0:00

We say, you know what? What if Alex

0:02

pitches? And Austin walks around with,

0:04

like, a printed out, like, cell document, basically.

0:06

And basically stares people in the eyes

0:08

until you they give you your email, and that's

0:11

what we

0:11

did. So I would I would spend time door

0:13

to door sales. So you would love a newsletter

0:15

list. I like it. I would walk around the

0:17

the the big lecture

0:20

hall, five hundred people, and I kind of stand

0:22

there. Give me your email. Give me your email. And

0:24

and you get big on him, like, did you pop

0:26

your chest up in Canada too? Yeah. You would look into

0:28

the song. Your email. If I,

0:30

at the time, if I spoke in front of five hundred

0:33

people, I was getting five hundred emails.

0:35

Yeah. Because I you know, there's whole classic thing like,

0:37

you know, the number two fear in life is

0:39

a public speaking, and number one is is or number

0:41

one is probably speaking to his death, like, you'll rather

0:43

be in the in the casket than speaking at the

0:45

the ULEG. That was me at the time. And so

0:47

I was like, well, if I'm gonna do this, I

0:50

need. Those emails. What's

0:52

up everyone? I'm Alex Lieberman. And

0:54

I'm Sofia Amaruzo. Yo. This

0:57

is Jesse Fuji. And this

0:59

is the crazy ones. What's

1:03

up, everyone? This is Alex Lee Ramin Cofounders

1:05

and chairman of Morning Brew, and we were back

1:08

with another episode of The Crazy Ones,

1:10

The Best Startup Show on Planet Earth.

1:13

We're trying something a little bit different today.

1:15

My cohost, Jesse, and Sophia

1:17

are on a well deserved break

1:19

at the end of the year. And so if you're

1:21

listening to or watching this episode, I believe

1:24

it is January third. So wishing you

1:26

a happy New Year and a ton of good

1:28

things to come. So here's what we're trying

1:30

today. My Austin

1:33

and I have talked about the Morning Brew story

1:35

at length on other podcasts,

1:37

but very rarely. I don't even know

1:40

if ever have we talked about our story

1:42

together in a moderated

1:44

conversation. And so that's what we're gonna

1:46

be doing. We're gonna be talking about the journey

1:48

of Morning Brew, the idea, the challenges,

1:50

the wins, what comes after the brew,

1:52

what the business is like now, the future of media.

1:55

And to have us have this conversation

1:57

is our good friend, Sahel Blum, Sahil

2:00

is an investor. He's a writer.

2:02

He's a prolific Twitter. He

2:04

has done all of the

2:05

things, and so we're so lucky to be joined by him

2:07

today. So I'm gonna pass the mic to you. Awesome.

2:09

Well, thank you guys so much for having me. I'm excited to

2:11

get to do this. I'm gonna set one

2:13

ground rule at the outset of this, which is

2:15

no p our bullshit responses to

2:17

anything that goes on. So that's the only

2:19

ground

2:20

rule. And other than that, I think we can kick it right

2:22

off, but excited to excited to be here.

2:24

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at healthcare brew dot com.

2:53

You

2:55

know, I wanna start with something that you

2:57

guys both tweeted just recently the other day,

2:59

which was a screenshot. I think Austin, you

3:01

tweeted it first. It was a screenshot of

3:03

an email. With names blacked

3:05

out. So I'm not gonna ask you who

3:07

who actually said it. It'll be in the show notes and

3:09

we'll share it. But basically, it was a

3:11

rejection email from presumably an

3:13

investor criticizing

3:16

a few factors about the morning

3:18

brew, in particular, criticizing

3:20

whether or not it was ever gonna be able to make any money,

3:22

any revenue. And what you tweeted was basically

3:25

like, look, if we had listened to these people

3:27

that were doubters of the idea, we wouldn't

3:29

be where we're sitting today. So I wanna

3:31

start there. What's going through your head

3:33

when you guys are receiving presumably a

3:35

bunch of emails like this back in twenty

3:37

fifteen? Yeah. I can start.

3:39

So in twenty fifteen, Morning

3:42

Brew wasn't a business. Right? It was a

3:45

a side project, a hobby, a

3:47

fun thing just to stay up stay

3:49

in the business world for ourselves and help our

3:51

friends. And one thing

3:53

I remember in the early days is I was actually pretty

3:55

surprised about And and

3:57

now I look back and I think it's awesome. It was how

4:00

relentless Alec was about

4:02

getting in touch with everyone. Right? Talking

4:04

to people, meeting people, whether it was advertisers,

4:06

investors, whatever. And Alex, I mean,

4:08

it's a professor in Michigan in the email.

4:10

And Alex emailed the professor and

4:12

most people had pretty good answers.

4:14

Most people and we sat

4:17

down with most people in Michigan in the entrepreneurship

4:19

clubs and and whatever. And we sent

4:21

this email. And we had heard that

4:23

this guy, this professor, was a

4:25

little abrasive.

4:27

And we definitely didn't expect to

4:29

get that email. I don't blame

4:31

him by the way. Like, I think at the time,

4:33

we also didn't think it was a business or at least not

4:35

a potential big business. So I

4:37

I don't blame him, but that

4:40

was only fuel to the fire. Do you

4:42

remember it being fuel at the time,

4:43

though, or was it just like a blow?

4:46

Yeah. I mean, it's easy to call it

4:48

fuel and hindsight. You know, like, these type of things are easy

4:50

to say, like, oh, yeah, I knew I was gonna keep grinding

4:52

whatever. Like, Alexis Ohanian has his

4:54

with being called a rounding error by the Yahoo

4:56

team. This is kind of your moment of that.

4:58

Was it fuel at the time? It's so hard to know

5:00

how much is actually, like, revisionist

5:02

history, like, even when we

5:04

tell the original story of Morning Brew

5:06

and how it started, like the original

5:08

insight, I oftentimes will ask

5:10

myself question is like that the original

5:12

story. Right? Because we've told it so

5:14

many times now that I forgot there's

5:17

there's some kind of principle

5:19

where it's like if you tell a false

5:21

truth, enough times that becomes the

5:23

truth. And so, like, I can't

5:25

remember actually what the thought was.

5:28

In late twenty fourteen when

5:30

I started writing this thing and when Austin

5:32

joined

5:32

on. And so I

5:35

would say for me,

5:37

actually, there was

5:38

probably some fuel from people saying

5:41

no. And by the way, this teacher we're

5:44

definitely not just picking on this teacher because

5:46

actually Alexis Ohanian, he had replied

5:48

to Austin Sweden, basically, was like,

5:50

I really like constructive rejections,

5:53

which I totally agree with. Like, this this

5:55

teacher was not

5:58

a dick in the tweet like he was constructive. He

6:00

gave reasons for why he

6:02

wouldn't invest. For me, actually, when we

6:04

were fundraising, the worst thing was

6:07

like family and friends or people

6:10

peripheral that would just string

6:12

along these conversations and be like

6:14

three months of them saying, hey, I'm gonna

6:16

look at the materials tomorrow. Hey, I have

6:18

this question. They would have you answer all these questions.

6:20

And then after three months, tell you that didn't

6:22

want to invest. Like, that was the worst.

6:24

But yeah, it was this teacher. I remember

6:26

Mark Cuban. We also asked him to invest.

6:29

And I give so

6:31

much props to Mark because

6:33

he is someone that irrespective of his

6:35

success, he still emails

6:37

with founders at the earliest stages

6:39

all the time. But basically, he had a similar

6:41

response to this teacher where he was like, there

6:43

are a ton of newsletters. I don't get the

6:45

difference. What's the differentiator? That was

6:47

the gist of what he said. I

6:50

think that was the fuel for me. Actually, I

6:52

think a fair bit

6:54

of the fuel was people

6:58

who I think doubted

7:01

me or belittled me throughout,

7:03

like, middle school and high school. And

7:05

I felt a chip on my shoulder from that

7:07

for sure. And then I think a piece of it also

7:09

was just like, you know, you

7:11

guys know this, but I lost my

7:13

dad actually right before the brew

7:15

started. A week before

7:17

junior year of college, the brew started

7:19

first semester senior year at Michigan.

7:21

And so there was I would say that was actually

7:23

the number one driver was this

7:25

kind of just focus to

7:29

create something of value. So kind of

7:31

the Lieberman household wouldn't have to

7:33

worry again because that was actually probably

7:35

the number one anxiety that was

7:37

taking up space in my brain. I don't

7:39

think I knew that the timing

7:41

connection between between your father passing

7:43

away and the starting of the brew, which is a

7:45

really interesting insight. Were

7:48

you, like, an entrepreneurial kid? Like,

7:50

prior to your your father passing away, do you had

7:52

you always thought you were gonna start something and go

7:54

build something? Or do you think that would ended up being spark of

7:56

wanting to go create something with your name attached to

7:58

it. Yeah. It's funny. Like, now I couldn't

8:00

envision doing anything but this.

