Adam Ryan, CEO of Workweek, joined me this week to discuss his recent warning that the newsletter sector is overheated. Some points from the conversation:

• Newsletters are a commodity. The number of newsletters is growing faster than the number of readers. AI tools and cheap platforms like Beehiv have made launching one easy, but most newsletters lack true audience affinity.
• The inbox is not really a direct connection. It’s a platform like any other, subject to change. Apple’s Mail Privacy Protection has broken open rates, AI tools like Superhuman summarize newsletters without opening them, and inboxes are being segmented, reducing visibility.
• Paid growth is a weak foundation. Many newsletters rely on paid acquisition and cross-promotion. The moment that engine turns off, engagement often collapses because there’s no real audience connection.
• Winners are thinking beyond email. The most successful publishers are building businesses around community, events, and services. Morning Brew, Workweek, and Lenny’s Newsletter all extend beyond just newsletters.
• Newsletters are a starting point, not a business. They are an MVP—a way to build an audience—but real success comes from expanding into new distribution and monetization channels.

Welcome to the Rebooting Show.

I'm Brian Morrisey.

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 1971, but the market is clearly

shifting with an astounding number of email newsletters popping up.

I was told that there's something like 3000, 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 emails

always build as being a direct connection to your audience, and that is true.

To a degree because at the end of the day in 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 make sense of

our emails, but are also likely to be a net negative for many newsletters.

And we discussed that shift, how to manage it as a newsletter operator.

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 bmorrisey@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 Adams in the show notes.

All right.

This is a very exciting podcast.

I am, I'm rejoined by Adam Ryan, I think you're on one of my earlier podcasts.

Maybe even on a couple I.

you came on mine and I came on yours.

I think this is our third one total together.

Yeah.

So you came outta retirement recently, which I was excited to see.

I like a good, you know, coming outta retirement.

You know, you just, I kept checking if your, your email newsletter was in my spam filter or something.

I was like, maybe it's in, in,

No, and and I, I just want to be clear, this is a, one and done retirement, situation, but

No, but like, you know, great minds, you know, they happen, this happens all the time with invent inventors, right?

Like, you know, multiple geniuses come, come with like very similar like, you know, discoveries at the same time.

And, and so did we, but they just happen to be newsletters,

yeah, exactly.

but, and there were newsletters, the best newsletters or newsletters about newsletters.

That's, well, that was the irony.

I was like, you know, 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 that 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.

I was, I was writing about just like, this is, this is someone in 2009 saying, Hey, we should probably

think about, building out display advertising and the website and,

Okay, so you, so we're gonna talk about newsletters here, and

I, I don't wanna get into to, to the next iteration of work week.

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 market.

Yeah.

Newsletter.

Marketing conference.

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 an 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, I want, I wanna, I wanna de-risk, I wanna be in both camps.

I want to be Switzerland, but like, it, I compare it to, there's like, there's

like the Substack world I feel like, which are, 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 beehive.

ConvertKit, I guess their kit now, that kind of world.

And that's, I just use that as a 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, I. 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 10 years.

Gimme 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 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 is like, man, I'm like, how you doing?

He's making handover fist money right now.

And I'm like, really?

And he's like, all of us are.

The Warren Buffet quote of like, be, be fearful when those are greedy and be greedy when those are fearful was like

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 of, 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 has shifted.

with ai it's getting more curated, more relevant, more useful.

And then on top of that.

Beehive, which like we, I think we both gave them a little bit of money.

Like we, I'm a huge fan of Tyler, like, and, and I think it's important

note, important note that, like I used Shopify as an example.

The platforms will win, like beehive 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 Fortune.

More Money Than You.

Ever realized when it came to a dollars and I took her out to like Ave in Austin and I.

I'm leaving.

I'm gonna go do this company.

and we're gonna have a daily email.

and even at the time I called it daily email 'cause I didn't, I thought

newsletter had like a bad connotation 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.

But let's, let's, let's also like dig into this, this Shopify example.

'cause I mean Shopify, you know, running an e-commerce, 'cause you have background in e-commerce too, right?

Like, running an e-commerce site was.

Really complicated for a while.

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 sub or any of these in that it make, it makes it.

Being an e-commerce company, like an afternoon, right?

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, 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 3000 or so on, like Instagram.

'cause like, it doesn't take, there's not a lot of fabric that's needed for bikini or whatnot.

And like, you know, the margins are really good and, and, 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 3000 AI focused newsletters on beehive alone.

And I'm like, uh oh, alarm bells are going off.

Yes.

