Webinar: Make 2026 Your Best Ad Sales Year Yet

Hey, everybody.

Welcome today to make 2026 your best ad sales year yet.

Ian and Nate from AD Astra are here.

We're excited that you guys are joining us.

Thanks so much for making time on a Monday.

We know it's the holidays.

We know there's a thousand things going on.

You're all trying to get to the end of the year and survive and get all that good stuff out into the world, but amazingly, it's already time to start planning around 2026.

So today we want to talk about ad strategy.

I think it's a huge, huge opportunity for so many of us in the newsletter space.

So thanks so much for joining us and share my screen.

We're going to try today to share a bunch of resources to help you figure out how to improve your ads in the new year.

Want to start though?

About 175 of you registered for this thing.

And as part of it, we asked, what's the current state of your ad strategy?

Good news is the majority of you said you are already having some success in the ad space.

You're selling some ads in your newsletter, but maybe there's some room to grow.

A little more than a third of you said, hey, there's an opportunity here to maybe build out an ad strategy.

We're still at the early stages.

7% of you are absolutely crushing it and should probably be leading this webinar instead of us.

But we're happy you're here.

Anyway, our goal today give you some of the tools, the tactics, the strategies to help you take things to the next level in the new year.

about us briefly, many of you and most of you came via, the Inbox Collective newsletter website.

You probably know me already.

Hi, I'm Dan.

Used to run newsletters at BuzzFeed and the New Yorker.

And now I run Inbox Collective, helping all sorts of teams with newsletter strategy.

Big teams, small teams, teams with amazing ad strategies like 1440 teams with emerging ad strategies like Boulder Reporting Lab.

in fact, I think we have someone at BRL on the call today.

So thanks for joining us.

Ian and Nate are also here.

They are wonderful guys.

They used to run ad ops for the Water Coolest, which sold to barstool back in 2021.

They launched ad Astra shortly after and have sold literally millions of dollars in ads and are true pros at this.

So I'm so happy they're here because they've worked with some of the biggest names in the newsletter space.

Places like 6am like nice news like Morning Brew, and have so much knowledge to share.

I'm going to bring them on in a second and they're going to talk through some of the strategies that they're seeing.

But I want to dive in first by just talking you through the outline for today.

What's going on, what we're going to discuss thing number one.

We want to talk through the building blocks of a good ad strategy.

What are we seeing teams have success with?

What do you need to implement next year?

Two, we're going to talk about securing the deal.

That's where Nate and Ian have tons to share because they have done this over and over and over again, helping teams figure out, hey, you have a lead.

Someone who's interested in your newsletter.

Here's how to actually get them to sign on the dotted line and pay you to be an advertiser.

And lastly, setting your deal up for success.

This is something that, as we've been talking over the past few months, has really stood out to me as a huge opportunity.

It's not just about closing the deal, but figuring out how do you set up the right types of ads, the right process for renewals, everything to make sure that you don't just get a subscript, get a new, newsletter advertiser.

but you get someone to stick around for a long time.

We'll also share a few final lessons for selling ads and we're gonna have plenty of time for Q and A.

this is everyone's 10 millionth Zoom webinar, I am sure, so you'll be familiar with that little Q and A box at the bottom of the screen.

As you have questions throughout the webinar, drop your questions in there.

We're gonna do our best to answer as many as we can today.

Also, we're gonna tell you a little bit more later.

But this is a fun thing that we have not officially announced.

We are sharing it with the universe.

All of you, for the first time right now.

We've been working on for the past couple of months this newsletter advertising playbook.

We think it is the most comprehensive guide to ads, selling ads and newsletters that has been built ever.

There's all sorts of amazing resources and bonuses.

We'll tell you a little bit more about it later and how we think it can help you.

But let's start right now by talking through some of the building blocks for a good ad strategy.

And Ian, actually, I'm going to take this, take this one thing, then, Ian, I'll kick over to you.

Understanding your newsletter, your audience and your positioning is such a big thing.

So often we see teams that say they have a great list size, open rates are good, but they're not selling what's wrong.

So, Ian, can you tell us a little bit about how you're advising clients to figure out.

All right.

What makes my newsletter special and how can I explain it to an advertiser?

Sure, yeah.

Thanks everyone for joining.

as, as Dan just mentioned, I think that you know, the first step of selling your, well selling advertising in your Newsletter is understanding who your newsletter really is.

If you know, you're focused on reaching businesses that you're writing about.

If it's, you know, a niche AI topic, if you're a local newsletter, you've got to understand who your audience is and who your advertiser should be.

So it's going to be different for, for each newsletter as you go out there.

But it's really important to understand who your audience is and use some you know, surveys and kind of ask questions to know literally who is in there and some of the things you want to focus on.

It's you know, your audience, their age, their income, their sex, their you know, other areas of interest, job title.

Depending on, you know, depending on what your newsletter is.

If you have a health and wellness focused newsletter, then you're going to be kind of gearing your advertising more towards general products and those kind of, you know, those kind of advertisements.

But if you're, you know, a niche AI newsletter or a finance focused newsletter, you're going to be looking for products that are related to the topic that you're writing about.

And similarly if you're a local newsletter, then, then you're going to be, you know, then your focus is more geographical.

So you're going to be looking for businesses that are in your area that are going to want to reach the people that that, that you have in your audience.

And so that's really, you know, like that, that's what, when we say what makes your audience unique, it's identifying which one of those focuses do you have and then from there getting more specific data about your audience.

And that's what you're going to sell to advertisers.

and a few ways that you can get this information.

one is when you sign, when people subscribe to your newsletter, your welcome flow, you know, you should send them questions that are giving the basic, you know, getting, capturing the basic information that you need, to identify them.

and again income is a big one.