8:04

But no, growing up, all I

8:06

could think about doing was being a traitor on

8:08

Wall Rief. And -- Oh. -- and

8:11

and That's so strange. And

8:13

and the reason was, again, that's what my

8:15

parents did. So it wasn't like me thinking

8:17

on behalf of myself and what I knew I

8:19

enjoyed versus didn't enjoy. It was just like,

8:21

My dad's a trader. That's what he does. My

8:23

mom's a salesperson at a bank. That's

8:25

what she does. I just wanna be like them.

8:27

Mhmm. And so I actually thought it was the opposite

8:30

of independent than he was dependent thinking for my

8:32

whole life. I was for

8:34

sure creative growing up. Like, I remember

8:36

as early as like first or

8:38

second grade. This is like the smallest thing,

8:40

but I remember wanting

8:42

to create a

8:45

pen highlighter combo. They didn't sell

8:47

those at the time. Mhmm. So I snipped a

8:49

pen in half and I snipped a highlighter in

8:51

half. I taped them in the middle. And so I

8:53

could both write notes and

8:55

highlight with the same instrument.

8:57

And then at sleep wake camp, I

8:59

had a a shoe shining business.

9:01

So like I like tinkering, but

9:03

no, I never had the thought like I'm gonna go

9:05

start my own business. You know, like my co

9:07

host for the crazy ones, Jesse Pucci,

9:09

like his dad's an entrepreneur with

9:11

a travel

9:11

agency, he always knew he was gonna start something

9:14

that wasn't me. What about

9:15

you, Austin? So I grew up in

9:17

the suburbs of Baltimore and no

9:19

one who I knew No one's parents

9:21

were in finance. Like, I knew no Morgan

9:23

Stanley or Goldman Sachs were growing

9:25

up. But with this very small

9:27

private school, and so I wanted the exact

9:29

opposite when I went to college. So I went to Michigan.

9:31

I think you were similar, similar private

9:33

school. And from that moment

9:35

on, I was like, oh, all the the kids who

9:37

look like me and sound like me are

9:39

all going to investment banking. Like, that

9:41

was the thing at Michigan. And so

9:43

I kind of followed the the herd. That was

9:45

a

9:45

sheep. Just following that. Was it like a fraternity thing? Like,

9:47

I mean, were you were you guys in fraternities

9:49

and, like, they had a pipeline to Wall Street Rief

9:51

was it just all your Rief, people? I

9:53

mean, it was it was a frat but business school

9:56

thing. Okay. Right? Like, if you're in the business school,

9:58

goal number one, work at

10:00

investment bank. Mhmm. Goal number two,

10:02

If you can't do that or you're really

10:04

crazy, go work at McKinsey. Like, that's

10:06

really unique. That's really different.

10:08

And scrape in the bottom of the bear, at old

10:10

McKinsey. Exactly. So so that was like that

10:12

that was that was the goal. But I think

10:14

looking back in hindsight, like,

10:16

looking at my parents even, they're

10:18

both entrepreneurs, just not in the

10:21

the sense that we think today. Right? They're not

10:23

Internet entrepreneurs. My mom was a dentist

10:25

and she's owned her own dental practice for twenty

10:27

years now. And so, you know, she's a business

10:29

owner. Right? So the people I aspired

10:31

to were small business owners. I

10:33

mean, small as relative. Right? There were some very wealthy

10:35

people in Baltimore, but you

10:37

know, a real estate person, a dentist,

10:40

a lawyer. But I was really

10:42

attracted to the people who were

10:44

lawyers, but they're really business owner and

10:46

the business they were in happened to be

10:48

law. And I interned at a law firm senior

10:50

year, and the managing partner sat me

10:52

down. And he's like, I'm not

10:54

a lawyer. I'm a businessman. I just

10:56

happen to be in the business of law. I was like, oh,

10:58

that's interesting for aiming. I

11:01

I like I of me likes those

11:03

kind of things, and it's like good story. And then part of me

11:05

is like just rolling my eyes, like, alright, guy.

11:07

Come on. He

11:08

was he

11:08

was ready to drop that nuggets.

11:11

I know. Like you probably dropped it on a hundred

11:13

young people that are out, but it it worked.

11:15

By the way, side note on McKinsey, if you ever

11:17

wanna just get absolutely wracked in

11:19

life, going do a McKinsey interview with

11:21

no preparation. I did

11:23

that. It is not pretty. Like, you got you

11:25

had asked to do, like, you know, how many golf balls

11:27

fit in a cool bus. yeah. On

11:29

the fly. Don't recommend it. Don't

11:31

recommend it. Okay.

11:33

So you guys knew each other or

11:35

didn't. At say

11:36

new of each other. Okay. We are in the same

11:39

fraternity. Okay. I I wouldn't even say new of

11:41

each other. Okay. We like kind

11:43

of barely because you were you were two years

11:45

owner. Yeah. Okay. Well, we really knew each

11:47

other through Tameed. Right? Which was probably the

11:49

club we were in, but we were in

11:51

the same

11:51

fraternity, but, like, barely knew of each other. Right?

11:53

Like, the most distant new of each

11:55

other possible, I'd say. So then what what

11:57

happened? Actually, like, what is the story of how you

11:59

guys ended up coming together, Alex? You had

12:01

the

12:01

insight. Around this business. From what I understand,

12:04

it was like and maybe this is the

12:05

PRNs that you've given in the past or the next

12:08

business history of, like, you were tutoring

12:10

-- Yeah. -- a lot of kids as a

12:12

side hustle and making some money doing that, you realize

12:14

that a lot of them had this need for

12:16

simplified business insights. Like, it was hard to

12:18

keep up with everything that was going on in the world, whether

12:20

that was for interviews or things that they

12:22

were having to go on prep for or just for life.

12:24

And there wasn't anything that was speaking their language

12:26

in a simple way. Yeah. I'll I'll let Alex tell

12:28

the story. But first, I just want you to say how

12:30

busy you were a senior year. And I'm gonna

12:32

tell everyone what class you were taking to keep your time

12:34

busy. Yeah. Well, so I

12:37

I think I only had to take two classes. My

12:39

whole senior year And

12:40

Did you already have a job lined up? Yeah. And and,

12:43

you know, the the way that it typically works in

12:45

finances, you have your junior internship.

12:47

I received a job offer

12:49

for my jun after my

12:51

junior internship, which is a whole story in itself

12:53

because I would say, I've

12:56

most of my life been a perpetually

12:58

late person. And I would say I've turned

13:00

a corner in the last year. I've actually

13:02

been on time or early

13:04

most of the time other than a recent breakfast we had

13:06

where I took a wrong turn. Other Or or or

13:08

how about the the the party we had

13:10

for someone who left morning bro?

13:11

The party we had for someone who left

13:14

morning bro. Could you show up

13:16

really, really late for a party? It's really you're a

13:18

little late. The mobile app. Alex

13:20

does have this bad habit of trying to derive from

13:22

Hoboken to New York City to come to things, which,

13:24

like, you're going to be late to half of things

13:26

that happen just to drive. If there's one thing that you

13:28

take from this podcast. It is that

13:30

Hoboken is wildly underrated as

13:32

the sixth borough of New York. But

13:35

anyway, what I was gonna say is I did

13:37

get this job Morgan

13:39

Stanley, so I didn't have to rerecruit my senior

13:41

year. Only I'd say two classes. I was spending a

13:43

lot of time playing FIFA and

13:45

NHL. Living in off campus.

13:47

Like a good frat boy. Yeah.

13:48

I was like the most non

13:51

fratty person in a frat. Actually, the

13:53

very Rief

13:53

actually I can kind of see that. I feel like Austin

13:55

is way frettier than you as like an overall I'm

13:57

just saying I

13:58

wasn't very frettier, but I was way frettier

14:00

than that. I'm just like

14:01

a little nerdy neighborly. Yeah. And

14:03

and

14:04

I looked at your old Facebook pictures. I

14:06

definitely knew that. Yeah.

14:09

And the the very funny

14:12

quick story of how I

14:14

got into a fraternity at Michigan

14:17

is when you do a fraternity

14:19

at at any school, you're supposed to do a

14:21

bunch of them. Like, not all of your eggs in one

14:23

basket so that you don't risk getting rejected

14:25

from the one you Rief I didn't

14:27

know these rules. So I just recruited

14:29

or They call it rushing. It's probably

14:32

gosh.

14:33

It shows how much of a crap boy is.

