What is the best way to monetize a local newsletter?

The better play is to own a business you can advertise in your own newsletter. I say it on my podcast all the time, and nothing I've seen since has changed my mind.

Why not just sell ads?

You can. If you're good at sales and understand the game, ads can get you to decent money, low six figures once you're at scale. I've had a guest on the show clearing well over $10,000 a month from ads alone.

But it's a grind, and it has a ceiling. Every ad dollar requires the same steps: find the advertiser, pitch them, agree on a price, get approval, deliver, then prove it worked so they renew.

You're dealing with small businesses that will probably nickel and dime you. Monetizing a local newsletter through ads alone is a pain in the butt. The legacy media model was ads, and a lot of people in media still haven't caught up: you can make money from ads, but you can't rely on them.

When you own the advertiser, every one of those steps disappears. The newsletter becomes free, owned distribution for your other business.

"Making money from advertisers alone is possible but very hard."

What kind of second business works?

• A local service business that sells to the same people reading your newsletter. A realtor sells real estate. An insurance agent sells insurance.
• An event company, if your readers love events.
• A marketing or AI agency that sells to the same local businesses reading your newsletter. More in the agency play.
• A storefront. One small-town operator on my show made his coffee shop the title sponsor of his newsletter, so its logo sits at the top of every email.
• Video or creative services. Operators who are crushing Instagram tend to make more from video services than from the newsletter itself.

For me, the product is the agency side: AI and digital marketing plus ads. When I started, I told a broker I didn't think it would pay off at all short-term. I hadn't sold a single ad yet and was still losing money. It's a long game.

If you already have a local business, this is a killer opportunity. Start there.

Does this work in a small town?

Especially in a small town. When few advertisers can pay real money, the owned-business path matters more. In a town of about 30,000, a newsletter is worth doing even if it never makes much on its own, because you become the person who provides value to the whole town. The second business turns that into money.

It works because people care where they live. Most email newsletters get 25% open rates if they're lucky, and 30% to 40% is considered very, very good. Local newsletters tend to beat that.

Isn't media supposed to make money directly?

It doesn't have to. Everyone says ads in newsletters are hard to sell. What if that's not how you're monetizing? If you're selling your own product, the media is about trust and authority, and you use that to make money elsewhere.

"I'm making money indirectly from media, not directly. I'm kind of betting everything on that concept: trust is going to be what grows."

My podcast hasn't earned me direct money. It's been worth it indirectly.

Can a local newsletter reach $10,000 a month?

Yes, but not easily. Someone asked me this about a list of 20,000 to 40,000 subscribers. You need cold email, a sales process and Zoom calls, or someone who does that for you. Get in front of the big players in your city or state. That's the easiest route to $10,000 or more.

And sell more than newsletter ads. Build a full website, then stack what a business can buy:

• Sponsored articles on the site, with a backlink.
• A directory built for AI search, with a paid featured section and better profiles so businesses are more likely to get cited. More in directories for AI search.
• A job board, with featured jobs also promoted in the newsletter. See local job boards.
• A deals section at the bottom of the newsletter.

Social matters here too. A big, quality Instagram following is your proof that you're legit, and lots of operators crush it by DMing businesses on Instagram.

Should you still sell ads?

Yes. This is about which is the better primary play, not either-or. Run ads, sell sponsorships, build the survey offers. Just don't make advertisers your only plan.

One more thing I tell listeners when I interview an operator who's far ahead of everyone: don't copy what he's doing exactly. Look at the breadth of what's possible, then pick what makes sense for your market and what you actually want to run. For the mechanics, see what a back-end offer is.