July 1, 2025 • 41 mins
This episode, we're diving into the story of Sam Rosen, founder of Deskpass— a marketplace that connects companies with co-working spaces all over the world.
Seven years ago, before coworking became a buzzword, Sam recognized the need to connect people with cool spaces to work in. Fueled by vision, grit, and an unshakable belief in learning through failure, Sam turned obstacles into stepping stones. His secret? He’s not afraid to fail—because every failure is a chance to grow.
Sam’s journey is a masterclass in persistence, empathy, and vulnerability. He doesn’t just lead with vision—he leads with heart.
Tune in to hear how Sam continues to learn, adapt, and rise—every single day.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
UNKNOWN (00:00):
Thank you.
SPEAKER_01 (00:03):
Thank you so much.
(00:34):
Hi, Sam.
Thank you for joining us today.
Hi,
SPEAKER_02 (00:36):
Sam.
I'm so excited you're here,mostly because you're a
brilliant human, but alsobecause the people that we have
in common are way too fun for usnot to have you here.
I know it's going to be a greatconversation today.
Thanks for coming.
SPEAKER_00 (00:52):
Yeah, thank you guys so much.
It's nice to meet you, and I'mexcited to chat as well.
SPEAKER_01 (00:58):
All right, Sam.
So let's start off.
Tell us about DeskPass, what youdo, and what inspired you to
start the business.
SPEAKER_00 (01:08):
Absolutely.
So DeskPass is a marketplacethat connects companies and most
importantly, the people who workat those companies with all
sorts of incredible workspacesall over the world.
So co-working spaces that areavailable to book by the day or
the hour.
So we sell basically meetingrooms by the hour, desk by the
(01:29):
day, private offices, all reallyshort term and pay as you go.
And what inspired this idea wasI came across coworking about 17
years ago, which like hurts myhead when I say that out loud
and I have to always doublecheck.
But I came across this conceptof coworking in New York City
(01:54):
And I had never heard of itbefore.
And no one had heard of itbefore.
There were about 300 of theseworkspaces in the world.
If you wanted to find them, youhad to go to the coworking wiki.
And there weren't any inChicago.
So myself and my partner, Pat,we have a design and branding
(02:19):
firm.
And we're like, we have someextra office.
There are no co-working spaceshere in Chicago.
Let's open one up.
And from that, I just sort offell in love with this notion of
where and how we work and theidea that the office didn't have
to be what I think most peoplethink of it as still today.
SPEAKER_02 (02:43):
That is so cool.
And I just think to myself,like, It's hard for me to even
remember a time where we didn'tknow what coworking was because
it's so part of how we do lifenow.
But you're right.
There was literally a time notthat long ago where it was not
so mainstream.
(03:03):
You had never even heard of thisconcept before.
SPEAKER_00 (03:07):
Yeah, there were no movies or TV shows about WeWork.
SPEAKER_02 (03:12):
Right?
Not at that point.
So that had to have been alittle bit mind-blowing.
When you saw it, was itinstantly you were like, that
makes so much sense?
SPEAKER_00 (03:21):
Yeah, it was a really obvious idea that I had
never considered before.
For me, I was traveling to NewYork a lot, and I was staying
with my girlfriend and workingout of her really...
crappy apartment and it was anice apartment and she was
wonderful but it was just messyand I had bad cell phone and bad
(03:45):
internet and I would Didn't knowwhat to do.
So I started working at the cafedown the street called the
rabbit hole.
And I realized they didn't wantme there because I'd sit there
all day.
I'd have two coffees and a bageland I would take their expensive
Brooklyn real estate away frombetter paying customers.
And the name of the coworkingspace was called the change you
(04:06):
want to see, which I thought wasthe dumbest name when I heard
it.
But in hindsight, It's thegreatest name because it really
did.
I walked into a room of a bunchof really fascinating people and
arts and media and design andtechnology that were just
sharing space together.
(04:27):
And I was like, oh, duh.
But you ask anybody at thattime, there was, do you know
what?
coworking is.
Everyone would say the samething.
They'd say, co-what?
And you'd be surprised at howmany people still don't know
what coworking is.
But we've come a long way.
SPEAKER_02 (04:46):
Yeah, I guess in Chicago, we finally caught up,
right?
But outside of Chicago, maybethere are still some cities that
haven't had exposure just yet.
I guess we forget about that,don't we?
SPEAKER_00 (04:59):
Yeah, we live in a big city with a like a pretty
progressive scene.
But I still like, when I'm in anUber or a cab, people say, you
know, what do you do?
And you'd be surprised when Isay co-working, how many people
are like, what?
What's that?
But it's every day, more andmore people.
I
SPEAKER_02 (05:18):
love that.
It's brilliant.
I mean, we have an office thatis a co-working location.
And so I guess, and we've beenthere for quite a while now.
And so to me, it's just likepart of life.
I can't even...
Like I said, as you were sayingit, I was like, oh my gosh, you
are right.
Like there was literally a timewhere this wasn't a thing.
(05:39):
I can't remember it, but wow.
So yeah, thank you for sharingthat.
That was a fun, just kind oflittle rewind back to a totally
different time.
A
SPEAKER_00 (05:51):
very different time.
SPEAKER_01 (05:54):
So Sam, how did your career begin?
Was owning your own businessalways kind of a goal that you
wanted to pursue?
Or did it happen more byaccident?
SPEAKER_00 (06:07):
I'm a unique, I think, nice little Jewish kid
from the North Shore of Chicagoin the sense that my mom is a
painter, my dad...
directed and produced televisiongrowing up.
So unlike my, I think my peerswhere it's like, you can be
(06:28):
whatever you wanna be when yougrow up, but we'd prefer if
you're not a doctor or a lawyer.
So I've always had sort of thisautonomy and support to like
kind of explore and do what Iwant, which is lucky and plenty
privileged.
I've always been entrepreneurialsince I was a little kid.
(06:48):
You name it, right?
When CDRs came out trying tosell mixtapes to kids in junior
high or writing poetry books orbuilding websites.
That was always very intuitiveand natural to me, and I never
(07:08):
really considered...
anything else until recently.
But I, you know, I think whenyou're young and you, you're
kind of ignorant to the risksassociated with starting your
own thing and building your ownthing.
And it's kind of a blessing inthe sense that I married, I got
(07:34):
two kids, I got a mortgage,right?
The idea now of starting a newbusiness and the risk associated
to it would make me think aboutit differently.
But I just didn't, it's just howmy brain's wired and I didn't
know any better.
So yeah, I've always beenentrepreneurial.
My first like substantivebusiness, which turned 20 years
old this year, which is wild,right?
(07:58):
is called One Design Company,which is a digital branding
agency that does reallywonderful design and brand and
like interactive work.
And that has been the most kindof consistent foundation of me
of just thinking about designand how it meets technology.
And then as I've learned aboutnew ideas and concepts like
(08:21):
coworking, it's given me a bitof a platform to like, riff and
explore and try new things.
So yeah, for better, for worse,I think this is the way for me.
SPEAKER_01 (08:34):
So you're not a single entrepreneur.
You're actually like a doubleentrepreneur.
SPEAKER_00 (08:38):
I'm more than that.
But yeah, I'm the real deal, Ithink, just in terms of I don't
know any better anymore.
Yeah.
SPEAKER_02 (08:51):
Isn't it so great though?
I love that you included thewhole bit about like when you're
young enough and you don't evenrealize the risks associated
with it.
SPEAKER_00 (08:59):
Yep.