14:36

I just did recruiting. Eight

14:39

pie. Yeah. I was asked that

14:41

question about fitting tennis balls in at seven forty

14:43

seven at eight pie. And

14:45

the only reason I got into eight pie

14:47

was

14:48

Aripai. I was just the one of the newest

14:50

utilities. I know. The only reason I

14:52

got into Aripai

14:55

is because the rush chair a

14:57

time for the person who's responsible for ultimately choosing

14:59

who gets into the pledge class. True

15:01

story. Rief that

15:03

summer before, he got into

15:05

an accident with my mom.

15:07

And everyone was fine. That's why I

15:09

talked about it. Yeah. Like, he was

15:11

celebrating his twenty first birthday.

15:13

Was joy riding his dad's

15:16

Mercedes and cut as

15:19

my mom was making a left turn, crushed her

15:21

driver's side door that to use the jaws of life to get

15:23

her door

15:23

out. Like, she was totally fine. But, like, it

15:26

was a very scary incident. Like, if she wasn't

15:28

driving a big truck, it could have been

15:30

an issue. And the fur when

15:32

I first met him there, I knew who he

15:34

was. And I was like, by the way, I just

15:36

wanna make the connection

15:36

here. He just you

15:38

almost killed my mother.

15:39

He just

15:40

never looked at me in the same way after. Oh,

15:42

yeah.

15:42

You're in. You're a shoe in. I mean, that's a hundred

15:45

percent

15:45

wide gun for the fraternity. And

15:47

it explains why I'm not Freddie at all. That is a pretty

15:49

good story. I like that. Okay. So then how did you

15:51

guys actually meet? Yeah. So I

15:53

I started writing this daily

15:55

newsletter at the time, which was called

15:57

the Market Corner. And

16:01

again, I don't know what the actual

16:04

reason I started writing this was, but it lived

16:06

somewhere between selfishness and selflessness. On

16:08

the selfish side, me feeling

16:10

like I'm gonna be wildly

16:12

unprepared for Morgan Stanley when I

16:14

graduate Rief I only do two classes and play

16:16

fee for the whole year. And that's why you didn't you didn't

16:18

drop the name of your class, I don't think. Well,

16:20

that wasn't senior year. Maybe it was senior. I

16:22

took a class called water. There's just

16:24

it was Like

16:24

David Foster Wallace, like, this is water.

16:27

It was just

16:27

a class about everything that It's a

16:29

senior elective.

16:30

It was a senior

16:30

elective. Well,

16:31

that's doing up in Michigan, man. This Ann Arbor

16:34

Life. Yeah. So so one of my two

16:36

classes was water. But

16:38

I took a class

16:38

called weather and storms at Stanford. That was one

16:41

of the athlete classes that people took. So I

16:43

can't actually talk that much

16:44

shit. Honestly, that sounds cooler than water.

16:46

And so I'd say I

16:48

partially started writing this because I

16:50

was worried that my brain was gonna

16:52

like just melt atrophy during

16:54

senior year. And it was it was a force function

16:56

for me to keep up to date with markets. Then

16:58

the selfless side was like helping

17:00

students prepare for job interviews, telling

17:02

me that they don't like The Wall Street Journal, I wanna write

17:05

something that's better. The true story probably

17:07

lives somewhere in between. I'd been writing

17:09

this for a little while and the original

17:11

product was a Microsoft Word

17:13

template converted to a PDF attached to

17:15

an email -- Mhmm. -- there was no landing page

17:17

or website if you wanted to

17:19

daily? I would say it was daily other than

17:21

days where I missed it. Okay. And

17:23

How many people were on the list in those early days? Yeah.

17:25

So the first email went out to, like,

17:28

forty five or fifty people. K. And it

17:30

started with, like, a pie people, people

17:32

in the business school and my family. And

17:34

then I would just start getting messages from

17:36

people saying, hey, I heard about your

17:38

daily roundup, can you add media or listserv? And I type

17:40

in email addresses. It was just a listserv I

17:42

was managing. I got to I

17:44

wanna say it was December

17:47

of twenty fourteen or January of twenty fifteen.

17:49

And I sent out an email basically saying,

17:52

I wanna take this more seriously.

17:54

I I like I didn't even call the business, but

17:56

I just wanna take this next level because there's

17:59

appetite. Let me know if you wanna help out and I sent

18:01

that email to my readers.

18:03

Austin was one of those readers. He

18:05

reached out saying he had ideas and he

18:07

wanted to help. And we met in the winter

18:08

garden, which is like the main lobby area

18:11

of the business school. And we basically

18:13

just talked for an hour about what

18:15

the future

18:15

of this

18:15

newsletter could look like. That was like our first

18:18

conversation. So what

18:20

peaked your interest about it, Austin. Like, why

18:22

did you get excited? Because you were if I

18:24

recall correctly, you were younger than at the time,

18:26

but you were on a similar financy

18:30

looking path. Yeah. So I was a sophomore and

18:32

I said there were two reasons. One

18:34

was high level and one was about the

18:36

brewers. So high level by sophomore

18:39

year, I had started to ask some questions about

18:41

about this investment banking path.

18:43

And I was like, I'm

18:45

not sure if this is a act what

18:47

I wanna do. I talk that people have done this banking

18:49

thing, and it seemed kinda terrible.

18:51

Like, it seemed pretty awful,

18:53

you know, hundred hour weeks in building

18:55

Excel models, and eight ten years before you

18:57

had any real responsibility. And I said,

19:00

I kinda wanna hedge in case this thing

19:02

doesn't work. I had a couple of friends who

19:04

were more entrepreneurial minded I

19:06

started I actually listened to a podcast

19:09

series that I'm sure I assume

19:11

you've listened to. It was a Sam

19:13

Altman class at Stanford.

19:15

It's ten episodes. It's, you

19:16

know, Paul Graham does one. But they learn how

19:18

to start a startup. Yeah. I think it's called how to start

19:20

a startup. And I listened to that. I

19:22

was like, whoa. This is way cooler than the whole

19:25

banking thing. Like, how do I get into this? So

19:27

I always had this idea that let me

19:29

hedge in case the banking thing isn't

19:31

for me. Still a hundred you know, ninety

19:33

nine percent thought I was going to banking. I

19:35

spent the summer after software year

19:36

banking. And then, selflessly, I read the morning

19:39

brew thing. Or the market corner

19:41

thing at the time. And I was

19:43

like, this is actually pretty

19:45

good. No one reads the Wall Street Journal. You'd

19:47

walk into the business school. You'd walk down the there.

19:49

There's a stack of ten newspapers and you leave

19:51

at night and that stack would still be there

19:53

basically. No one would read it. And I

19:55

bought into the idea that you

19:57

could actually make the business world more engaging. Now did

19:59

I think it was a real business? No.

20:01

Like, I agreed with that professor.

20:04

But I don't know. There was

20:06

something there about it. And also, to be honest,

20:08

like, people were signing

20:10

up and I was reading, but it wasn't good. Like,

20:12

the no PR answers, it looked horrible.

20:14

Like, it was terrible. I don't know if we got a picture that

20:16

we can put

20:16

up, but the original newsletter looked

20:19

terrible. There was a bull and

20:22

a bear like -- Fighting. -- word art.

20:24

Fighting. Like, it looked horrible. Yeah. I was like, if

20:26

I'm reading this thing and it's written like

20:28

okay and it and it looks

20:30

like

20:30

shit. It's written okay. I mean, it was yeah.

20:32

He was reading the entire Wall Street Journal cover

20:34

to cover and summarizing it in, like, three hours. How

20:37

big can it have been? But like

20:39

but I still read it every day. And so I think

20:41

it was that. It was the classic thing where

20:43

product sucks, but people still use it.

20:45

Like, oh, that means it's like Amazon. Amazon looked

20:48

terrible. Right. It's a worst designed site

20:50

that I I use yet people people use it. So I thought

20:52

that was interesting. The thing

20:52

that's so interesting to me when I hear story

20:55

recounted is like, I

20:56

mean, we're doing a podcast called The Crazy

20:59

Ones. This is like kind of a

21:01

crazy idea at the time. From a business

21:03

standpoint, like, today, it's super obvious to say,

21:05

like, you can start a newsletter, you can

21:07

monetize it via sponsors, you can, like,

21:09

build a business, you can do courses, product, like,

21:11

there's so much opportunity around an

21:13

email list. At the time, that

21:15

wasn't really a thing. Like, the creator

21:17

economy, there was no VC that was like, yeah, I'm a

21:19

creator economy investor. You know, that wasn't

21:21

a thing that people were going after, and

21:23

yet you guys had this spark

21:25

and decided to start doing it and

21:27

pursuing it. Part of it sounds like it

21:29

was like you had time on your hands. And part of it

21:31

sounds like your alternative kinda sucked

21:33

and you weren't that excited about

21:34

it. Yeah. Go ahead. Yeah. I I think there's

21:36

just just a few things that that

21:39

made it successful in the early days.

