[upbeat music] Welcome to the Rebooting show. I'm Brian Morrissey. This week I'm joined by Adam Ryan.
Adam is the CEO of Workweek, and Adam and I both wrote, coincidentally actually, somewhat similar pieces last week about a coming inflection point in the email newsletter market.
Calling peak email is a fraught endeavor, of course. I think email is dead has been declared every year since the first email was sent in nineteen seventy-one.
But the market is clearly shifting with an astounding number of email newsletters popping up. I was told there's something like three thousand AI-related email newsletters on one platform alone.
And, and battling for attention in the information space is simply a reality. And meanwhile, AI continues to disrupt distribution channels, notably search.
Now email has always been thought of as a refuge from a lot of these distribution challenges because email is always billed as being a direct connection to your audience.
And that is true to a degree because at the end of the day, digital media, you are always downstream from some sort of technology aggregator.
And ESPs, which are increasingly controlled by the largest technology companies, are such a choke point. And Adam makes the point that nothing is forever, particularly in the media business.
And he sees AI-driven changes coming to how inboxes are managed that will undoubtedly be a bonus for those of us who are trying to s- make sense of our emails, but are also likely to be a net negative for many newsletters.
And we discuss that shift, how to manage it as a newsletter operator, and also what it takes to make the leap into being a true community business. I hope you enjoy this episode. I always enjoy talking with, with Adam.
We, we come at things from slightly different perspectives, but I think we, we mostly end up in, in a similar place. I'm always eager to hear your feedback. You can email me at bmorrissey@therebooting.com.
If you like this podcast, please leave it a, a rating and review. I always get a kick out of those. Supposedly, they help with distribution, although I'm never totally sure about that.
Of course, be sure to check out the Rebooting for my piece and I'll also link to Adam's in the show notes. [upbeat music] All right, this is a very exciting podcast. I am, I'm rejoined by Adam Ryan.
I think you were on one of my earlier podcasts. I think, I think we- I think you've been on a couple... I think we... You came on mine, I came on yours. I think this is our third one total together. Yeah.
Okay, so you came out of retirement recently, which I was excited to see. Yeah. I like a good, you know, coming out of retirement, you know.
I, and I, I just wanna- I kept checking if your, your email newsletter was in my spam filter or something, and I was like- Oh... maybe it's in, in, in- No...
trash or- And, and I, I just wanna be clear, this is a one-and-done retirement situation, but yeah. No, but like, you know, great minds, you know, they happen. This happens all the time with inven-inventors, right?
Like, you know, multiple geniuses come, come with, like, very similar, like, you know, discoveries at the same time. And, and instead of weed, but they just happen to be newsletters. [chuckles] Yeah, exactly. Yeah.
But... And there were newsletters, the best newsletters are newsletters about newsletters. Echo. That's... Well, that was the irony. I was like, you know- Yeah...
this, that, that, that piece that I released, it got, it got picked up.
I got reached out to by a couple publications, the bigger ones, and I was like, "You know, I sent this in a newsletter," the irony of, like, me talking about the doomsday of it and the impact and effectiveness it still reached.
But that was nothing about, I think, like, some of the confusion that happened there. I was not writing that about the next twelve months.
I was, I was writing about just, like, this is, this is someone in two thousand nine saying, "Hey, we should probably think about building out display advertising on- Yeah...
on the website and, and kind of thinking about it that way." Okay, so you... So we're gonna talk about newsletters here. Yeah. I, I don't wanna get into, to, to the next iteration of Workweek.
But, like, let's start, because I had written my, my own piece, 'cause I was down in, in your neck of the woods in Austin at a, at a newsletter conference. A newsletter growth- Marketing... marketing, right. Yeah.
Newsletter marketing conference. Yeah. Yeah, yeah, yeah. And great conference. It was totally different for me because it wasn't, like, a typical media conference, right? Like, the...
That's all, like, doom and gloom talk and complaining about algorithms or complaining about Google or complaining about whatever. And this was like, you know, I, I described it a- as, like, information entrepreneurs.
And there's... I feel like the newsletter world is a little bit bifurcated, and I, I, as always, I try to straddle both worlds, Adam. Yeah. I wanna, I wanna, I wanna de-risk. I wanna be in both camps.
I wanna be Switzerland. But, like, it... I compare it to... There's, like, there's, like, the Substack world, I feel like, which are- Yeah... it's very, like, writerly, you know?
And it's like, it's a very different, like, community, if you will. And then there's, like, the Beehiiv, ConvertKit, I guess they're Kit now, that kind of world, and that's... I just use that as shorthand.
But to me, it's, it's defined by information entrepreneurs that are really good at the acquisition strategies, and they're looking to build businesses, and content are the ways they build businesses.
And, and it reminds me of the DTC world, and you sort of... We both landed on that a little bit, and it's, you know, I think it's an interesting comparison.
But give me, first of all, you've been in the email world for a while, email newsletter world, I guess, for, like, ten years.
Give me the macro of, like, what you were talking about and why this is an inflection point right now. Yeah. So the...
I'll start with, like, what pushed me over the edge to kind of want to write it today, of the inflection point today, but, uh, then I'll look back historically.
So last week, I met with one of the growth agency, one of the people running one of the growth agencies, which, you know, that conference was thrown by someone who runs a growth agency for newsletters and all that.
And, but I met with someone, and he's like, "Man." I'm like, "How you doing?" "Making hand-over-fist money right now." And I'm like, "Really?"
And he's like, "All of us are."The Warren Buffett quote of like, "Be, be fearful when those- Yeah...
are greedy and be greedy when those are fearful," was like sh- going through me and I'm like something like this just isn't normally the case that everyone's making tons of money.
And, and then I, you know, just started thinking, you know, you know, and I've been processing for Workweek for two years, like how... three years, how is AI gonna disrupt the business?
And I think it's people have been a little bit of they're picking lanes to think about that, and then kind of assuming that the lane that they've picked.
So let's talk about like content creation, like gen AI is like, oh, well, writers are always gonna have a place like AI. It's like this is like I'm talking like AI is the internet. It's not like a specific task.
