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US election: Democrats try to blunt Donald Trump’s digital edge

After the debacle in Iowa, many in the party worry about its new campaigning technologies

CeCe Ibson was one of the lucky ones. When the app she was using to log votes at last week’s botched Democratic Iowa caucus gave her an unexpected error message, she continued using it until it appeared to correct itself. Many of her fellow party volunteers were less lucky. A series of glitches in the app prompted the entire process to grind to a halt, causing one of the most chaotic nights in the party’s recent history and prompting questions about whether the technology the party uses is fit for the brutal presidential campaign.
“When you do this, we are on the national and international stage,” Ms Ibson said afterwards. “The world is watching, and especially in this election cycle we were taking this very, very seriously. So yes, it was embarrassing that this did not work.”

Many who work closely with the party say the failure is indicative of a much wider problem with the digital skills it is bringing to the 2020 campaign.
Democrats are desperate to catch up with Donald Trump’s campaign, which won a reputation for its savvy use of social media in 2016 and is investing heavily in an array of campaigning technologies.
While television, newspaper and radio advertising remain dominant, campaigns are increasingly looking to social media, text messaging and other technologies to give them the upper hand in what is expected to be an extremely close presidential race — and one which may depend on turning out voters who are not easily reached by other methods.
But the Iowa debacle has underlined concerns within the party that the Democrats have wasted money and time developing technologies that do not work, replicate what is already available or build on flawed foundations.

“Why were we spending resources [in Iowa] on a relatively simple function, especially this late, when we knew this was coming for three years?” says one Democratic technology strategist. “There is a problem here more widely with the party and its decisions on technology.”
Theresa Payton, chief executive of security consulting group Fortalice Solutions, says of the party after the Iowa caucus: “They didn’t follow a guiding principle: if you’re going to fail, fail small, fail fast. Don’t fail colossal.”
Democratic fears over their technological prowess stem from the 2016 campaign, when the party found itself blindsided by a more agile and aggressive Trump operation which used Facebook in a way no one had before.

Brad Parscale, a 6’8” web designer with a Viking beard and a taste for inflammatory rhetoric, led the Republicans’ digital efforts from his office in San Antonio in Texas. Using detailed voter data — some of it obtained from Facebook users without their permission via the British consultancy Cambridge Analytica — he was able to target people in rural areas who did not usually vote.
Far from the confines of Washington, Mr Parscale felt free to experiment with different messages targeted at different groups. He spent tens of millions of dollars developing hundreds of different adverts for Facebook, provoking the fury of Mr Trump himself, who believed television to be key to winning elections.
“It was the first time he had really yelled at me,” he later told the Washington Post. In response he told Mr Trump: “If you are going to be the next president, you’re going to win it on Facebook.”
Senior executives at Facebook agree. Andrew Bosworth, who oversaw advertising on the platform at the time of the 2016 campaign, said in a recent post that he thought Mr Parscale’s work had been “unbelievable”, and constituted the “high water mark of digital ad campaigns”.

Mr Parscale has now been promoted to lead the Trump re-election campaign and is once again experimenting heavily with online advertising.
A glance at Facebook’s library of political adverts shows thousands of different Trump campaign posts, often almost identical but using subtly different language. Democrats for example are variously described as “radical”, “partisan” or “corrupt”. Sometimes they are not mentioned at all but in their place is “Nancy” — a reference to the Democratic Speaker of the House Nancy Pelosi.
“They are very creative about digital ad buys; they have thousands of different Google and Facebook ads,” says Max Wood, founder of Deck, a new voter-targeting platform being used by Democratic campaigns. “They throw a lot of shit at the wall and see what sticks.”

If Mr Parscale is to be believed, however, social media will play a far smaller role this year. Instead it is shaping up to be the election of the text message.
“This is how Donald Trump stays president for four more years,” Mr Parscale told a Trump rally in 2018, holding up his iPhone. “Now this phone is how we connect with you. It’s how we turn you into the army of Trump.”
One technique being heavily used by the Trump campaign is known as geofencing. This involves collecting the unique identification numbers of every mobile phone in a particular location — for example at a political rally — and then using the data to identify users and send them adverts afterwards.
The Democratic party organisation has historically been more decentralised and less centrally controlled than that of the Republicans. As a result, its response in the digital field has been to encourage entrepreneurs aligned with the party to experiment.

Investment groups have popped up in WeWork offices across Washington DC and in Silicon Valley. They include Acronym, which was founded by Tara McGowan, a former aide of Barack Obama, and which owns Shadow, the company whose app faltered so dramatically in Iowa.
Speaking to the Financial Times before the Iowa caucus, Kyle Tharp, Acronym’s spokesperson, was enthusiastic about another tool developed by Shadow which allows campaigns to send out text messages to thousands of supporters and activists at a time. “This kind of technology is going to play a big role in 2020,” he said.
Others might disagree. Campaigners for Joe Biden, a leading candidate in the Democratic primary race, reportedly gave up using Shadow’s texting tool after becoming concerned about its security.
Other pieces of technology are generating more enthusiasm, even if they pose new dilemmas for personal data privacy. One major area of investment is so-called “relational organising”, which allows campaigns to access and leverage their supporters’ contact books.