21:42

One, we didn't intend

21:44

for it to be a business. Mhmm. And if we

21:46

did, And we thought about it as a business in

21:48

twenty fifteen. I think it would have failed. We would have

21:50

made long short term decisions to make a little

21:52

money here or

21:52

there. But because of the side

21:55

project, we didn't. That's an incredibly important insight, by the

21:57

way, for all listeners. I I mean, I

21:59

talk about this constantly of, like,

22:01

whenever anyone started something,

22:03

they were just pursuing it out of like

22:06

pure passion, interest,

22:08

excitement, and joy of actually doing it. The

22:10

process on a daily basis was so

22:12

amazing to them. And that paradoxically

22:14

is actually what allowed it to scale and

22:16

succeed. They weren't doing it for the, like,

22:18

hey, let me monetize when I get to five thousand

22:20

customers. I'm gonna build my figure revenue

22:22

stream. Like, those things are really really

22:24

difficult because then you're just focused on price, the

22:26

whole way along the way you're not process oriented. So

22:28

that's like, I think that's a super important insight for

22:30

people to take totally and we got there. Right? Twenty seventeen where

22:32

we we always kinda stalled the math and we

22:34

had so many people saying, hey, this newsletter thing's

22:37

dumb. And Alex and I would sit down

22:39

once a week or once a month and look at the Excel model

22:41

and be like, these people are telling us

22:43

we're stupid. But we we're

22:45

acquiring subscribers for x.

22:47

We're making y off them. So if we

22:49

can get the list from fifty thousand to a

22:52

hundred thousand, I think the profit

22:54

number's gonna And then I think we get to two

22:56

hundred thousand. And I think there were a couple

22:58

of moments. I don't know if you felt this way, but there were a couple moments where

23:00

I was like, either

23:02

we have the numbers. So either no

23:04

one else sees this or we're complete

23:07

idiots. And and and I think

23:09

I there are times where second guest are sales we're

23:11

like, the numbers are so clear. It's the most obvious

23:13

excel model in the world. Costs stay the same.

23:16

Revenues go

23:16

up. Profit

23:17

goes up. Yeah. I mean, I just think the

23:20

best part about it is how simple the business it

23:22

is, of yet no one

23:24

understood how simple it was. There's

23:26

a few things that I'd add which is I think

23:28

the point about something not feeling like a

23:30

business from day one is such

23:33

an important thing because it

23:36

reminds me of when

23:38

I interviewed Tim Farris and what

23:40

one thing he had said was like he

23:43

loves interviewing non business

23:45

people, like, people who are just, like,

23:47

on the fringes of the Internet

23:49

and society who are like, when I talked to him,

23:51

he I I said, what are you going down the rabbit hole of right

23:53

now? And he was, like, archery and

23:56

compound bows, animal

23:59

tracking, and one other

24:01

thing. And but he gave me the reason like

24:03

because the people who are best

24:05

point one percent in the world at this are

24:07

so genuinely obsessed with

24:10

the craft because they can't be in it money because it doesn't pay

24:12

well. And there's something so like

24:14

amazing about that to me is like you

24:16

actually go to

24:18

people who can't be motivated by money and you find just like kind

24:20

of this unbridled passion

24:23

for the thing and for the journey of it. So

24:25

I think that's huge. I think

24:27

you know, the other thing is you

24:29

talk about this a fair bit like you've

24:31

talked about on Twitter is like increasing

24:34

your luck surface Rief. And

24:36

I think was absolutely a part of it. Like, there were

24:38

things we did in the early days to increase our

24:40

luck surface Rief. Like, making

24:42

the like, making the decision to

24:44

write this thing. Like, if I didn't make the decision to write

24:47

this thing, I could have very easily just played FIFA and

24:49

NHL senior year, but I didn't. I decided to

24:51

write this thing. So that increases the surface area

24:53

a little. Reaching out to those

24:55

professors or possible investors and doing

24:57

it relentlessly irrespective of

24:59

if they gave us a yes or no increased

25:02

surface area. But there's another where, like, I think

25:04

there truly was luck. Mhmm. Like like,

25:06

I do think the fact that Austin

25:08

was a sophomore I

25:10

was a senior. We were still in

25:12

college. We had two years

25:14

now to not have to think about something as a

25:16

business because we weren't in our

25:18

professional lives. So the trade off of

25:20

life didn't increase in cost

25:22

yet. Like, that was huge. And I also

25:24

think we had good

25:28

thought process for why we started with an

25:30

email newsletter. It was cheap. It

25:32

was opt in. It's what college students were

25:34

already doing. But we didn't have the thought process

25:36

around like oh, the cost base is

25:38

this, the revenue is this, you could just scale the

25:40

margin. So I'd say there was luck

25:42

that came out of just well intentioned

25:43

strategy. Have you guys seen the

25:46

I think it's Charlie Wign The investor

25:48

has the, like, matrix of like,

25:52

like, level of complexity of

25:54

the business. That, like, you know, you kind

25:56

of like you wanna be operating in

25:58

a place where the business is,

26:00

like, kind of complex sorry.

26:03

Rief, boring, but then, like, difficult to execute

26:06

against. And you guys

26:08

kind of I mean, like, over time,

26:10

the industry might get sexier over time and then more competition

26:12

comes into play. But when you're operating at the

26:14

time when it's really not sexy, I feel kind

26:16

of like

26:17

you're shooting fish a barrel a little bit. I

26:19

feel like I think of, like, plaid when I

26:21

think of that type of business or, like, notarized. I

26:23

mean, Stripe when they first started is like a it's

26:25

it's super complicated to do, like, very different golden

26:28

challenging to do, but boring. Like,

26:30

not a sexy space to go build in, you know,

26:32

in those spaces versus like space,

26:34

like space

26:34

x, super super complex, but like really

26:37

really sexy. Totally that like, again, at

26:39

the time, just to give you a sense of, like, the

26:41

competitive landscape at the time, it was

26:43

I don't know how long the scheme had been in business.

26:45

They had raised their Cedar A.

26:47

Right? They they became big and and

26:49

they started twenty twelve. They they raised a Cedar

26:51

A in twenty fourteen. So they were

26:53

probably maybe the million subs And

26:55

and I I remember at that time, us thinking, like, it

26:57

is absolute craziness to think we'll

26:59

ever be at this size as

27:02

them. Like, they were the kind

27:04

of the the North Star in terms of how big a

27:06

newsletter business could be. As we did

27:08

research, we had heard about Daily Candy, which

27:10

was a newsletter and failed. It's

27:12

funny also over the years to --

27:14

Successful exit. Yeah. -- but failed post exit,

27:16

which is interesting. I think

27:16

that's a that's a theme totally.

27:19

And it's also fun to

27:19

that too. It's also funny to to hear about

27:22

now, like, as I've done research on other

27:24

businesses over time, how many

27:26

businesses started as newsletters, and you just wouldn't

27:28

know it. They started as newsletters to prove an

27:30

audience, and then they grew into something

27:33

beyond a

27:33

newsletter. I mean, that's sort of what Sam parted with

27:35

with the hustle. Right? Like, it was really it was the

27:37

hustle in the early days, and then they built

27:39

trends, which was really, like, I think, the month like,

27:41

a big money making business on the And it was actually

27:43

something for the newsletter. Oh, yeah. It was an event.

27:45

The conference calls. Right? Yeah. Conference blog.

27:48

And then it was a vlog and then Kendall

27:50

Baker who writes Axio SportsNow he

27:52

was one of their first writers. It was like we should do a newsletter.

27:54

The newsletter became huge. It was

27:56

great. And then obviously trends became

27:58

their subscription product that sat under

28:00

it. Interesting. Yeah. I

28:02

wanna talk a little bit about something around

28:04

growth. So we're talking a lot about, like,

28:06

the very early days. And you

28:09

know, not being able to ever aspire to this idea of having a

28:11

million subscribers, which obviously in hindsight seems like

28:13

a small number relative to what you have today.

28:16

Every single entrepreneurial

28:18

success story that I've encountered has a

28:20

common thread of these like

28:23

dirty crawling through the

28:25

mud growth tactics.

28:27

That hacks, whatever you wanna call them, that they had to do

28:29

in order to, like, get off the ground to get those early

28:31

customers to get some initial traction. What

28:33

is your and you can have different ones or you

28:35

could have the same one? What

28:37

is your favorite story of the like

28:39

dirty, nasty thing that you had to do to

28:41

get off the ground in those early days?