That's, I mean, and it's, and I think 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 a 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 commod commoditized product.

get a lot more of them and a lot more of 'em are shitty.

And so like Jacob Donnelly said this last year and I thought it was right.

He is like, I dunno 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, 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.

Yeah.

There's a lot of pattern matching that happens in all of these.

all of these businesses like Alex Lieberman was, and, and Sam Par 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, reefed, his other co-founder, they, the Axle 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.

I.

Yeah, one of the,

you know, and, and there 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

newsletter world, and neither of them are doing newsletter businesses.

Now.

It's just another, like, I'm like uhoh, like, wait a second.

The, the sort of kings of the, the newsletter world are not doing newsletters.

I mean, 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 the exit four, like

It was before Morning Brew existed, right?

Like, I mean, like, 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 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. 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 20 18, 20 19, 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 beehive 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 democratize 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 beehive 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 you, I, I believe it's coming.

There's like something there and, that's 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, the inbox is a platform.

It is 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.

I. in SEOI 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 started suing Google.

I mean, that's, you know, you're losing when you're trying to

right.

I, I, I mentioned, I mentioned that, I mean, they were gonna go bankrupt no

matter what, but like the, I actually love that they're bringing that lawsuit out.

'cause then they're gonna disclose all of the, the, the, you know,

inside data that they have about the loss of, traffic they had.

Look if Yelp, Yelp, Yelp spent a generation trying to, trying to sue Google.

So I, I guess I'm not like, I'm not super hope, hopeful

Well, and,

there's gonna be other, I mean, I just did a podcast that we released today with people versus algorithms,

where we talked about getting chugged and who, who is gonna get chugged.

I love that great segment.

yeah, no, I was like, I vowed to be like much more optimistic, Adam, and

then all of a sudden I'm like, wait, why are you guys pulling me into this?

Who's getting any checked?

I

Well, I, you know,

to play this game

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 a MO 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.

And then you go to the newsletter, marketing conference and everyone's like, well look at, right.

Actually.

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

Yeah, exactly.

patterns, a little bit here and like the up into 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 pat or recognize is gonna happen 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 mean, 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 go goes up, you know, the battle for attention gets even fiercer and like, so I.

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, 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.

You know?

And

I mean that, I wrote, I wrote this out very specifically 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'll only show to you when you, when we think you actually will to read it.

I'll be Don't emails reports.

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 not great and I think people completely overestimate the affinity that exists, of their content to.

Right.

And the other sort of motivated reasoning I think that people 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, to me, media businesses are, are fairly simple.

It's about what you make at how you distribute it and how you make money off it.

Like all the rest is like.

Basically ladders up to that, as far as I'm concerned.

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 me 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 and earlier on in my career

when canned spam act happened, like email marketing was a total mess.

And then what ends up happening is regulators either step in or the tech companies do the daddy's home routine.

I go

love, I love the daddy's home line.

You

Daddy's home, and like, there's a lot of daddy's home going on in the, in the overall economy, right?

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 you need daddy to like, you know, come down like, what the hell's going on here?

That's always happened in digital media because you find a scene,

whether it's in distribution or monetization, and guess what?

Nothing stays undiscovered.

There are no secrets in this business, and everybody piles on to it.

And I saw this with, popups, man, popups, every single publisher you knew when the, the end of the quarter was

coming without looking at the calendar because the popups just became insane.

And so the browser company stepped, stepped in and shut 'em down.

You

Yeah.

Well, and that's the, that's the point that I. Everyone

needs to realize that there's a dependency, of course, in the inbox.

Okay, let's, we, we've talked about that.

But then those companies that control that inbox are consumer driven companies.

They do what is best for their users, and they have proven it, of

course, with the browser, with the popups, they've done that, right?

And like there's a startup kind of, email platform called Superhuman, and I.

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 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 that is that you, the competition's going to drive.

look look at the third 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 has 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 obsessed with our privacy.

Maybe.

I don't think

I, 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

it's like, where's the harm?

I never really got the harm.

yeah.

I don't think actually consumers like cared about the best, getting more relevant ads

Maybe turn down the retargeting,

Yes, that's it.

And so, and guess what?

Like they didn't do it because 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 what it is.

And, you know, someone was like, well, what, someone responded to my.

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 20 15, 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.

Yeah.

Channel.

That's, I think that's the key word there, because I, I was gonna, I

think I had talked with, Matt, who had done in the conference, Matt McGarry.

and I, I wanted to do a session on why newsletters are not a business

to like, tell 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, and you also do get, first party data.

