Send & Grow by SparkLoop

Enjoying the podcast? Then you'll LOVE the Send & Grow newsletter where we share deep dives, tips, and news for smart newsletter operators like you.

Welcome back to another episode of the Send & Grow podcast. This week, SparkLoop's Dylan Redekop chats with Ryan Sager & Jesse Watkins of Who Sponsors Stuff. 

In this episode, Dylan, Ryan & Jesse discuss…
  • How they became Experts: Ryan and Jesse's journey from managing a multimillion-dollar newsletter ad division to founding Who Sponsors Stuff
  • 2023 Ad Market Retrospective: A look back at the challenges and shifts within the newsletter ad space in 2023, setting the stage for what's to come.
  • 2024 Ad Market Trends & Predictions: What newsletter operators should be paying attention to in 2024. 
  • Starting with Sponsorships: Whether you're at 1,000 or 100,000 subscribers, uncover the right time and strategy to introduce ads to your newsletter.
  • Pricing and Performance: Learn how to set your ad rates and ensure your ads perform well, enhancing sponsor relationships and securing renewals.
  • The Future of Newsletter Sponsorships: Ryan and Jesse's take on the balance between subscription and ad-supported models, and why ads can be a win-win for your content and audience.
  • ...and much more!
OTHER LINKS MENTIONED
Who Sponsors Stuff
The Newsletter Conference (use code SPARKLOOP for $100 off your ticket!)
Ryan on LinkedIn
Ryan on Twitter
Jesse on LinkedIn
Dylan on Twitter/X
SparkLoop's Paid Recommendations — the game-changing way to instantly monetize your newsletter.
SparkLoop Partner Programs — grow your newsletter at 10x speed.
SparkLoop Affiliate Contest

What is Send & Grow by SparkLoop?

Discover how the best media brands and solo operators are winning at newsletter growth & monetization.

Hosted by SparkLoop's cofounder Louis Nicholls and SparkLoop's newsletter nerd, Dylan Redekop—we take you behind the scenes and share the strategies, trends, and tactics you need to know to build your email audience and revenue.

Featuring exclusive interviews with the smartest media experts and operators out there today. Including from the Hustle, Morning Brew, Workweek, The Pour Over, and more.

EP 41 - Ryan & Jesse Who Sponsors Stuff
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Ryan Sager: [00:00:00] We see people say, Oh, the value proposition of our subscription is that we won't show you ads. Please don't do that. That's, you know, we've never found that the consumers that readers are that.

Dylan Redekop: Welcome to the send and grow podcast. I'm your host, Dylan Reddick off in my day job at spark loop. I spent all my time analyzing how the best newsletter operators and media brands in the world grow and monetize their audiences.

I get a behind the scenes look at how they're growing their newsletters and driving revenue, and there is so much to learn from their success and from their mistakes. With this podcast, you get that access too. Every week, I sit down with a different guest from industry experts to successful operators, and we go deep on the stuff that you need to know so you can become really effective at growing and monetizing your newsletter.

Today on the Sending Girl Podcast, we have round two with Ryan Sager and Jesse Watkins from WhoSponsorStuff. Ryan and Jesse joined us a year ago to talk all things newsletter ads and sponsorships, and today they're making their triumphant return. I brought them on the [00:01:00] podcast to share the most up to date insights into the evolving world of newsletter sponsorships.

With their rich backgrounds in media, Along with bringing in millions in sponsorship revenue for newsletters, Ryan and Jessie have their fingers on the pulse of the newsletter sponsorship world. Today we're diving into what 2024 holds for the newsletter sponsorship space, when you should introduce sponsorships in your newsletter, and how to ensure your ads resonate with your audience and sponsors alike.

Ryan and Jesse, it's so great to have you on the Standing Room Podcast. Ryan, how about you start by letting us know why newsletter operators would be wise to listen to you guys when it comes to newsletter sponsorships.

Ryan Sager: Yeah, absolutely. Thanks for having us on, Dylan. I always happy to do stuff with SparkLoop.

