Creative Monetization Strategies You Can Use

Hi newsletter operators,

I’m back! Been quite a busy four weeks or so over here. Took my son to Disneyland, went to the Main Street Summit conference in Missouri, plus the Business of Local conference in Salt Lake before that. And, all the rebranding aspects, which I’ll explain below. Been chaotic to say the least, but glad to be back and focus on local media again.

And speaking of local media, you’ll notice I’ve rebranded everything from Local Newsletter Insider to Local Media HQ (check out the new site here). Still working on colors and logo because Andrew Lane from Design Hacker gave me some killer ideas and concepts right after I built a logo in Canva. Oh well.

Been thinking about switch from “newsletter” to “media” for awhile, and finally pulled the trigger. Just did not seem congruent to constantly talk about the importance of building a local media company, with my brand only mentioning newsletters.

I left the author the same for this one (still Local Newsletter Insider), but will change it for the next one. Make sure you remember it so you don’t think it’s spam next issue.

I also recently announced on the podcast that I’ve opened up a free Discord channel for anyone wanting to learn more from me. Will try to share as much as I can there, and host office hours occasionally (click here for first one on TODAY at 1pm Central). No promises with anything here, since it’s free, but think it could be a cool way to connect with you guys. Here’s the link to join the discord channel.

For those of you who are truly all-in on this space, would highly recommend you join The Newsletter Club that Mike from Catskill Crew runs. So many smart people in the space in there sharing every day. I’ve said it before, but it’s by far the best online community I’ve been in, and it’s not close. Really, you should just be in both. Think of mine as just mostly learning from me, where The Newsletter Club is about community, building relationships, and learning and sharing with others. Check it out here.

New Media Summit (come hang out with me)

February 26-27 in Austin

Another thing that I think most of you should be considering is going to the New Media Summit here in Austin in February. First event was killer, met so many great people in the space, learned a ton. Can’t recommend it highly enough. I’ll be there of course, hope to meet as many of you as possible.

Get 10% off if you use my code TJ10. If you’re going, reply and let me know!

New Media Summit | Feb 26-27, Austin, Texas

The event for founders and creators building the future of media and education. Meet experts in the newsletter, media, and education industry. The conference is coming back to Austin, Texas on Feb 26th & 27th, 2026.

newmediasummit.com

Dads, read this!

For all the dads out there with kids at home. PLEASE, read the book (really a pamphlet) called Family Board Meeting. It’ll take less than 30mins to read. Absolute game changing concept for building real bonds with your kids. I’ve been doing it a for a few years now, and it’s truly life changing, for all of us. Even my wife and daughter had one of their best weeks ever, at home, while we were at Disney.

Trust me, it’ll be worth it. Here’s the Amazon link

Podcast spotlight

Jimmy Farrell - Personal Branding Value of Local Media

Top Three Takeaways

Deliberate growth, then paid acceleration

Jimmy grew from zero to 875 subs organically through in-person community work and light Instagram over 9 months, then introduced Meta ads to push past 10k in less than 8 months, before dialing spend back.

• Monthly spend around $1k a month produced rapid list expansion, yet he paused after hitting 10k subs because additional volume would not immediately change local sponsor pricing.
• Open rates remained around 71–72 percent, while clicks softened when linking to paywalled articles from the legacy media frustrated readers, prompting a pivot to on-site summaries and internal links.
• Instagram engagement improved once he shifted from reposts to short local business owner interviews and shop features that surfaced genuinely new local information.

Local face with insider access

Jimmy is the visible voice of the brand and leverages 31 years in retail real estate to secure credible scoops and context.

• He nurtures relationships with retail brokers and operators, which yields early information his audience values and traditional outlets often publish later.
• He publicly identified the second Trader Joe’s location in the market, reinforcing that the newsletter delivers timely, verifiable utility for locals.
• Routine presence at neighborhood spots and events signals authenticity, which strengthens tips, replies, and word-of-mouth growth.
• Web-only live music guides on Mondays and Thursdays keep readers returning between Friday editions without adding extra sends.

Monetization to fund the machine

Jimmy prioritizes covering acquisition and platform costs, then expanding, while prospecting categories with higher lifetime value.

• He treats sponsorships as fuel for future Meta budgets and software spend, aligning near-term revenue with controlled growth loops.
• Prospecting tilts toward dentists, med spas, banks, and regional brands, using LinkedIn for larger teams and Instagram for owner-led businesses.
• Initial automations handle first touches, but he switches to hands-on follow-up quickly, matching the longer cycles he mastered in commercial real estate.
• PR relationships and chamber-style events provide warmer introductions than cold lists, accelerating conversations with budget holders.

Mike Kauffman - Direct Mail, Events & Ad Tactics

Top Three Takeaways

Build With Serious Operators, Not Tourists

The Newsletter Club exists so builders stop operating solo and compound skills together. Members share proven templates, run weekly calls, and answer fast, which lowers mistakes and CAC for newcomers.

• Kauffman pushes early-stage paid growth to true efficiency, saying, “I want to see you at 10 cents,” and backs it with tested templates that cut waste and speed iteration.
• The community runs on Discord for highest response, paid access filters in committed operators, and members collab in DMs to ship software, ventures, and real partnerships quickly.

Quarterly Mail You’ll Actually Keep

Digital fatigue is real, so he’s launching a physical, quarterly premium that feels like a seasonal field kit, not a printed email. It is story-driven, concrete, and designed to pull readers offline.

• The envelope packs a mini almanac, a personal note, three member-only stickers, and an event invite with two drink tickets valid for 24 hours to drive real foot traffic.
• Pricing is $25 per quarter or $90 annually, a poll saw about 98% approval on roughly 1,500 votes, and a tree is planted for every letter mailed.

Ads and Events That Deliver Outcomes

He sells outcomes, not placements. Success starts with a goal, then a custom plan that de-risks the buy and proves it works over multiple touches.

• Educate locals, bundle four-week runs at a discount, and align to targets like 2% CTR, featured events, or bookings, then renew with clear results in hand.
• Simple, authentic events win. One sold out and produced about $1.3k–$1.5k in ticket revenue, $7k over the bar, and 12 hotel rooms on a Tuesday.

Great reads

Ways Your Newsletter Can Pay Off - That Don’t Involve Reader Revenue or Ads

This article by Dan Oshinksy perfectly explains why I started a local newsletter just over a year ago. And while a lot has changed for me in terms of growing specifically in the local media space countrywide, I still think this is hyper relevant for creators focused locally, and why it makes sense to launch a local newsletter. Helps you create a massive amount of luck surface area.

Read it HERE.

Building a $500k Local News Business

Great article (and podcast) about Lookout Media and how they’re taking a different path than most of us. Which is to have legit journalism content by true local journalists, plus having a paywall. While this isn’t the path that I think most want to take, still a ton you can learn from what they’re doing.

Read it HERE.

Forget Commodity Media; Catskill Crew Hones in on Scarcity

Great article here about Mike from the podcast above. Read about him and what he’s doing for a traditional media writer and not someone deep in our local niche.

Read it HERE.