Welcome to First Time Founders. I'm Ed

Nelson. America's confidence in mass

media is collapsing. Only about a third

say they have any meaningful trust that

major outlets report the news fully and

fairly. And more than a third say they

just don't trust the media at all.

Meanwhile, the people who produce that

content are facing their own crisis.

Across the industry, writers and

journalists are being laid off in waves

as legacy outlets struggle to adapt and

survive. Together, these shifts have

pushed both audiences and creators

toward a new home. Millions of readers

are seeking voices they can trust

directly without an institutional

filtering. And at the same time,

thousands of writers have begun building

independent businesses there. The

platform that I'm talking about has

already drawn more than 35 million

subscribers. and it has expanded beyond

writing into podcasts and video. In the

process, it has reshaped the media

landscape and accelerated the rise of a

new creator-driven era. This is my

conversation with Chris Best, the CEO

and co-founder of Substack. Chris Best,

thank you for joining me on Firsttime

Founders. Good to see you.

>> Thanks for having me. I'm a second time

founder. Does that ruin it?

We we made an exception for you because

we really just want to talk about

Substack.

>> Well, thank you.

>> Um, but we'll get to that. We'll get to

your your story and your career. But I

first want to start with just a factual

statement about America right now. Um,

and that is that trust in media,

whatever media is, is at a record low.

So when you poll Americans, only a third

say they have any meaningful trust that

outlets report the news fully and fairly

and then more than a third say they just

do not trust the media at all. You have

started one of these new media companies

in Substack. What do you make of that

statistic and how does it affect the way

you think about your company? I

definitely think we're in a time of

profound change in media and my model of

this is it's sort of a technologically

driven change. You know, the internet

came along and smashed a lot of the

existing business models for media and

culture and created these massive new

networks that are fantastically

profitable businesses without

necessarily replacing kind of the

economic engine that sustained a lot of

this stuff. And anytime you have a, you

know, in history, if you have a major

sort of revolution in media or

information technology, whether it's the

internet or the television or the

printing press, you often get kind of a

a period of unrest or a period of

destabilization or a a time of cultural

churn as we sort of adapt to the new

reality. And I think we're in one of

those times now. I think we're still

we're still reeling and sorting out the

what happens when you wire the whole

world together into one internet and

layering onto it. Now you can what

happens when anybody can make all kinds

of media with AI when anybody it's sort

of like a we're in the period of

destabilization caused by technological

change. Did you know that that was going

to happen when you started Substack? And

this is I mean really a question of the

origin story of Substack. Was this

something you predicted? And what was

the inspiration behind Substack? This is

why I why I wanted to start Substack.

And in fact, I wasn't setting out to

start a company when we started. Um I

was I was setting out to write an essay.

I was actually on sbatical taking some

time off after my last company. And I

was writing this essay trying to outline

my frustrations with the media economy

on the internet along these lines. And I

felt at the time that it was already

happening. Like I felt, you know, I

could look at, you know, I would talk to

people in 2017 and say, you know, I

think Facebook and Twitter are driving

us crazy and people would kind of go,

"Haha, yeah, but maybe that's right."

But it didn't didn't feel very serious.

Um, and you know, I'd say, I think

people are going to be willing to

connect directly and subscribe to the

voices they trust. And people would say,

"Yeah, maybe I don't know. That's

interesting. probably people will never

pay for somebody. And I think just a lot

of that has proven, you know, to my mind

true. The thing that was sort of like an

interesting curiosity when we started

the company, people are starting to feel

a lot more viscerally now. And this is

why you get these surveys. People are

saying like, I don't I don't know if I

can express exactly what's wrong, but

something is wrong. And I'm hungry for

something better. And I think you can

look at it's easy to be a doomer about

that situation. And it's easy to look at

it and say, "Ah, things are there are

lots of problems and nobody trusts these

things and look at these look at these

negative effects." I think it's also a a

a time of incredible opportunity. I

think it's we're in a moment where

there's going to we're going to be

building the new world. And there's not

going to be we don't get a choice of

whether or not we get change, but we do

get a choice in what kind of change we

get. And that's the thing that motivated

me to work on Substack in the first

place. Before Substack, you started this

company called Kick. You were the

co-founder, you were the CTO. Um, you

later decided to leave that company and

then you, as you say, you ran into

starting Substack. Can you just tell us

like the the brief story of starting

that first company and then actually how

you got Substack off of the ground

following your first company? I was the

technical co-founder, but my my

co-founder Ted Livingston, who was the

CEO, it was really his kind of his baby.

Uh, and I I I sort of stumbled into that

company. I met Ted when we were both in

university and we started working on

Anyway, I won't get too deep into that,

but we we wound up making this messaging

app that got really really big.

Actually, got really big twice. It got

really big and then BlackBerry at the

who was a big player at the time tried

to kill us and almost succeeded and we

built it back up from nothing. got

hundreds of millions of users uh raised

money from 10-centent at a billion

dollar valuation. It was a crazy wild

experience. I learned a lot about

building things that matter. I learned a

lot about how much impact you can have

making technology if you if you do it

well. And I also got this abiding belief

that there's a lot of power and

responsibility in building these kind of

virtual places where people lead

increasingly lead their lives online.

Um, you know, you can't change human

nature.

