How Sam Rosen Revolutionized Coworking: From DeskTime to Deskpass - ep. 098

In this episode of the Remotely One podcast, co-hosts Rick Haney and Kaleem Clarkson sit down with Chicago-based entrepreneur Sam Rosen, co-founder of Deskpass, to explore his unconventional path to success and the future of coworking and flexible workspaces. Sam’s journey, full of twists and surprises, exemplifies resilience, innovation, and a sharp instinct for recognizing the shifting needs of the modern workforce.

Sam’s career didn’t follow a traditional route. His unique backstory as a "three-time college dropout" is a label he proudly embraces. Rather than viewing it as a setback, Sam sees it as an essential part of his identity as an entrepreneur. His success story proves that a college degree is not the only path to achievement—what really matters is passion, resilience, and adaptability.

Sam’s first major business venture was One Design Company, a digital design agency he founded from his spare bedroom in 2005. At a time when businesses were just beginning to navigate the digital space, Sam found himself in a unique position—acting as a translator between generations familiar with the internet and those who were not.

In 2008, Sam’s entrepreneurial instincts led him to co-found Chicago’s first coworking space, The Coop. At the time, the coworking movement was still in its infancy, with only about 300 spaces globally. His inspiration for The Coop came during a visit to Brooklyn, where he struggled to find reliable internet while working remotely from his girlfriend’s cramped apartment. After an unsuccessful attempt to work from a local café, Sam discovered coworking through a space called "The Change You Want to See." He was immediately drawn to the community-driven atmosphere and knew he wanted to bring this model back to Chicago.

As Sam’s career evolved, so did his business interests. By 2010, he had developed proprietary software to manage The Coop’s operations, including billing and scheduling. This software became the foundation for his next company, DeskTime, which he eventually sold. However, DeskTime was just a precursor to what would become his most successful venture to date: Deskpass.

Deskpass, the platform Sam currently helms, is designed to meet the growing demand for flexible workspaces. Remote and hybrid teams can use Deskpass to find coworking spaces across the globe, giving them the flexibility to work from various locations. Unlike traditional coworking companies like WeWork, which tie members to specific locations, Deskpass operates as a marketplace, offering a wide variety of workspaces without owning any real estate.

Today, Deskpass plays a pivotal role in the evolving landscape of remote work. The platform not only connects users with coworking spaces but also provides businesses with a way to offer remote and hybrid work options to their employees. 

Sam’s story is a testament to the power of innovation, resilience, and the ability to forge one’s own path. His ventures—from One Design Company to Deskpass—highlight his forward-thinking approach to business and his deep understanding of the evolving needs of today’s workforce. As the world of work continues to shift, Sam remains at the forefront of the coworking and flexible workspace revolution, offering solutions that cater to both companies and individuals!

Learn more about Sam:

• Sam’s LinkedIn: https://www.linkedin.com/in/sammyrosen/?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app
• Deskpass’s Webpage: https://www.deskpass.com/

Transcript

Sam: 0:35

I was a child actor. Uh, I was, I was the

Kaleem: 0:39

Wait!

Sam: 0:39

spokesboy, spokesboy of, uh, it was a national campaign. Uh, but uh, it was uh, But for like three years I was the national spokesman for Old Country Buffet. Um, so,

Rick: 1:08

can hear the fiddle in the background.

Sam: 1:11

My, um, my, my, my, my, my signature line was um, Imagine this is a drumstick. Uh, and it's don't be chicken to try this chicken Yeah

Kaleem: 1:32

Try this chicken!

Rick: 1:34

And don't forget to put the country crock on your cornbread.

Kaleem: 1:39

this is the best thing I've ever heard!

Rick: 1:47

Welcome back everyone to Remotely One. I am your co host Rick Haney, joined by my esteemed colleague Kaleem Clarkson. How you doing, buddy? Oh, oh,

Kaleem: 1:58

sir.

Rick: 1:59

oh, you're working it today. You're working it today. Gettin up those salutations.

Kaleem: 2:04

an ab boob muscle.

Rick: 2:07

Well, you're normally sweating, but you're sweating more than normal, so I, we gotta get you, check his papers. Get the doctor in here.

Kaleem: 2:13

Shit.

Rick: 2:15

You got a pulse, that's all that matters. Hey, everybody, listeners, viewers, since you know how to find us, do us a huge favor, go to ratethispodcast. com forward slash remotely won. And leave us a review. Not a big deal. We ain't asking for much. Again, ratethispodcast. com forward slash RemotelyOne. If you could do that for us, we would be ever so grateful. Since 2015, RemotelyOne is one of the largest communities of professionals. With over 3, 000 Slack members and 5, 000 email subscribers. Those are big numbers. Five! Five! It's free to join. So go ahead, check it out. Remotely one. com and with that out of the way, now that I finally stumbled through all that nonsense. Colleen, give us a tease or two about today's guest.

Kaleem: 3:06

Oh shit.

Rick: 3:07

off and give us a tease or two. Yeah.

Kaleem: 3:11

Rick. I'm so nervous. I'm pouring sweat here.

Rick: 3:15

Did you wear your maxi armpit pads today?

Kaleem: 3:17

I did wear my maxi armpit pads and the shirt's looking fresh. It's a new Callaway shirt. I'm feeling good about it. But Rick, our guest today, I mean, I know you've seen that Saturday night live skit. Our guest today is originally from Chicago, sir. From Chicago. You remember that skit?