SPEAKER_02 (09:00):
Because then when you do it once, you got to do it
again and then you got to do itagain.
It is one of those things Ithink that just becomes so easy
to, it's like your newobsession, you know?
Because every single time is sodifferent, but there are enough
(09:22):
similarities that you kind offeel a little bit more bold and
then you just kind of go inbigger.
Has that been your experience?
Like, have you been superexcited?
Like once you do one thing to goto the next thing, like how does
that look for you?
Or do you do it all at the sametime?
Are you like...
Boom, boom, boom,
SPEAKER_00 (09:38):
boom, boom.
I love the beginning, right?
Like I love the zero to like upand running phase.
I love the idea of like, I havean idea and trying to make that
idea like a real thing.
I think a lot of people arescared of that because they have
an idea.
And then this idea, you know,this, how do I get from here to
(10:00):
there?
And they're like looking up andthey're like, man, I don't, it's
such a big step.
And in reality, it's a bunch oflittle steps.
You know what I mean?
And I think I learned thatearly, and that's helped me be
able to, like, when I have anidea, deconstruct it into, like,
all right, like, one bite at atime.
I have a lot of friends now inmy life that, like, have taken
(10:25):
more of a traditional sort of...
path of taking a job and workingfor a business.
And then they have an idea andthey're inspired.
And because they know me asthey're like, you know, this is
kind of my persona.
They're like, should I do it?
Should I do it?
And I often feel like I'm theguy.
They come to me with their,they're like at the ledge of a,
(10:48):
you know, at the ledge.
And they're like, should I jump?
Should I jump?
And I'm like, dude, I'm like,push them.
I'm like, go.
Like the worst thing happens isyou fail.
And then you learn a lot ofstuff and you're probably going
to, that'll help you go back towhat you were doing before and
give you more perspective.
So, but again, ignorance isbliss.
(11:09):
And I think I learned this at anearly age and I was very lucky
enough to be in a situationwhere I could afford to screw
up, you know?
SPEAKER_02 (11:18):
Well, I have to ask you.
So, let's say somebody'slistening to this and they're on
that ledge.
What do you usually recommend?
If there was one first littlesmall step, because I love that.
I love that you said, it seemslike this big, huge step, but
it's really a bunch of littleones.
Without having any clue of who'slistening to this and what it is
(11:40):
that they're considering jumpinginto, what's the first thing
that you would say to rip thatband-aid off, get real bold?
What is that first little step?
SPEAKER_00 (11:49):
Obviously, technology has changed so much
as it relates to this andimproved.
So I'd probably think about it alittle bit differently today
because there's such good toolsthat exist to help you break
things apart.
But again, I think it's likebreaking things apart into
smaller chunks.
It's, okay, you want to start abusiness.
(12:11):
Like, what's the...
what's the first thing you haveto do to start a business?
And what are the differentpieces?
People get tied up aboutincorporating a business and
insurance and really stuff thatis not scary.
It's not complicated.
Today, I know there's this wildAI bandwagon that's happening,
(12:33):
but the tools have never beenbetter to be able to put
together a concept and get helpand say, hey, this is my idea.
How should I get started?
And be spoon-fed like, okay,like step one, step two, step
three.
But I always think like havingthe right people around you to
(12:55):
support you, finding a mentor,finding someone who's done this
before who can just help you,advise you, you know, just kind
of soothe you when you'rescared, but be able to kind of
point you in the rightdirection.
I've leveraged that my wholecareer.
I'm so lucky.
And I think most people havesomeone in their life that can
say, here, here's where to look.
SPEAKER_02 (13:17):
Yeah.
We've heard a lot of people whenyou're talking with the founders
or the entrepreneurial mindedpeople, community is huge, which
obviously it's, goes back to theco-working concept too.
When you're working on your ownlike that, it's so important to
have a community around you.
(13:37):
So I'm really glad that you saidthat.
I think too, knowing how toproperly use AI or the
technology for what it's therefor and knowing when to sub the
person in is equally important.
UNKNOWN (13:53):
Yeah.
SPEAKER_00 (13:54):
It's never been easier.
It's never been easier to, inone button, you can set up and
incorporate a business inDelaware and have a bank account
and an incorporation andoperating docs.
That's insane.
In another button, you can havea business plan written by a
robot.
We live in amazing times.
SPEAKER_02 (14:16):
I mean, it's pretty insane.
ChatGPT created a picture ofwhat what it thought my dogs
would look like if they werehuman beings.
It can give you a step-by-stepon maybe where to start.
There are some really coolthings happening.
I want to see those
SPEAKER_00 (14:35):
pictures.
SPEAKER_01 (14:37):
You know what?
Dogs were very handsome, I mightsay, as humans.
They
SPEAKER_02 (14:42):
really were.
They really were.
And there's something weirdabout seeing a picture of your
animals as humans where you'relike, of course, that's you.
Absolutely.
I love
SPEAKER_00 (14:53):
novel use cases, and that's pretty high on the list.
I'm going to go home and seewhat my cats look like.
SPEAKER_02 (15:00):
You should.
You should, but I have to warnyou, sometimes they don't turn
out great.
So it's all about a good prompt.
So as with all things with AI,make sure your prompt is pretty
solid or you're in trouble.
No, but I think that's such animportant point, though, that
you're making is that barrier toentry and the level of access
people have to resources.
(15:22):
What an amazing time to bealive.
If you are entrepreneurial innature, or even if you're not,
but you've got a really greatidea, It is all right at your
fingertips.
So easy.
SPEAKER_00 (15:32):
Yeah.
SPEAKER_02 (15:32):
So easy.
SPEAKER_00 (15:33):
The other thing I would say is people are often
scared about sharing their ideabecause someone's going to steal
it.
SPEAKER_02 (15:42):
Oh, someone's going to steal it.
Oh, yeah.
SPEAKER_00 (15:45):
I've always thought that is not the right way of
looking at things.
If it's a great idea.
Someone's doing it.
So like, and no one's going toknow about it unless you share
it.
So I think that's the otherpiece where people are like, I
can't tell you until it's readyor fully baked or I need to sign
a non-disclosure.
(16:05):
And it's like, look, like ifthis is a good, I'm not going to
do your idea.
And if this is a good idea, likeit's probably being done or
you're really early and you gottime.
SPEAKER_02 (16:17):
Well, I'm glad you bring that up because I think
there are definitely times wherepeople get into that headspace.
And to me, that's scarcitymindset.
And I think it's an importantreminder for all of us, like,
because there will come a timewhere you're feeling like that
little bit of threat, but it'slike, oh no, you're going to
need so many people behind youknowing about what you're doing
(16:37):
and cheering you on and wantingto do what you're doing.
And like all of those things,that's going to be important for
your success, not the other wayaround.
SPEAKER_01 (16:44):
All right, Sam, I want, to ask you about some of
the obstacles or maybe let'seven call them failures that you
faced early on and tell us howyou overcame them and how they
even led to growth.
SPEAKER_00 (17:00):
Yeah, I feel like building a business is like,
building a fire from scratch,you know what I mean?
And sometimes it goes out andyou have to start over and
sometimes, you know, like youcan control it and sometimes it
controls you.
I think for me, one of my giftsis kind of seeing where things
(17:23):
are going.
So for me, with coworking, andsort of the future of work, a
lot of it became a lot moreobvious when COVID happened, but
we were so early.
To me, it was like a duh, likethis makes perfect sense.
I'm in River North in Chicago.
(17:44):
I'm looking across the street atthis building.
