One of America’s key voting rights groups plunged into chaos when it was needed most

People in face masks wait in line to vote in Wisconsin.

As the long lines in Wisconsin this month show, the need to make voting-by-mail easy has never been more important. | Kamil Krzaczynski/AFP via Getty Images

Inside the bitter war between Silicon Valley celebrities and Vote.org that could spell trouble in November.

A voting rights group called Vote.org seems like precisely the type of nonprofit that should thrive in 2020, with fans from Barack Obama to Taylor Swift and a URL that can’t be beat.

Its efforts to expand vote-by-mail — during an election year when more Americans are likely to do exactly that than ever before — should only make it more essential.

But the organization, which has established itself as one of the country’s most important civic engagement groups thanks to its research on how to turn out voters with absentee ballots and for its work to help defeat Alabama’s Roy Moore in 2017, has been derailed in recent months by an ugly internal drama featuring several of Silicon Valley’s most powerful personalities.

Last summer, Vote.org’s board fired founder Debra Cleaver and replaced her with one of the board members that ousted her. That presaged a bitter months-long war between Cleaver’s donors and her former board, and in its aftermath, at least three of Vote.org’s potential partnerships crumbled, millions in expected contributions fell through, and a series of embarrassing missteps tarnished the nonprofit’s brand.

Recode’s interviews with more than two dozen people, including Vote.org’s major donors, partners, and former board members and employees, along with two legal complaints submitted to the California attorney general, paint a portrait of a nonprofit that has been arrested in development. And it couldn’t have come at a worse time: Now that the coronavirus pandemic is likely to stress test the American election system — with voters waiting in five-hour lines in Wisconsin during the pandemic this month, for instance — the work of organizations like Vote.org, which says it “plans to turn out more than 5 million low-propensity voters” in 2020, is more important than ever.

If Vote.org were a public company, the shareholders would have voted the board out — and it wouldn’t have been close,” said Adam Goldstein, a past Vote.org donor who canceled a $1 million pledge to the group that had been in his will.

As you’d expect with an acrimonious split, both sides in the fight are pointing fingers. Defenders of the board told Recode that the fallout is Cleaver’s fault and that she poisoned the well with donors, caused havoc by refusing to leave her post quietly, and trash-talked the group to its partners so they cut ties.

Vote.org declined to comment on any specific reporting that Recode presented. Instead, it pointed Recode to data, such as that it had registered 550,000 new voters in 2020 and had helped about 500,000 voters request an absentee ballot. It also noted that it had created a website with resources on how to vote during the pandemic.

But no matter who is to blame, the mess has been crippling Vote.org and its ability to execute its mission. No one interviewed for this story, even those close to the board, thinks the nonprofit has fully recovered from the chaos. And experts worry that the saga could stifle efforts to make voting easier for people during an unprecedented election and pandemic. For all the rancor that has divided Cleaver and her former board, everyone on all sides could agree on this: A weaker Vote.org is bad for American elections.

“Startups and board drama are nothing new,” Sam Altman, the former head of Y Combinator, who has been among the Silicon Valley celebrities trying to outfox the board over the last year, told Recode. “But it’s a real shame when it sets back democracy.”

How democracy was set back

After Vote.org’s board voted to fire Cleaver last summer, the organization suffered what one donor called an “organizational shock” that negatively impacted its partnerships, its bank account, and its brand.

Cleaver had used her cult of personality to found a clearinghouse for absentee ballot information in 2008 that would become Vote.org. Her success depended on everyone from her former college classmates to fellow activists from her decade in the voting rights trenches. But if you live by a cult of personality, you die by a cult of personality — and when Cleaver left, many partners and donors did, too.

“It’s a shame because what we’re seeing right now is total chaos. And these two vectors in American life — of the pandemic, and our really high liability that we can’t run elections — those two things are colliding in a way that no one is ready for,” Dan McSwain, a political operative and a former board member at Vote.org who left as Cleaver crafted an all-female board, told Recode. “It’s a shame that an organization with so much momentum behind it seems to have spent a year of its life wading through something that, as far as I can tell, seems self-inflicted.”

