October 20, 2022 • 34 mins
Chris Best is co-founder and CEO of Substack.
Chris's problem: How do you help writers make a living from a thousand true fans?
Substack is a company that helps writers send subscription-based email newsletters. Which, as Chris says, is a very simple idea, built on top of some very grandiose beliefs about culture and ideas and commerce.
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Episode Transcript
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Speaker 1 (00:15):
Pushkin. In two thousand and eight, the writer Kevin Kelly
published this essay about a big, exciting, ultimately kind of
simple idea. If you want to make a living doing
something creative, you don't need millions of fans or even
hundreds of thousands of fans. You just need a thousand
(00:37):
true fans. The math works, Kelly argued, because of the Internet.
The Internet gives everybody everywhere the ability to connect with
everybody else, and it means that people like writers and
musicians no longer have to go through intermediaries like publishers
and music labels and retail stores that traditionally wound up
capturing most of the revenue from the sales of creative work.
(00:59):
If you can find your thousand true fans, Kelly argued,
and if you can figure out a way to sell
your work directly to those fans, you could make a
living doing the creative thing you love to do. I'm
Jacob Goldstein and this is What's Your Problem, the show
where entrepreneurs and engineers talk about how they're going to
(01:19):
change the world once they solve a few problems. My
guest today is Chris Best. Chris is the co founder
and CEO of Substack. Substack is a company that helps
writers send subscription based email newsletters, which, as Chris says,
is a very simple idea built on top of some
very grandiose beliefs, beliefs about culture and ideas and commerce.
(01:42):
More to the point, substack is one of the best
tests I've seen of the theory of a thousand true fans.
The idea for substack came to Chris and his co
founder Hamish back in twenty seventeen. At the time, Chris
had just left Kick, the messaging platform that he'd co founded,
and there were lots of things he thought had gone
(02:03):
wrong with media and the Internet. He'd always been an
avid reader and a believer in the power of writing,
and he wanted to share his ideas with the world.
And so naturally I was like, well, I should write.
How hard could that be. It's just typing. I already
know how to type. And I started writing what I
thought was going to be an essay or a blog
post that was kind of just detailing my frustrations with
(02:27):
the state of media and the Internet. It was sort
of this like a complaint or a screed of some
sort that was just like the Internet came along made
it global an incident free to distribute writing, which is great,
but at the same time, these platforms killed a lot
of the business models that used to support great writing.
Craigslis killed the classifieds, Facebook, Google took over the advertising industry,
(02:50):
and now we're all sort of stuck clawing for attention
on these various feeds waw, waw, waw, complaining, complaine. And
I sent this piece of writing to my friend Hamish,
who's actually a writer, and he very gently told me
you're not the original snowflake you think you are in
twenty seventeen writing a thing it says, wow, be Facebook
is bad for us, Like, you know this, this is
(03:13):
not exactly fertile ground. You didn't get the scoop on
that one. Yeah, I didn't get the scoop on that one.
He's like, I'll tell you that all of my friends
who are writers are not going to be shocked to
hear that there's been some disruption to the business model
that supports their work. And basically like, look, you maybe
write about all of this, but so what And you
sort of asked the question He said, the more interesting
(03:35):
thing would be, like, what do you do about it?
It's easy to complain, it's easy to poke holes. But
let's assume that all of this is true. How could
you even how could things be different? How could things
be better? And we started sort of arguing about that
and batting around a bunch of things, and we were
both subscribers to Ben Thompson's Stratechery at the time, and
(03:58):
we were like, you know that dude's making which is
just to be clear, that's a paid newsletter that lots
of people in the in the tech industry subscribe to.
It's an email letter that he's exactly. It's a paid
it's a paid email newsletter. We're seeing other people doing
these things where they're like, you know, you can write something,
you can charge for it. We were just fascinated by
this thing, and we ended up sort of hitting on
(04:19):
the idea of substack. Is this very simple thing that
does kind of two things. On the one hand, it's
this very grandiose idea that's aimed at this broad societal
problem of like, hey, this the total domination of all
of our attention by this business model of these engagement
maximizing platforms is bad, and we need to like create
(04:41):
a real alternative for that with a different business model,
and you know, it's like an alternate universe with different
laws of physics for how you spend your time and attention.
Very high faluting. But on the other hand, it's like
what if you could send people email and charge the
money for it? Right, right, And it's pretty low faluting.
It's like, you know, it's a very specific thing that
(05:02):
some people newsletter. It's an email newsletter. Yeah, people say,
what a newsletter. It's like actively unsexy technology, yes, right, right,
So I mean I'm curious. So you know, obviously substack
is a thing. Now I have to say, like, I
don't think of it as a substitute for you know, Twitter.
Twitter is my social media of choice. Unfortunately, I think
(05:28):
of it as more of a close substitute to something
like The Atlantic or The New York Times, who in
fact are now clearly building their own email newsletter businesses. Partly,
I presume in response to your success at substack, right,
have you found in whatever data you have that substack
is a substitute for social media. I think it's at
(05:50):
least a substit I mean it's at least a substitute
in that as readers, as consumers, we end up having
kind of like a finite amount of time. Yeah, so
every minute somebody is reading substack is a minute they're
not looking at social media but could make. And that
sounds kind of ridiculous when you sort of produced its
like everything is in competition with everything else. But I
actually think that's sort of like the fundamental shift that
(06:12):
we've undergone, Like the whole dawn of social media was
because we used to live in an age where it
was possible to get bored. Yeah, and you would have
time in your life where you're like, gee, I'm bored.
I wish I had something to spend my attention on
and if somebody could come along and give me something
for free to do, that would be a great deal.
And we've just come to the end of that age there.
(06:34):
There just isn't every chunk of your attention that you
ever want to spend on anything has been taken up.
And in fact, there's increasingly loud clamoring and your phone
badly absorb every second of your brain life. Still though,
I mean, it's possible that sub stack, that the attention
sub stack has taken and I'm happy for it. I
(06:55):
think it's great that writers can make money, and I'm
excited to talk about that. But it's possible that that
has come mostly from not from social media, but rather
from unsocial media. I mean, you literally have people leaving
traditional media places where they are writing columns and starting
to write substacks, right, Like, that's the it's a very
natural kind of adjacency. No, you know, to be honest,
(07:17):
it's almost certainly both. You know, people that had people
that were working as professional writers, right, a lot of
them can go to substack and get a great deal.
That's awesome, we love it. But there's an even bigger
cohort of people who were not professional writers before and
who but for substack, might not have been writing. Either.
Young people who didn't see a path and sort of
(07:39):
you know, might have gone to you know, had something
to give the world as a writer, and without this
model might have had to go to law school like
their parents wanted them to. Or people that work in industry,
or people that have some adjacent thing that you know,
making building an audience and sometimes on substack and sometimes
building a fortune, and who but for substack, would otherwise
(08:00):
not be writing. It's not like they would, you know,
have a job at the Atlantic or something and who
who I have never heard of, who most people have
never heard of, right, which is cool and interesting. I mean,
it's kind of like a smaller YouTube in that way,
right where there's just this vast array of niches that
people can fill. And so I mean I am curious
(08:21):
to that point to get a sense of basically the
distribution of I don't mean the literal email distribution, but
the sort of distribution curve of substacks of the newsletters
people write like, how big a substack? How big a substack?
