Hi there and welcome to Scale. I’m your host, Stewart Ritchie, the founder and lead developer at Power by Coffee, a web and software development company working with media brands using open source to solve problems. Scale is a podcast about media and about content heavy businesses and how technology impacts them and how they are impacted by technology. Today we are really excited to have Justin Duke, the founder of Buttondown, a really excellent, easy to use, super simplified email service. I want to kind of talk to us about advertising within email newsletters, a topic we’ve mentioned a few times in previous episodes. So, justin, thank you very much for joining us today. I’d love to start with your own background, because it’s pretty remarkable From my perspective. There’s some great places on there, so tell us about yourself, tell us how you go, where you are. It’s a point of starting starting Buttondown.

Of course and thank you for having me, Stewart I took what in retrospect was, i think, a bit of a circuitous path to sort of the tech industry. I was an English lit major in college and quickly realized, as did many of my classmates, that being an English lit major was not exactly a short circuit track to career success. And I had a couple of random internships in like advertising and copywriting realized that wasn’t for me and wanted to start working in computer science.

Yeah, that’s every developer I find at some point code is using something that goes I can build something better than this, and it is almost invariably a project management tool or a CRM of some description. It’s very unusual to me that you have turned around into I’m going to build my own email service provider and email editor. That is out of left field, although I suppose here have been a few kind of more independent and kind of lightweight email headers and email provider tools. Something like tiny letter jumps to mind immediately. It’s kind of a very early, early player in this space. Yeah, it’s. It’s just a really interesting space to be.

Of course, and you mentioned tiny letter, which fun fact the code name for buttondown. before I really launched it was tiny better, because that’s the tool I was using that I was getting very frustrated with of the feature set of tiny letter to me was perfect of you have emails, you have subscribers, you have like form tags, that’s.

Yeah, yeah, that’s awesome. So kind of very much that I kind of think of the moment is like the whole automation crowd, the folks are very able to set up stuff like if they’ve got an iPhone or built into the max system.

Yeah, the biggest change from my perception over the last, say, three to four years is and I think you hit the nail on the head like everyone is realizing that the idea of like, owning your audience or owning an email list is not like this, this niche thing that you might want to do if you’re, like, say, a journalist that’s hopping from publication to publication, or you’re a consultant trying to have an audience to sell. But, like with the increasingly fractal nature of a lot of these social networks and I don’t know about you, but I feel like over the last three years, my, the folks who I chat with, went from basically just Twitter and maybe like a slack or two, to like Twitter and mastodon and blue sky and discord and slack and WhatsApp and like it’s. It’s increasingly difficult to like have one single repository of like I want to share what I’m up to with folks And I think email is is perfectly tailor made for that, and the fact that the median folk trying to do that is no longer, as you say, like a tech blogger, but it’s just like anyone who wants to have a long term relationship with their audience, means that the a lot of the things that were kind of first and foremost in my mind when I was building buttondown, say in the early days of 2018, 2019, which was like how does this integrate really well with, like static sites? how does this integrate with with Zapier, with if this and that those things are still important. But there’s also a huge ground swell of folks who are just trying to do like the base case of hey, i don’t know if, like half of my Twitter audience is going to go away tomorrow. I need to be able to contact them so I can share with them the new pieces that I’ve written, or share with them like new consulting opportunities I’ve had.

Yeah, absolutely Every night. Again, I’m struck at how crazy it is that email exists, that is just this open, massive network of standards that people can just send messages to each other, and certainly open for abuse, but that it works like. That’s crazy to me, in a world where everything is currently a walled garden and you have to fight to get your data back out of us, that this thing just kind of works still. There’s been 100 email killing apps over the years. I mean that was Slack’s big thing Over the stars. Like never have another work email. And like you will never kill email. It is too just barely useful, like it just barely works enough that it kind of will never, ever go away. It’s the same as to get very nerdy. The DNS system I’m like how on earth does this exist And it was not ruined by anyway? that’s that side of the beyond what we’re going here. So one of the kind of with not the downfall of Twitter, but kind of how we’re changing and seeing like the media landscape change and more and more kind of independent producers kind of coming along, email being so important. We’re not even just for media companies but like and producers and writers, but for everyone.