So like the people that said like, "Oh, like people are still gonna like send mail. Internet's not gonna ruin mail." It's like that's not like the only thing it does. And I think AI was, is kind of in that point.
And so I, I had this moment where I, I thought, I don't think people are realizing that something with consumer behavior shifted with AI. It's getting more curated, more relevant, more useful.
And then on top of that, Beehiiv, which, uh, like we-- I think we both gave them a little bit of money. Like we- Mm-hmm... I'm a huge fan of Tyler. Like, and, and I think- Oh, yeah...
it's important to note, important to note that like I used Shopify as an example, the platforms will win. Like Beehiiv is gonna do really, really well.
The difference is that they're demo-- and because the tooling is democratizing access, people are just getting more newsletters.
And like, I don't believe the total addressable market of newsletter readers is anywhere close to growing as quick as the amount of newsletters being sent out.
And that then, if you like look at it, it's like, oh, something, something's gonna happen. And I, and I had this moment of trying to think through like my own newsletter experience.
And about 10 years ago, I met with my number one contact at a client of mine. It's a Fortune 100 brand. And I mean, she had more money than you could ever realize- Mm-hmm... when it came to ad dollars.
And I took her out to like a really expensive breakfast in Austin, and I was moonlighting for The Hustle at the time, and I said, "Hey, I'm leaving. I'm gonna go do this company, and we're gonna have a daily email."
And even at the time, I call it daily email 'cause I didn't-- I thought newsletter had like a bad connotation. And, and I said, "I want 50 grand for the year." And this woman used to give me 150 grand in a day.
And I said, "I need 50 grand for the year. It'll be... I'll make it totally worth it." And she was like, "Newsletters, like the thing you like value add in all our IOs. Like why would you ever build around newsletters?"
And 10 years ago, people didn't really generally on the masses believe you could build a habit and a relationship with a reader through the inbox. And today, I think everyone believes that.
And because of that, there's an, a mass amount of, of information happening there, and there's gonna be a shift of like, what's next, because it can't last forever, 'cause nothing ever does. Yeah.
But let's, let's, let's also like dig into this, this Shopify example, 'cause I mean Shopify, you're running an e-commerce, 'cause you have background in e-commerce too, right? Yeah.
Like running an e-commerce site was really complicated for a while. Right. Right? And we didn't have that many brands. And I think the DTC world exploded for a few reasons.
Like one was just Shopify made, was kind of like Substack or any of these, in that it make, it makes being an e-commerce company like an afternoon, right? Yeah.
And at least being able to sell something, then you're like, well, you need to be able to have a product. With content, it's far easier, right, to have a product.
But, you know, with, with Shopify, all the supply chains were in place in, you know, in China for the most part, and it, it became very... even the branding, a lot of it was done by Red Antler.
Like, you know, uh, and it led to an explosion of brands. Anyone on Instagram in that era, you know, all of a sudden, like your feeds were overwhelmed by an incredible amount of choice.
I remember when I was at Digiday, we had this modern retail brand that we started, and we did this like DTC event. And I was talking with this woman who had a... She was selling like bathing suits.
Like she had a DTC brand on bathing suits, right? And I was like, "Are there a lot of those?" She's like, "Yeah, there's something like 3,000 or so o- on like Instagram." 'Cause like it doesn't take...
There's not a lot of fabric that's needed for a bikini or whatnot. And like, you know, the margins are really good. And, and [chuckles] and I was like, "Wow, I don't think that can last."
And then fast-forward at the newsletter conference, and I'm hearing about 3,000 AI-focused newsletters on Beehiiv alone. [chuckles] And I'm like, uh-oh, alarm bells are going off. [chuckles] Yes. That's... I mean...
And it's a... And I think the thing that people have to always remember is this is a commodity business. It's, it, it is fundamentally something that is, is a commodity of information.
And of course, with commodities, sometimes there's really luxury ones, really valuable ones, highly quality-made ones, and other times it's not.
And when normally the pattern that you recognize and I recognize is when you lower the barrier to create a commodit- commoditized product, you get a lot more of them, and a lot more of them are shitty.
And so like Jacob Donnelly said this last year, and I thought it was very... He's like, "I don't know if we're in a newsletter bubble. I think we're in a shitty newsletter bubble."
I thought that was like a clever way to kind of like talk about it, but at the same time, it's impossible, and really this is who I wrote it for, is like if I was Morning Brew and I was, you know, myself, people who have larger businesses, tens of millions of dollars in revenue built on newsletters, the disruption's gonna impact you too in the same way that impacted Casper and Lisa and Allbirds, and both in terms of valuation, but also because of competition.
And I think that's like what someone has to be thinking about. Yeah. I mean, I think that's-And I think what's interesting is [sighs] and maybe this actually goes to, to... There's more with DTC on this one.
I don't know the exact examples. Casper could be one of them. You know, there's a lot of pattern matching that happens in all of these- all of these businesses. Like, Alex Lieberman was...
And, and Sam Parr were both at that event, and Alex was one of the co-founders of Morning Brew. He actually just executed, fully exited the business. He and Austin Rief, his other co-founder, they...
Axel Springer now fully owns it. And then Sam, of course, was one of the founders. I think he was the founder or one of the founders of, of The Hustle. They're... Yeah, one of them. Okay.
You know, and, and they're-- I sort of put in my piece they were kind of like the demigods of, like, this world. You know, they're like the celebrities of, of the- Yeah...
newsletter world, and neither of them are doing newsletter businesses now. [laughs] It's just another like... I'm like, "Oh. Like, wait a second.
The, the sort of kings of the, the newsletter world are not doing newsletters," and Sam's doing a community business, and, and Alex is doing a B2B content marketing agency business.
Those businesses were built in a completely different time. Like, as you said, you know, when you're going back to this, you know, fancy breakfast taco with the client, I mean, that was a different era.
That was before Morning Brew exited for whatever. What did they exit for, like, 70- It was before Morning Brew existed, right? Like, I mean, like- Yeah...
and I think the only ones out there at the time, like, she was referring to newsletters as what Daily Candy was doing, which that wasn't... It was a transactional- Yeah... newsletter, right?
