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 you go four or five months with no ads and then start, it feels like an intrusion.

The reader isn't paying for this, and I'm not volunteering. The money comes from advertisers. Free ads from day one teach that without saying a word.

Why give ads away instead of leaving the space empty?

• It sets expectations. Readers get used to an ad in that spot.
• It creates FOMO. Real businesses in the issue show other businesses that advertising here is normal. When a prospect subscribes and sees a bunch of sponsors, you look like you're doing well.
• 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.

I've run ads for free a lot, in the past and still now, for tiny businesses that would never pay. Why wouldn't I help the banana bread lady put an ad in when the space would be empty?

It's not the end of the world if an issue goes out without one now and then. I've done it. Just aim for an ad in every issue.

Who should get the free ads?

1. Small local businesses. They fill the slot and become pipeline. A home baker who messages you gets a free classified, not a multi-thousand-dollar annual pitch. Know who can afford what before you pitch.
2. The big players. Offer a free placement to the business others see as the big dog, so competitors think, "if they're in there, we want to be in there." Anybody in town with power: run an ad for them free and get on their radar.
3. Restaurants. The businesses readers most want to see are the least able to pay. Feature restaurants free or through giveaways, and charge the dentist and the insurance agent.
4. Friends and partners. If you hate selling, give slots to people who can send you value, like a real estate broker whose listings run in your newsletter in exchange for referrals when someone's moving.

Sam Parr has talked about running a Ford ad in The Hustle before he had any advertisers, so other companies figured they needed to be in there too. Doing that without permission is a gray area, and I'm not saying it's right. The clean version is to ask the big name and give it to them free.

Then ask for something that costs them nothing. In their next email to clients, could they mention there's a new newsletter in town that covers everything happening in the area? Early on, what you want most is the word out.

Should I pre-sell instead of giving everything away?

For the right advertiser, yes. Pre-selling means going to them before you have the audience: here's what I'm building, I'm growing 20 to 50 subscribers a day with Meta ads, and I'll hit 10,000 in a few months. Lock in your spot now.

• Charge a discount, around $100 to $200 an ad, until you hit the number you promised.
• Or say they pay nothing until you reach a threshold like 1,000 subscribers.
• Reward early believers with a price lock on renewals, or first dibs on category exclusivity.

For a first advertiser buying three monthly posts, about $200 an ad, around $500 for the three months, felt reasonable to me. One firm rule: don't give away an annual spot. Give away individual ads all day. The annual partnership is what you'll sell later.

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.

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.

Some trades I've done or seen:

• I gave a local gym a free ad for a free month of membership. It got 40-some clicks.
• A podcast guest traded an ad for a laptop repair.
• A trade like an Airbnb stay can become a great story for the newsletter.

Gift cards and giveaways count too. One Instagram giveaway with a new Culver's, with an image I'd call ugly, got about 20x the engagement of anything else we'd posted. Some people worry giveaways bring the wrong crowd. I don't have proof either way.

The bigger idea: the more your brand shows up around town in legitimate places, like your logo all over a First Friday event, the more the whole brand is worth. Putting off the big money now makes the money later easier.

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.