Yeah, and I think, at a high level. One of the things that I find sort of refreshing and interesting about sponsorships and advertising in the email newsletter space is that because of how jinky a lot of email sending and a lot of client experience is, you actually, i think, obviate a lot of the problems that personally I find pretty gross and odious about the general advertising landscape of like I think there’s very little that’s worse than having the army of tracking pixels follow you from every single top 100, all that’s a site that there is like that’s just not really. I’m kind of like the old bearded nerd myself, like that’s not my vision for what like a glorious web is. And I think really what newsletter advertising reminds me of in many respects is the world of podcast advertising. I think there’s a lot of lessons that you can take from podcast maturation over the past say, 10 to 15 years and how it applies to newsletter advertising, because there is more room for kind of experimentation as a publisher.

Awesome And I imagine all the CM rules apply to in email advertising that, due to more general advertising on the internet, if it’s an integrated piece into the content, it kind of has to be clearly demarcated This is an advert or this is sponsored content, this is referral content, et cetera.

Exactly. Yeah, there’s, and I think of anything. this isn’t true of all clients at this point, but Gmail is sort of most famous for having the auto categorization of. This goes into emotions. This goes into updates. I’ve seen a lot of newsletters that I’ve worked with, like have the, and it’s kind of interesting because it’s frustrating from the newsletter center standpoint but it’s great from all other parties of. Like you’re sending out a regular email that lands directly in clients inbox in the primary tab, and then if you have a sponsored takeover email, that’s gonna end up in promotions And like that might be a little frustrating, but I think, if you take a step back, that’s what the reader wants. Like that is the correct thing to do, and the fact that email infrastructure, for all its warts, has a lot of stuff set up that you don’t have to discover from first principles like highlighting specific things as promotions, makes it a much more useful path.

Absolutely. I just think it’s interesting, as well as we record this it’s just been WWDC and kind of one of the things a nice or user privacy kind of reasons that Apple is going to start actively removing and stripping tracking parameters from URLs that are sent through iMessage, adding emails that are opened with a Apple Mail, both on the Mac and, i believe, on iOS And, i think, finally, on any link you click if you are within a private browsing mode. So I just wonder then if this is a world that is gonna get more and more, gonna have to kind of mature rapidly to move beyond to just having an affiliate code as part of the URL, as part of like a query. Far it’s gonna end up being like defined landing pages for these campaigns that maybe are something that was gonna get missed or, like you say, just communicating it in like you would on podcasts or on a YouTube video or so like use code X, y and Z to check out. Are there, is this a very manual process for publishers or are there kind of tools and things that automate this? I mean to bring it back to your podcast analogy.

it’s definitely similar to where podcasts were, i’d say, let’s say, five years ago, where you have the entire landscape that you mentioned all being represented like a huge amount of newsletter ads, especially for, for what I would call like the long tail of newsletters, right like, say, 3000 to 50,000 subscribers. They can self-scused, they’re. They’re making relatively good money as a side project, but it’s usually one or maybe one to three folks running it. It is not the mandate of a larger team. Most of those folks will be Handling the sales, handling the creative insertion, all those things themselves, maybe using a two-sided marketplace like paved or post-it backs to just connect with potential sponsors, but then the all of the administrative around it. They still kind of have to handle themselves really, really large operations that have a pretty sophisticated setup. We’ll have a lot of automations.

Yeah, absolutely to. You worry at all about Google’s presence in this space, as both a provider of. I Have a very large, very well used email platform and a huge amount of advertising.

Worry isn’t quite the right word.

Yeah, absolutely So. That email, that’s the dynamic emails that you were able to produce within Google mail. So just if I saw a really good example of a few weeks back and it’s completely Just dropped out of my head If anyone who hasn’t seen, it is when you could like send things like a Google Sheets link to someone and if they were using in Google and they had the correct access permissions, they would get a preview of that Sheet, for example, within the email and they’ll have to load sheets and so there’s like a small subset of blessed components from Google mail that you could use to kind of have these richer email Experiences. That’s this. So that’s kind of like we’re on comfort. I’m as well as like are they gonna leverage this for Advertising an egg? Maybe? maybe we’ll see So.