It was like, "Oh, look at this shit that you could buy." Wasn't thinking about it as, like, actually the distribution method of information, and that, that's just totally pivoted.
And I think, you know, it's, it's, it's credit to those examples and Industry Dive and Morning Brew and The Hustle having exits. People like to chase money, but also the tooling.
I mean, like, I, I said this in my piece, but, like, we ran a cohort analysis in 2018, 2019 which allowed us then to spend faster and pay growth because I could actually do the science of what worked and what didn't work, and that allowed us to leverage to grow faster.
I mean, we had engineers who built that for us. Now you can pay 99 bucks a month with Beehiiv and have that at your fingertips to make better decisions about how to grow.
And I think, you know, that's, again, I think it's, it's not necessarily talking about the negative impact of that. I think it's amazing democratized access to, to people in that way. But when you, you...
If you take a big, big step back and just think about, okay, now this new technology like Beehiiv and Kit have unlocked more newsletters being sent out, and the inbox is more crowded because of that, and then AI is helping with curation and relevancy, maybe not great yet, but it, yeah, I, I believe it's coming.
There's, like, something there, and that's- Mm-hmm... gonna happen and change. And, you know, today I corrected someone.
Someone's like, "Oh, Adam, I totally agree with everything you wrote, except, like, you know, this isn't Facebook or, you know, whatever. Like, we, we don't have to worry about the algorithms."
And I was like, "The inbox is- Yeah. "The inbox is a platform. It is- Well, yeah... not different." There's a lot of motivated reasoning there. I mean, you know, I think when...
Because everyone got their legs, you know, chopped off by, by Fa- by relying on Facebook, now you're seeing something very similar happening in SEO. I mean, SEO has usually been...
I mean, it's gone through different waves and, you know, people, the Google dance used to happen, and the Google dance would, would have winners and losers.
It became a fairly stable algorithm, if you're gonna bet on an algorithm, is the most stable one. Now it's completely unstable, and it is also, you saw Chegg just starting- Suing... suing. Yeah. Google, and that's...
You know you're losing when you're [laughs] trying to sue Google. Right. I, I, I mentioned, I mentioned that. I mean, they were gonna go bankrupt no matter what- Yeah... but, like, the...
I actually love that they're bringing that lawsuit now 'cause then they're gonna disclose all the, the, the, you know, inside data that they have about the loss of traffic they had. Yeah. Look, if Yelp...
Yelp, Yelp spent a generation trying to [laughs] trying to sue Google, so I, I guess I'm not, like, I'm not super ho- hopeful on that. Well, and, and I- But there's gonna be other...
I mean, I just did a podcast that we released today with People Vs. Algorithms where we talked about getting Chegg'd and who, who is gonna get Chegg'd, and- I love that. Great segment. [laughs] Yeah, I know.
[laughs] I was like, I vowed to be, like, much more optimistic, Adam, [laughs] and then all of a sudden I'm like, "Wait, why are you guys pulling me into this who's gonna get Chegg'd?"
Honestly, I love- Well, you know- I love to play this game, though. You actually... I think this is actually a really good... How you started this with the difference of, like, the media conferences.
Like, you go to AMO and the other ones that are, like, exist like that today. Sometimes it's, it's doom and gloomy sometimes, right? Like, it's like, "Oh, we're all losing traffic. We're all fighting this." Yeah.
And then you go to the newsletter marketing conference, and everyone's like, "Well, look at the up and to the right graphs."
And it's funny, I don't actually think, which is, which is why you living in both places is actually probably what makes your perspective better.
I actually think both sides could probably learn the lessons- Yeah, exactly...
and patterns a little bit here, and, like, the up and to the right newsletter people should probably ask the other side, like, "Hey, what has gone wrong in the last 15 years for you?
Is there anything I can pattern recognize that's gonna happen- Yeah... to me?" And I think that's part of it. Well, I think beyond the algorithm, because, I mean, I think you make a, a really good point. I, I...
There's a few, like, really good points that I, I took away from your piece is, you know, one is just that as more information g- goes up, you know, the battle for attention gets even fiercer.
And, like, so I think a lot of times those of us who are in the sort of information space, we think it's always the other people, but we're all the problem at the end of the day. All of us.
We're all trying to grab people.
Do you know, I was, like, realizing, like, when you go to, like, the supermarket and there's the, the person on the sidewalk who tries to wave and step in front of you to get you to sign some, like, petition, I'm like...
And you, at least me, I mean, I get, like, annoyed by those people. I'm like, "Ah, no time." I'm like, "I am that person. That is me." [laughs] Yeah. You know? And that's all of us. I, I, that's...
I wrote, I wrote this out very specifically in the way that I, like, presented that. I said... I, like, wrote out the, like, words. One, at best, one, one out of two emails you send someone opens.
You think they give a shit about getting that in their inbox?
Like, if someone told me, like, "Hey, the thing that you open 50% of the time, I will only show to you when you a- when we think you actually will want to read it," I'll be like, "Yeah, great."
Like, don't do that for emails, like, from my direct reports and whatever. But, like-You're talking about, like, we're bragging about people sometimes reading these things 40 to 50% of the time. That's not good.
It's not the newspaper like it used to be. Like, it's not, that habit's- Yeah... not great. And I think people completely overestimate the affinity that exists of their content to, to the audience. Right.
And the other sort of motivated reasoning I think that people e- end up having, and it's just natural, right, is around the direct connection, right?
Like, so email was looked as, looked at as a refuge from all these unpredictable algorithms. You know, you... Did, you... To me, media businesses are, are fairly simple.
It's about what you make, uh, how you distribute it, and how you make money off it. Like, all the rest is, like, basically ladders up to that- Mm... as far as I'm concerned. Yep.
And distribution is, you know, without distribution, you're, you're, you got no shot, right?
And I think the idea behind getting more stable distribution through this, quote-unquote, "direct connection" to an audience is very attractive, but there's a big asterisk there, and it's that, eh, not really direct, right?
Because you're going into an inbox, and the, the tech companies control that inbox, and they have a different set of... They have to think about different things, right? And when it gets...
I covered direct marketing when, earlier on in my career when CAN-SPAM Act happened. Like, email marketing was a total mess.