Their job focus.

This, you know, this is an example of a, of a, of a different newsletter that, that was more of a B2B, specifically focused on franchising and financing, lending, that type of stuff.

So you know, you, you, you'll have to decide what is most important for you and your newsletter.

but sending questions out when people subscribe is one way you can put questions in your newsletter like you know, a poll option or something.

Make space in the newsletter and so you can Send it out and collect the information over time or separately.

You can send just a survey, you know, outside of your newsletter.

Send people a survey and just say, hey, you know, please, please complete this survey to help me identify who, you know, the, the people in my newsletter.

It would really help me if you answered these questions so that we can continue bringing you this newsletter for free.

Because, you know, readers understand that if you're not charging them a subscription fee, then, you know, you've got to keep the lights on somehow and you're going to be putting ads in the newsletter.

So, you know, one thing we've noticed is, you know, surveys is really the main way that all the, all newsletters are capturing this information.

And you don't need that many responses.

Honestly, just a couple hundred responses is enough, to be considered a good sample size.

so, you know, if you have 10, 10,000, 20,000 people in your newsletter and you only have a couple hundred responses, you know, that's fine.

If you have, say, 100,000 people in your newsletter and you still only have maybe a thousand responses or a couple hundred, you're still okay.

Because, you know, once the sample size gets to be that big, you know, you don't need to have 50% response rate to be considered, having enough information to represent the sample.

I'll jump into just to say, because we got this question from someone when they RSVP for the webinar.

Is there a way to collect this without doing surveys?

And the truth is, the best way you're going to collect this data is by directly asking your audience if you want to know something, like, what are they motivated by?

What do they care about?

What are they interested in?

Where do they work?

The best way to collect that data is to ask them directly.

Like Ian said, you can do it in your welcome series, you can do it in a welcome email.

You can do it in your regular ongoing newsletter.

There are tools like megahit is one that we recommended to folks that is good for B2B newsletters that can match up, the data that you have in your email list who subscribed with LinkedIn data to try to help you understand a little bit more about who's in the list.

But to understand things like motivation or like this example on screen, this is from the Wolf of Franchises newsletter.

To understand, like, which types of franchises are you interested in purchasing?

You're only going to be able to get that data, if you ask them directly.

So don't be afraid to ask Ian.

Keep going Tell us about some of the metrics that you are recommending to people because list size matters.

But lots of teams now have lists that are 20,000, 50,000, even 100,000 readers.

So what are you recommending to your clients that they emphasize in something like a media kit?

Well, yeah, so your, your list size definitely is a key information like the advertisers want to know.

Okay, what's, you know, what's the range of people that I'm going to, to reach here with, with your ad, or with your lists and you know, basically just kind of to calculate everything.

You have your list size and then you have your open rate.

So that will tell you actually how many impressions are going to be viewed, you know, how many impressions the advertiser is going to get.

There's been some, you know, different newsletters will present the information differently where the sends matter in that they've built up their brand to some extent where you know, if, if you're in, if they're in the inbox of people and you're sponsoring the ad that day that you know that counts or that's some exposure for you.

We're, you know, we're, we're definitely more strictly focused on open rate from our perspective.

Like you're really not getting an impression if somebody's not seeing the ad.

and then you know, once you're, once you have the open rate, then the advertisers are going to want to know, okay, how many people are clicking on ads and what's your click through rate.

on ads.

Some publishers like to include in the media kit and we'll get into, Dan's going to get into the media kit more.

But you know, kind of alluding what I just said about the list size and open rates, it's just best to be honest and just you know, don't fluff your numbers because it really doesn't benefit you in the long run.

publishers will put a click through rate of 6 to 7% in their media kit, but that's also for links that are not ad related.

So you know, if an Advertiser sees a 6, you know, 6 to 7% click through rate, they'll say, wow, that's great.

And then the performance will definitely not, not you know, reach that, that level.

So you know, I can just say also that a good ad CTR or kind of a, you know, a good spot to be is like a 0.5% to 1.5% on specific ad click through rates.

So that should be your goal as far as to target to try and, and have, have that be your, your ad click through rate for, for your newsletters.

But you know, these are the key things that you're going to need to know and these are going to be in your media kit along with some other things that we'll get into.

I'll mention too the difference between it's a really good call Click to Open rate versus Add Click to Open rate like with Inbox Collective, my click to open rate is north of 21% people.

One out every five people or so who open the newsletter click on a link in the newsletter.

If I went to an advertiser and said gave them that number, they'd be like this is incredible.

One out of every five people is going to click on the links.

The ad click to Open rate is closer to 2%.

So still very good.

But the advertiser has to know what they're getting into upfront.

All right, so Nate, I want to bring in here we have some of the metrics that you're thinking about but packaging and pricing becomes a really big deal.

So tell us a little about some of the ads you should run then we can talk through how to price these.

Yeah, so I think a few things.

So it's important to have native ads I think are the most important type of newsletter ad that we'll call a traditional newsletter sponsorship.

So in the newsletter world there's lots of different types of advertisements that you can sell.

but the ones that you want to avoid the most are like kind of what you see as a heading banner sponsorship that isn't, it's just kind of there as like what you would see on a pop up on a website or something like that.

So those can get lumped into like the newsletter space as a newsletter ad.

But those are the what I would say the worst types of newsletter sponsorship.

So those native ads are what you're looking for because you want everything written in the tone of voice of your newsletter and for it to be integrated within the newsletter as as much as possible to look like it's content versus an advertisement.

So you can see that through native ads, through secondary ads, through sponsored sections and through dedicated emails.

but those are all, those are all different types of native sponsorships versus the banner ad.