Vote.org’s first withdrawn partnership was one Cleaver had planned with MTV’s parent company ViacomCBS, which would’ve included billboards in Times Square advertising her group, along with hosting a new youth-focused voter registration push called +1 The Vote. Cleaver had a personal relationship with the head of Viacom’s election programming; immediately after her ouster, Viacom pulled out of the not-yet-finalized deal and instead struck a similar agreement with a Vote.org rival, TurboVote, according to people with knowledge of the matter.

And two other high-profile groups that Vote.org had worked with in recent cycles to turn out low-propensity voters, the Voter Participation Center and the League of Conservation Voters Education Fund, are no longer currently planning to sign up to work with Vote.org on voter-turnout projects after Cleaver’s departure, according to people familiar with the matter.

Board defenders downplayed these losses to Recode, saying that while they lost Cleaver’s network, other partnerships are now more possible without Cleaver, such as recently announced ones with the NAACP Youth and College Division and the Transformative Justice Coalition.

But the Voter Participation Center and the League of Conservation Voters Education Fund were historically among Vote.org’s most important partners and were key parts of its celebrated research program. Research accounted for about half of Vote.org’s total spending in 2017, the most recent year of available tax records. That year, the Voter Participation Center and Vote.org ran an experiment in Alabama to assess how text messages and mailers together could turn out black voters. The next year, in 2018, the League of Conservation Voters spent over $1 million through Vote.org to send 18 million texts to young voters and people of color.

While Vote.org still occupies a prized URL that registers already-likely voters who intentionally seek information about elections, critics say it no longer appears to be prioritizing the grunt work of researching and activating unlikely voters.

For instance, despite the nonprofit’s plans to use the 2020 primary season to test the effectiveness of various get-out-the-vote strategies, such as using texting to encourage voting-by-mail, Vote.org did not end up performing any research on ways to engage these low-propensity voters during the primaries this spring, according to people familiar with the matter. The group’s longtime research head, a college friend of Cleaver, stopped working with Vote.org after Cleaver’s firing. The group just didn’t have the money to do that expensive research, people close to it said.

That’s another way Vote.org suffered after Cleaver left: financially. Multiple political advisers to major Silicon Valley donors told Recode that Vote.org has suffered serious reputational damage and that they are recommending their clients give money elsewhere. Several of Vote.org’s former major supporters, including LinkedIn founder Reid Hoffman, venture capitalist Ron Conway, and Altman, are no longer advising their networks to support the organization, sources say. And in a letter in September that urged Vote.org’s board to reconsider Cleaver’s ouster, donors who claimed their donations and pledges accounted for 60 percent of the group’s funding warned that they would no longer back Vote.org if she wasn’t reinstated.


Drew Angerer/Getty Images
Sam Altman was among the Silicon Valley celebrities that Cleaver consulted as tensions boiled with Vote.org.

“Vote.org was the Silicon Valley group,” said one person close to the nonprofit, who sees errors on all sides. “When you’ve pissed off all the Silicon Valley donors with the way you handled the transition … you lose your Silicon Valley base of funders. I think they can stay stable, but they can’t run the scale of the program that she had planned.”

The group had about $2 million remaining in the bank at the end of 2019, according to a person briefed on the figures, which is $1 million less than what tax records show it had on hand at the end of 2017. Vote.org’s new CEO, Andrea Hailey, was telling people late last year that it was operating on a shoestring budget, although its board members are now said to be personally financing the nonprofit more.

Some people close to the board concede that the group has lost its base of Silicon Valley donors, but they say it is focusing on grassroots donors and that Cleaver’s ouster has improved relations with more traditional funders, like foundations: “One door closed, and another opened,” one person said. (No major gifts have been announced publicly.)

