When The New York Times first broke the news that Vox Media was acquiring New York magazine last night, the most common reaction online was to the photo — one that made it look as if CEOs Jim Bankoff and Pamela Wasserstein were a bright young couple, maybe post-residency MDs nesting in Westchester, having their upcoming nuptials recorded in the Times’ Vows section.

The latest vows column is a whopper. https://t.co/8TpFYff0J8

— Laura June (@laura_june) September 25, 2019

The photo made me think they got married? Which I guess they kinda did? It’s super Vows-looking. Congratulations. https://t.co/GaUMezD3XE

— Lisa Tozzi (@lisatozzi) September 25, 2019

Congratulations to @Vox and @NYMag on their wedding, tastefully chronicled in the NYT Vows section oh wait https://t.co/HrwRIniqPe

— Christine Emba (@ChristineEmba) September 25, 2019

Looks like a photo for a Vows column. 👀🔛👀 https://t.co/ehuoupcjdh

— katie rosman (@katierosman) September 25, 2019

(That reaction is a not-so-subtle reminder of how unusual it still is to see a 41-year-old woman leading the sort of high-profile company whose acquisition would be deemed worth a business-section story.)

Vox Media is, of course, one of the largest and most successful digital-native publishers, the autocomplete that pops up if you type “buzzfeed vice” anywhere on the Internet. Built out of sports site SB Nation and later expanded to include The Verge, Vox, Eater, and more, Vox Media has historically thought of itself as the Condé Nast of the Internet: a collection of premium, subject-specific media brands that can do high-gloss editorial and attract high-end audiences, but with the technology and product chops that come from growing up online. It’s the most print-like of the big digitals; you can see the DNA of magazine layout in some of its designs, and its mix of both editorial big swings and webbier front-of-book content brings along some print editorial values.

New York is, of course, the storied magazine that grew out of the late New York Herald Tribune under the guidance of editorial legend Clay Felker. It’s a city magazine in name and attitude. But like its peers at The New Yorker and The New York Times — it both reflects New York and uses it as a jumping-off point for writing smartly about anything and everything. And like the Times and New Yorker, that has given it the ability to adapt its identity to the Internet in ways most local print outlets can’t. Under the editorial leadership of Adam Moss, it launched a series of digital editorial brands with no explicit connection to New York but which took advantage of the magazine’s strengths — most notably the culture site Vulture and the fashion/style site The Cut, which for my money is the smartest “women’s” site online. (Its readers’ median household income? $186,797.) As long ago as 2010, David Carr could describe New York as “fast becoming a digital enterprise with a magazine attached.” It’s probably the webbiest of the major print-born media companies.

So the most print-like digital publisher is joining up with the most digital of print publishers. While this is being framed as an acquisition (with no dollar amounts released), it’s not hard to see why it might look like…a happy marriage. Substantial audience overlap, similar editorial values, strong reputations for quality — these crazy kids might pull it off!

You can see how the two sides are framing the meet-cute here (with a photo that even meets the Vows rule about even eye levels):

We have long admired (and often envied) each other’s businesses, which revealed themselves to be uniquely complementary as we quickly moved from exploratory conversations, through diligence, to an agreement. Sharing values, we found our capabilities — each excelling in different areas, with little overlap — naturally and seamlessly fitting together. New York Media is an exemplar of groundbreaking journalism, with a smart, trenchant voice, that has turned a 51-year-old print magazine into an inventive multiplatform company that punches well above its weight. Vox Media’s authority, spirit of innovation, and foundation in technology and communities, together with its visionary approach to expansion, diversification, and growth, have set it apart from other media companies that have risen in the past decade.

Let’s take a look at this pairing — what works and what might not.

Scale without culture clash? The talk of the industry for the past several years is that the biggest digital publishers need moar scale. BuzzFeed CEO Jonah Peretti said it out loud nearly a year ago, arguing that the ongoing structural problems in online advertising should push companies to merge into some giant BuzzVoxViceNine29Corp. “Everyone’s for sale.” But corporate mergers rarely work perfectly and often don’t work at all. And despite the fact that BuzzFeed, Vice, and Vox Media are all in the same broadly defined business, they each have their own corporate and editorial cultures, and it’s not clear how they’d mix. Even though New York Media was born of another medium, I’d wager that Vox Media aligns better with its culture than it would Vice’s or BuzzFeed’s.

Overlap in approach, but not in verticals. Given that the same few verticals seem to pop up across media companies — everybody gets a tech site! — it’s remarkable how little content overlap these two companies bring. New York doesn’t do sports like SB Nation; Vox Media doesn’t do entertainment like Vulture. Vox.com and New York’s Intelligencer both cover politics, but in complementary ways. There’s some overlap in tech and fashion/style, but less since New York stepped back from Select All and Vox Media folded Racked. The fact that the merger will apparently not be accompanied by editorial layoffs (“Nothing changes editorially for any of our brands”) is both rare and evidence of that complementarity.

(Update: Brad Skillman points out one narrow editorial overlap I missed: New York’s Grub Street covers NYC restaurants, as does the NYC subsite of Vox Media’s Eater. But New York is only one of Eater’s 24 markets.)

