How do I close more local newsletter ad sales?

I spent nearly twenty years in insurance before this. The biggest lesson carries straight over to newsletter ads.

"Good salespeople crush average salespeople selling the same thing."

In insurance you're selling the same policy as everyone else. Some people crush and some people suck, and a lot of the difference is presentation: how you talk about what they're getting.

What should the first call sound like?

Short pitch, then listen. Describe the audience: big, engaged, a unique model. Then ask what they need and what they're thinking. Tell them you'll work up an option or two and get back to them. Don't commit to a price on the first call.

How do anchoring and free add-ons work?

Put prices on the extras, so buyers see that social media costs money. For example, one social media post for $50, three for $150. Then on the phone:

Tell them you'll just include the social posts for free. They thought they were buying one newsletter ad and now they get social posts too. Who turns that down? The numbers are examples, the concept is what matters. Only do it for bigger purchases where you're raising the price, not on low launch prices.

What's the insurance bundling trick?

Quote the highest-ticket bundle first. In insurance, someone wants auto and you bundle in life: "we're giving you this extra coverage, it's only $200 a month," which is really $170 plus $30.

• Some people just take it. You sold the bigger package.
• If they push back, you remove the extra and drop it to $170. That's what they asked for in the first place, but now you've helped them and given them a deal.

You win either way. They buy the extra, or they like you more because you helped.

Should I discount to close?

Not off your listed price. When a spa wanted our six-month package at the listed price, my advice was to say "let's do it" and not discount it. Don't sell yourself short.

Why do local ad deals take so long?

They're interested, they know it's a good idea, and they're still hard to pin down. Sometimes the budget is tied up: they're in a three-month contract with someone else and have to wait until it ends to pay you. It's a long game. John Apolinar told me on my podcast it usually takes a few conversations, and he follows up to get them to pick a date.

How much does follow-up matter?

It's the whole thing. I don't always follow my own advice here, but follow-up is key, 100 percent.

Don't assume they don't want to work with you because they didn't get back to you. They're busy. There are probably lots of people I'd buy from right now if they reached back out. I mean to deal with it later and it never happens. If they asked again, I'd say yes, book a call.

If you're young and selling to older owners, make that work for you: you're building something in town instead of taking a corporate job, and a lot of owners would want to help their own kid do that. For what to do once they say yes, see the checkout flow.