All Episodes

October 14, 2024 19 mins

Wayne Turmel is joined by Sam Rosen, the founder of Deskpass, to explore how the office landscape has changed in recent years. Sam shares his journey from opening one of Chicago’s first co-working spaces to developing tools that connect companies and remote workers with flexible workspaces. They discuss the evolving role of offices, how companies can make strategic real estate decisions, and the benefits of offering co-working options to remote and hybrid teams. Sam also dives into the differences between designing workspaces with a human-centered approach versus the traditional real estate mindset. Tune in to discover how you can leverage flexible spaces to improve productivity and retain top talent.

Key Takeaways

  • Flexible workspaces provide a valuable alternative to traditional offices, offering professional environments tailored to diverse work needs.
  • A human-centered design approach prioritizes worker needs over merely filling office space, unlike traditional real estate perspectives.
  • Companies are reducing their office footprints to save costs while using co-working spaces to maintain access to professional environments.
  • Proximity and convenience are key benefits of co-working spaces, making them ideal when working from home isn't suitable.
  • In-person meetings should be reserved for deep collaboration or cultural reinforcement, with a focus on asynchronous work whenever possible.
  • Successful remote companies prioritize culture, communication tools, and processes over physical office space.
  • Access to flexible workspaces helps attract and retain talent, expanding the hiring pool and supporting employees' varied work preferences.

Featured Guest

Name: Sam Rosen

Bio: Sam Rosen is the co-founder and CEO of Deskpass, an online marketplace connecting teams and individuals to thousands of coworking spaces and conference rooms across the country. A creative problem solver, Sam's passion for coworking began with co-founding The Coop, Chicago’s first coworking space, and he has since become a recognized entrepreneur and voice in the design community. Prior to Deskpass, he co-founded The Post Family art collaborative and One Design Company, a digital branding agency that blends research, communication, and design for top brands.

https://www.linkedin.com/in/sammyrosen/

https://www.deskpass.com/

Timestamps

00:00 Introduction to Sam Rosen and Deskpass
01:03 Sam’s Background in Co-Working and Design
02:05 The Evolution of Office Spaces and Remote Work
03:19 Design vs. Real Estate: What’s the Difference?
04:51 Advantages of Co-Working Spaces
07:09 How to Use Deskpass for Remote Work Travel
08:17 Making Flexible Workspaces Work for Your Company
10:00 Real-Life Examples of Deskpass in Action
13:15 Keeping Culture Alive in Remote Teams
17:19 Deciding When to Meet In Person
19:08 Conclusion and Resources

Related Episodes

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:07):
Hello, everybody.
Welcome back to the Long DistanceWorklife,
the podcastwhere we attempt to help you thrive.
Survive,generally keep the Weasels Hat Bay
when we are dealing with remoteand hybrid work.
My name is Wayne Trammell.
I am the subject matter for remote work

(00:29):
and the evolving workplace at the KevinEikenberry Group.
My usual partner and producer,Marissa is not here today.
The good news is
that means we have an interviewwith a fabulous guest,
in this case, Sam Rosen from Desk Pass,
who is going to talk to usabout the changes

(00:51):
that digital work have wrought upon usover the last couple of years.
And so, with no further ado,joining us from Chicago is Sam Rosen.
Hi, Sam. Hi, Wayne.
Thanks for having me, man.
Thank you for being had a, real quick.
Who are youand what steps pass and why do we care?

(01:13):
Good question.
I'm sam, and, I run
a little business called that spaceI've been in,
sort of the intersectionof design and technology
and wherein how we work for about 15 years.
So I startedby, started a branding design agency
and then opened the first co-working spacein Chicago,

(01:35):
where there are about 300in the whole world now.
There's 40, 50,000.
And since then, I've been buildingtools and technology around this problem.
So today, I work on desktops.
I'm the founder of that space.
And that space is a toolthat really connects individuals
and companieswith thousands and thousands of fantastic,

(01:57):
flexible workspaces, co-working spaces,you know, places to book a desk
for a day, meeting for an hour,private office, all on demand.
And that's that's what I do.
All right.
So whenever anybody creates a technology
or does anything like that, they'reclearly trying to solve for a problem.
So what was the problemyou were trying to solve for,

(02:20):
with past?
Yeah.
You know, it's funnybecause a lot of people in this space now,
come from financeand come from real estate.
And I've always come from design,
and just trying to solve problemsfor humans.
So, coming across co-workingreally, really early realized
that was a really interesting solutionto offer a place

(02:42):
for people who want to workbut necessarily don't work
for the same companyand just are looking for a space
to get work done nearby. So,
and I found that to be really interestingand a new problem.
And then the, the other problem was,and I think this is more clear
than ever,is, offices have always been pretty empty.

