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Hi newsletter operators!
Three great podcasts recorded this week! Two are already up, with Justin Gordon and Matt Diehl, which are discussed below. Also recorded a great episode with Frey Chu which should be out this week. He’s a master at directories, so if you’re interested in how to leverage one in your business, it’s a must listen.
Plus, we’ll have another directory based episode sometime in the next two weeks with Tim Stoddart, who truly is an OG directory builder. I’d recommend checking him out right now, because he does a lot of great stuff with his YouTube channel and newsletter, highly recommend them.
I also announced last week that I’m officially launching six more local newsletters with a single partner. Couldn’t be more excited about this. It’s different than what I have been doing with partners, which is launching on with them in the towns they live in. Great model too, but much slower to scale.
This partner is a true sales expert, which gives us such a leg up in the ability to monetize these quickly, then launch more, which is exactly the plan. Keep an eye out for more of what I’m doing there in the future.
Poll
What revenue experiment will you try next?
Justin Gordon - Just Go Grind and The LA Grind
Justin Gordon grew Just Go Grind to 21k founders, then launched The LA Grind, a newsletter that mixes local events with startup news. He shares the 30-hour research routine behind his deep-dives, the LinkedIn + Meta ads that pull less than $1 subs, and the newsletter-podcast-event bundles that convert side projects into real revenue.
Top Three Takeaways
Event-Led Community = Revenue & Optionality
Why events first: In-person connection isn’t automatable. AI only increases demand for real gatherings. Justin hosts hikes, comedy nights, coffee meet-ups, and curated founder dinners.
Membership test: Poll readers on paying $25–$100/mo for 2-4 curated events; use quick Beehive polls to gauge price sensitivity before building.
Segmented invites: Tag VC-backed founders, angels, SMB owners, etc. in Beehive; each segment gets the events—and sponsors—most relevant to them.
Everything here can be switched from the tech/b2b angle towards a regular locals angle. Just have to figure out how you can apply to your niche.
“Founders would rather burn 600 calories on a hike with other founders than network in a bar. Curated experiences make the paywall feel cheap.” — Justin
LinkedIn + Low-Friction Meta Ads Outperform Traditional Local Tactics
Start organic: Justin tapped his USC network and past event RSVPs to land the first 300 subscribers entirely free.
Lean into the right platform: Even with 41k followers on X, LinkedIn drives the bulk of LA-qualified subs because it mirrors his offline network.
Meta ad recipe:
Creative: Simple, AI-assisted image (“LA Startups & VC”) with a one-line value prop.
Targeting: location, 25–55, job titles incl. founder / investor / software.
Result: <$1 per qualified subscriber, then SparkLoop recommends Just Go Grind to recoup CAC.
Key metric: 52 % open rate after two list cleans—quality beats raw volume.
Sell Packages, Not Placements
Multi-touch > one-off: Every deal includes newsletter spots + social posts + podcast interview + co-branded event.
Process:
Build an Airtable CRM of target sponsors.
Warm intro via podcast booking (“Let’s record an episode, then explore a broader collab”).
Price the bundle so one sponsor funds several editions.
Result: Row.com underwrote Justin’s podcast relaunch with a single package covering YouTube, inbox, and a live event—all negotiated before episode #1 dropped.
“If a brand hits founders from three angles, they see real ROI and renew. I stopped pitching single-newsletter slots altogether.”
Action Steps for Local Operators
Plan one unforgettable IRL event next month. Even a free coffee walk creates sponsorable surface area.
Audit your LinkedIn connections. Export local contacts and invite them with a personal note—costs nothing, converts like crazy.
Bundle your assets. Newsletter + Instagram Reel + podcast cameo + ticketed meetup = a price anchor 3-4× higher than an email ad alone.
Consistent effort compounds. Start small, iterate weekly, and your local newsletter becomes the connective tissue your community—and sponsors—can’t live without.
