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December 8, 2024 26 mins

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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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Alex (00:00):
This is the Remote Work Life Podcast.
Yes, it certainly is, and I'myour host, alex Wilson-Campbell.
Thank you so much for joiningme.
Have you ever found yourselftrying to find somewhere to work
, somewhere that's comfortable,somewhere you feel you can be at
your most productive, andsomewhere that's got good Wi-Fi?
Well, today's guest, sam Rosen,is co-founder and CEO of a

(00:24):
business that has solved thatproblem on a global scale, and
the origin story of the businessis something to certainly
listen out for, as is therefreshing way in which his team
goes about the hiring process.
So listen up and enjoy today'sepisode.
Today's episode.

Sam Rosen (00:44):
So I am based out of Chicago and I am the co-founder
and CEO of DeskPass, which is amarketplace that helps connect
companies and the folks who workat those companies with
flexible workspaces all over theworld.
So that includes desks, meetingrooms and offices all available

(01:05):
by the hour, up to month tomonth to month.
I'm based out of Chicago andhave a nice little family.
I live in a little town calledOak Park.
I came into this industry as adesigner.
Before this, I started a designfirm called One Design Company

(01:26):
here in Chicago that does workall over the world for all sorts
of really interesting clients,and so my background has always
really been the intersection ofdesign and technology and
because of that, I came acrossco-working really really early
on, when there are about 300spaces in the world that call
themselves a co-working space,and my on, when there were about
300 spaces in the world thatcalled themselves a co-working

(01:47):
space, and my partner at theagency 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 plusworkspaces to just this change
in how we work and where we work, and I've always really taken
it from just a perspective ofhumans and design and human,

(02:10):
just how we work and how wethink about living our best life
.

Alex (02:18):
Next, can you describe a personal story or experience
that has influenced who you aretoday?

Sam Rosen (02:24):
a personal story or experience that has influenced
who you are today.
Well, to this question is how Icame across co-working and,
like I mentioned, I owned anagency or still do and I got to
travel a lot.
There's probably like less than10 of us and I was traveling to
New York a lot from Chicago andI was living out of when I was
there, out of my girlfriend'sapartment and she was super cool

(02:46):
.
She had a horrible.
She had a garden apartment witha thin layer of clothing always
on the ground and very badinternet and very bad cell phone
coverage and we actually hadthe biggest pitch that we had to
date and I was kicking off theengagement and I don't know.

(03:07):
I dropped the call like fiveplus times and my colleague at
the time was like dude, youcan't do this anymore, you need
to get your shit together.
So I did what any I think NewYork hipster would do is I found
a cool cafe that was down thestreet called the rabbit hole.
I always love the names inthese stories and I would work

(03:30):
out of the rabbit hole all day.
Honestly, didn't have muchbetter internet and much better
cell coverage and they clearlydidn't want me to work there
because I had a table tent thatwould say would say no working
during lunch rush.
Then the power stopped workingand they turned off the Wi-Fi.
So I was trying to find asolution and that same colleague

(03:51):
said, hey, have you ever heardof co-working?
And I said, well, I think mostpeople said at that time which
was co-what?
And there was like oneco-working wiki that had all the
co-working spaces in the worldabout 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 atthe time was the Change you Want
to See.
So I ended up with the Changeyou Want to See and showed up,

(04:15):
had no idea what I was gettingmyself into, and the guy said,
hey, are you here for co-working?
And I said yeah.
He said okay, great, and helpedme to get myself comfortable.

(04:35):
I had a few rules to berespectful, to not take over too
much internet and at the end ofthe day, if you liked the
experience, to drop a tip in thetip jar, girlfriend, and were
in design and media andentertainment and just really
absolutely fell in love withthis idea of collaborative
working and working with peopleother than your colleagues, but
together, and I looked to seewho is doing this in Chicago and

(04:55):
the answer was nobody.
But there were already peoplewho signed up saying I'd be
interested in this space.
So my partner and I decided togive it a shot and that's really
like the origin of how I foundco-working and that really, I
think has been quiteinstrumental in my path since
then.

Alex (05:14):
As you look back on your life and connect the dots that
led you where you are now.
What are those dots?

