Monetizing the Inbox: Jesse Watkins on Newsletter Sponsorships & Growth

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Welcome back to another episode of Audience Bridge Insights. And today I have Jesse Watkins, the co founder of who sponsors Stuff and the newsletter conference or the newsletter events company. Not sure which one's company. Jesse, nice to have you here.

Thanks for having me.

Chris, can you go and just give us a, you know, a quick version of what got you into the newsletter world and what you're trying to solve with who sponsored stuff and these conferences you guys are kicking off or you've been doing for the last couple years?

Yeah, sure. So my background was actually in print media. I was doing ad sales for these little digest size publications in like the pregnancy and pediatric spaces. So lots of knowledge there. I had joined a company called the Ladders. It was a job site. My co founder and sager, he was already there. He had built what was called Ladders News. His background was big media, the journal and magazine. He had built Ladders News. I went to monetize Ladders News. We used a newsletter as our primary distribution channel driving traffic to the site and the link roundup. And to me it just seemed like selling adjacent content kind of not far off from print. And we just crushed it on ad sales on that latter's newsletter. We ended up scaling Ladders News to like a multimillion dollar revenue driver annually had left there. And then Ryan and I were talking like 1440 and a bunch of brands were reaching out. This was Covid 2020. So Ryan and I started doing some outside sales for for a lot of these pubs. Something I'd always done to find sponsors and prospect sponsors is subscribe to a bunch of different newsletters in whatever verticals I'm selling into when we're doing outside sales that just wasn't cutting it like the scale of clients we were taking on the different verticals they were in. So Ryan came up with a system to kind of automate some of that. And what started as like an internal prospecting tool grew into what is now who Sponsor Stuff tracking somewhere around 800 different newsletters. I believe we have over tell you exactly how many over 10,700 unique sponsors in the database. And then in promoting who Sponsor Stuff just realized there wasn't, there wasn't an event space for newsletters. So that's how we started the dinner series called Dine and Deliver with Dan Oshinsky of Inbox Collective. That was a hit. We're now on year three of the dinner series and use that audience to build up the newsletter conference. And then we have additional in person events coming up. Like we have the Business of local media conference coming up in October in Salt Lake.

Is that, is that local media? Is it based on just the newsletters specifically or is it getting more into like the actual local events and stuff like that?

Everything. Yeah, it's media. This isn't a newsletter specific build. So kind of the full, the full scope of these local builds and our, our take on that is really like the business of this space. Blue Engine Collaborative came to us after the second year of the newsletter conference wanting us to spin something up for, for local media kind of with that same perspective or point of view on like a profitable or revenue driven business. And so much of local is like, you know, grant driven or really struggling to keep the lights on right now. So we think learnings and lessons could help save a lot of that space.

Cool. As far as who sponsors stuff, what's some surprising insights you found out for the 10,000 plus newsletters you're monitoring and all the advertisers?

Yeah, I think it gives us a pretty good view. I mean I could argue we have like one of the most, one of the best views of sponsorship generally in the newsletter space specifically. So the types of sponsors, the types of deals as well. You get some insight into you know, in the COVID era or a lot of ad, ad spend freezes and then the explosion of like performance models. Those seem to have you know, a lot more stickiness than, than I would have, than I would have argued if you told me that in 2019 all of Newsletter will go strictly performance. I probably would have argued otherwise. So just a lot of those insights and also the types of new newsletters. We're always like looking for new newsletters. You kind of, we saw that trend from web3 to NFT to AI to crypto, now back to AI and some of these newsletter builds.

So the. Are you seeing like the bigger brands, bigger traditional brands out there, Nike or you know, some other CPG brands, are they starting to advertise more, invest more on, on newsletter ads or is it still kind of more focused on that performance based kind of network of advertisers?

Yeah, I think the, there's a few reasons. I think a lot of the blue chip brands don't necessarily spend a ton on newsletter or it's not like a priority one. Just the way the industry developed, we sort of run independent of the big buying selling agencies. Right. Like it's not, I mean sure at Ladders I would get an RFP from some of the agencies, but Ladders we had a ton of scale. Right. Like it was a very large audience and a bit of brand recognition from Mark's news appearances, you know outside of like front office sports or those brands could get or like the JSK got some of these like more CPG blue chip partnerships tied into social or like multichannel newsletter specific channel, lots of different B2B sponsors. I mean now you're seeing the maturity of like the AI brands that were raising or now now have like really solid B2B products. So we see a lot of that and a lot more like smaller brands than, than the large blue chip CPG.

Brands when it comes to you know, getting a news off or started like when she start monetizing it.