What have we shared? I think we've shared that we're
over a million paying subscribers, hundreds of thousand of people
(08:43):
who started a substack. I forget what our latest So sorry,
a million paying subscribers and the what is the well,
I guess for that when the average subscription is like
sixty bucks a year ish, yeah, eighty somewhere in there. Okay,
So is that something like eighty million dollars a year
that people are paying not to you, obviously, but to
(09:05):
the writers, of which you get ten percent? Is that
the ballpark way to think about it? Yeah, I mean,
it's it's more than that, but it's that's you know,
that's the right, if I if I ballparked it at
one hundred million for the writers, ten of which goes
to you, would I be not wildly wrong. You're in
the right order, mind, dude. Okay. Um. And then so
within that, like again to your point of like, well,
(09:27):
there's a few famous people, and you know, I'm curious
to know how how the how the distribution works there,
you know, how much are the top people making? And
then like what's the median? Yeah, so the distribution is
super sort of power laws you might expect. So I
think the top ten people make something like twenty or
(09:49):
twenty five million bucks a year between them. Wow, good
for them, they should only live them be Well, yeah,
people were making millions of dollars a year. Individuals are
making millions of dollars a year. Individuals are making millions
of dollars a year, but a very small number. It's
like the Taylor Swift of substack and there's you know,
there's they're actually quite a healthy number people who are
making you know, real money. If you think of real
(10:13):
money is like multiple times which you'd make as a
writer at a publication. I definitely think of that as
real money. But Okay, so your question is like what's
the distribution and the like, tell me about the median person, Like, yes,
there are some superstars, and I am happy for those superstars,
but what's like a normal Like how many people are
(10:33):
making fifty thousand dollars year? Like fifty thousand dollars years?
Like up perfectly, you know that's a that's a living.
And if you can write your own email newsletter and
make fifty thousand dollars a year, that's cool. But how
many of those people are there? I mean it's like hundreds,
I think? Okay, okay, I mean if you're charging five
bucks a month and you can get a thousand, a
(10:54):
couple thousand people to pay you five bucks a month, like,
that's a living, and like a couple thousand people isn't
that many? Right? So? Like, how does that work? Are
there examples of that? Are there? Sort of things you've
found that people have made that work? Are there particularly
interesting niches will have filled? That math is very important
to why substack works. The fact that a relatively small
(11:17):
number of people can chip in five bucks a month
and start to be meaningful. And it's interesting because if
you can get to a thousand, there's usually not a
reason you couldn't get to two thousand or five thousand
or ten thousand over time, and then that's why you
get this sort of power law thing where you have
this upside. But there's lots of things about what it
takes to get there. The thing I think is most
(11:38):
interesting about it, though, is how different the kinds of
things you want to do to get there are from
the things that would that you would do if you
wanted to kind of like maximize your audience to get
ad impressions right all of a sudden, Your incentives if
you want to if you're trying to get your thousand
true fans, your incentive is to create something that a
(12:00):
thousand people deeply value and fall in love with and
want to pay you for and want to keep paying
you for. Right you want to earn and keep the
trust of a thousand people making something they deeply value.
And what that means is that there's if there's something
out there that's like that that a thousand people would
deeply value, but you couldn't necessarily get a million people
(12:22):
to click on it's very very valuable on substack, and
so there's a whole class of very valuable stuff that
otherwise might not get created that can now get created.
And so, I mean the obvious ones that come to
mind are sort of business related, and there have been
you know, industry newsletters have existed for a long time
for this reason, right, There are lots of industry newsletters
that are a thousand dollars per subscription because you know
(12:44):
your work is paying for it. I mean that's one.
Are there kind of less obvious ones, you know, ones
that are more oh less work related? Say, And that
was one of our earliest questions, and we sort of
we wondered this. We're like, well, okay, people if they
can if they can say that it's for their job,
or they can put it on a corporate credit card,
they'll pay for it. But will they really pay for
(13:05):
something else? But pretty quickly we had people doing kind
of like literary comedy and culture writing and politics and
the breadth of topics that it turns out that you
can make on substack is kind of ridiculous. There's somebody
(13:25):
writing reviews of canned fish. I don't know if he's
making a ton of money, but it's like that's the
sort of level of meeting to say, I mean, sure,
it's the internet, Right, so every niche you can imagine,
and then a ton more that you can't imagine are
going to exist. The interesting question to me is what
can you get a thousand people to pay five bucks
a month for? And and maybe more to the point,
like what have you learned about how to do that?
(13:47):
Because I feel like that trick is actually generalizable beyond substack, Right,
that's the basic, you know, minimum viable product. Find your
core customers, make them love you, iterate like, I want
to figure out how to do that better on the
podcast that I make. Right, it's clearly a more mass model,
but still the idea of like making a thing a
(14:07):
few people really love, I think is is really compelling.
And so what have you learned about how to do
that specifically? Yeah, so topic can be almost anything. The
things that really matter are you want to have a
distinct perspective. Exactly what that means depends on what it is,
but you want it to be either a distinct voice
(14:28):
or distinct worldview, or some distinct expertise or distinct sensibility,
something where the thing that the people are paying for
is not the content. Nobody has a problem that nobody
comes to substack and says I wish I could get
more email. I wish I had more things to me.
Nobody has that problem, right. The thing that you pay
for is I need this person's take or this person's thought,
(14:51):
or this person's recommendation, and I want them to curate
a slice of my intellectual life or my attention for me.
I want to delegate some of my worldview building to
this person who I've built up this trust with over time.
And in order to get that to worth paying money for,
you want that to be distinct enough that you're not
(15:15):
you know, you're not giving them something that they could
get in a hundred different places. And you do have
to kind of think about that integrity right being there
if you're curating a slice of their attention, being judicious
about what you're asking them to spend that attention. For
somebody gives you permission to send them emails or gives
you adds you to their podcast player, it's not only
(15:35):
should you send them good stuff, but you kind of
want to not send them things that are not worth
their time or are not interesting. You mentioned you called
it integrity, but the idea of respecting people's time their inbox,
and it reminded me of the fact that not only
is substack subscription based, people pay, you know, to get
(15:56):
a lot of substecks. It's pretty anti AD, right, like,
if you have a substeck, are you even allowed to
put ads in your newsletter? We definitely frown on it.
And this is an interesting point where we are very
anti AD, but we're also very pro freedom. Basically, like,
it's your editorial content. You're allowed to put what you want.
So we've fallen short of saying we're going to police
(16:18):
what you put in your newsletter, provided you're not literally
spamming people, which we take a very dim view of.
But we don't build any AD technology. We don't we're
not sort of encouraging people to sort of have a
hybrid model in general, even though that seems like it
ought to be appealing. We think that focusing on the
other thing actually maximizes the benefits of that thousand true
fans logic, Tell me more, Tell me more about that?
(16:41):
Is that you don't sound on the fence about it.
