Writer on the Side 168 Running 3 Newsletters on the Side - Small Bets Discussion
10 snips
Jun 12, 2025 
Daniel Vassallo, the mastermind behind Small Bets, shares insights on managing three distinct newsletters while juggling a full-time job and family life. He discusses the growing importance of newsletters as a revenue-generating tool, providing practical tips on integrating ads effectively. Vassallo outlines strategies for maintaining subscriber engagement and the nuances of monetization using platforms like Beehive. The conversation also touches on common pitfalls in newsletter publishing and the evolving landscape of online education, showcasing how adaptability is key for success.
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Hasan's Ad Resistance Story
- Hasan Osman shares how he initially resisted ads, feeling they interrupt social connections.
- Advertising on Amazon felt natural since people there are already in buying mode, easing his reluctance.
Value of Owning Your Audience
- Owning your email list means direct audience access unaffected by social media algorithms.
- Newsletters allow repurposing content and leveraging AI to reduce effort while providing consistent value.
Maintain Content to Ad Ratio
- Include a clear, dedicated ad section in newsletters with a good content-to-ad ratio.
- Maintain a 3:1 or 4:1 ratio to keep subscribers engaged and accepting of promotional content.