And you could see this is a decent, a good example here from 1440, this newsletter in partnership with this organization, you know, and then you get a really nicely written, very friendly kind of ad below.

It doesn't feel super polished it doesn't feel super slick.

It feels like the team is saying, you know, we're making this endorsement, here's what we like about it.

Telling you about them.

It feels really friendly and nice.

Yeah.

And the, the content in the way that it's structured too is the same exact structure as the rest of the section of other, of other writing blocks that 1440 does.

So I think the more, the more that you can do that as a newsletter, the better performance you're going to see across the board.

Tell us a little about pricing.

How do you get, how do you advise clients to price these ads correctly?

Yeah, so pricing can be very complicated for, for a lot of teams and there's, there's really no one size fits all answer.

Because pricing is going to be so specific to your newsletter, with kind of through what Ian mentioned.

But it's also very specific in, with performance as well.

So CPM is a great place to start as a, as a baseline benchmark for how you're going to how you're going to structure your pricing.

cpm you can see on the slide how it's calculated.

It's basically your list size times your open rate to get, you know, your, the, the people opening.

You divide it by a thousand, multiply by your quote unquote cpm.

you don't have to remember that though because you can just quickly Google CPM calculator.

We do it all the time.

You don't have to lie if you don't because you know the, the formula and everything changes there.

But that's I think a CPM is a great way to, to get started in terms of how you're pricing it.

but it's not the end all be all.

So CPMs range a lot between the type of newsletter that you are.

So B2B or very specific niche career focus typically will get the highest CPMs.

We've seen, we've seen specific newsletters that have maybe 15,000 subscribers.

There was one that like their focus was, was on legal like bankruptcy or something like that.

And they were charging like a $600cpm or more because you know that if you get one legal client convert to like an attorney firm, you're going to, you know that that's worth so much to that advertiser versus selling electrolytes.

Right.

So it's a, it can, it can range a lot.

But yeah, so in the chart you can kind of see there, there's different ranges by the type of newsletter and it, and it kind of goes down, based, based on what you have, whether it's local media or independent creators hobby and then kind of larger publications that are not, that don't have a specific focus will get the least.

but I want to say that like CPM is a great place to start and how you're pricing, but it's not a one size fits all because a lot of advertisers in the newsletter space are going to be looking for performance.

And if you're stuck to your specific cpm, and won't change pricing based on performance, whether it's raising the rates or lowering the rates, you're, you're either going to be leaving a lot of money on the table or there's going to be a lot of unhappy sponsors that you're not going to be able to renew.

So it can kind of go in both directions.

And it's really important to also take into account how are sponsors performing, what kind of click through rate are we getting on the advertisements and generally just the pulse of how are our clients doing?

and a lot of times that's more important than sticking to a specific cpm.

Yeah.

And this is the case too.

The numbers we're sharing on the screen right now, it's a baseline for what we see in the industry.

It does not, as Nate said, does not mean this is the hard and fast.

You must stick to these rules.

If you're outside these boundaries, you're way off base.

It's a starting place.

So many teams that I work with, you know, I'll sit down and have a conversation with them about their strategy and they go, you know, we got 25,000 readers and our open rates are good and we're charging $112 an ad or whatever.

Like, sorry, how did you come to that number?

Well, because, you know, when I inherited the newsletter program here, that's what we used to charge.

So we never changed it.

It's like, well, I've got good news for you.

I've got good news and bad news.

The bad news is based on the industry averages I'm seeing, you should be charging this, you know, this to this.

the bad news is you've been leaving money on the table.

The good news is we can update our rates based on that, but it's a starting place.

Also, average amount to not be $112 and yeah, at a clean number.

Yes.

In terms of packaging.

So this is the other piece of it, so you can start coming up with your number.

All right, so you know, the Value like this example we had on the screen.

20,000 readers, 50% open rate.

Your CPM is $30.

You're in the local media space.

An ad should be worth about $300, maybe more, maybe less.

But an advertiser comes to you and says, well, I'm looking for a package.

I don't want just one ad, I want to do a couple with you because I'm going to get better results, better chance for success.

Then you start to talk about discounting.

So what do you advise teams to do in that case?

Yeah, so I think as, as a newsletter publisher, right, the goal is to sell as much of your inventory as possible from the jump without one over saturating that, that specific advertiser with your audience.

and two, you just want to be able to set something up that's going to be successful, where they're going to renew, and be happy.

So I think that the middle ground package that you kind of start with is going to be three ish placements.

and you can, you can set that as a 10 to 15% discount from whatever your listed market rate is, even if that listed market rate is higher than what you actually want to net from that.

So if that three placement package should really, even if it's quote unquote discounted, it really should be what, what do I want to make from three placements?

And that's really your true and true market rate.

but you want to list that single placement rate to kind of help back into that three placement package.

Because a lot of times advertisers, especially right now with a bit of a slower economy, advertisers are just going to want to test a single placement, see how it performs and then decide from there.

But we all know that one placement isn't a great benchmark for how a news, how an advertiser performs within a specific newsletter.

and a lot of times that can, you know, that can, that, that can be any, the impact of anything happening on a given day, whether it's external from the newsletter or something with their ESP or just whatever, whatever the circumstances of that may be.

One, placement doesn't fully give performance, but at the same time, if it's a new advertiser, you don't want to overbook them from the jump and have them feel constrained by a deal.

If the first placement or second placement doesn't really perform well, it's so important to have the extra placements.

Otherwise, like you said, you know, a single newsletter underperforms there was an issue that day with Gmail.

Something got marked as spam.

The advertiser goes, I thought you said the open rates should be this and the click rate should be this.

You lied to me.