Has the company been on the fence about it? Could
you imagine becoming more proad. It's something we used to
get a lot from writers and the kind of the
logic is like, hey, subscriptions are money. Advertising is money.
One money plus two money is better than just one money.
Like it's like, wouldn't I make more money? I think
(17:02):
for in the writing world, people have seen enough success
on substack that it's people are starting to get that
the this model is working. And there's there's people who
are in that category of people who are making millions
of dollars a year on substack, who I personally at
the start had to convince to turn on payments. And
I'm like, no, I'm not gonna I'm gonna go do
(17:22):
some sponsorship thing or I'm just gonna grow it and
I'm gonna blow blow. I don't think I can really
make any money, and then I'm gonna just try it.
You know, you have whatever The New Yorker, the Washington
Post very very excellent publications that I pay for with
my own money, and I don't resent them running ads
as well. Yeah, I can. I can see the argument
(17:42):
for that, And I think people can make the argument
for podcasts. You know, I personally, every time I listen
to a podcast and there's a break, that's like, now
let me tell you about something else. I'm like, okay,
they're like coming right at me right now, you're coming
right at I'm not gonna and listen, I don't begrudge it,
but I'm not going to say that I love it. Now,
let me tell you about something else. We'll be back
(18:04):
in a minute to talk about bundling, unbundling and a
problem substack has not yet solved. Now back to the show.
So the first part of my conversation with Chris was
largely about that thousand true fans idea. The next part
(18:25):
of the conversation is about another famous tech saying, this
one is like kind of half joke, half idea, and
it comes from Jim Barksdale, who is a big tech
guy back in the nineties. The key line is this,
there are only two ways to make money in business.
One is to bundle, the other is to unbundle. Like
what do you make of that quote? What do I
make of that quote? I buy it, I think, and
(18:46):
I agree with you that so far subject has been
this big unbundling energy. Right. The fact that as an
individual writer you can go and start your own thing
and make it on your own and get the upside
of what you're doing and sometimes make you ten times
as much money as you've ever made before, and have
a business and all this stuff. That's wonderful. It's a
good thing. I actually think that there's a lot more
(19:08):
energy left in that thing. Um. I think people people
sometimes they're like, well, what's going to happen when people
are getting their eight substack subscription and they're really annoyed
that they have to have so many different substack subscriptions.
And I'm like, you know what, I like, bring on
that problem. I would love to live in the world
where that's your problem. I mean, obviously people that have
in particular would love to live in the world where
that's the problem. Of course, and there's you know, there
(19:32):
are some people who who have that today, there's some
people that are you know, subscribed to a whole bunch
of things, but far and away, I think there's a
ton of energy left in this sort of unbundling phase
of like, I'm a writer, I have something to say,
and I like, I want it to be my thing.
I do think there's an interesting effect where bundle economics
(19:53):
are real, and if we are successful at the grand
unbundling that we are in the middle of doing, at
some point there's this economic potential energy that for unlocking
the surplus of bundle economics for writers and readers, And
there's a bunch of ways you can imagine that happening.
Like one thing that's happening already is that substacks are
(20:13):
turning into companies and institutions, right, people are starting as
one thing and then building a newsroom or building a company.
And the other thing that would be, like the obvious
thing would be like, well, what if you just had
like a Netflix style thing, or like this is what
medium did. It's like, why don't you just have one
a substack subscription and then everything like you know, there's
some magic algorithm that dolls out like who gets the
money based on what? And the problem with that is
(20:36):
that it although it unlocks the bundle economics, it kills
the fundamental magic of what's good about substack, which is
the direct intentional relationship between the reader and the writer. Right, Like,
the whole deal is I'd choose what to spend. I
don't know exactly what the right solution to this is yet,
but my strong intuition is that the right answer is
(20:59):
that you do, in fact want a bundle or bundles
but that it needs to happen bottom up rather than
top down. I think that, you know, as with anything,
the hard part is making it simple. This is one
of the fun things about building products, building good products,
is you like sweat and curse and wring your hands
(21:22):
and pull your hair out for a long time trying
to wrangle a thing. And if you actually do a
good job at the end of it all, you show
somebody and they say, yeah, obviously, yeah, right, you idiot,
Like you spent how long coming up with like an
email newsletter with a website that takes money, you idiot? Like, yeah,
but that's actually good, right, And you're not there yet
(21:44):
for the bundle? Is that is that the upshot? Yeah?
And for the bundle, and we're still in the hard part.
And honestly, there's so much value right now, Like there's
there's so much value in these in the subscriptions as
they exist. And we're already doing a bunch of things
around cross promotion. We let writers recommend each other rather
(22:04):
than having some algorithm that recommends it. So that's another choice,
right In the same way that you're pretty clearly anti
ad you seem pretty clearly anti recommendation. Algorithm, and that
one is maybe more surprising to me because you know,
discovery is hard, and I feel like you must know
a lot about what people read, and if they read
one thing, they like another thing, Like why not make
(22:26):
that kind of you know, collaborative filtering recommendation? Yeah, and
I would add some nuance there, like I don't think
I'm against recommendation algorithms per se, but I think the
specific thing that I'm suspicious of is the thing where
you make an algorithmic surface that you as the reader,
delegate as the control of how you spend your attention
(22:50):
that has some objective that may not be your objective. Well,
now you just turned substack into Twitter, right, That's that's
the straw man version though, or YouTube? Right, Like you
go to YouTube and it's like yea, yeah, you subscribe
to that. But like, don't worry, here's what you really
want to call. You don't have to do that. There's
a way cooler version of it. That's just Hey, lots
of people who read a glace Let's also read Josh Barrow.
(23:11):
You might want to check it out. Like that doesn't
seem like you're trying to steal my mind, like a
social media platform. Yeah, and I think I would argue
that we are doing the cool version of this right.
And the two things that are important to me in
this are, number one, we're not just optimizing for engagement.
We're not saying like, here's what you're going to click on,
and we're saying here's what you might like enough the
(23:31):
one day you would pay for it. And the other
thing is where possible, we'd love to have it be
human powered. Right when you go to read a book,
the fact that an algorithm said to you that it
was the best possible book to you, even if you
could know that was the truth, might be less compelling
than somebody who you've trust and have gotten to know says, hey,
I think you should check this out for these reasons.
(23:52):
And so when you can have things that are that
are you know, incentivized the right way, and when you
can have human beings in the loop, we just think
that that's like a makes for a better experience, and
we've shown that you can make recommendations that people deeply
value that way. What's something you haven't figured out yet, Like,
what's something you're working on now, something maybe you've tried
and it didn't work, like what's a's a what's a
(24:13):
problem you're trying to solve? Now? Okay, I'll tell you
one thing that I'm really fascinated with is when you
get a bunch of people who deeply value this one
writer or this one crazy niche and you find all
the people who are willing to pay five or ten
bucks a month for that thing. Not only have you
(24:34):
given them a piece of media and a connection with
the author they deeply value, You've created You've sort of
crystallized this potential community. The writing and the writer and
the thing you subscribe for is kind of like the
bat signal that draws in the people. But over time
the community ends up being a major piece of why
(24:56):
of the value for people right being among all the
other people who value this enough to pay for it,
not having a bunch of trolls, because you can moderate profitably,
and so I think there's a tremendous amount of fential
energy there. It's something that writers and podcasters really want
from us, And I don't think that we've totally cracked
(25:18):
the answer to it yet, but we've been trying a
bunch of things. Some new stuff is coming up pretty soon.