Rick: 3:36

Bill Swerski.

Kaleem: 3:40

it's currently still a resident. Still a resident. Um, listen, this part, our guest is actually extremely proud of this. So people out there, there's hope for you. Our guests, they are an, uh, dose trace son. Bonjour. That was in French for all y'all don't know. He is a three time college dropout, Rick, three times college dropout. He dropped out three

Rick: 4:10

He's gonna make us look good. Stop repping him so

Kaleem: 4:13

I mean, you think so you think he's going to make us look good until you hear some of this shit in 2005, born out of his spare bedroom. They founded. One design company, which is a digital design company that they still run and advise after nearly 20 years.

Rick: 4:29

Wow, that's big. That's huge.

Kaleem: 4:31

In 2008, they opened the first coworking space in Chicago called the coop. So we got to talk about that, which they exited in Seoul 2008. Coworking Rick,

Rick: 4:43

wow. Wow.

Kaleem: 4:45

crazy. Something most people don't know about our guest, Rick, is that they were a child actor and spokesperson for Old Country Buffet. Ricky

Rick: 5:02

Were you on Webster?

Kaleem: 5:03

Schroeder! Unbelievable. Old country buffet. We got to talk about that. Then iN 2010, they turned the software that they used to manage the previous coworking space into their own software company called desk time, which they again, exited and sold. Now we're at the two companies they've exited and

Rick: 5:25

Wow. Okay.

Kaleem: 5:26

Yeah. Yeah. So much for college, bro. So much for college. I mean, three times off all shit. Yeah.

Rick: 5:31

needs you?

Kaleem: 5:32

Um, our guest today is the co founder and CEO of DeskPass, which provides remote and hybrid teams an opportunity to find additional meeting spaces around the world.

Rick: 5:48

Hmm.

Kaleem: 5:49

Mm hmm. Mm hmm. Listeners and viewers, please give a warm welcome to Sam

Rick: 5:59

Oh, yeah.

Kaleem: 6:03

Roses!

Rick: 6:10

All right,

Sam: 6:10

Wow. Wow. Wow.

Rick: 6:15

earlier

Sam: 6:17

That was, that was really something. Wow.

Rick: 6:20

Coach had to throw him an extra towel.

Kaleem: 6:22

Coach, get me in the game, coach, get me in the game!

Rick: 6:26

Look at this guy

Sam: 6:27

always wanted an intro like that. That's amazing. Thank you.

Kaleem: 6:31

Oh, bro, thank, thank, you, bro. Thank you Thank you for being here, man.

Rick: 6:37

yeah, no

Sam: 6:38

I'm so stoked to be here. Thank you.

Rick: 6:41

Yeah, so I mean You've got a lot going on. You're a busy guy. You've done a lot of stuff. And yeah, I mean, especially in this business, I mean, going back to 2005, you know, I want to talk about the evolution of desk pass and all that, but way back in 2005, like, Where was it that you saw this opportunity for a company like this? And what was it like kind of navigating those waters with all of the chaos that was surrounding places like, well, especially we work.

Sam: 7:13

Yeah, I mean, man, it's a long story. How, how much time do we have Rick?

Kaleem: 7:20

have plenty of time, man. That's what we hear for you, baby. We here for

Rick: 7:23

brother. That's why we're

Sam: 7:25

No, man. I mean, I think it's all been really intuitive and sort of my little career and path just to kind of observe and, see what seems like an obvious massive opportunity. It just has taken a lot longer than, uh, to get, to get here than, than anyone could have possibly expected. So I don't know, in 2005, I opened an agency, which was, you know, like a design firm, and I did that like just out of my house. Because that's what I was, you know, like I, I grew up in this place where like everyone younger than me grew up with the internet and a phone and like, and everyone older than me didn't. And I think like my first job was, has always been like a translator between people who grew up like in a digital world and those who didn't, and that has sort of evolved to the office and the workspace. I think is a very intuitive, like, makes sense organic path, but it's just a 20 year path.

Rick: 8:28

Hmm.

Kaleem: 8:29

Interesting. So we need to talk about this. We talked about it a little bit in the pre show and I asked you. You know, where you went to school and you're like, I'm a three time called the dropout. I was like, is it okay if we say it? He's like, yeah, I'm proud of that. Like, so for all the people who have had roadblocks in their way, right. Society has talked about pushing, you must go to college to be successful for a long time. Can you just talk about. You know, first, what was your first dropout? Like, and then what was your second one? Like, and then what was your third one? Like, and then how did you come back from that? So would you mind just kind of

Sam: 9:04

Yeah, of course, man. Yeah, I love, talking about this stuff. I mean, it's a little hyperbolic and dramatic, like the three dropouts, but you know, like to me, I've been making shit, for my whole life. I've been entrepreneurial my whole life. I've been building things, selling things, you know, trying to hustle, like, really since I was a little kid, and I think that's just a byproduct of who I am and where I'm from, and again, like, The opportunities that I've been fortunate enough to have. But I've always been a real shitty student. Like real bad. Um, I,

Kaleem: 9:39

I can trust us, bro. Ricky and I, I don't think we were on the honor roll back in school.

Rick: 9:44

Never.