Yeah, I think right away, you know we were at an event in Austin, it was the newsletter Marketing Summit and Andy Meccasin, he's the co founder of the Assist, he gave a really, really detailed like on how they're monetizing their welcome series right through some quizzes and some offerings and it gives them some data and some opportunities to sell products, some of which they're getting affiliate on, sell courses, etc. I think when we think of newsletter monetization, you know, as soon as you have an audience that's following you, that's following you regularly, you're sending on a regular schedule. There's different ways to monetize, not always directly with sponsorships out the gate, but there are ways to monetize right away.

That comes into like the, the Beehive boosts or Spark Loops booths or whatever. Trying to get them on like a kind of a co reg sign up and monetizing the welcome flow. What's the biggest mistake you see that operators are doing when they're trying to sell ads?

Yeah, I think so. The way I always think about newsletter sponsorship is you have to or media sales in general. But it's very true for newsletter media sellers. They are, you're kind of a brand steward for, for whatever your sponsors are. Right. The way it works is you're lending the voice, the publisher is lending their voice to this sponsor to speak to an audience that they should hold in high regard. I think it's important to make sure that there's like strong fits there. So just being like honest in about like open rates and size and like audience demos will always lead to better successful sponsorship partnerships over the longer term. I also think like bundling like don't discount the audience like a lot of sellers will try to sell one offs or just smaller swaps and as well as like having a clearly defined ad product. Sorry, this is a little all over the place. But like I think clearly defined ad product is also like a mistake a lot of early newsletter operators will make on the sponsorship front.

And then as far as like what's the most important metric for, for the sponsor, the advertiser. Is it still the acquisition in the end more you know, direct response conversion lead gen or are you seeing, you know, more to the brand development?

Yeah, so I mean it depends on the sponsor, the publisher, but generally, I mean, right. Any advertisement in. We have a lot of like doctor in the newsletter space. And the way when I'm selling a sponsorship, this is why I'm going to be open about like my, my opens. The type of audience I have and click throughs matter a lot here too because then that marketing director is going to look at all of that and say, okay, we can anticipate X conversion percentage based on this demographic info and the traffic you're sending us. Whether that conversion is purchase, lead gen, whatever it is, that's kind of what matters. So ultimately like sending traffic to the advertiser I think is what matters most.

Got it. Now, getting into some of the ad networks and tools that are out there to help you monetize, you've touched on a couple. But what are your thoughts on the Beehive ad network that they have implemented into their esp?

Yeah, it's interesting. I think Tyler spends a lot of time going at Nathan over at Kit when in a lot of ways the they're not as comparable as Beehive is to like a substack. Right. And I think Beehive is kind of like the anti substack on that front. Monetization upfront monetization through sponsorships. But the data they release on that network, the average ad rates, the scale, the placements, it's great. If you don't have a large newsletter or an ad sales team, it could probably, I think they, they view it as a kind of a retention tool. Right. Hey, it's paying for my monthly Beehive subscription. Some brands might get a little bit more scale out of it than that, but at that level it works well. I think.

Yeah. I think long term, as it grows and they mature and they get larger and larger publishers or people growing their newsletters. You know, it's also the buying power. You would think that they have leverage to distribute across a bunch of, you know, the channel of all their newsletters for the bigger buyers. That's the hard thing for some people to get bigger brands. Right. They don't have big enough audience if you don't have a couple million, they might not be interested. This is more like, I guess the consumer side. B2B is a lot smaller, a lot nichier. But for consumer brands, they're, they're not interested on sending some for like 50,000 people.

Well, I think that's also like a little bit of a trap with any ad network, right? It's, it's adverse election. The, the brands that can't like the publishers that can't monetize directly or that struggle to monetize directly. And I mean I talk to a lot of these publishers through the dinners and through who sponsor stuff. You know, I can't tell you how many times somebody says like oh I, I wish I could just plug and play for, for revenue. And it always gets me a little heated because there is no plug and play for revenue. Right. It's like a full concerted effort like on so many different fronts. So when you're looking at ad networks at scale and I want to scoop up a bunch of 10k, 50k audiences that have difficulty monetizing, there's a few struggles. I think one for the sponsor of Voice, as I said earlier, one of the things that's kind of special about newsletter sponsorship is that Voice people read a newsletter. The voice of the publisher is really important here. So lending that voice to the sponsor, I think at scale gets a little bit more difficult across and again even consumer, I think it's difficult. And then also performance across, across that big of a scale, right. Like across that wide of a net. What does my performance look like or could I get these people directly or someplace else.