So, yeah, uh, I, uh, my background is in big media, Wall Street Journal, Time Magazine, places like that. And, uh, kind of in the last five to seven years, I've been deep in the newsletter space, uh, Jesse and I met a company called ladders, where I built out a product of a daily [00:02:00] newsletter about, uh, the workplace future of work.

And, uh, Jesse came in and monetize that newsletter through direct newsletter ad sales. And, you know, we kind of. Quickly stood up a 2. 5 million a year division within ladders just on that direct media sales. And then we did some third party sales for a little while after that. And out of third party sales and the need to sort of track who was sponsoring newsletters and who was advertising in this space, what was initially an internal tools and air table I built for myself.

We decided, uh, late one night I looked up the domain name, who sponsors stuff. com and said, we should, uh, package this thing up and sell to publishers. And so that's what we did. We do now about 60 publishers use us, everyone from Morning Brew, Daily Upside, Flipboard, and tons of independent and traditional media companies are using us to power, to help power their ad sales and their intelligence on the ad market.

Jesse?

Jesse Watkins: Yeah, Ryan covered a lot of it. Uh, you know, my background is in, uh, [00:03:00] advertising sales. I was actually, uh, print advertising in like pregnancy and pediatric and then had gone onto Ladders and, you know, the newsletter. We were fairly early in newsletter. Then this was 2018, so like as an example, morning Brew was one of our early clients buying ad inventory and really just starting to scale then.

Yeah, so we were able to scale, uh, ladders newsletter revenue up to like a multimillion dollar. annual revenue driver, and then took everything on the road to do third party ad sales. And out of that, I built a database for prospecting that now grew into what is who sponsors stuff. Yep. We just are all about solutions for newsletter operators,

Dylan Redekop: traders.

Very good. Awesome. Okay. So we have established you guys are, uh, known, you know what you're talking about when it comes to this stuff. So with that out of the way, I would love to get into a quick retrospective of 2023 in terms of kind of what you guys saw in the ad space, maybe in comparison to the past couple of years, and what some of the biggest takeaways were in 2023 in terms of the newsletter ad market.

Ryan Sager: Sure. [00:04:00] So, you know, 2023 ended up being a bit of a rough year in the market, both in newsletters and just all over the media, kind of the recession that never happened was sort of looming out there and marketing budgets got cut. And we've seen. A lot of sponsors push hard to kind of push everything to performance marketing.

That is, they only want to pay per acquisition or per click, uh, CPC or CPA deals. And, you know, what we've seen in that, in that environment is that the brands, especially kind of among our clients that had managed to thrive, despite that are the ones who, you know, double down on, on prospecting. Uh, which our tool is just, you know, one of many ways you should prospect.

We, we hope it's a, it's a core one, but you know, there's a ton of different ways to prospect and look for new advertisers and to build out your pipeline. And so the ones who did it themselves and really owned their sales and built out those pipelines, uh, survived and thrived. And, uh, yeah, I mean, Q1, 2024 is looking a lot better so far.

Definitely hearing great [00:05:00] things from clients as far as. Hidden Q1 goals already and, and, you know, just things are looking much brighter right now. Okay. So,

Dylan Redekop: 2020 was rough. You mentioned the looming recession. Were there any other reasons why you think it might've suffered a little bit in terms of the, was it in a lack of interest or lack of performance from paid ads that people maybe, um, brands were a little more hesitant?

To throw money at or was it something

Jesse Watkins: else?

Ryan Sager: No, I mean, I think overall, the sort of macro picture is that as social, you know, as like meta and different social forms of advertising are getting rougher and with cookie deprecation, you know, a lot of money is actually flowing into the newsletter space in terms of people.

Advertisers are looking for places where. Whether it's a newsletter, whether it's influencers, people who have sort of, you know, first parties, zero party data, people who have very personal relationships with their audiences. So, I mean, at the macro level, newsletter advertising is only growing. I mean, we, so we [00:06:00] track about 500 newsletters and who advertises in them.

So, you know, we see every day, all the new advertisers flowing in, uh, across those 500 newsletters, which are a mix of B2C and B2B. You know, 20 a day is, is easily the average of like new brands showing up in newsletters. So there is, there is a ton of new stuff and that's, that's been very consistent across the time we've been tracking all this.