Like, and then what ends up happening is regulators either step in, or the tech companies do the daddy's home routine. I go back to- I love, I love the daddy's home line. [laughs] Daddy's home. You said that earlier.
[laughs] You know, like, there's a lot of daddy's home going on in the- Mm... in the overall economy, right? Yeah. It's the daddy's home moment.
And, you know, look, the reality is everyone likes, you know, a, a rambunctious slumber party, but at some point [laughs] you need daddy to, like, you know, calm down. Like, "What the hell is going on here?" Yeah.
And that's always happened in digital media because you find a seam, whether it's in distribution or monetization, and guess what? Nothing stays undiscovered. There are no secrets in this business.
Everybody piles on to it. Yeah. And I saw this with pop-ups, man.
Pop-ups, every single publisher, you knew when the, the end of the quarter was coming without looking at the calendar because the pop-ups just became insane.
And so the browser company step- stepped in and shut them down. Yeah. You know?
And- Well, and that, that, that's the, that's the point that I think that everyone needs to realize that there's a dependency, of course, in the inbox, okay. Let's, like, we, we've talked about that.
But then those companies that control that inbox are consumer-driven companies. They do what is best- Yeah... for their users, and they have proven it, of course, with the browser, with the pop-ups.
They've done that, right? And, like, there's a startup kind of email platform called Superhuman, and I, I'm a- Mm...
huge fan and customer of it, and it saves me right now, like, probably three to five hours a week of my email time.
And they just announced their AI kind of tool, and this is actually was, like, when people are like, "This is so far away," I was like, "You should see what- Yeah... they're doing. It's not." And they're a startup.
They're flexible. They're fast. It's not Google. But, like, sooner or later- Yeah... that is, that- Competition... the competition's going to drive, hey- And look, look at the third- Yeah... party cookie.
Do you think Google wants to, like, dismantle a- a- an architecture that, that they make tons of money off of? Absolutely not.
The only reason that Google, uh, is, is, is moving on the cookie front and, and changing the architecture of digital advertising that they're winning at and they're dominant in is because competitors do it, and they have to keep up.
They, like, you know, Apple saw that this was a weakness. I don't really necessarily believe that Apple is, like- Yeah... obsessed with our privacy. Maybe. I don't think so much.
I, and I, and I actually, I told someone this, I was like, "The reason why the cookie actually didn't get killed is 'cause consumers actually didn't care." You know, like, they didn't actually...
Like, I don't actually think most people care. They- It's like, where's the harm? They, like, they- I never really got the harm.
Yeah, I don't think actually consumers, like, cared about the best, getting more relevant ads. And so- Maybe turn down the retargeting, but, like- Yes... other than that- That's-... like, I don't know...
it, and so, and guess what? Like, they didn't do it 'cause, like... But if there was an up in arms of everyone being like, "I hate this, my privacy," you have one competitor do it, you have to do it.
And, and, and, you know, with the inbox, I think it's, it's just gonna be more selective of it, what it is. And, you know, someone was like, "Well, what..."
Someone responded to my bad newsletter with a really good question. They said, "Well, like, what value do newsletters have at that point?" And I said, you know, the honest answer is, like, "I don't, I don't know.
I can't, I can't predict the future." But if we look, look back and try to pattern recognize a little bit, it's kind of what happened to the website in 2015, '16, right?
All of a sudden it was like, well, your, your traffic, people aren't just, like, going to your site naturally. They're using Google to, like, get quick information.
Your fans, your more loyal folks are coming to the website. And then by 2019, websites still existed. People still built them. They still happened. They just had less value, and I think newsletters will follow similarly.
It's not like I don't think people will abandon having newsletters as a channel. I think the effectiveness of them are going to go completely down similar to what happened with websites. Yeah. Channel. That's- Yeah...
I think that's the key word there because I, I was gonna, I think I had talked with Matt, who had done the conference, Matt McGarry, and I, I wanted to do a session on why newsletters are not a business to, like, tell [laughs] people because I don't, like, they, they can be a, a, a, a...
They can be, like, a starting point for a business. But, like, ultimately, you know, I think they, they have a lot of advantages. Starting a newsletters is great because, like, you don't need to, like, tech.
It's, like, right out of the box. You can have, like, a business in an afternoon really. Yeah. And you also do get first-party data. You understand who, who the people are, and that's good.
It is a lit- it is more stable than just, like, publishing stuff to a website. Predictability was always- Yeah... the...
When, when we, when we went through some diligence stuff at The Hustle, when we were, like, talking to acquirers, my line was like-This isn't about the reason why this is better than everything else is because predictably I can hit a button and reach forty to fifty percent of the people on this list, and that is, like, the advantage.
In twenty eighteen, nineteen, twenty, I think that was, like, very true, and there was no clear path of how that could change. I think what I kind of rang, rang the, the bell on yesterday was I see that changing.
I, I think that predictability is gonna go away a little bit. And there's, there's... That, that, that's kind of know for sure you're going to be seen by forty percent of the people that you have their email list.
It just might not exist as much in the near future compared to, like, that predictability and safety that you had for so long. And so basically, you see a typical thing of the inbox is, you know, gets flooded, right?
And, and let's also be clear, email newsletters are k- are ha- are a hack, right? It's not a publishing. It's, it was never built to be...
Just like the third-party cookie was not built to be some sort of the, the linchpin of an, a digital advertising architecture. Email was not built as, like, a, a place for, for publishing. It was- Correct...
it was a communications, a one-to-one communications medium.
Like, and then it got hacked, you know, originally by, by marketers and then by publishers when, when publishers and marketers are kind of the same thing at this point, like.
And, you know, because of that reason, and, a-a- in some ways, that's the strength, I feel like, of email newsletters, is it is in a communications architecture.
And so, if done well, I feel like email newsletters can have a more of a personal connection.
And I think that's why trying to write an email newsletter, like, I, I think it's, like, better to do it almost as much like a regular email message people normally get.
It's just, you know, I think the best compliments I've ever gotten about email newsletter is like, "Oh, I felt like this was written for me." And I'm like, "But it was." Yeah. [laughs] And a bunch of other people.
