How Dan Oshinsky used his popular newsletter to grow his consulting business
Dan's growing archive of case studies and advice articles have turned his website into a go-to resource for newsletter operators.
As platform-driven traffic continues to erode, media operators have increasingly shifted their focus toward owned audiences—especially newsletters. But while many publishers have embraced email as a distribution channel, far fewer have fully leveraged all of the medium’s capabilities.
That gap has created a new class of operator: the newsletter specialist. And few have built a more effective model around that expertise than Dan Oshinsky.
After leading newsletter strategy at major publications like BuzzFeed and The New Yorker, Oshinsky struck out on his own to launch Inbox Collective, a consultancy focused entirely on helping editorial organizations grow and monetize their email products. What’s notable isn’t just the demand for his services—it’s how he built the pipeline.
Rather than relying on outbound sales or traditional marketing, Oshinsky has spent the past five years publishing a steady stream of content about newsletters. That content—first as a quirky Google Doc, later as a full-fledged media property—has become the primary engine driving his consulting business.
The result is a model that flips the traditional consulting funnel on its head: instead of pitching clients, Oshinsky teaches in public and lets the clients come to him.
In a recent interview, Oshinksy walked through his content strategy and explained how the hundreds of articles he’s published contributed to growing his consulting business.
Let’s jump into it…
Background: An Accidental Consultant
Oshinsky didn’t set out to build a consulting business. In fact, when he launched his first content project in early 2019, he was still working full-time at The New Yorker.
The project, called Not a Newsletter, was exactly what it sounded like: a living Google Doc where he curated links, ideas, and insights about the email space. It was born out of a simple, recurring question he kept getting from peers in the industry: What are you reading to stay sharp on newsletters?
“There’s a lot of blogs out there,” he recalls thinking, “but it doesn’t always apply to what we’re doing.” So he created his own resource—a one-stop shop for editorial-focused newsletter insights.
He didn’t expect much traction. “If I get 10 people, I’ll do another one,” he remembers telling his wife.
Instead, 400 people signed up within three days.
That early response revealed something important: there was a clear, underserved demand for high-quality, editorial-focused thinking about newsletters. At the time, most email advice came from marketing platforms like Mailchimp or HubSpot—useful, but often disconnected from the needs of newsroom operators.
Oshinsky’s content filled that gap. And just as importantly, it gave him a visible presence in a niche where few others were publishing consistently.
That visibility quickly translated into opportunity.
The First Inflection Point: Demand Without a Business Model
As Not a Newsletter grew, Oshinsky began receiving a steady stream of inbound inquiries. Editors and publishers would reach out asking for recommendations: Who should we hire to improve our email strategy?
At first, he didn’t know how to respond. “I kept going back to my wife and saying, I keep getting these emails and I don’t know who to introduce them to,” he says.
Her answer reframed everything: “They’re asking for you.”
That realization forced a decision. Stay at The New Yorker, or step into an undefined, somewhat intimidating role as an independent consultant.
What ultimately pushed him toward the latter wasn’t certainty—it was the opposite. “I liked the idea that I didn’t know how it was going to play out,” he says. “Every once in a while, it’s nice to try something where you go, I just don’t know if this is going to work.”
Before fully committing, Oshinsky ran a simple but highly strategic experiment. He emailed his growing list—then around 1,700 subscribers—and offered to talk to anyone who wanted to chat about their newsletter challenges.
That summer, he held more than 70 calls.
Those conversations served three critical functions. They validated demand, surfaced common pain points, and helped him design an offering that matched the realities of his target customers—especially smaller newsrooms with limited budgets.
Key Strategic Shift: Productizing Consulting for Smaller Clients
One of the clearest insights from those early conversations was that many organizations couldn’t afford traditional consulting engagements.
“They want tens of thousands of dollars,” Oshinsky recalls hearing, “and we don’t have that kind of budget.”
At the same time, he had been warned by other consultants about the feast-or-famine nature of the business—long stretches between large projects with no income.
His solution addressed both problems at once: a coaching model built around recurring, lower-cost engagements.
Instead of charging large upfront fees, Oshinsky began offering monthly coaching calls to a cohort of clients. Each engagement typically ran for a year, with a fixed cadence and a clear roadmap of topics to cover—from welcome series to monetization strategies to audience surveys.
The structure was deliberately lightweight. Clients didn’t need to prepare extensive materials, and Oshinsky wasn’t embedded in their day-to-day operations. Instead, he focused on delivering high-leverage guidance in focused sessions.
“It’s a little of my time, a lot of my expertise,” he explains.
Crucially, this model allowed him to scale his knowledge across dozens of clients simultaneously. The same slide deck or framework—say, for an end-of-year fundraising campaign—could be reused across multiple organizations with similar needs.
Over time, coaching became a stable, recurring revenue stream—“essentially my version of a membership,” he says.
Alongside coaching, he layered in higher-ticket services like audits and retainers, creating a tiered offering that could serve clients at different levels of complexity and budget.