Sam: 9:46

know, I like to learn. There's nothing more that I love learning, but it's just like how you learn, you know? I had work and jobs all through high school and out of high school. And I did what, you know, I thought I was supposed to do, which was go to school. I wanted to go to art school. I really wanted to be in advertising. And I wanted to go to what was one of the best art schools in the country, which was an art center, a college of design in Pasadena, California. But my grades were real bad. So I like, I applied. That's it. And uh, I got handed a rejection letter because I feel like I put on a good show. And they were like, dude come back. Like, prove you can get some good grades. And then once you prove you can get some good grades, come back and try it again. So I went to school in Chicago to try to do that. And that ultimately got me to go to Art Center. But when I got there, I just, for me personally, Sam, like, I've made money learning things like most of my adult life and before that. So this like paradigm of having to go to school. To spend a lot of money to learn versus like just being in the trenches and trying to like figure stuff out, like just made more sense for me and was always intuitive. And I'm fortunate enough, like my parents were like, you don't have to go. Like you have to be happy. That's all that matters. And it's, there's no nice Jewish boy. Like, you know, it's not like you don't have to be a lawyer and a doctor. They're like, just don't be a lawyer, doctor, like be happy. And, uh, so I've had. A lot of privilege to be able to do that. But college wasn't like art school wasn't for me. And I dropped out and started one design, which is this agency. And then I tried again to like go into photography. Cause I'm like, well, maybe I need to learn a craft, like a trade craft. And a school's a really good place to do that. And it was like real quick that I was like, no, I'm just going to keep doing this. And I feel like I've been in college for 20 years. I just feel like I just keep going. I just feel like every business endeavor, every kind of next stage is like a new lesson of learning. New shit.

Rick: 11:52

Yeah, exactly. I feel like that's kind of how the creative mind works, right? You're always looking, I wouldn't call it shiny object syndrome, but you're always looking for different ways to do the stuff that people are already doing.

Sam: 12:05

Yeah.

Kaleem: 12:05

Mm. Mm. Mm.

Sam: 12:07

Yeah. Everyone's different. Like, no shit. It's funny. I got two little kids. I'm like, I hope you don't go to college. I hope you don't go to college, you know? And it's like such a funny paradigm compared to like, I think the generation before us, I'm like, I hope you get real good at chat GPT and like love online learning, but I don't know if I a 50, 000 a year education, like, I don't know, man.

Kaleem: 12:27

Yeah. Yeah. I mean, I'm a huge supporter of higher ed. I believe that, if you have the ability to go to college, you should, if it's affordable. I feel like what you learn, in my opinion, at college is not necessarily the coursework, you know, outside of doctors and lawyers and things that, you know, you need to, you know,

Sam: 12:43

sure.

Kaleem: 12:45

Especially if you're from a small town, like where Rick and I are from, like, you're from Chicago, bro. You're right there in one of the meccas of culture. If you haven't been around culture, like where we're from in Maine and you haven't experienced these things, basically college is like figuring out how to live. So I'm a huge proponent. We're not saying don't go to college, but we are here to kind of hype up. If you don't, there are plenty of opportunities out there for you. It's not the end of the world. pick your path

Rick: 13:11

yeah. yeah. So, I mean, you're talking about co working before anybody knew about co working. So, how did you learn about the concept that, you know, the coop and all that?

Sam: 13:21

yeah, man So I have had this agency and when we were starting the agency We've always been really remote because we could right and I had a girlfriend the Chicago. She moved to Brooklyn I was going to Brooklyn every few weeks and I was trying to run this little agency out of her agency Very shitty apartment. She was super cool, but her apartment was not, it had like a thin line of clothing. She's like all over the ground. She had roommates who were lovely, but it was a garden apartment with very bad internet and very bad cell service, and she would go to school, go to work, and I would try to like run my little business. Out of her apartment and we had our biggest client of all time and like in hindsight, you know We've had bigger now, but like it was a big deal. And I was leading the kickoff call and I dropped the call like five times and my colleague Mr. Noah was like, bro can't do that. You gotta get your shit together. And I was like, okay, okay, I'm gonna, I'm gonna get my stuff together. So I went to, what I think any reliable, like, you know, millennial hipster would do. So I went to the cafe down the street. And the cafe was called the Rabbit Hole. And it was this awesome, great name. The story, the names in these stories, I think is my favorite part. So I went down the Rabbit Hole, and I started working at this cafe, which had Not much better internet and not much better cell coverage and it was very clear very early on they didn't like bought me there Because I would sit there all day with my laptop drink two coffees one bagel So it was like, uh, you know, you can't use your laptop during lunch and then it was like Yeah, then it was like the power stopped working and then like poof the internet was gone. I'm like guys I get the message. I'm out of here. And Noah was like, yo, have you ever heard of coworking? And I said what I think anybody at that time would have said, which is, and still some do, which is co what? And he pointed me to a wiki, the coworking wiki, which still exists. And, it was a list of coworking spaces and there were about 300 in the whole world. And one of course was in Brooklyn. Cause And, that place was called the change you want to see, which when I heard that, I was like, that's a weird name. And it was like a gallery nonprofit. And I was like,

Kaleem: 15:46

okay, definitely definitely some hippie shit. I get that

Sam: 15:49

there's some hippie shit for sure. And I showed up one day, uncomfortable, like what am I doing? Where is it? And I walked in this place and the guy was like, Hey, You're here for co working. And I was like, it's like, welcome. And there was a bunch of cool people around a table and he's like, we got a few rules, be respectful, don't clog up our bandwidth, downloading any porn or like, you know, videos and shit. And I was like, okay, I can, I can do that. And, if you have a good time, there's a little donation box at the end and just like throw some money in the donation box. And I was like, cool.