That's also why, like, you know, and this is...
Let's talk also, like, think about I- when I created one of the first decks at The Hustle to help convince my, like, enterprise advertisers that they should come on, I had this side by side of no reply at.
Remember how people used to do that? Like, no reply at, like- Oh, yeah... don't reply to this email. That was weird. And it was-- But, like, people, marketers would do that. It's so weird.
But, like, it was literally the largest signal ever of, like, "Hey, I'm not a human. Don't respond to this. I'm, I'm just here to push this thing to you."
And then next to it was, like, basically, like, a picture of, like, Sam and his, like, signature or something like that. And it was, like, basically, like, "Hey, we're humanizing the inbox."
And, like, there's a hu- we respond to replies. We, like, we show people that there's a human here.
And I still think that is without a doubt the best way to cut through and stand out, and that's, you know, my whole thing around, like, individuals over faceless institutions. Yeah.
I think that, like, doesn't go away at all. It's even more important today. I actually just think if you're not that, you're even more screwed. Yeah, for sure. So let's talk about winners and losers then.
If, like, assuming that it goes in this direction, AI is great at summarization. There's obviously a ton that is flooded into the email inbox. No, email's not dead.
I think, like, I, I looked up before this conversation that email actually started in nineteen seventy-one, right? And I think- Yeah... I think- And I never said email is dead either, by the way.
I don't believe that to be true. [laughs] I think in nineteen seventy-two, someone declared, like, email is dead, and then they've done it- Yeah... like, multiple times a year ever since then. So, like- Right...
no, email is not dead, okay? Like- No... Adam is not saying that. I'm not saying that.
But things change, obviously, you know, and, and just the pattern of history of everyone, you know, I compare it to the children's soccer game.
Everyone just clumps around wherever the ball goes on the field, and the email ball has had a clump of children around them. [laughs] Right.
And, you know, usually then, then we get daddies, so we got all my little, my, my little- Yeah... sticks.
Let's talk about winners and losers 'cause, I mean, AI, let's just assume that, that they're, it, it is gonna step in. It is gonna get much better at summarization. It is going to...
It, it's gonna make email less of a direct connection. It's gonna, it's gonna be more obvious that this isn't really a direct connection and that you, you're still at the mercy of others. Who...
Let's just start with, let's start with losers. Why don't we start with losers? Who are the losers here? Give me one loser, then we'll go, we'll go by loser.
So the, the folks that have, like, I don't know the exact date on this, but I know they, like, sold recently, so I'll, like, call them out a little bit on this.
But, like, the Neuron, which is one of the AI newsletters, just sold and got hyped up a lot, had, like, five hundred thousand subs, and they mostly grew through the recommendations engines of, like, and the paid and paid ads.
And I, I'm not... I, I have nothing. The, they sold. The guys who started the business made money, so, like, good for them, and they got out at the right time. Whoever bought that, I think, just kind of dropping that.
Like, no one knows that. No one cares about that newsletter. Like- And that is just, like, that's a, that's one of those, like, AI tips 'cause there's a, there's an entire- Yes...
genre of, as I said, it's thousands of publications that are, you know, they're, they do different things, but most of them are around, look, there's this, there are all these AI tools out there that normal people, or I guess, or most people are like, it's changing so fast that they're like, "Oh, I don't know what's what."
And so- Right... they help, you know, their aggregation. Yeah. That's what it is.
And I think, like, aggregation in its core, you know, and I think the, the morning, you called about this, like, the Morning Brews for X, the whatever, the Hustles, the ones that, like, used great voice and curation, I think, like, for the, the Morning Brews of the world, I won't put them as losers because I think their brand is too good.
Like, I think they've exceeded past. They're also, they're social. Like, they've done such a good job of diversifying channels that, like, I think they have... They're, they're gonna be fine.
But all the people that wentThat tried to say, "That business, I'm gonna do," where, like, I can basically in two hours take the top five news stories and, like, write my view of it with no, like, real differentiation or subject matter expertise.
Yeah. They're done. Like, they're just... And if, and, you know, my challenge actually yesterday, the thing I was probably most in my head about it, you...
This is, this is me not having the editorial background of the, of, of the pressure of hitting publish.
But I was asking myself before I hit it, I was like, "If AI tried to summarize this, could it actually effectively do it without the nuance that I'm saying here?" And I, and I...
That was the standard that I was trying to exceed, and everyone below that standard, I think is in a heap of trouble. Okay. So
I, I f- I guess what I'm hearing from is, like, obviously it's like any market that compresses. Like, the middle always gets crushed, right? But, like, undifferentiated sort of gets, you know, and the commoditizes.
I think in the email world, I would say a lot of the commoditized- Yeah... stuff is things that are, are... They're aggregation.
You might call it curation, but there isn't some particular necessarily, like, point of view that comes to it, or expertise that is, is layered on top. Well, and it, it's like, and I...
It's about, like, also, like, memorable. You know, the whole, like, thing, the ad that everyone has stolen that Morning Brew and The Hustle spent, like, tens of millions of dollars on is, like, make...
Be smarter in, with to your boss in five minutes or whatever, you know? Oh my God, everyone does that. And, and I know.
And the, the funny thing is today, if you actually tested that as a litmus test of, like, when was the last time someone said, "Hey, I read this thing today by this newsletter." Name that newsletter.
It might be a person, might be a brand. Has anyone actual... If you're, if you don't actually have people doing that, it, it is like you- it's you're not providing value. And I think you're...
Instead, you've created a huge arbitrage and, you know, that's, there's... I, I worked... A guy that has now, you know, he worked with us at The Hustle as the head of growth, he's now at Work Week.
He started his career doing the social arbitrage back in the day in 2013 on Facebook, where you would... He would, like, use Lil Wayne's Facebook page and, like, post, like, clickbait shit.
And then, like, it was the one you had to, like, click through all the page views to, like, get to the back. Okay.
And it was like he would pay Lil Wayne, like, 50 cents a click, and then if someone clicked all the way through, he'd make, like, 80 cents.
And, like, there was all those websites back then that, like, basically just arbitraged this, like, whole thing. And, you know, they were like, "Yeah, when the good times are good, it was great."
