Justin Gordon returns to share the LA Grind playbook: a local newsletter for founders, operators, and investors in Los Angeles that blends curated events, deal flow, jobs, and “living in LA” picks. In just four months, he’s crossed ~5,200 subscribers (as of Sept 25) and turned the list into a thriving in-person community.

We dig into the growth stack (Meta ads + LinkedIn + event flywheels + Luma), why paying $1–$1.50 per subscriber can still be a steal, and how welcome surveys/polls power better sponsors and programming. Justin also shares his low-lift event philosophy—hikes, mixers, breakfasts, coffee meetups, even poker—that keeps logistics simple while relationships compound.

You’ll hear concrete monetization tactics: recurring $29/month memberships with 2+ curated events, ticketed mixers with sponsors, and how he uses survey data to line up bigger vertical partners (like real estate) and explore recruiting/job board revenue. We also cover expansion thinking (SF/NY), intimate retreats vs. larger summits, and how to decide what to launch next.

Guest contacts: 

Justin Gordon

Website: thelagrind.com

#LAStartups

#LAtech

#LocalNewsletter

#NewsletterGrowth

#CommunityBuilding

#EventMarketing

#CreatorEconomy

#StartupEvents

#MembershipModel

#JustinGordon

Ashlyn of Cypress Digest breaks down how she grew a Houston-area local newsletter to ~3,300 subscribers with a ~53.6% open rate and ~11% CTR, then flipped the switch on revenue. The headline tactic: a simple Facebook Lead Ad campaign that brought in ~75 advertiser leads for about $60—sub-$1 per lead—by pitching “partnerships” to local businesses instead of generic ads. She compares this inbound flow to slower, time-intensive methods like cold email, scraping, and chasing gatekeepers.

She also explains using Apollo as an affordable CRM/data source to bypass catch-all inboxes, how she warms prospects (DM → email open → call), and where cold calling fits for higher-LTV categories. Beyond ads, Ashlyn shares a scalable directory play built on a V0 (vZero) subdomain, plus how “Local Falcon” informs which businesses to list and later upsell. We also dig into competing with big-box local media and why speed, focus, and pricing help a solo publisher win.

Takeaways include: test fast and kill what doesn’t work; pitch outcomes, not placements; use demographics and creative samples to close; create low-ticket on-ramps (directory listings) for small operators; and blend front-end ads with back-end local SEO services for durable value. If you’re building a local media business, this is a concrete blueprint.

Guest Contacts:

Ashlyn Brooks

Cypress DigestWebsite: cypressdigest.com

Directory: directory.cypressdigest.com

Email: [email protected]

#LocalNewsletter #LeadGen #FacebookAds #LocalSEO #Beehiiv #SmallBusinessMarketing #DirectoryListings #ColdEmail #ApolloIO #CommunityMedia

This episode dives into how a local newsletter can punch above its weight by pairing digital reach with in-person events. John Apolinar of Scottsdale Scoop shares the playbook behind his first paid happy hour—securing a sponsor, choosing a venue (the W in Old Town), and using raffle incentives to boost registrations. We dig into why IRL touchpoints build trust and open doors for bigger partnerships down the line.

John breaks down his early results (37+ paid signups, ~$500 in tickets), the sponsor economics (venue and first drink covered), and seed-stage interest from brands—including Rivian—eager to host future gatherings. We also cover content that pops on Instagram (short green-screen updates, new openings/closures, and carousels), plus how a student intern from Handshake can produce dependable carousel posts each week.

You’ll hear a candid look at monetization: using SmartLead for cold outreach (with burner domains/inboxes), why high-ticket local categories convert better, packaging two newsletter ads with an event, and the next frontier—turning the welcome flow into consistent CPL revenue so paid acquisition can scale. Key takeaways: keep the first event simple, sell packages not one-offs, track what performs on IG, and experiment with segmented onboarding offers.

Get in touch with John Apolinar

🐦 Twitter / X: it’s “John Apolinar” (DMs open)

Get started with Smartlead: https://www.smartlead.ai/?via=92189

#LocalNewsletters #Scottsdale #EventMarketing #CommunityBuilding #NewsletterGrowth #Sponsorships #InstagramMarketing #ColdEmail #LocalMedia #Beehiiv

In this episode, TJ digs in with creator and local media operator Jacob Espinoza on what really works for a city-focused podcast and Instagram presence. They cover why local podcasts are hard to grow, the outsized networking value of interviews, and how to keep production simple enough to sustain week after week. You’ll hear how Jacob repurposes interviews across newsletters and short-form video to multiply reach.

