Acronym, as the group’s founder and CEO Tara McGowan has told seemingly any reporter who would listen in the last year, was supposed to shake up Democratic politics. Faced with Republican opponents that now actually know how to campaign on social media, the non-profit digital strategy organization intended to offer an effective Democratic countermeasure, guided by digitally savvy hands of the Obama 2012 and Clinton 2016 campaigns.

After the disastrous Iowa Caucus on Monday, it’s hard to imagine that anyone is buying this story now. A faulty smartphone app, developed by the Acronym subsidiary “Shadow,” failed to correctly tabulate Iowa caucus votes. Though the Iowa Democratic Party says the vote counts are unaffected, the confusion has given ailing campaigns room to maneuver that they otherwise wouldn’t have had. Pete Buttigieg took the opportunity to declare victory, apparently based on nothing more than a gut feeling. Joe Biden, who has been slipping in polls for the past couple weeks, has asked for the actual votes to be invalidated.

According to an Acronym staffer, who spoke under condition of anonymity because of a non-disclosure agreement, Acronym is “far and away the most disorganized place I've ever been a part of.” Though Acronym’s initial statement to the press on Monday night kept Shadow at arm’s length, referring to it in the third-person and noting that it “also has other private investors,” this is a diversion.

According to my source, Shadow operates within the confines of Acronym, and its staff works with and alongside workers from other parts of Acronym in offices located Denver, New York, and Washington, D.C. The Intercept reported similar details on Tuesday afternoon, noting that as recently as last month McGowan identified Acronym as the "sole" investor in Shadow. The company appears to have edited its website in the last month, now claiming that it only invested in Shadow, rather than having “launched it.” McGowan herself tweeted the statement from Acronym early Monday, saying that Shadow is “an independent company that Acronym invested in.”

If you look at Acronym's "About" page today it says "we invested in Shadow" but if you look at the Wayback Machine from last month it's "we launched Shadow" pic.twitter.com/FM5XVddclh

— Kate Knibbs 🏄🏻‍♀️ (@Knibbs) February 4, 2020

It seems that Acronym, with its bold-faced plans to spend big in an effort to take down Donald Trump, perfectly encapsulates how in 2020 this money-soaked Democratic political culture inevitably leads to one place: failure.

Launched ahead of the 2018 midterms, Acronym was described initially as a “digital-first startup” (in the words of Axios), co-founded by McGowan and Michael Dubin, the founder of the men’s grooming company Dollar Shave Club whom you might recognize from their ads. McGowan, who previously worked as the digital director of the Obama and Clinton-affiliated Super PAC Priorities USA Action, was able to bring in money for Acronym’s affiliated political action committee Pacronym from a variety of well-known wealthy Democratic funders, including the billionaires George Soros and Marsha Laufer.

Acronym’s actual headcount is difficult to determine because of the hiring spree the company has been on in the last few months. In November, McGowan told the Times that Acronym and Pacronym had raised 40 percent of a planned $75 million, with the goal of deploying that money on anti-Trump advertising in five key battleground states: North Carolina, Pennsylvania, Michigan, Wisconsin, and Arizona, an effort called “Four is Enough" (based on the logic that only four of these five states are required to win a national election).

What distinguishes Acronym, McGowan told the Times, is the flexibility offered by its 501(c)(4) “dark money structure” — beyond the obvious advantages of being able to collect virtually unlimited dollars with no required disclosures. A flattering profile (“An A student with an attitude”) of McGowan that appeared on Ozy.com last September described Acronym as having “a web of for-profit companies beneath it,” one of which was “a political tech company with a peer-to-peer texting product” — Shadow.

Although this structure makes it seem that Acronym has the ability to reinvest whatever profits it makes, the Acronym staffer said it manifested as organizational chaos.

“They call it a ‘startup environment’ as an explanation for why no one knows what's happening,” the staffer said. Acronym did not respond to a request for comment by the time of publication.

McGowan’s theory of how digital campaigning works — churning out content for mass reach on social media — has gotten significant media play. In two  separate  Times articles published within a week of each other this past November, McGowan explained that the Democrats and their donors needed to get smart about digital. “We don’t need to spread lies or play to people’s insecurities to win, we just need to compete and get our message to voters every single day where they get their information,” she told the Times on November 1. “Right now, we’re not even on the field.”

“Trump has upped the ante by spending more than any candidate this early in a general election campaign,” she told the Times three days later, “and right now our side is simply not on the field.”

“They’ll say, ‘look at all these impressions we got!’ as if that has a correlation to persuasion, and not just being a billboard on the highway.”

As described by the Acronym staffer, McGowan and Acronym were hardly competing on the field she described. Staffers hired to churn out digital content sat in a room for at least a week, given no direction about what to do. There wasn’t a clear understanding about what the content strategy was supposed to achieve.

“They’ll say, ‘look at all these impressions we got!’ as if that has a correlation to persuasion, and not just being a billboard on the highway,” the staffer said.

These missteps are also not limited to ideas being badly executed — the problem is that the ideas were bad in the first place. A key project McGowan announced in a glossy Bloomberg Businessweek  profile in November was the launch of Courier Newsroom, a center-left content network designed to mimic the aesthetics of local news sites, which McGowan cheerfully spun as a replacement for actual local news.

As a digital strategy firm, Acronym’s idea of how to win the digital “war” against Donald Trump in 2020 also reflects this blinkered thinking. Much like Hillary Clinton’s doomed 2016 effort to campaign against “Dangerous Donald” — and to focus messaging on why Trump is a uniquely bad guy — McGowan (whom the staffer describes has an aggressive hand in Acronym’s content production) told the Times that Democrats must tell “a powerful, true, cohesive story about why this guy is dangerous.”

And whatever special alchemy to reach people that Acronym claims to possess, a Tuesday Daily Beast investigation notes, they don’t appear to have actually tried to tell that “powerful” story: the group reportedly only disbursed about $200,000 of the $1 million they had promised to spend on impeachment advertising against Trump.

“I think there’s been a lot of claims that have been made about the efficacy of digital that are out of line with the reality of electoral politics,” Sean McElwee, founder of the progressive advocacy group Data For Progress, told me.

Ironically, of all the parts of the Acronym organization, Shadow is the part working on some of the tangible initiatives. They built a small-dollar fundraising tool reportedly used by at least one campaign, and the purpose of the malfunctioning app built for the caucuses was to make the reporting of votes more transparent, in line with new rules issued after the 2016 election. But Acronym — in spite of its billionaire donors and well-connected founders — was unable to pull it off, as evidenced by Monday’s catastrophic failure in Iowa.

“There’s such a pervasive culture of self-dealing when it comes to consultants and party committees and stuff,” said Karthik Ganapathy, the co-founder of the Democratic messaging firm MVMT communications (Ganapthy’s partner, Mike Casca, is currently a senior adviser to Bernie Sanders though Ganapathy himself has no role on the campaign).

“And we have a situation where as a party if we are the good guys we have to be the good guys — not engaging in this,” Ganapathy told me. “There’s a reason why so many Americans think politics is an elitist plot to make a handful of people wealthier, and it’s kind of true."