Sam Rosen (05:23):
Like when I think about answering this question it
always comes to me back to howI was raised and I have a really
fabulous family.
My mom's a painter, my daddirected television growing up
and was in production.
So I always kind of grew up inthis like mix of art and
production and media.
That has really guided a lot ofhow I've thought about and I've

(05:46):
always been very, veryentrepreneurial.
So since I was a little kidI've always had some type of
racket, whether it be likeself-publishing or doing website
design or just trying to findways 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 agencyhas really shaped a lot of how I

(06:09):
think about the world.
I've been able to learn a lotabout different industries,
always sort of thinking abouthow great design and great brand
intersects with reallyinteresting upcoming innovative
technology.
So that's really been sort ofthe bedrock of how I think about
things.
And then I just kind of rightplace, right time came across

(06:34):
workspace and this was a longtime ago, 15 years ago but it
was always pretty clear to me,using sort of this frame of
knowledge that how we work andwhere we work was backwards.
It wasn't oriented around thepeople who are the workers.
It was oriented around theirboss or the building owner or
the bank.

(06:54):
And then, foremost, like thesespaces that we work out of are
mostly empty, offices have beenfairly underutilized for a
really long time.
Offices have been fairlyunderutilized for a really long
time.
So my background in design andthinking about new ways to
create value has really drivenme into this world of the future

(07:15):
of work and how we make workwork for us.

Alex (07:24):
Why did you decide to become a leader in your chosen?

Sam Rosen (07:26):
niche For me.
I think it's always been aboutfollowing my intuition and my
gut.
This path has been very organicand intuitive and I've just
sort of learned new things andalways been very open to change.
So I think it's following whatI've learned and how to apply

(07:48):
that to new ideas and new things.
I think anytime you try to getreally 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 Ichose this.
I don't think as a little kid Ithought, hey, I'm going to

(08:09):
become an expert in the futureof work and the office.
But I think just my livedexperience and then my curiosity
has really driven me to live inthis world and learn about this
world.
And it's been quite fascinatingthrough COVID and over the last
few years just to see how muchthis world has transformed.

(08:31):
So it's kept it very excitingand engaging.

Alex (08:35):
What was the best advice anyone ever gave you, and did
you follow it?

Sam Rosen (08:40):
One of my favorite quotes is actually a baseball
quote.
It's a Branch Rickey quote, whowas a baseball coach, and my
dad taught it to me at a veryyoung age.
And that is luck is the residueof design, and I've always
really heeded this advice.
If you ask anybody, was it luckor was it hard work?

(09:02):
It's always a combination ofboth.
And if you just say it's hardwork, I think for 99% of people
that's ego.
Luck is such an instrumentalpart of opportunity and success.
But I think the people that Iknow that have been really
successful have kept thisconcept in common, which is they

(09:25):
work their butts off, they putthemselves in the right room in
the right opportunities in theright situations and then they
let luck do its thing.
So I think it's trusting thatif you put in the work, you get
yourself into the right rooms.
If you put in the work andbuild the right relationships
and connections and just bepatient, the luck will come.

Alex (09:50):
And what made you choose remote work and how has it
benefited you?

Sam Rosen (09:55):
I love this question.
For me, remote work was reallyintuitive.
I love this question.
For me, remote work was reallyintuitive.
I'm at the age where, you know,in my career, the internet has
always been like a big piece ofit.
So for us, when we're startingthe agency, the ability to allow
our employees to work wherethey get their best work done

(10:15):
has always seemed very intuitive.
The ability to hire people fromall over the world, all over
different backgrounds anddisciplines, has just been made
our quality of life, really anexperience and ability to
execute, I think, much betterFor me.
I love remote work, I lovepeople, I love being in the same

(10:36):
room with people and I do thatas much as I can but having the
flexibility and autonomy to workwhere it makes sense for that
day or for that hour or for thatproject, or being able to
respond.
I got two little kids, I have afive and a seven-year-old.
So being able to adjust my dayand my life to be able to

(10:57):
support them and be present,adjust my day and my life to be
able to support them and bepresent, and that's what it's
all about.
I think life's too short to notgive yourself, and if you're
able to the flexibility to bepresent and flexible.
So I think that flexibility hasreally been a huge driver for
me personally and, as we focuson Desk paths, the ability to

(11:21):
help others and make it easierfor 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 productivitysort of junkie.
So I've tried all the to-dolists, all the apps, lots of
different techniques.
I think for me, you know, sometactics that are pretty
consistent are I have a great, Ilove a good to-do list.
I think really stayingorganized, having a place like

(11:56):
an inbox to put your ideas andthoughts and kind of a process
to work through them andorganize them, is really cool.
I use a tool called Aki Flowtoday, a-k-i-f-l-o-w, which is
really cool and I've tried allof them.
But one of the big principlesin there is time blocking and I
think time blocking is really apowerful tool, especially as

