Is it too late to start a local newsletter?

You think you're late, but you're early.

I started about a year before some of the people asking me this, and others started a year before me. Every one of us is still early.

Why does it feel crowded?

Because of where you're looking. If you follow newsletter people online, you're hyper aware of a space that roughly 99% of people have never encountered. That number is my gut, not a study, but the point stands.

"Digital marketing, email, local newsletters, selling your own products are foreign ideas to 99 percent of people."

Twitter especially is a bubble. Go ask a local business owner whether they know you can hire someone in the Philippines for a third of the price of a US hire. Most don't even know that's a thing. They definitely don't know about local newsletters.

It felt the same with crypto and AI. People felt late and were early. The scarce thing isn't opportunity. It's curiosity. Most traditional operators aren't curious about new models like email and digital marketing, and that's the advantage.

Are good towns still open?

Yes, a lot of them. I've looked up places that would be perfect for a local newsletter, places you'd have heard of, and there's nothing there. When I searched a cluster of wealthy suburbs, nobody was doing it. That's a land grab, and it isn't a rush yet.

Towns of 20,000 to 50,000 that have nothing, or one bad site, are a goldmine. Small-town local is so fragmented that it doesn't matter if one player does really well somewhere. You only need about 5% of your market to be crushing it. And in a small town, you just cover everything.

If you find an open town and you want to keep it, move fast. My suggestion for a wealthy suburb was to put $5,000 or $10,000 into ads, blow the list up quickly, scare off competitors and become somebody.

Doesn't AI make it too easy for everyone?

It's getting easier, and that's exactly why now is the time. With AI and tools like the one I'm building, it's only going to get easier. Build the audience now, so you're already the local media company when everyone else tries.

We're figuring it out and learning now. By the time it's easy, we'll know everything to do. Use AI as much as you can, but stay as local and human as you can. Pure-AI local brands already exist, and they're terrible.

Copycats are coming too. One of my clients emailed me because someone copied them: same location, same everything. That's going to keep happening. Most of them half-ass it and bail quickly. But there will be a lot more of it, because tools like mine make a quality newsletter something you can do in about 10 minutes. That's one more reason to get there first.

Should I worry about the local paper?

Not much. Legacy players are far behind on tech, delivery, strategy and mindset. Picture someone making $400,000 a year working 10 hours a week, with a team that's been there 15 years. Some kid shows up with a better way that costs money to figure out. You'd say no too. That's the innovator's dilemma, and local media has it worse than most industries.

They can even help you. When they break a story, you credit them and give it to readers in the format they actually want.

Is local still less competitive than national?

By a lot. Breaking into a national niche like entrepreneurship, AI or tech is very hard. Local has way less competition, especially if you put real effort in. See local vs. national.

The timing is on your side for a bigger reason. For 15 to 17 years, since smartphones and social media, life has swung toward staying home on your phone. COVID pushed it further, and AI could make it worse. I think the pendulum swings back toward in-person and local.

When is a town actually taken?

It can be. A specific town can have one entrenched competitor. In my Texas market there's a competitor that isn't great but is close enough; outside Texas I think most people have almost no real competition. Suburbs of big metros get crowded enough that businesses tell you four other newsletters pitched them recently. Check your market, not the internet:

• Who already publishes there, and do people actually read it?
• Are local businesses being pitched by several outlets?
• Is there a nearby city or county nobody covers well?

What matters more than timing?

Effort. The bottleneck is commitment, not crowding. I've interviewed five or six local media operators making six figures, some part time. Almost nobody is putting real effort into this, including me.

"If you're smart, run with it, go all in, put in true effort."

The downside is also gentler than most businesses. I built an AI startup before this. Everybody loved the idea and we couldn't get it over the finish line. With a local newsletter, failure can still mean an audience of 10,000 or 15,000 people paying attention to you. By September 2025 I'd done this 14 times. It works.

For the right business owner, about $10,000 of ads is a small risk. One I explained it to put it this way: either it doesn't work and he lost $10,000, or it works and he's a leader in his community with a huge audience. Just set short-term expectations low. Six months in, with about 15,000 subscribers across our two home-area newsletters, I hadn't been recognized once. An operator who has half his town reading took five years to become the local celebrity.

Do I regret waiting?

Yes. I first heard about this model around 2021 or 2022, thought about it, and put it on the back burner. I wish I'd started then. I'd be so much further ahead.

I stumbled into it anyway. I'm not a journalist. I saw entrepreneurs doing it on Twitter and started one as a side hustle for my wife while I was running that AI startup. Then friends wanted to do it too, which pushed me to go all in. If you're thinking about it, do it now.