There’s no shortage of newsletters out there. Nearly every publication has one these days, as do an army of high-profile writers. True, the medium’s shine has worn off a bit, but curious readers can still easily pick between thousands of missives on everything from finance to Final Fantasy.
Even in such a saturated market, The Flip Side manages to stand out. That’s because, in an era of partisanship and hyperbole, the newsletter takes a decidedly more nuanced tact: Rather than using the format to opine on a political issue, The Flip Side simply offers readers an aggregation of right- and left-leaning perspectives. “We’re hoping to become the next generation platform for news and debate,” says cofounder Annafi Wahed, “given that the last 20 years in digital media have not been the greatest for substantive discussions.”
The idea for the newsletter first came to Wahed in late 2016, after she’d spent five months in New Hampshire working as a field organizer for the Democratic Party. Donald Trump’s upset win that year prompted a deep dive into conservative media. She started sending out email blasts to a small group of leftist friends with articles and video clips she thought might help them to better understand the conservative mindset. At her friends’ suggestion, she then scoured Facebook and LinkedIn for Republicans who might want to hash out their ideological differences. That brought her to Jihan Varisco, then a recent graduate of the University of Chicago’s Harris School of Public Policy.
Varisco himself was no stranger to the decisive nature of politics. While in school, he once hosted an “ask a conservative” event; at the end, an attendee offered her praise for the sit-down and said it had never occurred to her that conservatives’ beliefs might in fact be grounded in reason. “That was really eye-opening in a way,” Varisco says.
Wahed and Varisco connected and, sure enough, argued about all sorts of issues. But they also learned from each other. “We thought, ‘Facebook and Twitter show you the worst of both sides,’” Wahed recalls. “‘What if there was a place where that showed you the best of both sides?’” Using Mailchimp, in 2017, the duo created a newsletter that does just that: Every weekday, subscribers receive a fresh edition that curates, in adjacent columns, commentary around a single topic from leading voices on the right and the left. (Their logo, a bookish-looking bear, is “large but multifaceted,” Wahed says, just like the body politic.) Seven years later, The Flip Side has amassed over 200,000 subscribers, as well as a new premium tier that features a community forum and has already netted 5,000 paid subscribers.
The review process is tedious, given it’s just Varisco, Wahed, and a few contributors reviewing articles for inclusion in each edition of The Flip Side. Basically, they hop onto Slack every day and settle on a subject, which could range from an impeachment inquiry to a contentious piece of legislation. Then, they unload an avalanche of published opinion pieces (with an emphasis placed on author credibility and publication reputability) onto a shared Google Doc. Finally, they carefully comb through each article, scrutinizing the analysis and giving a cursory fact check to their final selections (usually between six and eight sources).
For both Varisco and Wahed, that means engaging with arguments they might find tiresome, if not loathsome. Varisco credits Vox’s Ian Millhiser as a left-leaning journalist whose opinion he respects, if disagrees with, and Wahed cites right-wing writer Andrew McCarthy at National Review.
The end result is something that gets past the typical pundit talking points. Take the Supreme Court’s recent ruling to overturn Chevron, which limited federal agencies’ power to interpret the laws they administer and instead returned that power to the judiciary. Readers of The Flip Side were told on the one hand that “there’s simply no reason to think that some guy with a juris doctorate and a judicial commission will know how to handle these questions” (that’s Vox’s Millhiser); and on the other that the original Chevron ruling “enabled agencies to aggrandize their own powers to the greatest extent plausible” and thus had to go (that opinion comes courtesy of right-wing academic Ilya Shapiro in City Journal).
Reading through the litany of opinions on display, readers are left with a messy, at times contradictory understanding of the issue. That’s a tough business proposition given Americans’ historically low trust in the media and our ever-heightening state of polarization. But, despite an approach that seems diametrically opposed to social platforms’ engagement-over-everything philosophy, The Flip Side’s audience has indeed grown at a steady clip, and Wahed and Varisco recently made their first hire in chief technology officer Matt Harris. It’s Harris who’s responsible for the inchoate community forum, which deploys an upvote system not unlike Reddit’s in order to incentivize respectful discourse among users. “If there’s too much bias on one side, it pushes you down a little bit, so that we get that more equal representation,” Harris explains.
The Flip Side certainly hasn’t lacked for material in an election year that’s seen an assassination attempt on Donald Trump and the sudden ascendance of Kamala Harris as the presumptive Democratic nominee. In the case of the shooting at Trump’s Pennsylvania rally, The Flip Side team’s job is, on its face, a little simpler, as every major publisher condemned the violence. But again, the devil is in the details.
“Even after years of reading each other’s work, Jahan still asked, ‘Oh, so both sides agreed that the Democrats need to tone down their language, right?’” Wahed recalls. “And I was like, “No, the Democrats are not saying that.” Ultimately, they landed on an edition that acknowledged at the top of the newsletter that, yes, both sides tend to agree we need to lower the rhetorical temperature, before breaking down how each side claims the other is the real culprit when it comes to linguistic overreach.
To date, The Flip Side has raised about $900,000 through angel investors and paid subscriptions. In order to keep scaling their project, Wahed knows they’ll need a proper Series A. To her, the pitch to the powers that be is a simple one: “We are making the bet that as Facebook and Threads and X fill up with AI bots and spam, that [a] path for substantive discussions will become even more desperately needed,” she says. “And that’s what we tried to do with our newsletter: proactively build a pro-social, pro-democracy, pro-bipartisan platform.”