This building has been here for,I mean, I've been here for 12
years.
This building's been hereforever.
it was always mostly emptyduring most of the time.
These buildings have beenunderutilized for a long, long,
long time.
And I think the world isstarting to notice that more and
(18:05):
more.
For me, timing.
We were so early where themarket didn't exist.
When we started, we were sellingsoftware to manage these spaces.
And there weren't that many ofthem.
Everyone was so different thatthey were very complicated.
Like, it was hard to build aone-size-fits-all solution.
(18:26):
It was very complicated tobuild.
And they didn't have money.
They were really frugal.
It was like the trifecta of abad market.
So part of it is just stickingwith it, right?
Learning.
Iterating.
Most importantly, talking topeople, your customers,
listening to them.
(18:47):
Like...
It's a conversation, it's adialogue.
And for me, we had so manysetbacks because it was just too
early and it didn't exist yet.
So part of it is persistence.
Like if you ask, I think, youknow, one of my favorite Chicago
entrepreneurs, Mark Lawrence,who started Spot Hero, and he
(19:08):
said this once and I reallyappreciated this.
And he said, like, the numberone trait that I see for great
entrepreneurs is persistence.
is great like it's hard andyou're gonna fall on your face
and you're gonna want to cry andyou're gonna want to quit and
you're gonna want to take a joband you're gonna like doubt
(19:29):
yourself and you're gonna seeother people do what you're
thinking and have more successand you're gonna be like i suck
um waking up trying again overtime and not giving up.
And that's not to say youshouldn't ever give up, but I
think like more than intellect,more than intelligence, more
(19:52):
than access to capital,persistence of trying to solve
the problem, talking to thepeople you're trying to help,
listening to them, incorporatingthat feedback and evolving that
is I think what drivessuccessful people.
(20:14):
The other thing I would say is,which is what I think makes up
really good entrepreneurs andjust successful people in life.
It's not just related tobusiness.
It's that bad things are goingto happen, right?
And the people that I know thatare the most successful and the
(20:36):
happiest, and those are notmutually exclusive.
When those bad things happen,they extract the good out of it.
Even if they buy something for Xand sell it for X minus 50%.
Like they don't say, oh, thissucked.
(20:57):
I lost all my money.
They say, I learned a lot.
I had great, I made my, learnedmy best friend.
I learned what not to do.
I, And I think that thatmentality of like, there's
medicine everywhere, there'slike lessons everywhere.
And the people who not just arethe best at business, but I
(21:19):
don't know, often the happiestof life are the people who say,
there's a lot of good stuff hereand I'm going to take that and
I'm going to move.
That's what's going to propel meforward, not the negative side.
SPEAKER_02 (21:33):
Such an important reminder.
I feel like we oftentimes forgetthat we only see what we're
looking for.
And so if we're putting itthrough, if we're living this
life and having theseexperiences through a negative
lens or through a failure lensversus can I see the
opportunities and the lessonsand everything else?
I mean, two completely differentoutcomes that could have been in
(21:59):
a completely differentsituation.
Everything else was the same.
It's just how you choose to lookat it.
And then that determines, it hassuch a ripple effect and
determines so much movingforward.
I love that.
That is such a criticalreminder.
Brilliant.
Thank you.
SPEAKER_00 (22:17):
It's also what you see, right?
I mean, you see people likefriends and Instagram or
whatever, where you just see thehighlights, right?
You see entrepreneurs where theyjust post the wins and you can
be really successful at puttingforth an image, which is, I
(22:39):
don't know if it's disingenuous,but it's like, it is not the
whole picture.
And I can't believe how manytimes in my career I've thought,
I've misperceived where peopleactually were And sort of
overinflated their success ortheir traction or whatever.
When like later when things are,you know, when you could talk
(23:02):
about it and you have aconversation and it's like, no,
like more than most are goingthrough the same pain and trials
and tribulate, like the samestuff you are.
there, you know, you just can'tsee it.
So like there, there are veryfew stories I think of people
(23:23):
just like who get to avoid that.
SPEAKER_02 (23:26):
Yeah.
Yeah.
I, I, I would be interested inhearing if there was someone,
but what a crappy story.
I mean, like, like what would weeven be watching?
You know, it's like, there'snothing interesting that happens
and, if all we're watching isone win after the next and oh,
it's so easy, it'd be over infive minutes and we'd be like,
(23:49):
can't get that five minutesback.
I learned literally nothing.
There's nothing interestinghere.
But I wonder if it exists.
SPEAKER_00 (23:56):
Well, it's funny you say that.
So like when, you know, one ofour early competitors was
WeWork, right?
And WeWork, it was like,Competing against WeWork as a
co-working space operator in theearly days was, like, this
notion of, like, these guysdon't...
(24:19):
Like, gravity doesn't apply tothem.
Like, when I jump, I go thishigh.
But when they jump...
Like, money just flies out ofthe...
And it was just, like...
it seemed like they could do nowrong that they were just
defying the fastest.
And they were like, we're doingthe same thing, you know?
And then when the money machinestopped, you're like, Oh,
(24:42):
actually
SPEAKER_02 (24:42):
there's the story.
SPEAKER_00 (24:44):
There's a movie about
SPEAKER_02 (24:48):
that one.
That one is maybe not what itseems.
Yeah.
Yeah.
I mean, the whole thing isfascinating.
And I think, um, It's reallyfunny, you know, once you can
see behind that curtain, whatyou see sometimes is not what's
actually going on.
And if we just like measureourselves compared to what we
(25:09):
think we know.
Totally.
Like not only is it just stripthe joy right out of it, but
also these are not apples toapples situations like that is
just not a good form ofmeasurement at all.
But it's so hard not to do that.
SPEAKER_00 (25:23):
Yeah, it's human
SPEAKER_02 (25:25):
nature.
Why do we do that to ourselves?
SPEAKER_00 (25:27):
There's, there's, there's gotta be a reason.
SPEAKER_02 (25:29):
Could you figure that out and then we'll have you
come back and then we'll talk
SPEAKER_00 (25:33):
all about.
Okay.
I'll tell you in about fourminutes.
SPEAKER_01 (25:39):
Okay.
So Sam, this is probably, youshould probably take it further
back.
Cause I, you had already been anentrepreneur when you started
desk cast, but is there onething that you now know in this
industry, time in yourentrepreneurial journey that you
wish you knew when you started?
SPEAKER_00 (25:58):
You know, everyone's just making it up.
Like no one, no one's done thisbefore.
Nobody, many people have likerun a couple of businesses back,
but like they didn't liveanother life that they can
consciously, like we're all justwinging it.
You know, we sold desk pass lastyear and I started working for a
(26:19):
unbelievable, like it's thiscompany called Yardi.
It's the biggest propertytechnology company in the world
and it's run by someone who'sabout twice my age who started
this business 40 years ago onhis MS-DOS machine and like has
built a 10,000 personmulti-billion dollar empire and
(26:40):
you know going into that machineas an entrepreneur you're like
oh you think he has it all he'slike you know this is his dream
and his, he made it, how he madeit all up.
But again, I think you look, youuse these like Titans and you're
like, they're all winging it,man.
And I think when you realizethat it makes it like a little
(27:04):
less holy, like a little lesssacred.
And you realize like, we're, wegot one, we got one shot at
this.
So like, let's just have, do ourbest to have fun.
And it's fun to see how otherpeople make, make it all up.
Yes.
It's a thing.
SPEAKER_02 (27:22):
It's a real thing.