But if you have multiple placements, if something does go wrong, you get multiple chances to prove that your newsletter can deliver for them.

Also with like B2B sponsors specifically, like you're, you're not going to convert that lead, like right on that day.

And it takes a lot more time to like build audience Trust with a B2B sponsor versus like electrolytes.

Right?

Like it's, it's too.

You still want to build trust as a, as a D2C brand.

And that's you know, it's very important.

But the lead time, the sales cycle is just a lot longer with those B2B sponsors.

So especially when you're talking, if you're a B2B publisher, like, you need to make sure that you're probably not really selling single placements unless you absolutely have to.

and then lastly, like kind of the five plus placement package, but really.

And you can discount that more to incentivize it depending on what your, your ad strategy and positioning is.

But I still think that's too many placements from the jump where like, if you can lock someone into like three to four placements on that intro package and they perform well, that's when you can start to have those discussions of, okay, let's see if we can book you out for the quarter or for half the year and kind of see what cadence makes the most sense based on how often you publish and how often you think that sponsor would be a good to have a good touch point with your newsletter.

I see this too, like with B2B newsletters.

The franchise example we shared earlier, Imagine your legal.

So a, law firm that specializes in helping people buy their first franchise.

You see one ad in a newsletter, you're probably unlikely to go and you know, become a client of theirs.

You might need to see them multiple times over a long window of time.

But the same thing can even be true in the, you know, other B2C kind of spaces.

Like, you know, in the local space.

A lot of the clients I work with who might work with someone like a real estate agency seeing one ad for a realtor, I'm probably not going to call them up and go, I've been looking to buy or sell my home.

You might need to see them multiple times over a longer window of time.

understanding that can also help Push you towards, hey, you know what, local realtor, you want to work with us?

I don't think one ad is going to do the trick.

I think we want to talk about a longer term deal.

Yeah.

And that's a great way that you can position when you're speaking with advertisers as well.

and just having them understand the value of that, the value of your audience and not like yeah, just, just making sure that they understand that it's a long term horizon here.

Not like a quick hitter.

We're gonna get the impact right away.

Let's talk briefly about price increases and then we'll jump over to media kits for a second.

How do.

This was a question that came up a few times before the webinar.

When do you increase prices and how often?

Price increases can be really tricky.

and you want to again like it's a one, it's not a one size fits all thing.

so it, what I say now take it with a grain of salt because there's so many nuances between any situation that you get to.

But generally speaking I think every quarter you can update your rates just based on the new updated metrics.

Unless you have some crazy spike that happens over, you know, in between then where you really need to.

But generally speaking if you update your rates every quarter, I think that's, it's a good general timeline or at least every two quarters.

unless you don't kind of, unless you don't need to.

But anything beyond that you're just going to get out pretty out of date data.

and how to handle price increases with sponsors, it can be a, it can be a, you gotta walk a tightrope.

So obviously as you know, if you have, you have a sponsor, they're in at a lower rate, your rates are increasing over top over time.

Like you're going to need to raise the rates with that sponsor now and they're going to understand that.

But you're probably not going to get that sponsor up to your new market rate right off the bat.

And what we've noticed over time is, you know, as long as you want to keep that client, keep them happy and keep them filling their inventory because they're integral to your, you know, your revenue and your strategy.

Like it's okay to take a little bit of a hiccup on the pricing and not have them at your rates and just steadily move them up but not at the same exact market rate, that you're maybe pitching other sponsors at.

and I think that it's.

That's really important to walk that tightrope.

And it'll really just depend on, you know, is this a good client?

Are they always asking us for discounts if they are?

Well, maybe, like, they're not as great of a client and it's, if they don't want to pay the market rate, it's okay.

Or someone you really value, you want to work out a deal that, you know, you can, you can go to them and just say, hey, our list size went up to X.

I know you're, you know, we want to keep you sponsoring in the newsletter.

Can we, you know, meet at X price point?

That's, you know, in between, so that you're still seeing the value.

But we're, you know, we're, you know, getting close to our market rate.

So that's a reasonable conversation to have.

And then the other reason why it's important to do it every quarter or so, is that your marketers, or budgets will change every quarter.

Usually.

sometimes they happen quicker, but that's usually a good benchmark for that.

Yeah.

So let's run quickly through this one.

Where do you place your ads and what does it look like in your media kit?

So I just want to say mention a couple of things here.

One, teams often have some sort of, you know, like we shared this example earlier for 1440.

Some sort of primary ad, presented by so and so.

Here's the main ad in your newsletter.

It's a nice native ad.

There might be a secondary ad as well in the newsletter.

It could also be a native spot for a different sponsor, but maybe a little bit shorter.

They don't get the big branding at the top.

And then you start to think about these tertiary ads.

This is all from a recent example, but this is last Friday's, Marketing Brew newsletter.

And you can see at the bottom, they do have a small sponsorship opportunity.

It's not a huge thing.

It's a line of text.

Looks more like a classified ad than some of the native ads we've been sharing.

But multiple ad slots within the newsletter allows them to maximize the revenue they get out of every newsletter sent.

In a way, running newsletter ads, a little like running a hotel.

You can't sell yesterday's, room space.

You only have the inventory you have ahead of you.

So you got to make sure.

All right, we have this newsletter.

We have different sections.

We've tried to build out a lot of original content in here because it allows us more space to place some of the newsletters.

So as you're thinking through that, we have the pricing, we have the survey and research, the, data that we got about our audience, we've kind of figured out, sort of figure out, all right, what makes our newsletter special.

And it is so important to think about, like, what makes your newsletter special.

There are, for instance, and you two have worked with a bunch of them, you know, a lot of AI newsletters this space.

So just saying, we have an AI newsletter is not enough.