Follow Justin here:
Matt Diehl - Eating Baltimore
Matt Deal has shipped email at $1-billion-a-year Agora, run marketing for a wine club, and launched Eating Baltimore, a food-forward local newsletter that just crossed 5,000 subscribers in three months. In our chat he breaks down the Facebook-ad experiments, the AI-built restaurant directory that powers organic traffic, and why building in public unlocks unexpected partnerships.
Top Three Takeaways
Facebook Ads: Gift-Card Giveaway
“Win a $50 gift card” hook; CAC began at $0.50 then crept toward $1.
Pivot: Studied other local ad libraries (Fort Myers Brief, Naples Brief), dropped the giveaway, and swapped to straightforward “What to do in Baltimore this weekend” creative.
Result: Settled back under $0.50 per subscriber and built a 4 K-follower FB page as social proof.
“Nobody’s asked about the gift card since I killed it—the content itself is the draw.” — Matt
I’m still a big believer in giveaways being a huge opportunity for us, but may not work well as an ad.
An AI-Generated Restaurant Directory Drives SEO & Backlinks
Built in Replit for $6: Prompted the agent with a screenshot of a directory he liked; used Outscraper to import ~2,000 restaurant listings from Google Maps.
Rapid SEO wins: Domain Authority jumped from 2 ➜ 7; SEMrush shows 160+ monthly organic visits after 60 days.
Backlink flywheel: Bulk-emailed restaurants with a “Top Restaurant” badge; those who add the badge link back to Eating Baltimore.
Monetization roadmap: “Editor’s Pick” slots and claimed listings will become paid add-ons to newsletter sponsorships.
Love this! Exactly the kind of thing we talk about in Frey’s upcoming episode.
Build in Public & Scale Systematically
Weekly Twitter metrics thread: Subs, CTR, ad tweaks, even “0 sponsors this week”—transparency attracts peers and prospects.
Spin-off success: Cloned the Baltimore playbook for a 50 K-population suburb—already 1.6 K subs and inbound sponsor interest with zero outbound.
Engagement edge: Small-town Facebook groups deliver 1-2 K Reel views vs. 200 in big-city groups—locals rally around truly local content.
“I’ve got a 9-month-old and a day job; showing the wins and the misses keeps me accountable—and opens doors.”
Building in public is such a good idea, especially in this space. Highly recommend it!
Action Steps for Local Operators
Audit your ad hook. If a giveaway is inflating CAC, test a plain-vanilla value prop for a week.
Spin up a Replit directory. A $10 Outscraper pull + AI front-end = organic funnel + future revenue line.
Tweet your numbers Friday afternoon. Transparency attracts collaborators, early sponsors, and—crucially—keeps you shipping.
Build the list, share the journey, and let local momentum compound.
Follow Matt here:
How AI might change the email inbox
Quick ideas from Matt McGarry about how Gmail then others will change the inbox. Key takeaway is that you need your subscribers to truly be excited to open your email so that it doesn’t get hidden from them. Read it here.
Set up your Apple Business Connect to get logo in inbox
I’m going to work on this soon. Makes tons of sense to do this so your logo is in their inbox, and you’re seen as more legit by readers and Apple. Read more here
Admittedly not sure how to apply this to the local space yet, but I feel like there’s something here for us. I hope some of you try this in some capacity and let me know the results. Read more here
How I Can Help You Succeed
Looking for more from me? Here are the ways I can help:
🎙️ The Podcast - Deep-dive conversations with successful newsletter operators sharing their playbooks and lessons learned | Link
📧 This 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
🦄 Sign Up For Beehiiv - Use my link, because you’re a thoughtful person who wants to help others succeed. And it’ll save you 20%, so just be selfish and do it | Link
Discover all these resources and more at localnewsletterinsider.com
That’s all I got for this issue. If there’s anything you want me to cover or talk about for the next edition, reply to this and let me know!
And reply and let me know if you want to be a guest on the show. Just tell me what you’re up to, and assuming you’re a good fit, I’ll have you on (if you’re reading this, you’re most likely a good fit).
How'd I do?
Thanks for reading Local Newsletter Insider! Please reply and let me know what you think, or anything you think I could do better. Love to get some actionable feedback.