So I think it’s great, i think that’s usually what’s on the top of folks minds and it’s it’s the question I get the most, which is just like how do I get from from here to there of, hey, i have an audience of 2000 folks who, you know it’s not a super large audience, but like, i think they’re all Really well engaged in a solid niche. Like what is my first step and I think the This is very, very boring advice, but it’s extremely actionable Which is just to like king your shingle out, so to speak, and like have a tiny little, like, do a tiny little bit of Outbound sales. Say like at the bottom of your newsletter Hey, if you’re interested in sponsoring this newsletter, please contact me. And. And every time I give that piece of advice, people are like no one’s gonna do that, like I don’t think I’m gonna get any interest, i’ll try it. And then they all come back after they do and they’re like I just heard back from like seven folks And like I’m gonna set up some calls. You have to do like we were talking about earlier. You have to do a bit of manual work to start, like, if you don’t feel super comfortable with that, that’s fine, we can discuss alternatives in a second. But I think the best thing to do in terms of really Validating that sponsorship is a path for you is start to hear from your readership and the folks who are already listening and engaged with your content and Seeing because often especially for the more lucrative news fake newsletters, rather, those are people who have ideas and have a good sense of what their niche is and probably can bring some adjacencies. To give an example of, i Chatted with a tech review newsletter a couple weeks ago that does map device, apple device reviews, that kind of thing, and They sent out an email of this nature and words just like regular, regular edition And then at the bottom, if you’re interested in sponsoring this, like, please drop a line and let me know. And they heard back from a couple of their readers who Kind of do stuff in like the the third-party device ecosystem of like cases and things of that nature where it’s.

Yeah, and then if you don’t, oh sorry, go ahead.

That’s Advertising supporting the content because it is at least related exactly like I think the the worst type of advertising and this is true in email and outside of email is Something where it’s so dissonant, so jarring compared to what the content actually is of like. Alright, i’m reading about tech news for 600 words, and then there’s like an advertisement for like Soccer balls or something torture metaphor. But you get the point like the best and highest performing Advertisements are the ones that have a really really close Symmetry and marriage with the content they’re about, and so you want to attract those advertisers, and those advertisers are gonna have a really really strong Bend diagram overlap with your existing readership.

Absolutely. Yeah, yeah, sorry, i interrupted. Please continue on with you. No worries at all.

I was just gonna say, like the, there are a lot of folks who don’t feel comfortable taking that first step into doing like slightly outbound Sales to get their first few sponsors, the. The other side of this, too, is if you go to Two-second, two-second marketplaces like paved or post-a-packs, you can eliminate some of that a little bit. A lot of More mature advertisers will have what they call like pre canned or native creative, which is sort of here’s a link, here’s a sentence of copy, here’s your affiliate code. We don’t need to do any sort of back and forth. We’ll just pay you out based on the affiliate side And so you don’t really have to do a huge amount of pulling.

Yeah, i think I think that’s really one of the key points is working with the advertiser to create the piece That works for the audience, rather than the off the shelf Creative. They can just kind of be dropped in and linked up, whether that’s a specific piece of content You’re linking back to you on the primary site, or specific landing pages or things that are tailored in with whatever the broader kind of editorial calendar for that Publication kind of is. That really seems to be what would make the difference in this being a good experience for everyone. Exactly, and like to go with that. I think getting that right then means that that published that advertisers going to stick with you And it becomes very easy for them to be like, yeah, just run the same thing again. It’s not about finding new public, new advertisers for every and sponsors for every Issue that goes out. It’s building good, solid relationships with a few and having You be one of their best channels so that you can kind of up that rate over time as you can demonstrate value.

Yeah and it’s funny how much of this conversation All kind of boils down to owning and being invested in that relationship. Because you’re exactly right, like the one of the trickier parts of like just kind of being one of many newsletters in an anonymous Two-sided marketplace is you seem very, very fungible and like you don’t actually get to build that long-term relationship. There’s a newsletter who’s been on buttondown for a better part of four years. She started advertising when she had around like three, four thousand subscribers and Some of the the companies she partnered with then are still advertising on her newsletter. Four years later She’s increased the size of her readership by like a thousand percent. It’s grown 10x. But those early relationships are still paying dividends.

Yeah, it all sounds great. And then I suppose from the technical side I mean coming from more of a web background kind of with modern advertising, it’s a lot of ad tags, so, if you don’t know, it’s a whole load of like external work that you get dumped onto a page. You say like, oh, in this particular area of the page put this ad and this tricker at the page put that out. That’s not gonna work. And email delivery So how, how does that technical integration happen? How did they actually Get the ad into the email?

depends on the level of sophistication for the platform and for the publisher on both sides. I know a lot of authors who have a very like manual drinky process where it’s like that you have the styled block that says TKTKTK, and then right once they are about to send it there, they’re like all right time to do the copy paste, like get both sides to approve and like just do it completely manually. Yeah, if you’re using a platform like bundown or something, it’s a little bit more sophisticated. There’s tooling set up so that, like you can dedicate a specific like template tag in, in sort of more Developery terms, that if there’s an advertising Unit sold for that given issue, that given week, it’ll get plopped in. Otherwise it’ll just be.

