Why a Hell’s Kitchen print magazine pivoted to newsletters

Phil O’Brien realized that distributing a print magazine during the Covid shutdown would be impossible.

The media startup developed a membership model that involves asking the audience what news should be covered.

The onset of the pandemic shutdown in March 2020 dealt massive blows to the vast majority of NYC businesses, but it was especially bad timing for W42ST, a print magazine based in Hell’s Kitchen. “We were publishing our first best-of awards issue,” founder Phil O’Brien told me. “We had over a thousand people vote for their favorite bars and restaurants, and on March 30 we planned to hold a big event that invited 300 people and was sponsored by Wells Fargo.” 

But by March 12, O’Brien had acknowledged to himself that his entire business model was about to collapse. On that day, he had lunch with his editor. “I told her that this isn't going to end well, and that we're definitely not going to be able to do the awards,” he said. “I also predicted that we’d have to suspend the magazine because I didn’t believe Broadway” -- one of the magazine’s top advertisers -- “would stay open. And she was like, ‘Oh, so you're just being pessimistic. Broadway's not going to close.’ And then we overhead someone at the next table say, ‘have you seen Broadway's closed?’”

By the next day, O’Brien decided to suspend publication of the print magazine. “It wasn't worth printing, because we wouldn't be able to distribute it,” he said. “We didn't know whether it was safe to do so. We also suspended the awards event. But we decided we wanted to stay busy, so we moved to publishing a daily newsletter.”

Building a print-based business

You might be wondering at this point why W42ST, founded in 2014, operated as a print magazine at all. Most local news startups these days launch as digital-only publications. O’Brien is the first to admit that his decision wasn’t exactly financially sound. “I'm a contrarian,” he said, laughing.

He got his start as a press photographer, working in the 1980s for a series of local and national newspapers in the UK. Then in 1985 he founded EMPICS, a company that eventually evolved to compete with Getty and other photo-licensing agencies. He sold that business in the early 2000s for a nice sum, and for the next few years he floated through a variety of different jobs before deciding to move to New York in the early 2010s.

O’Brien landed in Hell’s Kitchen and quickly decided that the neighborhood didn’t get the recognition or media attention it deserved. “It's been an area that a lot of New Yorkers have kind of looked down their noses at,” he said. In 2014, a UK friend of his who worked in magazine publishing got laid off from his job, and the two began discussing the idea of launching a free lifestyle magazine geared toward Hell’s Kitchen residents and businesses. In October, they printed their first issue.

While print magazines are inherently more expensive to run than digital-only news sites, O’Brien strived to keep costs low. “I didn’t have the budget of a Conde Nast or Hearst,” he said. He distributed W42ST in a variety of local businesses, with a special focus on luxury apartment buildings. “They'd be in bars, restaurants, liquor stores. They were very popular in hotels. And then we had street box deals in Grand Central Terminal and by Macy's.” With each issue costing him about a dollar per copy to print, he kept close track of which locations had low pick-up rates and adjusted his distribution accordingly.

Though the magazine had beautiful photography and design from the beginning, it took several months for him to get a handle on the content. He described it as generic and “not very local.” But then he met Ruth Walker, a longtime journalist who’d spent the previous few years as a newspaper lifestyle editor. Walker came on as editorial director after the third issue of W42ST, and O’Brien credits her with establishing the magazine’s voice and point of view.

Because the magazine was free, O’Brien relied almost entirely on print display advertising to fund it. “We charged about $3,000 a page,” he said. “So every month we really needed to sell about 12 to 15 pages, with the hope that most were single or double pages.” Most of the advertisers were local, with a fair bit of business coming from Broadway. O’Brien was always frustrated that companies from outside Hell’s Kitchen didn’t try to lure the neighborhood’s residents out by buying ads. He tried to pitch New Jersey real estate developers, for instance, to no avail. He did most of the ad sales himself. “Trying to get the pages sold every month was a tough gig.” 

Even before the pandemic hit, the magazine wasn’t especially lucrative, and O’Brien burned through a sizable chunk of the money he’d made from selling his photo agency. And then once the city started shutting down, it was immediately clear to him that the print version of W42ST wouldn’t be able to ride out the storm. If there was any hope of survival, it needed to pivot to something much leaner.