Uh, it it does exist. People are a

certain way and you shouldn't really try

is maybe what I think. But even so, you

can take the exact same set of people

with the same strengths, the same flaws,

the same beliefs, and depending on how

you set up the rules of the game,

depending on how you set up the space

they inhabit, how you know how it gets

communicated, how it all works, you can

kind of create a heaven or a hell with

the exact same people. Um, and so the

the act of sort of creating these online

worlds, uh, I think is kind of

tremendously powerful. And if you do it

sort of with the conscious aim of making

one that's good for the people that live

in it, you can make something really

great. And that was probably that was

sloshing around in my head. Uh, as I

say, I wasn't after I left, I was taking

some time off. I was just doing all the

things that you don't normally do when

you're running a high growth company,

like see friends and family and read

books and learn to fly airplanes and

indulge hobbies. And I've always been an

avid reader. Um, my, you know, dad's an

English teacher, grew up in a house full

of books, and I've always believed that

what you read matters and the media that

you consume in general matters. It's not

just, you know, people watching this

podcast. It's not just how they spend a

good fraction of their life. And even if

that's all it was, that would be good

enough. But the, you know, the stories

and ideas you put into your head change

you. They shape how you see the world.

They change your experience of your own

life. Uh, you know, what you read and

what you watch changes who you become.

And so, great writing and great culture

is this deeply valuable thing. And so in

my little sbatical time, I was thinking,

I should write. I know how to read. I

know how to type. I have that good sort

of tech bro hubris. I was like, how hard

could it be? I should write an essay.

And that so I started writing that, you

know, that essay that was supposed to be

a originally going to be a blog post or

whatever. I shared it with my friend

Hamish, who's actually a real writer.

Uh, and that was sort of the the origin.

>> There were blogging sites before. People

have written stuff and posted it on the

internet for a long time. Um, what was

the core idea of Substack? Because, you

know, you could go on Blogspot and find

people writing stuff. Um, you could find

people writing stuff online and on the

New York Times. I know it's a slightly

different setup, but what did you see as

different about what Substack was? The

core idea is we're building a new

economic engine for culture.

The problem as as we see it is that is

not you know there as you say there was

already the internet came along and if

you it did one revolutionary thing which

is let anybody publish.

>> Yes.

>> And kind of like unshackle you know

unshackle the media environment from the

gatekeepers.

You know, I like to I say there there

are still gatekeepers, but you can't you

can't keep the people in anymore. You

can't lock people in. You can lock

people out, but you can't lock people

in. But the problem was that there

wasn't, you know, if you were a creative

person, if you were a writer, if you're

a journalist, there wasn't necessarily a

great way to make money doing the work

you believe in.

And if you believe that great media,

great culture is valuable, you want

there to be a way to make money and to

have kind of like a social contract that

lets you do the work you really believe

in. And you know, in the early days

sometimes people would accuse us, they

they'd say to me in an accusatory tone,

they'd say, you know, Substack is just

blogging with a business model. And I'm

like, you know, that sounds pretty good,

right? blogging was this really cool,

you know, there was a there was a golden

age of blogs that was sort of this

intellectual

>> infusion, but it the problem with it was

there wasn't really a a business model

to back it up. It was things got

acquired or things kind of stuffed ads

in in a way that didn't really work. And

so you were missing, you know, if you

were some if you were an ambitious young

person who wanted to had something to

give the world uh and wanted to make

this a career or make this a business,

it was hard to see a way to do it. And

there was sort of the legacy media which

was in decline. And there was kind of

this, you know, this new world of uh

social media which you could potentially

get a big audience but wasn't going to

give you a way to make money doing the

work you believed in.

>> Just to describe the business model of

Substack to to the audience. My

understanding is Substack takes 10% of

the revenue that that the creators

charge when they put up a payw wall. And

in that sense, the real innovation of

Substack to me, to your friend's point,

was the business model. It was to say

blogging can be paid for upfront. It can

be put behind a payw wall. Uh, and an

economy can be created out of that

business model. There will be enough

content, enough creators out there with

good enough content that people will

actually pay for such that this makes

sense as a business. I feel like that

was the innovation that no one seemed to

think would work and yet here we are and

it's working incredibly well and within

just a few years there were half a

million paid subscribers and obviously

that number has grown dramatically

since.

>> Yeah, it's well over 5 million now.

>> Well over 5 million. Would you say that

that is

um that that was the real innovation? It

was the it was you saying actually you

can put this behind a payw wall.