That's pretty exciting. And I think if we can make
the community aspect of it, right, that will end up
being tremendously powerful. Well, it's interesting because it's like creeping
back towards social media, right, I mean, maybe a better
(25:41):
version of it, but fundamentally that's what you're talking about. Yeah,
I mean it's people talking to each other, people engaging
with ideas, people building relationships. And it's again it's sort
of in this I think of it as an alternate
universe with different laws of physics from the universe where
(26:01):
all of these giant platforms have grown up of the
kind of like massive engagement based AD supported thing, that's
one way to build it. And we're building a kind
of this alternate rails. So what's the thing you're about
to roll out? Am I allowed to talk about this one? Yes?
So we've been working on We've been working on chat.
(26:24):
That's something that you can do on substack chat like
real time, like like Slack style or g chat. Yeah,
you could look at you could think of Slack, you
could think of i RC back in the day. You
can think of Discord is like an amazing thing. Discord
seems like the closest model there is that, right, I
don't know discord that well, but that's a very it's
like a community oriented chat, right, I mean is that
(26:45):
what I should think of for what you're working on? Yeah,
I think closely related. Is it hard? Have you been
trying it and like not quite figuring it out? It's
been working fairly well. I would say we're being We're
trying to be thoughtful about it. Right. The thing we
never want to do again is kind of break the
magic of substack. And in this case, one of the
(27:05):
things that really matters is you want the writer to
be in charge. Right. This is something where I'm if
I have my community, like and this is my little island,
my own private social network. Um, I want to be
in charge of that. It's not I don't want it
to be something that ends up being like and people.
You know, there are substack writers who have tried having
a slack or a discord or one of the telegram right,
people just telling telegram, and it's often just like it
(27:28):
becomes like this source of pain for them. They're like,
oh my god, it's this whole thing and I'm like,
it's not mine and I can't really it's got a
life of its own. It's really get really spammy. You know. Yeah,
it's it's it's hard to make it right. And we're
not trying to make you know to the extent that
we're building. We're not trying to make the best standalone
communication product for any purpose. We're trying to make the
(27:49):
best place to build community and hang out with your
your substack audience and among your substack audience. Um. And
so we've been trying to like make sure that we're
building that with people who are actually doing that, because
this is the fun part about building something like substack,
which in my estimation is like a holy new thing,
(28:10):
is all of the interesting features of it are emergent.
You don't find out until you have the actual people
trying to use them, and then you find out whether
it's working or not. And so we're being pretty thoughtful
and building it with real people and getting their feedback
and making sure it's good. So such Stack is not
that big as a company, right an order of ten
(28:33):
million dollars a year in revenue is very small as
companies go, And yet I've heard a ton about it.
It's gotten a lot of coverage in the media. As
a journalist, I know that journalists love writing about other
journalists and writing about journalism, and I think that's part
of it, right, So you've gotten a lot of coverage
for that. Also, you know, your company has been criticized
(28:55):
for paying certain kinds of writers to come to the platform,
and you know, I'm not interested in relitigating the details
of that, but I'm curious how the sort of two
sides of that have played out. Right, How getting covered
much more than a company your size would get covered
if it weren't basically a media company or a sort
(29:15):
of media adjacent company. How has that been for you?
Have the pluses outweighed the minuses? How do you weigh that? Yeah,
the way that I think of this is that we
you know, substock has an outsize impact on the culture.
People care about it for reasons that are valid and
go beyond the money. We've taken a lot of heat.
(29:35):
We've had people very thrilled at us and very mad
at us, and I've always felt like we can't complain
too much about that. You know, we kind of set
out with these, you know, the two ambitions. But one
of the ambitions is very grandiose, right, It's about making
this new business model for writing and culture. On the
Internet and having that dramatically shape the world and who
(29:58):
people are. And there's just no way that you succeed
at that without, you know, running towards the fire, running
towards the heat of the culture war and the media
and the spotlight and all of the things that people
care about. And so as much as it can be
both thrilling and uncomfortable, I don't feel like we get
to complain. This is kind of what we signed up for,
(30:19):
and all of our paths to success do lead through it.
We'll be back in a minute with the Lightning Round. Okay,
let's get back to the show. We're going to close
with the Lightning Round. There are two names that come
(30:40):
up in the Lightning Round here that I didn't explain
during the interview, but I should have. One name is
Jane Jacobs. She's the author of a book called The
Death and Life of American Cities. The other name is
Matt Levine. He's a finance writer who writes a newsletter
for Bloomberg News. Now let's get to the Lightning Round.
What's the most important lesson you learned from reading Jane Jacobs.
(31:04):
I love the broad impact that's small, practical details of
the spaces we inhabit can have on how we live
our lives. And there's lots of stuff in Jane Jacobs.
It's like that. I don't know if all of it
is well empirically supportive, but there's this fascination with you know,
if you have homes that have windows at street level
(31:27):
and people are looking out, people walking down the street
feel a different way, and it's this very brass tax
like physical aspect of geometry that ends up broadly shaping
people's lives. I think cities are like that, and I
think that the digital places we create are like that too. Okay,
if you could have one person in the world start
writing a substack, who would it be? Might be Matt Levine.
(31:53):
Oh sure, me too. Same You would make so much
money it's absurd. I'm sure he's doing well, but yeah,
it's a good choice. Really really got me with that one.
If everything goes well, what problem will you be trying
to solve in five years? One thing I think about
if we're, you know, successful in all the things we
(32:14):
want to succeed at, this becomes this bigger and bigger
that the GDP of the sub stack of verse gets
gets more and more. You know, we are built on
this foundation of the ideals of a free press, the
ideals that writers should get to like, have their space,
and make what they want. One thing that I could
see being very interesting is as that goes international, having
(32:36):
that collide with various societies where unlike here in the US,
there's not a strong legal and cultural protection for the
idea that people should be allowed to write have ideas
people should be allowed to sign up for it. I
think that's not a free press, right, And it's not
a free press. There's not a free press. Yeah, and
yet on subject there is a free press. And what
does that mean for us that that should be an
(32:57):
interesting problem? Should we earn the right to confront it?
How many subseects do you get? Oh man, hundreds? How
many do you read? How many do you read? Many?
I pay for tens and I read probably at least
all of those ones. I read a lot of substack
to the it's really it's great. I'm an avid user.
I thought you were going to say it's a problem,
(33:18):
but I guess you wouldn't say that. Oh, I love it.
It's a great Everyone should should mimic me in this capacity.
What's one piece of advice you'd give to somebody trying
to solve a hard problem, have a grand science fiction
vision of what you're trying to do, and take one
(33:40):
step at a time. You think you're going to work
on Substack forever could be Is there something that would
like signal to you that it's time to do something else.