What makes our AI newsletter unique, special, different.

Even now, in my little world, like the newsletter space, there's now a lot of newsletters about newsletters.

What makes mine different, what makes mine unique, unique.

And so it's so important to put together a media kit that talks through who your audience is, what makes them unique, and what the offerings are.

So as part of the ad playbook that, we've been putting together, one of the really cool things is that we created this media kit builder that allows anyone to create a media kit super quickly.

So you go through.

I'll kind of give you the really quick version of this.

A little bit about your newsletter, the description, the audience, you know, what describes my newsletter, basic information like, you know, ad click through, rate, you know, talk a little bit about what the placements are.

You collect some of this information, and then you pop it into this, this builder here, and you enter some of the information, and then at the end, after a couple minutes, you put in the information, it spits out a media kit.

So this is the one it created for me.

What's really fun is I'll show you this, you grab this, you make a copy of the whole thing, and then once you have this, you can edit it and add more to it.

So for Inbox Collective, for instance, I created this larger media kit, has my basic information around who my audience is, what makes them special.

It comes up with a couple different versions of presentations.

So, for instance, with my audience, gender isn't all that important.

Someone who's trying to sell newsletter software doesn't care if they're male or female.

They just want them to be buyers.

They want them to be right people.

So this version of the page might not work, but this version that says, all right, they work in media, nonprofits, independent media.

This is more my speed.

You can add to it.

You can adjust.

Comes up and creates some initial sorts of opportunities here based on the data that you put in.

And then you can edit and adjust even little things in here.

Like if you have a case Study, which I don't have, or testimonials, which I didn't include.

It'll add these in.

It'll spit out to multiple versions with different designs.

So you can do something that maybe is more your color scheme and then you can edit and adjust as necessary.

But the goal is, hey, I need to create something that looks nice without doing a ton of design work.

We've built this media kit builder to try to help you get that next version of your media kit out as soon as possible, as quickly as possible.

Over time.

You can edit, you can adjust, you can add to it.

It.

Let's talk about, securing the deal for a second.

Because this is a big thing.

We've gotten a lot of questions about this.

How do you identify the right sponsors?

And how do you start to go through this prospecting, process of saying, all right, I think these are the right people.

How do I get them to talk to me and then eventually become sponsors?

1.

Where the heck do you find people?

I always tell folks, try to identify people who are already spending money in your community.

And that could mean digital community.

Hey, I see these people advertising in similar newsletters or in podcasts relevant to my audience.

Great.

If you're covering a physical community, a local community region, that sort of thing, keep an eye out for who's advertising in your neighborhood as you.

I tell a lot of my local media clients, you know, when you're driving around town, have the radio on.

If you hear someone say, you know, sponsor a local segment on the radio.

Hey, they should be, someone who's on your list of people to reach out to.

You see someone advertising on a billboard, at a bus stop.

these are all people spending money in the community.

They should be on your list to reach out to.

There are some tools like sponsor flow or who sponsors stuff that track things like who's sponsoring other newsletters.

Those could be useful.

There's even tools like Megahit that can look through your email list and say, hey, here are the people who are already on your list.

They already read your newsletter and open it, click on it.

These could be potential sponsors as well.

So start by looking through your community.

Anyone you see advertising anywhere.

This is something Ian and Nate have taught me.

That's a great lesson.

Anyone you see advertising anywhere is a potential sponsor should go on your list.

You probably also want to create a page as well.

You know, that you link to in your newsletter on your site that lets people say, hey, I'm interested in sponsoring you.

I want to reach out Directly make it easy for them to contact you.

Love this example from Nice News Name email, little bit about your brand new.

When you want to advertise what your budget is, some basic information that we can collect and put you onto our list and reach out and say, hey, we'd love to talk a little bit more about how we can work with you.

All right.

Once we're through this process, you know, you figure out, all right, the types of brands, then you got to figure out who the right person is to contact.

And these the job titles that tend to be the ones that are the buyers of newsletter ads.

You're looking forward to growth, like marketing, like partnerships.

And sometimes you have to contact multiple people at a company a bunch of different times to get them to say, hey, I think we'd actually love to have a conversation, but you're looking through.

It's okay.

If you're reaching out to multiple people at a company, they can always say, hey, I'm not the right person, but my colleague so and so is the one that you guys should be looking at.

And then you want to have a spreadsheet to track all of this.

So, you know, for.

We created actually this part of the Playbook, too, this basic spreadsheet.

So you have your list of the people we've been contacting.

And as you go through the process, whether you buy the playbook or not, we always recommend something like this.

Hey, you know, these people are someone who I've identified as a potential, potential lead.

This is someone who I've emailed maybe once, twice, a third time.

This is someone who's an active lead.

They've reached back out to us and said, we want to talk.

And as you go through the process, you go, this person.

Hey, they reached out to us.

They responded to us.

They're an active lead.

It drops them into the next tab of the spreadsheet.

So you can keep track of.

All right, they're an active lead.

We've set up a call.

We're negotiating terms.

We're sending over the IO, which is the insertion order.

That's the contract.

Hey, they're ready to sign.

You can keep track of it as you go through the process and later on.

These are our current sponsors.

We've collected assets.

Here's the link to the Google Doc where we're keeping track of everything, whatever it is, but you want to have a place that you keep track of who you've reached out to, when, where you are in the process, so that over time, you know, hey, there's lots of people out there who, you know, are potential leads.

These are the ones who we're really talking to.

These people we're closing.

You can keep track of all of it as you go through the process.

It's just a lot to keep track of of you got to have a spreadsheet.

All right, so you go through all that process.

Neat.

What's next in terms of, you know, hey, I've identified some leads.