(03:02):
Officesare traditionally fairly underutilized,
and that's one of the biggest assetclasses in the world.
So the opportunity to create somethingout of empty office space
and share it with peopleso they can be happy and get
good work done, is seemedlike a good problem to solve.
Now. You said something a moment ago,which I've dealt with remote work

(03:23):
for 25 years.
I should have thought of this,
and for some reasonI had a blinding flash of the obvious,
which is it makes sense for real estatepeople to get involved in this,
because there's all these officessitting empty,
and how are we going to finduses for them?
What in your mind is the differencebetween coming at it from a real estate

(03:45):
standpoint, where it's desks and roomsand whatever, and a design standpoint?
You know, I think the perspectivewe've always had is like,
who's way, what is what is waiting live?
Who does he live with?
Where can he focus and get work done?
And how do you builda really brilliant environment for Wayne

(04:05):
to get his best workdone, irrespective of everything else?
And I think often folks that come fromreal estate and finance are just
they're they're tryingto put pegs and holes, right.
Which is there's empty office space.
Let's fill it up.
And I think for me,from the design perspective,

(04:25):
I think for a long timethe experience for workers was really
driven around, you know, thethe bank that owns the building,
the management companythat manages the building,
you know, supporting the ownerof the company that owns the company
and building a financial arrangementthat works for all those parties,

(04:46):
but less so, like Wayneand like what works best for Wayne today.
And I think that's where I come fromis like, how do you everyone has different
needs as workers depending on what companythey work for, what role they're in.
I got two little kiddos
that live in the suburbs,you know, like my kids have Covid today.
Like my needs are different todaythan yesterday, right.

(05:07):
And, and I think that'swhat I'm really interested is solving
problems around the humanand less around like X, Y, Z Corp and
you know, and x, y, z bank.
Okay.
So we've done our burnthe patriarchy death to make.
Peace with this.
So let's get really practical.

(05:30):
A lot of people, I think, think of I'meither working at home
or I'm in the office.
What are some of the advantagesof these kind of third spaces?
Because to me, having other humans around
is not the most beneficial piece of this.

(05:50):
Yeah.
But I have used spaces like thisbefore, so,
you know, if somebody is thinking aboutwhen does this make sense?
When does it not?
What's the the answer there.
Yeah.
Look, I think there's a lot of thingsthat people will say
about what makes a great workspace.
But I think the underlying thingis proximity distance.
Right.
Like if I can't work from homebecause my kids are home

(06:15):
or I don't have a suitable workenvironment, like trying to find a place
close to me that's convenient to me whereI don't have to commute or schlep or go.
That's a that's an underlying,really important piece.
I think.
Other than that is not all,but most of these co-working spaces
and flexible workspaces, they're likevery purposefully built for work.

(06:36):
So they tend to be really thoughtful workenvironments
that are built and amenitiesbetter than the average office.
So, you know, coffee, tea,
events, different types of workspaces.
I think these often are nicer workspacesthan the average workspace.
And then the last thing I'd say isI totally connect with what you're saying,

(06:57):
which is I don't, you know,like, people need different things
and they often need different thingsat different times.
Like some days I need a quiet placeto do a podcast or to work on a deck.
Right.
And then sometimesI'm looking for community.
I'm looking for inspiration.
I want to be around other people.
So the value of a network like that space,or just co-working spaces in general,

(07:21):
as you can get exactlywhat you're looking for typically,
and not like a one sizefits all solution like your home or HQ.
Yeah.
I mean, for me, it's always been helpfulwhen I'm traveling because the hotel room
is not always conduciveto getting work done.
Between, you know,housekeeping banging on the door and,

(07:46):
bad Wi-Fi and, you know, whatever.
Yeah. So that's when I've done it.
As we move more and more to hybrid work
and companies are shrinking
their physical footprint and doing stuff,
and how if I'm the CEO of a company,

(08:08):
you know, the notionof paying for a third space,
if I'm already paying for an office,might be a bit of a tough sell.
What would you tell that CEO? Yeah.
So I think the paradigm of officeis changing in a fundamental way.
Right.
Like one office for everybodyto solve everybody's problems.