And then one day, Facebook said, "We're not allowing any websites like that anymore to be, get exposure," and they minimized and killed it.
And I think that's what's, that's, that's the next path for all these people that don't actually provide value and just create the arbitrage. All right. How about this as a winner? Substack.
I think- Because, because they're moving away from email in some ways. Like, it's like, it could become a refuge. Yeah. I, I...
Look, I think Medium was built with such great intention, and Substack is what Medium hoped to be. And, and you're right.
It's got the, it's got the idealists, you know, and, like, I mean, I've shit on Substack for so long.
[laughs] And to their credit, and I say this, like, really, it was probably ni- first publicly nice thing I've said in a very long time. You know, I asked him about, "Hey, why don't you have advertising?"
in, like, 2019, and he was like, "We would never do that." And I was like, "Well, you're fucked." [laughs] And I've had that stance ever since then.
And to their credit, they've created a cohort of idealists to how you wrote it, like, you know, that, "Hey, I care about my craft. I charge a subscription for it. You have to pay for it."
And then they've attracted readers that have that same kind of attitude. Is it a $600 million business? Absolutely not. But- Yeah... take value- And, and, and by the way, they have some Ponzi scheme aspects- I-...
to that business. Absolutely, too. Yeah. I wrote that- I mean, look, a lot in the newsletter world to me, like, and look, digital media has this, but there's a lot of Ponzi scheme-type things going on. Like, there's...
And that's what I was trying to get at. There's... I feel like on the Beehiiv/Kit side, there's a kinda, like, get rich quick, like, you know, I mean, the, the, the neuron. I got, I got it wrong.
Like I said, I said they were teenagers. I think they graduated from college last year. But, like, you know, [laughs] there's... So that was a big error on my part. They were 22, not 19.
But, you know, look, there's a lot of people trying to hack capitalism right now, and there, there is an aspect of that that's not, like, insignificant in- Yeah... the newsletter world.
To me, it's, like, adjacent to the, the FIRE, the financial independence, retire early crowd, crypto, meme coins. Derivatives are, are really big now. There's all kinds of things. W- what's his?
Even sports gambling, honestly. Like, we have this society where a lot of people are looking to hack capitalism, and the internet has always been good for looking for [laughs] like, seams.
So, like, [laughs] like, whether- Yeah... it's Lil, Lil Wayne. This is the first I heard about Lil Wayne's Facebook page. Oh. But- And there, there's a million of those.
And, you know, I think also to, you know, to, to bring it back a little bit to Shopify and that comparison of what it's doing, like, they're saying is, "Arm the rebels," right? Like, they knew what they were doing.
They were like, "Hey, entrepreneurs, like, tomo- buy tomorrow, you can have a shop. You can, like, do your own thing." Yeah.
And, like, Beehiiv couldn't just, like, steal the same thing, but honestly, I think they're doing the exact, like, same thing. They're arming, like, the entrepreneurs. Yeah.
So but here's my thing, and I, again, this is all about where you come from, and I admit my bias completely to, from coming from, like, the journalism/con- being a q- quote unquote content guy, right?
Where kinda like DTC to me, looking at DTCThe, the sort of big flaw that a lot of these companies couldn't get around is that they weren't pr- really product companies, that they...
'Cause I, you know, I used to edit the, the, the stories that came out of, like, our fashion and, and- Yeah...
beauty publication, and like, they were kinda like all these, they all, all had these, like, nonsense, like, stories about how, "Oh, well, we discovered this problem that we needed to solve," and the problem that they discovered was always between their first and second year at Harvard Business School.
Just so happens that that epiphany always happened right then. Always. And they were marketing. They were marketers who just attached the product at the end.
When you have 3,000 bikini brands, like, the, the bikini is, is kinda irrelevant.
Like, it could be anything, like, at that, at, at- Well- Because y- the supply chain's just sort of set up, and I kinda feel like a lot of, a lot of...
And, and tell me if I'm wrong here, because there's different ways to accomplish it, and I'm not saying that people will not be successful trying to be the next Milk Road or something like this. But finding a...
It's, like, sort of just pattern matching to, like, okay, I'm gonna attach, like, the content area after I figure out the distribution. AI's hot now, so I'm gonna, like, do AI.
And then I compare it to even, like, like, a, a Lenny Rachitsky, where it's like, Lenny's clearly incred- he's, he does this Lenny's Newsletter. It's about product management.
That's my favorite non-Workweek newsletter, is how I describe it. And he, he's clearly... It wasn't... I don't know how to put it with him.
Like, you know, Alex guy did, worked with him, who I do a pod- other podcast with, had Airbnb. And, and he's like, "Yeah, Lenny was, like, one of, like, dozens of product managers at Airbnb."
So it's not like he's like... And I don't mean this like a f- like to be offensive. No. It's not like he's a world-famous, like, product guy or something. He's not Steve Jobs or something. [laughs] No.
It just so happens he's, like, he's good, he's very consistent, and he has nailed, like, the execution of this.
Now, out of that million, oh, there's a lot of funny money in that million because of Substack recommendations. Well, and you know, you've seen the chart, right? Where, like, he had really amazing growth.
Like, for, for, like, someone who built it, he had incredible organic growth.
And we know, like, I wrote this a- actually yesterday, is, like, would you rather have 25,000 organic newsletter subscribers, no recommendations, no paid? Like, they signed up because they heard about you.
Or 250,000 with 95% paid. Like, which one is more interesting? And it, to me, it's clearly the 25,000 organic.
And Lenny hit that, and then Substack turned on their recommendations and made them, made him the face of their platform in a lot of ways.
And you can see the pivot in the chart when they do that, and it's up and to the right. And that's, that's like...
It's like Lenny is the one of the best content creators in the world, so he deserves that, and also, he still had a platform help him get that.
And also, by the way, and this maybe will go into, like, w- some of the winners is, you know, he has the makings of, like, a, a quote unquote community.
I mean, this is something Sam talked about a little bit at the, at the conference, 'cause he's, he's now doing a community with, like, Hampton, right? Yeah.
And it's for entrepreneurs, and it fits completely, and the sort of media aspect to that is, is using a podcast really as, as, as an acquisition tool.
