How Six-figure Newsletters Are Built

TJ's musings

Hi local media operators,

Great episode featured today with Dan Oshinsky. He’s one of the smartest guys in the entire space. He’s been working in newsletters since 2012! Yes, that’s four years before Morning Brew launched.

You absolutely need to hear him talk about how he has multiple local newsletter clients making six figures quietly. And, his take on going one niche deeper. I couldn’t agree more!

And if you didn’t see last week, our ai-first newsletter builder lightbreak (lightbreak.ai) is now live! Getting insanely positive feedback so far. You can see Shane build a newsletter live on the site, so check it out. And book a demo with him if you think it’s a good fit.

Podcast spotlight

Dan Oshinsky on The Power Of Niche Newsletter Audiences

Top Three Takeaways

Turn Handshakes into Contracts

Legacy outlets profit because they already know every merchant in town; independents must build that same rapport.

• Build a master spreadsheet of every company buying radio, billboard, print or bus-stop ads; those budgets are proven.
• In-person beats inbox: chamber breakfasts, door-knocks and persistent follow-ups convert “busy” into “buying.”

Grow One List into a Local Media Stack

Your newsletter is the seed; real upside comes when you bolt on podcasts, events and niche spinoffs.

• Charlotte Ledger grew a single email into multiple beats, live galas such as “40 Over 40” and a six-figure sponsor roster.
• Extra channels let you upsell the same advertiser on newsletters, whitepapers and room-filling soirées.

Mine Micro-Niches for Macro Profits

Big horizontal topics are crowded; pairing newsletters with laser-specific audiences unlocks green fields.

• Think “Morning Brew for Canadian dentists” or “local news plus yoga moms”; these tiny TAMs deliver hefty wallet share.
• No-code platforms (Beehive, Substack, Ghost) mean curiosity and consistency now outrank a Journalism school degree.

Growing a Local Newsletter Without Relying on Meta Ads

Growing local media doesn't have to mean being a slave to the Facebook algorithm. Matt Moody proved this with his local media brand in Kansas by using social platforms for distribution while keeping the real goods behind an email wall. He leaned hard into local photo galleries because, let's be real, everyone wants to see pictures of their kids or their friends at the game.

How a Local Newsletter Became a $100k Business

Great episode to check out about someone crushing on the content and sales side of local media.

Marissa Lovell is a total powerhouse in the local media space. She managed to turn a massive cash flow crisis into a $100k revenue stream by hiring a dedicated salesperson and staying the face of her brand through 23,000 signups. Definitely worth a watch for any founder.

Great reads

What 2025 Revealed About Running a Newsletter

After watching this space for years, I still find it fascinating how the rules of email keep shifting. Newsletters are not static. We are learning new norms around growth, AI, monetization, and what actually keeps a reader engaged. If you want to stay relevant in the inbox in 2026, this one’s worth a read.

Read it HERE.

Journalism Schools Are Finally Embracing the Creator Economy

One of the biggest gaps in local media has been how unprepared new journalists are for the business side of the work. This caught my attention because it signals a quiet but important change. Journalism schools are moving beyond the idea that great reporting sells itself. Teaching creators how to grow, distribute, and sustain their work feels like a much more honest version of media education.

Read it HERE.

Local Media is Now a Personal Brand Game

There’s a massive "trust tax" coming for everyone who publishes online, and local media is right in the crosshairs. As AI slop floods the internet, people are developing a kind of "stranger danger" for any content they don't already recognize. This is why the old-school, faceless institutional voice is a death trap and the era of the mystery reporter is over. You have to show up, be seen, and build a personal brand that people can actually vouch for.

Read it HERE.