Yeah, I can see that issue. I mean you see it all the time. Just. Well, for a couple of things. One, with their ad network you can't change the copy, right? So it's in there. Whatever the ad is. It is. And then when you're looking at, you know, the big problem over the years, especially in the affiliate space, is all the fingerprinting, right? All the ad copy and everything's getting fingerprinted. So that could cause issues deliverability wise. So if they're sending it out to you, knowing different newsletters in their ecosystem, I could see that possibly causing some issues. I do see what people like 6am City, Brian Heffy over there or like the Flyover for example, how they're expanding their advertisers. They want to see more subscribers if they want to keep on scaling and stuff. But it's still the same voice, right? Flyover, they have state level ones but it's still their voice represent states but. And they have a national brand but they can kind of use that to increase the, the distribution for them. The same thing with 6am city and all their local sites, you know it's. They're all similar and they keep their voice pretty similar. So they're able to scale that way.

Yeah, yeah. Voices voice definitely matters a lot for scale. Yeah.

What about the types of tools and networks like well put that that have gone to the space.

Yeah. Again a lot of when we were building out who sponsors stuff, a lot of people would push us towards an ad network. They would say, you know, what about like a two sided marketplace? And we were very intentional about not building out a two sided marketplace. Never for a bunch of reasons. One, we never would have been able to scale revenue the way we did at the ladders without owning all of that inventory. The ability to spin up new ad products, make goods, just so many things dealing directly, I could carve out different audiences. With ad networks you can't do any of that really. Right. I think a well put or a paved or those types of tools they have utility. Again for brands that want to use that as backfill I think is always good. I had several ad networks as backfill at ladders that you could rotate in and out depending on the need, the send whatever it is. And then smaller brands that are just beginning to test out sponsorships to kind of see what their audience in the consumer space to see what type of, what type of advertisers their audience resonates with and what type of traffic they're sending to these advertisers. So again like kind of that resonance piece. Yeah, just testing out if advertising is like a good, a good sponsorship model for them. Cool.

I was going to ask you about what factors should you consider before joining a network for sound direct, but I think you've been kind of hammering that.

Yeah, I mean I'm a big fan of dealing directly versus ad networks. You know generally like any kind of agency or ad network they have their utility in place but they're not always a necessary middleman. So when scaling revenue there's, there's a lot of different tools you have to use and figure out. But ultimately the brands that, that are going to win the most are the brands that are like own their own revenue the most.

When, when people are trying to price their newsletters and their inventory, their products, what's the best method to use? Is it a flat rate cpm, cpc, cpa? Well obviously cpa. I Mean, that's more affiliate. That's, that's always a tough one. But what's the best way you, you think?

Yeah, so obviously we always want flat fee. My take on this is that. And I'll get to like how we could figure out a starting point for that flat fee, like where it should be, where it'll fall in line with the other like pricing, pricing options. The reason I like flat fee is purely like risk assumption. I think any kind of pure affiliate or commission based sponsorship without any sort of like guaranteed amount is backwards. Risk assumption. Right. If you started a newsletter, you put money, sweat equity, there's a lot into building and scaling that audience. And I don't necessarily think advertisers should just get to access that for free. Right. So that's why I'm kind of a fan of flat fee. I think it's like a more fair pricing model for brands and I think that's a good counter to the whole, oh well, you know, if it performs on an affiliate basis then we could test out something else later. Well, you built the audience already, right? So there was that work already done. One of the ways to get to flat feed, like where you should start at, right. For a consumer brand, most advertisers are, as I explained earlier, I'll explain my audience, my opens, my clickthroughs, my anticipated clickthroughs and then they'll take a look at that and say like, okay, based on this audience demographic and these clickthroughs and this traffic, this is our anticipated conversion, whatever that KPI is. Right. As an ad seller you should be having these conversations like you should be well aware of what those KPIs are and what they're trying to, what they're trying to achieve through the sponsorship. So a good way to determine what that flat fee should be is to price off of the amount of traffic you're sending to the advertiser. So I know for like most low level like CPG consumer brands, like some kind of like E Comm watch brand or something like that, they're going to be looking to run these campaigns somewhere between one and maybe $4 on a cost per click basis. Right. So you probably want to take your anticipated or actual ad click through numbers. So I know if I'm sending a thousand individuals in traffic. Okay, cool. Maybe I want to present this flat fee as 3k right. And then bundle and discount off of there. But yeah, cool.

So just to, just to the people that aren't, you know, they're more newbies and in the ad monetization space, when you're talking, when we're talking about click through rates and, and stuff for the advertiser, are you talking about the overall click through rate of the newsletter or per ad spot? I think I'm confused about that because they'll think like, oh my click through rates, you know, three and a half percent but then their ad spots like a half a percent.

No, I mean I use click to opens on the ad, like on the ad assets right now. That's not to say like when I was at Ladders. The overall click through rate on the newsletter could help paint a picture of how engaged your audience is with your content. But for the advertiser, the only one that, the only thing that matters really is like that ad click through or click to open, right?

Yeah. If you give them, if you give them the overall click the rate, they're, they're doing their projections like we were saying on 10,000 clicks, not a thousand. So how should these newer newsletters or smaller, smaller brands pitch a sponsor? You know, if they have a small list size but have, you know, really good engagement?