(08:30):
I think is the old paradigm.
And I think what we found there wasthose offices were generally
pretty inefficient, generallyunderutilized and expensive to maintain.
I am at the office today.
Like, I love them, like I believein the whole business of selling office.
Right.
So I think what we're seeingand the thesis that I really have

(08:52):
in this spaceis this notion of office as an ecosystem.
And we talked to hundreds
and hundreds and hundreds of companiesthat are thinking about this.
Every company is different,
different employees, differentgeographies, different requirements.
But I think the prevailing trendthat I like I've seen is,
companies are,
changing as leasingdecisions are coming up.

(09:15):
Right? They're thinking about, okay,I have all this space.
Are people coming to the office?How utilized is it?
And they're not abandoning the officefull sale.
They're typically taking less space.
They're reducing theirtheir size of their leased
or owned real estate,and they're making it more efficient.
They're saying,what is the purpose of this space?
This is person of the space togetherto sell, to do R&D.

(09:39):
And let's have fewer square feet,but let's make them better.
So people want to use them.
And then not mandate that peopleare there all the time, every day.
And instead of saying you have,you can work from office
or you can work from home.
We're seeing companiesbecome more inclusive and saying,
we will meet you where you are,what do you need?

(10:00):
And let me help support you with whatyou need.
The value of aa platform like this fast and not to get
salesy here is it's on demand payas you go.
So what companies are doing isthey're not saying here's another office
we're paying for near your house.
They're saying workfrom where you need to get work done.
And I've given you a $500 budgetthat if you want to use it,

(10:22):
you can use any of these spacesand we'll pay for it.
And then it gives companiesthe ability to learn like,
well, what are my employees really? What?
How are they really using space?
And how should this, help me address
my my work space and strategyin the future?
Yeah, and there are timeswhen you need to have a meeting, but,

(10:43):
you know, you don't have a space.
I mean, to pay 100, 150 bucksfor a meeting room
for an hourthat everybody can go to and then leave,
is probably not a bad investment.
And I'd argue. It's in tonight's meetings.
A lot less expensive to have meeting rooms

(11:05):
when you need them than a meetingroom in your, you know, building
that's empty, 90% of that80% of the time or whatever it might be.
So I think people do find that like,
flexible solutionstend to be a lot more cost effective
than owning heating, maintaining space.

(11:25):
That's that's not used. Well.
What are some of thefor people that have never,
you know, taken advantageof these kinds of situations before?
What are some of the ways people use them?
Like why would somebody use a space when,
you know, they have a home office?

(11:47):
So I mean, post through Covid likesome of the, the big trends we've seen.
So sales teams, right.
Like bigger companiesthat have sales offices.
So have like tensor hundreds of sales offices
that were never that utilized,we're finding them divesting themselves
from those spaces and saying, look,

(12:08):
instead of having this officethat's kind of far away from where
you actually live,
we're getting rid of it,but we're going to give you access
to desksand meeting rooms and offices as you need.
So we see a lot of meetings, right?
Like sales meetings, regional meetings,quarterly meetings, client meetings
where people are leveraging thethe network on demand for that.

(12:29):
And I think another big pieces,I think Covid helped companies realize
that being co-located to where the office
and HQ isisn't as necessary as they thought.
So they might have had employeesthat moved away from Chicago or whatever
city are in and now live in Denveror Vegas or wherever it might be,

(12:51):
and want to offer something to themrather than saying sayonara, right.
Or they're looking for talentand they're instead of just casting a net
that's around their geography,they're saying, let's just
find great peopleirrespective of where they live,
and then let's support themwith what they need.
And that's where we see a lot of use with,I think these flexible workspaces

(13:13):
and networks like ours.
As CEO, what's the
you know, where are your
CEO hat for the momentand rejoined the patriarchy.
And I'm in,
What is the discussion
that you would havewith your fellow fellow CEOs?

