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RWL237 Business Adaptability in Remote Work with DeskPass CEO, Sam Rosen

Discover how Sam Rosen, co-founder and CEO of DeskPass, turned a pivotal moment in New York into a global movement redefining where and how we work. Sam’s journey from designing in Chicago to building a flexible workspace marketplace will inspire you to rethink traditional office environments. 

Learn how his unique blend of creativity and technology insight has driven DeskPass to become a leader in connecting companies with diverse workspace solutions worldwide. 

You’ll also learn DeskPass’s strategy for standing out in an increasingly crowded market. From offering a variety of workspace options in both bustling cities and quiet rural areas to adopting a user-focused design and flexible pricing model, DeskPass is revolutionizing the way businesses approach workspaces. Sam shares his business’s hiring practices that ensure cultural fit and reveals the keys to building a great team. 

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Global Solutions for Remote Working

Alex
0:00

This

is

the

Remote

Work

Life

Podcast
.

Yes
,

it

certainly

is
,

and

I'm

your

host
,

alex

Wilson-Campbell
.

Thank

you

so

much

for

joining

me
.

Have

you

ever

found

yourself

trying

to

find

somewhere

to

work
,

somewhere

that's

comfortable
,

somewhere

you

feel

you

can

be

at

your

most

productive
,

and

somewhere

that's

got

good

Wi-Fi
?

Well
,

today's

guest
,

sam

Rosen
,

is

co-founder

and

CEO

of

a

business

that

has

solved

that

problem

on

a

global

scale
,

and

the

origin

story

of

the

business

is

something

to

certainly

listen

out

for
,

as

is

the

refreshing

way

in

which

his

team

goes

about

the

hiring

process
.

So

listen

up

and

enjoy

today's

episode
.

Today's

episode
.

Sam Rosen
0:44

So

I

am

based

out

of

Chicago

and

I

am

the

co-founder

and

CEO

of

DeskPass
,

which

is

a

marketplace

that

helps

connect

companies

and

the

folks

who

work

at

those

companies

with

flexible

workspaces

all

over

the

world
.

So

that

includes

desks
,

meeting

rooms

and

offices

all

available

by

the

hour
,

up

to

month

to

month

to

month
.

I'm

based

out

of

Chicago

and

have

a

nice

little

family
.

I

live

in

a

little

town

called

Oak

Park
.

Sam Rosen
1:16

I

came

into

this

industry

as

a

designer
.

Before

this
,

I

started

a

design

firm

called

One

Design

Company

here

in

Chicago

that

does

work

all

over

the

world

for

all

sorts

of

really

interesting

clients
,

and

so

my

background

has

always

really

been

the

intersection

of

design

and

technology

and

because

of

that
,

I

came

across

co-working

really

really

early

on
,

when

there

are

about

300

spaces

in

the

world

that

call

themselves

a

co-working

space
,

and

my

on
,

when

there

were

about

300

spaces

in

the

world

that

called

themselves

a

co-working

space
,

and

my

partner

at

the

agency

and

I

opened

the

first

co-working

space

in

Chicago
.

So

I

have

a

really

interesting
,

I

think
,

perspective

and

there's

probably

30,000

plus

workspaces

to

just

this

change

in

how

we

work

and

where

we

work
,

and

I've

always

really

taken

it

from

just

a

perspective

of

humans

and

design

and

human
,

just

how

we

work

and

how

we

think

about

living

our

best

life
.

Alex
2:18

Next
,

can

you

describe

a

personal

story

or

experience

that

has

influenced

who

you

are

today
?

Sam Rosen
2:24

a

personal

story

or

experience

that

has

influenced

who

you

are

today
.

Well
,

to

this

question

is

how

I

came

across

co-working

and
,

like

I

mentioned
,

I

owned

an

agency

or

still

do

and

I

got

to

travel

a

lot
.

There's

probably

like

less

than

10

of

us

and

I

was

traveling

to

New

York

a

lot

from

Chicago

and

I

was

living

out

of

when

I

was

there
,

out

of

my

girlfriend's

apartment

and

she

was

super

cool
.

She

had

a

horrible
.

She

had

a

garden

apartment

with

a

thin

layer

of

clothing

always

on

the

ground

and

very

bad

internet

and

very

bad

cell

phone

coverage

and

we

actually

had

the

biggest

pitch

that

we

had

to

date

and

I

was

kicking

off

the

engagement

and

I

don't

know
.