Yeah. So it depends on vertical. Again, like I think in B2B like the key is niching down. There's a lot of really, really strong B2B sponsors in the newsletter space. We see growth every day. We see a lot of B2B sponsors entering the space. So niching down and being specific about your audience and what they're interested in on the consumer front, you know, if you have highly engaged small audience, again, it's finding like that, kind of like that magic mix of like what is important to that audience. Right. And what can they, what can the sponsor, how can the sponsor access that audience through you in a way that they can't otherwise in other places?

Got it. You've mentioned of bundling ads in your, in your inventory a few times. Can you give advice on how to bundle the ad units frequency, how many times going out or how does that look?

Yeah, so when I started at the letters, like I wanted to fill inventory immediately and we did. And part of it was like through just testing and bundling. One of the reasons you want to bundle is because, I mean there's many reasons. One of which is one run isn't a test of anything. It could be a bad deliverability day, it could be a bad open day. Just an offsend sponsor wasn't sticky enough. You don't have, you only have one shot at sponsor copy. Right. I mean you could ab, but you're still only getting one shot at each individual with that copy. So I think that's why I always encourage minimum like a 3, 3 run by to start and then pacing. You know, it depends on how like how many times you're sending. If you're a daily newsletter, the way I always thought of it is if you're sending, I mean at Ladders we had seven days of inventory on just the daily product. Nowadays a lot of, a lot of pubs will have like five days of inventory, right. Monday through Friday. One way to look at that and filling that calendar is to say okay, I have weekly sponsors, I have biweekly sponsors, I have monthly sponsors. So you kind of want to test that frequency. And so there are brands you could run once a week without seeing any fatigue on the performance for that that sponsor. Right. The only way to find that out is to test. Right. So maybe I want to run you know, one today, the 20th and then one like next Wednesday. Right. And then give away a week to breathe, test some different ad copy, run another one and then take a look at all that performance. So it's always to the publisher's advantage and the sponsors advantage to, to do these bundled or you know, several run buys. One of the ways to like push an advertiser towards that is to discount. It's always better for you as well because that's how you get your inventory fill. Figure out what sponsors are working, figure out the frequency and that's how you get to your quarterly deals or your six month deals with sponsors. So just heavily discount those first, those first bundled sends and the sponsorships.

When you're, when you're doing, are you, are you more the philosophy of like one spot feature sponsored for the the entire newsletter or having multiple sponsors throughout a newsletter, different placements on a newsletter. Like where, where do you lie?

Yeah. So I'm kind of old school. I'm like like do the basics well first. Especially if like new like people that are starting out in the newsletter space are starting out in their monetization journey or newsletter journey here. Do the basics well first. Like if you can't fill daily inventory in a primary logo sponsorship slot, we don't have to think about additional inventory. Right. Or creating new ad products or, or more than that. So do the basics first. Well logo sponsorships. Simple works well logo up top second or third piece of native content. Hero image if you know your newsletter has that. If not just you know, copy again like it seems native your click throughs 1440 does a ton a ton, a ton a Ton of a B testing on all of this stuff, down to how many and they could all click through to the same landing page. But like, where are we putting these link outs? How many are we putting? How many placements is this sponsor going to appear in the newsletter? But yeah, generally I think do the logo sponsorships first, fill your inventory and then start thinking of additional ad inventory. And that doesn't always necessarily mean more ad inventory on your primary newsletter. You could always spin up an additional product with sponsors already in mind. We did a lot of that at Ladders.

Got it. Did you guys ever spin up a new newsletter or. Because Sponsor's request.

Yeah. So. And Ryan was great. I knew we'd go into business together pretty quickly because for an editorial guy, he was like very revenue focused and he like, he just got it. Once I was able to sell, he would just blow up my, my slack at all times with just like, hey man, you should see if for example, like it was Morning Brew was working with us and he was like, oh, like tomorrow's International Coffee Day or something. Right. Like, why don't we spin up a newsletter on coffee and then like we'll see if Morning Brew wants to sponsor it as like start your day with Morning Brew. And then it's all like these coffee and career workplace like adjacent content. Right. So I just called them and right on the phone was like, yeah, let's do that. So did it. Right. That's how we spun up. We had dedicated email products and our dedicated email products were selling at like 10x my daily rates. Right. So. But again, wouldn't have been able to do all that if I didn't fill all the inventory on the daily first and see the sponsors and also own those relationships with the sponsors. You don't necessarily get to do that through ad networks. Awesome.

Let's change gears here and let's talk about the, the events. Is that our events company and what's going on over there? What, what inspired you? I think you might have touched this in the beginning, but what inspired you to start these live events?

