0:00

I've learned to become much more gentle with myself

0:02

over time. I think a year or five

0:04

years ago or seven years

0:05

ago, I was like, god, you didn't. You had a

0:07

bad day, Jesse. He'd look at he'd look at

0:10

yeah. Look at the mirror and slap himself and then

0:12

go back to this. A version of that. And think over

0:14

time, I'm like, yeah, you know what? Like and and it's something

0:16

I try to coach everyone I work with of the younger entrepreneurs,

0:18

I'm like, hey, you know, you got a bunch done this

0:20

week. Like, did did did did the ball move

0:23

forward? Did it go did it not go

0:25

backwards? You know, and and I love the pushing

0:27

a boulder up a hill analogy. I'm like, you know what? If you're pushing

0:29

boulder up a hill, if you keep it in the same

0:31

place or get it forward a little but that's progress.

0:34

What's up everyone? I'm Alex Lieberman. And

0:36

I'm Sofia Amaruzo. Yo.

0:38

This is Jesse Pucci. And

0:41

this is the craze ones. What

0:45

is up Miss Fitz? Welcome back to the crazy

0:47

ones. I'm your host Alex Lieberman, joined

0:50

by my amazing cohost. Sophia,

0:52

Emma Russo, and Jesse Pucci. And

0:55

this is our final episode of twenty

0:57

twenty two. So here's today's rundown.

0:59

First, we're talking about solo partnership.

1:02

That's right, running a business of one.

1:05

We're gonna talk about some actual examples

1:07

of people who are printing millions

1:09

of dollars a year and they are the only

1:11

full time employee on the BusinessBy. And then

1:13

my co hosts are gonna duke it out arguing

1:16

the four case and the against case. Of

1:18

running a business of one. Then we're gonna

1:20

talk about time. How my cohost

1:23

managed their time. How someone

1:25

on Twitter I found is running a billion

1:27

dollar business and they have three

1:29

things on their calendar in given week and

1:31

the strategies that we have to spend

1:33

our time as intentionally as possible.

1:36

And finally, to round off the episode

1:39

and to round off the year, we are going

1:41

to have a quick brainstorm of how we

1:43

think we can improve and innovate

1:45

and grow this show in twenty twenty three. With

1:48

that, we're also gonna wanna hear ideas from

1:50

you. So whether it's now or after the

1:52

episode, shoot us an email at the crazy

1:54

ones at morning brew dot com and let us know

1:56

how we can improve the show, ideas

1:58

to make it better, or recommendations

2:00

for how we can grow the thing. Now let's hop into

2:02

it. What is the future of ESG

2:05

advocacy? How is the SEC

2:07

examining Crypto Filings? CFOs

2:09

have a lot of questions to answer, and financial

2:12

forecasting is no easy task.

2:15

CFO, Bruce, does the hard work for you, dropping

2:17

a quick to read free newsletter in your

2:19

inbox twice a week. Covering

2:21

topics from corporate accounting and taxes

2:24

to risk management and more. Get

2:26

the answers you've been looking for and subscribe

2:29

at CF0 brew dot com.

2:33

So

2:33

let's talk about solo partnership. I

2:35

think that this has become a

2:37

bigger topic just in

2:40

the world of more tools being

2:42

accessible to people to start businesses. Right?

2:44

So, like, we've talked about the topics of

2:47

AI writing code for you. We've talked about no

2:49

code. We've talked about tools like

2:51

sub stack that allow you to spin up newsletter

2:53

and charge for it. And so I think access

2:56

to being a sole printer is more

2:58

open than ever before. But what are your guys'

3:01

thoughts on basically being a business

3:03

of one? I

3:05

would hate it. I love it. Why?

3:08

Sophie and I are so different on this. I

3:10

I you know, I don't know. I'm I'm an extrovert.

3:12

I to me, one of the biggest

3:15

parts of business is leadership.

3:18

And spending time with people and inspiring

3:20

people. And my you know, when I have my highest energy

3:23

is like, you know, in on a

3:25

white board with a group of people coming up with

3:27

ideas. There's energy and excitement in

3:29

the room. And, like, I

3:31

would probably rather make far less money

3:33

and and be doing that every day and just enjoying

3:35

the energy associated with that than I would,

3:38

you know, sitting in this office. Like, I I tried to

3:40

work from home for a minute during COVID and it just, like,

3:42

didn't work for me. It was just too it

3:44

felt, you know, too too much of the same. And

3:46

so I I think it's cool. It's like by the way, I

3:48

love the stories. There was a famous one

3:51

I was a consultant, there was this plugin that

3:53

everyone at McKinsey and everywhere used.

3:55

I forgot the name of it, but it was like a plugin

3:57

into Excel that major PowerPoint sites are in the PowerPoint.

4:00

And it it was like apparently one guy

4:02

making forty million EBITDA a year or something

4:04

that you built this plug in that everybody

4:06

used. But So

4:08

it's cool. I'm like, that's cool, but but you

4:10

wouldn't wanna do it yourself. No.

4:13

Even if it was ten people or five people, I'd

4:15

be fine. Like, with that scale and size,

4:17

I prefer I I like to build organizations. I

4:19

enjoy hiring people, thinking

4:21

about how they interact, thinking about the

4:23

values. Like, that stuff is to me is as important

4:25

as the business. Personally. I think I

4:27

think just on the other side of the

4:29

spectrum, like, is there a point at which

4:32

this size of the business becomes so

4:34

big that you don't enjoy it anymore? I've

4:40

never, you know, hundred people. Like,

4:42

I haven't run a business big enough. I think I've

4:44

seen, like, people like Rick, I've talked about at Red Ventures

4:46

or Amazon. I see what they're doing. I'm like, that

4:48

looks really cool. Like, Yeah.

4:50

They sort of have this platform and all these

4:52

people and and the culture. And so

4:55

I you know, I'm not sure yeah.

4:57

It's something I've I've toss back and forth. But I I

4:59

think if you do it well, one one thing I realized, I

5:01

don't know if you guys had this one. You had a few hundred

5:03

people you know, at a hundred people, you you

5:05

obviously don't have a hundred people reporting to you. You

5:07

have five to seven people reporting to you.

