Dan Oshinsky joins TJ Larkin to unpack what it really takes to build a sustainable newsletter business in 2025 and beyond. With over a decade of experience leading newsletter strategy at major media companies, Dan explains why newsletters are still early and where the biggest opportunities exist today.
The discussion covers niche selection, local newsletters, audience trust, and how creators can combine newsletters with social media, events, and community building. Dan shares real examples of newsletter operators who turned small audiences into six-figure businesses by focusing on value, consistency, and relationships.
If you’re struggling with ad sales or unsure how to monetize your newsletter, this episode offers practical advice on building partnerships, following up with advertisers, and creating long-term revenue instead of chasing quick wins.
Guest: Dan Oshinsky
Website & Newsletter: https://inboxcollective.com/
Newsletter Advertising Playbook: https://inboxcollective.com/buy-the-playbook
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#Newsletters
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