Starting a local newsletter might not make you rich overnight—but if you play it right, it can transform your life and business. That’s the clear takeaway from a wide-ranging conversation between TJ Larkin and Trenton Hughes, co-founder of Wilmi Weekly, a thriving local newsletter based in Wilmington, North Carolina. With 10,000 subscribers in just over six months, Trenton and his partner Nick Conley are redefining what a local media business can be.
This isn't just a story about newsletters—it's a case study in how hyperlocal content, community building, and strategic optionality can lead to lasting impact and unexpected opportunities. In this article, we dive into the key insights from Trenton's experience and what aspiring newsletter builders can learn.
From Entrepreneur to Local Media Builder
Trenton Hughes didn’t start Wilmi Weekly to chase ad dollars—he started it to build community.
A seasoned entrepreneur with successful exits under his belt, Trenton moved to Wilmington and wanted to lay down roots. The idea was simple: “What if we created a newsletter that actually served the community we live in?” Partnering with newsletter pro Nick Conley, they launched Wilmi Weekly as a fun, event-focused digest that let locals know what was happening around town—from new restaurants to upcoming concerts.
“We thought it’d be fun to fill our own personal need—what’s happening this weekend? What are the new restaurants in town?” Trenton explained.
Trying to make a local newsletter your sole source of income is a recipe for frustration. Trenton is adamant that Wilmi Weekly is more about optionality than short-term ROI. He sees it as a distribution channel that builds trust, audience, and influence—which in turn opens doors.
“You can’t rely on ad revenue alone. The real value is building something that gives you visibility, community, and the chance to pursue other ventures.”
This insight reframes the whole game. Instead of obsessing over CPMs, Trenton is focused on deeper value:
Meeting local investors and business owners
Building a trusted brand that can launch or support other ventures
Creating in-person events and branded merchandise
Exploring future monetization like paid tiers or member perks
Fighting AI Clones with Authenticity
One of the biggest threats? AI-generated copycats. But Trenton isn’t worried.
He’s seen multiple attempts to replicate Wilmi Weekly, including newsletters written by AI and run from entirely different cities. “People can tell it’s not authentic,” he says. “The quality just isn’t there.”
His belief: local newsletters need real humans in the loop, ideally people who actually live in the city. That’s the only way to maintain trust, accuracy, and personality.
“We’re trying to create a brand people are excited about. That’s not something AI can replicate—at least not yet.”
Events Are the Real Engagement Engine
Newsletters are great—but real-world connections matter more.
Trenton and Nick recently hosted their first event: a $20 mixer for young professionals. With 10,000 subscribers to promote it, they quickly sold 20+ tickets and are now exploring more formats—from farmers markets to concerts.
“We’ve seen other events in town pull in hundreds of people. There’s clearly demand.”
Events also have a flywheel effect:
They create new content and photo ops
They deepen reader loyalty
They attract local sponsors and advertisers
And unlike digital ads, they’re much harder for AI clones to replicate.
Ads Are Tough—But Not Impossible
Local ad sales are a grind, especially outbound. Trenton admits they’ve had “lackluster success” with cold outreach and are now leaning hard into brand building and inbound interest.
Their tactics:
Instagram growth and video content
Featuring 30 local businesses in 30 days
Pitching three-month ad packages instead of one-offs
Offering “featured event” slots or perks for paying subscribers
He’s also exploring creative monetization: ticket giveaways, premium tiers, and charging for event submissions. But again, it all starts with building trust and delivering value.
Build for Local—Think Long-Term
What makes a great local newsletter operator? A long-term mindset, local roots, and an entrepreneurial spirit.
Trenton believes the best operators aren’t content creators looking for a quick win—they’re small business owners who understand their city, have skin in the game, and see the newsletter as a strategic asset.
“If you already have existing businesses, even more tremendous. You can push people to those and tailor it toward them.”
Community Is the New Moat
AI might take over the internet—but it can’t take over your local brewery.
Trenton sees a macro trend: people will increasingly seek human connection and local identity in a world overwhelmed by automation and digital noise.
“Most of us crave community. And the more you're building something local, the more opportunities come your way.”
That’s the power of Wilmi Weekly. It’s not just a newsletter—it’s a movement. And it shows what’s possible when you blend entrepreneurship with community and digital media.
Bringing It All Together
Trenton Hughes offers a compelling blueprint for the future of local media. Don’t chase ad revenue. Don’t fear AI. Focus on creating something real, useful, and rooted in your community. From events to optionality to long-term value, the opportunities are massive—but only for those willing to do the work and stay consistent.
How I Can Help You Succeed
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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