Justin Gordon quit his job at a venture firm to start a newsletter. Nine months later, he crossed $100K in revenue.

In this episode, Justin breaks down exactly how he built the LA Grind and SF Grind into real businesses. Not just newsletters. Businesses with events, sponsorships, and a paid membership that grows every single month.

We get into the specifics: how he closes $5K event sponsors like JustWorks and Citizens Private Bank, how he hosted a 250-person event with a 280-person waitlist, and the exact funnel that turns free newsletter subscribers into paying members at $59/month.

Justin also talks about selling his previous newsletter (Just Go Grind) through Acquire.com and why he went all-in on local over national.

If you're building a newsletter, running events, or trying to figure out how to actually make money in local media, this one is packed.

What we cover:

Crossing $100K revenue in 9 months with the LA Grind

Launching a second newsletter (SF Grind) and hitting 2,000 subscribers fast

How to get enterprise sponsors for local events

Building a paid membership alongside a free newsletter

Selling a newsletter and why focus matters

The content expansion plan: deal flow, founder profiles, and startup news

Why local beats national for newsletter monetization

Connect with Justin:

The LA Grind: https://thelagrind.com/

The SF Grind: https://thesfgrind.com/

Build your own local media business:

https://localmediahq.com/  

https://lightbreak.ai/

Subscribe to the Weekly Newsletter:

https://www.localmediahq.com/subscribe 

Join the Community (Discord):

Connect with TJ, share ideas, ask questions, and be part of a growing creator & media community

👉 Join here: https://discord.localmediahq.com/

Follow My Journey

Twitter/X: https://x.com/TJLarkin23 

Instagram: https://www.instagram.com/tj.larkin 

LinkedIn: https://www.linkedin.com/in/tjlarkin1 

Website: https://tjlarkin.com/ 

Work With Me

For brand partnerships, sponsorships, and business inquiries:

[email protected]  

#LocalNewsletter #NewsletterBusiness #StartupCommunity #EventSponsorship #NewsletterMonetization #CommunityBuilding #LocalMedia #FounderEvents #NewsletterGrowth #PaidMembership

Michelle Rueda shares how she grew What's Weird ATX to nearly 5,000 subscribers without spending a single dollar on advertising. As an engineer with over 16 years of experience, she built Social Radar, an iOS app that notifies her whenever someone on Reddit asks questions relevant to her Austin events newsletter. Instead of spending hours searching Reddit manually, the tool alerts her to opportunities where she can authentically engage and provide value. Her approach has generated as much as 1,000 subscribers from a single comment.

The key to Michelle's success is maintaining authentic, human responses rather than using AI-generated content. She emphasizes the importance of genuinely answering specific questions and building trust through real engagement. By focusing on providing value first and mentioning her newsletter naturally when relevant, she's built strong brand recognition in the Austin community. Michelle also discusses the importance of building Reddit karma before actively promoting, ensuring your account has credibility within the community before engaging in promotional activities.

In this conversation, Michelle and TJ explore the future of local newsletters, the role of AI-assisted creator brands, and how maintaining human authenticity while leveraging technology creates sustainable growth. Michelle is currently working on expanding Social Radar into a managed service and developing an events tool for major metro areas, helping other newsletter operators grow their audiences organically.

Michelle Rueda runs What's Weird ATX newsletter at whatsgoodatx.beehiiv.com. Learn more about Social Radar at trysocialradar.com. If you're interested in the events tool for major metro areas, reach out through the Social Radar website.

Subscribe to the Weekly Newsletter:

https://www.localmediahq.com/subscribe 

Join the Community (Discord):

Connect with TJ, share ideas, ask questions, and be part of a growing creator & media community

👉 Join here: https://discord.localmediahq.com/

Follow My Journey

Twitter/X: https://x.com/TJLarkin23 

Instagram: https://www.instagram.com/tj.larkin 

LinkedIn: https://www.linkedin.com/in/tjlarkin1 

Website: https://tjlarkin.com/ 

Work With Me

For brand partnerships, sponsorships, and business inquiries:

[email protected]  

#NewsletterGrowth #RedditMarketing #LocalNewsletter #OrganicGrowth #ContentMarketing #CommunityBuilding #AustinTech #NewsletterStrategy #SocialRadar #MediaBusiness

Tad Moore runs NWA Daily, a 41,500-subscriber local newsletter in Northwest Arkansas with a 54% open rate and 7% click-through. What started as a content writing gig in 2020 evolved into Director of Operations and eventually Strategic Advisor as they expanded beyond the newsletter into real estate and consulting. Most growth came organically through social media, collaborations, and giveaways rather than Meta ads. They're part of Around Town Media, operating newsletters across multiple cities including Kansas City.

