What happens when local journalism disappears? For Kyle Scott, a former sports media founder turned newsletter operator, the answer wasn’t just a void — it was an opportunity. In this compelling conversation with TJ Larkin, Kyle breaks down how he built Walking the Boards, a wildly successful newsletter serving Ocean City, New Jersey, and how that evolved into something much bigger. From grassroots growth to major business strategy, this is a masterclass in how to build, scale, and monetize local media in 2025.
Whether you're a small business owner, aspiring publisher, or just newsletter-curious, you'll walk away with actionable insights on how to grow your audience, generate revenue, and avoid common traps.
From Local Blog to Regional Powerhouse
Kyle Scott’s journey from sports blogger to newsletter mogul proves that niche, local content can scale — with the right strategy.
With over 15 years in local media, Kyle made his mark by founding Crossing Broad, a leading independent sports site in Philadelphia. After selling the business in 2020 (partly thanks to the online gambling boom), he pivoted to newsletters. Why? Simple: control.
“One algorithm change from Google or Facebook and your business is toast,” Kyle explained.
Kyle began experimenting with newsletter tools like Beehiv, likening it to Shopify for audience builders. His big bet: a hyperlocal newsletter for Ocean City, NJ — population 12,000 — that swells to over 100,000 in summer.
Launching Walking the Boards
Ocean City was ripe for disruption: huge seasonal traffic, zero real local coverage, and a passionate community.
Kyle saw the gap — no full-time media presence in one of the most affluent and popular shore towns in the Northeast. Armed with Beehiv and a Facebook Ads strategy, he began building Walking the Boards.
“We hit thousands of subscribers in months. People stopped me on the street — they recognized me from my Beehiv profile picture.”
Within two years, the newsletter had over 17,000 subscribers and 50%+ open rates. The model was clear: leverage Facebook for fast growth, double down when engagement proves it’s working.
The Fork in the Road: Monetization Models
Once your list grows, the question becomes: solo operator or media company? Kyle chose both.
Initially, Kyle faced the same challenge as many local publishers — ad sales were limited to small budgets from mom-and-pop shops. Instead of grinding out $500 deals, he merged with a regional media company, bringing Walking the Boards into a larger network of newsletters and websites across South Jersey and Philly.
“Now we can sell to hospitals and casinos — advertisers with five- and six-figure budgets.”
It’s a path more creators are taking: bundling local audiences to attract regional ad dollars. For Kyle, it’s meant board seats, not bartending nights.
Why Local Business Owners Should Lead the Charge
Kyle believes the most underrated players in the local media boom are small business owners themselves.
These entrepreneurs already have revenue, local knowledge, and a stake in the community. Adding a newsletter isn’t about new income — it’s about growing their core business.
“Trust is 90% of the game,” Kyle said. “If you’re emailing people weekly, they’ll think of you first when they need a mortgage broker, florist, or lawyer.”
The secret? Provide real value. Kyle warns against overly promotional content. Instead, treat it like true media — then soft-sell your services in the margins.
Include your business in a “sponsored by” footer
Offer value-first stories and insights
Use your newsletter to build partnerships and referrals
Scaling Through Influence and Leverage
With a large enough audience, influence follows — and so does access.
Kyle’s survey data turned into political clout. He found himself in meetings with Ocean City’s mayor and city council, just a year after launching the newsletter. Politicians recognized his list was reaching more voters than traditional campaigns.
“I had 2,000 readers in a voting ward that only had 800 voters. The mayor took notice.”
This level of influence can translate into business leverage, partnerships, and — for the bold — political power.
The B2B Pivot: Buying Sandlot
After mastering local newsletters, Kyle aimed higher — and more niche.
His latest venture, Buying Sandlot, targets the business side of youth sports, a $50–70 billion market. It’s a classic B2B play: underserved niche, high-value readers, and scalable monetization.
Surprisingly, he’s growing it the same way: Facebook ads.
“We’re getting B2B subscribers for under $2 each. The algorithm knows who to find.”
The playbook mirrors Walking the Boards, but with B2B monetization upside: premium subs, conferences, and brand sponsorships. Kyle’s already seeing traction with high-level advertisers and industry operators from day one.
Bringing It All Together
Kyle’s story showcases the power — and flexibility — of newsletter media today. Whether you’re serving a small beach town or a national B2B niche, the same principles apply: own your audience, create value-first content, and build smart monetization around trust and scale.
The opportunity for entrepreneurs — especially local business owners — has never been greater. But you have to pick your path: hobbyist, solo operator, or scale builder. As Kyle put it, “You can’t half-ass it in one town and expect big returns.”
Pick your lane. Deliver real value. And own the channel — before someone else does.
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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