[obama chicago polling voting booth]REUTERS/Kevin Lamarque "Oh lord. I am nervous," reads the text message. "Come sit with me." Debra Cleaver is sitting a few rows behind me, squinting at a laptop perched across her knees, writing a speech that she is slated to give in roughly half an hour. The founder of Vote.org, a website that’s dedicated to increasing voter turnout, Cleaver is a quick-witted New Yorker whose friends describe her in superlatives — “larger than life”; “hilarious”; “genius.” She speaks with a mild Brooklyn accent (she was raised in Bensonhurst) and curses amply and often. Still, she’s breathing heavily as she shifts her backpack from the seat she’s been saving for me in the crowded NYU auditorium that’s hosting the annual Lesbians Who Tech conference. For Cleaver, a lot is riding on her performance at talks like this. She’s counting on ample charisma and an urgent mission to help her raise money in the remaining days before the election. Roughly a decade ago, Cleaver started thinking a lot about voter turnout, and why, in America, it remains so shockingly low. Since the early aughts, when Howard Dean and websites like MoveOn.org began using digital organizing tools to reach voters, the internet has offered a tantalizing promise to political campaigns: the option of targeting specific voters through email, Facebook, and Twitter, and then reaching out to the targeted clusters en masse. Several campaigns—most famously Barack Obama’s in 2008—have been successful at translating this kind of online support into donations, but few have figured out how to convert digital contacts into actual votes. Turnout has remained low, which most politicos attribute to a growing culture of apathy. As Steve Schale, a political operative who led and advised Obama’s Florida campaigns in 2008 and 2012 respectively, puts it, “You can’t data mine inspiration.” Not that Silicon Valley hasn’t leapt to try, this election in particular. In the battle between Donald Trump and Hillary Clinton, more than just party politics is at stake: A cluster of votes could be the difference between Trump accepting a concession and a several-year blowout over the presidency. And thus, this year has borne a slew of start-ups designed to kickstart civic engagement—from Sam Altman’s slang-savvy voting guide, VotePlz, to Brigade, a social network for politicos that allows its users to “pledge” (and encourage friends to pledge) to vote. But the techies who argue that fixing America’s flawed voting system should be as simple as shifting a Facebook algorithm to direct the correct message to the correct feed—well, Cleaver thinks they’re full of crap. Cleaver’s focus is the boring-but-necessary work of translating the arcane state-by-state voting rules into digestible, actionable information. In her opinion, most people do, in fact, want to vote, but they have a knowledge gap about how to do it. They don’t vote because it’s hard, and because the voting process has never been redesigned for the digital age. For Cleaver, technology is a tool to amplify and streamline; she tackles the issue as a user interface problem. So Vote.org aggregates all the state voting rules in one place. Then, the site helps you do as much as possible online — if you’re in a state that doesn’t allow online registration, she’ll mail you a ballot. For eight years, Cleaver ran Vote.org (which was previously named Long Distance Voter) as a side project from her day job as a product manager. Despite its humble origins—she built the original site herself and ran it single-handedly for years—it’s earned Cleaver a large reputation in political circles. Rock the Vote uses Cleaver’s absentee ballot tool. The organizers of Vote.gov, the official government-sanctioned voting website, count themselves as fans. Cleaver’s once-side project has been responsible for almost 600,000 registered voters in the last year. In the last six months, she’s gone bigger. Vote.org is now Cleaver’s full-time job. Though she still works primarily from the couch in her Alamo Square apartment in San Francisco, she now employs a small staff. And Vote.org was accepted into the summer 2016 session of Y Combinator, as one of the incubator’s few nonprofits. While there, Cleaver developed a plan—a plan that she has roughly six days left to fulfill—that she believes could radically increase the number of people that make it to the polls on November 8th, at a dirt-cheap price compared to what it costs other organizations to get people to vote. How is she going to do it? Text messages. [debra cleaver]REUTERS/Kevin LamarqueThe truth is, no one has figured out an easy way to get people who aren’t voting to vote. In the 2012 general election, 57 percent of eligible citizens made it to the polls, a drop from the 62.3 percent who voted in 2008. Regardless of small losses and gains every cycle, America lags behind its peers: in a 2016 study on voting, the US ranked 31 out of the 35 most developed democratic countries in the world in voter turnout. And since 2012, 14 states have passed restrictive voter ID laws, which threaten to chip away further at the number of citizens who are able to maneuver their way to the polls. The most effective way to increase voter turnout comes from the excruciatingly slow work of contacting people personally, traditionally