Is cold email worth it for selling local newsletter ads?

"For those in just one location, I think cold email is probably just not worth it. The amount of time, effort, cost to do all of that, you're just not going to get enough of a response."

It may make sense for us, because we can run it across many locations at once. For one newsletter in one town, your hours are better spent on the phone.

What happened when I tested cold email?

Not much. Here's every test I've run:

Test	Result
6 fully custom emails to local owners, about 5 minutes each	1 reply, and they never followed up
25 fully custom emails to high-value businesses, five in each of five industries, a couple of hours of work	1 reply, from a custom home sales guy with no say over marketing
464 emails to insurance agents for my software, almost two months	3 replies, 1 customer. I decided to shut it off.

Emailing and live-chatting businesses through their websites went nowhere too. The owner never sees it. Nobody of importance sees it.

Why does the phone work better?

Everyone I've talked to who does this well gives the same advice: pick up the phone. Call, show up at their office, go to networking events. Small business owners are used to ignoring anything that comes in cold and digital. When I first said this on my podcast, I admitted I hadn't succeeded at local ads yet because I hadn't done that part myself.

"The path to success with cold is phone calls. That's it. At least for now"

A few reasons it's easier than it sounds:

• These are small companies. You're not trying to reach an executive. The receptionist answers and the owner is sitting right behind them. No month-long wait for a calendar slot.
• Nobody yells at you. You're calling businesses, not consumers.
• Most people won't do it. If you'll cold call and get good at it, you have something 99% of people don't.

The call has one job. Most owners don't know what a local newsletter is. If you say "we have a local newsletter with all these subscribers," they'll ask what a local newsletter is. Get them curious enough to say "show me." Spend half an hour to an hour a day on it and expect a lot of unanswered calls. My target for a caller was one lead a day.

Owners are also buried. I ran a small business with up to 15 employees. The number of vendors I wanted to work with and never replied to, just because I was too busy, was huge. I'd wait for them to follow up. Silence usually isn't a no.

Who should I contact first?

High-value businesses only: roofers, custom home builders, med spas, insurance brokers. Start dead simple. Google "[your town] realtors," open their listing, call the number. I ask Perplexity for phone numbers of roofers or med spas in each town we cover and save one list per industry. Hold off on Apollo, auto-dialers and automated messages until manual calls prove the offer.

Also go after businesses already paying for ads. Another operator I follow scouts the print ads, coupon books and ad libraries to find businesses that already budget for local attention. They don't need convincing that advertising works, only that you're a better place for it.

When can cold email actually work?

When it's paired with calls, done at volume, or both. Other operators are getting results I haven't:

• John Apolinar of Scottsdale Scoop told me on my podcast he closed three sponsors in one week with cold email, while less than 30% of the way through his list.
• I heard second-hand about a local operator who scrapes Google business listings into a cold email campaign and had closed $2,200 in ads that month. Simple stuff, and it scales by location.

The trick that makes email work is the phone. Calling people you've emailed is gold. "Did you get my email?" is the whole call, and it helps you get past the gatekeeper. Being local matters too. Most pitches those owners get come from out of town, and you can show up.

If I hired a salesperson, I'd have them hit the same business three ways: cold email, a phone call, then an Instagram DM. For WilCo Guide, I'm planning broad AI-agent outreach to local businesses. For software like greetform and lightbreak, it'll be much more targeted. So many people are put off by how many things you have to set up for cold email. That's what AI is for. That plan has no results yet.

If I do send cold email, what are the rules and tools?

These are the guardrails I set for our outreach system:

• About 20 a day, from a warmed-up secondary domain. Never your newsletter's sending domain.
• Unsubscribe in every email. No exceptions.
• Promise nothing free. No automatic "free business spotlight" offers.
• Make the ask small. Invite the owner to check out the newsletter, maybe subscribe, and be open to a conversation about promoting their brand.

The tools are cheaper than I expected. Instantly quoted me about $500 a month in a demo, probably because we talked about thousands of emails a month. The simple stack a podcast guest uses is Outscraper for local business data and Smartlead to send. John Apolinar pays about $49 a month for Smartlead, about $15 a year per domain (he bought three) and about $4 a month per mailbox. Clay is unnecessarily complex for local.

Data is the hardest part of cold email, so get the list first. Use a dedicated cold email tool, not your CRM. Once it's running, it's about 10 minutes of checking a day.

What does good manual outreach look like?

Benchmarks from people I talk to:

• One operator books about one meeting per ten cold dials, by telling businesses there's only one spot per category.
• A peer's manual push was about 20 calls in a week, which booked three meetings. Two didn't show.
• Billy Howell of Arlington Bagel told me on my podcast he looked at the most-clicked links in his last four sends, called those businesses with the click count and a mock-up ad, and got one yes out of four calls. He suggests about 10 calls a day.

That's normal. Outbound is a numbers game with lots of no-shows.

Instagram DMs work too, carefully. I DMed eight of twelve local custom home builders and stopped on purpose so Instagram wouldn't flag the account. Even though you could do 50 in 30 minutes, don't. Go one business type at a time, and start small.

Should I hire someone to do cold outreach for me?

Not before you've done it yourself. I paid a cold-calling contractor about $16,000 for my insurance newsletter before ever doing the process myself, and got zero results. Do the hard work first. It makes you a better manager later. More in whether to hire a salesperson first.