If we go to business and they physically have me
removed from the office, I would probably have to consider
my options. Chris Best is the co founder and CEO
(34:07):
of Substack. Today's show was produced by Edith Russolo, edited
by Robert Smith, and engineered by Amanda kay Wong. I'm
Jacob Goldstein, and we'll be back next week with another
episode of What's Your Problem.
Pushkin. In two thousand and eight, the writer Kevin Kelly
published this essay about a big, exciting, ultimately kind of
simple idea. If you want to make a living doing
something creative, you don't need millions of fans or even
hundreds of thousands of fans. You just need a thousand
(00:37):
true fans. The math works, Kelly argued, because of the Internet.
The Internet gives everybody everywhere the ability to connect with
everybody else, and it means that people like writers and
musicians no longer have to go through intermediaries like publishers
and music labels and retail stores that traditionally wound up
capturing most of the revenue from the sales of creative work.
(00:59):
If you can find your thousand true fans, Kelly argued,
and if you can figure out a way to sell
your work directly to those fans, you could make a
living doing the creative thing you love to do. I'm
Jacob Goldstein and this is What's Your Problem, the show
where entrepreneurs and engineers talk about how they're going to
(01:19):
change the world once they solve a few problems. My
guest today is Chris Best. Chris is the co founder
and CEO of Substack. Substack is a company that helps
writers send subscription based email newsletters, which, as Chris says,
is a very simple idea built on top of some
very grandiose beliefs, beliefs about culture and ideas and commerce.
(01:42):
More to the point, substack is one of the best
tests I've seen of the theory of a thousand true fans.
The idea for substack came to Chris and his co
founder Hamish back in twenty seventeen. At the time, Chris
had just left Kick, the messaging platform that he'd co founded,
and there were lots of things he thought had gone
(02:03):
wrong with media and the Internet. He'd always been an
avid reader and a believer in the power of writing,
and he wanted to share his ideas with the world.
And so naturally I was like, well, I should write.
How hard could that be. It's just typing. I already
know how to type. And I started writing what I
thought was going to be an essay or a blog
post that was kind of just detailing my frustrations with
(02:27):
the state of media and the Internet. It was sort
of this like a complaint or a screed of some
sort that was just like the Internet came along made
it global an incident free to distribute writing, which is great,
but at the same time, these platforms killed a lot
of the business models that used to support great writing.
Craigslis killed the classifieds, Facebook, Google took over the advertising industry,
(02:50):
and now we're all sort of stuck clawing for attention
on these various feeds waw, waw, waw, complaining, complaine. And
I sent this piece of writing to my friend Hamish,
who's actually a writer, and he very gently told me
you're not the original snowflake you think you are in
twenty seventeen writing a thing it says, wow, be Facebook
is bad for us, Like, you know this, this is
(03:13):
not exactly fertile ground. You didn't get the scoop on
that one. Yeah, I didn't get the scoop on that one.
He's like, I'll tell you that all of my friends
who are writers are not going to be shocked to
hear that there's been some disruption to the business model
that supports their work. And basically like, look, you maybe
write about all of this, but so what And you
sort of asked the question He said, the more interesting
(03:35):
thing would be, like, what do you do about it?
It's easy to complain, it's easy to poke holes. But
let's assume that all of this is true. How could
you even how could things be different? How could things
be better? And we started sort of arguing about that
and batting around a bunch of things, and we were
both subscribers to Ben Thompson's Stratechery at the time, and
(03:58):
we were like, you know that dude's making which is
just to be clear, that's a paid newsletter that lots
of people in the in the tech industry subscribe to.
It's an email letter that he's exactly. It's a paid
it's a paid email newsletter. We're seeing other people doing
these things where they're like, you know, you can write something,
you can charge for it. We were just fascinated by
this thing, and we ended up sort of hitting on
(04:19):
the idea of substack. Is this very simple thing that
does kind of two things. On the one hand, it's
this very grandiose idea that's aimed at this broad societal
problem of like, hey, this the total domination of all
of our attention by this business model of these engagement
maximizing platforms is bad, and we need to like create
(04:41):
a real alternative for that with a different business model,
and you know, it's like an alternate universe with different
laws of physics for how you spend your time and attention.
Very high faluting. But on the other hand, it's like
what if you could send people email and charge the
money for it? Right, right, And it's pretty low faluting.
It's like, you know, it's a very specific thing that
(05:02):
some people newsletter. It's an email newsletter. Yeah, people say,
what a newsletter. It's like actively unsexy technology, yes, right, right,
So I mean I'm curious. So you know, obviously substack
is a thing. Now I have to say, like, I
don't think of it as a substitute for you know, Twitter.
Twitter is my social media of choice. Unfortunately, I think
(05:28):
of it as more of a close substitute to something
like The Atlantic or The New York Times, who in
fact are now clearly building their own email newsletter businesses. Partly,
I presume in response to your success at substack, right,
have you found in whatever data you have that substack
is a substitute for social media. I think it's at
(05:50):
least a substit I mean it's at least a substitute
in that as readers, as consumers, we end up having
kind of like a finite amount of time. Yeah, so
every minute somebody is reading substack is a minute they're
not looking at social media but could make. And that
sounds kind of ridiculous when you sort of produced its
like everything is in competition with everything else. But I
actually think that's sort of like the fundamental shift that
(06:12):
we've undergone, Like the whole dawn of social media was
because we used to live in an age where it
was possible to get bored. Yeah, and you would have
time in your life where you're like, gee, I'm bored.
I wish I had something to spend my attention on
and if somebody could come along and give me something
for free to do, that would be a great deal.
And we've just come to the end of that age there.
(06:34):
There just isn't every chunk of your attention that you
ever want to spend on anything has been taken up.
And in fact, there's increasingly loud clamoring and your phone
badly absorb every second of your brain life. Still though,
I mean, it's possible that sub stack, that the attention
sub stack has taken and I'm happy for it. I
(06:55):
think it's great that writers can make money, and I'm
excited to talk about that. But it's possible that that
has come mostly from not from social media, but rather
from unsocial media. I mean, you literally have people leaving
traditional media places where they are writing columns and starting
to write substacks, right, Like, that's the it's a very
natural kind of adjacency. No, you know, to be honest,
(07:17):
it's almost certainly both. You know, people that had people
that were working as professional writers, right, a lot of
them can go to substack and get a great deal.
That's awesome, we love it. But there's an even bigger
cohort of people who were not professional writers before and
who but for substack, might not have been writing. Either.
Young people who didn't see a path and sort of
(07:39):
you know, might have gone to you know, had something
to give the world as a writer, and without this
model might have had to go to law school like
their parents wanted them to. Or people that work in industry,
or people that have some adjacent thing that you know,
making building an audience and sometimes on substack and sometimes
building a fortune, and who but for substack, would otherwise
(08:00):
not be writing. It's not like they would, you know,
have a job at the Atlantic or something and who
who I have never heard of, who most people have
never heard of, right, which is cool and interesting. I mean,
it's kind of like a smaller YouTube in that way,
right where there's just this vast array of niches that
people can fill. And so I mean I am curious
(08:21):
to that point to get a sense of basically the
distribution of I don't mean the literal email distribution, but
the sort of distribution curve of substacks of the newsletters
people write like, how big a substack? How big a substack?