I

dropped

the

call

like

five

plus

times

and

my

colleague

at

the

time

was

like

dude
,

you

can't

do

this

anymore
,

you

need

to

get

your

shit

together
.

Sam Rosen
3:18

So

I

did

what

any

I

think

New

York

hipster

would

do

is

I

found

a

cool

cafe

that

was

down

the

street

called

the

rabbit

hole
.

I

always

love

the

names

in

these

stories

and

I

would

work

out

of

the

rabbit

hole

all

day
.

Honestly
,

didn't

have

much

better

internet

and

much

better

cell

coverage

and

they

clearly

didn't

want

me

to

work

there

because

I

had

a

table

tent

that

would

say

would

say

no

working

during

lunch

rush
.

Then

the

power

stopped

working

and

they

turned

off

the

Wi-Fi
.

So

I

was

trying

to

find

a

solution

and

that

same

colleague

said
,

hey
,

have

you

ever

heard

of

co-working
?

And

I

said
,

well
,

I

think

most

people

said

at

that

time

which

was

co-what
?

And

there

was

like

one

co-working

wiki

that

had

all

the

co-working

spaces

in

the

world

about

300

of

them

and

one

was

in

New

York
,

a

few

blocks

away
,

and

I

decided

to

give

it

a

try

and

the

name

of

that

place

at

the

time

was

the

Change

you

Want

to

See
.

Sam Rosen
4:11

So

I

ended

up

with

the

Change

you

Want

to

See

and

showed

up
,

had

no

idea

what

I

was

getting

myself

into
,

and

the

guy

said
,

hey
,

are

you

here

for

co-working
?

And

I

said

yeah
.

He

said

okay
,

great
,

and

helped

me

to

get

myself

comfortable
.

I

had

a

few

rules

to

be

respectful
,

to

not

take

over

too

much

internet

and

at

the

end

of

the

day
,

if

you

liked

the

experience
,

to

drop

a

tip

in

the

tip

jar
,

girlfriend
,

and

were

in

design

and

media

and

entertainment

and

just

really

absolutely

fell

in

love

with

this

idea

of

collaborative

working

and

working

with

people

other

than

your

colleagues
,

but

together
,

and

I

looked

to

see

who

is

doing

this

in

Chicago

and

the

answer

was

nobody
.

But

there

were

already

people

who

signed

up

saying

I'd

be

interested

in

this

space
.

So

my

partner

and

I

decided

to

give

it

a

shot

and

that's

really

like

the

origin

of

how

I

found

co-working

and

that

really
,

I

think

has

been

quite

instrumental

in

my

path

since

then
.

Alex
5:14

As

you

look

back

on

your

life

and

connect

the

dots

that

led

you

where

you

are

now
.

What

are

those

dots
?

Sam Rosen
5:23

Like

when

I

think

about

answering

this

question

it

always

comes

to

me

back

to

how

I

was

raised

and

I

have

a

really

fabulous

family
.

My

mom's

a

painter
,

my

dad

directed

television

growing

up

and

was

in

production
.

So

I

always

kind

of

grew

up

in

this

like

mix

of

art

and

production

and

media
.

That

has

really

guided

a

lot

of

how

I've

thought

about

and

I've

always

been

very
,

very

entrepreneurial
.

So

since

I

was

a

little

kid

I've

always

had

some

type

of

racket
,

whether

it

be

like

self-publishing

or

doing

website

design

or

just

trying

to

find

ways

to

add

some

value
.

That

led

to

the

design

agency
,

which

will

be

20

years

in

January
,

to

the

design

agency
,

which

will

be

20

years

in

January
,

and

the

design

agency

has

really

shaped

a

lot

of

how

I

think

about

the

world
.

Sam Rosen
6:11

I've

been

able

to

learn

a

lot

about

different

industries
,

always

sort

of

thinking

about

how

great

design

and

great

brand

intersects

with

really

interesting

upcoming

innovative

technology
.

So

that's

really

been

sort

of

the

bedrock

of

how

I

think

about

things
.

And

then

I

just

kind

of

right

place
,

right

time

came

across

workspace

and

this

was

a

long

time

ago
,

15

years

ago

but

it

was

always

pretty

clear

to

me
,

using

sort

of

this

frame

of

knowledge

that

how

we

work

and

where

we

work

was

backwards
.