5:09

And someone pointed out to me at one point, they said, you

5:11

know what's interesting, Jesse? Once you're

5:13

at a hundred, you're never gonna have more people reporting

5:15

to you. It's not like the CEO of a

5:17

ten thousand person company has more than five to seven

5:19

people reporting to him or her. And so

5:21

I thought that was pretty cool. It's like, oh, no. You always

5:23

kinda have this team and and you're always

5:25

working with a team that you're leading and working

5:27

on. Obviously, there's more leadership as it gets bigger.

5:30

So I don't know. I I think I think I would

5:32

like to, you know, run something big and

5:34

large and unique and have a unique

5:36

culture around it

5:36

personally. That's so funny. As as

5:38

the resident introvert, I feel like you're gonna have

5:40

a different point view on this. Yeah. I

5:42

mean, I had a few hundred people and

5:45

I'm a zero to one founder.

5:47

It took me way too long to realize that and

5:49

I probably should have sold nasty gal along.

5:52

Before I raised Venture Capital because

5:54

it was an incredibly profitable successful

5:56

business. It's only

5:58

been in the last year that I've

6:00

realize that I'm good at starting things.

6:02

I'm amazing at starting brands. I

6:04

can rally people and get them to care about

6:06

and identify with what it is that I've created.

6:09

And scaling the brand I really love,

6:12

which I can do pretty nimbly,

6:14

but actually operating the business

6:16

is really challenging. For me. And

6:18

so over the last year,

6:20

I mean, I pretty much have a business

6:22

that is it's me

6:24

and I have an assistant and then I have

6:26

one person in New York. And

6:28

for the scale of the business, it may as

6:30

well be a one person business. I

6:33

think there's a great opportunity out there

6:35

now you can talk about this in greater

6:37

detail to for

6:39

creators to spin out more than

6:41

just, you know, YouTube

6:43

videos and TikTok videos you

6:46

can create an audience on those channels

6:48

and through the press, most of

6:50

how I became someone

6:53

who people follow wasn't because I was an influencer.

6:55

I got a following because I was doing

6:57

things mostly in the real world with the book and promoting

7:00

it. And a lot of inbound out

7:02

of, you know, not growing it through

7:04

creating videos. Video wasn't even a

7:06

thing on Instagram. And

7:08

from that, creators can

7:11

publish books. They can have patrons. They can

7:13

have memberships. They can have

7:16

private things for their communities. They

7:18

can you know, hosted,

7:20

you know, twitch, like, called

7:22

channel stream. Stream

7:25

events, books, there are so many opportunities

7:27

to monetize as a

7:30

business of one. I think

7:32

what becomes challenging any business

7:34

of one? Is that when it's successful? You

7:36

know, you spoke with Cody Sanchez. You

7:38

know, I interviewed Ryan Holiday

7:41

recently. All of these people,

7:43

you know, mister stoic, I'm

7:45

sure, started by himself. But

7:49

once something gets big enough, you

7:51

need people to help produce you because you're

7:53

creating so much content. You know,

7:55

the course creators, Amy Porterfield and

7:57

Jasmine Starr who have inspired me and

7:59

I've learned so much from, they

8:01

started, you know, an

8:03

online course, which feels like

8:05

maybe something that could be passive

8:08

income and really, you know, high

8:10

margins. But over time,

8:12

you really wanna scale that. It's challenging

8:14

to do without a

8:15

team. Yeah. I feel like the the

8:18

most successful solo printers turn into

8:20

entrepreneurs. Like, you're you're doing

8:22

a solo printer, until you

8:24

realize that something has enough opportunity to

8:26

not be a solo printer unless you've made

8:28

the very intentional choice. That you

8:30

don't want something to get above a certain size

8:32

because maybe it's just so profitable that you

8:35

hate actually everything that Jesse's talking

8:37

about, like leadership hiring

8:39

management and growing your

8:41

net worth by another

8:43

comma or another zero isn't worth

8:45

that work. And you just wanna continue to

8:47

print money with a lifestyle business. But

8:49

I just wanna double But I mean, hold on.

8:51

It's not a new concept though. I mean, one thing we should like,

8:53

I many many eons ago, I was a consulting

8:56

kid and a hedge fund hired us to project

8:58

the amount of domain names that would exist one

8:59

day. This is true story. And

9:02

do you know so, like, there's you know, you we'd look to

9:04

basically how many companies are in the

9:06

US. And so just

9:08

guess how many you know, there's there's four

9:10

categories. There's large corporations. Mhmm.

9:12

There's like mid side mid market. There's SMB.

9:14

And then there's what they call SoHo, which

9:16

is small office, home office, basically single person

9:19

Zero The original SoHo. How

9:21

how many of those you would you guess there

9:23

are? This was probably was the

9:25

last Two thousand

9:25

seven. Last group? Number four. Yeah.

9:28

Number four.

9:29

Sofia, you go first. Fifteen

9:31

years ago? Without

9:33

technology, without technology, are

9:35

we including consultants? It

9:37

just means that in the in the IRS, they say they're a

9:39

one person business. Five

9:43

million.

9:44

Eighteen oh, go. Sorry, shit. Eighteen

9:47

million. That's that is so much higher

9:49

than I was gonna guess. No

9:51

worries. I mean, just it's not an just

9:53

be clear. Right? I mean, this is the land of entrepreneurs.

9:55

Like, it's by the way, that number is probably, like, twenty

9:57

five now. All these creators and everything,

9:59

but it's not a new vehicle. It's not a

10:01

new thing at all to be a sales

10:03

entrepreneur. Yeah. I was

10:06

I agree with And I actually also think Solar Printer

10:08

for a lot of people is a misnomer.

10:10

Like, it's not I think there are very few

10:12

at least if you're talking about a

10:14

digital solo printer where it's

10:16

like truly one person, like I think a

10:18

lot of times it ends up turning into. You

10:21

have a VA in

10:23

the Philippines or you have,

10:25

like, an agency that's part time

10:27

helping with you. There's

10:30

a guy, and I sent

10:32

you this this article earlier, Pieter

10:34

Levels, who

10:37

I look at what he's done, and it's funny like

10:39

this is just the type of shit that gets me

10:41

very excited. He

10:44

has long he went through this project starting in

10:46

twenty fourteen of launched twelve

10:48

businesses in twelve months.

10:50

And a lot of it was to do

10:52

rapid testing, learn how to

10:54

test businesses to know if they're gonna reach

10:56

market fit or not and also to light

10:58

to not build for perfection and just put

11:00

things out into the world because he said that was a

11:02

big block for him. And

11:04

I don't think he actually ended up creating twelve BusinessBy.