And it's so refreshing to, tohave people who are like, I
mean, I don't know.
We've never, we've literallynone of us have done life
before.
So like every time that we gothrough and do this, I mean,
like we're, we're waiting in it.
(27:42):
That is refreshing.
You meet so many people thatmake you feel like there's one
right way of doing all thethings, and if you're not doing
it that way, you're just notdoing it right.
But it's like, in what world?
SPEAKER_00 (27:55):
Yeah, in what world?
It's like, wait, you haven'tlived before?
You know what I mean?
You might be 40 years ahead ofme, but this is still your first
go-round, you know?
UNKNOWN (28:09):
Yeah.
SPEAKER_02 (28:10):
How quickly things change now.
I read something.
I'm not even going to try toquote it because I would just
sound like a moron.
The speed that things turn overand change and move and shake.
None of us have done thisbefore.
Literally none of us.
Even that person with 40 yearson, any of us, that literally
means nothing anymore becausewhat happened yesterday is now
(28:33):
so far out of date by 12 yearsin some old way of measuring
time.
It's like it moves so rapidly.
Literally none of us have donethis before.
Get some confidence.
Like everybody's sitting aroundthe table from you.
We should all just feel asconfident as the next person
because nobody knows.
SPEAKER_00 (28:53):
Yeah.
SPEAKER_01 (28:54):
But therein lies the hardest part is, is, trying to
feel confident you know i meanthere's a lot of people who
think i can't start a businessuntil i know this this this this
this this this and this and theybecome paralyzed in you know
their fear they become stuck inthat in not moving forward and i
do feel like in everyconversation we have with
(29:19):
entrepreneurs the differencebetween them and me who is not
who would forever get stuck inmy fear is just that.
You guys are willing to take theleap, even if you don't have all
the answers, and I'm stucktrying to find all the answers.
SPEAKER_00 (29:37):
But also, like, I don't know.
You fail enough, you know, acouple times, and it's less
scary, right?
the people who are like, Hey, Ilearned a lot.
I learned not what to do.
And then it becomes less scary.
It's like, okay, like, you know,your, your family will still
love you.
And if you're a good humanbeing, your people will still be
(30:00):
there for you.
They care way less than youthink.
Like it's so often you tie youridentity to what you do, but
like, that's not what otherpeople do.
They like tie you to you.
And, and, and that's whatmatters.
You know, I love this, um, therewas a art collaborative in
Austin and they made this posterand I have it when I go
(30:21):
downstairs, which is like wheremy stuff is and at my house.
And it says, tie your shoes,pack a good lunch and remember
that we're all in this together.
And I just like, that's it, man.
Like we're just, we're all doingthe best we can.
SPEAKER_02 (30:38):
Are you even a respected entrepreneur if you
haven't failed at least once?
SPEAKER_00 (30:44):
There's so much.
So much medicine in that.
And if you haven't done it yet,then time's ticking.
Unless it's maybe a WarrenBuffett.
I think he might make it.
SPEAKER_01 (30:59):
Sam, so in this kind of rapidly changing AI, moving
forward, changing just kind ofthe whole landscape of things,
how do you prepare for thefuture of your business?
SPEAKER_00 (31:13):
I love to learn.
Like...
I love learning.
I love reading.
I love podcasts.
When I do my errands and mychores, just listening,
especially as it relates toentrepreneurship, how other
people do stuff.
I just learned some amazingstuff this last weekend about
(31:36):
workflows for the future ofwork, but it's not just work
stuff.
I just like learning about howthe world works and how other
people do things and how thingslike, you know, like the science
or just sort of the mysterybehind different people in
different stories.
And I just like, to me, thatreally helps like to, to your
(32:01):
point, like it, things move sofast that you have to keep
listening and kind of tap in.
So for me, podcasts and booksand surrounding myself with
people that really inspire meand are doing things way
different to me.
This is like one of the reasonscoworking is so rad.
And one of the reasons that Ifell in love with it early on
(32:23):
when we had our initial space,like one of the guys was one of
the founders of Uber.
The other one was doing JamesBond titles.
The other one was a professor inmicro economics.
Like we had people that, we'renot related in terms of their
field, but it's like, oh, likemaybe there's something you've
(32:46):
learned or something that you doin your craft that that concept
applies to me and my business ina different way.
That's actually like where themagic happens, right?
You go to the same place everyday.
You work on the same projectsevery day with the same people
every day.
You go drive down the same routeevery day.
(33:08):
Like there's stagnation there.
But if you put yourself in aroom with other people who think
about different things,different ways, if you change
the route you take to work or gosee other parts of the world, I
think like, it's human nature tokind of connect the dots and be
like, what if I take that andapply that to me?
(33:28):
And maybe that's novel or maybethat's kind of a unique
advantage.
SPEAKER_01 (33:34):
Okay, so you've talked about being persistent,
having grit.
You talked about how you alwayslike to learn.
So I'm gonna call thatcuriosity.
All these things have shaped whoyou are as an entrepreneur.
What else do you think is, makespeople a good leader?
SPEAKER_00 (33:56):
I think it's two things to me.
You know, I like to say nice,like being a nice person.
I remember getting beat up once.
We were had the opportunity towin clients from a company that
was selling.
And they were like, whatdifferentiates you?
And we were like, really nicepeople.
We're really nice people to workwith.
(34:18):
And they laughed us out of theroom.
They're like, this is not.
That's a terrible.
What is that?
And that always stung.
But I think it's two things.
I think it's empathy.
Being empathetic.
You know, like just empathy.
respecting that people havedifferent paths and different
(34:38):
stories and are in differentparts of their lives and maybe
are dealing with stuff that youdon't see or know and just like
understanding appreciating thatand not trying to solve it but
just saying like hey man I feelyou I'm here for you and I
support you but not necessarilylike being like and let's fix it
(34:59):
and I learned that with my wifeit's like you know it's like
sometimes like you know it's notsolution engineering it's just
like yo that sucks like man ithink that really goes a long
way and the other part for meand different i think people
handle this different is beingvulnerable it's vulnerability i
think you see that like withpeople that people tend to
(35:23):
really connect with people thatare vulnerable you know like
those folks that sort of justlike on this persona that like
their doesn't stink you know andthey've never messed up like
everyone knows that's bull likeyou know what i mean everyone
knows that that is not how theuniverse works and i think those
(35:47):
that are kind of willingpublicly but especially with
their team to say i don't knowor this hurts or like when when
one design turned uh 14 i won umWe did these awards and I won
most likely to cry.
You know what I mean?
But I think that was a nicething, right?
(36:10):
That made me feel good and notbad.
But I think that reallyresonates with people because if
you're empathetic to whatthey're going through and then
you're vulnerable with whatyou're going through, it builds
a lot of trust.
It builds a lot of...
Flexibility when things don't gowell and when you need to rely
on people, they are willing tobe there and help you and kind
(36:34):
of see you through.
So empathy and vulnerability.
Those are my words.
SPEAKER_01 (36:41):
Well, Sam, thank you for speaking with us today.
If people want to learn moreabout DeskPass and what you do,
what is the best way to do that?
Yeah.
SPEAKER_00 (36:51):
We're easy to access and find on a personal front.
My, you know, SammyRosen.com hasa link to all my world, right?
And then DeskPass.com,Instagram, and it's just at
DeskPass.
SPEAKER_01 (37:08):
Well, thank you so much for speaking to us,
speaking with us today.
Honestly, it was a greatconversation.
You offered excellent tidbits ofinformation that I know other
entrepreneurs are really goingto hang on to and learn from.