It

wasn't

oriented

around

the

people

who

are

the

workers
.

It

was

oriented

around

their

boss

or

the

building

owner

or

the

bank
.

And

then
,

foremost
,

like

these

spaces

that

we

work

out

of

are

mostly

empty
,

offices

have

been

fairly

underutilized

for

a

really

long

time
.

Offices

have

been

fairly

underutilized

for

a

really

long

time
.

So

my

background

in

design

and

thinking

about

new

ways

to

create

value

has

really

driven

me

into

this

world

of

the

future

of

work

and

how

we

make

work

work

for

us
.

Alex
7:24

Why

did

you

decide

to

become

a

leader

in

your

chosen
?

Sam Rosen
7:26

niche

For

me
.

I

think

it's

always

been

about

following

my

intuition

and

my

gut
.

This

path

has

been

very

organic

and

intuitive

and

I've

just

sort

of

learned

new

things

and

always

been

very

open

to

change
.

So

I

think

it's

following

what

I've

learned

and

how

to

apply

that

to

new

ideas

and

new

things
.

I

think

anytime

you

try

to

get

really

good

at

something
,

the

best

way

to

do

that

is

to

learn
,

it's

to

listen
,

it's

to

build

community

and

connection
.

So

for

me
,

I

don't

know

if

I

chose

this
.

I

don't

think

as

a

little

kid

I

thought
,

hey
,

I'm

going

to

become

an

expert

in

the

future

of

work

and

the

office
.

But

I

think

just

my

lived

experience

and

then

my

curiosity

has

really

driven

me

to

live

in

this

world

and

learn

about

this

world
.

And

it's

been

quite

fascinating

through

COVID

and

over

the

last

few

years

just

to

see

how

much

this

world

has

transformed
.

So

it's

kept

it

very

exciting

and

engaging
.

Flexibility, Productivity, and Remote Work

Alex
8:35

What

was

the

best

advice

anyone

ever

gave

you
,

and

did

you

follow

it
?

Sam Rosen
8:40

One

of

my

favorite

quotes

is

actually

a

baseball

quote
.

It's

a

Branch

Rickey

quote
,

who

was

a

baseball

coach
,

and

my

dad

taught

it

to

me

at

a

very

young

age
.

And

that

is

luck

is

the

residue

of

design
,

and

I've

always

really

heeded

this

advice
.

If

you

ask

anybody
,

was

it

luck

or

was

it

hard

work
?

It's

always

a

combination

of

both
.

And

if

you

just

say

it's

hard

work
,

I

think

for

99%

of

people

that's

ego
.

Luck

is

such

an

instrumental

part

of

opportunity

and

success
.

But

I

think

the

people

that

I

know

that

have

been

really

successful

have

kept

this

concept

in

common
,

which

is

they

work

their

butts

off
,

they

put

themselves

in

the

right

room

in

the

right

opportunities

in

the

right

situations

and

then

they

let

luck

do

its

thing
.

So

I

think

it's

trusting

that

if

you

put

in

the

work
,

you

get

yourself

into

the

right

rooms
.

If

you

put

in

the

work

and

build

the

right

relationships

and

connections

and

just

be

patient
,

the

luck

will

come
.

Alex
9:50

And

what

made

you

choose

remote

work

and

how

has

it

benefited

you
?

Sam Rosen
9:55

I

love

this

question
.

For

me
,

remote

work

was

really

intuitive
.

I

love

this

question
.

For

me
,

remote

work

was

really

intuitive
.

I'm

at

the

age

where
,

you

know
,

in

my

career
,

the

internet

has

always

been

like

a

big

piece

of

it
.

So

for

us
,

when

we're

starting

the

agency
,

the

ability

to

allow

our

employees

to

work

where

they

get

their

best

work

done

has

always

seemed

very

intuitive
.

The

ability

to

hire

people

from

all

over

the

world
,

all

over

different

backgrounds

and

disciplines
,

has

just

been

made

our

quality

of

life
,

really

an

experience

and

ability

to

execute
,

I

think
,

much

better

For

me
.