>> The pay wall is maybe not the core of it

but it is it is the economic bargain and

it's look I think when you great

companies in my mind come from the

fusion of a really grand ambitious idea

for the world paired with like a a

modest but achievable first

instantiation of that idea. And the big

idea for this is like look, you can have

a different social contract for media

and culture. The idea that this stuff is

valuable and the idea that, you know,

you should be willing to pay real money

for something that is as meaningful for

your life as, you know, a great essay or

a great podcast or a great book or a

great community or, you know, any of

these things. That's actually a very big

idea. And once that engine starts to go,

this is what you're seeing in the

Substack app. Now the Substack app is

the best place on the internet. It's

still very small compared to you know

the other sort of atcale social networks

but it's you know some of the best and

smartest and most interesting most

creative things are happening there

because of this different economic

model. It's kind of like the there's

like a you know a a social contract and

a philosophy behind it. But at at the

time, you know, when we started, nobody

thought that anybody would ever pay for

anything. I had this parlor trick

because I would describe this idea for

Substack to people and they would say,

"Ah, that sounds nice. It would be cool

if it would be cool if writers got paid,

but you know, no one's ever going to

really pay for something on the

internet. That's not how it works. Like,

I would never." People would tell me, "I

would never pay for some person on the

internet." And my parlor trick was I

would say, "Well, who's your favorite

writer?" And they'd say, you know, so

and so. I'd be like, "Would you pay five

bucks a month for them?" And they would

say, "Well, yeah, for them, for that

person, I would." But that's different

because they're really good. They've

I've grown to trust them. They've got

this. They've got something, you know,

there's something about that person that

they love. They wouldn't do it in the

abstract, but they would do it in the

specific. And that kind of told me,

okay, we're actually at the moment where

this is ready to happen. like it's it's

lots of people doubt that it can happen

but you can actually it can work and you

know we we had sort of like the the very

initial

version of this was you know paid email

newsletters made simple right that's

kind of like the MVP kernel that fully

you know is the is the first full

realization of the big idea that unlocks

for writers

>> and for a long time I think people who

wanted to copy Substack including you

know Twitter and Facebook and lots of

other people they they mistook the thing

that was working about Substack as that

as the the surface level thing. It's

like ah it's you know email newsletters

are the secret or you know this thing is

the secret but it's it is actually the

underlying economic model and the

philosophy that makes it go. When was

the moment that you realized you had

something great? And I I I will just

conjecture

Substack was on my radar during CO. Um I

would hazard a guess that that was the

moment, but when was it for you? There's

a few moments that stand out in my in my

memory, but I'll give you two. And the

first was actually when we launched the

very first customer. There's a piece of

received wisdom that you know among

professional gamblers they tend to have

started out with a big winning streak at

the start of their career. Um and of

course if you think about it for a

second that's not because you know the

reason for that is because people who

start their career as a professional

gambler with a losing streak actually

don't go on to become professional

gamblers. It's just a selection effect.

It's like oh yes that's that's how

that's the origin story of these things.

And I feel a little bit like that

because our first customer was this guy

Bill Bishop who had been writing a new

an email newsletter about, you know, uh,

China for an international business and

government audience for ages. He was

perfect. There was probably like five

people in the world that were the

perfect first customer for Substack and

he was one of them. And he had been

thinking about charging for his work.

He'd been inspired by Ben Thompson, but

he kind of couldn't be, you know, didn't

want to fuss around with all the

technology. So he was sort of this

perfect first customer. And I we like

hacked together the first version uh you

know I built this little website and

plugged it into Stripe and I remember

launching on his first day uh and like

six figures rolled in like within hours

and I was kind of sitting there at my

computer being like I can't like this

seems really good. I can't like I don't

know what I expected but this is way

more than that. And we sort of you know

we had this really big first success out

the gate. uh you know we we got into YC

uh we sort of had this you know this the

very first thing we tried was this

massive success and that gave us a lot

of confidence that we were on to

something even though there was sort of

like you know that was the the the

biggest that was the biggest thing for a

while like it was it was it was there

weren't 20 more Bill Bishops we could go

get at that time uh but we had this it

gave us kind of like the confidence we

were on to thing and then maybe the

second one. Yeah, I think you know COVID

2020 there was a combination of suddenly

everybody has uh a bunch more time and a

bunch more money. And so there was sort

of this great reshift in the economy

where all of the online things or all of

the virtual things got this huge

stimulus and all of the real world

things got this huge setback and

Substack was a really good online thing.

It was you know something really

valuable and meaningful that you could

do on the internet and there was kind of

a it was sort of a fever pitch moment

for some of those tensions with media.

There was a time where a lot of the best

and most interesting independent

thinkers were getting sumearily turfed

to be honest from their perches at

traditional media places. Um you know

Barry Weiss was was you know pushed

pushed to resign from the New York Times

in that time. There was like there was a

whole bunch of people uh that were

fantastic on Substack. The way that

everyone moved away from these

traditional outlets was pretty

incredible. I think Barry Weiss is is a

good example of that.

>> Moved away. A lot of them were a lot of

them were pushed out.

>> Literally pushed out. You said something

there as well that the amount of money

that people had in their pockets likely

because of stimulus. And then also

people are not spending on concerts and

they're not spending on going out to

bars anymore. Like people were

relatively richer during CO than than

they are now or than they were before.

um would make you think that Substack

was a COVID blip. And we saw this with a

lot of businesses, that they only really

made sense during COVID because of the

way the world worked during CO. But

that's not what happened. Substack was a

co phenomenon that maintained its

momentum and has only grown since.

How did that happen? What what is going

on there? I mean, how do we explain

that? Um, just looking back through the

history of this business,

>> we have this story about what's

happening in the world and how it could

be better

and that story is not about COVID or

stimulus, right? It's about this the

evolving media landscape and information

landscape we all live in, right? These

big mega trends. You know, one version

of this is I used to, you know, I think

that before the internet, when I was a

kid, a real problem you could have is

you could get bored. You could be

sitting around and thinking, gee, I have

nothing to spend my attention on right

now. And if somebody could give me

something free to distract me, that

would be a really, really good deal

because I'm just sitting here staring at

a wall or like, you know, I could I

could read a book or play chess with

somebody or turn the TV on maybe. Um,

and then you know, so the early

generation of the internet kind of was a

land grab for all of that attention. And

the bargain was here's something that

you can spend some attention on for free

that is kind of fun and we'll stop you

from being bored. And we solved I think

we solved boredom. You know, there's no

second of your life where you have to

not be looking at or thinking about

something interesting now if you don't

want to. M

>> um but that meant that now now we live

in a world where your attention is

actually your last your your scarcest

most valuable resource.