11:06

He created seven. And they're

11:08

all over the map of what he created.

11:10

He created play my inbox,

11:13

which was a site that

11:15

would pull and because his

11:17

friends would share music with each other over

11:19

email, he would it would pull

11:21

email recommended music recommendations over

11:23

email, add it to like a single

11:25

website view where you can play all the

11:27

songs that friends had recommended to him.

11:29

He had one, this is my favorite, go fucking do

11:31

it dot com -- Mhmm. -- which was

11:33

you set a goal for yourself, you

11:35

set a date, and you send them out

11:37

of money, you're wage rate. And if you do

11:39

not hit that goal, you pay

11:41

the site for not hitting the

11:43

goal. And so that

11:45

was one he's actually his most successful

11:48

one. He has two really successful ones.

11:51

NoMad List and Remote Okay.

11:53

So he is a digital nomad. He's been traveling

11:56

all over the world, and so a lot of the things he's

11:58

built have been around kind of the digital nomad

12:00

remote worker lifestyle. Remote

12:02

Okay is simply a job board

12:04

for remote only

12:06

remote only roles and no mad

12:08

list is amazing it's organized

12:11

by city, how

12:13

good hundreds of cities in the

12:15

world are for digital nomads. So it ranks

12:17

on how is the community

12:19

there, weather, all these things. He does two

12:21

point he's gonna do two point seven million

12:23

dollars this year, and his

12:25

margin on his biggest business

12:27

is ninety four percent pretax. And

12:29

the only employees he has, he has

12:32

one customer support contractor

12:34

part time isabel. He

12:36

has a moderator for a Slack group because he

12:38

has a remote worker Slack group.

12:40

And then he has a dev ops guy

12:42

who's part time and that's it. And

12:44

so I I think it's

12:46

gonna be interesting for him once,

12:49

like, no madness or remoted k gets

12:51

big enough. Any has the option to

12:53

potentially scale those to ten million. What does he choose to

12:55

do? And that's why I think you only stay a solo

12:57

printer for so long. I think it's amazing

12:59

this idea of just like

13:01

the the gap between idea

13:03

to thing in the world just continues to

13:05

get smaller and

13:05

smaller, and I get so excited about that.

13:08

I think people consider

13:10

entrepreneurs to be people that have

13:12

businesses. Right? We that typically

13:15

owner sounds like someone who open a

13:17

laundromat or, you know, often kind of

13:19

like these family BusinessBy. And

13:22

today, everyone is an entrepreneur. Today,

13:24

everybody is a brand. Right? You're a

13:26

brow artist. Like, you have an Instagram

13:28

account and you, like, named your brow

13:30

artist business and you're the only person

13:32

doing it. Like, you're a lawyer. You're a

13:34

lawyer just for entrepreneurs and

13:36

you've got whole brand, Jesse, there's

13:38

a woman who we've worked with, who has

13:40

that. You're an SEO

13:42

expert. You're an agency, but it's just you,

13:44

but you wanna look bigger than you are.

13:46

Like, your dog walker, you're a nurse,

13:48

and you do Botox and filler. Like, your

13:50

Instagram is like, you're literally a

13:52

nurse, but your Instagram is like, look at

13:54

how good the lip filler that I can

13:56

do is -- Doctor -- -- sample popper. --

13:58

also content creators. Right?

14:00

Freelance creatives, designers. They're

14:02

an agency, and they're not scaling up

14:04

when they get a job. Like, they're doing the whole thing, but

14:06

they give it a website that has a brand

14:09

name, and this is all very

14:11

new, also that businesses

14:14

of one can market themselves

14:17

digitally in ways where it was

14:19

so much more fragmented and

14:21

you know, search was so much more

14:24

challenging, and you can discover these people on

14:26

Instagram. Instagram is incredible SEO,

14:28

by the way, which a lot of people don't talk about.

14:30

Yeah. For business. And if you optimize

14:32

your bio on Instagram,

14:35

someone's gonna type in brow artist and they're

14:37

gonna find you and they may hire

14:39

you, there's a lot of

14:41

themes that I think coming up that that are

14:43

interesting in in in what we're we're discussing. I

14:45

think one is, especially for

14:47

all of the it's

14:47

listening, like, man, there's just no

14:50

type of entrepreneur. You know, it's

14:52

like one of my like, they come at there's so

14:54

many shapes and sizes different

14:56

expertise, different scale, different desires, you

14:58

know. And I think that's a second thing, which is,

15:00

like, just decide what you

15:02

want and and go do it. You know, it's

15:04

not there's no right I think one of the things early

15:06

entrepreneurs, you know, a lot of people I

15:08

coach and talk

15:08

to, like, am I doing it right? Is this the right

15:11

way? And, like, so hard to let go of that and say,

15:13

no. No. There's no right. Just I mean, if you're you're

15:15

successful, do what you want. What do you

15:17

want this to be? Right? What what's your choice?

15:19

What are you trying to make it? I think that's

15:21

another one. And I think the thing Alex you pointed

15:23

out I kinda had similar experience last year for

15:25

myself. And and, you

15:27

know, Sofia, you said zero to one.