Yeah, so Ryan and I were speaking at a conference in 2022, still kind of COVID era. And it was a very large conference and there wasn't a soul there that I could talk shop with. Really like just newsletter business kind of revenue conversation, a few contacts that I knew, but I didn't meet anybody new that was really like they weren't talking about newsletters from like a revenue driven perspective at all. So we, out of frustration realize there is a need for this, the newsletter space is mature enough. Like there was no morning brew representation, no skim representation. And this was a large online news conference. So we reached out to Dan Oshinsky of Inbox Collective and we reached out to Louis over at Sparkloop. Louis actually sponsored our first dine and deliver dinner. We did it in New York and about 20, 26 people. I think the first one was November of 22. And the way the dinner series works is we just get between 20 and 30 operators in a room for one off the record private curated discussion. They're a sponsored product, but they work really well just for like industry discussion. They're not like ad sale pitches at all. It's pure industry discussion. You get to hear a lot of really great takes, a lot of great vulnerabilities and you know, it being off the record I think is really cool too. And that had scaled. People apply to attend that. We launched that with the intention like the dinners were our full intention was to get to conference after a year and a half of dinners. That list was somewhere around 700 inbound applicants. I mean now that's in the thousands. And we knew we had enough of an audience to go go to market with for the newsletter conference.

Are those dinner series free to attend? The sponsor covers the cost of the dinner for everyone.

Yep, they're sponsored. Like this year we have Omitas, our title sponsor and then we have additional supporting sponsorship with like might have six, six to eight supporting sponsors on it this year as well.

Cool. What role do you see the in person connection playing for the newsletter people that are going to these conferences?

Yeah, I'd like to say Ryan and I were early ish in this newsletter kind of swing. Right. Like the 2018-2020 kind of newsletter push. And I like to think we're kind of early on the in person kind of thing as well. I think part of it was Covid, but not all of it also is as we enter this new AI era on so many different fronts, I think there's a real want for in person connections, especially in the B2B space. People were happy. I mean the first newsletter conference we oversold. We had over 400 attendees. It was people were happy to be out networking. And same with the dinners. We'll frequently get messages of like, hey, I'm so glad I went because I got to meet so and so who now I talk to on a regular basis. So I think that we're still kind of early in this wave of like in person events. And I also think events are going to be a huge revenue stream for a lot of media companies as they are becoming now and as time goes on.

Yeah, they're great. I've been to the, I went to the first two, so I definitely enjoy them and the, the dinner beforehand. Going to the fact of scaling and sustaining your ad revenue for the newsletter publishers. How do the top tier newsletters keep monetization strong without sacrificing the health or quality of their list, not burning them out.

Yeah. So again, you mean like as far as like my, my stable of advertisers, like how do I get them to, to run over time?

Well, I guess, I guess there's a couple of things like how to not be too ad heavy to turn off your, your subscribers and then how to, you know, not burn out the advertiser. You're talking about bundles, frequencies, all that stuff like you don't want, you don't want the. Obviously we can do change of creatives and stuff like that to mix it up, but you don't get that, you know, burnout or like where you don't see the ads anymore. Just blind to whatever because you're so used to that spot being there and you're like, what I'm scroll right by.

Yeah. So like I refer to that as like fatigue, like how to delay fatigue. So on the. I'll start with the audience side of it first one, one of the things that we saw, especially when we were doing like the outside sales stuff in 2020 for a ton of different brands, a lot of these brands had different sub tiers that they would like, subscription tiers that they were beginning. And something that became a little bit of a pattern I thought was not great was hey, pay dollar a month and you get the ad free version. Right. And I think the problem there is that as I've said a few times, like newsletter sponsorship, the way it works is like that voice. And if you know your audience and like your audience, you are, it's your opportunity to platform a sponsorship or something that makes sense to them that could. If it's a B2B in a B2B case, like it makes a ton of sense. Right? Like these are tools that these people are going to be using as part of their jobs. Slam dunk. Nobody's going to be upset about that. And personally, maybe because I'm a fan of kind of advertising generally, I mean media, but especially advertising. Like I like when I get a targeted ad that makes sense, somebody's introducing me to something that I might want. So I think like the whole ad free audience burn is a bit over hyped. With that said, obviously, yeah, there are brands that have, you know, if I have a newsletter that's like a consumer facing newsletter and I'm just filling it with 100 different affiliate placements that have no real tie into my audience. There's no real strong angle. It's, it's off target. Right. That's where kind of where that misalignment happens is where the friction and the fatigue can happen there on the audience side of things. So the more aligned you are with your content, your advertisers and your audience, the audience really doesn't have a ton to complain about there. As far as sponsorship scans.

Yeah, no, I agree. I think, I think the biggest issue is the newsletter operator want for revenue and just taking anything they get and not being patient and selective with what they're providing. And as soon as you put up some spammy garbage on there and you know, some direct response, call it the foot with the big ward on it or something, that could really do damage to your brand.

