committee has launched a program dubbed “Advantage 2020” that aims to focus energy and resources on targeted, “winnable” races in state legislatures across the country.

But outside groups like Flippable and Sister District hope to enhance these efforts. Individuals with expertise in building consumer technology products, conducting marketing campaigns, and raising money in some of these groups hope to keep all those newly-energized grassroots supporters and protest marchers engaged for the long term.

Brady Kriss, the founder of Ragtag (Photo courtesy Brady Kriss)

New Media Ventures isn’t just funding new tech toolmakers or political ventures however. It has also funded a project that seeks to efficiently and effectively channel tech workers’ newfound desire to engage in the political process. That project is Ragtag in San Francisco, and is one of several groups that sprung up post-election to matchmake the interests and capabilities of activated technologists and developers to political and issue campaigns. The group then tasks individuals to manage and coordinate teams on assigned projects. Brady Kriss, a former Clinton campaign staffer, is the founder.

“They understand the problem really, really well from both sides,” Menter said. “How do you get someone who’s a technologist who wants to make a difference, and make sure they have a satisfying and rewarding experience, and how do you help campaigns work with volunteers who can do incredible things, but are sometimes flaky?”

Other New Media Ventures investments this time around also focus on technological tools. Amplify is a software tool and app created by developers in San Francisco for different chapters of Indivisible and other progressive groups. Notifica is a notification app and project of the non-profit United We Dream, a nonprofit that advocates on issues related to being an undocumented youth . The app, which acts as a kind of panic button, enables undocumented individuals of any age to preload instructions and information for families and friends, and then to send them all off with one tap in case immigration authorities suddenly show up to deport them. Vigilant is a tool that was created for Clinton’s presidential campaign. Clinton staffers used it to slash the time it takes to vet people before allowing them to join, donate, or speak for the campaign. New Media Ventures and Vigilant Founder Mike Phillips see a wider commercial user-universe for the product, such as journalists, speaker bureaus, and others. Voter Circle is a Bay Area, California commercial startup. It provides local political campaigns and candidates with a messaging tool that supporters can use to get out the vote among their friends. The company matches information on public voter rolls with individuals’ social networks and enables them to target eligible voters through email, and soon text messaging. Menter sees promise in the company because it has the potential to lower the cost of reaching voters, thus helping candidates with few financial resources into the election process. She argues that it won’t go the same way as the ill-fated Votizen, another social get-out-the-vote company (which relied on Facebook instead of email) because many campaigns have already used it successfully — including its co-founder Sangeeth Peruri. His team created the software to help his own local (successful) campaign to become Los Altos School Board Trustee.

Other projects are not as directly tied to the political process. Grant recipient Online SOS, for example, is a support network that was launched last August by San Franciscan Elizabeth Lee and New York area therapist Samantha Silverberg. The non-profit’s goal is to provide individuals with guidance on steps to take against digital harassment and professional mental health counseling. The co-founders have worked with with the major social media companies and they’re currently in discussions with those companies to explore scalable growth options. The group has also received financial commitments from the San Francisco tech nonprofit accelerator Fast Forward and the Craig Newmark Philanthropic Fund.

New Media Ventures’ investments reflect an approach that its staff argue is urgently needed in the world of philanthropy and impact investing.

Funders need to respond to the circumstances quickly, and be willing to take more risks (something that Micah Sifry, Civicist’s editor, eloquently and thoroughly argued recently).

“We’re coming in now and funding things quickly for an institution, but it’s still six months after the election. So if the grassroots hadn’t been there, none of this [infrastructure] would be here,” Menter said.

“If we’re just funding things that are proven, then we’re not actually going to be funding the change that we need to see because clearly the things that are proven haven’t brought the change we need to see,” said Menter. (See Menter’s keynote talk from this year’s Personal Democracy Forum for more.)

“My sense is that with these massive, long-term problems, if we only continue to support the same thing and expect a different result, we are wasting our time,” said Christie George, New Media Ventures’ executive director. “So one of the reasons that we encourage these small batches of experimentation is that we think there is an opportunity to get closer to solutions, and we think it could have a huge impact on the mission of a foundation.”

And it’s not as if entities such as New Media Ventures, the Fast Forward accelerator in San Francisco and other emerging funnels of finance are dispersing money indiscriminately like a tourist throwing seeds out to feed the pigeons in London’s Trafalgar Square

For example, New Media Ventures helps the organizations it funds to think through, and build sustainable revenue models at the same time that those groups push through with their missions. New Media Ventures published a guide for social entrepreneurs in 2016 with ideas and examples from its portfolio companies on how to develop sustainable business models other than just relying on funding from foundations.

One of its currently-funded projects, the social justice organizing network Mijente, for example, earns revenue by training other issue groups to organize campaigns effectively. That revenue stream complements the funding it receives from foundations and individuals.

At Fast Forward, applicants for the program need to meet some threshold criteria, such as originality of the proposed tech product, having at least some beta experience in the field, and an intimate familiarity with the end-user’s needs and demographics. Charismatic and articulate leaders who can attract capital are a must, as are solutions that can scale without much additional cost.

“We look for people with experience with the problem. It’s really important to us that it’s part of your lived experience because we think you’re going to solve the problem differently,” said Shannon Farley, the accelerator’s co-founder and executive director. “If it isn’t your lived experience, it may not have the same resonance.”

These measures attempt to bring some rigor to the process of vetting. Startups are inherently competing against more established impact organizations that can present deep pocketed donors with more extensive evidence of effectiveness, and proof that their donations will go a long way.

For now, organizations such as New Media Ventures and three-year-old Fast Forward have the testimonies of their more successful companies and projects to rely on. Will Rockafellow, the general manager of Daily Kos, for example, explains the impact and importance of a strategically-timed investment from New Media Ventures. The investment helped the media company navigate an unexpectedly rough period in 2012, and to manage the financially treacherous position of being a commercial company on a mission.

“I can honestly say that without NMV, Daily Kos would not exist in its current form—the largest partisan liberal media outlet in the country, with up to 20 million unique visitors in peak months,” Rockafellow wrote in an email to Civicist. “But it wasn’t just that they helped connect us to some incredible mission-driven investors. It was also that they didn’t blink over our for-profit legal structure. Most political givers refuse to consider anything that isn’t a nonprofit.” He continued: “Our legal status gives us incredible freedom to engage electorally, freedom that doesn’t exist in the c3 nonprofit worlds. Yet the second any such investor saw our legal status, they’d immediately refer us to their financial advisors. So not only were we evaluated by our mission and potential accomplishments, but also our return on investment. We just aren’t able to get the same return as a tech start-up as a partisan organization.”

“Christie George and NMV didn’t have such hang-ups, and they helped connect us to some great investors,” Rockafellow adds. “To this day, I know political for-profits continue to run into the same roadblocks we did, and so I’m glad that NMV continues to work to educate these investors that legal status shouldn’t prevent people from investing in the organizations and companies that are working to make this a better country.”

As Sifry and other journalists have documented, a plethora of established groups are vying for the wide-open purses of an increasing number of donors all over the country post election.

But the biggest fact hovering above these incumbent political organizations is the election of the United States’ current president. They were unable to convince those that voted for him that it was a bad idea, and they were unable to convince the millions of people who didn’t vote that their votes actually mattered.

Perhaps traditional metrics don’t apply, and it’s time to “Think Different.”

Sarah Lai Stirland is a freelance writer in the Bay Area. She can be reached at