15:30

Getting that thing started is so

15:32

powerful. Like, it was a good lesson for me after

15:34

running a business for ten years. Like, I don't

15:36

know what these next three things will be worth. They

15:38

potentially might be worth all more than Ambrish after

15:40

two years, you know. Depending on how

15:42

you look at them. And there is a lot of

15:44

value in that just getting that

15:46

thing going, getting something going

15:48

And once I like, I started it used to be very precious. Like,

15:50

I think about how preciously I held Am Bush and

15:52

it was, like, my only company is the only you

15:55

know, I started three things and, like, people well,

15:57

it seems like you would know how to do that. You're pretty good

15:59

at it. Why don't and it it just really changed my

16:01

perspective on me. But I think for anyone listening

16:03

again, random job board,

16:05

random what like, there's so much power in

16:07

starting something. You know, operating

16:09

it as a different different sort of

16:10

animal, which I think is part of the the question here,

16:12

which is Do do you have to you can you

16:14

sell it? Do you can you sell entrepreneur it? Do

16:16

you find other people to run it? Like, there's all these

16:18

other questions, but there is a distinction

16:20

between getting that thing going

16:23

versus operating

16:23

it. Yeah. And I think the biggest thing is

16:26

just realizing there is

16:28

no right or wrong choice here for the longest

16:30

time I was this mental

16:32

loop of there is There was

16:34

one definition of success in

16:36

entrepreneurship. Even though it sounds

16:38

so ridiculous, and irrational

16:40

say, like, my subconscious

16:43

guided me to make decisions based on this

16:45

idea that I would not be a successful

16:47

entrepreneur unless I ran my business

16:49

forever. I stayed in the CEO role

16:51

forever. I took my business

16:53

public and anything short of

16:55

that would not be a success. And I

16:57

I think just to use the example of

16:59

Pieter levels again, like, there's

17:02

a lot of hard stuff about him being a sole

17:04

entrepreneur. Like, he had posted or he had

17:06

tweeted that he's started a bunch of

17:08

business now and is hit rates five

17:10

percent. So, like, it takes a ton

17:12

of that bats and it's exhausting. This guy's

17:14

coding all of his apps. But

17:16

on the side it, like, I think this deserves

17:19

airtime because I think if people just have this

17:21

perception that Elon,

17:23

this incredible guy who owns

17:26

Twitter and Tesla and

17:28

SpaceX is the North Star

17:30

for

17:30

everyone. It's not realistic and unfortunately I think

17:33

it'll disappoint people when they realize that their

17:35

body is at odds with kind of that

17:37

dream in their head.

17:38

Totally. By the way, the other She's

17:41

like, as a random aside, this

17:43

creator economy is gonna become a huge business opportunity

17:45

for people. Yeah. Like selling things

17:47

to people who agree. Oh.

17:49

A hundred percent honestly, we should do an

17:51

entire episode just on that, like, businesses to be

17:54

built for people who are

17:56

creators. I want to last

17:58

episode, Jesse, you had talked

18:00

about that one of your goals for twenty twenty

18:03

three was to

18:05

reduce your calendar by

18:08

twenty to twenty five percent and you said

18:10

you don't know how you're gonna do it, but it's

18:12

something that's important to you. I

18:14

want to understand how do you

18:16

guys spend your time and like, what do you prioritize? How often

18:18

are you thinking about shifting it? Because

18:20

I become obsessed with looking it's been

18:22

a recent trend on Twitter. Where,

18:25

like, top CEOs will share screenshots of

18:27

their calendars. And there's one guy who

18:29

I wanna get on to the show soon.

18:32

Who he he's, like, running a

18:35

billion dollar business and he have, like, four blocks

18:37

on his calendar in a given week

18:39

and one of the hosts called bullshit on it. I'm

18:41

not gonna say who. But

18:43

I'm interested in, like, how people think

18:45

about their calendars and obsessed with seeing these

18:47

screenshots. So how do you guys think about your

18:50

time? You, Josephia. Oh, man,

18:52

my time. Right now, it

18:55

feels really chaotic. I

18:57

think I talked about.

18:59

On the last episode, the kind of scope creep

19:02

that business class has

19:05

had moving from what felt

19:07

kind of like a solo, premier business to

19:09

something that I'm having to re

19:11

strategize right now. So right now, it

19:13

feels really out of role. And

19:15

there have been days this year that

19:17

haven't. And there I

19:19

think, often, it starts with

19:21

grounding yourself in the morning.

19:23

And I'm not the person who wakes up, you

19:25

know, I'm not the person who wakes up

19:27

at the crack of dawn, yawns,

19:29

and stretches,

19:30

like, see in the movie You're not

19:32

the four AM cold weather. Like perfect pajamas

19:34

with, like, my hair done

19:36

on Instagram. Right? And makes

19:38

their bed perfect. Sleep at eight o'clock most likely. Makes

19:40

them feel so good about their day and jumps in

19:43

an ice bath while

19:45

doing box breathing and using an ice

19:47

roller on their

19:47

face, and then sits in silence for

19:50

an hour, drinking their tea, and

19:52

journaling, and then meditating. You don't add

19:54

all memorized by these people. I

19:56

think it's a scam.

19:59

III think it's really

20:01

dangerous to inspire people

20:03

with a life dial room morning

20:05

that takes three hours and,

20:07

you know, unless you can go to bed

20:09

at nine PM, it's not possible for

20:11

most of us, and it makes most of us feel

20:13

bad. Half of us are inspired by it. And

20:16

then the other half of us are like, How is

20:18

that even possible? What am I doing wrong? How could

20:20

I even have a productive day if that's

20:22

not how I'm starting it? But I've

20:24

done kind of glimpses of that in this

20:26

year, the days that really grounded me or

20:28

going to yoga at seven thirty in the

20:29

morning, like, out of bed at six forty five.

20:31

I'm driving like So you just said

20:33

you hate these people, and now you're saying you don't.

20:36

Literally, just yoga. It's just yoga. If

20:38

you can do if you can

20:40

do, like, realistically, if

20:42

you can do one thing at the beginning of your

20:44

day that grounds you and makes you feel

20:46

accomplished. That's it. You do you I

20:48

do yoga at seven thirty in the morning.

20:50

I shower right afterward because there are showers

20:52

there from eight thirty to nine. And then

20:54

there's a blue bottle nearby and I go, like,

20:56

jack up my system on, like,

20:58

two, like, you

21:00

know, double shots of,

21:02

you know, cappuccinos and then I'm home by

21:04

ten or I take phone calls from blue

21:07

bottle. And, I mean,

21:09

what I would like to do is stack my

21:11

calls do more than, like, two hours a

21:13

day. But I22 hours at a

21:15

time and taking short breaks in

21:17

between. And for

21:19

the second half this year. I have

21:21

had days where I don't have

21:23

calls and days where I

21:25

do have calls and that's been

21:27

amazing. Right? Fridays, We record the podcast. I

21:29

actually shower and put makeup on.

21:31

So after this, I'm gonna go make content

21:33

and do some Instagram rails and just take

21:35

advantage of the fact

21:36

that. Like, I'm not wearing pajamas because I

21:38

work from

21:39

home, but

21:40

not every day's like that.

21:42

Well, just just to ask a question

21:44

around kind of like the more macro level and

21:46

then we'll dive in. How many hours a week do

21:48

you think you're

21:48

working? You want

21:51

to look? Yeah. Probably like

21:54

forty. I mean -- Okay. -- thinking

21:56

about it, it's like a

21:58

hundred. But that's just

22:00

anxiety. So so let's

22:01

say it's forty. Anyone property.