So yeah, Ryan and I, so at Ladder is like my main. When I had started there, he was like, just make it so I don't have to put in these live intent like foot fungus ads. Right. Like those little banner kind of things exactly as you described. And then fatigue on the other side of it is trial and error. Right. And just never being complacent with your current stable of advertisers. You always do have to be prospecting for more advertisers and constantly trying to fill revenue. One of the ways to do that is getting out ahead of it. Right. Like starting, you know, where you start booking. If I'm starting from zero, I want to fill the month as quickly as possible. And then I want to start thinking of like, okay, I want to start filling multiple months. I want to start filling a quarter at a time and then I want to be six months ahead of it. It's kind of like the real goal. If you get a year out ahead. Amazing. I've never been there, but. Yeah.

So outside of, of focusing on, on filling up your, your primary sponsorship and making that your primary goal and your primary revenue stream, are there any other signals that you would use to show that you're ready to scale up or you know, ad opportunities, units, whatever you, you know.

Yeah, I mean once you're out of inventory. Right. Once all my inventory is full, I know there's a few options you could push rates up, but you don't ever want to like price yourself out of market. That and raising rates doesn't always make sense. Right. It could be running as it should be. So I think you have the option to either raise your rates, which you should be doing, but not to extremes to cover the revenue gaps that could be filled with either additional inventory, whether that's a secondary placement, tertiary placements, or new newsletters specifically designed to drive sponsorship revenue.

So as far as this is actually a good thing to ask as far as raising rates and stuff for people, how often should the publisher be looking to increase their rates? Like, look at it like, obviously audience size goes from a hundred thousand to two hundred thousand. I mean you have double the audience, so you better be raising your rates. And then with that being said, how, how far in advance are you comfortable pre selling to knowing that you do have this growth and if you, you know, say you book it, you're trying to ramp up double your size better than a year. If you're booking a whole year in advance, knowing that you're going to be at whatever volume towards end of year, halfway through the year. But you sold stuff in the beginning for the whole year. How, how do you take all that into account for, for selling?

Yeah. So I think there are brands that I've sold for that would send me monthly media kits with pricing increases. And it was, it's a lot, right. Like to deal with, to talk to a sponsor and have them like, wait, this is what it was like two weeks ago, man. Like, come on. So I'm, I'm opposed to like that, that kind of like monthly raises, even quarterly to me is a bit off. Look, if you're going from 100k to 200k in that short of a span of time and maintaining your open rates and engagement, you have some, probably some money and muscle behind that build. Right. If you're doing that in a matter of weeks or just like a month or two.

Yep.

So if that's the case, again, I'm probably looking for like stability and inventory fill to me are like essential. So I want to make sure my inventory is filled with sponsors. If you are in that rapid of a growth phase and you know you're in that rapid of a growth phase, I wouldn't go beyond selling quarterly. But look, if somebody came to me for a year sponsorship when I'm at 4k audience and we agree on rate, and then all of a sudden at the end of that year I'm at 500k, like they were an early adopter to this. So I don't see that as a negative. And you could grow with those sponsors too. Right. But generally. Yeah.

What's your thought on like pre buys on, on future growth, I believe. Who's I talking to? Ryan Heffey. I think he's, he's been able to in the past, I think launch into new markets, but with like sponsors built in already and they know the growth plan of what's happening and they're going and they're. And they do it and they logic that. But they have some pre built in sponsors which helps them pay for, for the subscriber acquisition in that market to go. And they're getting the, you know, they're getting all the sponsorships spots already lined up. What do you think? A pet strategy?

Yeah, I mean that works. One, he has a lot of like, Ryan has a lot of data like they've done this in so many markets. So at this point he kind of knows like the anticipated growth for each market. And they're also testing markets like aggressively before launching in a market. So they're testing all that out beforehand. But in a lot of ways that's not too different from spinning up a new ad product and telling a sponsor to take a gamble on it with you. It comes down to owning those relationships and having really good relationships.

So there's been a lot of hype here. I think we touched base earlier, not on this, on this podcast, but the whole headline that came out about Daniela Pearson and new set and her about, you know, selling her advertising, saying her list is one size but really only sending to a certain size. I come more focused on the deliverability aspect of email. So I understand what list size are, what sending sizes are and all this stuff, but it's been getting out there quite a bit in the headlines. What's your, what's your thoughts on that whole situation?

