Selling Newsletter Ads with Cold Email Outreach

I’m speaking today at Beehiiv’s Local Newsletter Summit.

Today’s article is a longer form exposition of the same content I’m discussing at the talk: a guide on selling your first local newsletter ad with cold email outreach.

The Local Newsletter Ad Sales Problem

Most local newsletter owners want to monetize primarily through ads. Many owners speed run to 5,000 subscribers (throw enough money at Facebook ads and you’ll reach that milestone), but when they switch gears from growth to monetization, they don’t see many inbound ad leads rolling in – not even enough to recoup their investment.

I see many local newsletter owners reach this point, and then give up on their newsletter - selling it off for pennies per subscriber.

How do you avoid this?

The Ad Sales Solution

If you’re not getting enough inbound leads, you need to do outbound. If you’re doing outbound and not selling ads, there are four potential problems:

1. Your outreach to potential advertisers is weak
2. You’re not reaching out to enough people
3. You’re not reaching out to the right people
4. Your “offer” is weak (i.e., your newsletter is low quality or not significant enough to warrant an ad)

In this article, we’ll focus on the first three problems.

Scope of This Article

In this article, I’m focusing just on cold email outreach.

It’s not the only way to sell ads or monetize your newsletter, but cold email has some distinct advantages.

Doing 100s of cold calls is a nightmare for the introverted personality type attracted to online businesses like local newsletters, but anyone can send cold emails.

Cold email will work best when mixed with in person networking. Walking into a business and introducing yourself, going to chamber of commerce meetings, just showing up to events and being known - they all matter, and your emails will hit harder when they’re warm.

Two additional notes:

• The same principles can be applied to LinkedIn outreach as well.
• I won’t be discussing issues at scale (sending 1000s of emails). There are distinct challenges to scaling cold email, which I’ll discuss in a future article.

When Should You Start Selling Ads?

I’ve seen some local newsletter owners think about trying to sell ads at 20 subscribers - I don’t recommend this.

Five thousand - and even more so - ten thousand subscribers have some psychological effect on potential advertisers which makes the publication seem more legitimate relative to lower subscriber counts.

However, I don’t think you have to wait that long. I would recommend getting to 500-1000 subscribers. Between organic growth sources such as Facebook groups, Reddit, and your mom’s groupchat, and a $10/day Facebook ad spend, it shouldn’t take you more than 1-2 months to get to 1000 subscribers.

If someone says no now, they may say yes later when you have more subscribers. The key is to start the outreach process early.

Is Your Outreach Weak? The Data Dilemma

Initial Hypothesis

In an earlier article, I discussed a strategy for selling ads which works as follows:

• Offer free ads to local businesses.
• Track leads delivered to those businesses, rather than simply tracking clicks.
• In addition to tracking leads, develop a system to track conversions, or follow up with the business to track conversions.
• Use the data collected on leads and conversions to negotiate a price for ads with the businesses to whom you offered free ads.
• Use the data collected on leads and conversions as evidence in cold outreach to new advertisers.

The underlying hypothesis of this strategy is that local newsletters’ ad outreach fails because they don’t have enough evidence to show prospective advertisers the value of their newsletter, and by collecting that evidence, they can increase the likelihood of selling ads to prospects.

Case Study: JLM Scoop

I implemented this strategy for the JLM Scoop, a bilingual newsletter in Jerusalem run by Alec Kremins, who works on partnerships at Beehiiv.

Our approach was to create a dedicated partners page that showcased the value JLM Scoop could provide to potential advertisers. The website included clear information about audience demographics, engagement metrics, and testimonials from previous advertisers.

It worked well - we collected good information on leads and conversions, have been able to use some of this success as social proof in cold outreach, and a few of the businesses to whom we offered free ads may convert to paid advertisers.

This hero section from Tamar’s restaurant promotion demonstrates how we structured the partnerships to deliver measurable results. We created specific landing pages for each partner, allowing us to track clicks, form submissions, and ultimately, conversions.

However, I believe this strategy is actually unnecessary.

Reality Check: How Local Businesses Make Decisions

Local business owners are experts in their field, but they’re not data scientists working at tech companies. Calculating the ROI on advertising is a HARD problem. Even when you think it’s easy, it’s actually HARD.

Example 1: ROI on Facebook Ads for Newsletter Subscribers

Many of you may think that Facebook ads are an easy context in which to calculate ROI.

Facebook even tells you directly how much you’re paying per lead, which in this case is your subscriber.

But - you don’t actually care about subscribers. If you’re running a business, which is in great part how you should see your newsletter, you care about how those subscribers convert to the bottom line.

• How does a marginal subscriber convert to additional ad revenue?
• To other types of revenue?
• How does the subscriber’s LTV vary between a more expensive Facebook ad and a cheaper Facebook ad?

No solo owner thinks through this fully, and they shouldn’t.

Example 2: Economists Can’t Calculate ROI Either

Even professional economists struggle with this problem. A paper by Justin Rao and Randall Lewis in the Quarterly Journal of Economics (2015) explains how difficult it is to measure the ROI of digital advertising.

This academic research shows that even with sophisticated statistical methods and massive datasets, measuring the true impact of digital advertising is incredibly difficult. The paper documents how even large-scale experiments struggle to detect statistically significant effects from display advertising.

The “Vibe” Factor in Decision Making

Since making data-driven decisions on ad spend is so difficult, to a great extent, local business owners are going to be making their marketing decisions based on a “vibe”:

• It seems like Facebook ads aren’t working great right now.
• Seems like they’ve got a decent number of subscribers, I think a lot of their readers will be interested.
• I really like the guy/gal running the newsletter, I trust them, going to stick with them.