22:03

How

22:03

much of that how much of those that

22:06

forty do you think is business class?

22:12

686 hours. It

22:15

feels like so much. Well, that's

22:17

on calls, probably, like, five hours of calls, and then

22:19

there's so much inbound copy,

22:23

design, kind of, like, approvals of

22:25

communications students

22:28

writing my

22:28

newsletter. That's kind of

22:29

Yes, sir. How much do you think all of that is?

22:33

Maybe, like, ten hours, but it feels, like,

22:36

a a hundred for some

22:38

reason. And then

22:38

-- Interesting. -- I also talk to entrepreneurs and

22:40

make investments. I create content

22:42

we record the podcast, you know.

22:45

I do calls on the intro app and

22:47

mentor people. I'm working with an

22:49

ads team for business class

22:51

and reviewing you know, you

22:53

know, creative for that and

22:55

updating copy. I still write

22:57

pretty much all the copy because I

22:59

cannot figure out how to delegate

23:02

my voice. You know, I'm doing

23:04

influencer stuff. I have a partnership with Notion,

23:06

a partnership with SurveyMonkey,

23:08

a partnership with PMI International,

23:10

which is a project management organization, like, that's

23:13

all that's going back and

23:13

forth. It goes So you have a lot of It's a lot of

23:16

context switching. Yeah. I was gonna say it seems like you

23:18

have a ton of context switching. So

23:20

Yeah. First of

23:23

all, are there any things that you do to

23:25

your calendar to try to make

23:27

context switching easier? Like, are you

23:29

working on all of these things of

23:31

the week? Are you blocking out certain

23:33

times for the type of work that's most annoying

23:35

in your day to get that done

23:37

first? Like, do you do anything to help yourself with all this

23:40

switching? I put on my

23:42

calendar, you know, after this, I'm

23:44

gonna record content. If

23:46

I if something's due to

23:48

a brand that I'm creating

23:51

for a partnership, like that's on the

23:53

calendar. And if I have to create content for

23:55

that, and it's due on Wednesday, Monday.

23:57

It's on my calendar and my assistance

23:59

here, and he, like, is amazing,

24:01

Tyler, and helps me,

24:04

kind of, organize myself, prepare for that. We're looking at, you

24:06

know, hashtag, you

24:08

know, add all the things that you

24:10

have to draft. There's such a level of

24:12

detail for that stuff. But

24:15

right now, I would probably ask advice

24:17

of you too on how I

24:19

could better optimize that because

24:21

as an ADD entrepreneur

24:24

with a lot going

24:27

on, I think I could use some

24:29

inspiration. Jesse,

24:30

what do

24:30

you think? Advice or

24:32

you wanna hear what I do? So

24:35

it's somewhat the same.

24:36

Yeah. Maybe care what you Maybe I don't

24:38

know. Everyone everyone has to figure their own

24:40

think, I mean, the the advice like, I've learned to

24:43

become much more gentle with myself over

24:45

time. I think a year or five years

24:47

ago or seven years ago, I was like, gah,

24:49

you did a new lady. Bad day,

24:50

Jesse. He'd look at he'd look at

24:52

the mirror and slap himself and then go back to A

24:54

version of that. And I think over time, I'm

24:57

like, You know what? Like, and and it's something I try to coach everyone I work with,

24:59

especially the younger entrepreneurs. I'm like, hey,

25:01

you know, you got a bunch done this

25:04

week. Like, Did did did the ball

25:06

move forward? Did it go did it not

25:08

go backwards? You know? And and I I love the

25:10

pushing of Boulder up a hill analogy. I'm like, you know what?

25:12

If you're pushing a Boulder up a hill, you keep

25:14

it in the same place or get it forward a little bit,

25:16

that's progress. And like as long as it doesn't go

25:18

back, you're good. And so I I think

25:20

in general for anyone kind of

25:22

attacking these sorts of things, I think you gotta be real

25:24

gentle and sort of doesn't mean you wanna get

25:26

better, you can learn things. But to me, that's like

25:28

the I think that keeps people frozen

25:30

out the most because they just they freak

25:31

out, you know, so tough on

25:34

themselves about it. And I was like that and still am in

25:36

some ways, but And so how do you

25:38

approach given that you're, you

25:40

know, you have your

25:42

company and push that you're not

25:44

actively involved with, but it's your, you know,

25:46

it's your baby. You have your three businesses

25:48

within GatewayX. Like, how are you

25:50

thinking about strategy around

25:53

time?

25:53

Yeah. Yeah. You know, if I I don't wanna post

25:56

one of those calendar things because I can't

25:58

brag about time. I will say, know,

26:00

interesting. I my

26:03

calendar is very busy even

26:05

beyond the work hour, and I'll walk through it in a

26:07

second. I you know, I'm

26:09

a little torn because on the one hand, I get a

26:11

lot done. And and I and I don't

26:13

just mean again work stuff. Like, I

26:15

play tennis three times a week. I like

26:17

hang out. I put my kids to bed four or five nights a week. Like,

26:19

I do a lot. And I'm not generally

26:21

an organized person, but, like, that's

26:23

one area where people are always like, damn,

26:26

just like, because people know me in life and I miss

26:28

flights and all this stuff, they're like, damn, you're calendar.

26:30

But, wow. You oh, I've

26:32

missed ten percent of my flights as a

26:34

life

26:34

rule. You're spending too much time in airports if you don't.

26:36

I still see

26:36

my droplets myself. Yeah. I would not have

26:38

guessed that, but sorry, continue. So but

26:40

but, anyway, you know, I

26:42

I am torn, but at the same time, sometimes it feels

26:45

overly

26:45

scheduled. So, yeah, let me give

26:48

you my week. I'd

26:50

say so a couple different things. I know

26:53

you've been asking, Alex. So one

26:55

is I've tried now on

26:57

Mondays and Fridays. I do other

26:59

business interests. for Kahani in

27:01

particular, I'll do the kickoff for the week and the

27:03

major, you know, what what's the meeting?