Yeah, it's funny when I guess it was the two pieces that dropped Insider and Forbes dropped one and now there's probably a few more. None of it was surprising to me, to be honest. Like, I think a lot of people that kind of knew the news that and like the revenue numbers they would boast seemed a little fishy given like what you would see on, I don't know, like what you would anticipate that skill actually was it's never great to overstate your audience size. Right. Like that's not to anybody's advantage. I think it's important to have integrity when dealing with sponsors for a lot of reasons because it just doesn't necessarily like it's not you end up burning yourself in the end, right. If I say, oh, I'm sending to over a million subs, 300k of which are like that's my actual audience size. Like, you know, I, I would like to see like what, what, what you present is like what was presented as like your click to opens up against that over a million audience. Right? Or was it up against the 300k that you're sending to, you know, at the ladders I started there, my audience size was over 4 million. Like our sending, like we were sending to that many, but open rates were low. You know, this was like anywhere from like 14 to 18% on opens. Eventually we reduced those, that list size and got those opens up there. It worked though, because I was pretty upfront about it and the way that that audience was cycled through and the way we were sending, it could be unique openers any day of the week. Just the way that audience was built in the news ads case a little bit different. Sort of like a bad faith argument there of like, oh well, you know, we have over a million subs, but really only 300k subs.

Yeah, I mean when you're, when you're selling a floppy or you know, CPM base, it's definitely a bit, it's not, not, definitely not something you want to do because you got a line. But that comes back to like, are they, are they, are they re buying? Are they booking again? Because if it's not performing, I don't know enough about the advertisers and what they had going on. I'm assuming a lot of it was branded stuff because of their exposure that they had. I don't know if they were doing a lot more brands that they didn't know the performance necessarily on it. I, I don't know, was it the normal direct response people and just wasn't backing out and they just kept on getting new advertisements. I can't imagine you keep on advertising on something that such a large list size and you're not getting enough traction from it.

You know, I mean, I remember, I mean I thought the news that was like largely sort of, it was like women's culture interest, right. And like fashion. So I thought it was a lot of like that type of doctor stuff. So maybe, you know, maybe they don't notice. Maybe it's just like low conversions and that's where it happens. But yeah, eventually it's gotta catch up to you. If I'm paying for a million and I'm only seeing, you know, click throughs or site traffic from an audience that's significantly less than that. Right. If the numbers don't add up, then yeah, it's got to catch up to you.

And then, I mean, this doesn't necessarily help, especially in the mainstream. Does the newsletter space have a trust problem with their inventory?

I don't think so. I mean, look, there are bad actors all over the place. I don't know. I think generally the brands, like reputable scaled brands, a lot of what Ryan and I deal with are more legacy media institutions and then like established, like already established and scaled independent media brands. So for them, you know, that's not really an issue. Maybe they scaled to that point where, you know, where they were working with advertisers from, from the beginning till now and it's not really an issue. Maybe on some of the ad networks I could see that possibly with some like, kind of bot stuff, but again, easy to catch and easy to fix.

Are you seeing. I guess it's probably easier now.

I know.

I mean, back in the day, which I think caused such a lag in the newsletter space was all the local newsletters, newspapers and newspapers in general selling the online and the newsletter as like a freebie on the advertising to the print, which for other advertisers I'm sure, especially like for local newsletter brands, they, they probably have a bigger challenge getting advertisers now. Well, it might be easier now than it was before, but I know in the beginning it was super hard because they're just like, what are you talking about? I get to free thing on the Palm Beach Post or you know, Sun Sentinel. Do you think we've gotten past that or is that still kind of a thing over our shoulder looking, looking around.

So that conference that I spoke about, that was like the reason, sort of that spark that we started the events. Wall Street Journal gave a panel about like their newsletter program and they, they did a, it was a pretty, a pretty deep dive. But after that panel, I kind of, I went up to them and I started a discussion kind of around that, right? Like, okay, so what metrics matter on X? Like this one doesn't drive revenue. This doesn't do this. Like, you know, Alex Lieberman started Morning Brew in a college dorm room and got a multimillion dollar exit. Right? Like, so if I took any one of those Wall Street Journal audiences in like a 20k clip, and then I started building a media company around just that 20k audience, it would follow that I'd have a pretty valuable media company. And I think for the legacy brands, the Way that they viewed it was like, okay, there's more than just revenue on the newsletter builds. They fit into the overall media infrastructure there in a way that's a little bit different from our world of like pure newsletter first kind of brands. With that said, now you'll see legacy brands and some of which Brian and I do some consulting for will come to us and say like, hey, we need to figure out how to do this now. Right? Like Morning Brew scam. Like all these brands that figured out newsletter and drove real media brands, now they're multimedia brands. Right. Morning Brew has an events business that's scaling really well all the B2B verticals and that started as the skim for finance bros. Right. So now the legacy brands are realizing like, oh, we have to catch up on newsletter, like how do we get there? So I think now we are getting to an era where newsletter will see its. Sounds weird to say like it's rightful place in like revenue strategies. But yeah, I think there was a lot of reasons it was. And then just a side note, like for anybody that has like any multimedia stuff and newsletters are part of your offerings, just don't ever like always apply a rate to it. Don't, don't ever offer anything free added value. It just diminishes its, its value immediately.