through telephone calls and house visits. During Obama’s reelection campaign in 2012, Schale knew he’d have to expand the number of people who were voting to win Florida, so he sent volunteers to parts of the state that seemed friendly to Obama. “We went to bus stations and shopping malls and college campuses, and we went to coffee shops and barber shops in Hispanic communities,” he says. Then, once voters are registered, you have to make sure they make it to the polls. “We’d keep bugging them until they did,” says Schale. Complicating matters is the fact that American elections are not administered federally, so there are 51 different ways to register to vote — most of them not online. “You still have states in this country where you can’t register a form without printing it and mailing it and signing it,” says Ashley Spillane, the former president of Rock the Vote and chair of the Vote.org board. “Asking an 18-year-old to find a stamp when they do everything else online is difficult.” Bryan Whitaker, chief innovation officer at the political data company TargetSmart, puts it this way: “There’s this whole world of legal documents that has moved online successfully, for everything except this one thing.” Cleaver was in her twenties when she first became aware of the stakes of making the voting process easy. She had just graduated from Pomona and was living in Western Massachusetts during the 2000 contest between Al Gore and George W. Bush. When the polls came in showing a Gore victory, her liberal friends rejoiced and went to sleep. Cleaver stayed up, watching the returns come in. So she was alone in her living room, inches from the television, when Florida flipped from blue to red. Her friends awoke to a Bush presidency. For Cleaver, it was an awakening of how powerful a few votes could be. In 2004, Cleaver happened into a job investigating police misconduct for the City of New York. She spent her days asking police officers difficult questions and testifying in court. But on the side, she worked as an organizer. Cleaver volunteered with Swing the State, a nonprofit that organized volunteer canvassing trips to swing states. She volunteered so aggressively that, by the 2004 election, she was directing it. At the time, she found cold calling and door knocking — the tried and tested methods of campaign outreach — excruciating. It was time consuming and ineffective. Also, she hated the dogs. “They’re never friendly,” she tells me. “It’s never, like, a golden retriever.” There must be a better way to encourage people to hit the polls, Cleaver thought, but she shelved the idea. Democracy called on Cleaver to knock on doors, so she swallowed her discomfort and did just that. We all know what happens next: The 2004 election did not go the way Cleaver was hoping. (Bush, take two.) Politicos kept insisting that canvassing was the most effective tool, but she had her doubts. She found herself wondering if the problem had another angle. Two years later, she was a few drinks into a Netroots Nation conference in Las Vegas when she raised the subject with Jon Liroff, a colleague from her days investigating the NYPD. Cleaver was looking for low-hanging fruit: a group of people who were motivated to vote, but had an obstacle blocking them from casting a ballot. Liroff, having recently returned from a stint abroad, had an idea: “What about absentee voters?” The timing was perfect. By 2007 Cleaver had happened into a job as a product manager at MySpace, and was newly relocated in Los Angeles. She had no friends, so she taught herself Drupal and got to work building a site called Long Distance Voter. Cleaver and Liroff enlisted the help of their former colleagues; in off hours, they divvied up the states and set to work forming a repository of the rules for each state. It was more complicated than it seemed. It was Cleaver who figured out, for instance, that to register a vote in many states you had to postmark your ballot two days before the registration deadline, since the deadline fell on a Sunday. It was Cleaver who read the fine print. Long Distance Voter, like Vote.org, was technically nonpartisan. But many would argue that get-out-the-vote organizations inherently lean democratic, because the citizens most underrepresented in the voting process tend to be liberal. Slowly, over the years, Cleaver’s side project expanded into a website tackling every aspect of the voting process. By the time she moved to San Francisco in 2012, for a product manager job at Change.org, she was living a double life—working a lucrative tech job during the day, and spending her off hours running her voting organization. Ben Wikler, now a Vote.org board member, recalls hanging out with Cleaver at a Change.org staff retreat in 2012, shortly after he started with the company. The pair was hanging out with a group of programmers at the retreat in the Virginia countryside. One of the programmers showed Cleaver a tool that was broken; she became outraged. “She would just unleash a string of expletives about how terrible it was,” he recalls. “Every bug they would encounter would light her fuse again. It turned into a running game to make Debra outraged.” It seems like a funny anecdote, but it underscores something about what makes Cleaver good at nitty-gritty