It's the way I would sort of, the way I understand it looking at it from, from the outside. But I think when you think about, like, like, he, Lenny can actually turn people out. He had a massive, like, event.
He's got 20,000-plus people in a Slack channel. That must be a bonkers Slack channel [laughs] when it's that s- it's not for me.
But I mean, I, I, I struggled with, like, you know, 70 people in a Slack channel, much less 20,000. Right.
But, like, I think, you know, where I think one of the winners that comes out of this, and this is sort of, I think, the direction you guys are going at, at Workweek, is I see people wanting to gravitate to, to quote unquote community.
I'm putting it in quotes because, like Sam made the point, there's a lot of people out there with, with audiences who are pretending they have communities, right? And I, I've seen this repeatedly.
But that is, when you, if you think about, like, a moat, if you can get to that community, like, that's the most protected I feel like you can be in this kind of world. Yeah.
I think there's a c- one caveat I'd say to that, but yes.
I think, you know, ultimately moving from a publishing business to a platform business is actually what it is, going from, like, a content business to a community business. And what I...
And the way that I kind of, like, talk about that internally, it's what I wrote in our annual letter a little bit to the company, was we're moving from being solely known as a publishing company to today we have more people having discussions and creating more content and uploading it to our, to our, you know, the, the networks that we've built, than we're publishing.
And that, that switch of UGC when you have sustainable community in that capacity, I think ultimately the thing that's really, I would challenge everyone to kind of like, just, like, think about, and there's no easy way to do this, but, like, even if you're building it on Slack, Mighty Network, Circle, it's still a platform.
Like, you still don't own the walls. And I think there's some opportunity for sure for... I mean, and this isn't Workweek.
I think there's someone building a platform for community where it gives as much data to the owner back as they would if they owned that platform themselves, which is still, like, not the case with these others.
'Cause the data side today is actually the inherent risk of, hey, if all those discussions get put into Google's search algorithm or ChatGPT's LLM, sooner or later that just, uh, people aren't gonna go back.
It, it's still faster to go to those other things.
So you have to have a community that I think is protected from a data perspective, those discussions, that conversation, but also, you know, the real level of success is, like, are more people self-organizing, self-discussing, than me leading it?
And that's, like, what I think, like, it's really difficult to do that. I don't think there's gonna be tons of winners, but that's actually- And a lot of it, by the way, is out of your control. Like, we, I- Oh...
I saw this at Digiday. We hadWe had different brands, and different brands had different profiles about whether they had a real audience or, like, a community. And, and events are not a community. Like, they're not.
Like, just, you can get people to come to an event and- Mm... not necessarily have... It's a different type of community. I, I do think- It depends on the event.
But B2B, a lot of the events, the community is, like, a sales community. Like, buyers and sellers, like interacting. It's a marketplace, and that's a great thing to do, is have a marketplace.
But that's how the event takes place. I mean, like, I would say, like, Hustle Con was actually the true community of what we had at The Hustle because people there, I think, like, this is also, like, defining.
Community is, like, looking at the root of that a little bit, it's about, like, what do we, what pains and what beliefs do we have in common?
And like, that's, like, church, all types of communities, that's, like, where it comes from. And yeah, if you throw a B2B event where it's like, "Hey, you're here to be a lead.
You're here to buy something, sell something-" Yeah. "... go," yeah, there's, like, nothing truly there, right?
But like, when you have someone, like, cry on stage and talk about, like, this, like, terrible, tough time they had building a business, and they got out of it or like...
And then this is, like, things that we did at The Hustle that... And, like, you have people, like, all of a sudden share this, like, moment where you're like, "Wow, I see myself in them." Like, that's actual community.
And I think events are actually the best way to get that started in terms of, like, going o- offline to online, doing events at person gets that connection rolling. Okay. Yeah. Yeah.
And I guess- I think my point was like, it's like you can have community without, like, necessarily events, but you can have events without community. But I, I... It could be colored by my, my experiences. I know.
I, I think, like, that's true.
I think my op- I guess what I'm saying is having in-person events, like, if you were starting a church, it'd be a hell of a lot easier to get, like, 20 people together on a Sunday and, like, sing together, and then later do something online.
It's just easier to get that feeling- Yeah... than, like, doing something online naturally, and I think that's, that's, like, a little bit of how I think, like, where it, it does shift. But not all events are community.
Yeah. But I don't think any newsletters are actually community at all. Like, I, I, like, you can't have a community where people don't talk. Right. They don't connect.
Like, what you can do, which is different, is you can set the table where people believe and understand there's other people like me out there, and I, like, need to go find those people.
And that's how we use newe- newsletters is, like, wow, our newsletter for HR is called I Hate It Here. Why? 'Cause, like, all of a sudden these pe- HR people are finally like, "Thank God, someone gets it.
Our fucking job sucks." No one has ever said, "I hate it here in HR." Now I have- Right... this, like, relatability that, that it's the start- Yeah, I get that... that kind of sets the table of community.
With HR, people like to dump... They, they back up the, the, the problems truck and just dump it on, like, HR. [chuckles] And there's no, as, as we, as I've learned, uh, there's no HR for HR, so, like, that's... Yeah.
But I think that's the purpose of community and newsletters and how they go. Yeah, I think that's, that's true with events.
I mean, the thing of events, you, you need to, like, fi- I mean, on B2B events, I always thought you need to find, like, the group within a company that feels, like, misunderstood and needs to find their tribe.
Like, you know- Yes... for us at the time, like, it was, like, Ad Ops people. Like, Ad Ops is a great a- area, like, used to be where problems, you know, get dumped on.
It's like, yeah, I s- I s- we sold, like, two things to the same audience. Figure it out [chuckles] or not, give them... Money doesn't gi- give it back. And you can figure it out. Right.
And, you know, getting those people together does actually, I, I, I take your point, like, have a community aspect.
So you guys started really as, like, creators plus newsletters, and now I get the sense that you are kind of mo- more... I don't know. Forget about my sense. Where, where are you now? Yeah.
I mean, three, little over three years ago got started, and the belief was then that in B2B, there was a huge gap of hearing from individuals. Lenny was a big inspiration of this.