Sam Rosen
10:33

I

love

remote

work
,

I

love

people
,

I

love

being

in

the

same

room

with

people

and

I

do

that

as

much

as

I

can

but

having

the

flexibility

and

autonomy

to

work

where

it

makes

sense

for

that

day

or

for

that

hour

or

for

that

project
,

or

being

able

to

respond
.

I

got

two

little

kids
,

I

have

a

five

and

a

seven-year-old
.

So

being

able

to

adjust

my

day

and

my

life

to

be

able

to

support

them

and

be

present
,

adjust

my

day

and

my

life

to

be

able

to

support

them

and

be

present
,

and

that's

what

it's

all

about
.

I

think

life's

too

short

to

not

give

yourself
,

and

if

you're

able

to

the

flexibility

to

be

present

and

flexible
.

So

I

think

that

flexibility

has

really

been

a

huge

driver

for

me

personally

and
,

as

we

focus

on

Desk

paths
,

the

ability

to

help

others

and

make

it

easier

for

them

to

do

that

has

been

really

quite

a

joy
.

Alex
11:28

What

are

your

best

tips

for

organizing

your

day

and

staying

productive
?

Sam Rosen
11:34

Oh

man
,

this

is
.

I

mean
,

I'm

like

a

productivity

sort

of

junkie
.

So

I've

tried

all

the

to-do

lists
,

all

the

apps
,

lots

of

different

techniques
.

I

think

for

me
,

you

know
,

some

tactics

that

are

pretty

consistent

are

I

have

a

great
,

I

love

a

good

to-do

list
.

I

think

really

staying

organized
,

having

a

place

like

an

inbox

to

put

your

ideas

and

thoughts

and

kind

of

a

process

to

work

through

them

and

organize

them
,

is

really

cool
.

Sam Rosen
12:04

I

use

a

tool

called

Aki

Flow

today
,

a-k-i-f-l-o-w
,

which

is

really

cool

and

I've

tried

all

of

them
.

But

one

of

the

big

principles

in

there

is

time

blocking

and

I

think

time

blocking

is

really

a

powerful

tool
,

especially

as

you're

remote
.

A

powerful

tool
,

especially

as

you're

remote
,

which

is

setting

these

dedicated

blocks

to

put

the

work

in

and

keeping

distractions

out
.

So

really

setting

a

goal

for

an

amount

of

time
,

figuring

out

the

best

way

to

kind

of

eliminate

the

distractions

that

can

come

from

that

and

just

really

staying

at

top

of

that
.

That's

probably

like

my

favorite

tool

and

tactic

right

now

is

a

good

tool

like

this

hockey

flow
,

time

blocking

or

use

like

sound

to

kind

of

and

just

like

a

couple

things

that

I

do

on

my

desk

to

like

make

sure

I

know

that

I'm

in

a

work

mode

rather

than

play

mode

and

that

might

be

like

hiding

other

windows

or

lighting

an

incense

or

playing

music
.

That

sort

of

stimulates

focus
.

Alex
13:03

So

now

I

want

to

find

out

more

about

the

company

that

you're

part

of
.

So

can

you

please

begin

by

telling

me

more

about

the

company

that

you're

part

of

and

its

origin

story
?

Sam Rosen
13:13

When

we

were

building

a

co-working

space

and

being

a

company

that

builds

technology

and

design
,

we

started

to

really

riff

on

ideas

and

tools

to

help

people

run

these

co-working

spaces
,

and

that

was

called

desk

time

and

through

that

and

interviewing

and

meeting

hundreds

and

hundreds

and

hundreds

of

different

workspace

providers
,

we

realized
,

man
,

what

these

spaces

need

more

than

anything
.

Sam Rosen
13:37

It's

not

fancy

technology

to

run
,

billing

and

connect

community

as

much

as

it

is

a

tool

to

get

butts

in

seats
,

really

to

drive

people

into

these

workspaces
.

So

that

was

really

the

initial

concept

behind

DeskPass
.

It

was

modeled

after

ClassPass
,

which

did

the

same

thing

for

gyms
,

and

we

thought

that

was

such

an

interesting

model

and

I

think

for

us
,

listening

to

our

customers
,

listening

to

the

data
,

we've

really

evolved

that

model

over

time

to

really

support

companies

that

are

thinking

about

remote

work

and

hybrid

work

and

allowing

their

employees

to

work

more

flexibly
.