What have we shared? I think we've shared that we're
over a million paying subscribers, hundreds of thousand of people
(08:43):
who started a substack. I forget what our latest So sorry,
a million paying subscribers and the what is the well,
I guess for that when the average subscription is like
sixty bucks a year ish, yeah, eighty somewhere in there. Okay,
So is that something like eighty million dollars a year
that people are paying not to you, obviously, but to
(09:05):
the writers, of which you get ten percent? Is that
the ballpark way to think about it? Yeah, I mean,
it's it's more than that, but it's that's you know,
that's the right, if I if I ballparked it at
one hundred million for the writers, ten of which goes
to you, would I be not wildly wrong. You're in
the right order, mind, dude. Okay. Um. And then so
within that, like again to your point of like, well,
(09:27):
there's a few famous people, and you know, I'm curious
to know how how the how the distribution works there,
you know, how much are the top people making? And
then like what's the median? Yeah, so the distribution is
super sort of power laws you might expect. So I
think the top ten people make something like twenty or
(09:49):
twenty five million bucks a year between them. Wow, good
for them, they should only live them be Well, yeah,
people were making millions of dollars a year. Individuals are
making millions of dollars a year. Individuals are making millions
of dollars a year, but a very small number. It's
like the Taylor Swift of substack and there's you know,
there's they're actually quite a healthy number people who are
making you know, real money. If you think of real
(10:13):
money is like multiple times which you'd make as a
writer at a publication. I definitely think of that as
real money. But Okay, so your question is like what's
the distribution and the like, tell me about the median person, Like, yes,
there are some superstars, and I am happy for those superstars,
but what's like a normal Like how many people are
(10:33):
making fifty thousand dollars year? Like fifty thousand dollars years?
Like up perfectly, you know that's a that's a living.
And if you can write your own email newsletter and
make fifty thousand dollars a year, that's cool. But how
many of those people are there? I mean it's like hundreds,
I think? Okay, okay, I mean if you're charging five
bucks a month and you can get a thousand, a
(10:54):
couple thousand people to pay you five bucks a month, like,
that's a living, and like a couple thousand people isn't
that many? Right? So? Like, how does that work? Are
there examples of that? Are there? Sort of things you've
found that people have made that work? Are there particularly
interesting niches will have filled? That math is very important
to why substack works. The fact that a relatively small
(11:17):
number of people can chip in five bucks a month
and start to be meaningful. And it's interesting because if
you can get to a thousand, there's usually not a
reason you couldn't get to two thousand or five thousand
or ten thousand over time, and then that's why you
get this sort of power law thing where you have
this upside. But there's lots of things about what it
takes to get there. The thing I think is most
(11:38):
interesting about it, though, is how different the kinds of
things you want to do to get there are from
the things that would that you would do if you
wanted to kind of like maximize your audience to get
ad impressions right all of a sudden, Your incentives if
you want to if you're trying to get your thousand
true fans, your incentive is to create something that a
(12:00):
thousand people deeply value and fall in love with and
want to pay you for and want to keep paying
you for. Right you want to earn and keep the
trust of a thousand people making something they deeply value.
And what that means is that there's if there's something
out there that's like that that a thousand people would
deeply value, but you couldn't necessarily get a million people
(12:22):
to click on it's very very valuable on substack, and
so there's a whole class of very valuable stuff that
otherwise might not get created that can now get created.
And so, I mean the obvious ones that come to
mind are sort of business related, and there have been
you know, industry newsletters have existed for a long time
for this reason, right, There are lots of industry newsletters
that are a thousand dollars per subscription because you know
(12:44):
your work is paying for it. I mean that's one.
Are there kind of less obvious ones, you know, ones
that are more oh less work related? Say, And that
was one of our earliest questions, and we sort of
we wondered this. We're like, well, okay, people if they
can if they can say that it's for their job,
or they can put it on a corporate credit card,
they'll pay for it. But will they really pay for
(13:05):
something else? But pretty quickly we had people doing kind
of like literary comedy and culture writing and politics and
the breadth of topics that it turns out that you
can make on substack is kind of ridiculous. There's somebody
(13:25):
writing reviews of canned fish. I don't know if he's
making a ton of money, but it's like that's the
sort of level of meeting to say, I mean, sure,
it's the internet, Right, so every niche you can imagine,
and then a ton more that you can't imagine are
going to exist. The interesting question to me is what
can you get a thousand people to pay five bucks
a month for? And and maybe more to the point,
like what have you learned about how to do that?
(13:47):
Because I feel like that trick is actually generalizable beyond substack, Right,
that's the basic, you know, minimum viable product. Find your
core customers, make them love you, iterate like, I want
to figure out how to do that better on the
podcast that I make. Right, it's clearly a more mass model,
but still the idea of like making a thing a
(14:07):
few people really love, I think is is really compelling.
And so what have you learned about how to do
that specifically? Yeah, so topic can be almost anything. The
things that really matter are you want to have a
distinct perspective. Exactly what that means depends on what it is,
but you want it to be either a distinct voice
(14:28):
or distinct worldview, or some distinct expertise or distinct sensibility,
something where the thing that the people are paying for
is not the content. Nobody has a problem that nobody
comes to substack and says I wish I could get
more email. I wish I had more things to me.
Nobody has that problem, right. The thing that you pay
for is I need this person's take or this person's thought,
(14:51):
or this person's recommendation, and I want them to curate
a slice of my intellectual life or my attention for me.
I want to delegate some of my worldview building to
this person who I've built up this trust with over time.
And in order to get that to worth paying money for,
you want that to be distinct enough that you're not
(15:15):
you know, you're not giving them something that they could
get in a hundred different places. And you do have
to kind of think about that integrity right being there
if you're curating a slice of their attention, being judicious
about what you're asking them to spend that attention. For
somebody gives you permission to send them emails or gives
you adds you to their podcast player, it's not only
(15:35):
should you send them good stuff, but you kind of
want to not send them things that are not worth
their time or are not interesting. You mentioned you called
it integrity, but the idea of respecting people's time their inbox,
and it reminded me of the fact that not only
is substack subscription based, people pay, you know, to get
(15:56):
a lot of substecks. It's pretty anti AD, right, like,
if you have a substeck, are you even allowed to
put ads in your newsletter? We definitely frown on it.
And this is an interesting point where we are very
anti AD, but we're also very pro freedom. Basically, like,
it's your editorial content. You're allowed to put what you want.
So we've fallen short of saying we're going to police
(16:18):
what you put in your newsletter, provided you're not literally
spamming people, which we take a very dim view of.
But we don't build any AD technology. We don't we're
not sort of encouraging people to sort of have a
hybrid model in general, even though that seems like it
ought to be appealing. We think that focusing on the
other thing actually maximizes the benefits of that thousand true
fans logic, Tell me more, Tell me more about that?
(16:41):
Is that you don't sound on the fence about it.
Has the company been on the fence about it? Could
you imagine becoming more proad. It's something we used to
get a lot from writers and the kind of the
logic is like, hey, subscriptions are money. Advertising is money.
One money plus two money is better than just one money.