27:05

You know, what's the plan for the week or

27:07

the sprint? various teams doing in

27:09

sales marketing? What what do we have to get

27:11

done? So basically and then in addition,

27:13

I'll meet with the other leaders of the

27:15

other businesses mondays and Fridays only. So Tuesdays and

27:17

Thursdays, they're blocked by calendar. There has

27:19

to be a very good reason for me to come

27:21

off that. Which is something that, you

27:23

know, post raising money and kind of focusing

27:25

on being the CEO there is something that I did differently.

27:27

Doesn't mean I won't spend time on those things,

27:29

but in general, it's a good forcing

27:31

function. To avoid that context, which

27:33

I have a lot. My

27:36

general workday I'd say is, like, well, it's

27:38

a little different. So Monday, Wednesday, Friday,

27:40

it's, like, eight thirty to

27:42

six or six thirty. I'm home by six thirty. I

27:44

do dinner and I'm like, I'm on

27:46

kid night duties, you know, Monday and

27:48

Wednesdays and Fridays and

27:51

Sundays. Tuesday, Thursdays

27:53

are my late days, so I usually work, like, eight

27:55

thirty to seven thirty or eight. I don't I

27:57

usually don't see my kids. Sometimes I'll just say good

27:59

night to them. I play on Tuesdays and Thursday evening, like Sofia

28:01

called me yesterday as on the courts. And

28:04

so those are my tennis days. I

28:06

usually do try to work out on Wednesdays

28:09

I have date nights, Wednesday, Saturday with my

28:11

wife that are just kind of like, though, again, those are we

28:13

don't change them very often unless we have to Friday

28:15

nights, pizza night with the kids.

28:17

And I

28:19

mean, you seem very routinized.

28:21

Very very routinized. Yeah.

28:24

Big time. And I think when you have that many

28:26

stakeholders, like, again, not just in the business side, but

28:28

on the people side. And then in terms of how

28:30

I spend my business time, I think I've tweeted and

28:32

stuff about this, you know, one thing I learned from at Red

28:35

Ventures, he he doesn't like standing

28:37

meetings and I I try my best actually. I'm not

28:39

like that dude who put two hours and, like, I have

28:41

nothing I mean, like, But

28:43

in general, like, I I try to avoid

28:45

standing meetings, and the reason is is because

28:47

what's important this week or for the next

28:49

week or two is gonna be very different than what's

28:51

important in the following two weeks. And I

28:54

like to change and shift my hour, like where

28:56

I spend my time, depending

28:58

on where I need to be, you know, what needs to be

29:00

getting done in that time. And I think being that, like,

29:02

a mistake I see a lot of founders make is that

29:04

I made this early on was

29:06

my calendar inside of those blocks being too routinized.

29:08

I have take this at this time, then we have to meet on this. And

29:10

that's when you start creating meetings that people show up

29:12

just to present something that they don't actually have anything

29:14

instead going, hey, let's let's grab time

29:16

on this. This thing looks really important. We should talk about this in

29:19

right now. And this other thing, let's push

29:21

that out. So I do try to be very dynamic. So every

29:23

Sunday, I spent an hour or two kinda

29:25

planning my

29:25

week, trying to figure out what I should spend time on,

29:27

where I should go deep, where I should spend time. I'd say

29:29

the biggest thing I'm trying to work on for

29:32

next year I don't do

29:34

a lot of work. Like, I'm pretty scheduled

29:36

from nine to six or nine Like,

29:38

meaning I'm taking meetings with people

29:40

almost constantly, internally and externally. It hasn't

29:42

doesn't leave room to do any work, like and then

29:44

actually things like I can write or things that

29:47

And so I'm trying to get better at actually with my assistant blocking

29:49

off

29:49

time. I was just about to ask about

29:52

that. Like, do you have time for

29:54

any time for deep work, like just even

29:57

thinking, high level about your three

29:59

businesses. Week I

30:01

mean, weekends, I'll do it. Like, I Sundays,

30:03

I usually work for about five or six hours. I'll to

30:05

get some stuff done then. I'd I'll come back

30:07

online at night, like, after my everyone's

30:09

asleep in my house, usually for an hour

30:11

or two. That's usually for email. But sometimes,

30:13

it'll be I wanna sit down and write something

30:15

out. I want you

30:17

guys know I'm a pretty off the cuff thinker,

30:19

so a lot of my thinking happens, and it'll it'll just

30:21

come through me. Like, it'll be something that's, like, sitting in

30:23

the back of my brain. Yeah. And I'm, like, oh my god, I

30:25

gotta write this down. There's something really important happening here

30:27

just like keep a neutron in your But I wanna get better at,

30:29

like, blocking off ten hours a week

30:31

of work of

30:34

things I to get done. So that's that's why one

30:36

of the big improvements. One last question for

30:38

you is not

30:41

that they've said this, but what

30:44

would you say if

30:46

a kahani investor was

30:48

like, dude, you're you're the CEO of

30:50

this you have just two days a

30:52

week focused on Kahani. 333

30:55

and a half. thought it was Tuesday, Thursday. Tuesday,

30:57

Wednesday, Thursday. Okay. Got it. Got it. Yeah.

30:59

So you have to make a half a half day on

31:01

Monday. Yeah. Oh,

31:02

so so so it's, I guess, the majority

31:04

of your week. Yeah.

31:07

It's definitely the majority. I mean, look, you gotta make

31:09

these you gotta get clear with people upfront on what's

31:11

going on and what's like in my doc. Commons are all these

31:13

other businesses. They're aware of my roles there. They're not

31:15

they're not naive that, like, this is and

31:17

and it's part of what it's, you know, you take the

31:19

good with the whatever, with the opposite. Like,

31:21

they know the benefits of being involved, and they know the costs,

31:24

and so yeah. I think I think they need to pay

31:26

attention to the ARR and how I'm growing the business, and I'm

31:28

doing a shitty job. They should fire me. And if I'm

31:30

doing a great job, they should you know, be really

31:32

happy. Yeah. That makes

31:33

total sense. I don't have any doubts

31:35

that Jesse has time

31:37

to think or doesn't need time

31:39

to think. Just knowing how

31:42

little Jesse has to prep for

31:44

this podcast and the kind of

31:46

wisdom that just flows out

31:48

of his mouth. I

31:51

I have a feeling it happens. Yeah. Like,

31:53

his attitude He's just he's just a walking

31:56

epiphany. I Well, in the

31:58

sessions of time and it's like, I'll

32:00

you can make time to think in those meetings.

32:02

Hey, guys. What's a big challenge we're having?