Many local businesses make advertising decisions based on:

• Gut feelings about what’s working
• Trust in the newsletter and its owner
• Perception of audience fit with their business
• Relationships with media partners

Now, it’s important to note:

• Not all businesses will be “vibesy”, many will be more data driven (for better or worse).
• Being vibesy is not stupid, in many contexts you have to make decisions and your gut/intuition is the best tool you have.

Key Takeaway: Rather than trying to collect data on leads and conversions - which will perhaps only psychologically affect a minority of potential advertisers - just shoot your shot and ask them to buy an ad.

The Real Problem: Not Enough Outreach

Even if collecting data was super important, you should be able to sell ads with less effective data-less outreach.

You’d just have to send more emails.

After talking to a dozen local newsletter owners, something I’ve found uniformly is that they’re not sending enough cold emails to potential advertisers.

It’s one thing if ads are a small part of your monetization strategy, or you’ve already got enough inbound leads to make you happy.

But what I’ve found with most local newsletters is that they want to monetize their newsletter through ads, and maybe they want to expand past a weekly newsletter, but it’s not justifiable given they can’t make enough revenue.

But when I ask them if they’ve reached out to potential advertisers, I hear crickets.

Everyone reading this article should be able to make a list of 200 local businesses they can cold email.

Why Cold Email?

You don’t have to just cold email. You can also cold call, or even better, just walk in the door and introduce yourself.

But the nice thing about cold email is that it scales.

You can do 200 cold calls, but for the personality type that’s attracted to Internet businesses like local newsletters, it’s likely to be psychologically exhausting.

Cold email has several advantages:

• Scalable approach
• Less psychologically taxing
• Easily tracked and optimized
• Lower barrier to entry

In-person connections are an important part of sales, but email lets you cover more ground.

Finding the Right Prospects

In my first article on the Naptown Scoop, I noticed that most of the Naptown Scoop’s ad revenue came from a few businesses which had one of two characteristics:

This image shows some of the key sponsors for the Naptown Scoop newsletter. Notice how they include both well-established local businesses and national brands with a local presence in Indianapolis. This mix gives the newsletter credibility while addressing local market needs.

Looking at more examples, we can see that successful local newsletters tend to attract advertisers who either have a high customer lifetime value (like real estate agents and financial advisors) or businesses that benefit from regular repeated exposure (like local events and entertainment venues).

The third example further reinforces this pattern. These advertisers include service-based businesses that benefit from reaching an engaged local audience. The common thread is that all these businesses have a clear reason to appear in front of local residents repeatedly.

You don’t have to just focus just on those businesses, and in fact, I recommend you don’t.

Building Your Prospect List

1. Create a list of service business categories
2. Search each category in Google Maps for your area
3. Add every business to a spreadsheet
4. Identify the decision maker (usually the owner)
5. Find their email address and LinkedIn profile

Goal: 200+ businesses in your outreach database

Sample Business Categories

Make a list of categories of service businesses. Here’s 15 categories with which you can get started:

• Plumbers
• Electricians
• Carpenters
• HVAC Contractors
• Landscaping Services
• Home Cleaning Services
• Auto Repair Shops
• Roofing Contractors
• Interior Designers
• Personal Trainers/Fitness Studios
• Real Estate Agents
• Financial Advisors
• Dental Practices
• Home Inspection Services
• Moving Companies
• Insurance Agents

For each of those categories, search in your local area in Google Maps. Put every entry into a spreadsheet.

For each spreadsheet entry, figure out who the main decision maker is at that business over marketing spend. In most cases, it will be the owner. However, there may be some larger businesses.

Find that person’s email address and LinkedIn. Add it to your spreadsheet.

Crafting Effective Cold Emails

Basic Cold Email Structure

Remember: The goal is to start a conversation, not sell an ad immediately.

Next, for each person, you’ll write an email like this:

What Makes This Work

• Short and to the point
• Easy to read (takes seconds)
• Clear call to action
• Low commitment ask
• No media kit in first email
• No presumptive meeting requests

The goal of the email is not to sell an ad. It’s to get a bite - to start a conversation.

You should have a media kit, but you shouldn’t send it in your first email. You want to send an email that’s easy to read and easy to respond to.

How to disqualify yourself:

• Write an essay in your email.
• Be presumptive about setting up a meeting/call before there’s interest.

Advanced: Social Proof Approach

If you’ve collected some sort of data on leads and conversions, even though I’m suggesting that’s not needed, you should absolutely use that in a campaign. Here’s how I’d suggest you use that data in an email:

Advanced: Relational Approach

Take people to whom you’ve already sold ads, or even people to whom you’ve offered free ads, and ask them who else they know might be interested in advertising with you.

Then, send those people a cold email like this:

Advanced: Survey-Based Approach

• Run a survey with your readers related to a specific industry
• Use Beehiiv’s polling feature to collect responses
• Target businesses in that industry with the results

Example poll: “Do you have a home security service?” Three poll options:

• Yes
• No, but I want to look into it
• No

Best if the poll is contextual (e.g., after reporting on crime/law & order topic).

Then, send the following email:

Your Ad Sales Action Plan

1. Build to at least 1,000 subscribers
2. Create your prospect spreadsheet (200+ businesses)
3. Find decision makers at each business
4. Start sending personalized cold emails
5. Follow up with interested prospects
6. Track your results and improve

The key isn’t perfect data or the most sophisticated strategy - it’s showing up and making the ask.

Final Thoughts

When in doubt, remember…