Like it's like, wouldn't I make more money? I think
(17:02):
for in the writing world, people have seen enough success
on substack that it's people are starting to get that
the this model is working. And there's there's people who
are in that category of people who are making millions
of dollars a year on substack, who I personally at
the start had to convince to turn on payments. And
I'm like, no, I'm not gonna I'm gonna go do
(17:22):
some sponsorship thing or I'm just gonna grow it and
I'm gonna blow blow. I don't think I can really
make any money, and then I'm gonna just try it.
You know, you have whatever The New Yorker, the Washington
Post very very excellent publications that I pay for with
my own money, and I don't resent them running ads
as well. Yeah, I can. I can see the argument
(17:42):
for that, And I think people can make the argument
for podcasts. You know, I personally, every time I listen
to a podcast and there's a break, that's like, now
let me tell you about something else. I'm like, okay,
they're like coming right at me right now, you're coming
right at I'm not gonna and listen, I don't begrudge it,
but I'm not going to say that I love it. Now,
let me tell you about something else. We'll be back
(18:04):
in a minute to talk about bundling, unbundling and a
problem substack has not yet solved. Now back to the show.
So the first part of my conversation with Chris was
largely about that thousand true fans idea. The next part
(18:25):
of the conversation is about another famous tech saying, this
one is like kind of half joke, half idea, and
it comes from Jim Barksdale, who is a big tech
guy back in the nineties. The key line is this,
there are only two ways to make money in business.
One is to bundle, the other is to unbundle. Like
what do you make of that quote? What do I
make of that quote? I buy it, I think, and
(18:46):
I agree with you that so far subject has been
this big unbundling energy. Right. The fact that as an
individual writer you can go and start your own thing
and make it on your own and get the upside
of what you're doing and sometimes make you ten times
as much money as you've ever made before, and have
a business and all this stuff. That's wonderful. It's a
good thing. I actually think that there's a lot more
(19:08):
energy left in that thing. Um. I think people people
sometimes they're like, well, what's going to happen when people
are getting their eight substack subscription and they're really annoyed
that they have to have so many different substack subscriptions.
And I'm like, you know what, I like, bring on
that problem. I would love to live in the world
where that's your problem. I mean, obviously people that have
in particular would love to live in the world where
that's the problem. Of course, and there's you know, there
(19:32):
are some people who who have that today, there's some
people that are you know, subscribed to a whole bunch
of things, but far and away, I think there's a
ton of energy left in this sort of unbundling phase
of like, I'm a writer, I have something to say,
and I like, I want it to be my thing.
I do think there's an interesting effect where bundle economics
(19:53):
are real, and if we are successful at the grand
unbundling that we are in the middle of doing, at
some point there's this economic potential energy that for unlocking
the surplus of bundle economics for writers and readers, And
there's a bunch of ways you can imagine that happening.
Like one thing that's happening already is that substacks are
(20:13):
turning into companies and institutions, right, people are starting as
one thing and then building a newsroom or building a company.
And the other thing that would be, like the obvious
thing would be like, well, what if you just had
like a Netflix style thing, or like this is what
medium did. It's like, why don't you just have one
a substack subscription and then everything like you know, there's
some magic algorithm that dolls out like who gets the
money based on what? And the problem with that is
(20:36):
that it although it unlocks the bundle economics, it kills
the fundamental magic of what's good about substack, which is
the direct intentional relationship between the reader and the writer. Right, Like,
the whole deal is I'd choose what to spend. I
don't know exactly what the right solution to this is yet,
but my strong intuition is that the right answer is
(20:59):
that you do, in fact want a bundle or bundles
but that it needs to happen bottom up rather than
top down. I think that, you know, as with anything,
the hard part is making it simple. This is one
of the fun things about building products, building good products,
is you like sweat and curse and wring your hands
(21:22):
and pull your hair out for a long time trying
to wrangle a thing. And if you actually do a
good job at the end of it all, you show
somebody and they say, yeah, obviously, yeah, right, you idiot,
Like you spent how long coming up with like an
email newsletter with a website that takes money, you idiot? Like, yeah,
but that's actually good, right, And you're not there yet
(21:44):
for the bundle? Is that is that the upshot? Yeah?
And for the bundle, and we're still in the hard part.
And honestly, there's so much value right now, Like there's
there's so much value in these in the subscriptions as
they exist. And we're already doing a bunch of things
around cross promotion. We let writers recommend each other rather
(22:04):
than having some algorithm that recommends it. So that's another choice,
right In the same way that you're pretty clearly anti
ad you seem pretty clearly anti recommendation. Algorithm, and that
one is maybe more surprising to me because you know,
discovery is hard, and I feel like you must know
a lot about what people read, and if they read
one thing, they like another thing, Like why not make
(22:26):
that kind of you know, collaborative filtering recommendation? Yeah, and
I would add some nuance there, like I don't think
I'm against recommendation algorithms per se, but I think the
specific thing that I'm suspicious of is the thing where
you make an algorithmic surface that you as the reader,
delegate as the control of how you spend your attention
(22:50):
that has some objective that may not be your objective. Well,
now you just turned substack into Twitter, right, That's that's
the straw man version though, or YouTube? Right, Like you
go to YouTube and it's like yea, yeah, you subscribe
to that. But like, don't worry, here's what you really
want to call. You don't have to do that. There's
a way cooler version of it. That's just Hey, lots
of people who read a glace Let's also read Josh Barrow.
(23:11):
You might want to check it out. Like that doesn't
seem like you're trying to steal my mind, like a
social media platform. Yeah, and I think I would argue
that we are doing the cool version of this right.
And the two things that are important to me in
this are, number one, we're not just optimizing for engagement.
We're not saying like, here's what you're going to click on,
and we're saying here's what you might like enough the
(23:31):
one day you would pay for it. And the other
thing is where possible, we'd love to have it be
human powered. Right when you go to read a book,
the fact that an algorithm said to you that it
was the best possible book to you, even if you
could know that was the truth, might be less compelling
than somebody who you've trust and have gotten to know says, hey,
I think you should check this out for these reasons.
(23:52):
And so when you can have things that are that
are you know, incentivized the right way, and when you
can have human beings in the loop, we just think
that that's like a makes for a better experience, and
we've shown that you can make recommendations that people deeply
value that way. What's something you haven't figured out yet, Like,
what's something you're working on now, something maybe you've tried
and it didn't work, like what's a's a what's a
(24:13):
problem you're trying to solve? Now? Okay, I'll tell you
one thing that I'm really fascinated with is when you
get a bunch of people who deeply value this one
writer or this one crazy niche and you find all
the people who are willing to pay five or ten
bucks a month for that thing. Not only have you
(24:34):
given them a piece of media and a connection with
the author they deeply value, You've created You've sort of
crystallized this potential community. The writing and the writer and
the thing you subscribe for is kind of like the
bat signal that draws in the people. But over time
the community ends up being a major piece of why
(24:56):
of the value for people right being among all the
other people who value this enough to pay for it,
not having a bunch of trolls, because you can moderate profitably,
and so I think there's a tremendous amount of fential
energy there. It's something that writers and podcasters really want
from us, And I don't think that we've totally cracked
(25:18):
the answer to it yet, but we've been trying a
bunch of things. Some new stuff is coming up pretty soon.
