Hi there 👋🏼 I'm Price.

I’m building a roofing company from scratch in my mid-30s and documenting the whole process.

Watch me succeed or fail.

I teased "marketing and local newsletters" at the end of last issue and honestly I've been thinking about this nonstop for weeks. I went down a rabbit hole that I think might end up being one of the most important strategic decisions I make this year.

That's a big claim, I know. But hear me out.

If you run a local business; roofing, HVAC, plumbing, landscaping, whatever...you already know that online advertising has gotten wildly expensive. Google Ads, Facebook, Instagram...the costs have gone up because you're competing against national brands and big lead gen companies with deep pockets. A local roofer in San Jose is bidding against national brands spending hundreds of thousands a month on the same keywords. Most small businesses frankly can't compete. So...

Your other (now mandatory) option is social media. Having a Facebook page or Instagram gets your local business seen in the community and it helps, sure. Some businesses do really well at this but organic reach on those platforms is basically dead unless you're putting out viral content every week. And even then, you don't own that audience. The algorithm changes or your account gets shut down tomorrow and your posts go from reaching 5,000 people to 500, or no one.

You're renting attention on someone else's platform. Which if you think about it is kind of a terrible position to be in.

So what do you do?

A few weeks ago I stumbled onto this world of local email newsletters and I haven't been able to stop researching it since.

The concept is pretty simple: someone in a city or community starts a free email newsletter that curates local events, restaurant openings, things to do, community happenings....basically everything going on that people want to know about. No politics, no crime, not the news. Just fun things for people and family to go do every week.

A weekly (or bi-weekly, or 3x per week) guide to your city that lands right in your inbox.

It actually sounds awesome (I would read that) and also sounds almost too simple. But the numbers behind these things are kind of insane.

I've been researching a handful of operators who are crushing it with local newsletters, and I want to walk through a few of them.

Naptown Scoop — This is a local newsletter for Annapolis, Maryland, run by a guy named Ryan Sneddon. He has no journalism background—he's an engineer. He started it in 2020 and now has over 23,000 subscribers in a city of about 40,000 people....I'm sorry....what?! That's more than half the town reading his newsletter. He did between $200-300k in revenue last year, mostly from local businesses advertising. His team is small, with one full-time assistant and a handful of part-timers.

Oh, and he also started a luxury portable bathroom rental company (for weddings and events) that he basically launched and grew by advertising it to his own subscriber list. But I'll come back to that.

Catskill Crew — Founded by Michael Kauffman in the Catskills region of New York. Launched October 2023, now at over 40,000 subscribers. It's one of the best branded newsletters I've seen, and highly curated. He sends once a week and has built this into way more than a newsletter. He runs community events, sells merch, created a Catskills-themed Monopoly board game, sells discount coupon books for local businesses, and is building what he calls a "local holding company." I'll share his actual revenue numbers below.

Winnipeg Digest — Run by a 23-year-old named Jas Singh. Hit 16,000 subscribers in eight months, now past 40,000. Sends 3x per week with 50+ events per issue. His model is $10,000 annual advertising packages with industry exclusivity...meaning only one roofer, one realtor, one dentist, etc. He did $60k in revenue in his first two months of actually monetizing. And, (this is the part I love) he launched a Christmas lights installation company off the back of his newsletter audience. A service business, built on local newsletter trust.

What's Up Edmond & What's Up Arvada — Run by Matt Schoepflin and his wife, across two different cities (Edmond, Oklahoma and Arvada, Colorado). Same model, different markets. They prove that the template is repeatable. Each has about 7,000 or so subscribers and they actually just sold one of the newsletters. Pretty awesome.

Every one of these is on Beehiiv (same platform I use for The Rally). Every one focuses on events and community -- not news, not politics. And every one of them has open rates between 50% and 70%.

For context, the average email open rate across all industries is somewhere around 20-25%. These newsletters are getting 2-3x that because people genuinely care about what's going on in their community. It's something they actually want to read.

That trust turns into ad revenue, because local businesses naturally want to get in front of that audience. And it's a really easy pitch—"You'll be the only [roofer/dentist/realtor] in front of 15,000 local inboxes every week." In fact, a lot of this ad revenue is organic from businesses reaching out to you.

Ok so here's where it gets really interesting.

The general math on subscriber acquisition is somewhere between $0.50 and $1.00 per subscriber, mostly through Facebook ads. Some operators (like Catskill Crew) are getting subscribers for as low as $0.20 because the targeting is so specific and local.

On the flip side, each subscriber is worth roughly $10-$12 per year in ad revenue.