I'm trying to get someone to, you know, Nike to sponsor my newsletter.

Nike's trying to get into the newsletter game.

They want to spot.

They want to be the sponsor of more newsletter writers.

seems unlikely, but sure, maybe it could happen one day.

That's the dream.

so Hoka would actually be more my speed, to be honest.

But that's just because I'm an old man.

how.

What do I send these people and how often do you follow up?

Yeah, I think the most important thing with your emails is short, relevant and succinct.

Like how all of us get emails that we open.

Don't read the full email because you see one line and it's immediately not relevant.

So everything you like.

It's a pretty straightforward formula with how you're trying to, you know, how you structure your email.

You don't need to overthink it.

You don't need to be catchy.

You just have to be relevant.

So a lot of times, like, your subject can just be, you know, reach, reach, audience.

That's xyz.

that's relevant to who you're reaching out to.

And you can set up automated cadences that are, you know, for different industries.

You're reaching out to, the body of your email.

Right.

Saw your advertisement in X.

Love that you're using, newsletters to grow your business.

We have an audience of X, high value subscribers.

And why.

Let's chat.

that's going to be the most relevant way to reach people.

And more times than not, a very simple email cadence will get people to respond.

You don't have to overthink this.

I didn't tell you guys this, but I just remembered it right now.

Over the weekend, I got a pitch from somebody, but it was in the form of they sent me literally two cents on PayPal and their pitch was attached to it.

I deleted it immediately and blocked all of them on LinkedIn.

It was so scammy.

And if they had just sent me an email and made an honest pitch about why it would be valuable, I would have read it and considered it but because they tried to do something shady, I was like, no, no, the conversation is over here.

Exactly.

tell us a little about some of those.

So you reach out to folks, you get them on a call, you track them in your spreadsheet, talk us through the negotiation process, what happens next.

Yeah, so I think the most important part is to keep everything organized.

Like Dan had mentioned before, if you're not timely with how you're structuring your follow ups and how you're talking through, everything with the advertiser and it takes you, you know, 48 hours to get back to them, you're going to lose the deal right there.

but in order to negotiate, it's important to get a baseline understanding of what their goal is.

You know, everyone will want to talk about their own newsletter and how great it is and how great the audience is.

And you have to sell it to a degree.

But more times than not, you need to understand what their goal is first and then showcase how relevant you can be with your audience.

And sometimes it might not be relevant and that's okay.

You don't need.

Every sponsor isn't going to be a fit.

so that's really, I think that's a really important thing to understand is don't, don't try and force a fit that isn't there.

and I want to hop, in real quick because one thing I think that as we were just talking about this, that's important when, you know, going through the prospecting process, you can, you can see what advertisers are sponsoring multiple newsletters.

So when you're, when you're getting into negotiating, when you're getting into the prospecting side of things, you know, try to understand if they've done this before, if they're in a bunch of newsletters, then they're gonna, be able to have a conversation with you back and forth.

They know what they're looking for already if they're a new, you know, a new advertiser to newsletters, a, Nike or a Hoka or some kind of, you know, brand that's interesting.

you know, then it's a little bit more of a process.

You have to educate them a little bit more.

And I, I think we'll get into this later.

But I just wanted to just make a note of that now because as you're having these discussions and doing these negotiations, it's important to know or at least have an idea of where the advertiser is coming from so that you can either Give them more information that they don't have or continue to move things quicker.

Because if, if they already know, you know, like, if they already know the questions or the things that you're trying to tell them, then you don't need to waste your time.

you can just move forward and get, you know, get the deal done that much quicker.

Yeah.

Nate, in terms of discounts, so you mentioned earlier, we talked about having a package that could be one reason to discount.

Are there any other reasons that someone should discount?

Yeah, I think it, it really depends on that conversation with the sponsor.

I don't think you want to jump into the discounting off the bat because then you set the precedent that you're always going to be discounting.

And a lot, a lot of times in the newsletter space, we'll see advertisers that are just accustomed to, we're gonna get a 20 discount as a new sponsor.

Like, and that just doesn't set a good precedent for the space at all because not everyone discounts.

Right.

So you don't want that to be your starting point.

but like we said with the package, if you have your three placement package at what you really want, you can sell a discount that way.

So I think that's a great place to start.

But also, there are times where, you know, if you're low on inventory, people are going to be looking for, or you're sorry, you have a lot inventory available, like, you need to fill it in a short time period.

That could be a really good time to discount your rates off the bat.

But, with a new sponsor, I don't think it's a good precedent to set right off the bat.

and then in terms of payment, can be tricky.

Right.

Like, I'd say a good standard for the industry is N15 from the run date.

Sometimes N30 from the run date.

That's a little.

I wouldn't really go beyond n 30.

You mean net.

Just to explain it.

So net 30, which means we, we said we run the ad.

You need to pay us within the next 30 days.

The next 15 days, whatever it is.

Yes, exactly.

But, you know, some publishers will require prepayment and, and that's okay.

you might lose some business that way.

I think just being dynamic with pricing, with a net 15 standard is a good spot to be.

and then as you finalize the deal, right.

You have to know the timeline of when they're looking to run how many dates and try and scheduling them.

unless you're, you know, it Depends.

Scheduling, depends a lot on the type of newsletter you are, whether you're weekly, whether you're, you know, whatever it may be.

but you just want to make sure the advertisements are spread out enough, I would say, two to three weeks from one another to just make sure that you're not oversaturating.

Unless they specifically request, like, you know, running a blitz campaign in a specific time frame.

The last piece of this is setting the deal up for success.

And Ian, with the running towards the end here already, we got about 30 minutes left, so let's talk a little bit about communicating expectations and some of the best practices here.