But perhaps the most important consequences have been a series of missteps in Vote.org’s public-facing work that have harmed its most critical asset: its reputation. Text messages sent to voters in Wisconsin this month made no mention of the explosive voting rights fight waging during the coronavirus and encouraged them to vote on Election Day. That angered some Wisconsin leaders who were seeking to delay voting altogether, Recode is told.

And then there was a high-profile screw-up in which Vote.org advertised the wrong date for Election Day on 16 billboards in parts of Mississippi with large black populations last November, a gaffe that angered its principal partner in the state and triggered a round of damaging headlines.

The error on the billboards wasn’t entirely Vote.org’s fault, but a vendor’s. Nevertheless, it was deeply embarrassing for the organization, and some people believe it wouldn’t have unfolded the same way with Cleaver.

“We understood the mistake to be a mistake with no malicious intent to confuse our voters. However, the backwash and reality of all this is that folks were still confused and there was never any formal apology made to the communities most impacted by the mistake,” Arekia Bennett, the head of Mississippi Votes, Vote.org’s partner, told Recode. “MS Votes reached out for a debrief post-election and never got one. Recently Vote.org has reached out, but we are wary and not sure how or if we want to engage.”

There’s also been an impact on the reputation that’s inherent to losing Cleaver, who is a minor icon in civic circles and has been inextricably linked to Vote.org for a decade, for better or worse. So one of the biggest concerns that even relatively neutral observers voiced is that the brand of Vote.org has been damaged by her firing, which has been widely gossiped about in voter-registration circles.

Some of this brand damage is due, no doubt, to Cleaver herself, who has been more than willing to tell everyone from billionaires to her Facebook friends about her ouster, such as when she bashed them for cutting off her health insurance and telling her Facebook audience that she had “one hell of a story coming.” Critics say that Cleaver’s grudge against the place and people that fired her has harmed the movement. The incentive is there: Cleaver’s new organization, VoteAmerica, is a direct competitor to Vote.org.

“For everyone who called, I told them faithfully what happened. But these people are free to make their own decisions,” Cleaver told Recode. “They fired me in retaliation and still expected nothing but the utmost discretion. And I have a professional reputation as well.”

Even defenders of the board privately concede that it mishandled public communication about Cleaver’s exit. Cleaver had also been able to shape the narrative because Vote.org had said next to nothing publicly or even privately to its supporters about what happened.

What happened at Vote.org

Vote.org’s board, which Cleaver had recruited over the prior two years, had generally given its CEO a long leash, like most volunteer boards do. But things began to sour at the start of 2019 as the board began to scrutinize Cleaver’s performance, according to people close to the board. They felt that she wasn’t prioritizing fundraising enough, and that she was hamstringing the organization’s growth by not hiring a chief operating officer. They were also growing concerned about reports of how Cleaver treated her employees, which ended up being the catalyst for the accusations and counter-accusations that led to her boardroom firing — and eventually, to a number of key donors pulling their support.

The snowballing began when an employee who clashed with Cleaver voluntarily resigned in May, but the board awarded him a $40,000 severance payment anyway. Cleaver alleged this move violated the law, leading her to ask the board to resign.

Just before she was fired that August, Cleaver even tried to leverage a potential donation, convincing a donor named Sage Weil to pledge $4 million to Vote.org, which would have been the biggest gift ever to the nonprofit — but it was conditional on her remaining the group’s CEO.

“It had never occurred to me that Vote.org could exist without Debra,” Weil told Recode.

But the board wouldn’t relent. It zeroed in on reports, including some that came in unsolicited over LinkedIn’s InMail, that Cleaver, described by even her allies as bulldozing and brawling, could be a harsh and volatile boss. Some former employees told Recode that she presided over a culture that could border on “bullying” and “toxic,” descriptions that Cleaver and her supporters say are sharply gendered.

Cleaver had a tendency to bombard employees with blunt messages on Slack, especially late at night, former employees say. Former employees also say that she was quick to disparage her own colleagues and partners behind their backs, often calling them “idiots.”