So brands are still coming in, uh, whether those are the bigger brands, uh, suddenly showing up or whether it's, you know, a lot of kind of middle market brands and TTC brands, uh, and smaller brands, uh, in the B2B space. So. Yeah, we've, we've only seen good things that, you know, obviously we've taken a big bet that the newsletter market is only growing as, as sparkly passes, as everyone watching this, everyone watching this podcast is, is taking a bet on newsletters, presumably.

So yeah, we were very confident in that.

Dylan Redekop: Okay. Very good. Very good. Okay. Let's talk about 2024. Now you did mention, um, that the first quarter is looking. [00:07:00] pretty promising, a lot better than 2023. Well, let's say last year around this time, you guys were on the podcast and you made some predictions about, you know, what we would see in 2023.

What do you think? Similarly, if you're on this podcast a year from now, what do you think we'll be, we'll be talking about what happened in 2024 when it comes to the ad and sponsorship market? Are there any, are there any major things that Newsletter operators should be paying attention to right now in terms of ad sponsorships for newsletters.

Ryan Sager: Yeah. So, I mean, I think one of the big things we're going to see is obviously you've got some of the ESPs trying to make a push into kind of selling ads across their networks. Uh, you know, people who want to build an ad network across the ESP, you know, we're definitely seeing mixed results from that. I think we get a lot of, you know, we talk Probably do about as many newsletter publishers as anyone in the world.

I mean, I say that talking to spark loop, who I'm sure is, is right up there or more, but we're, we're talking to operators who are concerned with their revenue, who are the ones in charge of revenue. And, you know, they're, they're not thrilled [00:08:00] with any, any networks, any marketplaces, and they're coming looking for direct solutions.

So I think what we don't want to see happen in the newsletter space is to sort of put everything into marketplaces and networks. So you just essentially recreate. Programmatic advertising but in newsletters right you know the thing that's special about newsletters is is a voice is a personal relationship with the readers that's why i mean that's why you think of like a morning brew and what they made famous with their like very bespoke.

Ad copy and them writing the ad copy and it very much being in their voice. Like that's what works about newsletter advertising. That's what's special about newsletter advertising. So trying to sort of templatize it and put it all the same ad across, you know, a thousand newsletters, there's a place for, you know, the live intents of the world, the, the, the programmatic fill, but it's, it's not what should be powering like quality newsletters in today's day and

Dylan Redekop: age.

Is there a time and a place for programmatic ads in these

Ryan Sager: letters? Yeah, I mean, absolutely. I mean, what we, you know, we can [00:09:00] talk more about this down the road, I think, but yeah, well, there should always be a sort of waterfall, I think, in terms of, you know, you want, first of all, to sell a direct ad at a great rate.

After that, maybe you have a third party, you know, sales agency helping you out on backfill. And then after that, if you need it, and especially if you have scale, this doesn't really make sense if you're a smaller operator, but if you're, if you're a giant traditional media company and you've got just millions of people on your list, uh, yeah, there's definitely a place in that waterfall where you're going to get some significant revenue out of putting something programmatic as a backfill unit.

Dylan Redekop: Jesse, I want to give you the opportunity to jump into it. If you do, do you have any, any ideas or thoughts? Yeah, just on,

Jesse Watkins: uh, the backfill piece. And again, we'll probably get into this a little bit further on the third party stuff, but yeah, there's absolutely a place for the ad networks. If you're just starting out and you want to test it, advertising's something that's going to be viable for you as you scale.

Additionally, if you're a hobbyist and would like to make some additional revenue off of your newsletter, I just don't see them [00:10:00] driving revenue for like a morning brew or a major media brand.

Dylan Redekop: Mm hmm. Okay. Yeah, fair enough. So let's say, let's say you guys are advising, you're being super generous with your time.

You're advising a rapidly growing newsletter in a niche category that's, you know, decided to monetize with a newsletter sponsorships. At what point should, you know, the question seems to be like, when am I big enough to start selling ad slots? Is it a thousand subscribers? Is it 5, 000? Is it even a subscriber number?