That’s mostly true at the product and revenue levels too. Vox Media is interested, like everyone else, in e-commerce revenue, but it doesn’t have a purpose-built shopping recommendation site like The Strategist. Both companies generate revenue from events, through Recode’s high-end experience is probably the most valuable. Vulture writes about podcasts a ton (thanks in part to our own Nick Quah), but Vox Media has a more built-out actual network of podcasts — over 170 of them, heavy on sports.

Indeed, there are a lot of elements where the larger Vox Media plugs holes in New York. New York has no ad marketplace like Concert and no studio like Vox Creative. Vox also has a ton more experience producing video for streaming services and for YouTube (though New York did launch an effort there on Monday) — plus a deep bench of tech and product talent.

(It is worth noting that a “no editorial layoffs” pledge doesn’t mean there won’t significant, er, efficiencies gained from merging the teams doing ad sales, marketing, tech, and the like. There will be, at some point.)

CMS FIGHT!!!!!! There is one important area of significant overlap, in CMS/publishing platforms. Vox has poured major resources into Chorus, which it now licenses to publishers both old and new. New York, meanwhile, has built Clay (as in Felker), which aims to solve a lot of the same problems in a more modular way, and which has also become a licensing business (Slate, Golf.com) despite being open source at its core.

One imagines two rival teams of developers, meeting in a field somewhere outside the Meadowlands, ready to battle to the death over whose philosophical choices about article metadata will live to see tomorrow. (“Get that Redis isht out of here!” “Node.js is the one true run-time environment!” “Ruby on Rails all day! ALL DAY!”)

I’d put good money on Chorus winning out, based on Vox Media’s past history with acquisitions and just common sense, but perhaps Clay or some of its underlying components will find a way to live on in some form. (It is on GitHub, after all.)

There is one other critical area of overlap: crossword puzzles. As of a week or so ago, they both have them. Picture that same field outside the Meadowlands, but two teams of logophiles doing damage with pencils, or pens when they’re feeling confident.

Distinct paywall models. Just like everyone else, both companies are chasing direct revenue from readers, but they’ve had different approaches. Vox Media has been relatively cautious, experimenting with things like the Vox Video Lab. Bankoff said this spring there would be some further membership/paywall moves “later this year.”

Meanwhile, New York went all-in on a metered paywall late last year, at $5 a month. Interestingly, it’s a subscription that cuts across all of New York’s verticals — even though there are dedicated Vulture readers who have no interest in The Cut, Grub Street partisans with no time for Intelligencer, and so on.

I enjoy a lot of New York content, but I confess I haven’t ponied up those five bucks. As I wrote last year, it’s harder for magazine and magazine-like digital properties to make a subscription pitch, given that they are often a news consumer’s second read after the Times, the Post, or some other more full-service publisher. But a subscription that includes not only those New York sites…but also Vox, The Verge, SB Nation, et cetera? That’s a stronger pitch, even if it means divvying up the money among more sites. (Wasserstein said today that one of the areas of “new potential” she’s most interested in is “subscription businesses across this entire portfolio.”)

Think for a minute of the nascent streaming wars — Netflix, Amazon Prime, and Hulu being joined by Apple TV+, Disney+, Peacock, HBO Max, ad infinitum. Knowing that consumers are unlikely to pay for lots of individual channels piecemeal, each company is trying to recreate the old cable bundle in its own way. (Are Marvel movies not enough to get you to sign up for Disney+? Well then, how about Toy Story? Or The Simpsons? National Geographic? Frozen? Yoda? Do you like Yoda? You seem like someone who’d like Yoda. What if we threw in ESPN+ and Hulu too?) They know that, given the sea of free content available and the incumbents’ advantage, it’ll take a diverse catalog of content to get people to pony up for access to the whole package.

When the digital publishing business was mostly about advertising, the purpose of moar scale was primarily about cutting backend costs and being able to do deals with a higher grade of advertiser. But as it shifts more toward subscription, moar scale is also about assembling a big-enough and diverse-enough bundle of content to appeal to a bigger audience. Sites have gotten pretty good at getting their superfans to buy a digital subscription. But there aren’t enough superfans. Yes, there are people who loooooooove The Cut. But there are probably more who only like The Cut — and also like Vox and The Verge and Vulture.

That’s an opportunity mergers like this can provide. This is a critical distinction from the print-era Condé Nast, where a Vogue subscriber had no reason to care that the same company published Golf Digest and GQ. Magazine-style content, but newspaper-style bundle.

(Side note: Vox Media and New York were two of only a handful of digital publishers who agreed to be part of the premium Apple News Plus bundle, in which they get some infinitesimal cut of Apple’s subscription revenue. Better to build the bundle than to be bundled by someone else.)

I like this deal. I like both companies involved and how they fit together. I like that there’s a legitimate growth story to be told, not just a cut-until-you-hit-profit one — which is the narrative most American newspapers are facing, unfortunately.

I’m sure roadblocks will pop up along the way, at all levels of the new operation. But I think these two have a real shot at making it work — maybe even growing old together. And the kids will probably be cute.