“Am I a demanding boss who pays well and expects excellent work product? Yes,” Cleaver told Recode. “We weren’t running a fruit stand. We were running nationwide voter-registration and get-out-the-vote drives in a country with a fragile and crumbling democracy.”

Despite these complaints, the board never conducted an independent investigation or placed her on a performance-improvement plan. They did ask her to take a sabbatical and assigned her an executive coach, but board defenders feel that she didn’t engage seriously. They officially fired Cleaver in August.

Cleaver believes that her firing had nothing to do with her performance, but that the board retaliated against her as a “whistleblower” after she confronted them about the severance payment.

Tempers got hotter, not colder, when they terminated her. Key partners and donors to Vote.org, including Hoffman, were blindsided when they received a mass email blast that August saying that Cleaver was out. They would spend the fall fighting bitterly with the board to return her to her role.

Over the next few weeks, donors led by Goldstein, the young entrepreneur who had planned, in the distant future, to leave $1 million to Vote.org in his will, began demanding that the board reinstate Cleaver, or to at least explain why they fired her. Goldstein organized a coalition of wealthy backers that included some of Silicon Valley’s marquee names like Altman, who altogether claimed they were responsible for 60 percent of all the money raised by or pledged to the nonprofit.

“Today Vote.org appears to lack leadership and strategy. Vote.org seems to be losing funders, key partners, and essential consultants, and there is a risk of the remaining full-time employees resigning,” the donors wrote the board in a formal letter around Labor Day. “Vote.org’s future is uncertain.”


Kelly Sullivan/Getty Images for LinkedIn
Reid Hoffman, one of the country’s biggest political donors, tried to broker a truce between Cleaver and Vote.org.

They prepared to go public with their complaints that fall, but at the last minute, Hoffman’s team — Hoffman conspicuously had not signed Goldstein’s letter — intervened. An operative who worked for him, Tamer Mokhtar, who declined to comment, embarked on a last-ditch mission to try to broker a truce. He flew to Los Angeles, without the other donors’ knowledge, and floated a compromise to the board, but the talks fell apart.

The donors didn’t end up going public, but now Hoffman, its biggest donor to the tune of $3.8 million, is no longer currently planning to fund Vote.org going forward. Hoffman prides himself on only backing founders.

The best- and worst-case scenarios for democracy

So where does this leave Vote.org? The best-case scenario for democracy is that Cleaver and Vote.org manage to build two distinct, successful organizations, creating a redundancy in the voter-turnout universe that experts say isn’t always a bad thing. There are already a half-dozen other groups doing this work, such as Rock the Vote, and there’s been booming donor demand in this space since 2016.

“It may well be that Debra does her thing and [Vote.org] does theirs, and combined they are about as effective as [Vote.org] was in the past,” Donald Green, a political scientist who is unaffiliated with the group but pays close attention to it, told Recode.

The worst-case scenario? That the iciness between the two teams creates factions in the generally cozy voter-engagement world that makes working together impossible. Or that the runup to the 2020 election resembles the runup to the 2019 election, when some employees felt that Vote.org was rudderless, partially because they had to deal with Cleaver’s antics after she left. The complaints submitted by Cleaver and a major donor to the California attorney general show that she has no intention of burying the hatchet.

Another troubling possible outcome is that Vote.org might struggle to rebuild its donor base and may no longer afford to execute its same work. To this day, many donors remain frustrated that they have not been told why Cleaver was fired — the only public comment came on a little-noticed podcast where the new CEO said she was terminated due to “differences in opinion” — which could leave the organization underfunded for 2020. Its two biggest donors, Hoffman and Weil, are now considering funding Cleaver’s new nonprofit, which is doing similar work and has raised $4 million.

“The danger in this type of setting is whether she takes all the funders with her,” said David Nickerson, who ran the experiments department of the Obama reelection campaign.

But neither Cleaver nor Vote.org can rebuild overnight. And with six months to Election Day, the clock is ticking.


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