How I book over $1k per month in newsletter ads.

I sold my first newsletter ad for $25 in September 2021.

8 months later, I’ve booked over $1,400 in ad revenue — in May alone.

My humble newsletter of 1,600 subscribers and 70 editions has earned over $2,500 YTD — including the $1,400 in May — with another ~$650 booked for June. Plus a few spots to fill.

I started this newsletter with zero intentions of monetizing it, so the added revenue is icing on the cake.

I’ve learned a lot — and I have a lot more to learn — about this whole newsletter advertising thing. But I’m going to share what I have learned so far, and how I’ve succeeded in monetizing my newsletter with ads and sponsorships.

Article Summary [tl;dr]

While I’m not going to disclose specific ad rates or intimate details about my advertisers, I WILL cover…

1. how I set my newsletter ad rates
2. how I’ve managed to get (quite a few) inbound ad requests
3. how I’ve sent outbound pitches — and landed several
4. and how I’ve managed the back-end of ad scheduling, inventory, and advertiser communication

A Quick Warning

There’s no “hack” here.

I wish there was. A straight-forward cookie cutter template, strategy, or framework to share would be awesome, right?

But my path to monetization wasn’t linear. Or formulaic.

Instead it's been a culmination of 2 years of building relationships, publishing tweets, threads, atomic essays, and newsletters, while trying to provide as much value as possible for my “audience”.

With the warning out of the way — let’s get into it!

Setting My Ad Rates

Before you get an advertiser, it helps to know what you’re going to charge for a newsletter ad. I had no idea what I was going to charge.

When I first set up my Swapstack account with ~650 newsletter subscribers, I had one ad slot to sell. I closed my eyes, threw a dart at the ad rate dartboard, and landed on $25.

That’s obviously a metaphor since I don’t own an ad rate dartboard (yet). But that is what picking a price for my first ad felt like.

After the initial ad, interest in advertising with my newsletter began to increase.

Demand went up. So did my rates.

And since the first single $25 ad spot 8 months ago, I now have three ad spots in my newsletter, all priced accordingly:

• Premium Ad (Top of Newsletter) — $125
• Standard Ad (Middle of Newsletter) — $89
• Footer Ad (End of Newsletter) — $39

So all three ad spots bring in a total of $253 in gross revenue per weekly edition.

Do all ad spots get filled every week? Nope, and that’s okay.

Here’s an interesting stat: the Premium Ad is my most popular spot despite it’s price — AND it’s been filled every week since March 8th, 2022. 13 straight weeks. And booked for 4 out of the next 5 editions, too.

“But how should I price my newsletter ads?”

Try my strategy:

1. set a low* price to acquire your first advertiser
2. increase your pricing as demand increases

*But don’t price your ad lower than $20 — you’re worth that much, if not more.

Publishers often find the first ad can open up the flood gates. So focus on getting your first ad. Then worry about your rates as you go.

Now, about getting that first advertiser…

Getting advertisers to come to YOU (Inbound)

Imagine someone approaching YOU to advertise with you. Sounds amazing, right? No pitching, no awkwardness, no delayed responses.

Well, it can happen. These are the joys of inbound ad request.

I’ve received a handful of inbound ad requests. Here are a few ways they’ve come to me.

Existing Relationships

One of my first big ad sales was from a brand that purchased a bundle of ads (14 spots!) at once.

But it wasn’t a cold inbound request.

I had built a relationship with this advertiser. We had DM’d on Twitter, chatted on Zoom, and sent emails back and forth. I had no ulterior motives to do those things, either. I was intentionally connecting with people who I found interesting and thought I could help out. In the end, we were able to help each other out.

Talking & writing about it

I published an article on Medium about how I got my first advertiser. I shared the piece on Twitter as a thread. Later that day, I had an inbound request to advertise in my DMs. Of course, a thread won’t guarantee landing an advertiser, but it will increase your surface are of luck. Every tweet is a free lottery ticket, as Packy McCormick has written.

Ad Marketplaces

My newsletter’s very first paid ad was an inbound request on Swapstack. I’m going to talk more about ad marketplaces later, but for now, just know that this is one of the “low hanging fruit” strategies when it comes to getting inbound requests.

Ads Beget Ads

I alluded to this earlier, but it’s worth repeating: getting your first ad can open the floodgates.