What is, what is kind of that, I guess, rule of thumb that you would say? And, And any other things that would be in consideration when you make that decision? Yeah.

Jesse Watkins: So I want to separate this out when you say niche from like B2B versus consumer. I think it's like a decent way to think of this. Okay. So B2B audiences can really be monetized that something like 5k, 10k through sponsorships, events, and a number of ways.

So it's more so like the quality of that audience and like how desirable that audience is in the B2B [00:11:00] verticals. Consumer, you need a little bit of scale, especially nowadays, as there's so many consumer facing newsletters in this space. I would say consumer, you know, we used to say like 50k, you could probably start running a lot of deals at 50k, but Do you really want to get more scale 100k plus if you're trying to, you know, be like the next daily upside or something of those likes on consumer?

Yeah, b2b, I think at 10k, you're good enough to start. First thing to do is always call out to your audience and then take it from there. If people are coming to you as you're in your audience, you're in a b2b niche, they trust you for, you know, Whatever content you're delivering to them every day, weekly, so they know if they are in your audience and they are the target demo, then it's a great place to sponsor.

Dylan Redekop: Yeah, I think the one thing we've had actually, a number of guests on our show, newsletter operators have said is, my first sponsor was somebody in my email list. Like it was, uh, somebody already reading the newsletter knowing like, hey, I think this audience is, you know, Perfect for our brand or our business.

So that's a great first step. And that was my next question. [00:12:00] What's the first thing when they realized, okay, we're at that point where we can monetize with selling ad slots. What's the first thing we should do? So start reaching out or letting your audience know that you, you have ad slots available. Uh, Jesse, let's say you've let your Your readers for your newsletter know that you're going to run be running ads and to reach out if they'd like to, you know, inquire about a sponsorship, but nobody does.

It's crickets. You don't hear anything. What is, what is the next step? What's the best thing for you to do as a newsletter operator to try to find your first sponsor?

Jesse Watkins: Yeah. Uh, this is something that we had done, you know, I'd always done in sales. I'd really defined what our Current product does, uh, subscribe to a bunch of newsletters in your vertical and check out who's sponsoring them.

You know, an old trick used to be just forwarding that email over to that marketing director. Like, Hey, so this creative you're in, I have a similar audience. Let's chat, you know, and then at scale, obviously a product like who's sponsored stuff. We're doing that at mass scale, but yeah, to personally track like 10, 15, even the basket of 20 newsletters, uh, in your verticals and reaching out, I think is a great [00:13:00] way to prospect, you know, these sponsors understand the newsletter channel.

They're in the newsletter channel. So those conversations could be a little bit more transactional pointed towards closing.

Dylan Redekop: Yeah, I've spoken with other, you know, ad sales pros. It is basically like you want to reach out to people already advertising in newsletters because you know, they are, they've bought into the concept or they at least are, you know, willing to entertain as opposed to somebody who's never done it before.

Then it's like, you know, trying to first convince that. Selling ads or advertising in a newsletter is worthwhile and then try to pitch them on your newsletter as well. So that does make a lot of sense. Then how would you figure out what to charge for an ad slot? And should you have one? Should you have multiple?

Yeah.

Jesse Watkins: So I am a big fan of doing the basics really well first, right? So I like to fill, fill inventory, right? Especially on consumer facing newsletters. We'll start with consumer. I think fill is like the most important thing, making sure that we are at. You know, 90 percent plus fill rates for the advertisers with that set on [00:14:00] pricing.

Obviously we like everything to be flat fee or some hybrid off of flat fee, but preference to flat fee over anything performance based the way I like to go to market with pricing is off a multiple of that sponsor click, right? Because I know if a consumer facing brand, like I've been several watches or.

Well, I'm not super relevant now, but some of the consumer facing brands, if they're running a babble, for example, if they're running their campaigns anywhere between one to three, maybe 4 on a CPC basis, they're satisfied. So I know if I have, if I present a flat fee, that is a multiple of that clip number between one and three, then I'm not going to be wildly out of market on these campaigns.

Gotcha.