28:44

So I'll give I'll give three doing it correctly. Right? Number

28:47

one, we to get to, let's call it

28:49

a thousand. And again, this

28:51

goes back to Alex. It's just

28:53

relentlessly so many times Alex would present something.

28:55

I'd be like, dude, like,

28:57

that sounds horrible. And be like, yeah. But, like, obviously,

28:59

we're gonna do it. And and so the first

29:01

thing we did was We would and

29:04

Michigan was a big school, big business school. E

29:06

com 101 lectures, five hundred

29:08

students. Right? Accounting 1012

29:10

fifty. I mean, compared to a two thousand

29:12

person list, a thousand person that's a a lot

29:14

of people. And so it looks like let's just go let's

29:16

ask Rief professor if we can have five minutes,

29:18

just five minutes, beginning of class.

29:20

And let's pitch Morning Brew. And so

29:22

we did it. We walked into our first e com 101

29:25

class. We pitch Morning Brew. We're pumped up.

29:27

I'm nervous. I don't like public speaking.

29:29

We give the pitch and we check the website.

29:31

Like, two subscribers. Like,

29:34

maybe two subscribers. And, like, we're

29:36

defeated afterwards, and we're, like,

29:38

you know, like, what do we do? And then we

29:40

we we figured out, like, no one's listening. No

29:42

one's paying attention. There's too much friction

29:45

to go online.

29:47

Go to morning brew dot com. It's actually morning

29:49

brew daily dot com. Okay.

29:51

Sign up. And so we said,

29:53

you know what? What if Alex pitches? And Austin

29:56

walks around with, like, a printed out Excel

29:58

document basically and

30:00

basically stares people in the eyes until

30:02

you they give you your email, and

30:04

that's what we did. So I would I would spend time It's like door

30:06

to door sales. So I'm a newsletter

30:08

list. I like it. I would walk around

30:10

the the the big

30:13

lecture hall, five hundred people, and I kinda just stand there.

30:15

Give me your email. Give me your email.

30:17

And I get big on them. Like, did you

30:19

pop your chest up? It to even look

30:21

into the song in your email. If

30:23

I at the time, if I spoke in front

30:25

of five hundred people, I was getting five

30:28

hundred emails. Because I you know, there's whole classic thing, like, you

30:30

know, the number two fear in life

30:32

is a public speaking, and number one is is or

30:34

number one is public speaking to his death, like, we'll

30:36

rather be in that in the casket than

30:38

speaking at the the urology. That was me

30:40

at the time. And so I was like, well, if I'm gonna

30:42

do this, I need

30:44

those emails. And and then afterwards,

30:46

There's no, we didn't have, like, a way to scan them. So we

30:49

would -- Man, man. -- and put

30:50

it in five hundred emails. I'd send the floor in

30:53

the back of the lecture hall. So that was number

30:55

one. That was, like, zero truth. And by the way, the amount of time like,

30:57

we've spent hundreds of hours

31:00

debating whether i's were l's

31:02

because, like, it was all haloing. So,

31:04

like, we would basically have to put in multiple permutations

31:06

of people's emails because we didn't know what

31:08

certain letters were. Rather

31:10

than

31:10

just scrapping the ones that were un you

31:13

actually were running all the way before that. You

31:15

needed just two of that. Two of them would bounce

31:17

one would work. Yeah. So that's that's zero

31:19

to a thousand. Right? We can we can go three

31:21

stages. Okay? Then let's call

31:23

it, you know, fifty thousand to two hundred

31:25

thousand or fifty thousand or two hundred and

31:27

fifty thousand. We spent

31:29

a lot of time talking about the referral program. So I'll

31:31

leave that. And if you wanna talk about it, we can. But the

31:33

other unique insight we had is

31:35

we really start tracking

31:37

the opens of readers by source.

31:39

And what sources would open

31:42

the most? And we found that when we

31:44

did cross promotions with other newsletters,

31:46

it was really successful. Mhmm. Those people

31:48

and engage more. And it makes sense. Right? There are people

31:50

who are just newsletter people. Just like

31:52

when you wanna pro to podcast, you do it on other podcasts like

31:55

mediums, pro like mediums.

31:57

So we bought sorry, buying

31:59

ads. One other newsletters. And then

32:01

we were like, you know what? There aren't enough newsletters

32:03

to buy ads on. What if we help

32:05

other newsletter companies build up their

32:08

ad business? And so we kind of came in. We acted as

32:10

like sales consultant for

32:12

two or three companies. in exchange, we'd

32:14

buy their first, you know, months of

32:16

ads. And we

32:18

grew from let's call it fifty or a hundred to

32:20

two fifty with a ton of

32:21

really, really high quality subscribers from other

32:23

newsletters that stuck around and

32:25

that was huge for

32:27

us. Any others that jump out to monitors that

32:29

cover it for you, Alex? So there's two

32:31

more. I love the Excel spreadsheet

32:33

one. That's just so good. I don't know why

32:35

it is, but it's

32:36

like those things still to this day are

32:38

the things that I love doing most.

32:40

Like -- Typeing in hand emails. -- like

32:43

just doing a lot of that these days.

32:45

Just fucking yeah, finding

32:47

the most kind of creative

32:49

scrappy ways --

32:50

Yeah. -- to acquire audience. I don't know why it is,

32:52

but I just like love the feeling

32:55

of it. I asked people recently. I asked

32:57

every time I was running into, like, an entrepreneur

32:59

that had a success story, I would ask them, like,

33:01

what is your favorite thing about the

33:03

entrepreneurial journey? Like, Anker

33:05

Nogbald just started this new company, and he's

33:07

getting back into it. He that dude has made a ton of

33:09

money. Right? Like, he already had a massive success story to

33:11

ask him, like, why are you getting back into this? Why

33:13

are you doing this again? And he said I love the

33:15

feeling of that like aha moment

33:17

where I feel like I figured something out that

33:19

no one else knows and you're you're hitting on the

33:21

same thing. It's like you figure out

33:23

this little sheet code that for some reason just works and you're

33:25

able

33:25

to go and exploit it. It's a very

33:27

addictive feeling and I would say there's two other things

33:29

that come to mind. One which

33:32

we definitely do not do today morning brew

33:34

because I think the legality is borderline.

33:36

Mhmm. But in the early days,

33:39

for, I would say, both growing our list as well

33:41

for acquiring advertisers. I remember,

33:43

I don't know how many years it was. Austin

33:45

and I would get an email every time there

33:47

was a new

33:48

subscriber. It was, like, that was, like, the

33:50

the definition. It was, like, the

33:51

shot of Ching thing. It was. That that's exactly

33:53

what it was. And we'd also get it when people hit

33:55

certain referral landlords, like, five, ten,

33:58

twenty five. And what we would do, especially as

34:00

we were building up Morning Brew's referral program,

34:02

an ambassador program, which became big,

34:04

and looking for advertisers, is we

34:06

would go through at the end

34:08

of the day, like, I think the kind of the marketing strategy that

34:10

continues to shape our thinking

34:12

in everything is like this

34:14

hub and spoke model. It's

34:16

your hub are like who are the people who give you access? But

34:19

people are channels that give you access

34:21

to a bunch of the

34:24

right people. So if you can

34:26

get to them, it's a very leveraged act of acquiring more people. Right? So like

34:28

a lecture with five hundred people,

34:30

very leveraged action of the

34:33

was the hub. And one of the other ways to

34:36

think about it was if we

34:38

could turn

34:40

our newsletter subscribers into champions in some way, they're a hub

34:42

for other things. And so in the early

34:44

days, a lot of

34:46

our ambassadors came

34:48

from us literally pouring through our list, filtering

34:52

by domain names of certain schools. We wanted

34:56

to have presence at reaching out to those students --

34:58

Mhmm. -- and asking them if they wanted to be

35:00

ambassadors. Same thing on the

35:02

advertising side. A

35:04

lot of the initial advertisers we got, we would fit

35:06

look at what are companies that we wanna work

35:08

with, who are what we would call chronic

35:10

newsletter advertisers. They've advertised in ten

35:13

other newsletters. We'd look at our list who has the

35:16

domain

35:16

from, at the time, Brooklyn,

35:19

and Casper, etcetera, look up that's all the t to

35:21

c brand. Exactly. We we look up that person on LinkedIn. If they worked in

35:23

a marketing function, we would hit them up, and we knew

35:26

that we wouldn't have to convince them of what Morning

35:28

Brew was.