Hearing from individuals that, like, actually understood the language, the insights, spoke the inside baseball of their field.
And we, you know, created a, a new model of working with people a little bit there, generally to attract people that do the job.
So, like, our e-com one, she's a chief growth officer, our HR one, she's a chief people officer, and started building newsletters and podcasts around their own insights.
And but, you know, from Becca and I wrote a memo in July of 2021 about where we wanted Workweek to go and our, our long-term vision.
And ultimately, you know, it was to the point of a newsletters being a channel, content being that. We believed that there was something much bigger downstream.
If you could get this group of people that are normally pretty hard to reach, like people who run health systems, for example, one of our categories, and then be like, "Holy shit, this is the best thing I read this week," or, "The best thing I heard," or, "No one's ever said that out loud, thank God," there's opportunities downstream to, to build that into even a bigger business.
And what we learned through testing a bunch of different shit, we built a vertical SaaS business, we built... I did a huge conference. We did all sorts of stuff.
We sold and built a bunch of tools in 2023, and that learning of that was like, "Hey, let's go, like, now look at what, what kind of is best here." Like, you have all this- Mm-hmm... attention, what was best?
And what was so obvious and clear, not just, like, quantitatively, but qualitatively, was, like, the best thing was allowing these people to, to talk and be with each other.
And if we go, kind of go back to what we learned in that time period was, you know, our creators were becoming, like, incredibly famous, like, weirdly. Like, HR famous, econ.
Like, they started, like, getting asked to do this, and people are like, "What do you think about that? How do you think about that?"
And that's, I think, speaks to the individuals over faceless institutions kind of belief.And community actually unlocks that across the board.
And, you know, I, and I think like Jacob Donnelly's Slack community for me is actually a great example.
Like, I can go in and be like, "Hey, three people that I, I know know this space, or I believe know this space, I wanna ask you like a question immediately." And it's like, well, that's pretty helpful.
And how could we kind of build a product that wasn't a product, but kind of the product, and allowing us to, to build a community and a, what we kind of call our, like, networks with other people in the spaces where they're verified and can have conversations and talk.
And we started building that two years ago.
Last, you know, June, we announced it publicly, and now that's really like a big focus of ours is growing these memberships and growing the networks out to allow more people to kind of- Mm-hmm...
to, to connect and, and meet each other. So does that mean you're not like a newsletter company anymore? I never thought we were, personally. Okay. I think it was like a, a step in the journey, for sure.
And we, by the way, we had podcasts from day one too, so like I think that's always... Like, we have two podcasts in the top 25 of their categories, and always have. But I believe we're, like at our core- Mm-hmm...
we have always been a community content company at like what we do, and I don't think those don't go together. Like, there's no, there's rarely cool communities that don't start from content if you like go look back.
And, you know, the other, the other kind of hope of that is that we think, you know, ultimately the hard, the big goal is to create connections. Yeah.
And that, that's great for vendors, but that's amazing also obviously for operators. Yeah. Yeah.
And I think that's one, one of the, I, when you get to one of the winners, but I think one of the winners likely is like those that, like you s- you can start in newsletters, but you, you wanna, you wanna diversify your channels, right?
Yeah. And it, you know, it can depend, like podcasts are like an obvious co- you know, component. Some people are, you know, they, they, they can't necessarily or, or don't wanna make that sort of leap.
Some people go more into video. Video and podcasting are now kind of- Interchangeable... kinda interchangeable. Obviously, like events, any kind of gathering and in-person is, is a different channel.
It's a deeper, you know, connection to, to people than, than like, you know, emailing them regularly. Yeah. Well, and I think like people that I think are gonna continue to do really well are event first businesses.
People, if you are able to throw a successful event, no matter what, I think the likelihood to create more offshoots of that is much easier than going newsletter first.
And so winners are people who have amazing, great in-person large events. I think like the opportun- the optionality for them is much higher.
Morning Brew I think is gonna continue to do really well because they've diversified so greatly off of newsletters in terms of their social channels are now just absolutely amazing, great content- Mm-hmm...
for their audience. And that, that provides them more optionality. And then I think the last one is the folks that focus on building connections within niches.
And, you know, we don't, we don't have a ton of time to, to dig into this, but my favorite company in the world is publicly traded, called Doximity, and it's a, it's a community for doctors. Mm.
And it was started the same time that Spiceworks was started, where I started my career, which was a community for IT people. And they have this amazing walled garden of verified physicians.
Last year, they did 500 million revenue. They're publicly traded for 13, tw- 12, 13 billion today. And they're, they're doing, they're mostly ads, like 80, 70, 80% ads.
They're doing what I think a lot of people should be focusing on, which is like, how do we help these people actually meet and connect with people that can help them either live a better life or better career? Awesome.
Well, I'm gonna go check out Doximity and do exactly what they're doing, but for, uh, media professionals. [chuckles] You, you should. But Tam's not quite as big. Yeah, that's okay. Don't, don't- It's good...
I don't need 13 billion. [laughs] I'm, I'm fine with one. Well- One's fine... now you, now you just got the Workweek pitch. Yeah. Now you know what we're doing.
But yeah, that's, those will be big winners, the people that focus on that. And, and then the channel thing, just the last third, to sum this up to the econ that we talked about so much.
You know, the winners of that D2C boom got into retail stores. They like went to, they went and like multipl- like multiplied the channels that they were in. They went on Amazon. They like actually- Yeah...
diversified where they went to. And the people that actually deeply believe they have a legitimately good content product, it's like follow that playbook.
Where, where, where else can you put that information other than where it's at today? Yeah. Do you think I can call this, this episode like, "Newsletters Aren't a Business?" Is that too provocative?
[laughs] Uh- We'll workshop it here. [laughs] Uh, I mean, I was- I know, I'm just looking for clicks, you know? Like- I, I almost, I almost titled my subject line yesterday the, "The Doomsday for Newsletters is Coming."
So yeah. All right. You know, that marketer, that editorial person, you need to be a marketer, so use that clickbait. Exactly. All right. Thanks, Adam. This was fun. Yeah, appreciate it. [outro music]