'LetterLand How to monetize a newsletter with events | ft. Ryan Sager of Who Sponsors Stuff
Jan 3, 2026
Ryan Sager, co-founder of Who Sponsors Stuff, brings his extensive media experience to discuss monetizing newsletters through live events. He reveals how he transitioned from editorial roles to leveraging newsletters for revenue. Ryan shares the success story of transforming intimate dinner gatherings into profitable conferences, emphasizing the importance of local sponsorship models over ticket sales. He highlights effective ways to validate event ideas and stresses the value of choosing operational speakers over celebrities for greater impact.
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Small Dinner Sparked A Community
- Ryan Sager started the Dine and Deliver dinners by inviting 24 newsletter practitioners to Pete's Tavern to create a safe, off-the-record space for deep discussions.
- The dinners grew into a recurring series with curated attendees, fostering ongoing connections and follow-up meetups.
Three-Group Cross-Pollination Works
- Ryan framed the industry as three groups: newsletter-native, traditional media, and creator media, and curated dinners to mix them.
- Cross-pollination between these groups produced valuable, practical learning for all sides.
Validate Dinners With Your List
- If you have a newsletter list with local concentration, promote a test dinner and collect RSVPs via a form before committing to a venue.
- Seek a sponsor to keep the event free for attendees and limit your initial spend to a small test budget.