When Shomik Dutta woke up the day after Donald Trump’s shock victory in 2016, he decided the best way for the Democrats to fight back was through technology. A veteran of Barack Obama’s White House, he immediately began an operation to raise funds not for candidates, but for the start-ups he hoped could develop new tools for reaching voters.

“Nothing clarifies the mind quite like losing,” says Mr Dutta.

He had watched Republicans rebound from their own defeat in 2012 by redoubling their efforts to use new technology in their campaign, with the help of wealthy donors. The Koch brothers are reported to have poured tens of millions of dollars into i360, a state of the art data platform, while the Mercer family backed Cambridge Analytica, the data analytics firm that worked for the Trump campaign and is now notorious for obtaining the leaked Facebook data of up to 87m users.

The language of online campaigns is tweaked for different audiences, such as those for Beto O'Rourke, the Democrats' senatorial candidate in Texas

With Betsy Hoover, a political organiser for the Obama campaign, and Andrew McLaughlin, deputy chief technology officer in the Obama White House, Mr Dutta founded Higher Ground Labs, an incubator for political start-ups. They persuaded funders — including Silicon Valley venture capitalists Reid Hoffman, Ron Conway and Chris Sacca — to invest in companies that pledge to only work with Democrats and progressive causes.

The portfolio includes companies that use data to profile voters and donors, start-ups that crowdsource advertising and funds and even one that uses artificial intelligence for opposition research.

“I wanted to use a disciplined, market-based approach to equip the entire party with cutting-edge technology to win, quickly scaling things that work and ruthlessly euthanising things that don’t,” Mr Dutta says.

The midterm elections next week, which give the Democrats their first chance to try out these online marketing strategies, is taking place during a period of soul-searching about the role of social media in elections — an unease that has been amplified by the Cambridge Analytica scandal.

Social media is becoming an ever more important battleground for campaigns to reach voters, who would have once been targeted through television advertising. About two-thirds of Americans use Facebook, and about three-quarters of them go on the site every day, according to the Pew Research Center.

Different messages for Nevada senator Dean Heller. Facebook's archives allows users to see the different messages

Using platforms such as Facebook , campaigns can slice voters into specific groups, allowing them to test which messages resonate before trying them out in larger campaigns or even on stage at rallies. This November, campaigns will spend more than $1bn on digital ads in what will be the most expensive non-presidential election yet, according to research by Borrell Associates.

The issue facing Mr Dutta and the other Democrats trying to boost the party’s online campaigning is whether they will end up trampling on the privacy of prospective voters in some of the same ways that caused so much controversy in the 2016 campaign.

While many Democrats believe they can win online without playing dirty, some fear that this is a losing battle. Dustin Buss, co-founder of CallTime.AI, a fund­raising platform funded by Higher Ground, says: “The question facing the Democratic party right now is: is this a moral race or is it an arms race?”

James Slezak and two fellow physics PhDs founded Swayable, a data science company funded by Higher Ground, to solve a problem that Mr Slezak had seen when he led digital strategy for the New York Times: the challenge of preaching to anyone other than the choir.

“It is extremely hard to change people’s minds,” says Mr Slezak. Swayable is now being employed by campaigns up and down the ballot to do just that, including by Andrew Gillum, the Democratic nominee for governor of Florida.

Swayable uses data science to design experiments that test how people respond to different videos. A campaign creates several different versions of its message and Swayable shows them to thousands of recruits from platforms such as Amazon or even games and productivity apps. For example, Swayable can test how to win sympathy for undocumented migrants from someone sitting in a rural part of the country, where there is little support for them.

WASHINGTON, DC - APRIL 29: (L-R) Shomik Dutta, Alexandra Echevarria, Jon Favreau and Emily Black attend Eric Podwall’s exclusive cocktail experience the evening before White House Correspondents' Dinner at Sheppard on April 29, 2016 in Washington, DC. (Photo by Ilya S. Savenok/Getty Images for Eric Podwall)
Higher Ground co-founder Shomik Dutta, left, says 'I wanted to use a disciplined, market-based approach to equip the entire [Democratic] party with cutting-edge technology to win'

“They are sitting in a town where everyone watches Fox News and all their friends have told them something. As a result, the kinds of stories that can move them are different from the kinds of stories that move people who go to brunch on the coasts and discuss this issue every Sunday,” Mr Slezak says.