>> It's literally your life,

>> right? It's literally the things that

you're putting into your mind. It's it's

how you're spending your days. It's who

you're becoming. And so

if there's a way that you could spend

that on something that you value more

and that helps you become who you want

to become more, that has newly become

incredibly valuable. And if there's an

economic engine and a social contract

and a set of technology that can unlock

you to spend your limited time on this

earth, you know, paying attention to

things that you actually value and

becoming who you want to become. And for

a creative person, if you can do the

work you actually believe in, if you can

make something that you think is great

and make money from it, that's the real

underlying value. And that that story is

true and important. And the fact that,

you know, the co sort of accelerated and

threw some gas on it for a while, it

wasn't something that only started to

work because of that. And it wasn't

something that stopped working once that

ended.

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podcast.

We're back with first-time founders.

After co by around 2022, you you start

to incorporate other features beyond

just writing. Um you start experimenting

with video, you start experimenting with

micro blogging. you call it notes and

people generally understand these as

tweets or

uh posts.

So it it almost becomes a form of social

media and it seems that it is kind of

trending in that direction.

Um do you think of substack as social

media? I think it's fair to describe it

that way. I I think of it as what should

come after social media. Um but I think

that that you know we are making that

thing and the the the you know notes and

the Substack app the reason this matters

is because we sort of realized at a

certain point hey Substack is giving you

as a as a writer or creator these tools

to you know connect directly with your

audience and to make money and to do the

thing and that if you're somebody who

already has a huge following you can

kind of you know pull that audience and

bring it to Substack and that's really

good and now you're set up in this

wonderful way. But if you are somebody

who aspires to do that, the most

important thing is how do you grow? How

do you find an audience? How do people

get a chance to fall in love with you in

the first place so that they realize

they might want to pay? This is why like

the payw wall is like the last thing. A

lot of people who are very successful on

Substack pay wall very little. It's

really about, hey, am I making something

that actually reaches people that they

find deeply valuable? And the way that

it was working was that the way that

writers and creators on Substack would

grow is they had to go to all the other

social media platforms. And that's a

problem for two reasons. One is because

now you're still downstream from the

incentives on those platforms. Right? If

we're saying, "Hey, we want to create a

an alternative to the attention economy,

but if you want to participate in it,

you still have to be really really good

at Twitter." Um, there's a contradiction

there. And the other thing is that you

know those other platforms don't

necessarily want you to be able to

connect directly with your audience and

take them with you

>> right if you know we got in a big spat

with Elon around the launch of notes and

he briefly banned mentioning the word

Substack and crushed the links but other

like even you know Mark Zuckerberg spent

five years mad about the sort of fallout

from the Cambridge Analytica thing and

sort of you know turned heavily turned

down the dial of politics on Facebook

and that's, you know, that's a fair

thing to do. But if you're a political

journalist who wants to grow on

Facebook, that's really tough for you.

And so there's all of these other

networks that these that creators,

writers depend on. We want them to be

able to use them to their maximum. But

unless there's one place that actually

shares their interest and makes money

when they make money and believes in

their success and thinks that they

should own their connection to their

audience, like if we could create a

place like that, that would add so much

value that would, you know, and that

would start to become this this place on

the internet where you could go and

choose to take back your mind, choose

to, you know, spend your time on the

stuff that you actually you actually

value and find interesting rather than

just the things that distract

I would say it's an obviously valuable

thing to do and a really hard thing to

do and it actually took us a few years

to get it going. Um, and there was a lot

of, you know, we we built this app and

we experimented with all this stuff and

we kind of eventually got it to the

place now where it's, you know, it's the

right balance of there's short form, you

know, discussion stuff flying around,

there's long form stuff in there. Those

two things like feed off and drive each

other and it's a really good experience.

It's such an interesting paradox of

media what you're describing there where

we prefer the incentives of the payw

wall and the subscription process

because it seems to just lean in favor

of quality. It's like if you like the

what this person is putting out then

you'll pay for it and it and it and it

incentivizes the creator and the writer

to put good stuff out there that people

want to pay for. Then social media comes

along or I guess and and I mean this has

existed for longer than just social

media but social media really

turbocharged the ad model which

basically said it's not really about the

quality of the work you put out. It's

about how much it can attract attention.

So can you be extremely rage baity? Can

you make people feel something

aggressive? Can you say something with a

really catchy and provocative headline?

Um, can you are you willing to put

sexual content out there? Are you

willing to uh sell sex as much as we're

seeing on Twitter and other platforms?

All of these things that grab attention

but are not optimized for quality, which

is why social media has become the

hellscape that it that I believe it is.

And we'll get into whether you you agree

with that, too. But you run into the

problem as a creator where and you're

experiencing this with Substack. Putting

things behind a payw wall does not get

the message out there. It makes it

harder to grow your audience. And so you

are now facing that. Hence why you are

implementing these more social media

minded tools such as video, such as

notes, which is very similar to Twitter.

And there's a sense in which Substack is

kind of becoming the thing that maybe it

wasn't supposed to be. How do you think

about that? I mean, separate video, by

the way. I mean, this is we're on video

right now. This is an interesting long

form conversation. You know, maybe there

will be clips of it that are part of a

short form feed.

>> We're going to clip you up saying very

different things.

>> Yeah. Make me say something

embarrassing. I can do that on my own.

Actually, the Elon part. We'll we'll

clip that. Here's how I would think of

this is what you actually want is a

balance, right? You know, I think of

some of the short form stuff, some of

the jokes, some of the whatever. Some of

that stuff is is I think of it as you

can think of it as fun, right? And if

you take a social media machine and

you're kind of like dial the fun up to

10 million at the expense of everything

else, yeah, you can get something that's

distorted. you can get something that

kind of becomes this this drug this

hellscape you that that is a real thing

that can happen but the solution to that

is not to become anti- fun right you

know we don't want Substack to be the

eat your vegetables platform right if if

if I said hey you know and it's not even

a payw wall thing actually the payw wall

is a different question you know even

for people who are paywalling stuff we

say take your most accessible stuff put

it outside the payw wall that's how you

grow but even just you know if the only

thing I ever do is write 10,000word

treatises that if you really get into

it, it's the most valuable thing in your

life. Um, but it's sort of hard to get

into.