Once someone sees an ad in your newsletter, it clicks:

“I could get my brand in front of their audience, too.”

That’s why your main focus for your first advertiser shouldn’t be about revenue — it should 100% be about finding an advertiser, ideally one that’s relevant to your readers’ interests.

Now we can’t all be Josh Spector and have all our ad spots filled by inbound requests. That’s where outbound pitches come in.

Pitching brands (Outbound)

Inbound requests are the ideal. Outbound pitches are kind of the opposite: they’re tedious, intimidating, uncomfortable.

But they don’t have to be. Here’s my strategy for outbound.

How To Build Rapport & Reciprocity

Remember, sales should be a long game. I rarely pitch brands (outside of marketplaces) I haven’t interacted with or engaged with in some form. I feel more comfortable pitching when I’ve built up some rapport and created a reciprocal relationship.

The more you can engage and create some rapport with brands before pitching them, the better. And a little reciprocity doesn’t hurt either.

Here’s how you could go about it:

1. Do a free feature in your newsletter on a brand you’d love to have advertise with you.
2. Follow the brand’s account and engage.
3. Give them some love on social media promoting their feature in your newsletter.
4. Get to know the marketers or solopreneurs behind the brand as well. They could be your ticket in. For example, if you find their marketing manager tweeting about them, you might be in business.
5. Once you’ve established some back-and-forth, send a soft pitch about ad space and how you’d love to feature them more prominently. If the free feature received a few click-throughs, tell them (but be honest!)

I’m not going to pretend to know how to write a successful pitch. I’m still working on that.

I simply send an email or Twitter DM letting them know about the ad opportunities in my newsletter, and I share some relevant stats a marketer/advertiser would want.

Be you. Be informative. Don’t be pushy.

“My newsletter’s still pretty small… What if nobody wants to pay to advertise?”

Your newsletter may have too small of an audience to get the attention of advertisers.

If you’re stuck finding an advertiser, do this:

1. Reach out to a modest-sized brand, newsletter, or SaaS product that would be a good fit for your newsletter & audience.
2. Ask them if they’d be willing to “sponsor” your newsletter in exchange for an affiliate commission on any sales or sign-ups.

This'll reduce their risk and helps you get a legitimate sponsor/advertiser in your newsletter.

Using ad marketplaces [Inbound & Outbound]

I’ve mentioned Swapstack because it has been my #1 inbound request marketplace.

I’ve also used Paved for inbound requests. But unlike Swapstack, Paved doesn’t allow publishers the ability to reach out to brands. They have to come to you.

And so Paved ≠ outbound pitching.

Hecto and SponsorGap are other ad marketplaces you could try. I haven’t used either marketplace yet (I’ll talk about Hecto in the next section about how I manage ad inventory).

SponsorGap is a pay-to-play marketplace. Try it for $29 for a month. Or you can pay $99 for a full year. You could recoup that cost with one or two ads alone. You’ll have to assess if the math works in your favor or not.

I should note that a lot of the brands in the SponsorGap marketplace are looking for larger audiences, in the 10K+ range, from the limited research I’ve done. But there are a few who’ll advertise with the “smaller” newsletters.

Managing Ad Inventory, Organization & Reporting

So far we’ve set our ad rates, primed the inbound request engine, and started working on our outbound efforts.

These are the core first steps to monetizing your newsletter with ads & sponsors.

Soon enough, you’ll find you have some new responsibilities, like…

• Managing ad inventory
• Organizing the ad creative
• Reporting on the ad performance

And these are exciting new responsibilities, right?!

Here’s how I do it.

Managing Ad Inventory

If you’re just using one ad marketplace — managing inventory is easy. Skip to the next section.

If you’re using more than one — or plan to — continue reading.

Using multiple ad marketplaces — plus getting inbound requests and making sales pitches — means you’ll need a centralized space to manage your ad inventory. And then update your inventory in the various marketplaces.

I wish I could tell you I’ve found a customized solution for this. I haven’t.

So to stay on top of my ad bookings and inventory, I use a basic Airtable spreadsheet. An Excel spreadsheet or Google Sheet would work just as well.

You can even use a pen and paper, if that’s your thing.

But you will need something to manage your ad inventory — or risk the dreaded double-booking.

Tedious? Yes. But 100% necessary.

