Beyond Your Town: How to Scale Local Newsletters into Regional Media Networks

Starting a hyper-local newsletter is one thing. Turning it into a sustainable business is quite another challenge.

Kyle Scott discovered this firsthand after launching "Walking the Boards," a newsletter covering Ocean City, New Jersey that grew to an impressive 17,000 subscribers. While his subscriber base was thriving, the business model presented a common dilemma for solo newsletter operators.

When your newsletter reaches thousands of engaged local readers, you essentially face three paths:

Kyle discovered that path #2—trying to make a full living from a single local newsletter through direct advertising—presented significant challenges.

"It's very difficult because ultimately it's about community, right? Unless you're willing to kind of just make this your entire life, you're going to have to piece together 500 to $2,500 individual ad deals with dozens of advertisers," Kyle explains.

Anyone who's tried to monetize through local advertising knows the grind. You're not just writing a newsletter—you're becoming a full-time ad sales representative, account manager, and collections department.

Kyle experienced this firsthand years earlier with his sports website: "I lived this for three, four years when I started my sports website 12-15 years ago. I had $800 advertisers, and I had to go host quizzes twice a month at their bar."

The administrative burden quickly becomes overwhelming. "You find you're spending like 80% of your time for 20% of the revenue. And then that's where it just becomes difficult to sustain over time."

Rather than continuing solo, Kyle found a different approach. When a company building local media sites around Philadelphia approached him about acquiring his newsletter, he saw an opportunity to solve the business model problem.

"They said, 'Hey, we really need to crack newsletters. Would you want to roll yours into our company and then use Walking the Boards as a model for these other dozen websites we have in the Philly and South Jersey area?'"

This regional approach created several immediate advantages:

While a single town's audience might be too small for major advertisers, combining multiple community newsletters creates regional reach that attracts bigger budgets.

"Instead of trying to sell ads to maybe the local pizza shop or the local HVAC place, we could tap into regional advertisers—the hospital systems," Kyle notes. "We're able to aggregate the audience and bring it to advertisers. It's more appealing than just having to go to the local companies that typically don't have the big ad budgets."

Running everything yourself means you're constantly switching between content creation, sales, technical issues, and community engagement. A regional network allows for specialized roles.

The company Kyle joined already had a sales team and editorial staff, allowing each person to focus on what they do best rather than wear a dozen different hats.

Each local market provides lessons that can be applied to others. Kyle spent six to seven months training the team on newsletter best practices: "Here's how you kind of spin these newsletters up. Here's the content format."

This knowledge sharing accelerated the growth of new newsletters across the network.

The impact of regional scale became immediately apparent. While single-town newsletters might struggle to attract advertisers beyond local mom-and-pop shops, Kyle's regional network landed major clients.

"One of the brands the company works with is Parx Casino, which is the biggest casino in Pennsylvania. They're the type of advertiser you'll see on local TV, and they have five, six-figure ad budgets for different mediums."

These are advertisers that would never consider a single local newsletter but eagerly partner with a network reaching 50,000-70,000 subscribers across a cohesive region.

If you're considering scaling beyond a single newsletter, Kyle's experience suggests a strategic approach:

The regional network approach isn't necessary for everyone. If you're running a newsletter as a side project or marketing channel for another business, staying focused on a single community makes perfect sense.

However, if you're trying to build a standalone media business, the economics often push toward expansion. The 80/20 rule applies perfectly here: "A good media business lets you spend 20% of your time on sales but throws off 80% of the revenue," Kyle explains.

That balance becomes much more achievable at a regional scale than with a single hyper-local property.

The next frontier for regional newsletter networks isn't just more locations—it's deeper engagement across communities. Kyle sees tremendous potential in bringing these digital audiences together through events and other in-person experiences.

"I'm super bullish on the interactive part of newsletters. If you use them on a local basis to hold IRL events—huge deal, huge differentiator."

While AI and aggregation tools can replicate basic local information, they can't replace authentic community connections. That human element remains the competitive advantage that no algorithm can match.

For local newsletter operators facing the fork in the road, expanding horizontally might just be the path to sustainable growth—without sacrificing the community connections that made your first newsletter successful.

Before we dive into this week's insights, I want to make sure you know about all the resources available to support your local newsletter journey:

🎙️ The Podcast - Deep-dive conversations with successful newsletter operators sharing their playbooks and lessons learned | Link

📧 This Weekly Newsletter - Quick, actionable tips delivered straight to your inbox every week | Link

🧠 1:1 Consulting - Personalized guidance tailored to your specific newsletter challenges Link

🚀 Launch Accelerator - A structured program to help you go from idea to profitable newsletter in record time | Link

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