The conversation reveals their creative referral strategy: donating $1 to local nonprofits for every referred subscriber instead of traditional discounts. Tad explains how they maintain healthy relationships with "competing" newsletters in the same region, sharing ideas freely because local focus eliminates real competition. They've since launched Skipstone, a real estate brokerage, and Skipstone Group, which helps others start local newsletters. The episode dives into the challenges of building custom newsletter platforms versus using established providers, with honest takes on AI tools and email deliverability.

Check out NWA Daily at nwadaily.com, Skipstone Group at skipstonegroup.com, or connect with Tad Moore on LinkedIn.

Subscribe to the Weekly Newsletter:

https://www.localmediahq.com/subscribe 

Join the Community (Discord):

Connect with TJ, share ideas, ask questions, and be part of a growing creator & media community

👉 Join here: https://discord.localmediahq.com/

Follow My Journey

Twitter/X: https://x.com/TJLarkin23 

Instagram: https://www.instagram.com/tj.larkin 

LinkedIn: https://www.linkedin.com/in/tjlarkin1 

Website: https://tjlarkin.com/ 

Work With Me

For brand partnerships, sponsorships, and business inquiries:

[email protected]  

#LocalNewsletter #NewsletterBusiness #NWADaily #EmailMarketing #ContentCreation #BeehiveNewsletter #LocalMedia #CommunityJournalism #NewsletterGrowth #AroundTownMedia

Book a demo at lightbreak.ai to see our newsletter software in action!

Shane Brady joins TJ Larkin to discuss the current state of local newsletters and media businesses. Shane operates multiple newsletters with approximately 32,000 total subscribers, with his largest newsletter reaching 12,000 subscribers. They cover the surprising interest from legacy media companies looking to acquire newsletter businesses, including Shane's recent conversations with an established local media company exploring potential acquisition.

The discussion reveals how traditional publishers are becoming aware of the creator-led newsletter movement and the strategies being used to grow subscriber bases through Meta advertising.

The conversation dives into practical growth strategies, including Meta ad acquisition costs, three-times-weekly publishing schedules, and monetization through local business advertising. Shane and TJ discuss why legacy media companies have mastered monetization but struggle with modern growth tactics, while independent newsletter operators have figured out subscriber acquisition but often face monetization challenges. They explore the hesitation legacy media has toward using Meta ads, both because they view Meta as a competitor for local advertising dollars and due to philosophical resistance to paying for audience growth.

Key insights include the importance of time management for newsletter operators, focusing on efficiency over perfection, and understanding your core business goals, whether that's direct revenue, building a personal brand for political aspirations, or leveraging newsletter expertise to launch a digital marketing agency. Shane and TJ also introduce their new partnership on lightbreak, newsletter software designed for local publishers, and announce their upcoming podcast "Media Creates Leverage" focused on how media brands create business opportunities beyond advertising.

Shane Brady Contact: Lightbreak.ai for newsletter software demos and partnerships. Follow Shane's work with local newsletters and connect regarding Media Creates Leverage podcast through TJ Larkin's channels.

Subscribe to the Weekly Newsletter:

https://www.localmediahq.com/subscribe 

Join the Community (Discord):

Connect with TJ, share ideas, ask questions, and be part of a growing creator & media community

👉 Join here: https://discord.localmediahq.com/

Follow My Journey

Twitter/X: https://x.com/TJLarkin23 

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LinkedIn: https://www.linkedin.com/in/tjlarkin1 

Website: https://tjlarkin.com/ 

Work With Me

For brand partnerships, sponsorships, and business inquiries:

[email protected]  

#LocalNewsletters #NewsletterBusiness #MetaAds #LocalMedia #NewsletterMonetization #CreatorEconomy #MediaBusiness #DigitalPublishing #NewsletterGrowth #EntrepreneurPodcast

Keith Pepper, owner of Rough Draft Atlanta, shares how he acquired a legacy print media company during the height of the pandemic and transformed it into a profitable, digital-first local media brand. The conversation explores the realities of owning and operating a modern community news business.