That's a hard thing to kind of like get

people into because how do they find out

about it? How do they, you know, people

aren't always looking to to dive into

something deep like people, you want to

give something to people that actually

can be fun, can be light, but then is

helping you get into something that you

deeply value and helping you discover

something you deeply value. Those things

have to work together. This is why

Twitter in its heyday was so great was

you did have this light, fun, quick

discussion, the quick interesting, fresh

stuff, but then people would be talking

about real things. you'd have long form

articles, you'd have things that were

happening in the world. And I think you

can you can create something much more

powerful if you put those things

together and keep them in balance. So,

it's not a question of you can never

have something that's fun or engaging or

sensational, but that's just that's one

part of the mix. Like, if you're cooking

food, you don't want to say, "Hey, make

the the most bland, purely healthy, you

know, keep you alive subsistence slop."

And you don't want to say just sit there

and eat cotton candy by the handful.

It's like you want a balanced meal. You

want something that's solid and healthy

but tastes good. Like that's that's how

I think about it.

>> Yeah. Earlier you were mentioning I mean

when you started kick and then going on

to Substack, you were talking about how

you learned about setting the rules of

the game. You learned about human

behavior. You learned about how social

networks develop and how people interact

and that it's all about setting the

rules of the game. And you said that

setting those rules is the difference

between heaven and hell. And I think

that that's probably quite true. We've

seen platforms where the rules of the

game have been set up such that they do

turn into hell in a lot of ways. And

hell might be very profitable, but few

people would disagree with that

statement when it comes to probably uh I

mean certainly we'd say 4chan maybe

maybe you'd say X, maybe you'd say

Instagram. It has certainly has some

hellish qualities um to it. I guess the

question with Substack because Substack

I think I would agree with you is more

of a heavenly space in the sense that

there's higher it's operating on a on a

on a higher level of quality. It's more

civil. It's more respectful. There's a

level of fun that is being had. Uh but

it's not it doesn't feel like the

hellscape ragebait center that I think a

lot of other other social media

platforms are.

>> Thank you. That means a lot.

>> I'm glad. And I guess the question

being,

is that because the people on Substack

are different or is it because of the

rules of the game? Because they seem to

be two different things. The people who

are on Substack are generally writers,

people who are interested in putting

thoughtful content out there, but maybe

there's something about the way you

built the product and the way you set

the rules that facilitated that.

>> Those things are related, by the way.

>> Yeah. like these things, you know, these

things develop a culture and a momentum

of their own. People are not immutable.

They, you know, they in culture to a to

a space they're in. And when I say the

rules, what I'm I'm talking I'm not

talking about like, you know, what's the

moderation policy or what's the, you

know, terms of service or something. I'm

talking about something a little bit

deeper. I'm talking about kind of the

underlying

uh the underlying game, the underlying

economic incentives.

>> Okay? If you're uh a social media

platform who makes all of your money

from uh you know a superefficient

platform level ad exchange and your

business model is essentially

aggregating attention and then selling

it as a commodity to the highest bidder.

you've built a system where you can, you

know, if I'm that platform, I can value

your time, but I can't really value what

you value or at least that's not part of

my economic equation.

And so if I am if I go then build a

let's say a feed algorithm and I'm

running experiments and I'm trying to

say, hey, what's you know, how do I want

this to work? What's going to be good?

What's going to be bad? You know, how do

I make my business successful?

I'm gonna optimize for how can I get as

much of your time as possible

kind of regardless of how much you value

it. Like I I might say, "Hey, I want you

not to regret the time you spent." But

in terms of raw economic reality,

>> it's your time that matters,

>> right? When you take that equation and

you kind of like do the things that

actually optimize that business, you end

up pulling in these directions that

create these, you know, hellish is

probably the is the extreme way to put

it, but these, you know, these traps,

these these these negative sort of

spirals as a consequence of the

underlying business model and the

economic incentive. It's not because the

people are bad. And you know, you you

might even put in rules or you might

even put in systems to try to like

mitigate that. You might say, "Oh, I

want to dial down some of this problem

or I want to do this thing to make

people feel better." But you you've got

this underlying problem where the the

economic incentive that drives your

business is pulling in a way that is at

odds with the human beings who are using

the platform you make. And so the

approach we've tried to take at

Substack, and once you're in that

position, it's impossible either way, I

think, right? Like if you say, "Hey,

making a great product, you know, great

in this in this developed multiplayer

way or be a successful business,"

there's no good choice there because,

you know, even if you choose to make a

great product at the expense of being a

successful business now, you're not

going to like you're not going to

matter. You're not going to be able to

grow and and make the thing.

>> Um, and so the underlying theory of

Substack is look, let's try to align

these things better. We're going to set

up a situation where people are, you

know, people are only going to pay for

stuff on Substack if they actually care

about it and value it. And then we as a

platform are only going to make money

when the writers and creators make

money. We take, this is why we take a a

percentage fee. Um, because it's like

for every dollar Substack makes, the

creators make nine, right? It's it's we

can literally only succeed as a business

if we are helping people make money, do

the work they believe in, and then those

people can only make money if they're if

they're making something that's really

good enough that, you know, people are

are choosing to pay for it. And so, you

know, when we, you know, we still have a

short form content, we still have a feed

with an algorithm, but when we run an

experiment and we're we're asking like,

how do we make this algorithm better? If

we run a test that says, "Hey, we got

people to spend more time and scroll

more and see more things such that if

you were serving ads, they would have

seen more of them, but they read less or

they spent less time watching a long

form thing." Uh,

for us, that's a loser because we know

that finding you something that you

deeply value is is the way to get you to

fall in love with it that you might pay.

