The Sharp Pen

Building an Effective Newsletter Strategy with Dan Oshinsky

In this episode, I'm thrilled to bring you my conversation with Dan Oshinsky, founder of Inbox Collective. Dan's consultancy helps newsrooms, non-profits, and independent writers develop effective email strategies. He shares his fascinating journey from being the first newsletter editor at BuzzFeed to becoming a renowned newsletter consultant, offering valuable insights on building engaging newsletters and converting readers into paying supporters. Guest Introduction Today's guest is someone I've admired for a long time—and whose newsletter I always recommend. Dan Oshinsky is the founder of Inbox Collective, a consultancy that helps publishers, nonprofits, and independent writers grow their audience and turn emails into revenue. He previously led newsletter strategy at BuzzFeed and The New Yorker and has now helped hundreds of clients around the world build better email programs. I first met Dan at the Email Summit in Denmark in 2021, and I've been a devoted reader of his newsletter ever since. In this conversation, we get into the nuts and bolts of what it takes to succeed with newsletters in 2025—from strategy to content to growth—and where the email landscape is headed in a world shaped by AI. Dan, welcome to the podcast! Episode Highlights * Dan's Journey: How Dan accidentally became a newsletter consultant after working at BuzzFeed and The New Yorker * Newsletter Strategy Fundamentals: The importance of identifying your specific audience and understanding their needs * Content Development: Approaches to generating newsletter content ideas and different ways to structure them * Publishing Frequency: Finding the right cadence for your newsletter—daily, weekly, or monthly * Content Format Decisions: Whether to include full content in emails or drive traffic to your website * Email vs. Social Media: Why newsletters remain one of the most reliable marketing channels without algorithm interference * The Future of Newsletters: How AI might change email consumption patterns in the coming years * Independent Newsletter Business Models: The growing trend of journalists making a living through paid newsletter subscriptions Key Takeaways 1. Start with a specific audience: Know exactly who you're writing for and what their needs are 2. Content development: Create a list of topics based on audience needs and explore different ways to present them 3. Publishing frequency: It's easier to start with less frequent publishing and increase than to start daily and scale back 4. Measurement matters: Your business model should determine whether you keep content in emails or drive to your website 5. Email's advantage: Unlike social media, email gives you direct access to your audience without algorithmic limitations Resources Mentioned * Inbox Collective Newsletter [https://inboxcollective.com/newsletter/] * 52 Ways to Grow Your Email List [https://inboxcollective.com/ways-to-grow-your-newsletter-list/] The Sharp Pen * Newsletter [https://www.renehjetting.com/]