Keith explains why print still represents more than 70 percent of Rough Draft’s revenue, how saturation mail distribution changes advertiser value, and why weekly and monthly print products can still thrive. He also breaks down the role newsletters play as the “new morning paper” for local audiences.

The episode dives into ad sales strategy, sponsored content, newsletter monetization, and why focusing on high-value advertisers is critical. Keith also discusses scaling cautiously, acquiring complementary publications, and building sustainable local journalism without venture capital pressure.

Guest contact information:

Website: https://roughdraft.news/

LinkedIn: Keith Pepper

Subscribe to the Weekly Newsletter:

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Join the Community (Discord):

Connect with TJ, share ideas, ask questions, and be part of a growing creator & media community

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Follow My Journey

Twitter/X: https://x.com/TJLarkin23 

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LinkedIn: https://www.linkedin.com/in/tjlarkin1 

Website: https://tjlarkin.com/ 

Work With Me

For brand partnerships, sponsorships, and business inquiries:

[email protected]  

#LocalMedia

#Newsletters

#MediaBusiness

#DigitalPublishing

#PrintMedia

#CommunityNews

#AdSales

#MediaEntrepreneur

#LocalJournalism

#RoughDraftAtlanta

Social media has become the fastest and most effective way to build a local media brand, and Jacob Espinoza is proving it. In this episode, TJ Larkin and Jacob walk through how creators are replacing newspapers and local TV by delivering timely, trusted information directly on Instagram.

Jacob shares lessons from growing What’s Happening Salem to tens of thousands of followers, including the content formats that perform best, how to stay consistent without burning out, and why social proof matters when working with local businesses. They also explore monetization strategies, from sponsored posts to content creation for partners.

The episode wraps with a forward-looking discussion on AI, trust, and why being visibly local is becoming more valuable, not less. If you’re early in local media or considering launching a city-focused brand, this conversation provides a realistic roadmap.

Guest Contact Information:

Jacob Espinoza

Community: The Local Social Club

Website: https://school.com/thelocalsocialclub

Instagram: @whatshappeningsalem

Subscribe to the Weekly Newsletter:

https://www.localmediahq.com/subscribe 

Join the Community (Discord):

Connect with TJ, share ideas, ask questions, and be part of a growing creator & media community

👉 Join here: https://discord.localmediahq.com/

Follow My Journey

Twitter/X: https://x.com/TJLarkin23 

Instagram: https://www.instagram.com/tj.larkin 

LinkedIn: https://www.linkedin.com/in/tjlarkin1 

Website: https://tjlarkin.com/ 

Work With Me

For brand partnerships, sponsorships, and business inquiries:

[email protected]  

#LocalMedia

#SocialMediaStrategy

#LocalNews

#InstagramGrowth

#CommunityBuilding

#ContentCreators

#DigitalMedia

#LocalBusinessMarketing

#CreatorEconomy

#LocalSocialClub

Amy Vartenuk joins the podcast to share how she’s building Clevelandish, a modern local newsletter focused on connection, positivity, and personality. Funded by a local business owner but operated independently, Clevelandish offers a unique hybrid model for local media entrepreneurs.

Amy explains how polling readers, encouraging replies, and leaning into her own perspective helped differentiate Clevelandish from traditional media outlets. She also discusses how being creator-led makes the brand more resilient in an era of AI-generated content.

Listeners will hear real-world insights on paid subscriber growth, advertiser outreach through Instagram DMs, and why not every advertiser is the right fit. Amy emphasizes sustainability, creative freedom, and designing a media business that supports long-term growth rather than burnout.

Guest Info:

Clevelandish Website: https://clevelandish.com

Socials: @clevelandish_oh (Instagram, TikTok, Facebook)

Subscribe to the Weekly Newsletter:

https://www.localmediahq.com/subscribe 

Join the Community (Discord):

Connect with TJ, share ideas, ask questions, and be part of a growing creator & media community

👉 Join here: https://discord.localmediahq.com/

Follow My Journey

Twitter/X: https://x.com/TJLarkin23 

Instagram: https://www.instagram.com/tj.larkin 

LinkedIn: https://www.linkedin.com/in/tjlarkin1 

Website: https://tjlarkin.com/ 

Work With Me

For brand partnerships, sponsorships, and business inquiries:

[email protected]  

#LocalNewsletter

#LocalMedia

#CreatorEconomy

#EmailMarketing

#NewsletterGrowth

#MediaBusiness

#CommunityBuilding

#Cleveland

#DigitalMedia

#Entrepreneurship

Why do legacy media companies earn more ad revenue even when local newsletters often have higher engagement? In this conversation, Justin Moore explains the disconnect and outlines how modern local media operators can position themselves as high-value partners to advertisers.