Dylan Redekop: Yeah. And I guess it would be hard to, if you've never run an ad before, hard to establish what a click number is. So there'll probably be a little bit of like a bit of testing going on in the beginning, or would you, would you defer to a lower rate to start or how would you approach that if you've, you know, it's a chicken and egg kind of a, kind of a situation.

Jesse Watkins: [00:15:00] Ad networks are a good way to test. Um, you could use ad networks or swaps. I mean, swaps are also like a decent test of an ad number, right? Like just a swap with another newsletter. Yeah. I would really use like an ad network to try to. Let's figure out what that is, uh, really define your ad slot. When starting out, I like the simple ad slot of logo sponsorship up top, and then the second or third piece of native content in the newsletter.

If you could simulate that ad slot or whatever it is, even with house content, just to get an idea of how much it would, how much traffic you won't be able to drive. Okay, cool.

Dylan Redekop: So we found a sponsor, we figured out a price for our, for our ads. Ideally, you'd love to sell, you know, a bundle of ads. Let's say we've sold a bundle.

What happens if you sell, say, a month's worth of weekly ads? So like four, let's say four ad slots. What happens if that ad doesn't, you know, the first ad goes out and, you know, performs well below expectations and, you know, Is that going to be an issue going forward? What, what, how can you approach that from um, the newsletter operators perspective when you, you see the [00:16:00] numbers much lower than anticipated?

A few notes on this. We'll be right back to this conversation after a quick word from our sponsor. Last year, we launched the most

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Dylan Redekop: network and unlock millions of dollars

Ryan Sager: in easy extra revenue by recommending the world's best newsletters.

You get a 30 percent commission. Win win. It's that easy. See you on the

Dylan Redekop: beach. And now back to the episode. What happens if that ad doesn't, you know, the first ad goes out and, you know, it performs well below expectations [00:17:00] and Is that going to be an issue going forward? What, what, how can you approach that from um, the newsletter operators perspective when you, you see the numbers much lower than anticipated?

A

Jesse Watkins: few notes on this one, uh, why we sell bundles as opposed to just one offs, because if we're bundled and, uh, you know, in your weekly example, uh, if I sold a package of four weekly sponsorships to somebody, I'm not going to be running those every week, right? I think daily is another good example. If I'm running a daily newsletter and I just sold five.

Sponsorships to somebody, I'm going to spread these out probably like I'll spread them out weekly and then maybe even another week of space somewhere in there just to give us time to test copy and see how our audience is responding to the changes in copy. Maybe it's a landing page change. But should you run that first ad and it's way below expectation, I think that's where you kind of want to regroup, take a look at the creative assets, do another run.

And also if you're starting out, Make goods or your friend. You really want to deliver for advertisers. That's how you establish [00:18:00] sustainable, long standing relationships, is making sure these sponsors are working with your audience. A good way to avoid coming in way below expectations on those initial runs is to really understand what this brand, the sponsor, the marketing director is looking to achieve out of a successful campaign.

How do they define a successful campaign? How can you best make that happen? You're like a mini marketing coordinator for that brand, really. Is that so? That's the way I thought of my role at Ladders, right? I was like the marketing coordinator for all these brands internally at Ladders, making sure we are running strong campaigns.

And I think you have to be rather meticulous about that.

Dylan Redekop: Yeah, that makes a lot of sense. So if you, if you've found some success with the sponsor, your ad slot, what are three things or a few things that you can do to increase the chances of renewal? Maybe better yet, let's say the ad, the ad slot or the bundle has run its course.

What is the bare minimum you should be doing as a newsletter operator to ensure a [00:19:00] renewal? So

Jesse Watkins: ideally If you're selling in bundles, they are reaching out to you after a few runs and saying, Hey, you know, uh, we need more inventory. Let's read up. We saw a ton of that ladders, uh, a lot of publishers. Nice.

Alternatively, it's really again, like staying on top of things like sponsorship. Isn't just this thing. Ad revenue. Isn't just this, Oh, nice to have, or It's really something with a lot of effort and thought behind it could scale and could provide a lot of value for your readers, sponsors, and grow the brand altogether.