Kaleem: 16:23

bro. It was free

Sam: 16:24

Yeah, man donation based and

Kaleem: 16:26

shit.

Sam: 16:27

Showed up and it solved my internet problem Solves my phone problem, but the thing it did which I thought was like amazing was it connected me with all these really rad New Yorkers I was used to my girlfriend and her crew and they but it was like people in media and people in design and people in politics and the guy next to me was like in media he worked or I forget what, like current or something like that. And he was like, yo, there's this big musical festival, CMJ, CMJ, in town this week, and he made a list of like all the shows that he could get me on the list for. And I was like, dude, coworking is amazing. Yeah, like day one, you know what I mean? And I was like, this is so cool. Who's doing this in Chicago? And the answer was nobody in the wiki. There was like, uh, a bunch of people who wanted to, and they're actually really cool people that wanted to, but no one had the venue. So my partner, Pat and I kind of right place. Right time had some extra space. And we turn a space next to our office into the first coworking space in Chicago. And like from then

Kaleem: 17:35

Unbelievable,

Rick: 17:36

Wow. Good for you, man.

Kaleem: 17:39

man. Good for you.

Sam: 17:40

right place, right time.

Rick: 17:41

Yeah.

Kaleem: 17:42

viewers Listeners, do you hear what we're talking about? Ready? He opened the first co working space in Chicago. I mean that, I mean, I would just end it right there.

Sam: 17:53

Thank you. This has been a great podcast. I have a great. Have a great night.

Rick: 17:57

You're like the Al Capone of co working spaces.

Kaleem: 18:03

Oh, Al Capone's from Chicago,

Sam: 18:05

that's a good reference.

Kaleem: 18:07

Rick. That's why I am not as funny as you

Rick: 18:10

Well, I was going to go with the Bill Swirsky, but nobody knows really who Bill Swirsky is.

Kaleem: 18:18

yes, we do.

Rick: 18:19

there goes my heart. Must have been the sassage.

Kaleem: 18:25

Oh, Sam, one thing we didn't ask you, being from Chicago, can I put mustard or ketchup on my hot?

Sam: 18:32

Bro, you, you do you. I'm not, uh, uh,

Kaleem: 18:35

No, No, If I, we're coming out to see you. we're coming out to see you. We're in public, right? And all, all this people around, you know what I'm saying? All your homeboys from back in the day, I get a hot dog and I reach for the mustard or the ketchup. Are you nudging me a little? Are you nudging me? Like,

Sam: 18:50

Look nah, man, you do you I would judge you but I wouldn't call you out on it You know what I mean? Like I'm not gonna cancel you for a little mustard My seven year old son loves ketchup like who

Kaleem: 19:02

Okay.

Rick: 19:03

what about, what about high end relish?

Sam: 19:07

Okay. Well now I have an opinion

Rick: 19:09

Okay. Like, it's so fancy. You gotta call it

Sam: 19:15

I think you have a brand idea there

Kaleem: 19:17

That is fancy. So so you build this coworking spot, bro. You're crushing it. You're also running your digital agency. You know, building apps, I'm assuming websites, different things for people, digital marketing. I think a lot of people who are on the show, we love bringing on the show, like yourself that talk about businesses that they sold. Because again, we're trying to tell the stories of remote work. And so many times people like, ah, in order for you to sell your business, you need to have a traditional type business. Right. So what was it like? To sell a business that was basically built around remote work. Like what, how did that come about?

Sam: 20:00

it was weird, man. I mean, so like a coworking business is a really interesting business to buy or sell, right? Like I remember, so we got the coworking space got bought by a company out of Santa Cruz, California called next space. And next space was one of like the OG coworking brands. And we became really friendly with them. And, The guy who's founder and CEO at the time, Jeremy Neuner, they wanted to expand outside of California and just kind of right place, right time we got connected. And it took a while and this was like, so early when they're only like, you know, a few thousand coworking spaces. And but I like remember the day that Pat and I were in California. I hope Jeremy, I hope you're listening to this, but if you listen to this, you know, I love you, bro. But it was like, you know, we did. Mr. Jerry, um, when we like knew they were going to buy it, they agreed to the deal. We were in California and we went back to our hotel and we were like, what the fuck just happened? Like, we're like thinking about what, like we have a lease, we have a list of people. Like a community we built and like someone just paid us hundreds of thousands, you know, agreed to pay us hundreds of thousands of dollars for this business. And it was just like such a, like a wild thing because at the end of the day, like, you know, these are, you can get a lease, you know, you can like, so like it felt like we built something really special and it felt like Really amazing that somebody else would come in and ascribe so much value to a community, that we built. So I, we were, we were just like, did we just like pull one? Like we couldn't believe that this happened when it actually happened. So, uh, it felt, felt good.

Rick: 21:53

Yeah. Yeah,

Kaleem: 21:55

man.