35:30

So I'd say that was a big one. The second one was, I

35:32

I think just the evolution of our college ambassador

35:34

program was really interesting

35:36

because at the time, no

35:39

media companies were

35:42

thinking about referral programs or ambassador

35:44

programs. The only other one that did was

35:46

the SCIM. But for whatever reason, I they didn't really publicize,

35:48

like, what I thought was a really

35:50

smart marketing strategy.

35:52

And so we just we

35:56

tinkered over semesters of the best

35:58

way to do a college ambassador program. So the first

36:00

time we did it, we had ten ambassadors. We

36:02

were super stringent. We went through resumes. We had an interview process. And we're

36:05

like, we're gonna pick the the

36:07

most impressive people on college

36:10

campuses. Who's like the student body president in like different clubs

36:12

because they have access to all of those hubs

36:14

I just spoke about. That was the

36:18

wrong strategy. Because all those people already have spread themselves thin

36:20

when they become an ambassador for Morning Brew,

36:22

they don't have the time to dedicate

36:26

to it. Then the second semester, we're like, we're gonna go

36:28

and swing the pendulum in the exact opposite

36:30

direction. We're gonna open the

36:32

floodgates. So we had at

36:34

one point three hundred ambassadors from two hundred

36:36

schools. We said we're gonna

36:38

automate the beginning of the program

36:40

as much

36:42

as possible. We're gonna have an

36:44

automated email sent to people saying apply to the ambassador program. And automated email

36:46

is gonna say, we've received your applications.

36:49

It's very selective. We're going

36:51

to talk about it and get back to you. An automated

36:54

email that says, you've been accepted to the

36:56

program, whereas everyone was accepted. It wasn't like a

36:58

five percent acceptance rate. And only when

37:00

you got to say, like, twenty five referrals,

37:02

did you actually get human interaction

37:04

from Austin or

37:04

I? And so it was just fun to, like, just

37:06

iterate on this program over years.

37:09

How did you actually scale voice? Like, that

37:12

that's one of the things that I find most

37:14

interesting and incredible about what you

37:16

guys did in that you

37:18

went from you know, the single email. And presumably, that was

37:20

still you guys writing that in the very early

37:22

days. It started to grow. And obviously, it has

37:24

now branched into a whole ton

37:26

of different vectors and a whole

37:28

ton of different emails and products and different

37:30

things. One of the biggest challenges of doing that

37:32

is the morning brew was so

37:34

successful because it had such a

37:36

unique voice and it really felt like a person writing it to you that was

37:38

funny and snarky and pithy and

37:40

also delivered really poignant

37:42

business insights. How did you scale

37:44

that? Because that seems like a really

37:46

challenging thing to do. Yeah.

37:48

I mean, it's still something

37:50

we think about today. Right? What

37:53

we're trying to figure out now is how do we scale our voice and our tone

37:55

to multimedia, to podcasting,

37:57

to video content. I'm

37:59

not sure, you know, we don't do a ten out of ten job right now.

38:02

We're still working on that. But in the early

38:04

days, it was a real question we had. We

38:06

sat down with

38:08

the first the team at the first eight of us. And we said, hey, what do

38:10

we wanna do next? We got to

38:12

more newsletters because we thought it was a good

38:14

business model. But then we sat

38:16

down and we had that conversation. We were

38:18

like, but what actually matters in these

38:20

newsletters? Like, let's build a criteria.

38:22

Let's build a

38:24

rubric. Right? Let's say we find a writer who like, the first one we were launching

38:26

or the second one was retail. And we said,

38:28

okay. What if we have

38:30

someone who's a seven out of ten in

38:32

retail knowledge? An out

38:34

of ten in writing, but a two out of ten in

38:36

Morinboro's voice. Would we hire them?

38:38

The answer was like no. Mhmm. But we

38:40

did get to a point where

38:42

like, okay. If the daily newsletters at ten out of ten, what

38:44

are we willing to accept? Right? Because

38:46

you're not gonna find someone

38:48

who is a ten out of ten on

38:50

retail content. A ten l on

38:52

business knowledge. Right? Ten l ten

38:54

on editorial ability a ten l

38:56

ten on tone. And so we have to

38:58

understand where were we willing to

39:01

like acquiesce, where were we

39:03

willing to give up something? Yeah. It's

39:05

like you had multiple burners and they all have

39:07

like of like a dimmer switch. You need to

39:09

figure out what the optimal thing is across all of

39:11

them in order to scale. Exactly. And the second

39:14

thing is we were in person, we were a tight

39:16

knit community, and our managing editor Neil

39:18

is unbelievable. He is so good and

39:20

he did such a good job training

39:22

people and making that voice

39:24

ubiquitous. And so is he still here? Yeah. He's still here.

39:26

You know I knew him growing up? I did know that

39:28

because he We went to a bunch of,

39:30

like, Jewish holidays growing up together. Like, my mom when she came over from India was,

39:32

like, her host family in college

39:35

was, like, his like grandparents, his family. Wow. So so you probably

39:37

don't know this. But Neil, Slack

39:40

me, I can look it up later. Neil, Slack me, I

39:42

think, when you had, like, six hundred

39:44

Twitter followers, hey,

39:47

this guy, he's pretty

39:49

interesting. You should check him out. I think

39:51

it DMDU maybe. He's

39:53

writing some good content. And

39:55

at the time, that was what? Twenty twenty when you started?

39:57

Yeah. Twenty twenty. So yeah. I I mean, for us

39:59

to even think about how we're partnering with Creator.

40:02

Rief was even a thought Sounds like a like, it's cool, but

40:04

I'll let it go. You guys both ignored me, by the

40:06

way. I'm just gonna call them out right here publicly. Like,

40:08

I've dm ed both of these guys. Back

40:10

when I think I had, like, a couple thousand followers

40:12

on on Twitter in the early days. These guys were both already, like, semi

40:14

famous. And I was just like, hey, god. You

40:16

know, Eager, like, wanted to wanted to be friends and wanted

40:18

to,

40:19

like, talk about what they were doing. Both

40:21

ignored me just to just to

40:23

say it. Nothing

40:24

worse. Look how far we've come. Yeah. I was gonna

40:26

say we're gonna we're gonna have to go back to the tape and actually

40:28

find that this is the I

40:30

know it is because I've seen I've seen this thing. I think I've brought it up. I think I've brought

40:32

it up. It's not just you. I do a host. Yeah.

40:34

So yeah. That which is fair. I I

40:36

totally understand it now, by the way, now that

40:39

I'm gonna a different position. It's very hard to respond. By the

40:40

way, one one last thing I just wanna say on

40:43

voice. So one thing about

40:45

Neil, which I can't believe you

40:47

didn't mention is the thing that sealed the deal of why we didn't like that. So

40:49

in the early days, I'd

40:52

say none of our hires

40:54

were journalists. And we've

40:56

hired a more, let's call it, like,

40:58

traditional journalist,

41:01

journalistically trained writers

41:04

over time. As we've gotten a

41:06

sense of kind of what

41:08

we're looking for. But in the early days, we didn't hire

41:10

any journalists. I think largely because we

41:12

couldn't afford them. Largely because we didn't think journalists want wanna come to Brew

41:14

because there's a very, like, the investment

41:16

banking path. There's a very clear path of

41:18

if you go into journalism, what you ultimately

41:22

wanna do. And so all of our

41:24

initial hires were not writers by training. It's like Neil, to

41:26

use the example, he wrote for Marilyn's newspaper,

41:28

that was the only writing he had

41:32

ever done. You just had

41:34

a knack for

41:34

it. And to this day, a

41:36

very simple prompt, writing prompt,

41:40

is like the best proxy for someone get getting hired

41:42

at the brew. You take a big

41:44

business news story from last few days,

41:47

in a hundred fifty to two hundred fifty words,

41:49

you summarize this story in

41:51

a way that connects with the

41:53

audience through voice. Within two sentences, we know whether you're going to

41:55

be the person or not. And with Neil, what

41:58

actually sealed the deal with him in his

42:00

interview process was

42:02

two things. Well, first of all, say, we actually fucked up and didn't

42:04

hire him at first. We gave an offer to someone

42:06

else. Someone rejected that offer and then we

42:08

came back

42:10

to Neil. And that ain't going to miss He's gonna kill it. He's gonna kill

42:12

it by the way. Well, I I or he didn't know

42:14

he he knows that. But I would say that's, like, one

42:16

of the big bigger mistakes we've made

42:18

is if

42:20

he wasn't available, the the the trajectory of the business would

42:22

be so different. But with him, there are

42:24

two things that stood out in the interview process.

42:27

One, I asked him to teach me

42:30

something that he's

42:30

super passionate about. Doesn't have to be our

42:32

business at all. And he's a hit a

42:35

US history junkie. And he basically

42:37

taught me about the the battle of Tyconda Roga for, like, thirty

42:40

minutes. And to me the the

42:42

amount of detail and nuance he

42:44

understood, I

42:46

was like, fascinated by. The second thing really what's held the deal

42:48

is Neil is an Acapella singer. Mhmm.