Where Cambridge Analytica harvested data that users had been told was intended for research — and also took information on their friends — Swayable says its users know what data they are giving because they are explicitly asked for it when they fill in forms. They are never asked for personally identifiable information, just for categories such as their income range.

Mr Slezak believes Cambridge Analytica “talked a big game” but he does not think finding the best way to pull someone’s heart strings is anything like the psychographic profiling that it claimed to do, categorising people according to a series of personality traits.

Higher Ground Labs encourages its companies to secure their data and be transparent about what they collect. “In my mind, [Cambridge Analytica’s] biggest downfall was they lied about what data they had and what they were going to use it for,” says Ms Hoover.

Mr McLaughlin is working on a set of ethical principles for the left-leaning companies to follow. It covers collection — obtain consent and do not harvest the data in a fraudulent or “sneaky” way; and how it is used — do not use it to suppress the vote or spread disinformation. To Mr McLaughlin, targeting people by values such as “equality” or “tradition” is fine, but profiling their emotional state is not. As AI improves, he believes campaigns should steer clear of any technology that makes decisions that are unexplainable.

“We do not want to unilaterally surrender capabilities to the right — nor do we want to behave as though the ends justify the means,” he says.

FILE- In this Oct. 22, 2018, file photo people vote on the first day of early voting in Miami-Dade County in Miami. If Democrats win control of the House in next week’s congressional elections, their legislative priorities wouldn’t likely much alter a $20 trillion U.S. economy. For one thing, President Donald Trump would remain able to block Democratic initiatives, just as they could stop his plans for more tax cuts and a 5 percent cut to Cabinet department budgets. What instead would likely result is continued gridlock. (AP Photo/Lynne Sladky, File)
Early voting for the midterms in Miami-Dade county © AP

For some independent observers, however, the current campaign is exhibiting many of the same practices that were heavily criticised after 2016.

Jeff Chester, executive director of the Center for Digital Democracy, a privacy non-profit group, says psychological assessments have become “controversial and largely off-limits” but similar practices persist. “The Cambridge Analytica disease has penetrated well into the digital media political ads business,” he says. “It is extremely disturbing that both parties and special interest groups are fully taking advantage of all the personal data you can buy today in online marketplaces.”

Moreover, the sort of self-imposed principles being developed by Higher Ground Labs may be the only guides that politicians either side of the aisle have to follow, given that the social media platforms, Congress and the Federal Election Commission have so far held off from significantly tightening the rules.

In the past year, Facebook has introduced tweaks that have made some information harder to access, but the biggest change in how developers could access data on the platform dates back to 2015. Cambridge Analytica received the data from Aleksandr Kogan, a Cambridge academic who obtained it for research, before Facebook decided to scale back which data developers could access.

In response to the threat of legislation amid concerns about “dark ads”, campaigns targeted so tightly that few users would see them, Facebook, Google and Twitter now run archives where you can search for all political ads by candidate or theme. But the main way this seems to have changed campaigns’ behaviour is by giving them another tool to keep an eye on the opposition.

Jessica Baldwin-Philippi, an assistant professor in political communication at Fordham University in New York, says the FEC has been “terrible” about designing rules for political ads on social media — and she has not seen any signs that the Cambridge Analytica scandal means they are coming up with anything more concrete than the archives the platforms have already put in place.

US Rep. Beto O'Rourke (D-TX) takes the stage for a Senate race campaign rally in Dallas, Texas, on October 20, 2018. - O'Rourke is running against incumbent Sen. Ted Cruz (R-TX) in the upcoming midterm elections. (Photo by Loren ELLIOTT / AFP)LOREN ELLIOTT/AFP/Getty Images
Beto O'Rourke and his team © AFP

For all the energy going into developing new technologies, some campaign experts believe the more interesting approach is to use existing tools to harness the energy among activists.