Yeah, so the biggest thing that we've seen where it causes havoc in, you know, once you're get, you're, you're trying to get a deal done, and then the advertisers there, and then you get the deal and they say, okay, we're going to run this ad tomorrow.

Let me loop in my ops person.

And then crickets, you know, so, so you got to.

Again, and this is all part of, like, the conversations.

And as you, as you're having these conversations, you'll know what to ask for and look for along the way.

But making sure that, you know who's writing the copy.

Do they have the assets ready?

How quickly can they turn it around to make, you know, to make sure there's enough time to get the ad ready.

Have all the assets send them a test so that they can, you can make sure that the links are working and that everything's tracking proper, properly.

you know, that's, that's, that's the most important thing because if, you know, they sent the wrong links, we sent the ad out, but nothing's tracking.

Now they don't want to rebook, you know, or the copy.

It didn't get approved the right way and it still ran.

Now they don't want to rebook.

So it's really just making sure you have enough time for everybody to agree that you have an approval process in place, that there's a test process so that you can make sure all the links are working.

And then the results, you should report them.

7 days max.

After the ad runs, like we understand, people go back and, and click, you know, from a day or two before and, you know, seven days is really the right amount of time for your data to mature and be complete enough to send it to the publishers.

And when you send it over, you say, okay, here, you know, you can do it.

I guess if you, if you know, you're Running multi plate multiple placements.

When it comes to the first, you know, you're sending, you should be sending the data along as the placements are running.

but, and then at the end of the campaign, hey, you know, here's your total campaign results.

Would love to book another package with you.

you know, let us know how the results were on your end and we can go from there.

And by the way, a lot of some teams will make this mistake.

They'll send the results a day or two later if you send them too soon.

Especially for newsletters that, you know, B2B newsletters for instance, people may not be opening them right away.

There's not a timeliness aspect to it.

So give it a couple days because otherwise you might be under reporting the actual performance.

And you mentioned some of these, but you know, collecting the right assets, this happens so often.

Teams say, you know, I thought you were going to take care of all this stuff.

No, I thought you were going to take care of this.

No, no.

What do we need?

We need what's the image?

What's the, what's the, you know, you need this, this image, this logo, UTM's little tracking links at the end, the talking points for the copy.

Like what are we talking about?

What's the value?

Is there a special offer?

Is there discount?

All that stuff matters.

But you mentioned too like, so you're going through this whole process.

There's some mistakes that people make.

Can you tell us about some of these?

Like what do people screw up in the process that cost them sales in the long run?

Yeah, I think, you know, kind of just like we mentioned and, and here it's, you know, when, when the deal, there's not enough time to turn around assets, get things approved and make sure that everything runs like having, you know, having an ad go out that's not properly vetted and the results aren't tracking, you know, sure.

Like hey, we'll give, you know, we'll give you a make good here and we'll, we'll run another placement.

That's pretty standard for what publishers offer to the advertisers.

But you know, by that point in time it usually is kind of, well, you know, even if it, unless it performs like really, really well, you know, it's kind of, you know, it just leaves a bad taste in the mouth.

So you're probably not going to get approval there to rebook.

So and yeah, testing the emails and getting final sign off, that's important again so that people Know, what, so people see what's going live.

and one other caveat to that is as a publisher, you want to be able to protect yourself where, if, you know, and sometimes like, people will put this in the, in the agreement that, you know, the publisher will work with the advertiser to finalize copy.

But, at the end of the day, the publisher owns the final publishing authority.

and the reason for that is being that, like, if the advertiser is not responsive, which sometimes happens after you're sending the test, then you don't want to be stuck saying, can I publish this or not?

So, you know, that kind of stuff just helps publishers set themselves up for success.

to basically just make sure that you're not going to have these unapproved ads going out.

Yeah, and little things too, like broken links, which happen all the time.

Send yourself a test email, you can check the links.

We always recommend teams.

You know, don't just check it on your computer, check it on your phone as well.

The image that looks great on desktop, when it scales down for mobile maybe doesn't look as good.

These are all things that you can fix before, you can't fix it.

After it's gone out, you can't take it back.

So do those tests and you get the chance to make sure you're setting yourself up for success before the newsletter goes out in the world.

last thing here, getting sponsors to rebook.

You mentioned seven days after.

And there's a couple data points here that you mentioned that we should, you know, always want to share.

What do.

What should you be sharing with folks?

Yep.

So similar to.

Yeah, on the, the media kit side, the advertisers are going to want to know the unique in the, the unique numbers versus total numbers.

You can include both if you want.

say the total looks, you know, much better.

It's, it's not.

It doesn't hurt to have it in there.

But at the end of the day, they're looking for unique, you know, unique emails sent just so they could verify against what, you know, effectively what you sold them.

you know, the opened amount and again, that's within, going to be within your range and then the unique click.

So, you know, that's all the stuff that, that they're going to be looking, looking for.

but you know, a big part of that too is that that's for them to check against their results.

Like they're going to know from their UTMs what the activity was, what the sales were, what the you know, their ROAS is return on ad spend from, from their side of things.

but you still want to give them this information so that they can, they can confirm, they can validate.

And you know, and when you send it over, you know, that's kind of the message we said before.

Send the results.

Say, hey, this is, you know, the total campaign results.

Would you, would you be, you know, how are the results on your side?

We'd love to rebook something maybe on a more consistent basis over the next quarter, over the next six months or something.

And you mentioned return on ad spend is a really big one.

for instance, let's say you're a local newsletter.

You do a sponsorship with a local dry cleaner.

People don't change dry cleaners every day of the week.

Every month you pick a dry cleaner, you stick with them for years.

So you go to them and say, hey, you know, what's the, what's the value of one new customer to you?