Launching a daily newsletter

In some respects, W42ST wasn’t exactly well-positioned for a digital-only transition. Over the magazine’s six-year history, O’Brien had experimented with placing some of its content online, but he ultimately decided to create a simple landing page that did little more than point visitors to where they could pick up the print magazine.

Still, it had some advantages. For years it had operated an Instagram account that had grown to over 10,000 followers via a mixture of staff photography and user-submitted images. “I started direct messaging its followers and saying, ‘hey, have you heard what’s happened? We’ve suspended the print publication but we’re doing this daily newsletter. You can sign up here.’ I would message people until Instagram blocked me because I’d messaged too many people. And then the next day I would get unblocked and start messaging people again.”

The magazine had also been publishing a weekly newsletter that curated local news and went out each Friday. “So March 13th was a Friday, which is when we normally sent out our weekly newsletter,” recalled O’Brien. “So I wrote it that day and told subscribers that we were suspending publication and moving to a daily newsletter, and here’s the link if you want to sign up for the daily version.” Within a few days, several hundred people had signed up for the daily version (the weekly list is still maintained separately). A year later, the newsletter is now up to 4,000 subscribers, with about a 35% open rate. 

The newsletter’s format is fairly consistent. It opens by excerpting and linking to a longer article that W42ST published to its website. For instance, in early February O’Brien published a 900-word article that investigated a mysterious howling sound that had been heard by thousands of Hell’s Kitchen residents. He used the newsletter to crowdsource information about the source of the sound and then wove together their responses. The site also publishes a regular “West Side Stories” feature in which a prominent resident is asked a series of questions about their life in Hell’s Kitchen.

The middle section is called “what we’ve been reading” and curates articles from outside news sources. “It’s stuff that’s relevant to you as a New Yorker,” said O’Brien. “It will be a news item about something happening on the subway. It might link to the latest weather reports. We might feature a piece about what it’s like to work from home on your bed.”

The final section is simply called “Freeze Frame” and features a single photo, either taken by someone at W42ST or submitted by a reader.

Monetizing the newsletter

As I mentioned, the daily newsletter is up to about 4,000 subscribers. That might not sound like massive scale, but given the outlet’s local niche, there are likely plenty of Hell’s Kitchen businesses that would pay decent rates to reach those residents. Speaking to O’Brien, however, I got the sense that he isn’t in a big hurry to monetize, and is instead waiting until the city reopens before he begins pursuing sponsorships in earnest.

That’s not to say he hasn’t generated any revenue from the newsletter. “We looked at the local news models around the country and saw that a lot of outlets have asked for support,” O’Brien said. He began testing out different requests for donations, which collectively brought in about $16,000 from 250 separate readers, some of whom are contributing on a monthly basis.

O’Brien’s also begun to test out some sponsorship models. “We will not run programmatic advertising on the site,” he said. “We will find a good way to serve relevant advertisements.” He’s experimented with a few local advertisers to run promotions at the top of the page, and he plans to get more serious about selling ads in mid-March.

At the end of our conversation, I asked O’Brien if, in retrospect, he wished he’d forgoed the print magazine entirely and launched as a newsletter instead. After all, he was now operating W42ST at a fraction of its previous costs, and he’d established a much closer tie to his readership. “If I had saved the money that I’d put into the print magazine, I could invest in so many things that would make me more competitive in the space,” he admitted.

There are other reasons he wishes he’d switched over to a newsletter sooner. With the print magazine, he had very little insight into who was reading or what the audience got out of any particular article. “Newsletters are really interesting, because the inbox is so intimate. When you see the open rates, you think, ‘wow, someone’s giving me their time.’” He’s been gratified by the outpouring of support, especially when it comes from complete strangers. “What I really love is when I see a donation from someone for $100, and when I look at their name I have no idea who that person is, but they’re obviously getting value from the newsletter.”

While reading through various articles the outlet’s published over the past month, I noticed that local readers were piping up in the comments section, which is a good indication that the community is seeing real value from its journalism. I thought this was illustrated best by a comment left at the bottom of an interview with broadway actor Stephen Carlile, a resident of Hell’s Kitchen:

“Thank you so much Stephen,” the comment reads. “This interview lifted my spirit and helped to remember there is beauty right in our own neighborhood!”

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Simon Owens is a tech and media journalist living in Washington, DC. Follow him on Twitter, Facebook, or LinkedIn. Email him at simonowens@gmail.com. For a full bio, go here.