And

we've

just

sort

of

listened

and

evolved

the

business

and

the

product

to

support

the

changes

that

we're

seeing
.

And

I

think

from

when

we

started

almost

15

years

ago

thinking

about

coworking

or

I

did

so

much

has

changed

and

evolved

and

improved
.

So

it's

been

this

yeah
,

this

very

natural

path

from

design

shop

co-working

operator

to

building

co-working

software

to

helping

these

flexible

workspace

providers

connect

with

individuals

and

companies

that

are

looking

for

great

workspaces

that

are

more

convenient

to

them

in

their

life
.

Building a Flexible Workspace Marketplace

Alex
14:53

And

what's

unique

about

the

company
.

Sam Rosen
14:56

There's

a

bunch

of
,

I

think
,

really

unique

things

about

DeskPass
.

I

think

often

people

compare

us

to

other

single

operators

like

Quora

in

the

UK

or

Industrious
,

which

are

all

really

successful

co-working

brands
.

What's

cool

about

DeskPass

is

it's

a

marketplace

of

thousands

and

thousands

and

thousands

of

bookable

resources

all

over

the

world

and

they're

not

all

like

WeWork

or

Regis
.

There

are

lots

of

mom

and

pop

shops
,

there

are

lots

of

local

operators

combined

with

the

big

guys
,

so

you

have

one

place

where

you

can

see

lots

of

options

in

your

neighborhood
.

You

can

find

the

right

space

for

you

and

compare

it

and

book

it

and

do

all

the

billing

through

our

platform
.

So

we

don't

own

any

of

the

office

space

but

we

partner

with

all

the

best

operators

all

over

the

world
.

And

this

means

downtown

but

also

like

much

more

rural

communities
.

So

that's

really

unique

about

our

platform
.

I

think
.

Just

also
,

we

really

care

about

design
.

We

really

care

about

user

experience
.

We

really

care

about

the

brand
.

Sam Rosen
16:10

Like

I

said
,

my

origin

is

building

a

co-working

space
.

So
,

like

a

lot

of

our

team

members

are

operators
,

they've

run

co-working

spaces
,

they

are

remote

employees
.

We

practice

what

we

preach
.

And

then

I'd

say
,

lastly
,

our

model

is

really

cool
.

Our

model

is

completely

pay-as-you-go
.

Sam Rosen
16:31

It's

completely

utilization-driven
,

meaning

if

you're

a

company

and

you

want

to

offer

DustPast

to

your

employees
,

you

can

build

a

branded

to

your

company

solution
.

You

can

roll

it

out

to

your

employees
.

They

get

access

to

it
.

If

they

don't

use

it
,

you

don't

pay

for

it
.

If

they

use

it
,

you

pay

for

it
.

So

you

only

pay

for

what

you

use
.

There's

no

licensing

or

minimums

or

software

fees

and

you

can

set

restrictions

and

rules

to

allow

you

to

really

kind

of

control

budget

and

how

much

someone

gets

to

use

this
.

So

it's

a

really

cool

way

to

offer

this

unbelievably

large

network

of

different

types

of

workspaces
,

but

do

it

in

a

way

that's

really

flexible
,

really

inexpensive

and

can

adapt

to

your

company

and

your

needs

or

your

personal

needs
.

That

makes

us

a

lot

different

than

certainly

the

traditional

office
,

but

even

just

like

a

WeWork

membership
.

Alex
17:24

What's

your

philosophy

on

building

a

great

team
?

I'm

going

to

keep

this

one

pretty

short
.

Sam Rosen
17:29

To

me
,

it's

don't

be

a

dick
,

do

the

right

thing
.

To

me
,

it's

building

a

great

team
,

is

building

a

great

company
,

building

a

place

where

people

want

to

work
.

Trusting

your

employees
,

listening

to

them
,

talking

to

them

that's

what

really

matters
.

I

just

think

life

is

too

short

to

not

build

a

place

where

you

want

to

work
,

and

I

think

that's

what

we

really

focus

on

is

building

a

place

where

our

employees

can

thrive
,

where

they

feel

valued
,

where

we

are

mindful

that

we're

all

humans
,

we're

all

doing

our

best
,

we're

all

learning
.

Try

to

give

folks

the

tools
,

the

guidance

that

they

need
,

to

feel

supported
,

and

I

think

we've

been

really

good

at

that
.