And so the kind of like the underlying

economic incentive that we've created to

pull this platform forward pulls us in

the direction we want to go and makes us

kind of yokes us to having to serve the

actual people who are using it. Another

thing we do that's like this is is you

know letting people export their

audiences, right? The fact that a

subscription on Substack is an email

subscription. You get the email address.

You can bring your subscribers from

somewhere else. You can take your

subscribers with you when you leave. At

the surface level that might you might

say, "Oh, that's bad because you're not

locking in your customers and they can,

you know, you're giving them the option

to leave." But what it actually does is

it means that because you know you can

leave, you can trust Substack. You can

come here and you know that you know the

only reason people you're going to stay

is that we're giving you enough value

and we're making something that's

actually good. We're not trying to lock

you in. And that sort of

counterintuitively

means that people can invest and trust

the platform. I asked you earlier is

Substack a social media platform and you

said yes but that it's the thing after

social media. Is the ultimate goal of

Substack would you say in your mind if

all things go to plan? Does it replace

Instagram and Twitter and Facebook and

the large social media platforms? I

don't know if it wholesale replaces it.

You know, I think there are there are

things about each of the the the

platforms that are valuable and there

are things that we're not trying to

replicate. You know, I something I tell

the team is like, you know, we're not

we're not going to out tick tock Tik Tok

and we shouldn't try, right? Like we're

not we're trying to do something that's

fundamentally different than that. Um,

and so I wouldn't say that we're, you

know, if if Substack is maximally

successful, therefore there's no

Instagram anymore or therefore there's

no X anymore or anything like that.

The way that I think of it is

I don't know if you've ever there's

there's there's this woman Katherine D

who writes on Substack who talks about

the the internet as fairyland or the

internet as the astral plane, the

internet as this kind of otherworldly

place that people can go and that you

know that that touches real life but is

not quite the same and that you can risk

bringing bad things back from. There's

sort of a it's a it's a it's kind of a

place it's a place where people are

spending more and more of their life and

they're leading more and more of their

life. They're they're having the you

know it's the world of ideas. It's the

world of media. I I kind of think of it

as you know it used to be that the

internet was not real life. Then the

internet the internet became real life.

The third step is real life is the

internet.

what happens on the internet starts to

to reach back out and reshape our world.

And I think of Substack as like a place

on the internet. Substack is like a city

in the astral plane of the internet. And

it has these properties, right? It's a

place where you can uh you you can be

free and independent, right? You can you

can own your plot of land. You can start

your business. You can have your, you

know, your own space in this in this

great city and you can do it as you, you

know, do with it as you see fit. You can

have creative freedom. You can do the

work you really believe in. You know,

you can make this culture. And then

there's sort of like a, you know,

the more and more time people are like

putting their time and energy and money

and creative efforts and attention into

this this kind of city that works in a

different way. It's creating culture.

It's creating a real alternative to some

of the other ways that people feel

online where a lot of the places people

spend their time online, I think, just

feel like, you know, a slot machine or

feel like going to a casino or feel like

kind of plugging into a drug and and

just sort of stepping away from their

life. If you're not going to if you

sorry if you're not going to out tick

tock Tik Tok though are you essentially

yielding that t and we can go with the

city analogy too that Tik Tok will

always be a larger city than Substack

because for all of its vices it's the

most addictive. I mean larger larger in

what way? I mean there's in population

in users maybe in population probably

maybe in time spent uh in economic

value. I don't know about that. Um, you

know, I I I wrote this piece called the

two futures of media, where I think, and

I think this ties into kind of like the

AI world, where one view of media is to

view it as a as a drug, basically. It's

like, hey, media, the point of media is

how I feel in the moment when I use it,

right? It's an escape. It's a it's a

it's a thing that I do to just like

change my current feeling or mental

state. And I think that that thing is

very real. It's a real purpose. It's

something that people really want. And

there is like a there is kind of a

natural conclusion of that that pulls

towards you know if you took Tik Tok and

then you said okay well it's all going

to be AI generated so it's even more

compelling and then it's going to be you

know you sort of like naturally pulls

towards wireheading. You know the

science fiction concept of wireheading.

It's basically like what if you could

have a technology that just directly

stimulates the pleasure center of your

brain. It's kind of like a, you know,

like a technological drug that you just

kind of like press and makes you feel

happy. That's going to be real. Like

that's there's going to be there already

is a big segment of the world that wants

that thing and is using that thing and

there's money to be made in creating

that thing and we are not going to

replace that thing. We're not going to

play the same game as that thing. What I

think we can do is we can give people a

real alternative and we can say there is

a different you know you can take back

your mind.

The point of media is not only to get

what you want it's to learn what to

want. It's to participate in culture

with other people. It's to act back on

the world. Uh I think ultim is can be in

the moment less compelling but in the

long run is much more compelling. And I

think there's a flywheel effect where as

more people choose that, as you can kind

of see what happens when people choose

that, and as those people get sort of

richer and better lives, you can create

a real alternative. And I don't think

that it will be necessarily economically

smaller than the bad version.