Jacob breaks down his toolkit (Riverside, repurposing flows, and Beehiv-style newsletter ops), his “green screen” explainer format for rapid local updates, and the difference between teaser-style clips and value-first reels that spark comments. They also discuss timing newsletters (evening sends), testing subject lines with AI, and packaging multi-platform inventory sponsors actually want.

You’ll learn how to price and pace sponsored reels, balance ads with organic value, and use social proof from Instagram to close deals—even if your podcast listens are modest. Jacob shares practical tactics for finding early guests, posting imperfect clips to learn faster, and making “make-goods” when a sponsored post underperforms.

Get in touch with Jacob Espinoza

📸 Instagram: What’s Happening Salem

🎥 TikTok: What’s Happening Salem

🐦 Twitter/X: @MrJacobSB

📸 Instagram (personal): @MrJacobSB

#LocalMedia #Podcasting #InstagramReels #ShortFormVideo #GreenScreen #NewsletterMarketing #Sponsorships #ContentStrategy #RiversideFM #Beehiiv

This episode dives into how local newsrooms can turn written stories into habit-forming podcasts. Paul Gewuerz of LocalPod explains his “news blast” format—8–12 minute shows that package top stories, quick ad breaks, and local happenings—plus how AI text-to-speech streamlines production without sacrificing editorial quality.

We also unpack why newsletters and podcasts overlap so strongly and why upgrading away from clunky PDF “e-papers” is table stakes in 2025.Paul details a surprisingly effective growth channel: geo-targeted audio ads. Using platforms like AudioGo, publishers can place 30-second promos inside podcasts and music apps in specific ZIP codes—reaching people who are already audio-first.

We discuss where legacy outlets are adapting well, where they’re still stuck, and how digital-first independents (including LION Publishers members) are carving out sustainable businesses.

Key takeaways: start with a short, consistent show; repurpose your best stories; promote through your newsletter; test geo-targeted audio ads; sell creative placements that drive foot traffic; and remember that local trust becomes more valuable as AI floods the broader web.

We also touch on franchise and network models (e.g., TapInto) and creative cross-subsidiaries that can fund journalism in smaller markets.

Get in touch with Paul Gewuerz

🌐 Website — localpod.co

📧 Email — [email protected]

🎙️ Podcast — Small Press Big Ideas

📰 Newsletter — Local News Industry Pulse (on Beehiiv)

💼 LinkedIn — Paul Gewuerz

#LocalMedia #Podcasting #AIinMedia #TextToSpeech #Newsletters #AudioAds #GeoTargeting #MediaMonetization #LocalNews #SmallPressBigIdeas

Agency operator Nathan May joins to unpack what actually scales newsletters in 2025: disciplined paid acquisition on Meta, creative that calls out real problems, and a monetization ladder that doesn’t stop at ad slots. We contrast broad B2C with small-but-mighty B2B niches—and show why “local + [professional audience]” can 10x sponsor value.

We get tactical: swipeable internal workflows for AI-assisted curation, using post-signup forms to optimize for the right readers, and specific ad concepts sourced from Reddit (e.g., solving loneliness with events content). We also break down selling in the early days—DMs to high-LTV categories, showing up in person, and smart bundles across newsletter, site, and reels.

Key takeaways: execution beats incumbents, qualify your funnel, build offer packages not one-offs, and add local video to protect against “AI slop.” Plus, why big platforms may automate more of targeting/creative—but strategy and signals still win.

Guest Contact Information: Nathan May

Agency: The Feed Media

Newsletter: Newsletter Growth Memo

Podcast: Personal IPO with Beehive

#LocalNewsletters

#NewsletterGrowth

#MediaMullet

#LocalMedia

#MetaAds

#Beehive

#B2BMarketing

#AIforWriters

#CreatorEconomy

#AdSales

In this conversation, entrepreneur and creator Tim Stoddart explains why authenticity and consistency outperform overproduction—and how those same principles power high-margin local service businesses. We dig into his journey from documenting sobriety to building media assets, agencies, and newsletters, and why local SEO remains a durable path for independents.

Tim shares a clear model: start with a simple, repeatable service (local SEO), add media to build authority, and layer in directories for compounding leverage. We break down “winner-take-most” local packs, realistic pricing, and why delayed gratification is the core SEO skill. He also tackles packaging: how to combine newsletter ads, listings, podcast features, and basic SEO into offers that businesses actually buy.