42:50

And he's gonna absolutely kill me. He's gonna

42:52

kill you for telling you

42:53

for telling this thing is

42:55

there was a YouTube video. Like, we we

42:58

researched all the hires we make, and I

43:00

looked him up on YouTube, and there was a video

43:02

of him performing with his

43:04

Acapella group. And the --

43:06

In college. -- in college. And the song was

43:08

called CHOP it off. And it was a song

43:10

about circumcision. And he

43:12

had written all the lyrics of it, and

43:14

it was so incredibly clever. Yeah. I was like, this

43:16

is how we know he has the voice.

43:18

And so, yeah, Neil. Can we

43:20

still look video

43:22

up. Yeah. Yeah. Yeah.

43:26

Yeah. Yeah.

43:26

Yeah. Yeah. Yeah. Yeah. Yeah.

43:29

Yeah. Pop it off. Neil Frohn. It's a it's

43:31

incredible. Neil

43:31

may quit if you put in this shit in touch.

43:33

And the final thing I'll just say that we did with

43:35

a from a voice perspective, and this is why I love

43:37

the early days of business. Our so

43:40

intuitive. Right? You don't know, naturally, all these

43:42

frameworks, especially if you're a first time founder. You just do

43:44

things that you think make sense. We

43:46

had a one pager that define the

43:48

Morning Brew voice as a person. So it'd

43:50

literally be like, our voice

43:52

is Sahil. He is

43:54

thirty something

43:56

years Living outside in New York City. He will

43:58

drink once or twice a week, his

44:00

preferred drink is whiskey. Other

44:02

times, he'll be reading

44:04

ten k's, or watching a TED talk and he loves spending time with

44:06

family and like in

44:08

excruciating detail we would describe that

44:09

person, which I think like brand

44:11

or marketing people call it like

44:13

building personas. We

44:14

didn't know that. It was just like, how

44:16

do we have a proxy for making decisions?

44:18

When we write a newsletter, we're

44:20

editing, editing, whether the Morning Brew Voice would

44:22

say this or

44:23

not. Mhmm. So you mentioned that one of

44:25

your biggest mistakes kind of

44:28

jokingly was was not hiring

44:30

Neil immediately. What are the other ones that jump out to you? Like, what are the

44:32

worst I mean, like, actually bad ones, not

44:34

the, like, oh, yeah. My biggest weakness

44:36

is I'm too attention to, you know, I'm too much

44:38

attention to

44:40

detail. Like, can be the fake interview answer, the the real ones. Like, what are

44:42

the big mistakes that you guys made along

44:44

the way? This

44:47

also may feel a little PR ish. So so

44:49

so you can feel free to push back to the CEO.

44:51

But it's it really is all about

44:53

hiring. I'll get specific, but it's

44:55

all hiring. Right? And there's

44:58

two types of mishiring.

45:00

And I think people usually think

45:02

about the first that I'll give you, but it's

45:04

the second that really The first is

45:06

you just mess up. You hire a senior exec. You know within four

45:09

to six months of the wrong person.

45:12

Hopefully earlier, It takes a month to

45:14

fire them. You have to replace them. And next thing you know,

45:16

you've lost a year because you have to recruit

45:18

them. That sucks. But what's

45:20

even worse is you

45:22

hire someone who the

45:26

company outgrows

45:28

too fast Right? And so they're good. They're really good,

45:30

and they're gonna thrive somewhere else. But

45:32

you need a

45:34

c blank

45:36

Right? You need a cheat a C suite officer

45:38

and you hire an

45:40

SVP or an EVP and that's

45:43

that's difficult because what happens

45:46

is they then after 468 months

45:48

when the company passes them, they

45:50

then go and they say, oh, shit.

45:53

I now feel the pressure because this

45:55

is the biggest company I've ever run,

45:57

content sales, marketing, forward. So what

45:59

do I do? I'm gonna hire a bunch of people

46:01

below me to help me solve that problem. But those people --

46:04

Yeah. Those people are too junior

46:06

because, you know, this person's

46:08

too junior Right? Maybe the person

46:10

below them should be at their level. And

46:12

so next thing you know, you have this

46:14

bloated org of a lot

46:16

of people who might be great but it's just not

46:18

the right team for where you are. And

46:20

that, I think, we've got a couple

46:22

times. And you may not find that out for

46:24

two or three years.

46:26

Right? Like, you can really take a long time to unwind that. And I think

46:28

that's by the way what we've seen over the last couple of

46:30

years that Across the tech

46:31

world. Yeah. Exactly. In venture in

46:33

venture backed companies. They

46:35

they hired so quickly. This is a problem

46:38

that's so pervasive at these companies, and it will just

46:40

crush a company. Yeah. It was just,

46:42

you know, when when

46:44

money's free, hiring and marketing dollars. Right? Or, like, the easiest things

46:46

to deploy. You can just go hire endlessly

46:48

and and give people, you know, give

46:50

give some like SVP the right to hire

46:52

and build entire org. Totally.

46:54

And it's not that these people, these founders

46:56

are bad. These are great founders, but, you

46:58

know, there's the saying it's impossible or

47:01

it's very hard to, like, feel the

47:04

to be able to fad on what

47:06

compounding is, like, even when when you

47:08

think about compounding, you can't actually think

47:12

about compounding Right? Like, it's impossible because that's what compounding is.

47:14

Right? And so it's like, you know, if you're gonna

47:16

grow three extra the next two

47:18

years, I

47:20

can conceptually know what three x is. Right? I can look at an Excel spreadsheet. I can

47:22

even build an org chart. But can you actually

47:24

feel what compelling it is? And can you

47:26

know who the right

47:28

exec is? For a company that's nine x bigger. And the answer for

47:30

definitely first time but probably even

47:32

second time founders is like, no, that's

47:34

really

47:35

really hard. Alex. Worse

47:40

mistake. I actually think

47:42

probably the the

47:45

biggest and I know we're going to get to this, but I

47:47

think, you know, I've spent so much time

47:50

just like reflecting on the business

47:52

and on the last year of years.

47:54

I think the biggest mistake

47:56

was probably

48:02

actually staying in the CEO real too long. I think,

48:05

you know,

48:05

I've spent a ton of time reflecting on the things

48:07

I really enjoy doing, the things I don't enjoy doing,

48:10

the things I'm

48:12

really good things I'm not good

48:14

at. And I think, you know what, there there was a lot going

48:16

on in, let's call it, twenty

48:19

starting in twenty nineteen, But

48:22

I would say the biggest thing that happened was,

48:24

like, we made this big I would

48:26

say, the most important shift that

48:30

you make as a business when you go of

48:32

product or product to

48:34

company. And I vividly remember

48:37

this conversation with Austin

48:40

where and and this is another sub mistake, but

48:42

it was in WeWork. We were

48:44

we were still operating in this mode of

48:47

Just get the newsletter out. Just get our next advertiser

48:49

for the next day or next week.

48:52

Just find that next subscriber.

48:54

Everything was

48:56

reactive. And not proactively thinking about who do we want to be three months from

48:58

now, six months from now, twelve months from now.

49:01

And I remember Austin

49:04

and I talked about how do we get more proactive. And then he

49:06

had one of our early

49:08

investors is the founder of The

49:12

Snuggy. And he he

49:14

recommended you the book. Right? Yeah. Yeah. Yeah. And he

49:16

coincidentally, Adam Ryan, also have been reading at

49:18

the same time. Oh, really? Yeah. And and

49:20

so he had recommended Austin

49:22

this book called Track which is

49:24

by Gina Wickman. It's like, what? You know,

49:26

there's now this set group

49:28

of, like, business planning frameworks out

49:30

there, okay, are scaling up. This one's

49:32

EOS. Mhmm. And Austin Reddit

49:34

and, you know, I would say this

49:36

is kind of like one of the most exciting

49:38

excited moments in the journey. I've seen Austin where

49:40

he was like, this is what we have

49:42

to do to be proactive because it

49:44

really sets up like your vision,

49:46

right people, right seats, ten years, five

49:48

year, three year, one year, and quarterly

49:50

goals, like it's the roadmap for planning your

49:52

business. And he told me you

49:54

have to read this. And I remember I didn't

49:56

read it. And he had asked me, and I was like, I didn't read it. And he

49:58

it's probably like the one time

50:00

or one a few times in kind

50:02

of the whole journey that I would say,

50:05

it felt like Austin was actually mad at me because he

50:07

was like, dude, how can you read this? This is

50:09

like the most important thing that we have to

50:12

do to be able to plan our business

50:14

moving forward. So I remember the

50:16

next day, I spent the entire day and we

50:18

worked just reading this book, cover

50:20

to cover. And I would say, what

50:22

happened there? Is that was kind

50:24

of the turning point

50:26

of us

50:28

getting more proactive about the business.