That's pretty exciting. And I think if we can make
the community aspect of it, right, that will end up
being tremendously powerful. Well, it's interesting because it's like creeping
back towards social media, right, I mean, maybe a better
(25:41):
version of it, but fundamentally that's what you're talking about. Yeah,
I mean it's people talking to each other, people engaging
with ideas, people building relationships. And it's again it's sort
of in this I think of it as an alternate
universe with different laws of physics from the universe where
(26:01):
all of these giant platforms have grown up of the
kind of like massive engagement based AD supported thing, that's
one way to build it. And we're building a kind
of this alternate rails. So what's the thing you're about
to roll out? Am I allowed to talk about this one? Yes?
So we've been working on We've been working on chat.
(26:24):
That's something that you can do on substack chat like
real time, like like Slack style or g chat. Yeah,
you could look at you could think of Slack, you
could think of i RC back in the day. You
can think of Discord is like an amazing thing. Discord
seems like the closest model there is that, right, I
don't know discord that well, but that's a very it's
like a community oriented chat, right, I mean is that
(26:45):
what I should think of for what you're working on? Yeah,
I think closely related. Is it hard? Have you been
trying it and like not quite figuring it out? It's
been working fairly well. I would say we're being We're
trying to be thoughtful about it. Right. The thing we
never want to do again is kind of break the
magic of substack. And in this case, one of the
(27:05):
things that really matters is you want the writer to
be in charge. Right. This is something where I'm if
I have my community, like and this is my little island,
my own private social network. Um, I want to be
in charge of that. It's not I don't want it
to be something that ends up being like and people.
You know, there are substack writers who have tried having
a slack or a discord or one of the telegram right,
people just telling telegram, and it's often just like it
(27:28):
becomes like this source of pain for them. They're like,
oh my god, it's this whole thing and I'm like,
it's not mine and I can't really it's got a
life of its own. It's really get really spammy. You know. Yeah,
it's it's it's hard to make it right. And we're
not trying to make you know to the extent that
we're building. We're not trying to make the best standalone
communication product for any purpose. We're trying to make the
(27:49):
best place to build community and hang out with your
your substack audience and among your substack audience. Um. And
so we've been trying to like make sure that we're
building that with people who are actually doing that, because
this is the fun part about building something like substack,
which in my estimation is like a holy new thing,
(28:10):
is all of the interesting features of it are emergent.
You don't find out until you have the actual people
trying to use them, and then you find out whether
it's working or not. And so we're being pretty thoughtful
and building it with real people and getting their feedback
and making sure it's good. So such Stack is not
that big as a company, right an order of ten
(28:33):
million dollars a year in revenue is very small as
companies go, And yet I've heard a ton about it.
It's gotten a lot of coverage in the media. As
a journalist, I know that journalists love writing about other
journalists and writing about journalism, and I think that's part
of it, right, So you've gotten a lot of coverage
for that. Also, you know, your company has been criticized
(28:55):
for paying certain kinds of writers to come to the platform,
and you know, I'm not interested in relitigating the details
of that, but I'm curious how the sort of two
sides of that have played out. Right, How getting covered
much more than a company your size would get covered
if it weren't basically a media company or a sort
(29:15):
of media adjacent company. How has that been for you?
Have the pluses outweighed the minuses? How do you weigh that? Yeah,
the way that I think of this is that we
you know, substock has an outsize impact on the culture.
People care about it for reasons that are valid and
go beyond the money. We've taken a lot of heat.
(29:35):
We've had people very thrilled at us and very mad
at us, and I've always felt like we can't complain
too much about that. You know, we kind of set
out with these, you know, the two ambitions. But one
of the ambitions is very grandiose, right, It's about making
this new business model for writing and culture. On the
Internet and having that dramatically shape the world and who
(29:58):
people are. And there's just no way that you succeed
at that without, you know, running towards the fire, running
towards the heat of the culture war and the media
and the spotlight and all of the things that people
care about. And so as much as it can be
both thrilling and uncomfortable, I don't feel like we get
to complain. This is kind of what we signed up for,
(30:19):
and all of our paths to success do lead through it.
We'll be back in a minute with the Lightning Round. Okay,
let's get back to the show. We're going to close
with the Lightning Round. There are two names that come
(30:40):
up in the Lightning Round here that I didn't explain
during the interview, but I should have. One name is
Jane Jacobs. She's the author of a book called The
Death and Life of American Cities. The other name is
Matt Levine. He's a finance writer who writes a newsletter
for Bloomberg News. Now let's get to the Lightning Round.
What's the most important lesson you learned from reading Jane Jacobs.
(31:04):
I love the broad impact that's small, practical details of
the spaces we inhabit can have on how we live
our lives. And there's lots of stuff in Jane Jacobs.
It's like that. I don't know if all of it
is well empirically supportive, but there's this fascination with you know,
if you have homes that have windows at street level
(31:27):
and people are looking out, people walking down the street
feel a different way, and it's this very brass tax
like physical aspect of geometry that ends up broadly shaping
people's lives. I think cities are like that, and I
think that the digital places we create are like that too. Okay,
if you could have one person in the world start
writing a substack, who would it be? Might be Matt Levine.
(31:53):
Oh sure, me too. Same You would make so much
money it's absurd. I'm sure he's doing well, but yeah,
it's a good choice. Really really got me with that one.
If everything goes well, what problem will you be trying
to solve in five years? One thing I think about
if we're, you know, successful in all the things we
(32:14):
want to succeed at, this becomes this bigger and bigger
that the GDP of the sub stack of verse gets
gets more and more. You know, we are built on
this foundation of the ideals of a free press, the
ideals that writers should get to like, have their space,
and make what they want. One thing that I could
see being very interesting is as that goes international, having
(32:36):
that collide with various societies where unlike here in the US,
there's not a strong legal and cultural protection for the
idea that people should be allowed to write have ideas
people should be allowed to sign up for it. I
think that's not a free press, right, And it's not
a free press. There's not a free press. Yeah, and
yet on subject there is a free press. And what
does that mean for us that that should be an
(32:57):
interesting problem? Should we earn the right to confront it?
How many subseects do you get? Oh man, hundreds? How
many do you read? How many do you read? Many?
I pay for tens and I read probably at least
all of those ones. I read a lot of substack
to the it's really it's great. I'm an avid user.
I thought you were going to say it's a problem,
(33:18):
but I guess you wouldn't say that. Oh, I love it.
It's a great Everyone should should mimic me in this capacity.
What's one piece of advice you'd give to somebody trying
to solve a hard problem, have a grand science fiction
vision of what you're trying to do, and take one
(33:40):
step at a time. You think you're going to work
on Substack forever could be Is there something that would
like signal to you that it's time to do something else.
If we go to business and they physically have me
removed from the office, I would probably have to consider
my options. Chris Best is the co founder and CEO
(34:07):
of Substack. Today's show was produced by Edith Russolo, edited
by Robert Smith, and engineered by Amanda kay Wong. I'm
Jacob Goldstein, and we'll be back next week with another
episode of What's Your Problem.
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