So being open, again, understanding what their goals are for the campaign, and then consistent campaign reporting, just letting them know where they stand on metrics. Doing temperature checks, and then you should be in communication after all these sends to understand. Okay. Well, this advertiser is happy, not happy.

It shouldn't be. We ran them for the month. And now at the end of the month, I don't know if how they're feeling or are they going to renew or not. You should have a little bit more insight, be a little bit more hands off.

Dylan Redekop: And in terms of reporting, what should What are the most [00:20:00] important metrics that you should be reporting on?

You know, as metrics

Jesse Watkins: become slightly less reliable post NPP with open as it clicks, uh, it's still important to have an understanding like these are, it's our open rate. It's the same for everybody, right? We're all doing the same stuff. So open rates, click numbers, Really, any insight that you could provide, any data you could provide as to how your audience reacted or engaged with the sponsor, maybe benchmarks up against other sponsors in the space.

And then also on the upside, like having an understanding of how your audience responded to this landing page versus another landing page, how your audience responded to this copy versus another set of copy, maybe a little bit of A B testing. But yeah, you really want to present your opens, your clicks, and like all relevant data to

Dylan Redekop: those adsense.

Amazing. Okay, great. Let's move on here from just the steps and how to sell newsletters. Let's talk about ad sales agencies, third party sales, and ad networks sort of as a bundle. You know, newsletter operators are quite often, especially in the beginning, they're solo operators. They're doing this all by themselves.

They're in charge of the content. They're in charge [00:21:00] of, you know, uh, selling ad spaces if they, if they are doing so, you know, daily operations of publishing newsletter and all that sort of stuff. You know, at what point does it make sense for them to Go with maybe a third party agency or somebody hire somebody basically to manage their ads and what would be the main benefit of doing that?

Yeah.

Jesse Watkins: So third party, whether it's, uh, you know, ad networks or a third party sales org, or, you know, more of a marketplace type build, they all have their utility and time. It depends on the publisher, right? So if I'm just starting out and I'm small, a third party sales org may not Necessarily want to take me on like if I haven't proven that I could monetize my audience directly then There's sometimes this thought process of oh if I just pass on revenue to some third party, uh problem solved But if you can't solve it yourself Then what makes you think a third party is going to come in and do that automatically?

And I think in that same kind of that same logic applies to some of the marketplaces, right where these are more [00:22:00] passive So you're going to get out what you've put into it, which might not be the strongest revenue Ultimately, I think Uh, or at least the way I ran it at ladders was fill all our standard inventory, uh, in house.

And then, yeah, I had multiple third parties that would be running discount rates on me for remnant inventory, right? They could offload remnant inventory and also a lot of utility. If there's an advertiser that's running absolutely everywhere that I can't get to directly, and it's placed through one of these third party orgs, that's a great way to get at them as well.

And As Ryan noted earlier, it is great to always have that waterfall for fill. Yeah, we're big believers that, you know, you really want to maintain fill rates is how you maintain solids function.

Dylan Redekop: Yeah, that makes sense. I mean, you got so much going on and, and if you can take as much of that on, especially like the, the logo sponsorship, you know, manage that yourself.

What is a typical Rate that a third party. I like I honestly don't even know what what they would charge for phil Is there is there kind of a uh industry average for something like that? [00:23:00] Standard

Jesse Watkins: rates are anywhere from 20 to 40 percent that kind of sounds like a little bit of a variance there But it also depends on your audience size Yeah like if I And this comes from our experience in third party sales if I had to go outbound for you in your 2030k consumer facing audience might not be the most desirable.

Uh, That's gonna be a lot more lift. So there should be a higher commission percentage off of that. Also, we're talking about much smaller revenue numbers here. So that's also into

Dylan Redekop: consideration. Yeah, right. So more work, less revenue, the, the commission rates going to go up essentially. Yes. Nice. Nice. Okay, cool.

So we've talked a lot about ads and, you know, how to start doing them and that sort of thing. But maybe a basic question we should have started with was should every newsletter do sponsorships? Or is it only beneficial for a certain type of newsletter? So, you

Ryan Sager: know, it really does depend on what, uh, what you're doing.