32:04

What's it, like, to me get during during a

32:06

meeting itself is, like, a really important piece of

32:09

this, which is we actually like,

32:11

we've started doing it as a rule now. We breathe for thirty

32:13

seconds before the meeting. We do a

32:15

box breath to make fun of the earlier

32:17

thing. We start meetings with box breathing, and then

32:19

we go, okay, what what do we wanna do here? What are we trying

32:21

to get accomplished? We don't do it

32:23

perfectly, but it's really valuable to do that in the session itself.

32:25

I I love that. I actually know

32:28

a friend of

32:30

mine part of her consulting business is

32:32

helping like fortune five hundred companies, like

32:34

coaching them up in more present

32:38

meetings by doing the exercises

32:40

you just talked about before every single

32:42

meeting. And I I remember I I asked

32:44

her I was like, how do people if

32:46

you're going into like Apollo or

32:48

KKR and you're about to tell this MD, hey,

32:50

I want you to breathe in for three seconds.

32:52

Hold it for three seconds.

32:54

How for three seconds. Hold it for three

32:57

seconds. Like, I would love to be a fly

32:59

in the wall seeing that MDI

33:01

KKR respond to you wanting them to do

33:03

that breath. But like it is so important. But they're

33:05

still human and every human knows that when

33:07

they're present and they're there, they can be much

33:09

more capable power thoughtful --

33:12

Totally. -- and when they're not, they can't be. And and and I I

33:14

think that by the way, the bet the best

33:16

thing about box reading is it's the easiest thing to

33:18

convince someone of doing because within

33:20

thirty seconds, they do it and they go, wow, this

33:22

is better. Yeah. It's like the

33:24

easiest thing to convince someone of because it it's such

33:26

an immediate gratification when

33:28

you breathe. Totally. I just wanna share

33:30

a few parts of

33:32

kind of how I spent my time because it's changed so much

33:34

over the last few

33:35

years. And I I'm

33:38

very ADD like my

33:40

brain is all over the place. And

33:42

so I'm constantly thinking about how

33:44

do I

33:46

how do I wrangle like the madman,

33:48

but also respect kind of

33:50

the value of my brain?

33:53

And so just a few things that

33:55

I do. Don't start anything before

33:57

nine AM because if I don't get

33:59

my morning routine in, it throws off

34:01

my entire day. And just

34:03

my morning routine very simply.

34:05

Is it's like seven fifteen

34:08

wake up. Feed

34:10

my dog. Take my

34:12

dog out for With my

34:14

fiance, come back in, have a

34:17

coffee, and then go and do

34:19

a workout, and then I start

34:21

my day after that. And just any day I

34:23

miss that, I just don't

34:26

feel as good. Like, it doesn't ever feel as

34:28

good for me to do a midday workout for

34:30

whatever reason. Then similar to Sofia, I try to lump

34:32

as much content creation together as I can.

34:34

Send it everywhere. Like, I try to lump

34:36

together similar

34:38

skills So I try to do

34:40

a similar type of action around the

34:42

same time. So, like, sixty seconds start up

34:44

my social series. I'll do a dozen of those at

34:46

once and do try to do impostors and

34:48

TCO on the same day, so I do those things together, and then I try

34:51

to just batch everything. I try

34:53

to get to bed

34:55

before eleven o'clock, because if

34:57

I don't do that, it throws off my entire

35:00

next day because I really try to get seven to eight

35:02

hours if I can.

35:04

People Another thing I'm working on is sleeping

35:06

I'm not an early sleeper. Yeah. It just what hap what honestly

35:08

ends up happening is I end up sleeping

35:10

later because I want it I

35:13

need to get sleep, and then I won't do my morning workout. Like,

35:16

that's the trickle down effect.

35:18

I've found that I'm way more ADD in

35:20

the afternoon. Like for whatever

35:22

reason, when two or three o'clock

35:24

hits, I just get less productive.

35:26

And so I really try to have pre

35:28

two o'clock be my more

35:30

productive hours. And I I would say like the hardest

35:32

transition that I found when I switched from

35:34

working at Morgan Stanley

35:36

to going

35:38

full time morning Brew and then the transition I made from running the day to day

35:40

morning Brew to being the chairman is I went

35:42

from every minute of my day was

35:44

dictated for

35:46

me. To every minute my day was not dictated

35:48

for me. So like at Morgan Stanley, it

35:50

was six thirty to seven thirty PM,

35:54

I am staring at a screen doing trades for

35:56

thirteen hours. I went in went

35:58

full time on morning brew and there was all

36:00

of the possible things to do on the BusinessBy.

36:03

But there was literally zero in my calendar.

36:05

And that is an incredibly daunting

36:08

thing. That same exact thing happened when I

36:10

went from CEO to chairman. And so it's something I'm

36:12

still trying to work through. So those are some of the

36:14

things I do to just manage my scale schedule.

36:18

What what gives you the most energy

36:20

and what is the least energizing.

36:22

I would

36:23

say the most energizing things

36:26

for me

36:28

are build

36:30

zero to one, like building things I'm

36:32

really excited about. Like, I've sent you

36:34

guys this backyard game I'm playing in, like,

36:37

that I'm making and, like, the

36:39

process of talking to the

36:41

industrial designer about the design of

36:43

the game and getting

36:46

videos from the manufacturer

36:49

in China throwing

36:52

the plungers at

36:54

the game. Like, to me, that

36:56

energizes me. Like, you guys know I

36:58

recently built this free startup database

37:01

where I just curated my favorite startup resources on

37:03

the Internet, like going through the process of

37:05

figuring out what no code tools to use,

37:07

how to connect Zapier

37:10

to, like, It's just it's just like the the real

37:12

life, call it, like, hopefully money

37:14

making versions of,

37:16

like, Legos. Like, that's the

37:18

part I enjoy doing, and I really enjoy creating

37:20

content. So

37:22

going back to last episode as I think about

37:24

next year, it's just like, I want more of that in

37:26

my life. Okay. Let's let's move

37:29

on to the final topic.