voting stuff. “That’s a kind of empathy for the user and the kind of emotional reaction to the tools that makes someone really good at building stuff,” explains Wikler. “It’s not just something on the to-do list when it makes you want to smash something or vomit.” But Cleaver’s transition to San Francisco’s tech scene didn’t go smoothly. She had always been comfortable in circles of men — she spent her twenties investigating police officers, after all. But the clubhouse vibe of the San Francisco tech scene surprised her. She found herself drowned out in meetings; her ideas were disregarded. She felt constantly questioned. In 2013, her difficulties at work culminated in an argument: Cleaver called her boss at Change.org a misogynistic prick (“It was a statement of fact,” she says) and got fired. She started consulting, but the ample amount of time was exactly what she needed to take her political projects to the next level. Two years later, Long Distance Voter won the Knight News Challenge, an award for innovative start-ups that came with a $325,000 prize check. After a cold email, the owner of Vote.org agreed to sell the domain name to Cleaver at a reduced rate. A few months after that, she was accepted into Y Combinator. It was time to take her voting innovations to the big leagues. I meet Cleaver only a few hours before her Lesbians Who Tech conference speech, sitting in the lobby, next to a booth where the only man in the room was hawking the Oculus Rift. (“The Oculus guy doesn’t like me,” she texts. “I have short hair and look worried about the election.”) When I find her, wearing denim and a black Etsy t-shirt, she seems relieved. “Usually I say I look like a lesbian, but that pretty much describes everyone here,” she says, ushering me out of the lobby in search of decaf coffee and something — anything — to eat. Cleaver is compact—just under 5'6"—yet when she talks, people tend to do what she says. Marching up to a bouncer after her talk, she tries to sneak me and her friend into the VIP lounge. At first, the bouncer’s skeptical. “I’m a speaker, this is my friend, and this woman is profiling me,” she says with a grin, and the bouncer shifts the door open. “I find when I smile people let me do what I want,” she tells me triumphantly. These are the first beers she’s had in a few days. For the last several months, she has been working at a constant clip, forgoing food, sleep, and haircuts. “I’m stress eating, I’m gonna get fat,” she tells me. “For everything, I’m like, ‘Will this increase voter turnout.’ If the answer is no, I won’t do it.” But her biggest insight — and the thing she most wants to pull off by next Tuesday — only came to her in June, while she was napping on the Caltrain while headed to a dinner in Mountain View with her Y Combinator class. She woke up with a thought: What if, instead of knocking on doors, you could find the phone numbers of unregistered voters and text them? Then reality set in. “I was like, is this legal?” she says. It was. Robocall laws prevent companies from sending automated texts to people who haven’t opted in—a detail that, for years, has prevented campaigners from using cell phones in a meaningful way. Obama’s 2008 campaign collected cell phone numbers from supporters, but only used them to send out text blasts, mostly asking for money. In 2014, the Analyst Institute, an elite organization that studies the data surrounding democratic campaigns, looked into whether text messages could be an effective way of pressuring participants to vote. In a study of 150,000 participants, those who received “plan-making” texts — messages that help someone figure out how to vote — were 1.4 percent more likely to vote. It might not sound like much, but as Cleaver points out, if you multiply that by the 100 million Americans who didn’t vote in 2012, that’s an additional 1.4 million ballots. Yet: How are you going to send 100 million text messages by hand? This year, an organization called Hustle figured out a loophole. As long as each message is sent by a human, users don’t have to opt in. Software can automate the message and type in a phone number—as long as a human hits “send,” in the end. Hustle used an early prototype of its software to send messages to prospective volunteers during Bernie Sanders’ campaign. When voters responded to messages, the campaign kicked off a conversation—much like a canvassing effort, but easier. (The Clinton campaign is now using similarsoftware.) Hustle’s reasoning was similar to Cleaver’s: 96 percent of people under 35 have smart phones. And though the majority of doorbells go unanswered, most text messages are read within three minutes. Why not meet people where they are—especially when it’s easier than routing a volunteer to their doorstep? Cleaver texted a friend at Hustle from the Caltrain. A few weeks later, she was sitting in their San Francisco offices, testing out the software. She sent a few prototype texts: “Hi Amy, This is Debra from Vote.org. There’s only a few days left to register to vote. I’m here to help you if you have any questions.” At the time, Spillane, the chair of Vote.org’s board, was on vacation in Greece. A week later, she returned to a fully funded test run of Cleaver’s project. “I was like, ‘Hey, we’re now running a half-million dollar SMS voter