It depends a lot on audience size. If you are in a niche where people are willing to pay for content, uh, I'm thinking maybe like cooking content here, right? Maybe you don't [00:24:00] have, you know, 200, 000, 500, 000 people reading your cooking, you know, content, but maybe you just have awesome content on that and you can get a thousand people to pay a membership, a membership model is probably better for you than, uh, than an advertising model.

Now, look, that's not to say you can't be hybrid. I think a lot of people are scared. Like, Oh, if somebody is paying a membership, I dare not have an advertiser involved, but, you know, again, going to like that cooking example, like, okay, you've got a thousand people. Paying for your cooking membership, that doesn't mean that, you know, uh, whatever, you know, kitchen appliance brand, uh, you know, can't be involved in your video in some way.

Like, you know, if you're kicking to a video or you're kicking to a special issue, like definitely you can do hybrid. And one thing just to caution against, cause we've seen this a lot, we see people say, Oh, the, the value proposition of our subscription. Is that we won't show you ads, please. Don't do that.

So that's, you know, we've never found that that consumers, that readers are that offended by ads, that that's a great value proposition. And then if you are going to run ads to [00:25:00] your free audience, you're cutting out the best part of your audience out of the advertising pie. Like all of a sudden, the people who have the money to buy a subscription, the people who are engaged enough to buy a subscription, uh, all of a sudden they're cut out of your advertising audience.

Uh, that's. That's just sort of bad on both sides. Um, people really get dogmatic about it, but like newsletter ads are so different from web ads, right. Or from Hulu or Netflix ads, you know, Netflix. Yeah. You're going to pay not to have the ad probably because you know, you don't need to see, you know, your, your show interrupted every four minutes.

A newsletter ad is. In the best case additive, you know, we, we do think that if it's a, a well matched sponsorship, somebody should be learning about a product that's interesting to them. If you're reading a B2B marketing newsletter and somebody has got some awesome, uh, you know, marketing tool that they're advertising, like that should be a win win on all sides.

So, you know, it should be at least additive. And if it's not, You know, if the user, for [00:26:00] whatever reason, if the reader doesn't find it, you know, particularly interesting, it's, you know, it's the same as an ad in a print newspaper or a print magazine. And like, you just don't pay attention to it. It's, it's not offensive in the way, like a pre roll on a video or like pop ups on, on a website are it's.

You really shouldn't feel self conscious. I know we're talking around book here a little bit, but you know You really shouldn't feel like you're offending anyone by having sponsored content. Yeah, you could you could do it in a way That's offensive. But if you're doing, you know normal advertising Uh in a nice way, uh, your readers are not going to be mad at you.

Dylan Redekop: Yeah, I agree I think the you know, if you look at Newspapers that you pay subscription to receive magazines that repay your subscription. There's advertisements in those as well. They don't detract from the experience. In some cases, maybe they do because it's all ads, but, uh, hopefully you wouldn't be paying much of a subscription fee for those.

Nevertheless, I think when you look at from that standpoint, where it's not actually stopping you from consuming the media, whereas a, you know, a pre roll ad on YouTube or maybe an ad [00:27:00] in, in Netflix is going to have that That real interruptive factor to it. So I think that's, that's a great point because people often think like, well, if I'm charging you five bucks a month or 12 bucks a month for my newsletter, then I can't put ads in it.

Right. So thank you for mentioning that. Cause I think, I think you're absolutely right. It's been great having you guys here talking to all things ads, but we'd be remiss not to quickly chat about something that's coming up in May, which our audience should be interested in. Um, so talk to us about the conference you guys are putting on in May.

Yeah.

Ryan Sager: So, you know, hopefully you're watching this, uh, at home, uh, or at work, uh, before May 3rd, 2024. So, Spark loop is actually the keystone sponsor of this, but we're putting together the first ever newsletter conference, May 3rd, New York city at the time center full day conference VIP welcome dinner before nice cocktail reception after.