Our

company

is

both

the

best

and

one

design

unbelievable

retention
,

like

if

you

take

care

of

your

people

and

they

know

you're

doing

the

best

you

can

for

them
.

I

think

it

gives

you

a

lot

of

leeway
,

a

lot

of

latitude

and

a

lot

of

flexibility

in

the

hard

stuff

that

comes

from

running

a

business

and

the

hard

decisions

you

have

to

make
.

Alex
18:36

Can

you

talk

me

through

the

steps

of

your

hiring

process
,

sure
?

Sam Rosen
18:41

So

I

think

for

us
,

first

we

try

to

hire

slowly
,

we

try

to

be

pretty

mindful
.

It's

fun

to

hire

someone
,

it's

never

fun

to

have

to

let

somebody

go
.

So

we

really

try

to

hire

slowly
,

we

try

to

be

pretty

mindful
.

It's

fun

to

hire

someone
,

it's

never

fun

to

have

to

let

somebody

go
.

So

we

really

try

to

hire

people
.

When

we

know

there's

aires

and

the

philippines

and

africa

all

over

the

united

states

and

canada
,

that

gives

us

a

lot

of

flexibility

and

ability

to

to

hire

this

much

broader

talent

pool
.

But

yeah
,

I

mean
,

you

do

your

job

description
,

you

get

the

word

out

there

and

then

we
,

once

we

find

candidates

that

really

seem

like

a

good

fit

from

a

qualitative

perspective
,

we

really

try

to

make

sure

that

they

get

to

meet

the

team
,

the

team

meets

them
,

that

it's

a

good

cultural

fit
.

We

often

do

a

contract

to

hire

so

that

we

can
,

if

it's

possible
,

so

that

people

can

kind

of

get

a

vibe

of

the

company

and

make

sure

it's

the

right

place

for

them

and

that

they're

the

right

people

for

us
.

Alex
19:53

How

would

you

describe

the

company's

success

so

far
?

Sam Rosen
19:57

Man
?

That's

a

hard

question

to

ask

an

entrepreneur
.

I

think
,

from

my

perspective
,

we're

always

trying

to

grow
,

we're

always

trying

to

thrive
,

we're

always

comparing

to

grow
,

we're

always

trying

to

thrive
.

We're

always

comparing

ourselves

against

others
.

We're

in

a

relatively

nascent

new

market

where

there's

not

a

lot

of

established

players

and

people

feels

like

you're

behind

and

there's

always

more

to

do
.

And

then

every

once

in

a

while

you

get

to

kind

of

step

back

and

have

some

perspective

or

have

a

conversation

or

some

sort

of

recognition

or

acknowledgement

to

realize

like

no
,

you've
,

we've

come

a

really

far
,

long

way
.

I

think

for

us

we're

one

of

the

sort

of

most

enduring

brands

DuskPass
,

you

know
,

flexible

work

and

co-working
,

I

mean
,

especially

here

in

the

States
.

I

think

we

drive

as

much

traffic

to

workspaces

as

any

other

marketplace

provider

in

the

world

and

we

get

to

work

with

some

of

the

coolest
,

most

innovative
,

interesting

companies

in

the

world
.

So

I

think

like

we've

had

a

lot

of

success
.

But

you

know
,

there's

always

so

much

more

to

do
.

Alex
21:15

And

what's

next

on

the

horizon
?

Sam Rosen
21:18

We

really

started

our

journey

with

external

capital
,

so

we

raised

angel

money
,

we

raised

some

venture

capital

and

that's

been

really

the

driver

that

has

allowed

us

to

grow

and

scale

the

business
.

For

us
,

we're

focused

on

a

couple

of

things

a
,

building

the

best

experience

in

the

world

to

find

flexible

workspaces
,

learn

about

them
,

book

them

and

experience

them
,

and

that's

we're

always

trying

to

iterate

our

product

and

our

tool

and

the

tools

that

we

offer

teams

to

really

manage

this

for

their

employees
.

And

we're

focused

on

continually

evolving

and

improving

the

platform

and

the

technology

and

the

brand

to

support

that
.

