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

Brian Skinner joins TJ Larkin to break down the growth strategy behind Marin Buzz, his successful local newsletter. The two discuss how local content can open doors in business, community involvement, and influence, even without a clear long-term plan. Brian credits a single podcast for sparking his idea, and within weeks he launched a brand that's now a growing asset in his local ecosystem.

They explore how Brian structured his early content around weekend events and slowly added segments like "Pet of the Week," “Marin History,” and “Zillow of the Week.” The discussion reveals how Brian focused on sustainability and community engagement over perfection and how this strategy paid off with inbound advertisers and high open rates.

For those interested in local media, Brian offers actionable advice on using Instagram as both a growth and sales channel. He shares his outreach method using Instagram DMs and AI-assisted tools to identify and contact potential advertisers. His products, YapOver and TwistAI, are designed to reduce friction in content creation and monetization.

Check out Brian’s work:

Newsletter: https://www.marinbuzz.com/

Instagram Tool: https://www.yapover.com/

AI Tools & Services: https://www.twistai.com/

#LocalNewsletter

#CommunityMedia

#EmailMarketing

#SmallBusinessTips

#ContentStrategy

#InstagramGrowth

#AIForCreators

#DigitalMonetization

#StartupStories

#LocalMarketing

Jas from Winnipeg Digest returns to talk growth, revenue, and diversification. In just three months, he's scaled up recurring events, coffee parties, and brought in steady advertising revenue—without burning out. He shares tactical insights into acquiring subscribers at under $1 through Facebook ads and optimizing creatives to keep costs low.

Jas also previews his next business move: launching a Christmas lights installation company, built off the trust and reach of his audience. He explains how audience alignment and a seasonal services model open up new monetization paths without needing more advertisers.

You’ll hear tips on maintaining creative freshness in paid ads, handling advertiser churn, and why content quality and trust remain the core of everything Jas builds.

Contact Info:

Jas – Winnipeg Digest

Instagram: @winnipegdigest

Email: [email protected]

#LocalNewsletters

#NewsletterGrowth

#WinnipegDigest

#CommunityEvents

#EmailMarketing

#FacebookAdsTips

#MonetizationStrategy

#CoffeeParties

#SmallBusinessMarketing

#CreativeTesting

Want to grow a local newsletter without waiting months to recoup ad spend? Louis Nicholls, co-founder of SparkLoop, breaks down “zero-day payback” tactics—mixing paid recommendations, trip-wire offers, and high-value local lead-gen deals—to help operators turn every 50-cent subscriber into immediate profit.

Louis shares real-world tests (including his own) that combine three monetization layers on the thank-you page and in the first 24 hours, plus tips for negotiating $10-$100 per lead with home-service pros, gyms, and even med-spas. He also explains why sending two welcome emails the first day actually boosts engagement and weeds out the wrong readers. 

Key takeaways: focus on arbitrage cheap Facebook leads, create irresistible “free money” offers, and don’t fear higher send frequency.

Connect with Louis: growmynewsletter.com (newsletter, YouTube & resources) • Twitter/X @louisnicholls • Explore SparkLoop at sparkloop.app

#Newsletters #EmailMarketing #LocalMedia #SparkLoop #LeadGeneration #Monetization #LouisNicholls #MediaBusiness #SubscriberGrowth #DigitalPublishing

In this episode, TJ Larkin sits down with Jacob Espinoza from What’s Happening Salem to unpack how Jacob built a thriving local media presence using Instagram, newsletters, and a podcast. Jacob breaks down his process of launching a local brand from scratch just over a year ago and how he's since scaled to 35k+ Instagram followers and 10k newsletter subscribers.

Jacob shares specific tactics that helped him succeed—such as green screen announcements, short-form video strategies, and hyperlocal memes—and emphasizes the importance of blending education with entertainment. He also explains how he differentiates Instagram content from newsletters to reach distinct audiences, and why a visible social presence gives you instant credibility with advertisers.

The conversation moves into monetization and Jacob’s innovative approach to ads, like showcasing businesses through engaging content rather than traditional promos. He also details how he hosts local events and highlights the power of face-to-face branding. Whether you're looking to grow a local audience or monetize effectively, Jacob delivers clear, replicable tactics.

📍Learn more about Jacob at https://jacobespinoza.com/

📱Twitter: https://twitter.com/MrJacobSB

#LocalMedia

#InstagramMarketing

#NewsletterGrowth

#ContentCreatorTips

#ShortFormVideo

#CommunityNews

#SmallBusinessMarketing

#LocalInfluencer

#SocialMediaStrategy

#JacobEspinoza

What’s the real opportunity behind building online directories? In this insightful interview, Frey Chu outlines how he built multiple passive income streams from niche directories using SEO and strategic content design. TJ and Frey also unpack how these learnings can be applied to local media—especially newsletters.

Frey explains how local directory builders can shortcut growth by scraping data, optimizing for Google, and testing monetization strategies like sponsored listings, lead generation, and ad bundling. He also shares how directories become even more powerful when paired with newsletters or social audiences, as a way to open conversations with advertisers and deliver proven ROI.

This episode is packed with practical insights for anyone interested in local business, media, SEO, or building “boring but beautiful” internet assets that compound over time.

📍 Connect with Frey Chu:

• Website: Ship Your Directory
  

• YouTube: Frey Chu
  

• X (Twitter): @freychu

#OnlineDirectories

#LocalMedia

#SEO

#LeadGeneration

#PassiveIncome

#DigitalMarketing

#NewsletterBusiness

#FreyChu

#DirectoryBusiness

#ShipYourDirectory

Geoff Matthews of North Shore Now joins TJ Larkin to unpack the real story behind launching a successful newsletter in a small geographic niche. Geoff candidly shares the challenges of selling local ads, testing paid subscriber models, and staying motivated despite uncertain ROI. With refreshing honesty, he outlines what worked, what flopped, and why feedback from his community keeps him going.

From curating events across 100+ websites to running giveaways and launching merchandise, Geoff’s grassroots approach to content and engagement offers tons of lessons for creators in any market. He also breaks down his ad strategy evolution, from failed cold emails to drastically improving performance with expert help.

Whether you're building your first audience or thinking about monetizing a niche project, this conversation is loaded with valuable insight. Want to connect with Geoff? Head to https://snowballclub.com/ to learn more about his private founder community.

#NewsletterBusiness

#LocalMarketing

#EmailMarketingTips

#ContentStrategy

#DigitalEntrepreneur

#NorthShoreNow

#CommunityBuilding

#MetaAds

#MonetizingContent

#VancouverBusiness