Scaling Local Media Beyond Newsletters

In this episode, TJ sits down again with Jas from Winnipeg Digest to talk about the latest experiments and strategies in local newsletter publishing. They discuss the upcoming Business of Local conference in Salt Lake City, the pros and cons of cash giveaways, and the importance of building trust with your audience instead of chasing vanity metrics.

Jas shares updates on his community-building efforts, from coffee parties to launching Digest Lights, a holiday lights installation business born out of his newsletter audience. He explains how a giveaway generated hundreds of qualified leads, his sales process for closing $2,500+ projects, and why retention in seasonal services is so valuable.

The conversation also dives into social media strategy, comparing reels and carousels, outbound ad sales systems, and welcome email sequences that actually drive engagement. Whether you’re running a newsletter or exploring new business ideas, this episode is packed with practical lessons from the trenches.

Connect with Jas on Twitter: https://twitter.com/jas

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