So yeah, we've really, you know, we've been in this space a while, as we've mentioned, and we've been to various media conferences and we just [00:28:00] found as newsletter people that there was so rarely anything that was like. Really relevant to this major new sector of the media industry. And, you know, maybe it gets a panel, maybe it's an afterthought somewhere.

Uh, but you know, about two years ago, we just started looking around at this and saying, there is a need for people to convene in this space, whether you're a solo founder, an independent newsletter company, everyone is so spread out and so siloed. And you're not in a room where you could talk to other newsletter operators.

Uh, and if you're at a major org, uh, if you're at a traditional media company, if you're at the New York times. If you're at Bloomberg, uh, if you're at Hearst and you're the newsletter person there, again, you're siloed. You've got this little fiefdom inside your, your company. That's maybe not, doesn't really know that much about newsletters.

It's a totally new thing to them, like treating it seriously. So we started first a dinner series, uh, that we have been running with Dan Oshinsky, uh, that's called dine and deliver, and we do kind of private dinners around the country and get together 2024, [00:29:00] uh, newsletter operators, newsletter people, and those were just.

You know, smash success. So you, it's very, very small. So we do have to have people apply to join them. And, you know, we found, we found about 700, 800 people applied last year and we could fit in, you know, again, about 2024 dinner. So, you know, we knew there was just this huge urge to convene. And so in, um, mid February we announced and the early bird tickets have just kind of flown off the shelves.

And, you know, it's a great, it's a great speaker lineup. I'm sure the show notes will have. All the, all the website to go look at this, but, you know, we've got some of the biggest names in the space, people are going to want to hear from, and it's, you know, it's really just going to be a great chance to see the programming from the stage is going to be exceedingly informative.

And just like, you know, we've been through this content at the dinner so many times, and it's so great to like share it with a much broader audience. Like you're going to go home with actionable. Very actionable information. You're going to get great insight into what other folks in the field [00:30:00] are doing.

Uh, and then just the networking again, like people just don't have a place to like meet each other in this, in this industry, in this burgeoning newsletter industry. So, uh, we're very excited and yeah, I mean, we, we expect, you know, three to 400 people in New York city spending a whole day talking about newsletters.

So it should be, it should be awesome.

Dylan Redekop: Amazing. So. Just to do a little tease, we definitely will include the link in the show notes, it's the newsletter conference. com. But I mean, we've got speakers like, you know, Dan Oshinsky from inbox collective, uh, Jacob Donnelly from a media operator. There's Erica Burghardt from 1440.

She's ahead of growth there. Chanel Basilio, who we just had on the podcast is going to be there. Matt McGarry, who many people know as a, you know, a paid Facebook ads expert. He'll be there. If you're in the newsletter space, you will know who these speakers are. And, uh, I think it's going to be, Really awesome.

A really awesome event. May 3rd, New York City. Go to the newsletter conference. com and check it out and reach out to Ryan and Jesse. If, uh, if you have any questions, I'm sure they'd be happy to answer them for you. [00:31:00] Gentlemen, thank you for joining us today. Two times, two times, two years in a row, twice on the podcast.

We're gonna have to make this a yearly tradition, maybe even more frequently. So we'll, we'll schedule our 2025, uh, reconvening next year, but, uh, thanks for coming on again and. Any, any party words on where people can find you guys yourselves? We talked about the conference, we talked about WhoSponsorsStuff, uh, social media where people can follow along what you guys are, are sharing on there.

Ryan, you can go first. Uh, yeah,

Ryan Sager: no, I mean, we have, we have social feeds for all of it, but yeah, just WhoSponsorsStuff. com and thenewsletterconference. com are the places to check us out. And yeah, that's, that's

Dylan Redekop: where to find us. Cool. Awesome. Thanks, guys. It was a pleasure having you on and, uh, good luck at the conference.

Uh, we're looking forward to it. Thanks

Jesse Watkins: for having us.

Dylan Redekop: Thanks for listening to this episode of the Send and Grow podcast. If you like what you heard, here are three quick ways that you can show your support. Number one, leave us a five star rating and review in the podcast app of your choice. Number two, email or DM me with some feedback with your questions or with suggestions [00:32:00] for future episodes.

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