You understand who, who the people are, and that's good.

It is a, it is more stable than just like publishing stuff to a website.

was always 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 40 to 50% of the people on this list.

And that is like the advantage in 20 18, 19 20.

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 and I think that predictability is gonna go away a little bit.

and there's, there's that, that's, kind of no, for sure.

You're going to be seen by 40% of the people that you have their email list.

It's just might not exist as much in the near future compared

to like that predictability and safety that you have for 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, are ha are a hack, right?

It's not a publishing.

It was never built to be, just like the third party cookie was not built

to be some sort of the, the linch pit of a digital advertising architecture.

Email was not.

Built as like a, a place for, for publishing.

It was, it was a communications, a one-to-one communications medium, like, and it ain't 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, and 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

Eman Newsletter is like, oh, I felt like this was written for me.

And I'm like, but it was,

Yeah.

and a bunch of other people

that's also why like, you know, and this is, let's 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 app.

Remember how people used to do that?

Like, no reply at, like, don't reply to this.

Uh, weird.

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.

The best way to cut through and stand out and that's, you know, my

whole thing around like individuals over faceless institutions.

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.

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 has 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 1971.

Right.

And I

Yeah, and I never said email is dead either, by the way.

I don't believe that

I think in 1972 someone declared like email is dead, and

they've done it like multiple times a year ever since then.

So like, no email is not dead.

Okay.

Like.

Adam's 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.

And, you know, usually then, then we get daddy.

So we got all my little, my, my little shtick.

Let's talk about winners and losers, because I mean, ai, let's just assume that, that there, 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?

gimme one loser and 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

500,000 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.

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 caught a dropping knife.

Like no one knows that, no one cares about that newsletter.

and that is just like, that's, that's one of those like AI tips.

'cause there's a, there's an entire 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 are, 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 they help, you know, their aggregation.

Yeah.

And I think like aggregation, its core, you know.

The, the morning you called about this, like the morning brew for x, the hu

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 their 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 went.

That 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.

They're done.

like there's 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. 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 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, in the commoditized.

I think in the email world, I would say a lot of the commoditized 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, you know, 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 to your boss in five minutes or

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 named that newsletter.

Might be a person, might be a. Has anyone actually, 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 work a guy that is now, you

know, he worked with us at the Hustle as the head of growth.

He's now a workweek.

He started his career doing, the social arbitrage back in the day in 2013 on Facebook.

where you would, he would like use 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.

And, it was like he would pay little 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 arbitrage this like whole thing.

And.

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

All right.

How about this as a winner, Substack.

I, you know.

Because they're moving away from email in some ways.

Like it, like it could become a refuge.

Yeah, I, I, look, I think, medium was built with such great intention.

Substack is what medium hope to be.

and and you're right.

It's got the, it's got the idealist, you know, and like, I mean, I've shit on Substack for so long.

and to their credit, and I say this like really, it was probably

a nice first publicly nice thing I've said in 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.

and I've had that stance ever since then.

and to their credit, they've created a cohort of idealist 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.

And, and by and by the way, they have some Ponzi scheme, aspects to that business Absolutely, too.

I mean, look a lot in the news is letter 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 beehive slash kit side.

There's a kind of 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, 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 the newsletter world.

to me it's like adjacent to the, the fire, the financially independence,

retire early crowd, crypto meme coins, derivatives are, are really big now.

There's all kinds of things.

What's 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 like seems to like, like whether it's the

Lil Wayne, this is the first I heard about Lil Wayne's Facebook page, 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 in 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 to, by tomorrow you can have a shop.

You can like do your own thing, own.

And like Beehive 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 slash con being a quote unquote content guy, right?

Where, kind of like DTC to me, looking at dtc, the, 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.

Because I, you know, I used to edit the, the, the stories that came out of like our fashion and, and beauty publication.

And like, they were kind of 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, and they were marketing.

There were marketers who just attached the product at the end.

When you have 3000 bikini brands, like the, the bikini is, is kind of irrelevant.

Like it could be anything like at that, at at, because you, the supply chains just sort of set up.

and I kind of 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 Ky, where it's like Lenny's clearly in incred.

He's, he does this Lenny's newsletter.

It's about product management.

My favorite non-work week newsletter is how I.

He, he's clearly, it wasn't, I don't know how to put it with him.

Like, you know, Alex Guy I did, worked with him, who I do pod other podcasts with At 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, like to be offensive.

It's not like he's a world famous like product guy or something.

He's not like Steve Jobs or something like, it's just so happens.

