Dan Oshinsky knows newsletters better than most. He’s been focused on the medium for a decade and a half, first at Buzzfeed, then The New Yorker, and now as a consultant.
We’re big fans of his work (he publishes some of the best newsletter advice and guides on the web); this feature has been a long time coming.
In this episode:
— Natalia Pérez-González, Assistant Editor
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Over a decade in the inbox
When Dan Oshinsky started running newsletters at BuzzFeed back in 2012, he called around to The New York Times, The Wall Street Journal, and The Washington Post, looking to compare notes with anyone in a similar role.
He kept getting a version of the same response — why would you spend your time on newsletters?
A few months later, he set out to write a roundup of 14 newsletters worth subscribing to. Finding 14 truly worthwhile products was difficult. By 2019, when a magazine asked him to name the 100 best newsletters, he filled the list with titles to spare. Ask him to do it today, and it’d be a true challenge to whittle the selection down.
Few people have had such a close view as the newsletter business has evolved into what it is today. After his stint at BuzzFeed, Dan went on to lead newsletter strategy at The New Yorker.
In the spring of 2019, a recruiter called Dan with what looked like the obvious next career move: a bigger title and the highest salary he'd ever been offered. Twenty minutes into the interview, he realized he wanted the opposite. He walked away, launched Inbox Collective that July, and built its first website out of six Google Slides.
Dan runs Inbox Collective as two operations under one name:
The consulting side rebuilds email programs for newsrooms and nonprofits — Boulder Reporting Lab, the Anchorage Daily News, the Leakey Foundation — working the same three problems in rotation: get readers in the door, keep them, convert them into subscribers, members, or donors.
The other half is the website, a free library of case studies and how-tos on nearly every part of running a newsletter. The second feeds the first; he's never sent a cold pitch to a client.
Dan just relaunched the Inbox Collective site, optimizing around specific learning tracks.
Teams often reach out to hire Dan early on, but he redirects them to his free launch-and-grow guide first, and to come back in a year with harder problems. If something isn't clear, he'll rewrite the guide. Clients show up anyway, usually already convinced.
Dan has been present for many eras of the internet newsletter industry; when he forecasts the next change, people listen. Here’s the narrative he sees:
In the early 2010s, a newsletter was a pipe back to your website; writers asked him for one the way they'd ask for traffic.
By mid-decade, publishers realized email converted readers into paying subscribers better than anything else, and voice and design started to matter.
Then came the creator era, when email became the main destination (as opposed to publisher websites).
Next, Dan believes, is loyalty — with pressure increasing for publishers to prove value anew on every send.
"There aren't too many newsletters; there are too many bad newsletters […] Those newsletters that are kind of in that middle ground, they're not really succeeding, they're not making enough money, they're not growing, and people don't love them. A lot of those products are gonna be kind of slowly forced out by AI."
What survives, he says, is depth — of curation, analysis, expertise, access. The newsletters that report something nobody else has.
Subscribe to Inbox Collective.
Connect with Dan on LinkedIn.
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An algorithm is moving into your inbox
Dan has been telling clients and followers that email is on the verge of its biggest structural shift since the smartphone. For three decades, email’s defining feature has been that the reader controls what lands in their inbox; with proliferating AI features, though, the reader will no longer be the main gatekeeper.
The average person has over 1,000 unread emails (I’m driving up the average with 3,758 in my personal inbox). Every week, handfuls of newsletters we once eagerly subscribed to continue arriving, never to be read — small reminders of the readers we imagined ourselves to be.
The AI inbox features shipping today — summaries, rewritten preview text, inbox assistants — Dan frames as incremental but indicative.
Screenshot from Google’s “Gmail in the Gemini era” video from January 2026.
Instead of asking readers to sort through hundreds of emails themselves, AI systems will decide what deserves attention, what can wait, what can be answered automatically, and what never needs to be seen at all.
"I open my email at 5 p.m. on a Thursday, and there's a report that says, by the way, Dan, here are the things that you need to deal with right now. We flagged these emails as ones that you need to handle and respond to, these emails that you want to read. And we went ahead and got rid of some stuff that you didn't really need."
This raises a new challenge for publishers. Today's inbox still faithfully delivers the newsletter you enthusiastically subscribed to six months ago, even if you've quietly stopped opening it, but tomorrow's inbox may not.
AI will track and learn from your repeated behaviors, and though those newsletters won't necessarily disappear, they may stop earning a place in front of you.
He uses the nightclub as a metaphor: Plenty of people can get in, but the inbox becomes the VIP room behind the velvet rope. Integrated AI features play bouncer, judging every newsletter issue anew; collecting an email address might not assure delivery anymore.
"Once I get into the inbox, that's not the end of the relationship. That's the start of the relationship. That's where I have to figure out how I build loyalty, how I provide value, how I deliver an exceptional product every time."
A few notes on newsletter strategy ✍️
Dan has two questions he asks every new client:
What do we have access to that nobody else does?
How do we build a product around that instead of around our existing content?
The Leakey Foundation, for example, looked like countless nonprofit newsletters: a couple of recent blog posts, a field update, and a donation ask. It reached a small circle of existing supporters and went little further.
Dan realized the foundation’s biggest asset was its access; Leakey funds researchers and university professors studying human evolution, many of whom got their start through the foundation and will happily pick up the phone. He's now helping turn that network into a standalone publication that explains human behavior through evolution and animal science.
Rather than using the newsletter to promote the organization, the newsletter becomes the product, and the foundation becomes the thing readers discover second.
Flex your voice and tone in unexpected places. Dan points to The Onion, where the membership page, purchase receipt, and welcome emails are all unmistakably funny.
Even the member gift — an InfoWars tote in rainbow colors, a nod to The Onion's (complicated) acquisition of Alex Jones' media company — the tote extends the joke into the real world, sparking conversations in grocery store checkout lines. Most organizations treat these touchpoints as administrative, but they're actually some of the best places to reinforce your brand. In a crowded inbox, voice and tone differentiation is key.
Collect the data readers willingly give you, then build around it. Dan says it is his professional mission to kill the phrase "e-blast." Instead of treating every subscriber the same, ask what they care about — whether they're a voter, parent, volunteer, or something else — and trigger automations from those answers. A subscriber who's told you exactly what they want and still hasn't paid (or taken another desired action) is one of the highest-intent prospects you'll ever have.
Read Dan on all the details a newsletter operator might A/B test.
Only A/B test when the outcome matters. While you're finding your voice, experiment freely. Once you've settled into a rhythm, Dan says, stop obsessing over subject lines. At 10,000 or 25,000 subscribers, squeezing out another point of open rate rarely changes the business, and you'll send another newsletter tomorrow. Save the testing for launches — courses, products, paid subscriptions —where even a small lift translates into real revenue.