Rick: 21:56

yeah. No. So, I mean, let's forward the button a little bit here to 2010. Okay. And, you know, you created a software for coworking spaces to manage their. To manage their software called, was it desk time?

Sam: 22:09

Yep.

Rick: 22:10

How did you go from a business that was strictly about physical location to creating a software out of that? How did that happen?

22:19

We'll be right back after these words. 2020 was no joke. It changed the game for everyone. Workplace flexibility is no longer a perk, but an expectation. In fact, a recent study showed that a flexible schedule is more important than salary. Yeah, you heard that right? Employees want choices over cash. If you're a startup or a small business that doesn't have a remote work strategy, stop what you're doing right now and complete our free tree assessment at blendmeinc. com. Since 2013, BlendMe Inc. Has been helping small businesses improve the remote employee experience. Let's stay local, but compete global. Visit us at blendmeinc. com. That's blendmeinc. com. Ever wonder how certain ads catch your attention or get stuck in your head? It's because the person voicing it knows how to tell the story. Maybe they're telling you to stumble over to Sullivan St. Patrick's day for green beers, Irish car bombs, and corned beef. Oh. Freakin day. Or maybe Don't miss the deal of a lifetime this President's Day at Callahan Ford. Savings like these should be unconstitutional. Or maybe Come wash away your troubles here at Cooter's Car Wash. We ain't no soap opery, but you'll be singing high praises. Hoo wee, Cooter's! Or Here at Brooks Brothers Mortuary, we put the fun in funeral. Everyone is just dying to join us. Alright, well that's a bit much, but for you, I'll do it. I'm Rick Haney, and if you're a business owner looking for a creative voice in your marketing, look no further. I'll tell your story the way you want it told. Follow along at Remotely We Are One, or visit my website at rickhaney. me for more information. And now, back to the show.

Sam: 24:26

I mean, like I said, for me, my story is very organic and intuitive. You know, like I built software for people, that's what the agency did. We did design and brand and built technology. And that's like my background. My background is the intersection of like design. And technology and that's my lens. And it's funny now. Cause in coworking and it's a bunch of real estate bros, a lot of real estate pros, a lot of finance pros. Like, you know what I mean? I'm not like, I'm not that guy. I'm a designer kid. And, I like to think about humans and like their experiences. And so I sort of through opening the coop. Back to my ass into commercial real estate in the office. And I think I just have a different lens than a lot of other people where I was like, this doesn't make a lot of sense. Like you have these huge assets, like one of the biggest asset classes in the world. And most of the time it's empty, like even in the heyday of office pre COVID, people are not in their seats all day long. And people are not at the office at all at night. And it's just like, they're like, our office is very least inefficient. And I was like, I don't know, like, um. I don't think so. So that was like the lens that I always brought. And then we were building our coworking space. So building software to manage it and to do the billing and the scheduling, there wasn't anything that really existed at that time that we were into. So we're like, let's build it for ourselves. And then when we built it for ourselves, it was like, Huh, like, can we sell this to other people when other people buy this? And then it was like, can we offer this to other people who just have space and allow them to share? Their space similarly to a corporate space. And we were way, way, way, way early. And that's one of my favorite business lessons is like timing, like that business wouldn't know might work now, but like, it wasn't going to work then. They're just, we're enough customers. All the customers were too frugal and everything they wanted was too complicated, you know what I mean? But like, it's part of the journey of learning this stuff and working through it. So for me, it was just solving a problem we had in a space that seemed like an obvious opportunity.

Rick: 26:39

You realized you could scale it.

Sam: 26:41

we

Kaleem: 26:41

yeah, yeah, I thought we thought that could, but what I love about the story and if you're out there and you're building software and tech, it's similar to the Slack story, right? Slack started from a game developer company and they needed to communicate internally. You know, they made video games. Right. And they were like, Oh, we need to create this thing. That's a little bit cleaner. And then boom, it's slack. Right. So, your story didn't end like slacks by any means, but

Rick: 27:06

Right.

Kaleem: 27:07

yet. But then, so then how did you progress to selling that business again? So they sold

Sam: 27:11

Yeah. I mean, yeah, that business was, Basically, in that business, we talked to hundreds and hundreds and hundreds of spaces and selling the co working software was real hard, for lots of reasons that we learned, but in that process, we learned so much like what people want where there is an opportunity. The thing we learned was people don't need the software to run the space. They need butts in seats. Especially like, when I opened the coop, there were 300 spaces. Now there's 40, 000. Like, it is much, much more competitive. So what people need help with is, How do I fill up this space? And we started to really hear that over and over again, which is like, I don't need to help me do the billing, but if you can help me to find some people to bill, like then we got ourselves a business. And so we started to build around that idea and we were inspired by class pass, which, you know, is like a model in gyms. So we started to mess with desk pass. And that was kind of the initial iterations of desk pass. When we were. Putting DustPass out into the market, it became very clear very quickly that it was a much more marketable, better business for us. And we decided it didn't make sense to do both at the same time. So we ended up finding one of our customers. That was really, that loved what we built and was really interested in what we built and very technical. And worked out a deal where they bought the asset and then were able to kind of grow it and continue to build it for a while. So it wasn't like a crazy outcome through desk time, but it allowed it to live, it allowed us to make a little money, and really fund the DeskPass business, which is, you know, what I'm still focused on today.