(13:36):
What are the 2 or 3 thingsthat they really need to think about
in terms of their offices, in termsof flexible spaces like desk space?
Yeah.
I mean, I think like the, you know,there is a huge cost savings
advantage to leveraging networks like thisand taking less
fixed real estate and being more flexible.

(13:58):
I think like that's a big piece.
I think the other advantages to,
to remote work is, is right, is talent,
both acquiring new talentbut also retaining great talent.
So like and this is, I think a, you know,
that'swhat these tools are really great at.
The last thing I'd say is, you know,

(14:21):
some of the pushbackyou get, in selling what, what we sell
and talking to folks is they believethe best work gets done in the office.
They believe in, like, the watercooler.
And getting people aroundthe table is like,
how great work is done. And
I I'm
very much an advocate of in-person workand getting people together.

(14:45):
I think that is work.
Great work gets done, but I don't thinkit gets done there all the time.
And I think that, like companiesthat have been really successful
at remote work,like Nvidia, right, like the fastest
growing American company right now,like Atlassian, I mean, there's a million

(15:05):
really strong examples of fully remotecompany are very hybrid companies.
It's not about workspace,it's about culture.
And it's about the having the right tools
and the right processes in place
as an organization,
to like, effectively communicate.
And I think those companiesare really great because they have

(15:28):
the best co-working spacesor the best real estate strategy.
It's that they've recognizedwhat's happening in our labor markets
and with like the future of the worldand where things are trending
and they're building the right tools,the right culture,
the right processesin-house to get the best result.
And that's

(15:48):
why those companies are thriving,not because of like, the the watercooler.
I'm going to leave
you with one question,and this is just forget
the fact that this is what you dofor a living as a CEO.
When do you decide an in-personmeeting is necessary and when do you not?

(16:09):
It's interesting because I think of itmore as asynchronous meetings
like asynchronous workand synchronous work, right?
What work doesit need to be a meeting at all?
And it's actually betterif it's a host or it's, it's a, you know,
like in the tools and then, okay,which meetings should be synchronous.

(16:30):
Right.
And I think okay, out of those meetings,which ones?
Should be in person.
And I think when there's,
a huge amount of work to get through,
like it's a big meaty problem.
I think that's when getting togetherreally, really helps.

(16:51):
And I think culturally,like when you feel like
the culture you're building is struggling,
like the, the and good pepor kind of shot in the arm is
let's get people together and remember,like we're humans,
like we're not just these little peoplein these boxes and like,

(17:12):
it's the little things outside ofjust the work of just like learning
about your people you work with, buildingempathy around them.
So I think, like, that'sthe kind of the framework that I like
to use is like,does this have to be a meeting at all?
And if it's a meeting,
are we going to get a lot more squeezedby by doing it in person?
Digging it.
Thank you much. Sam Rosen desk pass.

(17:33):
We will have links to salmon desk pass
and all of that good stuff in our,show notes.
I am going to remove Sam from the meeting
for just a moment while I talk to you.
And I remind youthat if you enjoyed the show,
if you continue to enjoy the show, pleaselike and subscribe.

(17:55):
You know how all this social mediapodcasting stuff works.
I would urge you to check out, Kevinin my new book, The Long Distance Leader.
And I know you're saying
Wayne, the long distanceleader, has been out for six years.
Actually, this is a new, updated edition.
It is the long distance leader.

(18:15):
Revised rules for remarkableremote and hybrid leadership.
We urge you to check that out.
And you can, of course, get show notes,
transcripts, past episodes,all that good stuff.
Check out long distance work life.com.

(18:35):
If you have ideas for
shows, if you have, questions,comments, complaints,
vicious personal attacks,you can find Marissa Renee on LinkedIn
or our email,which is here on the screen below my face.
For those of you enduring that,

(18:57):
that's it.
It's, been another episode.
Thank you so much for joining uson the long distance work life.
Marissa will be backnext week, and don't let the weasels
get you down. Hey.

(19:21):
You know.
Advertise With Us

Popular Podcasts

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.