I also use Hecto to manage (some of) my newsletter ad inventory and handle non-marketplace ad payments. You can use it as a third-party ecommerce platform for your newsletter ads — but keep in mind that you pay them 5% for each transaction, plus Stripe processing fees.

Or you can do what Josh Spector does and just manage it all in-house.

Organizing Ad Creative

A booked ad is a great feeling! But not getting the right ad creative, or getting it late is deflating and stressful.

How To Get the Right Creative — the First Time!

Save yourself and the advertiser each a headache and get ALL the ad creative at once.

List out all the ad requirements — including character/word count limits, and image sizes — in your ad booking email confirmation.

This is so helpful as an advertiser: you have a simple checklist of everything the newsletter needs to publish your ad.

Things to include in your checklist are:

• Heading
• Subheading (if applicable)
• Body copy, incl. character or word count if applicable)
• Image & size (if applicable)
• Call-To-Action (CTA)
• URL link, including UTM parameters (you may not know what those are, but they’re important for the advertiser’s analytics tracking)

How To Get the Ad Creative — On Time!

The easiest way to organize your ad creative is to set an ad creative deadline. A good rule of thumb is a week before the ad is scheduled. This one-week acts as a buffer which allows ample time for you to…

• “massage” the advertiser’s copy & CTA
• work the ad into your newsletter
• send the advertiser the ad proof and get their approval (if needed)
• make any necessary revisions

So let your advertiser know your expectations as soon as you close the ad placement deal. Send them your checklist and deadline and you won’t regret it.

Because…

The last thing you want to do is deal with ad copy that comes in at the 11th hour. I have both experienced this AND been the advertiser sending in creative the day the ad is being published (sorry…!)

Ad Reporting

Sending an ad campaign report is something I regret NOT doing sooner.

I failed to send ad campaign reports to my advertisers. They didn’t ask — I didn’t send.

Now I send an ad report at the 6-day post-send mark.

I’ve chosen that time since my weekly edition gets an additional “resend to unopens” 5 days after the first send.

Bonus tip: the “resend to unopens” increases overall campaign open rate and often gets the advertiser a few more clicks. (It also nudges your cold subscribers to unsubscribe already!)

“But if advertisers don’t ask for an ad report, why send one?”

Here are 3 reasons why:

1. Your advertisers will appreciate the extra insights
2. You will be able to collect data points
3. You can open the conversation to running another ad campaign
4. (Bonus!) And politely ask for a testimonial, if the campaign was a success with conversion on their end

Poor-performing campaign? Send it anyway.

Some campaigns just don’t perform well — for a number of reasons:

• poor alignment with the brand and your readers
• ad copy and/or CTA was weak
• click-thrus generated zero conversions on their end

When it happens, the temptation is to not send the campaign report. Especially if the advertiser isn’t asking for it, right?

Well, I’m here to advise you should send it anyway. Why?

→ Maybe the ad only got a few clicks — but maybe one converted into a huge sale! You won’t know if you don’t ask.

→ Or maybe the ad got a bunch of clicks, but nobody converted once they hit the advertiser’s landing page. That’s a clear sign that the offer wasn’t clear or compelling enough to convert. The advertiser will need to work on their landing page in that case. Without your report, they might not have come to that conclusion.

You’re helping the advertiser figure out what went wrong.

Newsletter Ad Metrics I report on (with made up data from a $125 ad):

• Total Email Opens: 820 (50% total open rate)
• Total Ad Clicks: 20
• Total Email Clicks: 400
• Opens to Ad Click: 2.4% (20 / 820)
• Ad clicks to total clicks: 5% (20 / 400)
• Cost Per Click: $6.25 ($125 / 20)

You can use whatever data you find most relevant, but this has been more than enough data to send my advertisers.

In The End…

You need to remember the long game of all this.

I set out to publish 100 weekly newsletter editions before “giving up”. I never had monetization in mind in the beginning.

My mindset wasn’t short term. And that’s helped me stay patient with growth and results.

A few months back I wrote about how you could start with monetization in mind, and the ways in which to do it. You can read about that here: How To Reverse Engineer Content Monetization.

I hope this was helpful for you. Would love to hear about your journey with newsletter monetization.

You can check out my weekly newsletter and everything I share about starting, growing, and monetizing newsletters.

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