Do Morning Newsletter Writers Dream of the Hectic Half-Asleep?

Surveying the ongoing battle to be the first thing people read when they grab their phones in the morning

First a Beltway preoccupation, the competition to be the first thing readers see when waking traces back at least as far as fax machine-based clipping services. But the most recent generation dates back to the June 2007 launch of Mike Allen’s Playbook and its battle cry to “win the morning.” Buoyed by the recent newsletter boom, the morning briefing has spread well beyond politics, but many prominent morning newsletters today have ties back to Playbook: Allen left Politico in 2016 to found Axios, where he writes a popular Axios AM newsletter; Jake Sherman and Anna Palmer took over after him, co-writing Playbook before striking out on their own earlier this year to co-found Punchbowl; and Playbook is still chugging along under the bylines of Ryan Lizza, Rachel Bade, Eugene Daniels, and Tara Palmeri. Sherman argued that we shouldn’t read too much into those connections. “A newsletter is just a name, right? I don’t think that any newsletter has any DNA,” he told The Fine Print. “A newsletter is kind of who is at the helm at the moment.”

Fair enough, but those three major players in the morning news-briefing field do share a D.C. sensibility and, probably, a sizable portion of their audiences. They temper the essential contradiction of the morning briefing — how to combine the intimacy of waking up next to someone with the rigors of a mass audience development strategy — by keeping the perspectives of D.C. insiders, rather than just anybody, in mind. Even The New York Times, which has made its flagship newsletter The Morning a key component of its subscription sales push, has put a former D.C. bureau chief, David Leonhardt, in charge of its daily wakeup call.

It takes a leap of imagination for a morning newsletter writer to picture their reader opening their latest dispatch, hair disheveled and teeth unbrushed. Punchbowl sends its first newsletter of the day between 5:50 and 6:15 a.m every day, but Sherman is up earlier, “in the wee hours of the morning.” Like a monk observing matins, he has grown used to the rhythms after taking over Playbook with Palmer in 2016. Before heading off for long days reporting at the Capitol, he records Punchbowl’s podcast The Daily Punch and often makes T.V. appearances in the mornings. “I leave when Congress leaves, oftentimes later than Congress leaves,” he said, though he insisted, “I get enough sleep.”

Sherman sees his direct daily contact with readers in politics as what sets him and his newsletters apart. “I’m talking to you now from the Capitol. I live in this building — not literally, but figuratively — and so does [Punchbowl co-founder] John Bresnahan. We exist among our readers,” he said. “Yesterday, after our morning newsletter went out, I had two or three members of Congress come up to me telling me they had an opinion about something I had written.” Punchbowl plans to take that intimacy a step further when they move into their new headquarters, a rowhouse blocks from the Capitol. “We’re going to do a ton of events, a ton of dinners, and cocktail parties,” Sherman said. “We’re going to have people who are subscribers into our offices.” Despite this projected comfort, Sherman was cautious about giving a detailed description of the building. “D.C.’s a small city, and I don’t want people showing up yet,” he said. “I don’t want people figuring out where it is.”

It makes sense that Punchbowl’s founders are investing in central D.C. real estate since that’s where they see their readers centering their lives. “We are really, really, really, really, really focused on the congressional leadership and the White House,” Sherman said. “If you’re somebody who works or operates in that sphere in D.C., our goal is to be indispensable to you.”

Elsewhere in the nation’s capital, Drew Steigerwald, the co-founder and editor in chief of the daily digest 1440, which claims over a million readers, is also an early riser. “I personally wake up at 4:30,” he said. But his imagined reader lives a world away. Whereas The New Yorker’s founding editor Harold Ross proclaimed that he wasn’t putting together his magazine “for the old lady from Dubuque,” Steigerwald continually brings up a mythical “accountant in Kansas City” as the archetypical 1440 reader. “There’s a lot of people outside places like D.C. and Chicago and New York and L.A., that actually do have this problem,” he said, “they’re not plugged into the D.C. culture or the hyper-localized New York media scene,” but they still want to know what’s going on, broadly, in the world. “You have a bunch of newsletters that focus on a specific topic, and they go very deep,” he said, “but there’s a lot of people that don’t need to know the on the ground situation in tech, politics, law, but they do need to know the 30,000-foot view across all of these different topics.”