37:32

And the final topic

37:34

today is a little bit of a

37:36

meta

37:36

one. I've been spending a

37:39

lot of time recently thinking

37:41

about how can we just keep leveling

37:44

up the show how can we go

37:46

from you know, right now, we're let's call

37:48

it getting twenty thousand downloads

37:50

an episode on the

37:52

show to you know, how do we to fifty thousand downloads soon as

37:54

possible? And on the video, how do we grow our

37:56

YouTube channel faster? So

37:58

beyond just creating better content

38:01

always. Like, to me as a media mind, like, that is

38:03

always gonna be number one. Create better content and

38:06

good things happen. But how do you guys

38:08

think about what we can do to improve

38:10

the show in the New Year, have it grow

38:11

faster, like, no bad ideas. What do

38:14

you guys think?

38:16

Do we do longer episodes? Longer

38:19

and more free

38:22

of work. Well, look, again, let me combine it

38:24

longer and more free. Like,

38:27

more just, like, a little bit

38:29

more riffing, a little bit less, just

38:31

sort of, like, us the three of us

38:33

making little speeches. Mhmm. I

38:35

will say,

38:35

Jesse, you are very consistent in your

38:38

feedback. You you have been very

38:40

consistent since day one about kind of what you

38:42

envision for

38:42

this, which isn't a bad thing, but it's

38:45

just an observation.

38:45

I like, you know,

38:48

today, and in our last show, we're talking

38:50

about a little bit more evergreen topics

38:52

like how to set goals.

38:54

You know, side side hustles and how that is different

38:56

from, you know, starting a business

38:58

or what it's like to be

39:02

you know, a business of one and who is that right for. I

39:04

think sometimes we get into really

39:07

complex stuff that for the

39:10

average listener, maybe harder to

39:12

grasp, where we may be

39:14

throwing in acronyms or

39:16

talking about arbitrage

39:16

businesses, which -- EBITDA. -- EBITDA,

39:18

which is okay. We should talk about

39:20

we should talk about business finance, but

39:23

I think throwing out terms without first

39:26

demystifying them for the person in the

39:28

room who may

39:30

not know keeping a

39:32

headset on for that person and listening

39:34

for them is really important and just making sure

39:36

that we're answering their questions before they have

39:38

to ask them. And I

39:41

think we could I

39:43

think having guests once in a while,

39:45

which we have is also

39:48

just a fun way to grow it -- Totally.

39:50

-- because we use that platform, but

39:52

also a way to get a different perspective on

39:54

some of the things that we've even already talked

39:56

about because everybody's gonna have a different point of view. If

39:59

you guys could have one guest

40:01

who would it be? Who

40:04

comes

40:04

to mind? Jeff Bezos. I don't know. Are we what are

40:06

we are we gunning for big here? Yeah. Yeah.

40:08

Anyone anyone. So okay. Bezos.

40:11

Sofia, who would you pick? I

40:14

think, like, Mark Anderson

40:17

or, like, a top VC

40:19

talking about what

40:22

entrepreneurs look like. Someone who's

40:24

kinda seen it all and seen who wins

40:26

and who loses and how they

40:29

think about entrepreneurs from

40:32

the ten thousand foot foot

40:34

perspective of someone who literally

40:36

sees everything out

40:38

there. And how they

40:40

pick what they think are gonna be

40:42

winners. I think it'd be fun to play play with

40:44

different formats, by the way, like me and

40:46

Sofia only. No Alex or Alex

40:48

and

40:48

Sofia, you know, Just Sofia, just

40:50

Jesse. It would be fun to just play around with

40:52

that. Totally. By the way, that's one of the things

40:54

that I had down, which is I

40:56

think testing formats. So, like, bring back

40:58

the Solo Founders Journal style where it's basically like a

41:01

ten minute journal entry by us as

41:03

like interesting shit is happening in

41:05

our businesses or test out

41:07

a differentiated interview format, whatever that looks

41:10

like, or shorter episodes around a

41:12

specific evergreen topic. Like, for

41:14

example, if we did

41:16

something around I don't know, like end of year

41:18

reviews or if we did something

41:20

around wartime

41:22

leadership. Like

41:24

I I've been thinking to myself if we do a fifty minute episode

41:27

and that fifteen minute piece

41:29

is in the middle, it may not

41:31

be the most efficient thing. The

41:33

person who's looking for, like, wartime

41:35

leadership lessons, they would just wanna find that

41:37

single episode. So, yeah, I think playing around

41:39

with formats for sure makes sense. Or I don't know. I

41:41

would love to, like, even have,

41:44

like, an actual recording

41:46

of you guys running a meeting

41:49

with your

41:49

teams. So people can actually be like making up or be a

41:51

flying the wall listening to how Jesse runs a meeting with

41:53

his teams. Yeah. I think each

41:56

of us

41:57

you know, we could divide and conquer in some ways

42:00

where, Alex, if you wanna talk about

42:02

something more news

42:04

oriented or topical or may

42:08

be complex that I,

42:10

you know, may have a harder time contributing

42:12

to because I have a different

42:14

zone of

42:16

genius, like, I'm happy to have a conversation on

42:18

my own about that or interview somebody.

42:20

You know, I interviewed people for five years on

42:22

girl loss

42:24

radio. So tag teaming I mean, also, it's

42:26

like yeah. It's like, I can do that

42:28

on a Friday, and you can

42:31

do it three weeks later, or you can

42:33

do a mini episode or

42:35

lesson. And by the

42:36

way, that's how much how we create more surface

42:38

area. Right? Like, we have one app

42:40

a soda week on the feed right now. Like, what it look like to get

42:42

to three? But not with, like, three times the

42:44

amount of effort. And I think that's that's

42:46

possible. I'm game. I'm game. I

42:50

love it. Yeah. You guys took all

42:52

the good ideas. I think that's awesome. Well,

42:54

the reason this was a

42:57

meta discussion is because wanna hear from

42:59

the audience now. I wanna hear from the So for those

43:02

listening or watching this episode of the crazy

43:04

ones, we wanna hear from you. What

43:06

formats do you

43:08

want us try in twenty twenty three. How do you think the show could be

43:10

better? Or what ideas are there for growing the

43:12

show that maybe we haven't thought of? Shoot us an

43:14

email at the crazy ones at mourningbird

43:16

dot com. And if you'd

43:18

be so incredibly kind to give

43:20

us the gift

43:22

of subscribership. I wish I wish

43:24

I had a better word for that. Sharing it.

43:26

Share it if if it's valuable for

43:28

you.

43:29

Yeah. No. No. If if

43:30

you guys would be so kind to give us the

43:34

gift, sharing, subscribing,

43:36

reading, and