Should I run free ads in a new local newsletter?

"I don't care if you don't have somebody paying you for ads, go offer them for free and put them in the newsletter, because you want to train your audience to know that this is a newsletter that has ads."

We make money from ads. The reader needs to see ads as native to the product from the start. If your first ad shows up months in, it feels like an intrusion.

Why give ads away instead of leaving the space empty?

• It sets expectations. Readers get used to an ad in that spot.
• It builds relationships. The business sees its ad live and starts paying attention to you.
• It creates examples. You can show prospects what a real ad looks like in your newsletter.
• It costs you nothing. There was nothing there anyway.

"Why wouldn't I just help the banana bread lady put an ad in when there's nothing there anyway?"

I've run ads for free a lot, in the past and still now, for tiny businesses that would never pay.

Who should get the free ads?

Two groups, for different reasons.

1. Small local businesses. They fill the slot and become pipeline.
2. Bigger businesses. Offer them a free placement so competitors and other bigger players see it and think, "if they're in there, we want to be in there." That's a well-known tactic, and it works because nobody wants to be the only one missing.

Should I make a classified section?

Yes. In 2025 I formalized this as a classified section at the bottom of the newsletter: basically ads at the bottom, free for now. Naming it means it can switch to paid later without changing anything for readers.

When free requests start competing with paying advertisers, move the free inventory below the paid slots instead of cutting it. A standing section that's always there and always the same is something readers come to expect.

A partner and I also talked about a tiny paid version, like the old paper where you could pay $20 for a small message in the back, for businesses that can't afford $250. Ten of those is $200. I'm honestly not sure that's worth the effort.

When should I stop giving ads away?

When people start wanting to pay. It's getting harder for me to give ads away because people actually want to pay now. That's the signal the free phase did its job. I don't have a free-to-paid conversion number to share.

What about trading ad space for services?

Some people in my group say trades devalue what you charge. I don't think there's a right or wrong answer, and I'm up for trades in general, especially early. Everybody starting out needs proof, relationships and content. A trade like an Airbnb stay can become a great story for the newsletter.