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We're back with first time founders. I

like describing Substack as a city in a

world of places because it does feel

that that is the way the internet is

evolving. And I as someone who creates

content, I find that each place, each

platform has different characteristics,

different rules, different kinds of

people and different kinds of stuff that

resonates. And I find that I tailor and

I switch my language between each

platform. On LinkedIn, it's more

cordial, more corporate.

>> So grateful for this opportunity

>> on Twitter. It's a little bit more rage

baity.

>> On Twitter, look at this [ __ ] Can

you believe that anybody actually thinks

this?

>> Exactly. And we're all kind of having to

learn how to navigate these languages

and how to tailor our messages based on

which platform or place you are in. What

are the characteristics of Substack? If

Substack is a city,

how who are the people? What are the

qualities of that city? What kind of

language do they speak? So I think it's

intensely cosmopolitan.

We have this, you know, there I I think

of substax sometimes as like a an index

fund of culture, right? There's this it

there's this space for everyone and

whoever you are, your tribe is kind of

there and there's like the good version

of your, you know, your subculture, your

artistic community, your ideology, your

people. And so your thing is is there.

There's a home for you there. And

there's this richness of 10,000 other

tribes, other cultures, other literal

geographies, other topics, other kinds

of people. It's this, you know, you can

have this massive

diversity, intellectual diversity,

cultural, you know, subcultural

diversity, and it can coexist in peace

and people can have their, you know, be

experience these different parts of

themselves and different parts of

culture, uh, in a way that kind of fits

together and doesn't get doesn't get

sort of homogenized into one great

slurry. There's sort of neighborhoods to

Substack, uh, with different feels and

different vibes.

I would say I aspire for it to be sort

of the intellectual and cultural capital

of the internet. I think it'll be I I

think one day it will be at a scale I

don't know if it's literally bigger than

the biggest networks but I think it I I

think there's no reason it can't become

into that echelon in terms of sort of

raw population but I think long before

that happens and even today there's sort

of a sense of you know if you think

about where the journalists where the

writers where the musicians where the

artists where the statesmen where the

poets like all of these kind of like the

intellectual and cultural elite uh can

kind of like create the best versions of

their ideas and thoughts. Increasingly

that is happening on Substack where you

see something really good somewhere else

on the internet, you kind of flip it

over and it says, you know, made in

Substack on the bottom and it becomes

this place where it's like if you want

to if you want to go to like the real

world of ideas, this can be this is like

the home for it. And that's sort of

that's the you know when I that's when I

think of we're not trying to out Tik Tok

Tik Tok, we're trying to like out

Substack. That's the sort of the core of

it. It makes sense to me that that's

where you land on it. That's what it is

to me. There are different places on the

internet and if you want to go to the

intellectual place, that place turns out

to be Substack, which opens up so many

different opportunities I feel like for

your business because the big question

for advertisers is they're all just

trying to figure out what kinds of

people are where and that to me is is a

big deal. I mean, and it goes beyond

just advertising. It's like if we're

trying to figure out what is the economy

of the internet, we need to figure out

what are the different neighborhoods and

what are they actually looking for. And

if you can identify that there is a

giant population of people who identify

as intellectuals, that's value. That's

an audience. That's a group of people

that you can kind of understand and then

you can start to sell products and

services to which to me opens up so many

different opportunities for Zubstack.

Which is why it's interesting how you

guys have developed all of these new

tools like podcasting, video, notes,

like it's more of a social media app.

Now, one thing that you guys are

investing in which I think is the a

great move um because I've been bullish

on this for a while is live streaming.

Tell us about why you're getting into

live streaming. Okay. Okay. The reason

we're getting into video in general um

is because I think that this this medium

is very important and there's you know a

sense in which video has become the

lingua frana of large parts of the

internet and especially you know this

thing we're doing now where you have

sort of a a long form the part that fits

really well with Substack is where you

have sort of a long form thoughtful

conversation where there is like a you

know I think of a long podcast as in

some ways the same kind of thing as like

a long essay.

Right? It's something that takes a bit

of it takes a bit of investment. It can

be a bit challenging. It can be more

deeply, you know, it's literally long

form. Uh you can go deep on ideas. Uh

that thing can be this deeply valuable

uh intellectual thing or cultural thing

or, you know, thing that's fun and

elevated in other ways. And then there's

like this, you know, there's the clip as

the kind of fundamental unit that uh

helps that thing spread. that's like

here's how we can like you know here's

how you can take this thing and reach

out and grow and like show it to people

and have them discover it and give them

like a little hook to go deeper. It's an

important medium on the internet. It's

something that a lot of you know

podcasting and video is something a lot

of writers want to do. A lot of people

who do who want to want to express

themselves in that medium that even

aren't necessarily writers. It's

important. And then live is kind of this

very magical way to do that thing in a

really direct and authentic way. I think

there's kind of going to be this

interesting barbell effect with a lot of

the AI stuff that's happening where it's

kind of like you can make something

that's sort of like maximally

self-consciously unreal

or you want to make something that's

like the most real it could possibly be,

the most human it could possibly be. And

both of those polls are going to be

really good. And then everything in

between is going to be less and less

good. So something that's kind of like,

you know, sort of sort of human but sort

of fake. And just having a like having a

live conversation with somebody is this

really honest earnest thing. It's not

polished. It's not perfect. It's not

even edited yet. If you're literally

watching it live, it becomes this very

direct thing that people can make. And

then we're investing in, you know, the

set of tools. This is the other property

of the city. It's kind of like

technologically advanced. It's giving

people those those tools that are

indistinguishable from magic. Um, you

know, the same way that for a writer on

Substack, you could come and type into

this box.

