The walls of DigBoston's small Charlestown office are lined with old issue covers, books on Boston history, journalism award plaques and, hanging above it all, a bright yellow “W” — the logo for the rap group Wu-Tang Clan.

“This is a group of artists who actually did things on their own terms, have largely answered to no one but their own crew, and have had unbelievable success,” said the Dig's editor-in-chief Chris Faraone, who wrote about Wu-Tang earlier in his career. “Absolutely, without a doubt, Wu-Tang is my chief inspiration.”

For the past couple of years, Faraone — along with executive editor Jason Pramas and publisher John Loftus — have tried to put out over 30,000 copies of a free newspaper every week and do it on their terms, in an era that has not been easy for print media.

In Boston, on top of layoffs and buyouts at The Boston Globe and Boston Herald, the Boston Phoenix closed in 2013, and The Improper Bostonian magazine was shuttered in April. And yet, DigBoston has managed to hang on, marking its 20th anniversary this year.

If you’ve never picked up a copy of DigBoston from one of those black or orange plastic sidewalk boxes, here are the basics: It started in September 1999 as a free paper called The Weekly Dig. For years, it coexisted with the larger, more established Boston Phoenix, positioning itself as a sort of alternative-to-the-alternative.

If you believe the Dig’s own oral history, DigBoston was, in its earlier years, a fairly chaotic place to work: the type of place where the owner would get into monthly fights with the editor-in-chief, where a person could do cocaine in the middle of the office, and where the "extreme metal columnist" could write several articles featuring white power bands, apparently without any editors noticing.

“The Dig was a wild place at the time," said Faraone, who described his first job there as an intern in 2004. Nowadays, he said, “everything is really more buttoned up.”

Today, DigBoston consists of a weekly print issue and a website. The publication focuses mainly on the city’s arts scene, news with an anti-establishment flavor and a generous sprinkling of opinion.

DigBoston touts itself as “Boston’s best and only alternative weekly publication.” And, like most alt-weeklies, it publishes some articles that might be too taboo for more mainstream newspapers. Take for instance a regular column written under the pen name "Citizen Strain," featuring reviews of various marijuana products and THC delivery devices.

“Maybe someday, but for now, I don’t see The Globe doing dab reviews,” said Faraone, referring to a type of cannabis concentrate. “There will be no bong hits in the Herald newsroom … but we’re happy to do it.”

Tattooed on Chris Faraone's fingers are the letters B-I-N-J, which stand for Boston Institute for Nonprofit Journalism. (Adrian Ma/WBUR)

The publication has also been happy to capitalize on advertising dollars from Massachusetts' burgeoning legal cannabis industry.

“Marijuana's becoming a huge thing in Boston and Somerville and Cambridge, and people need a place to put these ads, said Dawn Martin, a senior sales executive for the Dig, with a laugh. “Some places won't take them, but we will.”

Courting advertisers is something that Faraone, Pramas and Loftus spend a fair amount of time doing: the trio used to work for the Dig; now they're co-owners. When they bought the publication in 2017 from its founder, Jeff Lawrence, the partners said the company was over $400,000 in debt and had trouble paying its writers, staffers and the IRS.

Finances have improved since then, but it's still a struggle to break even every month, they said.

‘We’re An Aberration’

While the pages of DigBoston are filled, in large part, by a rotating ensemble of freelance writers, the only full-time employees are the co-owners themselves. That means each partner has to wear a lot of different hats.

On a recent Tuesday, Faraone spent the day ping-ponging between job titles: In the morning, he was a reporter, interviewing a Boston reggae artist; an hour later, he was an editor, nudging writers to finish their articles; after lunch, he was the sales manager, reviewing ad designs for potential clients.

The routine, Faraone quipped, is that there is no routine.

“It’d be much easier if I could just be a staff writer. I always say that my goal is to one day be a staff writer again,” he said.

From left: Chris Faraone, editor-in-chief of DigBoston, Dawn Martin, senior account manager, and John Loftus, publisher, discuss potential advertisers for an upcoming issue. (Adrian Ma/WBUR)

But for now, Faraone — who has a reputation for hurling insults on social media at politicians, other media outlets, Catholics and sports fans — has to think about the company's finances. While DigBoston declined to share detailed financial information, the partners said print and digital advertisements make up only about 65% of revenue. The rest is filled in by a growing list of side hustles: email marketing, custom printing and a cannabis newsletter called "Talking Joints Memo."