(12:17):
you're remote.
A powerful tool, especially asyou're remote, which is setting
these dedicated blocks to putthe work in and keeping
distractions out.
So really setting a goal for anamount of time, figuring out
the best way to kind ofeliminate the distractions that
can come from that and justreally staying at top of that.
That's probably like myfavorite tool and tactic right

(12:39):
now is a good tool like thishockey flow, time blocking or
use like sound to kind of andjust like a couple things that I
do on my desk to like make sureI know that I'm in a work mode
rather than play mode and thatmight be like hiding other
windows or lighting an incenseor 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 bytelling me more about the
company that you're part of andits origin story?

Sam Rosen (13:13):
When we were building a co-working space and being a
company that builds technologyand design, we started to really
riff on ideas and tools to helppeople run these co-working
spaces, and that was called desktime and through that and
interviewing and meetinghundreds and hundreds and
hundreds of different workspaceproviders, we realized, man,

(13:34):
what these spaces need more thananything.
It's not fancy technology to run, billing and connect community
as much as it is a tool to getbutts in seats, really to drive
people into these workspaces.
So that was really the initialconcept behind DeskPass.
It was modeled after ClassPass,which did the same thing for

(13:58):
gyms, and we thought that wassuch an interesting model and I
think for us, listening to ourcustomers, listening to the data
, we've really evolved thatmodel over time to really
support companies that arethinking about remote work and
hybrid work and allowing theiremployees to work more flexibly.
And we've just sort of listenedand evolved the business and

(14:20):
the product to support thechanges that we're seeing.
And I think from when westarted almost 15 years ago
thinking about coworking or Idid so much has changed and
evolved and improved.
So it's been this yeah, thisvery natural path from design
shop co-working operator tobuilding co-working software to

(14:42):
helping these flexible workspaceproviders connect with
individuals and companies thatare looking for great workspaces
that are more convenient tothem in their life.

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 usto other single operators like
Quora in the UK or Industrious,which are all really successful
co-working brands.
What's cool about DeskPass isit's a marketplace of thousands

(15:19):
and thousands and thousands ofbookable resources all over the
world and they're not all likeWeWork or Regis.
There are lots of mom and popshops, there are lots of local
operators combined with the bigguys, so you have one place
where you can see lots ofoptions in your neighborhood.

(15:40):
You can find the right spacefor you and compare it and book
it and do all the billingthrough our platform.
So we don't own any of theoffice space but we partner with
all the best operators all overthe world.
And this means downtown butalso like much more rural
communities.
So that's really unique aboutour platform.

(16:01):
I think.
Just also, we really care aboutdesign.
We really care about userexperience.
We really care about the brand.
Like I said, my origin isbuilding a co-working space.
So, like a lot of our teammembers are operators, they've
run co-working spaces, they areremote employees.

(16:21):
We practice what we preach.
And then I'd say, lastly, ourmodel is really cool.
Our model is completelypay-as-you-go.
It's completelyutilization-driven, meaning if
you're a company and you want tooffer DustPast to your
employees, you can build abranded to your company solution
.
You can roll it out to youremployees.

(16:43):
They get access to it.
If they don't use it, you don'tpay for it.
If they use it, you pay for it.
So you only pay for what youuse.
There's no licensing orminimums or software fees and
you can set restrictions andrules to allow you to really
kind of control budget and howmuch someone gets to use this.
So it's a really cool way tooffer this unbelievably large

(17:06):
network of different types ofworkspaces, but do it in a way
that's really flexible, reallyinexpensive and can adapt to
your company and your needs oryour personal needs.
That makes us a lot differentthan certainly the traditional
office, but even just like aWeWork membership.

Alex (17:24):
What's your philosophy on building a great team?
I'm going to keep this onepretty short.

