How do I start relationships with local businesses before pitching them ads?

The easiest ad sale is to a business that already likes you. That takes giving before asking.

Why give first instead of pitching?

Business owners are buried in cold pitches. Somebody on email or social promising 50 calls a month, and the owner has no idea if that person is real, capable or a fake profile.

Doing something for free first proves you're serious and that you can actually do the thing. It also triggers reciprocity. Robert Cialdini's book Influence from the 1980s covers it: when you give something to someone, they want to give back.

"the world is too used to pitches essentially now, like going directly to somebody for what you want, whether it's an email, whether it's in person, whether it's a TV ad, like whatever it is. Just go roundabout. Go provide value first and sell them later, right?"

That doesn't mean everyone signs up to give you money for ads. It puts you in their corner, and it can lead to a connection or a sale later. Think of a commercial real estate agent. He's the eighth real estate pitch an owner hears that week. Show up with "can I broadcast your business to the community for free?" and who says no to that?

What can I give away?

• Press releases. A podcast guest tip I hadn't thought of. When a business sends one, run it. You probably would have anyway. Then tell them: "This went out to 26,000 people." Now they're curious about your reach and dig into you.
• Free features. Feature random local businesses in the newsletter, then DM them to say you did. Short-term free help builds the audience you monetize later.
• A podcast interview. I posted in my HOA group that I'd interview local business owners for a podcast tied to my newsletter. Four people responded to that one post.
• Free ads in an empty slot. See why I run free ads.
• A free directory listing. A digital marketing operator I heard from gets ignored pitching AI or marketing services, but owners reply when he offers a free listing in a local directory and asks them to confirm their details. Then he cross-sells. A directory page costs nothing to give away. Newsletter space is limited, so I'm stingier with that.

The order I like for a new newsletter: have the owner on your podcast for free, promote them for free, then add a free ad on top. By then they like you, and they're far more open when you ask about their own problems. Do it with consumer-facing businesses you like. A free ad for a B2B business is wasted on a consumer list. Home services are ideal, because roofers and insurance people see their competitor in there and start asking questions.

How do I reach owners directly?

Instagram DMs from the brand account. Your call to action is about collaborating. Asking a stranger to buy ads before you've ever spoken is the wrong angle. In one day I heard from two different operators that DMing was working.

John Apolinar of Scottsdale Scoop told me on my podcast he spends about 10 minutes a day on DMs. His script says he runs the newsletter, has an audience of 5,000 locals and would love to collab or feature them. His pipeline went from 2 or 3 conversations to about 15 in two weeks, and most replies turn into in-person meetings. Nick Hageman in Kansas City DMs businesses and event accounts from his brand account and often reaches a recent grad running their social.

I DMed eight of twelve local custom home builders, then stopped on purpose so Instagram wouldn't ban me. Go one business type at a time.

Phone calls work the same way. Call a well-known founder as "another business owner who'd love to connect" and they have no reason to give you time. Call as the founder of a local media brand who wants to feature them with videos, social posts and a newsletter mention, and they say yes. You get in the door because you're giving them something. That works even when the brand is new and small.

How do I reach the big companies that ignore cold email?

The advertisers who come to me on their own are usually the ones I don't want: the bakery, the notary. The ones I want are the local hospital, the big water park, the big companies. They'd probably advertise. They just don't know I exist.

I asked a chamber of commerce leader how to reach the people who decide where those big marketing budgets go. Her answer: they won't take your call or read your cold email. Even an introduction won't make them care. You have to meet them where they already are.

• Join your chamber, or several, and go to their events.
• Go to any business owner events in your town.
• Go to city council and economic development meetings. Custom home developers are some of the best advertisers, and they show up where the city talks about what's being built.

John Apolinar tries to hit at least one chamber event a week, out of around five on offer. The good news is you can pull this off. The bad news is it takes a lot of time. Even if you never meet the hospital's marketing chief, you meet someone who's friends with that person, and they pull you into that circle.

What if the business can't pay?

Don't write them off. Ask for something that costs them nothing: an introduction to business owners they know, or a review.

At a chamber meeting, a pet shelter told me they had no money for ads but we'd be perfect for getting their word out. I said fine, you don't have to pay. Talk to the doggy daycares and other for-profit pet companies, get one to advertise, and I'll write about your pets for free in the section they sponsor. Same idea with well-connected members: I'll run you free if you can get me two real advertisers.

Restaurants are another trade. Many local businesses have customer emails they never use. Offer a free ad if they mention you at the top of their next three newsletters. It costs them nothing. The hard part is getting in front of them at all. A four-location restaurant chain in my area never answered two emails. Plenty of owners aren't email people, so try the phone or show up.

How do I stay in front of them after the first touch?

Once a business is in our world in any way, it goes on our business list. Every two weeks or once a month we email updates on what we're doing at WilCo Guide: new advertisers, open slots, something new we figured out with AI SEO. It isn't a cold email from nobody. They know us, so they open it, and that's where we run our biggest deals.

Familiarity sells. One of the strongest ad sellers I've talked to says over 90 percent of his advertisers already knew the brand before he pitched. His first ask isn't "advertise." It's "follow us and subscribe." A month later he follows up and sells. Andrew Smith of Huntsville Explorer told me on my podcast he features a target brand naturally, thanks them without asking for anything, and circles back in three or four months. His small slots sell at $100 to $250. The $500 to $700 packages are harder without that familiarity. That's why I think social matters so much for ad sales.

Why not just wait for inbound?

Most inbound is from companies with no money, and the legit ones often go quiet after you reply. I've got a bunch outstanding. You can still ask your audience directly: a podcast guest in California posted on Instagram that she was looking for sponsors for an upcoming event, and six businesses replied within an hour. Your readers already know your voice, so write about it in the newsletter too.

Then persist. Small business owners are so busy that they often don't reply even to vendors they want. I know because I was one.