And

then

laser

focused

on

building

a

business

that

is

a

profitable
,

cash

flowing

business
,

which

we're

very

close

to

and

I

think

will

give

us

a

lot

of

flexibility

and

the

ability

to

endure

the

future

and

really

control

our

destiny

to

what

we

want

to

build
,

how

we

want

to

build

it
,

sort

of

what

the

right

pace

and

right

decisions

are

for

us
.

Alex
22:26

Is

there

a

particular

team

or

company

whose

culture

you

admire
?

Sam Rosen
22:32

Well
,

I'm

a

Chicago

boy

so

I

tend

to

think

about

companies

here

that

really

inspire

me
.

I

mean
,

I

think

the

one

that

always

comes

top

of

mind

is

Basecamp
,

the

project

management

software
,

the

37

Signals

that's

built

all

sorts

of

other

really

wonderful

tools

written

New

York

Times

bestsellers

on

remote

work

has

really

built

a

philosophy

around

remote

work
,

around

a

quiet
,

calm

company
,

about

a

profitable
,

cash-flowing

company
,

controlling

your

destiny
,

really

supporting

employees

in

a

work-life

balance

and

not

sort

of

mixing

business

with

family
.

There's

other

companies

in

Chicago
,

like

Field

Notes
,

which

is

such

a

cool

brand
,

or

Jim

Cuddle
,

who's

the

founder
,

is

a

really

inspiring

human

to

me
.

Yeah
,

I

like

Tiny
,

which

is

not

a

Chicago

company

but

that

has

built

so

many

cool

projects

that

kind

of

came

from

design

and

then

investing

and

building

and

supporting

other

companies
.

So

I

mean

those

are

companies

that

come

to

mind
.

Growing

up

I

was

such

an

Apple

Steve

Jobs

nerd

so

I

always

sort

of

look

to

them

and

see

what's

happening
.

So

yeah
,

I

think

those

are

a

few

acts

that

come

to

mind

on

the

fly
.

Alex
23:51

And
,

as

we

begin

to

wrap

up
,

what

excites

you

about

what's

ahead
?

Sam Rosen
23:58

One

of

the

things

that

I

think

is

so

cool

about

how

the

world

has

changed

post-COVID
,

around

how

people

work

and

where

people

work
,

is

the

world

has

become
.

Sam Rosen
24:08

Corporations

have

become

a

lot

more

adaptable

and

recognize

that

people

can

be

productive

and

effective

outside

of

the

office

and
,

at

the

end

of

the

day
,

what

that

means

more

freedom
,

more

autonomy

to

the

99.9%

of

people

who

are

not

the

boss
,

who

have

to

get

the

work

done
,

and

giving

them

the

tools

and

the

flexibility

to

really

build

a

life
,

a

lifestyle

that

is

much

more

cooperative

with

their

job

and

less

of

like

a

job

versus

life
,

and

allows

people

to

kind

of

build

the

right

chemistry

that

supports

them
.

So

I

think

one

of

the

coolest

things

about

this

drive

and

growth

in

remote

work

and

worker

flexibility

is

really

just

allowing

people

to

live
.

I

think

that

will

continue

to

happen
.

I

think

that

we're

just

still

at

the

beginning

of

this

and

there's

going

to

be

so

many

more

tools

and

technology

and

cultural

changes

that

are

really

going

to

support

this

and

we're

really

even

though

I've

been

doing

this

almost

15

years

we're

still

in

the

early

innings

and

I

think

it'll

be

really
,

really

wonderful

for
,

hopefully
,

the

humans

that

have

to

do

the

work
.

Alex
25:31

And

what

do

you

like

to

do

when

you're

not

working
?

Sam Rosen
25:34

I'm

a

dad

man
.

I

have

a

five-year-old
,

I

have

a

seven-year-old
.

I

love

being

their

dad
.

I

think

one

of

the

coolest

things

about

being

a

parent

is

a

reminder

to

be

present
.

And

I

just

have

this

wonderful

little

window

where

the

kids

are

young

and

we

all

love

each

other

a

lot

and

we're

their

world

and

I

just

like

I'm

trying

to

spend

a

lot

of

my

time

and

energy

appreciating

that

and

enjoying

it

while

it's

here
,

before

it

changes

Other

than

that
.

I

love

to

travel
,

I

love

to

eat
,

photography
,

I

love

taking

photos
.

Those

are

the

things

that
.

Really
.

That's

more

than

enough

with

a

full-time

job

running

Best

Pass
.