So thanks for your time today,Sam.
SPEAKER_00 (37:27):
My pleasure.
Thank you both so much for thetime and the platform.
SPEAKER_01 (37:33):
And thank you for listening to our podcast today.
Don't miss our next episode ofFinding Reverie, an
entrepreneur's journey comingsoon.
Thank you.
SPEAKER_01 (00:03):
Thank you so much.
(00:34):
Hi, Sam.
Thank you for joining us today.
Hi,
SPEAKER_02 (00:36):
Sam.
I'm so excited you're here,mostly because you're a
brilliant human, but alsobecause the people that we have
in common are way too fun for usnot to have you here.
I know it's going to be a greatconversation today.
Thanks for coming.
SPEAKER_00 (00:52):
Yeah, thank you guys so much.
It's nice to meet you, and I'mexcited to chat as well.
SPEAKER_01 (00:58):
All right, Sam.
So let's start off.
Tell us about DeskPass, what youdo, and what inspired you to
start the business.
SPEAKER_00 (01:08):
Absolutely.
So DeskPass is a marketplacethat connects companies and most
importantly, the people who workat those companies with all
sorts of incredible workspacesall over the world.
So co-working spaces that areavailable to book by the day or
the hour.
So we sell basically meetingrooms by the hour, desk by the
(01:29):
day, private offices, all reallyshort term and pay as you go.
And what inspired this idea wasI came across coworking about 17
years ago, which like hurts myhead when I say that out loud
and I have to always doublecheck.
But I came across this conceptof coworking in New York City
(01:54):
And I had never heard of itbefore.
And no one had heard of itbefore.
There were about 300 of theseworkspaces in the world.
If you wanted to find them, youhad to go to the coworking wiki.
And there weren't any inChicago.
So myself and my partner, Pat,we have a design and branding
(02:19):
firm.
And we're like, we have someextra office.
There are no co-working spaceshere in Chicago.
Let's open one up.
And from that, I just sort offell in love with this notion of
where and how we work and theidea that the office didn't have
to be what I think most peoplethink of it as still today.
SPEAKER_02 (02:43):
That is so cool.
And I just think to myself,like, It's hard for me to even
remember a time where we didn'tknow what coworking was because
it's so part of how we do lifenow.
But you're right.
There was literally a time notthat long ago where it was not
so mainstream.
(03:03):
You had never even heard of thisconcept before.
SPEAKER_00 (03:07):
Yeah, there were no movies or TV shows about WeWork.
SPEAKER_02 (03:12):
Right?
Not at that point.
So that had to have been alittle bit mind-blowing.
When you saw it, was itinstantly you were like, that
makes so much sense?
SPEAKER_00 (03:21):
Yeah, it was a really obvious idea that I had
never considered before.
For me, I was traveling to NewYork a lot, and I was staying
with my girlfriend and workingout of her really...
crappy apartment and it was anice apartment and she was
wonderful but it was just messyand I had bad cell phone and bad
(03:45):
internet and I would Didn't knowwhat to do.
So I started working at the cafedown the street called the
rabbit hole.
And I realized they didn't wantme there because I'd sit there
all day.
I'd have two coffees and a bageland I would take their expensive
Brooklyn real estate away frombetter paying customers.
And the name of the coworkingspace was called the change you
(04:06):
want to see, which I thought wasthe dumbest name when I heard
it.
But in hindsight, It's thegreatest name because it really
did.
I walked into a room of a bunchof really fascinating people and
arts and media and design andtechnology that were just
sharing space together.
(04:27):
And I was like, oh, duh.
But you ask anybody at thattime, there was, do you know
what?
coworking is.
Everyone would say the samething.
They'd say, co-what?
And you'd be surprised at howmany people still don't know
what coworking is.
But we've come a long way.
SPEAKER_02 (04:46):
Yeah, I guess in Chicago, we finally caught up,
right?
But outside of Chicago, maybethere are still some cities that
haven't had exposure just yet.
I guess we forget about that,don't we?
SPEAKER_00 (04:59):
Yeah, we live in a big city with a like a pretty
progressive scene.
But I still like, when I'm in anUber or a cab, people say, you
know, what do you do?
And you'd be surprised when Isay co-working, how many people
are like, what?
What's that?
But it's every day, more andmore people.
I
SPEAKER_02 (05:18):
love that.
It's brilliant.
I mean, we have an office thatis a co-working location.
And so I guess, and we've beenthere for quite a while now.
And so to me, it's just likepart of life.
I can't even...
Like I said, as you were sayingit, I was like, oh my gosh, you
are right.
Like there was literally a timewhere this wasn't a thing.
(05:39):
I can't remember it, but wow.
So yeah, thank you for sharingthat.
That was a fun, just kind oflittle rewind back to a totally
different time.
A
SPEAKER_00 (05:51):
very different time.
SPEAKER_01 (05:54):
So Sam, how did your career begin?
Was owning your own businessalways kind of a goal that you
wanted to pursue?
Or did it happen more byaccident?
SPEAKER_00 (06:07):
I'm a unique, I think, nice little Jewish kid
from the North Shore of Chicagoin the sense that my mom is a
painter, my dad...
directed and produced televisiongrowing up.
So unlike my, I think my peerswhere it's like, you can be
(06:28):
whatever you wanna be when yougrow up, but we'd prefer if
you're not a doctor or a lawyer.
So I've always had sort of thisautonomy and support to like
kind of explore and do what Iwant, which is lucky and plenty
privileged.
I've always been entrepreneurialsince I was a little kid.
(06:48):
You name it, right?
When CDRs came out trying tosell mixtapes to kids in junior
high or writing poetry books orbuilding websites.
That was always very intuitiveand natural to me, and I never
(07:08):
really considered...
anything else until recently.
But I, you know, I think whenyou're young and you, you're
kind of ignorant to the risksassociated with starting your
own thing and building your ownthing.
And it's kind of a blessing inthe sense that I married, I got
(07:34):
two kids, I got a mortgage,right?
The idea now of starting a newbusiness and the risk associated
to it would make me think aboutit differently.
But I just didn't, it's just howmy brain's wired and I didn't
know any better.
So yeah, I've always beenentrepreneurial.
My first like substantivebusiness, which turned 20 years
old this year, which is wild,right?
(07:58):
is called One Design Company,which is a digital branding
agency that does reallywonderful design and brand and
like interactive work.
And that has been the most kindof consistent foundation of me
of just thinking about designand how it meets technology.
And then as I've learned aboutnew ideas and concepts like
(08:21):
coworking, it's given me a bitof a platform to like, riff and
explore and try new things.
So yeah, for better, for worse,I think this is the way for me.
SPEAKER_01 (08:34):
So you're not a single entrepreneur.
You're actually like a doubleentrepreneur.
SPEAKER_00 (08:38):
I'm more than that.
But yeah, I'm the real deal, Ithink, just in terms of I don't
know any better anymore.
Yeah.
SPEAKER_02 (08:51):
Isn't it so great though?
I love that you included thewhole bit about like when you're
young enough and you don't evenrealize the risks associated
with it.
SPEAKER_00 (08:59):
Yep.
SPEAKER_02 (09:00):
Because then when you do it once, you got to do it
again and then you got to do itagain.
It is one of those things Ithink that just becomes so easy
to, it's like your newobsession, you know?
Because every single time is sodifferent, but there are enough
(09:22):
similarities that you kind offeel a little bit more bold and
then you just kind of go inbigger.
Has that been your experience?