He's like, he's good.

He is very consistent and he has nailed like the execution of this.

Now out of that million, there's a lot of funny money in that million because of Substack recommendations.

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 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, 95% paid, like which one is more interesting?

And 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 into 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.

Also, by the way, and this maybe will go into like where 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?

And it's for entrepreneurs and it fits completely in the sort of media aspect to that is, is using.

a podcast really as, as, as an acquisition tool is 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 on a Slack channel.

That must be a Bonker Slack channel.

it's not, 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.

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 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.

I think there's a one caveat I'd say to that, but yes,

I think, you know, ultimately moving from a publishing business.

Is.

Like a content business to community business.

And, what, and the way that I kind of like talk about that internally, that'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 then we're publishing.

and that, that switch of UGC, When, 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

it and there's no easy way to do this, but like, even if you're building it on Slack, mighty Networks 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.

because the data side today is actually the inherent risk of, hey,

if all those discussions get put into Google search algorithm or Ubes, LOM.

Sooner or later that, that people aren't gonna go back, 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.

And a lot of it, by the way, is out of your control.

Like we, I, I saw this at Digit.

We had, we 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.

Community, like they're not like just, you can get people to come to

an event and not necessarily have, it's a different type of community.

I, I

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

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 a B2B event where it's like, hey.

You're here to be a lead.

You're here to buy something, sell something, 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 it things we did at the 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 offline to online, doing events in person, gets that connection rolling

Okay.

Yeah.

yeah, I guess 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.

no, I, I think like that's true.

I think my, 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, 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, but not all.

Yeah.

Are actually community at all.

like I, I like, you can't have a community where people don't talk, 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 new newsletters is like, wow, our newsletter for HR is called, I hate it Here.

Why All.

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 this like relatability that, that it's the

Yeah, I get

kind of sets the table of

with hr, people like to dump, they, they back up the, the, the problems truck and just dump it on

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,

Yeah, I think that's, that's true with events.

I mean, the thing of events you, you need to like find, 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, for us at the time, like it was like ad ops people, like

ad ops is a great area like used to be where problems, you know, get dumped on.

It's like, yeah, ISIS.

We sold like two things for the same audience.

Figure it out.

We're not giving money, doesn't give it back.

you can figure it out.

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.

Created, created a new model of working with people a little bit there, generally to attract people that do the job.

so like our e-comm 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, there was something much bigger downstream.

This 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 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 e-com.

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 individuals over faceless institutions kind of belief.

S that across the board.

and you know, I, and I think like Donnelley's Slack community for me is actually a great example.

Like I. 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 in 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, to, to connect and meet each other.

So does that mean you're not like a newsletter company anymore?

I never thought we were personally, I think it was like a, a step in the journey.

for sure.

And we, by the way, we have podcasts from day one too.

So like, I think that's always like, we have two podcasts in the top 25 other categories, and always have.

But I believe we're like, at our core, we have always been, uh uh.

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 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 wouldn't get to one of the winners, but I think one of the winners likely is like,

those that, like you, you can start in newsletters, but you, you want to, you wanna diversify your channels, right?

And it, you know, it can depend, like podcasts are like an obvious, 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, kind of 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.

I think like, people that I think are gonna continue to do really well are event first businesses.

people, if you were able to throw a successful event.

I think the likelihood to create more offshoots of that is much easier than going first.

And so winners are people who have.

Amazing, great in-person, large events.

I think like the opportunity, 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 for their audience.

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.

And it was started the same time that Spiceworks has 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 in revenue.

They're probably traded for 13, 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, media professionals.

you should, the tam's not quite as big.

Yeah, that's okay.

Don't, I don't need 13 billion.

I, I'm fine with

Well now you, now you just got the work week pitch.

now you know what we're doing.

yeah, that's, those will be the big winners that people that focus on that.

And, and then the channel thing, just the last, the, the sum of this up to the

econ that we talked about so much, you know, the winners of that D two C boom.

Got into retail stores.

They like went to, they went and like multi, like multiplied the channels that they were in.

They went on Amazon, they like actually 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.

Do you think I can call this, this episode?

Like newsletters aren't a business?

Is that too provocative?

We'll workshop it here.

uh, I mean, I

I know.

I'm just looking for clicks, you know,

I, I almost, I almost titled my subject line yesterday, the, the doomsday for newsletters, is coming.

So, yeah.

you know, that marketer, that editorial person, you need to be a marketer.

So use

Exactly.

All right.

Thanks Adam.

This was fun.

Yeah, I appreciate it.