registration drive,’” a giddy Cleaver recalls informing Spillane. “‘Sorry I forgot to tell you.’” Cleaver was developing this project at Y Combinator, but in some ways she felt isolated from the group. “I would tell the guys in my group ‘I don’t want to solve, like laundry. You guys can solve my laundry.” It was no secret, Cleaver says, that Y Combinator was a “low priority” for her; she was less than six months before a presidential election—it was go time for her. But taking part in the program fast-tracked Vote.org into an elite roster. At a Y Combinator event, she spotted Jack Dorsey across the room, and marched over and asked him to tweet about Vote.org. He did. A few days later, Justin Bieber retweeted the tweet. Traffic to the site quadrupled in a day. A number of partnerships have launched. At one point, Cleaver was emailing back and forth with a woman; when she forwarded the exchange to Spillane, Spillane told her that she’d been corresponding with the publisher of Cosmopolitan. The edge that being at Y Combinator gave Cleaver often didn’t sit easily with her. “Sometimes I would just be like, ‘Wow, this is what access is,’” she tells me. “And I’m like — the fuck? Because all the other people here — they don’t even realize what they have.” As Vote.org has gained renown, Cleaver’s had to evaluate how to live with her newfound power. When she won the Knight News Challenge, for example, Cleaver realized she needed to get a formal outfit. A friend took her to Nordstrom, and put her in a pencil skirt. “You look pretty,” her friend told her. From the dressing room, she called another friend in tears. “I don’t want to be pretty,” she told him. “I want to look like the kind of person you write a million dollar check to.” Now she can name her entire wardrobe in a sentence: three Brooks Brothers shirts; one suit; jeans and plaid button downs. Cleaver has also found she is surprisingly good at fundraising. “I like talking to people,” she tells me. “It’s just learning that it’s OK to actually ask them for money.” Since graduating Y Combinator this past August she’s raised about $1.7 million, a number she’s the first to say is probably what her cohorts in the program raised in the first few days of graduation. Still, for Cleaver, who pays herself roughly half of what she could make on the free market, money isn’t the point. “I tried to go corporate,” she says, “I really did.” Throughout September, Cleaver struggled to set up a full-time call center for her SMS project. She started with a group in Florida, then swapped them for organizers in Tennessee. But no one seemed to be able to recruit a workforce in time for the election. Finally, on the first Sunday in October, Cleaver took matters into her own hands. She posted a job notice to the Bay Area Queer Exchange, a Facebook group, and sent an employee to Best Buy for Chromebooks. She texted a few friends and one offered to rent her office space in Oakland at cost. By the following Tuesday, Cleaver was surrounded by 19 ready-to-text employees in her newly opened operation. “I tell everyone, we are not running a sweatshop,” she tells me. “You can have fun as long as you keep pressing send.” One guy was learning Spanish by watching dubbed episodes of Buffy The Vampire Slayer; another woman read a book with one hand and texted with the other. A few weeks ago, Cleaver came in for lunch and there was music pumping — everyone was dancing. She joined them and they all bopped around. It would be easy to dismiss Cleaver’s ragtag feel-good group—except that by the time Election Day rolls around, they will have run one of the country’s largest get-out-the-vote programs, and one of the most cost-effective. By election day, Cleaver will have roughly 60 employees texting, and by texting, they can reach over 100,000 people per day. (Each time Cleaver raises money, she buys another book of phone numbers.) So far, they’ve contacted 1.3 million people and have bought the phone numbers of almost 3 million potential voters that they might reach by November 8th. Each completed voter registration form costs Vote.org just over $8. It’s just preliminary numbers, but that’s less than half of the $20 it takes for most other voter turnout organizations. And, the group is reserving 250,000 phone numbers as a control group, for when their results are studied by the Analyst Institute. If this works, it’s a new method of encouraging people to vote. Cleaver’s still adjusting to her newly prominent position, toggling between social enterprise and business. Stepping out the Lesbians Who Tech conference, Cleaver slips on a red backwards baseball cap—an accessory she uses to hide her uncut election hair. Despite the disguise, she is recognized. “Aren’t you the awesome Vote.org lady?” asks a woman holding a hand-lettered poster-board pointing to the afterparty. “Didn’t you get into Y Combinator?” Cleaver smirks. “Yeah, that’s me. I’m a capitalist now.” MORE FROM BACKCHANNEL: This Is the Smartest Thing Facebook Ever Did Do Startups Have a Drinking Problem? What I Saw Inside Apple’s Top Secret Input Lab Proof The Internet Really Has Changed Everything. Instagram is Ruining Vacation NOW WATCH: No one has slept in Dracula’s castle for 70 years — but Airbnb is changing that
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