Automating Outreach vs. Personal Follow-up

This episode digs into how Jimmy Farrell grew CHS Happenings—a Charleston, SC local newsletter—from 0 to 10,000+ subscribers with a deliberate, community-first approach. We cover why he chose a personality-led brand, how he thinks about weekly cadence, and why Instagram—not LinkedIn—is his main growth channel for local audiences. We also talk through the real tradeoffs of pausing paid growth to focus on monetization.

Jimmy breaks down his progression from residential real estate content to a full newsletter, what he learned from Meta ads (and why costs/targeting matter), and how consistent “scoop” reporting (like pegging the location of Charleston’s second Trader Joe’s) builds trust. He shares how he’s now producing short local business interviews, using ManyChat for IG DMs, and summarizing paywalled articles to restore click-through behavior.

Key takeaways: lead with a real human, publish reliably (weekly can be enough), push discovery on Instagram, and build a focused prospect list of high-lifetime-value categories (banks, dentists, med spas, premium real estate). Automate first-touches, then go 1:1 once people engage. Use sponsorship revenue to fund sustainable paid growth rather than chasing vanity list numbers.

Guest contact information: 

Instagram: @chs.happenings; 

LinkedIn: Jimmy Farrell (DMs open). 

Newsletter: CHS Happenings (Charleston, SC).

#Charleston

#CHSHappenings

#LocalNewsletter

#NewsletterGrowth

#NewsletterMonetization

#InstagramMarketing

#MetaAds

#LocalBusiness

#CommunityNews

#RealEstateMarketing