And if the thing you type is actually

great, which is really hard, um, but if

if you can actually write something

that's worth caring about and worth

reading, that's so valuable, you

shouldn't have to think about anything

else, right? come and type into this box

and if the thing you type is great,

you're going to get rich and famous.

That's kind of like the that's sort of

the the core thing I want to be able to

deliver for people. You shouldn't have

to be a nerd or hire a team of nerds.

You shouldn't have to figure out all

these other things. You should be able

to just create the thing you believe in.

And if you can focus all of your energy

in making it great, then it can, you

know, the the the technology can handle

the rest. I think we're we're going to

be there with video very quickly. And so

part of Substack live is literally

you're doing a live stream, but part of

it is we have this automatic production

stuff that's cutting it into a usable

YouTube video, a usable podcast, long

form podcast thing, a usable set of, you

know, well-chosen, highly like

well-edited clips. And so if you're

somebody that has something to say, you

can kind of show up on Substack and say

it. People can tune in live and it turns

into this sequence of media that can

work. is sort of like doing the grunt

work of taking your magical creation and

turning it in and translating it into

all the usable forms, maybe even

literally translating it. By the way,

we're in a world where Star Trek

translation, it can just be in you in

every language is suddenly possible. Uh,

and so we're kind of pulling the thread

on this vision and I'm very excited

about it. One of my beliefs about media

and the way things are trending right

now is that I feel that most trends can

be kind of reverse engineered to the

fact that Americans and the global

population are just unprecedentedly

lonely right now because of technology.

The fact that we're spending 70% less

time in the past decade with friends,

the value of one in 10 Americans say

they have zero close friends at all. And

what I have found is that the internet

has become sort of the the most visceral

reflection of our craving and our desire

to inter simply interact with other

people. And it seems to me that the most

successful forms of media are the forms

of media that are offering that

interaction up. So if you're watching

CNN, sure you you get to like watch some

people talk on the TV, but you don't get

to talk with them and you don't get to

talk with anyone else about what they're

saying. Whereas, if you go on YouTube,

you get to interact with people in the

comments and talk about what they said,

what was stupid, what was funny, what

was interesting, and then if you're

doing a live stream, you get to interact

watching it live and then comment on it

with other people at the same time. And

it basically feels as though the way

media is headed is just whatever

platform can most realistically

uh replicate the experience of just

living like just interacting with other

people just like being actually in a

conversation and if you can replicate

that on a digital platform then you have

a win. Do you think that's right?

There's a big core of truth there. I

think people are lonely. I think the way

that you get to interact with others,

the way that you get to be a part of and

act back on the community, the world of

ideas is very important. I think yeah,

places the aspiration I would have for

Substack is twofold here. The first is

what you're saying. Yes. I think the the

you know there's these communities when

you have these like within the city you

have like the space each Substack has

its own world. There's its own kind of

community with walls. It has its own

identity, its own world. and that like

comment section, people make friends

there. People get to know each other,

you know, people

>> become friends in real life because of

somebody they met in the blog comments.

Like that's a the thing that

increasingly happens. And so I think,

you know, part of it is yeah, creating

the part of the digital world that

actually lets you live and interact in a

human way and doesn't reduce you to a

passive consumer, but lets you be part

of a community and act back. That's

really important. I also think, you

know, that third phase like the internet

becomes real life, right? I've been to

meetups that Substackers have and you'll

have somebody that's that's a, you know,

a blogger and they show up at a bar in

San Francisco and there's a hundred

people there treating them like a

[ __ ] rockar and you have this like

this real set of people that have formed

around this shared idea or interest or

community. you know, the the the places

where the internet can then spill back

into actual real life, where it's not

only a substitute for seeing people in

person, but can cause you to see people

in person. I think that's really

important and valuable, too. People,

specifically young people, are reading

less than ever before. No one really

reads among Gen Z at least. Um, and

actually young people are getting

stupider. So, um, math scores are in

decline basically since we put computers

in our pockets. Literacy rates are going

down. Um, young people are literally

getting stupid from the amount of time

that they're spending on Tik Tok,

watching YouTube, watching reals, etc.

Like, our brains are actually

atrophying.

Do you think that Substack

could help offer a solution to this

problem? I do and I do think the problem

is real. I think it's easy to overstate

it. I think there's sort of a sense in

which every, you know, every generation

turns around and says kids these days

are failing in these ways and they're

rotting their brains. And you know, I

think you could have said that about TV

when for my generation, the generation

before and it was probably true to some

extent. You know, the way I look at it

is we're not going to turn back the

clock on these things. you, we're not

going to put the toothpaste back in the

tube and not have the internet anymore

or not have phones anymore or not have

networks that connect everyone anymore.

I think even if you could do that, you

you shouldn't want to. And the question

becomes, you know, what's the version of

using this stuff that's actually good?

What's the version of it that's not just

compelling in the moment, but is

actually helping me live the life I want

to lead, become the person I want to

become, you know, help create the

community and the society I want. And I

think that hunger is there. I think

young people want that as much as ever.

And one of the things that you can do to

help to help is to to create a real

alternative and to say like, you know,

I'm not I'm not saying stop scrolling

TikTok, but sometimes try this other

thing. Sometimes come watch this long

form thing or be part of this comment

section that's going deep on something

or or, you know, read a read a short

blog post. Um, I do think people are

hungry for that stuff and if you bring

it in a way that's

good and new and authentic, it works.

Chris Best is the CEO and co-founder of

Substack. Chris, really appreciate your

time. Thank you.

>> Thanks for having me.

>> Thank you for listening to Firsttime

Founders from Prof Media. We will see

you next month with another founder

story.