50:30

And I think in a lot of ways, Austin taking

50:32

on the responsibilities of the CEO of the

50:35

company because I think in a lot of

50:37

ways by following that process, it it

50:40

you to think

50:42

strategically about what is the plan for the business

50:44

moving forward, forces you to think about who is your

50:46

leadership team and who are you hiring into your

50:49

leadership team, forces you to set quarterly goals, run leadership

50:51

meetings, etcetera. And I think after

50:53

that point, there was I

50:56

kind of knew it in

50:59

like my heart of hearts that

51:01

what I was spending my time on

51:03

was largely the stuff that

51:05

I was still energized by, so like new products, like our

51:07

new podcast, our new newsletters,

51:10

new like our

51:12

education business, but what I

51:14

wasn't spending my time on or not necessarily

51:16

energized by was in a lot of

51:18

ways what the job was of the

51:20

CEO as you go into company building and not

51:22

product building. And I would say it

51:24

it it largely led to

51:26

ultimately Austin and I having to have very

51:28

difficult conversations about him

51:30

moving from the COO role into the CEO role,

51:32

moving me moving from the CEO into the

51:34

chairman role. I think

51:36

largely because I didn't kind of

51:38

acknowledge this

51:40

truth earlier, And

51:42

because I think I had

51:44

always kind of had this perception in building a

51:46

business that you have to be the CEO

51:50

because a lot of whom my role models were for such a long time,

51:52

whether it's Bezos or Gates like any

51:54

of these people, they they start the

51:56

business and they run it until Basically, they're the

51:58

captain of the ship forever. And I

52:00

think that kind of ego helped

52:03

me from actually doing what

52:05

I think was right actually for

52:07

everyone, for me, for Austin, for the business. So

52:09

I know we're running up here against the end

52:12

of time. I have one question that

52:14

I really do wanna ask you as

52:16

both on a personal level that I think

52:18

will resonate with a lot of folks out there and

52:20

and founders,

52:22

builders, etcetera. You ended up selling at least a portion of

52:24

Morning Brew. I know you guys are

52:26

still owners to business

52:28

insider in

52:30

twenty twenty. Yes.

52:32

October of twenty twenty. Okay.

52:34

In that transaction, both of you guys

52:36

made a lot of money. You had

52:38

presumably even paying yourself salaries for a while and had been doing well because the

52:40

business was doing well and you've owned a hundred

52:43

close to a hundred percent, ninety plus percent of

52:45

the business at the time. You

52:48

made a lot of money in this transaction. Are you happier?

52:50

Do you feel like

52:52

creating tens of millions

52:54

of dollars of personal wealth has

52:57

made you a happier person on a daily basis. Yeah. I can start.

52:59

So I was I was

53:01

reading a book or

53:04

an excerpt from book book that that Will

53:06

Smith wrote. And he had this quote that I think

53:08

it wasn't about money, but I think

53:10

it it translates so

53:12

well and the quote was

53:14

about fame and it was

53:16

getting something to the effect of Getting

53:18

famous is amazing. It's like absolutely incredible.

53:21

Being famous is

53:23

cool. It's nice. But

53:26

losing fame is horrible.

53:28

And I think the same thing is true about

53:30

money. Right? Am I happier? I think a

53:32

hundred percent? Like, III

53:34

think I am absolutely happier because I had more money.

53:36

And I think there's like that

53:38

whole seventy thousand dollar,

53:40

you know, study that people

53:43

are happier. Seventy thousand dollars. I don't think that's true. I

53:45

think I am happier, but

53:47

I think there are also a lot

53:49

of things that make

53:52

me not happy. Right? And

53:54

so, like, on the net, I am happier, but

53:57

there are also tons of things like,

54:00

for example, When you have money, it's like,

54:02

to to money is

54:04

stepwise. Right? And so making an

54:06

incremental five percent

54:08

net worth, means nothing to me. Mhmm. Right? And

54:10

so that motivation just

54:12

changes. Right? And and the drive is

54:14

just different. Right? And so net

54:16

net, I'm

54:18

happier. But the risk reward profile

54:20

of everything just changes. Rief it just

54:23

complicates everything. Mhmm. And Rief

54:25

makes things more difficult. So I

54:28

think I'm happier. But again, like when I lose a dollar, I'm

54:30

like, oh, that sucks. Right? One small thing

54:32

is I used to love to go to

54:35

casino and gamble. And

54:37

now I'll probably never gamble again in my exact same way.

54:40

Can't never gamble. Yeah. And what's

54:42

funny is when I

54:44

when I before I sold

54:46

morning brew, I would love nothing more than to go play, you know, three hours of

54:48

blackjack for a couple hundred bucks. Right?

54:50

Now, like,

54:52

I betting three

54:54

hundred dollars, like isn't exciting to me,

54:56

but I would never bet something that is

54:58

because I hate losing it. I hate it.

55:00

And so it's just like having monies change

55:02

my relationship with money, it's made me happier, but it just made

55:05

it very awkward. It's like that I personally haven't

55:07

spent enough time thinking about

55:09

and internalizing, like,

55:10

Like, what what makes me happy now that I

55:12

have a certain threshold of money? Alex? Yeah. I

55:15

would say one of

55:18

the the functions of moving into the chairman role and going

55:20

from spending a ton of time in the

55:22

business to less time in the

55:24

business is it left me with time. So

55:26

I spent probably too much

55:28

time thinking about this.

55:30

And I would say a

55:32

few things. I feel incredibly

55:36

fortunate to to be in the position that

55:38

I'm in because I would say the thing that that kind

55:40

of add one to the scoreboard for

55:43

money is to not

55:46

have to feel finding

55:49

financial

55:49

anxiety ever again in my life unless I

55:52

royally fuck something up. Is just an amazing

55:55

blessing. Mhmm. I

55:57

would say after the

56:00

deal, and especially after moving out of the CEO role because, like,

56:02

these are two big moments. They happen relatively close

56:04

to each other. Deal was October of twenty

56:08

twenty. Moved out of the the role in April of twenty twenty

56:10

one. My happiness actually

56:12

went down a lot.

56:14

And it went went down because

56:16

of one, I realized

56:18

I I had money anxiety

56:20

in life, actually not

56:22

tied to my net worth. Like, I still have

56:24

money anxiety today. Even though it isn't

56:26

necessarily rational. I think it's

56:28

potentially because we didn't talk about money

56:30

growing up, potentially it's a generational thing, a

56:32

cultural thing, I

56:34

don't know. But so I didn't have the crutch of, like,

56:36

money was gonna remove my money

56:37

anxiety. So it's not something I don't have

56:39

to work on irrespective of it.

56:41

I would say, The second

56:44

thing is I was

56:46

absolutely motivated in some

56:48

portion by money in the morning routine journey.

56:50

Because it goes back to, you know, how I wanted to feel like there's only cash going out

56:52

of the Lieberman family and done coming in. I'm

56:55

gonna do everything possible to

56:57

make that reality better. Now

56:59

that that's a reality, that can't be part

57:02

of my motivator.

57:04

I would say also I got very

57:06

just afraid of losing like losing any money

57:09

or doing anything anything that jeopardized

57:11

it. So I would say, like, I've realized actually

57:13

in this how risk averse

57:16

I am. The intense paranoia by the way is a

57:18

staple of highly successful and highly

57:20

wealthy people. There's this

57:22

weird paranoia a

57:24

lot of really successful people have about losing it all.

57:25

Like, they think they're gonna end up totally broke, which is Well,

57:28

almost impossible you unless you brutally screw something up.

57:30

Yeah. Well, I would say the big reason for

57:32

me actually was because

57:34

after moving out of the

57:36

CEO role for, I'd say, period of four to six

57:38

months, I was, like, very much

57:40

not this existential or, like, cliche,

57:42

but, like, who am I? Who am I outside of

57:44

Morning Brew? I was not self

57:46

loving it all to myself. I questioned what

57:48

I was actually good at. So I think a lot

57:50

of that money anxiety

57:52

was tied to me being like, I don't know if I'm ever gonna be able to create

57:54

something of value again, so I better

57:56

not screw this up, and I better

57:58

protect this with my life because I don't know if I'm gonna

58:00

bring

58:01

anything else in. That will add on top of this.

58:03

I think

58:04

the greatest thing that it has done

58:06

to increase my happiness is give me

58:08

the freedom of time that

58:11

I