Well maybe that customer is worth $500 over the course of a year or two.

Well, great.

If we can drive just a handful of new customers to you.

That ad was a huge success.

So understanding what they care about and then bringing it back to the conversation here to say, here's what the numbers were in terms of opens and clicks.

But on your end, what did you see in terms of new leads, new customers and understanding the value of them helps you better position.

All right, well, we drove five new customers for you.

$2,500 of value at $500 a piece.

Well, our ad was a fraction of that.

We should think about a longer term deal so we can drive a lot more business to you.

There's two more things that came in via the chat that I wanted to mention briefly.

1.

Apple MPP.

So our recommendation has been the teams.

Everybody's dealing with Apple mpp, everyone's open rates are inflated.

You don't really have to go too far to tell people our open rate might be a little bit lower because everyone's numbers are inflated.

But the one that you should definitely talk about is bots.

So some email service providers, like on Ometa mailchimp actually just released something recently, you know, can help you filter out bots.

Some don't.

There are third party tools like Glue Letter that you can plug into many email service providers that can help you filter out bots.

But you want to be real with them about bot clicks, especially if you have a lot of work email addresses or.edus.gov email addresses.

Those tend to see more bot clicks.

It's so helpful to say, hey, you want to track things on your end as well so we can match up the numbers.

We don't want to go to you and say, we drove 5,000 clicks and they go, I saw 50.

What's the difference?

Like, it could have been a bot.

So you want to be honest with folks.

All right, couple lessons, chat briefly about the playbook and let you all go on your way.

Thing number one, we brought it up earlier, but we'll mention it again.

List size really doesn't matter.

Big list is great, but I care mostly about engagement.

Engagement is the most important thing.

I want an engaged, active, clicky kind of list.

I want to know if I get your, you know, the advertiser knows.

If I get my product in front of your audience, are they going to care?

Are they going to be excited?

Are they going to follow up?

You can have a million people on your list, but if the open clicks aren't good, does it really matter?

Lesson number two is it depends is often the right answer.

A lot of you have been asking, you know, in the, we saw this in the comments beforehand, the questions beforehand, well, should I do this or this?

What's the right answer?

It depends sometimes on who you're working with.

Should you give a big discount?

Well, for the right sponsor, maybe.

For the wrong sponsor, probably not.

Should you go price higher or lower?

Again, depends on the sponsor.

Should I introduce new ad products?

Depends on what your product is, your bandwidth, your resources.

These are starting places for the conversation.

There are no hard and fast rules for everybody.

Be willing to break the rules for your newsletter.

Lesson number three is just be an evangelist for your audience.

Open rate is great.

Click rate is great.

Be the person who goes, this is why my audience is so special.

This is what I bring to the table.

It's so unique.

They don't get to be in those conversations with the sponsor.

You have to be the one who's talking and saying, this is why they're so amazing.

And lastly, the only benchmarks that really matter are your own.

Be willing to break those rules.

Don't compare yourself to, you know, a 1440 to a New York Times to 6am City, whatever it is, don't compare yourself to some of the big guys.

Try to say, look, this is what matters to me.

This is what matters to my audience.

This is what matters to the sponsor.

Let's figure out numbers that work for all us.

Okay, Last thing and then we're going to let you all go.

The Ad Playbook.

So we created this giant book.

We think it is probably the most comprehensive playbook for ad strategy that anyone has ever made.

It walks step by step through the process, answering some of the, the biggest questions that we've seen asked in the space.

It's long, it goes into a crazy amount of detail.

But it's not just the book.

We think the real value is actually the stuff you get alongside the book.

The media kit builder we shared earlier, we've compiled some examples from media kits.

From best in class newsletters.

You can see what the the best of the best do.

We have a template that Ian and Nate use with their clients.

That's a con.

It's called an insertion order.

It's a contract that's plug and play.

So, hey, we signed a new go.

I'm going to assign a new sponsor.

You don't have to go out to a lawyer and get a contract drawn up.

We got a contract.

You can use spreadsheet, to track the leads.

And most fun of all, if you buy the Playbook, the three of us, you can send us your media kit, your questions around pricing.

What are we missing?

What should we do more of?

What do you think?

And we will put together, a little dossier for you of answers of here's what you should do.

Here's where we think there's opportunities to improve.

Here's what we think you should look at to help you figure out how to take your new newsletters, to the next level, how to take your ad strategy the next level next year.

So getting the three of us on a call, very expensive.

But when you get the, Playbook, you actually get access to us to answer your questions and make sure you're putting your best foot forward with your ad strategy.

the Playbook's not going to be the cheapest thing in the world, but we're offering a special discount to anyone who showed up today.

we're going to run this for the next couple weeks.

At the end of the month, if you buy the playbook, it's $350 for access to the Playbook, the media kit builder, the access to us to answer your questions, the insertion order, all that stuff.

And we're going to do a, never done this before, but we're going to do a money back guarantee thing.

This makes me feel a little like I'm an infomercial salesman.

But still, I think this really matters.

We really believe in this thing.

If you don't make at least 500 bucks off UH ad sales in the 100 days after buying the Playbooks if you don't make your money back and then some we will refund your money no questions asked.

We're going to send you the link to buy we're going to send you the recording from today on all the slides we'll share that with you later this week it's all going to go on sale Wednesday so keep an eye out for that email.

I want to say lastly there were a couple questions we're going to do our best to try to reach out to folks as well who ask them the questions with some one offs but just want to say most importantly thank you to all for joining us and thank you to Ian and Nate for coming on and sharing your expertise.

Really really appreciate you sharing all these great ideas keep an eye out for more details and updates soon and thanks everyone for joining us today.

Have a great rest of your.