What I Learned From Cold Calling a 20-Year-Old Local Media Company

I decided to cold call a local media company yesterday. What happened next surprised me.

The owner actually picked up the phone and was happy to talk with me.

But what really caught my attention was our 20-minute conversation about his business. Here's a guy who's been running the same operation for over two decades, and the insights were fascinating.

The Business Model That Time Forgot

This owner started his company in 2004 in a wealthy city of 150,000 people. His entire operation is digital:

• Website with local news and information • Daily email newsletter (which he calls an "email newspaper") • Facebook presence for community engagement

Here's the part that blew my mind: He gets up at 3am every single day - seven days a week - to edit and publish 15 stories for his morning newsletter. Everything has to be out by 7am sharp, just like a traditional newspaper.

The guy has 13 employees and reporters working for him, treating this digital operation with the same discipline and schedule as old-school print media.

The Revenue Reality Check

When I asked about advertising revenue, he was refreshingly honest: "Ad money is rough right now, but we have a solid base of advertisers who keep coming back."

This is the struggle every local media company faces. The advertising dollars that used to flow freely to local publications have largely moved to Facebook, Google, and other tech giants.

But he's managed to maintain relationships with loyal local advertisers who see value in reaching his audience. That's not nothing.

The Website That Time Forgot

Naturally, I had to check out his website while we were talking.

It was painful.

The site looked exactly like it was designed in 2004 and never updated. Pages would freeze. The newsletter signup was nearly impossible to find. Basic functionality was broken.

I told him during our call that I tried to subscribe but never received a welcome email. His response? He just laughed and said, "Yeah, we should probably fix that."

The Adaptation Problem

Here's where things get interesting. When I mentioned some basic improvements he could make - better website design, automated email sequences, improved user experience - he seemed open to learning.

But his tone made it seem like he wasn't willing to make any major changes to his business model.

I get it. When you've been doing something successfully for 20 years, why rock the boat?

But here's the reality: This approach is becoming increasingly unsustainable.

Why This Matters for Every Business Owner

This conversation highlighted something important about business adaptation. This owner has built something genuinely impressive:

• Consistency: Publishing lots of content every day for two decades
• Team building: Growing to 13 employees in a single market
• Community trust: Maintaining loyal advertisers and readers
• Work ethic: Getting up at 3am every day shows incredible dedication

But impressive past performance doesn't guarantee future success.

The digital landscape has fundamentally changed since 2004. Reader expectations have evolved. Competition for attention has intensified. Revenue streams have shifted.

The businesses that thrive long-term are the ones that maintain their core strengths while continuously adapting their methods.

The Takeaway

Talking to this owner was like getting a glimpse into a time capsule. His dedication and consistency are admirable. His results speak for themselves.

But it also served as a reminder that staying the same in a changing world is actually moving backward.

The most successful businesses find ways to honor what's worked while embracing what's next. They keep their foundation strong but aren't afraid to renovate the house.

This local media company has a solid foundation. The question is whether they'll adapt their approach before the market forces them to.

Have you encountered businesses stuck in time? What did you learn from the experience? I'd love to hear your thoughts.

How I Can Help You Succeed

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

Discover all these resources and more at localnewsletterinsider.com