Like, have you been superexcited?
Like once you do one thing to goto the next thing, like how does
that look for you?
Or do you do it all at the sametime?
Are you like...
Boom, boom, boom,
SPEAKER_00 (09:38):
boom, boom.
I love the beginning, right?
Like I love the zero to like upand running phase.
I love the idea of like, I havean idea and trying to make that
idea like a real thing.
I think a lot of people arescared of that because they have
an idea.
And then this idea, you know,this, how do I get from here to
(10:00):
there?
And they're like looking up andthey're like, man, I don't, it's
such a big step.
And in reality, it's a bunch oflittle steps.
You know what I mean?
And I think I learned thatearly, and that's helped me be
able to, like, when I have anidea, deconstruct it into, like,
all right, like, one bite at atime.
I have a lot of friends now inmy life that, like, have taken
(10:25):
more of a traditional sort of...
path of taking a job and workingfor a business.
And then they have an idea andthey're inspired.
And because they know me asthey're like, you know, this is
kind of my persona.
They're like, should I do it?
Should I do it?
And I often feel like I'm theguy.
They come to me with their,they're like at the ledge of a,
(10:48):
you know, at the ledge.
And they're like, should I jump?
Should I jump?
And I'm like, dude, I'm like,push them.
I'm like, go.
Like the worst thing happens isyou fail.
And then you learn a lot ofstuff and you're probably going
to, that'll help you go back towhat you were doing before and
give you more perspective.
So, but again, ignorance isbliss.
(11:09):
And I think I learned this at anearly age and I was very lucky
enough to be in a situationwhere I could afford to screw
up, you know?
SPEAKER_02 (11:18):
Well, I have to ask you.
So, let's say somebody'slistening to this and they're on
that ledge.
What do you usually recommend?
If there was one first littlesmall step, because I love that.
I love that you said, it seemslike this big, huge step, but
it's really a bunch of littleones.
Without having any clue of who'slistening to this and what it is
(11:40):
that they're considering jumpinginto, what's the first thing
that you would say to rip thatband-aid off, get real bold?
What is that first little step?
SPEAKER_00 (11:49):
Obviously, technology has changed so much
as it relates to this andimproved.
So I'd probably think about it alittle bit differently today
because there's such good toolsthat exist to help you break
things apart.
But again, I think it's likebreaking things apart into
smaller chunks.
It's, okay, you want to start abusiness.
(12:11):
Like, what's the...
what's the first thing you haveto do to start a business?
And what are the differentpieces?
People get tied up aboutincorporating a business and
insurance and really stuff thatis not scary.
It's not complicated.
Today, I know there's this wildAI bandwagon that's happening,
(12:33):
but the tools have never beenbetter to be able to put
together a concept and get helpand say, hey, this is my idea.
How should I get started?
And be spoon-fed like, okay,like step one, step two, step
three.
But I always think like havingthe right people around you to
(12:55):
support you, finding a mentor,finding someone who's done this
before who can just help you,advise you, you know, just kind
of soothe you when you'rescared, but be able to kind of
point you in the rightdirection.
I've leveraged that my wholecareer.
I'm so lucky.
And I think most people havesomeone in their life that can
say, here, here's where to look.
SPEAKER_02 (13:17):
Yeah.
We've heard a lot of people whenyou're talking with the founders
or the entrepreneurial mindedpeople, community is huge, which
obviously it's, goes back to theco-working concept too.
When you're working on your ownlike that, it's so important to
have a community around you.
(13:37):
So I'm really glad that you saidthat.
I think too, knowing how toproperly use AI or the
technology for what it's therefor and knowing when to sub the
person in is equally important.
UNKNOWN (13:53):
Yeah.
SPEAKER_00 (13:54):
It's never been easier.
It's never been easier to, inone button, you can set up and
incorporate a business inDelaware and have a bank account
and an incorporation andoperating docs.
That's insane.
In another button, you can havea business plan written by a
robot.
We live in amazing times.
SPEAKER_02 (14:16):
I mean, it's pretty insane.
ChatGPT created a picture ofwhat what it thought my dogs
would look like if they werehuman beings.
It can give you a step-by-stepon maybe where to start.
There are some really coolthings happening.
I want to see those
SPEAKER_00 (14:35):
pictures.
SPEAKER_01 (14:37):
You know what?
Dogs were very handsome, I mightsay, as humans.
They
SPEAKER_02 (14:42):
really were.
They really were.
And there's something weirdabout seeing a picture of your
animals as humans where you'relike, of course, that's you.
Absolutely.
I love
SPEAKER_00 (14:53):
novel use cases, and that's pretty high on the list.
I'm going to go home and seewhat my cats look like.
SPEAKER_02 (15:00):
You should.
You should, but I have to warnyou, sometimes they don't turn
out great.
So it's all about a good prompt.
So as with all things with AI,make sure your prompt is pretty
solid or you're in trouble.
No, but I think that's such animportant point, though, that
you're making is that barrier toentry and the level of access
people have to resources.
(15:22):
What an amazing time to bealive.
If you are entrepreneurial innature, or even if you're not,
but you've got a really greatidea, It is all right at your
fingertips.
So easy.
SPEAKER_00 (15:32):
Yeah.
SPEAKER_02 (15:32):
So easy.
SPEAKER_00 (15:33):
The other thing I would say is people are often
scared about sharing their ideabecause someone's going to steal
it.
SPEAKER_02 (15:42):
Oh, someone's going to steal it.
Oh, yeah.
SPEAKER_00 (15:45):
I've always thought that is not the right way of
looking at things.
If it's a great idea.
Someone's doing it.
So like, and no one's going toknow about it unless you share
it.
So I think that's the otherpiece where people are like, I
can't tell you until it's readyor fully baked or I need to sign
a non-disclosure.
(16:05):
And it's like, look, like ifthis is a good, I'm not going to
do your idea.
And if this is a good idea, likeit's probably being done or
you're really early and you gottime.
SPEAKER_02 (16:17):
Well, I'm glad you bring that up because I think
there are definitely times wherepeople get into that headspace.
And to me, that's scarcitymindset.
And I think it's an importantreminder for all of us, like,
because there will come a timewhere you're feeling like that
little bit of threat, but it'slike, oh no, you're going to
need so many people behind youknowing about what you're doing
(16:37):
and cheering you on and wantingto do what you're doing.
And like all of those things,that's going to be important for
your success, not the other wayaround.
SPEAKER_01 (16:44):
All right, Sam, I want, to ask you about some of
the obstacles or maybe let'seven call them failures that you
faced early on and tell us howyou overcame them and how they
even led to growth.
SPEAKER_00 (17:00):
Yeah, I feel like building a business is like,
building a fire from scratch,you know what I mean?
And sometimes it goes out andyou have to start over and
sometimes, you know, like youcan control it and sometimes it
controls you.
I think for me, one of my giftsis kind of seeing where things
(17:23):
are going.
So for me, with coworking, andsort of the future of work, a
lot of it became a lot moreobvious when COVID happened, but
we were so early.
To me, it was like a duh, likethis makes perfect sense.
I'm in River North in Chicago.
(17:44):
I'm looking across the street atthis building.
This building has been here for,I mean, I've been here for 12
years.
This building's been hereforever.
it was always mostly emptyduring most of the time.
These buildings have beenunderutilized for a long, long,
long time.
And I think the world isstarting to notice that more and
(18:05):
more.
For me, timing.
We were so early where themarket didn't exist.
When we started, we were sellingsoftware to manage these spaces.