Rick: 28:57

Hmm. Wow. So Here we are and looking back, well, actually even back to as far back as 2005 when you started One Design, what was the biggest challenge back then compared to some of the challenges you're experiencing today?

Kaleem: 29:11

Working remotely. That is, you know, like you started that you started working remotely way back in 2005, you know? So like, what were those huge challenges? You kind of, you kind of talked a little bit about it in the pre

Sam: 29:22

Yeah, totally.

Kaleem: 29:23

back then?

Sam: 29:24

I think for us, You know, Remote work has always been, like, really intuitive to us. And I always kind of, like, I think, I kind of conflate, like, remote working and co working and flexible working. So, like, my angle on this is really interesting. Like, when we started the coop and we started co working, People were like, didn't believe in it. It was like too nascent. It was too early. They didn't believe people could work this way at scale effectively. Like I remember trying to sell this past to like a bunch of lawyers before COVID and they're like, no, we can't learn, we can't work this way. Like all our books are in the office and like, this is where people go. And this is where people learn culture and train and apprentice. Right. And then it's like COVID hit. Literally, three, four months later, these companies did not have the technology, did not have the culture, were not ready for success, and they were Kind of like forced under the crucible and like four months later, like, Oh, actually like this works pretty good. And also like, I don't like schlepping an hour every day to go to work. For me, it's been this like really funny thing where at the beginning, it's like, no, this won't work. People have to work in the office. And then during COVID, when we were trying to sell here, we're like, well, why would people work anywhere other than home now? Because like, If I have everything at home, like, why would I, work anywhere else? And I'm like, well, this is often me talking to like very privileged, old rich white men. And it's like, well, let me ask you a little bit about your home officer. And it's like, do you, you know, like have your own private place? Like, yeah, it's in the basement. I'm like, and I got my couch and my TV. I'm like, do you have kids? No, they're all grown and they're out in the door. I'm like, okay, well, like, You have a good setup, but there's an endless amount of people who Have roommates, have kids, have challenges and need other space. So to me, it's been this like interesting trope and narrative that has gone kind of back and forth from like, this is never going to work to like, this is the only way to work. Nothing else is going to work. And I think it's, what's really interesting is like where we're netting out, which makes me really excited, which is like, Kaleem, what's good for you? Rick, what's good for you? What's good for Sam? It's different where we live, what we do, even like my job, it's like some days coming to this office and working from here is great some days working from where I live nearby is way easier and better and more convenient. It might be based on like traffic or kids or like my mood or like, do I need to focus? So I think we're moving to this world where. You get to choose, like you get to choose what works best for you, and it's understood that what works best for you isn't gonna work best for everybody else. And people are recognizing this and companies are recognizing like we need to support our people and trust them. So I don't know. That's a little bit about the story about remote, which I think has been so fascinating in my journey.

Rick: 32:20

Yeah. That, that, that's great. That's great. Since we're on the subject and you mentioned earlier, uh, we talked a little bit about offices being the least used asset that you can purchase, and that was even before the pandemic. How does DeskPass help alleviate those costs?

Sam: 32:36

Yeah, so DustPass is a really cool solution. And I think, again, like you talk about the evolution of this stuff, right? It's the office, and then it's co working. V1 of co working are leases, right? You go to a landlord, and you say, I'm gonna take your space, and I'm gonna sign a lease, and I'm gonna do arbitrage. I can, I bet I can, if you're charging me 20 bucks a square feet, right? I bet I can charge 40. I build this community and do something cool. And at the beginning of co working like that is the only deal that you could make because landlords weren't gonna like they didn't believe in the model. They're too busy getting rich the old fashioned way. Right? And then over time, before COVID, but this gets super accelerated during COVID because you see some really stellar examples like we work in a Teide, Industrious, Regis, IWG, landlords recognize, okay, having coworking, having flexibility as part of my building, as part of my portfolio is actually really important to support my building and the future of work. So they start doing these management agreements, right? They start saying, look, come in, I'll cover some of the CapEx, like the front stuff. And then, you know, you won't have a traditional lease and then we can share in the upside and we can do this collaborative. And now you're seeing real estate companies like Tishman, Spire and others, Heinz, that are just saying, screw it. Like we're actually going to build our own brand and our own coworking and our, like our own flexible workspace.

Kaleem: 34:08

Oh, wow. Wow. So you're saying some commercial realtors

Sam: 34:12

because

Kaleem: 34:14

working because they're like, shit, what are we going to do?

Sam: 34:17

like a tenant, like Facebook is coming in and saying we used to take 50, 000 square feet. We're going to take 30, but some days we need 50 and we want to be in buildings that can kind of support us for that. Right. Or I have empty space. There's all this empty office space on the market and there's going to be more and more. It's harder than ever to sell a five year lease, a lot easier to sell. A day, a week, a month, a year. So offering that flexibility is like a fundamental part of, I think, how office and the office industry is thinking about workspace. So the point being with DeskPass, we are a marketplace. We connect all of the different coworking spaces where we don't own any of the spaces or operate any of the spaces. We partner with them. So instead of like a traditional, like I go to WeWork and I just use WeWork, and I have a membership of WeWork. We offer you access to thousands and thousands of workspaces for as little or as much time as you want, which is like a different paradigm of using this type of space, right?