Campaigns can now tell their volunteers to download an app, and with the permission of those volunteers, scrape their contact lists and cross-reference them with their own lists of likely or possible voters. If matches are found between the volunteer’s contact book and the campaign’s voter list, the app can then automatically suggest sending that person a message, tailored to what the campaign knows about the voter.
Democrats were keen on developing such tools after seeing the Trump campaign experiment with them in the final weeks of the 2016 campaign.
Thomas Peters, chief executive of uCampaign, which made Mr Trump’s America First app, says: “The app might prompt you to text a daughter in Michigan about Obamacare, or email an aunt in Florida about the wall.
“In Michigan, we sent 6,000 matched texts,” he adds. Mr Trump won the swing state by just over 10,000 votes.

This time around, such apps are likely to be even more sophisticated.
“At the moment campaigns can manually edit suggested messages to tailor them to their audience,” says Michael Luciani, chief executive of The Tuesday Company, whose Team app is being used by several Democratic candidates. “But in the future we are hoping to use machine learning so the app can make these edits automatically.”
The Tuesday Company is being backed by another investment vehicle, known as Higher Ground Labs, which has also been set up by former Obama staffers.
Betsy Hoover, a co-founder of HGL, says the party has “an incredible bench” of technology experts developing tools to defeat Mr Trump. “If those experts are empowered with the resources and influence necessary, we can gain significant ground this cycle and run relevant, successful programs,” she says.
One of HGL’s investments is in Mr Wood’s company Deck, which uses machine learning to tell candidates who their target audience should be in any given location, based on publicly available consumer and voting data.

Some Democrats believe all this experimentation will bear fruit over the next few months as they look to take on the Trump campaign in new and unexpected ways.
Others however are not so sure.
Tim Lim, who had advised Democratic campaigns on digital marketing, says: “The real question is going to be, can everything we are testing and learning and doing be applied in what will be one of the more insane general election environments? The Trump campaign is starting now; is whatever we are doing effective?
“You have one side doing whatever it takes to win. How do you fight in that type of environment?”
Whatever tools the Democrats develop will only help them compete if the data behind it are up to scratch. And this is where Democrats worry that Republicans have a big advantage.

For the past 10 years, Charles Koch, the billionaire and Republican donor, has been running a company called i360, which hoovers up as much voter data as possible to be used by conservative candidates.
Using data from commercial sources, voting records and previous campaigns, the company claims on its website to have built “a comprehensive data resource of all voting Americans”. i360 can then sort that data so that candidates can target particular sections of voters, for example “individuals who have a high likelihood of believing that undocumented immigrants should be required to leave the United States”.

Campaigners predict that having a central database and targeting tool such as this will prove invaluable, especially as social media companies have begun restricting what they are willing to share after the Cambridge Analytica scandal. In recent months Twitter has banned political adverts, while Google is not allowing campaigns to target users based on party affiliation or voter records. Facebook has decided not to limit political advertising, but is being more transparent about who is targeting which ad at which audience.
“Republicans have built a stark advantage in political data through massive, seemingly unlimited investments from i360,” says Shomik Dutta, co-founder of Higher Ground Labs with Ms Hoover. “They have established a flywheel at the centre of all Republican campaigns and causes that has improved upon itself for years.”

The problem is that without a backer such as Mr Koch, the Democrats have simply found it too expensive to develop their own version.
Howard Dean, the former Democratic presidential candidate and governor of Vermont, is creating a “data exchange”, which will allow various databases used by Democratic campaigns across the country to communicate with each other and share information. “The Republicans have spent well over $100m, possibly $200m, on this,” he said. “It would be too expensive for us to create one database.”
But this is another area where some are worried that the Democratic approach lacks co-ordination. Mr Dean is heading one of three separate projects to create a similar data resource, the others being Michael Bloomberg, the former New York mayor and current presidential candidate, and Reid Hoffman, who co-founded LinkedIn.

Jessica Alter, co-founder of Tech For Campaigns, which provides technology and digital training for Democrats, says: “This is why it is so important that we invest in a centralised technology and digital arm for the Democrats that is well resourced and lasting.”
She adds that, in contrast, the Republicans had a “centralised funding mechanism and the right team behind it”.
But Mr Dean insists the party’s entrepreneurial approach will pay off.
“We must recognise the important role that for-profit investment can play in politics,” he says. “Democratic political funders have a large funding gap to close in order to catch up. Thankfully, we have endless energy and talent waiting to help.”

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