And there weren't that many ofthem.
Everyone was so different thatthey were very complicated.
Like, it was hard to build aone-size-fits-all solution.
(18:26):
It was very complicated tobuild.
And they didn't have money.
They were really frugal.
It was like the trifecta of abad market.
So part of it is just stickingwith it, right?
Learning.
Iterating.
Most importantly, talking topeople, your customers,
listening to them.
(18:47):
Like...
It's a conversation, it's adialogue.
And for me, we had so manysetbacks because it was just too
early and it didn't exist yet.
So part of it is persistence.
Like if you ask, I think, youknow, one of my favorite Chicago
entrepreneurs, Mark Lawrence,who started Spot Hero, and he
(19:08):
said this once and I reallyappreciated this.
And he said, like, the numberone trait that I see for great
entrepreneurs is persistence.
is great like it's hard andyou're gonna fall on your face
and you're gonna want to cry andyou're gonna want to quit and
you're gonna want to take a joband you're gonna like doubt
(19:29):
yourself and you're gonna seeother people do what you're
thinking and have more successand you're gonna be like i suck
um waking up trying again overtime and not giving up.
And that's not to say youshouldn't ever give up, but I
think like more than intellect,more than intelligence, more
(19:52):
than access to capital,persistence of trying to solve
the problem, talking to thepeople you're trying to help,
listening to them, incorporatingthat feedback and evolving that
is I think what drivessuccessful people.
(20:14):
The other thing I would say is,which is what I think makes up
really good entrepreneurs andjust successful people in life.
It's not just related tobusiness.
It's that bad things are goingto happen, right?
And the people that I know thatare the most successful and the
(20:36):
happiest, and those are notmutually exclusive.
When those bad things happen,they extract the good out of it.
Even if they buy something for Xand sell it for X minus 50%.
Like they don't say, oh, thissucked.
(20:57):
I lost all my money.
They say, I learned a lot.
I had great, I made my, learnedmy best friend.
I learned what not to do.
I, And I think that thatmentality of like, there's
medicine everywhere, there'slike lessons everywhere.
And the people who not just arethe best at business, but I
(21:19):
don't know, often the happiestof life are the people who say,
there's a lot of good stuff hereand I'm going to take that and
I'm going to move.
That's what's going to propel meforward, not the negative side.
SPEAKER_02 (21:33):
Such an important reminder.
I feel like we oftentimes forgetthat we only see what we're
looking for.
And so if we're putting itthrough, if we're living this
life and having theseexperiences through a negative
lens or through a failure lensversus can I see the
opportunities and the lessonsand everything else?
I mean, two completely differentoutcomes that could have been in
(21:59):
a completely differentsituation.
Everything else was the same.
It's just how you choose to lookat it.
And then that determines, it hassuch a ripple effect and
determines so much movingforward.
I love that.
That is such a criticalreminder.
Brilliant.
Thank you.
SPEAKER_00 (22:17):
It's also what you see, right?
I mean, you see people likefriends and Instagram or
whatever, where you just see thehighlights, right?
You see entrepreneurs where theyjust post the wins and you can
be really successful at puttingforth an image, which is, I
(22:39):
don't know if it's disingenuous,but it's like, it is not the
whole picture.
And I can't believe how manytimes in my career I've thought,
I've misperceived where peopleactually were And sort of
overinflated their success ortheir traction or whatever.
When like later when things are,you know, when you could talk
(23:02):
about it and you have aconversation and it's like, no,
like more than most are goingthrough the same pain and trials
and tribulate, like the samestuff you are.
there, you know, you just can'tsee it.
So like there, there are veryfew stories I think of people
(23:23):
just like who get to avoid that.
SPEAKER_02 (23:26):
Yeah.
Yeah.
I, I, I would be interested inhearing if there was someone,
but what a crappy story.
I mean, like, like what would weeven be watching?
You know, it's like, there'snothing interesting that happens
and, if all we're watching isone win after the next and oh,
it's so easy, it'd be over infive minutes and we'd be like,
(23:49):
can't get that five minutesback.
I learned literally nothing.
There's nothing interestinghere.
But I wonder if it exists.
SPEAKER_00 (23:56):
Well, it's funny you say that.
So like when, you know, one ofour early competitors was
WeWork, right?
And WeWork, it was like,Competing against WeWork as a
co-working space operator in theearly days was, like, this
notion of, like, these guysdon't...
(24:19):
Like, gravity doesn't apply tothem.
Like, when I jump, I go thishigh.
But when they jump...
Like, money just flies out ofthe...
And it was just, like...
it seemed like they could do nowrong that they were just
defying the fastest.
And they were like, we're doingthe same thing, you know?
And then when the money machinestopped, you're like, Oh,
(24:42):
actually
SPEAKER_02 (24:42):
there's the story.
SPEAKER_00 (24:44):
There's a movie about
SPEAKER_02 (24:48):
that one.
That one is maybe not what itseems.
Yeah.
Yeah.
I mean, the whole thing isfascinating.
And I think, um, It's reallyfunny, you know, once you can
see behind that curtain, whatyou see sometimes is not what's
actually going on.
And if we just like measureourselves compared to what we
(25:09):
think we know.
Totally.
Like not only is it just stripthe joy right out of it, but
also these are not apples toapples situations like that is
just not a good form ofmeasurement at all.
But it's so hard not to do that.
SPEAKER_00 (25:23):
Yeah, it's human
SPEAKER_02 (25:25):
nature.
Why do we do that to ourselves?
SPEAKER_00 (25:27):
There's, there's, there's gotta be a reason.
SPEAKER_02 (25:29):
Could you figure that out and then we'll have you
come back and then we'll talk
SPEAKER_00 (25:33):
all about.
Okay.
I'll tell you in about fourminutes.
SPEAKER_01 (25:39):
Okay.
So Sam, this is probably, youshould probably take it further
back.
Cause I, you had already been anentrepreneur when you started
desk cast, but is there onething that you now know in this
industry, time in yourentrepreneurial journey that you
wish you knew when you started?
SPEAKER_00 (25:58):
You know, everyone's just making it up.
Like no one, no one's done thisbefore.
Nobody, many people have likerun a couple of businesses back,
but like they didn't liveanother life that they can
consciously, like we're all justwinging it.
You know, we sold desk pass lastyear and I started working for a
(26:19):
unbelievable, like it's thiscompany called Yardi.
It's the biggest propertytechnology company in the world
and it's run by someone who'sabout twice my age who started
this business 40 years ago onhis MS-DOS machine and like has
built a 10,000 personmulti-billion dollar empire and
(26:40):
you know going into that machineas an entrepreneur you're like
oh you think he has it all he'slike you know this is his dream
and his, he made it, how he madeit all up.
But again, I think you look, youuse these like Titans and you're
like, they're all winging it,man.
And I think when you realizethat it makes it like a little
(27:04):
less holy, like a little lesssacred.
And you realize like, we're, wegot one, we got one shot at
this.
So like, let's just have, do ourbest to have fun.
And it's fun to see how otherpeople make, make it all up.
Yes.
It's a thing.
SPEAKER_02 (27:22):
It's a real thing.
And it's so refreshing to, tohave people who are like, I
mean, I don't know.
We've never, we've literallynone of us have done life
before.
So like every time that we gothrough and do this, I mean,
like we're, we're waiting in it.
(27:42):
That is refreshing.
You meet so many people thatmake you feel like there's one
right way of doing all thethings, and if you're not doing
it that way, you're just notdoing it right.