Yeah, it’s good That’s going to be gone. It’s not going to you deliver that, but crucially I think that’s the one of the important things here is that actually this is a very simple thing For almost anyone who has the sophistication to be running a newsletter to actually do, depending on the creative you come up with with That sponsor. It could be an image tag that is going in that you’re wrapping in, and a link tag I don’t very certain point at the lay, or another paragraph tag with with some text, and it doesn’t have to be complicated. There’s There’s not a good technical reason, i mean, for someone to not do this. It’s, at the most basic level, very easy to get get going with this. It sounds like exactly, and it’s.

It’s one of the things that, like you, can get a more sophisticated Over time. If you want to, wouldn’t need to, but there’s not a very high bar of like. Alright, i want to. I want to include sponsoring content in my first email time, to dedicate an entire weekend to figure out how to do that. Your first few issues, when you’re still sort of Validating the thesis, so to speak. Like you can copy and paste you. You don’t have to worry too much about automation or anything like that. It’s just let’s find the right advertiser, let’s agree on the copy and on the creative whether it’s an image or a paragraph, as you said and then let’s just plop it in, and then All the fancy stuff can come later in time. I’m using.

So I mean just to kind of like recap this whole whole thing that I suppose like Create, create revenue opportunity for you and publishers, media groups, particularly smaller ones, who are just getting started with this kind of thing. If you’ve got a really engaged audience and you’re in good, lucrative niche, reach out to some of your readers, some of the people you cover, potentially even as well be like hey, we’re going to start sponsoring these would you be interested in. If you’re not comfortable with that, then there are platforms out there, but definitely better to to go for the existing audience and the kind of surrounding groups. Very simple to do technically if you’re just getting started and the real key here is just just getting started. So thought about cover up kind of How to get going with these absolutely.

I think the point that I would end on is just Not just when it comes to sponsorships, but like monetization writ large. I think the folks should feel like 30% more comfortable with experimenting than they currently do. Sometimes paid subscriptions are great, sometimes sponsorships are great, sometimes upselling to like some, like tangible artifact or skew like. I’ve chat with a lot of authors who their thing for more evergreen content is like They’ll publish ebooks every couple months. That’s just like here’s the top 10 things that I wrote in the newsletter. If you liked it and you want to support my work, like hey, 999 for this or whatever, but writing a newsletter and maintaining like an editorial calendar is serious work and it’s valuable. And if you have a readership that likes it, enough to stay engaged and keep reading what you do over time, they’ll want to support you in some way.

Absolutely, and then it was. Also, it’s worth pointing out that nothing we have said here is actually email specific, like what we have said here, because you’re looking to go to your audience, find similar things within SPS, put it in the medium you were already using and see what works and experiment. A little bit applies as equally to an email newsletter, as it does a podcast, as it does a video series on YouTube, vimeo, wherever you’re putting it, even starting to monetize your own core website, if that’s something you’ve done. These principles are kind of global and work for those very engaged, good niche kind of products and places.

Couldn’t agree more.

Cool, i’m glad. Well, justin, thank you so much for your time today. We’ve got on a while. If you want to find out more about you, more about ButtonDyne, where can they go?

Yeah, you can follow me on Twitter. I’m at jmduke, or you can just visit buttondown, which is buttondownemail.

Pretty hard to me into search for. I was looking for it earlier and I kept getting ads for shirts. There’s, yeah, that’s cool.

I was just going to say there aren’t a lot of regrets I have of the early days of building buttondown. I feel like I should have chosen a more SEO friendly name. It’s like me competing against J Crew and Poshmark to try and get the top three slot in buttondown. Always rough goings, but beyond that can’t complain.

Yeah, i understand your fear. Powered by coffee is like a weird name. It doesn’t fit into anything about what we do. It’s just a random string of words on the surface But also, with my particular accent, people don’t hear it well, they’re like what did you say? I understand that. Maybe we should have thought that further, but awesome, thank you again. It’s so much for your time. If anybody wants to connect on Justin, we’ll put those links in show notes. Show notes are on partofcoffeecouk for its last scale and that’ll link you to the most recent episode.