Kaleem: 35:16

I just pay a membership to desk pass and then it allows me to go into WeWork? Or another spot or

Sam: 35:21

yeah, so it depends. We have like kind of two products. One is just for individuals. So I'm in New York and I'm in, you know, Flatiron and I need a meeting on Thursday for eight people. I can just go on there. I can book it. I can find it. I can do it all through the platform pay as you go, but more and more what we sell and where we think a huge opportunities are companies, right? Companies that have all of a sudden have remote employees, all of a sudden have hybrid work policies. And they're taking less office because their office is empty, but they want to offer something more than just the home. So they can offer a, like, You know, branded solution of desk pass. So like good, our X is a customer or like synchrony financial. So synchrony has a synchrony branded desk pass, and then their employees get access to it. And then they can use all of our plat, our platform and spaces, but the boss pays for it. And then the boss can look and see like. Who used it, where they use it, when they used it

Kaleem: 36:18

How often

Sam: 36:20

yeah, set rules.

Kaleem: 36:21

it down, set rules. Damn. That's crazy. That's crazy. I, so I wanted to ask you a question about commercial real estate. We were talking about that a little bit and how it's changing. You know, we're seeing a lot of return to offices by companies. And what do you think is going to happen to organizations that are kind of not coming in line with this new way of workplace flexibility, like basically saying, no, we're going to make sure everybody comes back to the spot. If you were working remotely, you got two weeks to move, to come to the office five days a week. Do you feel like workplace flexibility? Is going to stay and what's going to happen to organizations that don't provide that type of flexibility.

Sam: 37:06

They're gonna lose. Um, I, I, I,

Rick: 37:10

Hmm.

Kaleem: 37:11

They just got to lose. They're just going

Sam: 37:13

They're going to lose No man. I mean, okay. I think. Two theories. One is the office ain't going anywhere. Like, I don't believe like, there's no more office. I don't believe companies shouldn't have offices. And when I say office, I mean like HQ. What I think our thesis is, office is an ecosystem. HQ, it's going to get smaller. It's going to be,

Kaleem: 37:36

Hmm.

Sam: 37:37

Why do we have this space downtown that people schlep to? Is it for us to meet? Is it us for a pitch? Is it for us to innovate, inspire, whatever it might be? And the spaces are going to get better. They're going to get more specialized, but they're going to be smaller. And they're going to be more flexible. And employees are going to have more autonomy to work from wherever they get to. Work done that might be at home that might be on desk pass that might be at a cafe That might be at a co working space near their house or near the office near their kids child's care so office is going to evolve from like one to many it was easy in the old days because Everyone came to the office and that's where we trained and fed and that you know to like Everyone gets their own flavor so I think generally speaking That is what's going to happen long term. I think in terms of the companies that say, No, screw that. You're all coming to the office. Five days a week. Forever and ever. Amen. Again, I'm a designer. I'm thinking about the humans. It's like, okay, if I have a job opportunity between two companies, and one says, Bro, get your ass in the office every day. Same pedigree, same salary, same everything. Another one says,

Kaleem: 38:50

a little less.

Sam: 38:52

Totally. That is, I've read that. I've read that. No, but you know, and the other says, I don't care where you work. Sometimes you have to come into the office because we need you here. I don't know anybody who's like, no, I don't think anyone's saying I've never come to the office again. They're saying like, I don't want to come to the office when it doesn't make any sense for me to come to the office. Right? Like, I don't know.

Kaleem: 39:09

just gonna sit there.

Sam: 39:10

so I think that's what's going to happen in the most talented people.

Kaleem: 39:17

Um, yeah, yeah, I got him, yeah.

Rick: 39:20

I was I was told that I could listen to the radio at a reasonable volume, but it

Kaleem: 39:26

It's office space, folks, if you don't know what we're talking about. We're not being, we're not being rude. We're not making fun of anyone. It's office space, the show. Look it up,

Sam: 39:33

Look it up.

Rick: 39:34

red swingline stapler

Kaleem: 39:36

plain and simple. I mean, it's plain

Sam: 39:40

No, that's a Agripo. That's beautiful. I love that reference. Um, no, man. Yeah. I just think like you're going to pick the company that cares more about you, gives you more flexibility. I think there's ample evidence of that. And I think if you're a company, you want to hire the most talented, best people, you're going to work at the companies that offer remote work. So like.

Kaleem: 40:02

Plain and simple. Plain

Sam: 40:04

And, then there's like the argument that like, well, you can't, I'm like, there are so many examples, like the fastest growing, biggest, hottest company in the world right now, NVIDIA, very remote. At least like, there are so many good examples of like the idea that you can't do it is complete bullshit. It's, it just requires work and thoughtfulness and it's hard and it doesn't, it's, it's, Yeah. Leadership. That's

Kaleem: 40:33

Who would have thought? Who would have thought? Thank you, Rick. Awareness is, huh. Who would have thought? Just a little bit of

Rick: 40:40

we gotta freeze it up

Kaleem: 40:41

maybe a little feedback from the employees. maybe maybe ask the employees a little bit.

Rick: 40:47

Yeah.

Sam: 40:48

listen.

Rick: 40:50

So, Sam, Sam, Jesus, listen to me, I lost my place. I think it Was the, uh, office reference that totally threw me for a loop.

Sam: 41:00

I don't do that.

Kaleem: 41:01

on. Did they ever make a sequel to that?