In 2017, he and his co-founder, venture capitalist Tim Huelskamp, started their newsletter to provide precisely that. The vast majority of his newsletter’s copy is usually in by 9 p.m. the night before, and while Steigerwald sleeps, copy editors and a fact-checker dispersed across time zones work over it. In the early hours, Steigerwald scours the web for breaking news, fiddles with his subject line, and hits send. Though he’s lived in D.C. since 2012, Steigerwald grew up outside Columbus, Ohio. He went to Ohio State for college and moved to Nashville for grad school in material sciences at Vanderbilt before moving to D.C. to work on public policy. “When you grow up in the Midwest, you look at the coasts as almost like a different country,” he said. “You turn on the T.V., and you see people on the news: newscasters, famous people. Those people don’t exist in cities like Columbus. Even when I moved to Nashville, I’m not a country music fan, but it was pointed out to me like, ‘There’s Nicole Kidman and Garth Brooks’ — or whatever — ‘at the Whole Foods.’ When you grow up in the Midwest, you don’t see people who are on T.V. at your grocery store.”

That background is important because 1440’s audience is much closer, demographically, to midwestern purple states. “Our demographics are actually near the breakdown that you might see in a Gallup Poll,” Steigerwald said. “Roughly speaking, it’s one-third people who self identify as conservative or Republican, one-third who self identify as Democrat or left-leaning, and then a third, again, who self identify as independent. The reason I bring that up is if you look, just to pick on The Times, which, obviously, we have a ton of respect for, they have one of the greatest news infrastructures in the history of the world, but they have a very specific audience, right? It’s 90 percent, 95 percent left-leaning. They’re great, but we actually don’t feel like we compete with them because our audience isn’t the same. There’s overlap, but it’s not huge.” (A Pew Research survey found that 91 percent of readers who cited The Times as their primary source of political news identified as Democrats, though that doesn’t necessarily reflect the Times readership as a whole.)

Steigerwald was a regular reader of the Times Morning newsletter before Leonhardt, who won a Pulitzer for commentary in 2011, took it over and gave it a more personality-driven spin. “I’ll just give my hot take: I really liked the Times morning newsletter, and then they made a change, and I don’t like it. I don’t read it anymore. It’s just not useful,” he said. “The news email niche does have this utilitarian aspect to it where people are reading it because they’re on the train on the way to work or they’re sitting in traffic, right? The way The Times shifted the morning newsletter, it emphasizes his perspective, and I can get that anywhere at any time.”

1440’s approach is intentionally less personal. They pepper their newsletter with numbers and trumpet “impartiality” at every turn. “It’s about building a trust relationship,” Steigerwald said. “Our readers will actually ask us questions that weren’t in the daily email. It happens a handful of times a day. Just to pick an example, somebody emailed yesterday asking about the rate of breakthrough infections and deaths. It wasn’t like a gotcha question. It was more of a genuine thing. Like, ‘I’ve been hearing people in my social circle talk about how you can get the vaccine, but you still can get really sick. Do you have any idea what the data is?’ You can go find that data on the CDC website, but why would the average person? I mean, I do it for a living, and I have a science background, and it’s still difficult to find and parse through the data. So why would someone out in Indiana know to go find that on the CDC website?”

That connection with readers is what Steigerwald, like Sherman, sees as the main way to win over and keep groggy early-morning eyeballs. “I hear people talk about subject lines and whether you should put emojis in your subject lines and how many characters your subject line should be and should you put a joke at the top of your email,” he said. “All that’s fine, but I think if you’re talking about that stuff, you don’t have that relationship with your audience.”