Should you buy struggling local newsletters?

It's part of my long-term plan. Solopreneurs launch local newsletters, get them to 5,000 or 10,000 subscribers, and then quit. That's a huge opportunity to buy them up if you know exactly how to monetize them and can find somebody on the ground. A partner and I floated the idea of becoming local newsletter private equity.

To be clear, I haven't closed one of these deals yet. It's a strategy I've been building toward since late 2024, not a play I've already run.

Why will so many local newsletters fail?

Most of the people starting them are side hustlers. They have a job making $60,000, heard about local newsletters on Twitter, and think it's a cool opportunity. They don't have the money or time to go all in. Somebody putting $25 a month into ads in a market has no impact on you if you have scale.

The ones trying to sell ads only are the ones I expect to fail. In late 2024 I guessed a lot of them were making two to five grand a year for 15 hours a week of work. Many bail within six to 12 months because they don't have time to sell ads and have no plan.

"All the people who are trying to sell ads only, um, they are going to fail. Guess what that means? We go buy them up for pennies on the dollar."

I've even said this on my podcast as a warning: if you're starting a newsletter only to sell ads, know what you're getting into. Otherwise you'll get a small but decent following, realize it's too much work, and sell to a roll-up or to people like me. I'd rather you didn't.

Why would anyone sell cheap?

"Some may sell for dirt cheap because they're not making anything and they just want to walk away. Their alternative to selling to us is walking away."

They don't have a social media person, a sales team or good operators. So it's worth nothing to them and a ton to us. There's a guy in my group running one in a small Texas city, working about 10 hours a week for very little money. If somebody offered him five grand, he'd probably take it. Do we even need to pay five grand? Maybe not.

Sometimes it's free. Someone at a newsletter conference offered me his newsletter for nothing, because he was already succeeding in AI and this was too small for him. He asked my plan to monetize it. I told him I hadn't figured that out yet, and I wasn't going to promise something I didn't have ready.

Very few people would buy a 7,000-person newsletter unless they were great at sales. That small buyer pool is why the prices are low.

What does a buyer add?

The pieces the founder never had:

• A sales person or team.
• Social media.
• A local operator on the ground.
• Meta ads to keep acquiring readers.

With those added, the target is a $50,000 to $100,000-a-year asset, and the question I keep asking is whether you could do that almost instantly. I think this is going to happen a lot over the next five years.

What about competitors who launch in your city?

In a good market, expect them. A big city with high-value suburbs will attract two or three competitors in a couple of months. That can be a great thing. Get to scale fast, and the ones who fall behind become acquisition targets once they realize it's not worth their time.

Should you buy a newsletter or start one?

If someone needs three newsletters fast, I'd say acquire one and start two. Always build at least one yourself, because you learn the whole game instead of relying on things you bought. Starting doesn't pay off fast, but you control everything and readers know you from the beginning.

Be careful with cheap lists. I could get you a 15,000-person newsletter tomorrow for two grand. It's going to suck, and it won't be your audience.

What should I check in due diligence?

Open rate first. You can ask for the data in due diligence, and open rate tells you if somebody stole a bunch of emails and threw them on the list. That's pretty easy to figure out.

Also look at what happened when the owner stopped growing it. One guest on my show described a list sliding toward under 10,000 after pausing ads for a few months. That's the decay you'd be buying into. My rule for my own brands is to never turn acquisition fully off.

What about buying old-school local media?

That's a bigger-picture idea, not something I'm doing yet. A lot of traditional local outlets aren't making much money. They pay local reporters around $60,000 to do work AI can largely handle. Take one over, put our model in with AI and Meta ads, and there's a real play.

Their real problem is acquisition. They can create content all day, but with no acquisition strategy they can't grow. If you don't have connections in that space, partner with someone who does instead of starting cold.

Look at their other assets too. A big, well-moderated local Facebook group is worth a lot: you can offer an advertiser one post a month where nobody else is allowed to advertise.

Is the downside acceptable?

Usually. Few businesses fail into something as useful as an engaged local audience of 10,000 to 15,000 people. Even a struggling newsletter is an owned asset rather than a rented lead source.