“We’re kind of an aberration,” said DigBoston’s film editor, Jake Mulligan, of the company's expanding portfolio of revenue streams. “If Dig didn't exist, you couldn't really pitch a business model by which it would exist. You couldn't pitch what we're doing today and get it funded.”

An Alternative Revenue Model

Diversification has been key to the Dig's survival and its ability to do longform local reporting — a type of journalism that’s been difficult to find support for, Farone said, as national news seems to consume more and more of the public’s attention.

“Everybody’s constantly pulling their hair out of their heads about the president when, sadly, they don’t even know in their own community, what’s often happening,” he said.

Seeing a need for local reporting but little interest from advertisers, Faraone and Pramas came up with what was, in the world of alt-weeklies, an unusual solution. In 2015, they created the Boston Institute for Nonprofit Journalism (BINJ).

According to its website, BINJ took in nearly $200,000 in donations in 2018. That money has allowed the Dig to feature reporting it would not otherwise have been able to afford, such as an investigation into the Massachusetts State Police, a deep dive into racial disparities in Boston’s liquor licensing system and a feature story on Boston’s Asian LGBTQ community.

From left: editor-in-chief Chris Faraone, executive editor Jason Pramas and senior account executive Dawn Martin. (Adrian Ma/WBUR)

Despite having some success with BINJ, the owners of DigBoston are still trying to figure out how a free publication can survive when ad dollars keep moving online. In any given month, the partners said, finances for the Dig's parent company, Dig Media Group, Inc., waver between red and black.

That's what brought about the demise of the Dig's former competitor, The Boston Phoenix, according to Dan Kennedy, an expert on local media and associate professor at Northeastern University.

“You had club ads gone to Facebook. You had pages after pages of classifieds: 'I want a roommate;' 'We need a bass player;' 'I’m looking for a girlfriend.' All that's gone to Craigslist,” Kennedy said.

As a result, alt-weeklies around the country have been closing. A decade ago, the Association of Alternative Newsmedia had about 135 members. Today, it has about 100. But by fundraising through a nonprofit, Kennedy said, DigBoston is trying something no alt-weekly has done before.

“I think that what the Dig has done in essentially having a mind-meld with a for-profit paper and a nonprofit is brilliant,” he said. “If it works here, it could very well be a model for an alt-weekly market that just continues to shrink.”

Already BINJ has inspired at least one similar journalistic venture in Arkansas, called the Arkansas Nonprofit News Network (ANNN), which raised about $60,000 in 2018 to fund long-form journalism projects.

Complicating the search for a working business model, is an existential question for today's alt-weeklies: What makes a publication truly “alternative"?

Historically, alt-weeklies have often been ahead of the mainstream when it came to topics such as such as LGBTQ rights, gay marriage and marijuana legalization. But as those conversations have migrated toward the center of cultural discourse, the alt-weekly has increasingly become just another news outlet.

“The term ‘alternative’ is functionally meaningless at this point. We're a news operation,” said DigBoston's executive editor Pramas, but he added: "We have a certain rebellious spirit."

Of course, as is the case with any business, the gulf that separates ideals from reality is hard to fill without a steady stream of funding.

Cash Rules Everything

Chris Faraone, edtior-in-chief of DigBoston, in the office with publisher John Loftus. (Adrian Ma/WBUR)

“We're all fish swimming in a capitalist sea,” Pramas said, and unless that changes, the Dig’s owners expect to continue experimenting with new revenue models.

This year, for instance, they will try something they haven’t done before: event partnerships. That means in addition to writing about events such as the Boston Comedy Festival or the Boston Science Fiction Film Festival, the company will also sell tickets through a website called Dig Box Office, taking a cut of each sale. And while this might strike some folks as a too-cozy tie between business and editorial, Faraone has an answer for that.

“If you’re going to be in independent media like we are, there are a lot of things from journalism school that you just have to throw right in the garbage,” he said.

From Faraone's perspective, every dollar they bring in, is another dollar of journalism they can do. Plus, what choice do they have?

“If we don’t all come up with solutions like this, if we don’t all start doing stuff like this, we’re gone," he said. “And then what? I’m going to be a journalist with no job and no money and all sorts of ethical credentials? That’s crazy!”

You can have ideals. But if you don’t have money, you don’t have a paper. Or, to put it in the words of the song "C.R.E.A.M." by Faraone’s beloved Wu Tang Clan: “Cash rules everything."