Smitha Chadaga, a doctor from Oregon, was not even on Facebook before the last election but has since joined after vowing to become politically engaged. Dr Chadaga says she was pushed into action after her six-year old son asked if he had to leave the US when Mr Trump won in 2016. “He was worried if he belonged here,” she says. “I’m a woman of colour, a physician who believes in science. I felt like I was being erased from this country and my son’s future was at risk.”

Volunteers have been turbocharged by technologies that allow them to reach people quickly and with more authentic messages.

Dr Chadaga has worked with Indivisible, a pro-Democrat campaign that has borrowed tactics from the Tea Party, the rightwing grassroots group. She joined the 9,000-strong Physician Women for Democratic Principles, forming her own chapter in Oregon: Drs for Kate, after Kate Brown, the Democratic governor.

Mass texting applications — embraced by both sides — allow her to reach out to others during workouts, on her lunch hour or doing chores. “You send 50 texts in two minutes. So if I get to the school to pick my kids up early, I can send 50 texts,” she says.

Higher Ground Labs is backing many companies in the world of “relational organising” — and Ms Hoover says the midterms will be an important testing ground for what volunteers can do in the 2020 presidential election.

Ads for Donald Trump on Google which gained more than 10m impressions

“If you hear about a candidate for a cause from a friend or someone that you already trust, the message has a bigger impact than from a campaign or brand or organisation you don’t necessarily trust,” she says.

The Tuesday Company, one of those companies, has clients in 25 states, where campaigns send their volunteers content to share on social media using the Team app. VoterCircle helps campaigns leverage “super influencers” to persuade undecided voters, like brands that try to win over Instagram stars.

Robby Mook, former campaign manager for Hillary Clinton, says that instead of obsessing over “this or that magical tactic”, it is clear that having a grassroots presence on social media will be “essential” to building the next presidential campaign. “A candidate’s success will ultimately rely on her and his ability to build a fan base that can both spread the message and sustain the campaign with donations,” he says.

The future could even be individual voters making and promoting their own ads. HelloSociety was created when its founders saw the power of social media advertising deployed by Mr Trump — and hoped to use it to bridge the gap between the president’s supporters and their opponents. One project being tested, Minus 45, allows people to create their own ads targeted at winning over Trump supporters. People are even organising parties to test the messages out.

“If Jeb Bush didn’t have the right message, and Marco Rubio didn’t, and Hillary didn’t, what could be a good message to the right person may come from a human being,” says Brendan Lind, chief executive of Human Agency.

But Mr Lind also worries that however much the Democrats invest in technology, they may be perpetually playing catch-up with Mr Trump and his team’s ability to use social media to fire up the president’s supporters.

Even for those who want to take the high ground, the possibility of another Trump victory could prove too much. Mr Buss says: “If we had another 2016 in 2020 and Democratic tech stood some hard and fast moral line and Republican tech did exactly the same thing again and they blew us out again, that would — for sure — be different.”

Archives Details fall short on Facebook ‘paid for’ slots

The transparency efforts of the big internet platforms have been criticised for being, at best, translucent: you can see some data, but far from everything.

Facebook, Google and Twitter all launched archives of political ads in response to the Honest Ads bill put forward by US senators in October 2017 to regulate online advertising.

On Facebook, the ads are shown with a broad range of how much was spent to promote each post and who it reached, broken down by age, gender and region. But any more detailed targeting information is hidden.

Advertisers have to prove they are American and therefore legally allowed to buy political ads in the US, with identification and a code to verify their account sent on a postcard to their mailing address. But once authorised, an advertiser can write whatever they want in the box that says “paid for” — as shown when journalists from Vice bought ads under the guise of Isis and US vice-president Mike Pence.

Meredith McGehee from IssueOne, a non-partisan, non-profit organisation that aims to reduce the role of money in politics, says it was not a meaningful way to give information about the source of the money for the ads.

Even a super-political action committee, required by law to disclose their donors, can write in whatever it wants in Facebook’s “paid for” box.

“If the super-Pac says my donors are Americans who love America — who the heck is that?” she says.

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