That's a 10-20x return on acquisition cost. I honestly don't know where else that kind of ROI exists.

Now, how much money can you actually make from one of these?

Here's last month's revenue from the Catskill Crew:

$32,100. In February. From a local newsletter about things to do in the Catskills. (see the original tweet breakdown post here)

Annualize that and you're looking at almost $400,000 a year. With subscriber acquisition costs that probably total less than what most roofers spend on Google Ads in a quarter.

I mean...what are we doing?

So you're probably wondering why I'm sharing all of this instead of just quietly going and doing it.

Well, I told you from Issue #1 that I'd show you everything. So here it is.

I'm going to start a local newsletter for Santa Cruz, and South San Jose.

Not as a side project. Not as a hobby. As a core piece of Rally Roofing's marketing strategy. Maybe the most important piece.

The logic is honestly pretty straightforward:

I build a trusted, community-focused newsletter that curates events, restaurant openings, things to do, and local happenings for South San Jose. I make it something people actually look forward to reading. I grow the subscriber base by spending money to get customers for years, instead of burning money on expensive leads that I'd get one touchpoint with, and who may not convert.

Then, I get local businesses to start paying to advertise. Restaurants, gyms, dentists, realtors—everyone who wants local eyeballs and is tired of throwing money at Google. Although I will be a little picky on who I work with because the ads need to fit the vibe of the newsletter.

Then, of course, Rally Roofing advertises in its own newsletter. For free. To a locally-trusted audience that opens the email at a 50-70% rate.

Let that sit for a second.

Instead of spending 5-8% of my revenue on marketing (roofing industry standard), I have a marketing channel that people actually want to read, that builds community trust, and that other businesses are paying me to be a part of. My marketing spend doesn't go to zero, it goes negative. I get paid to market my own business.

That is not normal! And I'm honestly giddy about it.

It ties directly into the Rally philosophy too. The whole brand is about speed, communication, and doing things differently. Owning the local attention in my market through a newsletter people love? That's as Rally as it gets!

I know, I know. You're building a roofing company, writing this newsletter, waiting on a license, and now you want to start another thing?

Totally fair. Here's my thinking:

First, I'm still in that pre-license limbo. I can't really dive into roofing work yet. I figure this is exactly the kind of foundational stuff I should be building right now while I have the time.

Second, this isn't something that produces results next month. It's a 1 year+ play. I'm planting a seed now that I believe will become my number one marketing channel within a year or two.

Third, and this connects directly to Issue #4...this is where the AI automation stuff actually applies. I'm building an agent that can scrape local event listings, aggregate community happenings, and draft the newsletter content. I still review everything, curate it, and make sure it feels authentic and personal. But the heavy lifting of finding and organizing 25+ weekly events? That's exactly the kind of repetitive task AI agents like Openclaw or Manus are built for.

I don't want to oversell it. Building community trust takes work and real real care, and I'm not going to automate the soul out of this thing. But I think I can get the research and assembly piece automated enough that it goes from being a 4-5 hour per week commitment down to maybe 1 hour of curation and personal touches. (the newsletter guys reading this are shaking their heads)

This scales. That's the part that really gets me.

Every market I ever want to operate Rally Roofing in, I can launch a local newsletter first. San Jose, Santa Cruz, Monterey, Carmel...each of those communities has its own character and events scene, and each one could support its own newsletter.

The playbook becomes: enter a new market, build the local newsletter, build the audience, build the trust. When Rally Roofing shows up in that market, people already know us. We're not some random company knocking on doors, we are in a trusted local newsletter they look forward to every week.

The Catskill Crew model of building a local holding company around the newsletter audience, and using that trust to launch and support other local businesses? That's something that I get fired up about.

Look, it's a fun idea that I think is smart. Like I mentioned above I have a lot on my plate and I don't know if I'll get there. But I want to! The playbook exists because people are already doing it.

I'll start sharing progress on the local newsletter alongside the Rally Roofing updates.

License application is in and processing and I'm studying for the license test. The website is close to done. And I've got some more marketing ideas cooking that I'll share soon.

If you run a service business, I want to know - what does your marketing look like right now? What's working, what's a money pit? Reply and tell me. I read everything.

Talk soon.

-- Price

P.S. -- If you want to explore starting a local newsletter in your market, the podcast "Local Newsletter Insider" by TJ Larkin is a goldmine. Also check out Naptown Scoop, Catskill Crew, and Winnipeg Digest to see these in action.

P.P.S. -- New here? Issue #1 has the full backstory. Fair warning: crypto collapse, emergency C-section, lots of figuring out life.