Topics include how to pitch sponsorships without racing to the bottom on price, why Instagram and video content carry outsized value for local businesses, and how custom, goal-based proposals outperform generic ad packages. Justin also shares tactical advice on outbound pitching, video proposals, and identifying the right advertisers to target.

This episode is designed for local publishers who want to move beyond low-dollar ads and build a real sponsorship business.

Guest: Justin Moore

Website & Book: https://sponsormagnet.com/

Podcast: Sponsor Magnet Podcast

Live Event: https://sponsorgames.com/

Use code “TJ500” for $500 off

Subscribe to the Weekly Newsletter:

https://www.localmediahq.com/subscribe 

Join the Community (Discord):

Connect with TJ, share ideas, ask questions, and be part of a growing creator & media community

👉 Join here: https://discord.localmediahq.com/

Follow My Journey

Twitter/X: https://x.com/TJLarkin23 

Instagram: https://www.instagram.com/tj.larkin 

LinkedIn: https://www.linkedin.com/in/tjlarkin1 

Website: https://tjlarkin.com/ 

Work With Me

For brand partnerships, sponsorships, and business inquiries:

[email protected] 

#LocalMedia #NewsletterBusiness #Sponsorships #MediaMonetization #CreatorEconomy #LocalAdvertising #JustinMoore #SponsorMagnet #DigitalPublishing #MediaStrategy

Dan Oshinsky joins TJ Larkin to unpack what it really takes to build a sustainable newsletter business in 2025 and beyond. With over a decade of experience leading newsletter strategy at major media companies, Dan explains why newsletters are still early and where the biggest opportunities exist today.

The discussion covers niche selection, local newsletters, audience trust, and how creators can combine newsletters with social media, events, and community building. Dan shares real examples of newsletter operators who turned small audiences into six-figure businesses by focusing on value, consistency, and relationships.

If you’re struggling with ad sales or unsure how to monetize your newsletter, this episode offers practical advice on building partnerships, following up with advertisers, and creating long-term revenue instead of chasing quick wins.

Guest: Dan Oshinsky

Website & Newsletter: https://inboxcollective.com/

Newsletter Advertising Playbook: https://inboxcollective.com/buy-the-playbook

Subscribe to the Weekly Newsletter:

https://www.localmediahq.com/subscribe 

Join the Community (Discord):

Connect with TJ, share ideas, ask questions, and be part of a growing creator & media community

👉 Join here: https://discord.localmediahq.com/

Follow My Journey

Twitter/X: https://x.com/TJLarkin23 

Instagram: https://www.instagram.com/tj.larkin 

LinkedIn: https://www.linkedin.com/in/tjlarkin1 

Website: https://tjlarkin.com/ 

Work With Me

For brand partnerships, sponsorships, and business inquiries:

[email protected] 

#Newsletters

#LocalMedia

#CreatorEconomy

#AudienceBuilding

#EmailMarketing

#NewsletterBusiness

#MediaEntrepreneur

#DigitalPublishing

#AdSales

#InboxCollective

Matt Moody breaks down how he built Salina 311 into a “community intelligence platform,” reaching over 30,000 members in a town of about 60,000, and generating north of $500,000 in annual revenue. 

Instead of treating it as “just a newsletter,” Matt explains how multiple distribution channels (email, web, Facebook, SMS) and heavy automation shaped the growth engine, plus why he focuses on objective community data to earn trust. 

They also dig into monetization: paid memberships, limited ad inventory with rising rates, sponsored coverage for teams/events, and a self-serve ad approach that increasingly drives inbound demand. 

Guest info: 

Matt Moody

Fractals Network: fractalsnetwork.com

Salina 311: salina311

Events platform: events.salina311.com

Wilmington community example: communitydashboard.org

Subscribe to the Weekly Newsletter:

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Join the Community (Discord):

Connect with TJ, share ideas, ask questions, and be part of a growing creator & media community

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Website: https://tjlarkin.com/ 

Work With Me

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#LocalNews #NewsletterGrowth #CommunityBuilding #MediaBusiness #MembershipModel #LocalAdvertising #CivicTech #Automation #SMSMarketing #EventsMarketing