Sam Rosen (17:29):
To me, it's don't be a dick, do the right thing.
To me, it's building a greatteam, is building a great
company, building a place wherepeople want to work.
Trusting your employees,listening to them, talking to
them that's what really matters.
I just think life is too shortto not build a place where you

(17:52):
want to work, and I think that'swhat we really focus on is
building a place where ouremployees can thrive, where they
feel valued, where we aremindful that we're all humans,
we're all doing our best, we'reall learning.
Try to give folks the tools,the guidance that they need, to

(18:12):
feel supported, and I thinkwe've been really good at that.
Our company is both the bestand one design unbelievable
retention, like if you take careof your people and they know
you're doing the best you canfor them.
I think it gives you a lot ofleeway, a lot of latitude and a
lot of flexibility in the hardstuff that comes from running a

(18:33):
business and the hard decisionsyou 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'snever 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'snever fun to have to let
somebody go.
So we really try to hire people.
When we know there's aires andthe philippines and africa all

(19:11):
over the united states andcanada, that gives us a lot of
flexibility and ability to tohire this much broader talent
pool.
But yeah, I mean, you do yourjob description, you get the
word out there and then we, oncewe find candidates that really
seem like a good fit from aqualitative perspective, we

(19:31):
really try to make sure thatthey get to meet the team, the
team meets them, that it's agood cultural fit.
We often do a contract to hireso that we can, if it's possible
, so that people can kind of geta vibe of the company and make
sure it's the right place forthem 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 askan 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 comparingourselves against others.
We're in a relatively nascentnew market where there's not a
lot of established players andpeople feels like you're behind

(20:25):
and there's always more to do.
And then every once in a whileyou get to kind of step back and
have some perspective or have aconversation or some sort of
recognition or acknowledgementto realize like no, you've,
we've come a really far, longway.
I think for us we're one of thesort of most enduring brands

(20:47):
DuskPass, you know, flexiblework and co-working, I mean,
especially here in the States.
I think we drive as muchtraffic to workspaces as any
other marketplace provider inthe world and we get to work
with some of the coolest, mostinnovative, interesting
companies in the world.
So I think like we've had a lotof success.

(21:08):
But you know, there's always somuch 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, weraised some venture capital and
that's been really the driverthat has allowed us to grow and
scale the business.
For us, we're focused on acouple of things a, building the
best experience in the world tofind flexible workspaces, learn

(21:41):
about them, book them andexperience them, and that's
we're always trying to iterateour product and our tool and the
tools that we offer teams toreally manage this for their
employees.
And we're focused oncontinually evolving and
improving the platform and thetechnology and the brand to
support that.

(22:01):
And then laser focused onbuilding a business that is a
profitable, cash flowingbusiness, which we're very close
to and I think will give us alot of flexibility and the
ability to endure the future andreally control our destiny to
what we want to build, how wewant to build it, sort of what
the right pace and rightdecisions 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 reallyinspire me.
I mean, I think the one thatalways comes top of mind is
Basecamp, the project managementsoftware, the 37 Signals that's
built all sorts of other reallywonderful tools written New
York Times bestsellers on remotework has really built a

(22:55):
philosophy around remote work,around a quiet, calm company,
about a profitable, cash-flowingcompany, controlling your
destiny, really supportingemployees in a work-life balance
and not sort of mixing businesswith family.
There's other companies inChicago, like Field Notes, which
is such a cool brand, or JimCuddle, who's the founder, is a

(23:19):
really inspiring human to me.
Yeah, I like Tiny, which is nota Chicago company but that has
built so many cool projects thatkind of came from design and
then investing and building andsupporting other companies.
So I mean those are companiesthat come to mind.
Growing up I was such an AppleSteve Jobs nerd so I always sort

(23:42):
of look to them and see what'shappening.
So yeah, I think those are afew 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 changedpost-COVID, around how people
work and where people work, isthe world has become.
Corporations have become a lotmore adaptable and recognize
that people can be productiveand effective outside of the

(24:24):
office and, at the end of theday, what that means more
freedom, more autonomy to the99.9% of people who are not the
boss, who have to get the workdone, and giving them the tools
and the flexibility to reallybuild a life, a lifestyle that
is much more cooperative withtheir job and less of like a job

(24:48):
versus life, and allows peopleto kind of build the right
chemistry that supports them.
So I think one of the coolestthings about this drive and
growth in remote work and workerflexibility is really just
allowing people to live.
I think that will continue tohappen.
I think that we're just stillat the beginning of this and

(25:11):
there's going to be so many moretools and technology and
cultural changes that are reallygoing to support this and we're
really even though I've beendoing this almost 15 years we're
still in the early innings andI think it'll be really, really
wonderful for, hopefully, thehumans 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 havea seven-year-old.
I love being their dad.
I think one of the coolestthings about being a parent is a
reminder to be present.
And I just have this wonderfullittle window where the kids are
young and we all love eachother a lot and we're their

(25:58):
world and I just like I'm tryingto spend a lot of my time and
energy appreciating that andenjoying it while it's here,
before it changes Other thanthat.
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 afull-time job running Best Pass.
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