What excites you, excites you most about where newsletter monetization is heading?

Yeah, generally I think for newsletters I'm excited as these brands like as newsletter first brands begin to become more than just newsletter brands I think is really exciting. And how newsletters fit into creator builds is like adjacent that as well. I think on the revenue front diversification is like what's really exciting outside of just sponsorships obviously. Whose sponsor stuff is big on sponsorships. You should be pursuing revenue outside of just pure sponsorships stuff like events webinars on again on the B2B front, but on the consumer front, events could drive a lot. Yeah. So I'm excited of like the diversification and the continued maturity of the space. We've come a long way from 2018 till now.

What's your thoughts on the subscription model?

Yeah, also solid, right? Like it's. I like sponsorship models because I like the idea of being able to educate people or like give them the content they want. Subscription models work really well for a lot of the B2B pubs and some consumer pubs. I subscribe to a few creators that I'll follow for like a few philosophy blogs or. And then obviously I'm subscribed to on the B2B side like a media operator, Jacob Donnelly's build is phenomenal. But again like if you look at Amo Jacob Donnelly's build like it's subscriptions, sponsorships, webinars, events. So yeah.

And do you see AI impacting sponsorships or advertising in the future?

Yeah. There's so many ways that AI has an impact on our space. I think1 is AI search results could impact not publishers1 but also probably has some impact on sponsors as well. So again I think just being really clear about your audience and I think as it's going to be really important to know your audience too. Which is another side to like the in person part of it and why that's great. The better you know your audience, the better you could pitch to an advertiser. And then as far as what could be utilized by AI or the benefits to AI there probably for some like kind of a B testing, copy testing like maybe diving through some audience segments. But yeah.

Cool. I'm going to go through a few rapid fire questions here, see what you, what you got here. What's the most overhyped monetization tool?

Most overhyped monetization tool. Any kind of plug and play network is definitely like pure plug and play is definitely override.

What's the most underrated monetization tactic?

Yeah, so grit. Right. Like just that the kind of like huge effort, like if there's a sponsor you think is a really good fit for your newsletter and you have a really good angle for it, like being kind of relentless at getting at that person and you should know like everything about that, that branded campaign. But like really, really that sort of, you know, just keep knocking on doors mentality.

Got it. Favorite niche newsletter. Monetizing smartly.

I don't know. I mean I would say I don't know if I could call like amo niche. I think he, I like what he does with like the monetization. Like his subscription model is like really, really cool with the, you know, the slack those kind of models. On the indie news front, Monoos is really cool. I think he's doing a lot of cool things there too.

And right now what's the most aggressive sponsor category?

B2B AI for sure. They're coming to maturity now. Like these brands finally have products that they could that make a lot of sense for a lot of different B2B.

Use cases and outside of a MO because you've said him a couple times. What newsletter operator should everyone be watching?

Newsletter operator. Everybody should be watching. Well, email intelligence. Everybody should subscribe to, which is right in my newsletter. Also, Dan Oshinsky always will always plug Dan when I get a chance to plug Dan. And obviously Jacob, if you're not subscribed to amo, I couldn't recommend that one enough.

Well, I think that was pretty good shot. I think we went over a lot of stuff. I think a lot of good, useful takeaways and insights on the monetization front within newsletters and what's happening, happening out there. Where can people go to find sponsors and sign up for your events? You know, give your, your little stick there.

Yeah. So who sponsors Stuff is just who sponsors stuff.com for our newsletter events? We have, we do have. I mean, I guess we own the domain so I can kind of reveal we have like a media enthusiast domain. We're probably going to build around for a lot of our events. So we have the business of local coming up in Salt Lake October 19th through 21st. That's going to be about driving revenue in local media builds. I think the timing is really great for that and the need is really great for that. And then the newsletter conference next year will be May 8th again at the Time center in New York City.

Awesome. Well, if you're looking for a deliverability speaker at that conference, let me know. I think, I think that's one thing that's missing from these newsletter conferences is a little insight into deliverability for the newbies. And even the experts, they don't know what they're doing halftime either.

Yeah, that whole space is way over my head. I. It's like voodoo adjacent to me, you know, like, do I have like the rituals before ascending? Deliverability is way more complex than my brain can handle. So yeah, we'll reach out.

Jesse, thanks for coming on. Appreciate the talk. Hope it was, you know, good for you too. And we'll see you soon.

Excellent. Thanks so much for the time, Chris.

Hey, I hope you enjoyed that episode of Audience for Insights. If you did, go ahead and do me favor a solid. Click the subscribe button right around here. You can also subscribe to the newsletter. I have a link down in the description below. Now we have a lot of amazing guests lined up, but until then, keep sending smart.