I recently cold-called a legacy local media company and had one of the most interesting conversations I’ve had in a while.
The owner was surprisingly happy to chat and more open to giving me information than I would have guessed.
Table of Contents
Pioneer Stuck in Time
He’s been running his operation since 2004 in a pretty wealthy city of 150,000 people.
His approach has been all digital from the start—website, newsletter, Facebook content.
Surprisingly, he has never mailed anything, which is unusual since he was doing this at a time when direct mail was very common for local media.
The Daily Grind
The owner has 13 people working for him and maintains an exhausting schedule that would challenge anyone half his age.
He gets up at 3 a.m. every day—seven days a week, he emphasized—to edit 15 stories.
He said he’s been maintaining this routine since the beginning.
He proudly calls his newsletter an “email newspaper.”
Everything has to be published by 7 a.m. sharp, and he treats it exactly the same as an actual morning paper would handle their deadline.
The Revenue Reality
When I asked about revenue, his response was telling:
“Yeah, ad money is rough right now, but we have loyal advertisers.”
It’s a common refrain among local media owners navigating today’s challenging advertising landscape.
The Technical Disconnect
After our conversation, I went to check out his website, and the experience was jarring.
The site looks straight out of 2004 and appears to have never been updated.
Pages freeze, the newsletter signup is nearly impossible to find, and the whole thing feels like a digital disaster.
I told him during our call that I had tried to subscribe and never received a welcome email. He just laughed and said:
“Yeah, we should probably fix that.”
Paradox of Success
He seemed open to learning but honestly didn’t sound interested in making any real changes.
I understand the reluctance—if something has worked for 20 years, why fix it?
But this business model is getting harder every year.
What’s particularly interesting is the math behind his operation.
Thirteen employees for a town of 150,000 seems excessive by today’s standards. However, he must be generating at least low seven figures annually to afford 13 local employees in an expensive city.
Conclusion
These legacy local media companies really need to evolve, or they’re going to get crushed by the changing digital landscape.
It was fascinating talking to someone still running things exactly the same way they did 20 years ago, but I’m not sure they’re ready for where the digital world is heading right now.