Why Starting Your Local Newsletter Today Beats Waiting for AI

The clock is ticking on one of the biggest opportunities in local media.

When Jas Singh launched the Winnipeg Digest just over a year ago, he wasn't first to market. Local news had existed for generations. But he was early enough to build something remarkable: 25,000 email subscribers, 50,000 Instagram followers, and a business generating six figures in revenue after just one year.

The window for replicating this success is closing faster than most people realize. Not because the model doesn't work, but because those who start now will have insurmountable advantages as technology evolves.

Let's address what everyone's thinking about: artificial intelligence. Yes, AI is going to transform content creation, including local newsletters. But that transformation creates opportunity for those positioned correctly.

"I think it will have a huge local impact on media, but that's why I think it is more important to build up that audience right now," Jas explains. "When AI is at that point where you click a button and it generates the local newsletter for tomorrow... you already have the local audience that needs that product."

The critical insight here is that AI will eventually make content creation much easier, but audience building will remain challenging. The winners won't be those who can create content most efficiently—they'll be those who already own the audience relationship.

If you're debating whether it's too late to start a local newsletter in your city, Jas's experience is instructive.

"At this point, if someone were to start a newsletter in Winnipeg, I can confidently say they're way too behind for them to be able to compete with me," he states. "They would have no angle or they would have to go a completely different angle from a local media standpoint to acquire the same subscribers."

This is the fundamental reality of audience building: once someone subscribes to a comprehensive local newsletter, they have little incentive to subscribe to a similar product. The first comprehensive newsletter in a market creates a moat that becomes increasingly difficult to cross.

Beyond audience building, there's another crucial advantage to starting now: learning what works.

TJ Larkin emphasizes this point: "We're doing this now. We're figuring it out. We're learning. And then by the time it's easy, we know everything to do."

This operational knowledge—how to run effective ads, what content resonates with subscribers, how to sell sponsorships, which partnerships yield results—becomes invaluable intellectual property that can't be easily replicated, even with advanced AI tools.

For those who successfully build one local media operation, the future holds even more opportunity. As content creation becomes more automated, expansion becomes more feasible.

"In two years when this whole AI thing does end up happening and I can build a newsletter for any city in five to 10 minutes... as someone who has already built out a local newsletter, I have such a competitive edge," Jas points out. "I already know what to do, how much money to spend, how to run the ads, what ads to run, how to grow a social following."

This means established operators will have the playbook and resources to expand when technology enables it, while newcomers will still face the steep learning curve of audience building and monetization.

While the opportunity is urgent, the execution should be measured. Jas cautions against trying to grow too quickly with massive ad spend.

"I almost disagree with people that say we're going to spend 10 grand a month and wrap this up to 10,000 people in the first month," he says. "You're front-loading your growth... but you also built a brand in a month, and the downside to that is no one really knows you."

Instead, he recommends a steady pace—perhaps $100 daily on ads—that allows you to refine your content, build genuine recognition, and develop multiple channels simultaneously.

The final piece of the puzzle is figuring out sustainable revenue. Jas emphasizes that this is where many newsletter creators stumble:

"The biggest thing that people get wrong is yes, they build the audience... but they just can't figure out how do you even initially monetize this audience."

Without monetization, even the best content creators will eventually run out of runway. That's why focusing on revenue strategies from the beginning is essential for staying in the game long enough to reap the rewards.

The coming AI revolution isn't a reason to delay starting your local newsletter—it's precisely why you should start now. Those who build audiences and operational knowledge today will be best positioned to leverage AI tools tomorrow.

As TJ succinctly puts it, "If you want to do it, do it now."

The opportunity to become the definitive local media voice in your community won't last forever. Will you be the one who seizes it, or will you be playing catch-up to those who did?

Before we dive into this week's insights, I want to make sure you know about all the resources available to support your local newsletter journey:

🎙️ The Podcast - Deep-dive conversations with successful newsletter operators sharing their playbooks and lessons learned | Link

📧 This Weekly Newsletter - Quick, actionable tips delivered straight to your inbox every week | Link

🧠 1:1 Consulting - Personalized guidance tailored to your specific newsletter challenges Link

🚀 Launch Accelerator - A structured program to help you go from idea to profitable newsletter in record time | Link

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