But it's like, in what world?
SPEAKER_00 (27:55):
Yeah, in what world?
It's like, wait, you haven'tlived before?
You know what I mean?
You might be 40 years ahead ofme, but this is still your first
go-round, you know?
UNKNOWN (28:09):
Yeah.
SPEAKER_02 (28:10):
How quickly things change now.
I read something.
I'm not even going to try toquote it because I would just
sound like a moron.
The speed that things turn overand change and move and shake.
None of us have done thisbefore.
Literally none of us.
Even that person with 40 yearson, any of us, that literally
means nothing anymore becausewhat happened yesterday is now
(28:33):
so far out of date by 12 yearsin some old way of measuring
time.
It's like it moves so rapidly.
Literally none of us have donethis before.
Get some confidence.
Like everybody's sitting aroundthe table from you.
We should all just feel asconfident as the next person
because nobody knows.
SPEAKER_00 (28:53):
Yeah.
SPEAKER_01 (28:54):
But therein lies the hardest part is, is, trying to
feel confident you know i meanthere's a lot of people who
think i can't start a businessuntil i know this this this this
this this this and this and theybecome paralyzed in you know
their fear they become stuck inthat in not moving forward and i
do feel like in everyconversation we have with
(29:19):
entrepreneurs the differencebetween them and me who is not
who would forever get stuck inmy fear is just that.
You guys are willing to take theleap, even if you don't have all
the answers, and I'm stucktrying to find all the answers.
SPEAKER_00 (29:37):
But also, like, I don't know.
You fail enough, you know, acouple times, and it's less
scary, right?
the people who are like, Hey, Ilearned a lot.
I learned not what to do.
And then it becomes less scary.
It's like, okay, like, you know,your, your family will still
love you.
And if you're a good humanbeing, your people will still be
(30:00):
there for you.
They care way less than youthink.
Like it's so often you tie youridentity to what you do, but
like, that's not what otherpeople do.
They like tie you to you.
And, and, and that's whatmatters.
You know, I love this, um, therewas a art collaborative in
Austin and they made this posterand I have it when I go
(30:21):
downstairs, which is like wheremy stuff is and at my house.
And it says, tie your shoes,pack a good lunch and remember
that we're all in this together.
And I just like, that's it, man.
Like we're just, we're all doingthe best we can.
SPEAKER_02 (30:38):
Are you even a respected entrepreneur if you
haven't failed at least once?
SPEAKER_00 (30:44):
There's so much.
So much medicine in that.
And if you haven't done it yet,then time's ticking.
Unless it's maybe a WarrenBuffett.
I think he might make it.
SPEAKER_01 (30:59):
Sam, so in this kind of rapidly changing AI, moving
forward, changing just kind ofthe whole landscape of things,
how do you prepare for thefuture of your business?
SPEAKER_00 (31:13):
I love to learn.
Like...
I love learning.
I love reading.
I love podcasts.
When I do my errands and mychores, just listening,
especially as it relates toentrepreneurship, how other
people do stuff.
I just learned some amazingstuff this last weekend about
(31:36):
workflows for the future ofwork, but it's not just work
stuff.
I just like learning about howthe world works and how other
people do things and how thingslike, you know, like the science
or just sort of the mysterybehind different people in
different stories.
And I just like, to me, thatreally helps like to, to your
(32:01):
point, like it, things move sofast that you have to keep
listening and kind of tap in.
So for me, podcasts and booksand surrounding myself with
people that really inspire meand are doing things way
different to me.
This is like one of the reasonscoworking is so rad.
And one of the reasons that Ifell in love with it early on
(32:23):
when we had our initial space,like one of the guys was one of
the founders of Uber.
The other one was doing JamesBond titles.
The other one was a professor inmicro economics.
Like we had people that, we'renot related in terms of their
field, but it's like, oh, likemaybe there's something you've
(32:46):
learned or something that you doin your craft that that concept
applies to me and my business ina different way.
That's actually like where themagic happens, right?
You go to the same place everyday.
You work on the same projectsevery day with the same people
every day.
You go drive down the same routeevery day.
(33:08):
Like there's stagnation there.
But if you put yourself in aroom with other people who think
about different things,different ways, if you change
the route you take to work or gosee other parts of the world, I
think like, it's human nature tokind of connect the dots and be
like, what if I take that andapply that to me?
(33:28):
And maybe that's novel or maybethat's kind of a unique
advantage.
SPEAKER_01 (33:34):
Okay, so you've talked about being persistent,
having grit.
You talked about how you alwayslike to learn.
So I'm gonna call thatcuriosity.
All these things have shaped whoyou are as an entrepreneur.
What else do you think is, makespeople a good leader?
SPEAKER_00 (33:56):
I think it's two things to me.
You know, I like to say nice,like being a nice person.
I remember getting beat up once.
We were had the opportunity towin clients from a company that
was selling.
And they were like, whatdifferentiates you?
And we were like, really nicepeople.
We're really nice people to workwith.
(34:18):
And they laughed us out of theroom.
They're like, this is not.
That's a terrible.
What is that?
And that always stung.
But I think it's two things.
I think it's empathy.
Being empathetic.
You know, like just empathy.
respecting that people havedifferent paths and different
(34:38):
stories and are in differentparts of their lives and maybe
are dealing with stuff that youdon't see or know and just like
understanding appreciating thatand not trying to solve it but
just saying like hey man I feelyou I'm here for you and I
support you but not necessarilylike being like and let's fix it
(34:59):
and I learned that with my wifeit's like you know it's like
sometimes like you know it's notsolution engineering it's just
like yo that sucks like man ithink that really goes a long
way and the other part for meand different i think people
handle this different is beingvulnerable it's vulnerability i
think you see that like withpeople that people tend to
(35:23):
really connect with people thatare vulnerable you know like
those folks that sort of justlike on this persona that like
their doesn't stink you know andthey've never messed up like
everyone knows that's bull likeyou know what i mean everyone
knows that that is not how theuniverse works and i think those
(35:47):
that are kind of willingpublicly but especially with
their team to say i don't knowor this hurts or like when when
one design turned uh 14 i won umWe did these awards and I won
most likely to cry.
You know what I mean?
But I think that was a nicething, right?
(36:10):
That made me feel good and notbad.
But I think that reallyresonates with people because if
you're empathetic to whatthey're going through and then
you're vulnerable with whatyou're going through, it builds
a lot of trust.
It builds a lot of...
Flexibility when things don't gowell and when you need to rely
on people, they are willing tobe there and help you and kind
(36:34):
of see you through.
So empathy and vulnerability.
Those are my words.
SPEAKER_01 (36:41):
Well, Sam, thank you for speaking with us today.
If people want to learn moreabout DeskPass and what you do,
what is the best way to do that?
Yeah.
SPEAKER_00 (36:51):
We're easy to access and find on a personal front.
My, you know, SammyRosen.com hasa link to all my world, right?
And then DeskPass.com,Instagram, and it's just at
DeskPass.
SPEAKER_01 (37:08):
Well, thank you so much for speaking to us,
speaking with us today.
Honestly, it was a greatconversation.
You offered excellent tidbits ofinformation that I know other
entrepreneurs are really goingto hang on to and learn from.
So thanks for your time today,Sam.
SPEAKER_00 (37:27):
My pleasure.
Thank you both so much for thetime and the platform.
SPEAKER_01 (37:33):
And thank you for listening to our podcast today.
Don't miss our next episode ofFinding Reverie, an
entrepreneur's journey comingsoon.
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