Sam: 41:03

No.

Rick: 41:03

they did.

Kaleem: 41:04

Good. Good. for them. Like, uh, I think

Sam: 41:07

a remote, uh, set

Kaleem: 41:09

Bro, shh! Stella, cut this out! We're gonna make it Sam, we're gonna make the remote version of

Rick: 41:17

Yes, we are.

Sam: 41:19

Two.

Rick: 41:22

I was, I was told that I didn't have to be on camera for this video meeting.

Kaleem: 41:29

Hey, yeah, I'm gonna need you to commute to The Office. That's four hours in traffic. Cause I need a cup of coffee. Okay.

Rick: 41:42

share with us a comical moment that you may have had while working remotely.

Sam: 41:47

So, This was in, like, the heart of COVID. And it's also funny because I'm, like, having all these, Conversations with people that are like, why wouldn't you work remotely from your home for the future forever and ever and ever? And this, and I remember in a meeting that this happened. And, uh, it was like the most perfect example. You know, I live in, um, In the suburbs. I have, you know, a little too flat. I got a nice little setup. You know, we're lucky. I got a basement setup. My wife works at home like I work at home. Got two little kids above. Got a nice little setup.

Kaleem: 42:23

Okay.

Sam: 42:25

Close the door. Lock the door. I thought about like installing like a little red light. Like don't come in here when the red light's on, but haven't done that.

Kaleem: 42:31

I've heard. That's great.

Sam: 42:32

It's a good idea. So, but, but just lock in the door. So like, I'm like, I'm, I'm, I can survive. Sometimes I can hear like the pitter patter above me, right? My damn kids. That was a few years ago. So they were like, I don't know three and six or three and five. They figured out they figured out a hack. And this was the hack. Which was, they could communicate with me even though I was in another room and they figured out the hack and it was through the HVAC vents, so they would start They would be like Yeah, one day i'm like on a call

Rick: 43:12

heh

Sam: 43:13

it's like

Rick: 43:13

heh

Kaleem: 43:14

of them.

Sam: 43:14

I am proud of him. I got my ass out of that office, but but yeah, it was like And then I would start hearing coins they would like throw coins down the fuck down the Like air conditioning vent to get my attention But it was like, it was like at the park, you know, at the park, how they have those like tubes and you can talk to somebody out like they like, we're like, Ooh, this is like a tube to dad's office. And it was like, it was like an intercom. It was like paging, paging dad. So, That was always, I'm like, so let's talk about your stuff. Come and talk about my setup. My HVAC pipe is plugged right into my kid's room, and they can communicate to me whenever they want, all day long, during all my meetings, even with a locked door.

Rick: 43:58

Oh wow.

Sam: 43:59

a hilarious, um,

Rick: 44:01

I mean, you gotta chalk that up to the brilliance of children, right? I mean, they're not as, they're so smart! And, like, they think in ways that we obviously once did, but we didn't realize it at the time, right? So you gotta embrace that shit. You gotta

Kaleem: 44:14

Yeah.

Rick: 44:15

you

Sam: 44:15

I'm very proud of that. I went back to co working. but, but, went to Death pass found a nice space nearby. But I was like, huh, didn't think of that one.

Rick: 44:31

man,

Kaleem: 44:31

I mean, were the things that they were saying, they weren't like, they weren't saying horrible stuff while you're on calls. Nothing like that. Okay. Okay, cool dad

Sam: 44:39

yet.

Kaleem: 44:40

my pants. You know what I mean? Just saying horrible stuff, you

Sam: 44:43

No, not yet. Not yet.

Kaleem: 44:44

yet. Perfect.

Rick: 44:46

Awesome, awesome. Hey, Sam, where can our listeners find you?

Sam: 44:49

Yeah. So, I'm very accessible on the internet, sam@sammyrosen.com. That's my website. That's my, my personal stuff, Sam, at desk pass, dot com. Uh, you know, I'm on all the internet, but, so yeah, there's another Sam Rosen, he's far more famous than me. He is the broadcaster for the New York Rangers and also like the third tier, for announcer for the Chicago bears. I don't recommend, I don't recommend having a, peer that is a, named as you, that's a broadcaster. Because every time I look myself on the internet, half the people are like, fuck you, Sam Rosen, you're the worst. And the other half

Rick: 45:26

Swerski!

Sam: 45:27

Rosen is a golden God. Uh,

Kaleem: 45:31

biracial golden God.

Rick: 45:35

That's

Sam: 45:35

but, so I'm not that Sam Rosen. I'm the workspace Sam Rosen with, with a, with a child acting credit.

Rick: 45:43

I'm Old Country Buffet Sam

Sam: 45:46

Yeah. That's my hand. OCB Sam, Matt. No, just kidding.

Rick: 45:50

We're done with OCB.

Kaleem: 45:52

Yeah. You know me, you can't help it.

Rick: 45:55

Yeah,

Kaleem: 45:56

Well, Sam, thank you so much for joining us, man. Really appreciate it, bro.

Rick: 45:59

has been a great conversation. Come back anytime. We've had a lot of laughs and we appreciate your sense of humor and certainly tolerating ours. So

Sam: 46:07

No man. this is so fun. You guys are a blast. I appreciate the time.

Kaleem: 46:11

All right, man. We'll talk to you all later, man. Peace.