You’ll learn how to pick higher-ticket local niches, sell without undercutting yourself, and structure processes that ship every week. We also zoom out on AI’s impact: why local intent is a protective moat and why community, offline touchpoints, and real-world presence are only getting more valuable.

Get in touch with Tim:

Website & personal newsletter — TimStodz.com

YouTube — Tim Stoddz

wordofmouthconversations.com

Copyblogger — Copyblogger.com

Social:

Twitter / X — @TimStodz

LinkedIn — Tim Stoddart

Instagram — @TimStodz

TikTok — @TimStodz

#LocalSEO #Directories #NewsletterGrowth #CreatorEconomy #SmallBusinessMarketing #PersonalBranding #ContentStrategy #AgencyLife #Hyperlocal #Entrepreneurship

In this episode, TJ sits down again with Jas from Winnipeg Digest to talk about the latest experiments and strategies in local newsletter publishing. They discuss the upcoming Business of Local conference in Salt Lake City, the pros and cons of cash giveaways, and the importance of building trust with your audience instead of chasing vanity metrics.

Jas shares updates on his community-building efforts, from coffee parties to launching Digest Lights, a holiday lights installation business born out of his newsletter audience. He explains how a giveaway generated hundreds of qualified leads, his sales process for closing $2,500+ projects, and why retention in seasonal services is so valuable.

The conversation also dives into social media strategy, comparing reels and carousels, outbound ad sales systems, and welcome email sequences that actually drive engagement. Whether you’re running a newsletter or exploring new business ideas, this episode is packed with practical lessons from the trenches.

Connect with Jas on Twitter: https://twitter.com/jas

#LocalNewsletters

 #NewsletterGrowth

 #CommunityBuilding

 #WinnipegDigest

 #DigitalMedia

 #SmallBusinessGrowth

 #EmailMarketing

 #LocalMedia

 #Entrepreneurship

 #ContentStrategy

Baltimore creator Matt Diehl explains how a spontaneous “cash-drop” video, just $80 taped to a harbor post, skyrocketed to 1.5 million views across Facebook, TikTok and Instagram. The 10-second clip added 10 K followers and 500 new email subscribers to his Eating Baltimore newsletter.

He breaks down the tactics that made it pop: filming with zero polish, posting natively on each platform, and even embracing critics who wondered how you peel bills off duct tape. Matt also shares the numbers behind platform performance (Facebook shocked everyone), and why contrarian “mistakes” can actually juice engagement.

Key takeaways: keep production frictionless, post natively, and drop a templated subscribe link early. Leverage comments, positive and negative, to feed the algorithm. Then convert the buzz by funneling viewers into newsletters and sponsorship deals.

Connect with Matt Diehl:

• Facebook: Eating Baltimore

• Instagram: @eating.baltimore

• TikTok: @eatingbaltimore

#CashDrop

#LocalNewsletter

#BaltimoreEats

#SocialMediaMarketing

#EmailGrowth

#RestaurantMarketing

#GiveawayStrategy

#ContentMonetization

#SmallBusinessTips

#MattDiehl

I’m going solo in this episode to share eight key strategies and lessons I’ve picked up over the past month. I walk through a high-performing apartment locator ad campaign, what I’ve learned from cold DMs on Instagram, and why I believe custom home builders are perfect targets for newsletter advertisers. I even show how I used ChatGPT to craft outreach messages that are already turning into real deals.

I also dive into email engagement tactics—like why simply asking subscribers to reply “Yes” can dramatically boost response rates—and how I’m using tools like SparkLoop to help monetize at scale. I break down performance across several city-based newsletters and why I’m now seeing that slower growth often leads to better open rates and higher list quality.

In the final segment, I share an idea I’m really excited about: turning newsletters into multi-channel local media brands using small, ad-heavy print magazines. I’m rethinking the economics of print and exploring how even lightweight physical media can strengthen brand visibility and bring in real revenue.

Want to get in touch?

Email: [email protected]

Website: https://localnewsletterinsider.com

Twitter: https://twitter.com/tjlarkin

#LocalNewsletters

#EmailMarketing

#NewsletterGrowth

#DigitalAdvertising

#InstagramOutreach

#MediaMonetization

#NewsletterTips

#SparkLoop

#PrintMarketing

#NewsletterStrategy