Podcast: The Best Coworking App to Find Space

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October 21, 2019

Designing and procuring a new way to explore and experience coworking, with Sam Rosen, Co-Founder and CEO of Deskpass

On this episode I’m speaking with Sam Rosen, Co-Founder and CEO of Deskpass - a membership platform that provides access to hundreds of coworking spaces across the country. He also founded One Design Company - a digital branding firm based in Chicago, and opened The Coop, the first coworking space in Chicago.

Formally trained as a designer, Sam now spends more time at the business end of projects. He prides himself on connecting great people with lovely ideas, all with the goal of making meaningful work, and hopefully, making the world a better place along the way.

Podcast Transcript

Chris Arnold: Welcome back to the Transforming Cities Podcast. Each episode highlights ideas around rethinking the way cities are evolving. We discuss planning, design, technology, development, and other fields that contribute to the urban experience.

Sam Rosen: Some people, I think, do a good job of insulating their work from their life, and they kind of have them separate from each other. That's never been the mentality that I've had. I feel like I always have work and life kind of in one giant jar that shakes around together.

Sam Rosen: It was a really fun time, but it never felt like a lot of hard work.

Chris Arnold: On this episode, I'm speaking with Sam Rosen, Co-founder and CEO of Deskpass, a membership platform that provides access to hundreds of coworking spaces across the country. Sam also founded One Design Company, a digital branding firm based in Chicago, and also opened The Coop, the first coworking space in Chicago. Formerly trained as a designer, Sam now spends more time at the business end of projects. He prides himself on connecting great people with lovely ideas, all with a goal of making meaningful work, and hopefully, making the world a better place along the way.

Chris Arnold: A few quick notes before today's episode. If you enjoy the podcast, please share this track and others on your social accounts to people you think would be interested. Also, please rate it on iTunes or other platforms where you listen. This is how we grow and it's much appreciated.

Chris Arnold: This podcast is driven by Authentic Form and Function. We're a design and technology studio working on tools and platforms to improve the urban space. You can find out more online at authenticff.com.

Chris Arnold: And finally, we want to hear from you. Email your feedback and ideas of who else we should speak with to podcast@authenticff.com.

Chris Arnold: I'm your host Chris Arnold. Let's jump in.

Chris Arnold: Sam, thanks so much for joining me today.

Sam Rosen: Thank you, Chris. It's a pleasure.

Chris Arnold: So let's start out with your roots. You are a Chicago guy through and through. Is that right?

Sam Rosen: That is true. I am a born and bred Chicagoan. I lived in LA for about four months. That's the most I could handle not living in Chicago. But I grew up on the North Side of Chicago, and now I live in Oak Park because I'm a grown up with my wife and my children. This is what you do now.

Chris Arnold: And what was your upbringing like in Chicago? What did your parents get into?

Sam Rosen: My mother is a painter. She's a fine artist. She's an incredible fine artist. She's actually, if anyone watches Grace and Frankie, all of Frankie's art is actually my mom's art. So, she is a painter's painter. She's been painting since I was ... For as long as I can remember. That's what she does.

Sam Rosen: And then my dad, growing up, directed television. He was producing, and making television commercials, and pacing up and down our house. Now he does that and also some real estate as well.

Chris Arnold: So you were around creative thinking for your entire life.

Sam Rosen: I really was, and I don't think I really appreciated it until recently, but a lot of the Mid-Century furniture and books on modernism and minimalism are actually books that my mom and dad have had in their house that I grew up with. I just realized that recently and I'm like, "That's cool." I don't think most kids get that.

Chris Arnold: What is the output of a son that has an ad agency father and a painter as a mother, where would you say you got your start as a young entrepreneur?

Sam Rosen: Well, my parents were always very supportive of me. They basically said, "You could be anything you want to be. We don't want you to be a ... We'd prefer if you're not a lawyer or a doctor. There's a lot of those." They always, I think, were open to creativity and just had it around us.

Sam Rosen: I got really interested in the internet and the World Wide Web really, really early on. I actually remember when America Online said, "Coming soon: the World Wide Web," and that was really my first introduction to the web. I remember asking my cousin, "Hey, what is this?" And he trying to explain it to me the best he could.

Sam Rosen: Since that moment, I was always really interested in websites and the whole mechanics around it, and tried to reverse engineer it, and understand how to make it. That gave me opportunities to make projects for my parents and my parents' friends and the friends of friends. At a certain point, I really considered those guys as clients. I think it was like three generations out and that's really the genesis of my experience making stuff on the internet.

Chris Arnold: When you're a kid like that figuring it out, because I was in a similar situation, I think it's funny to look back and ask yourself, does any project specifically stand out in those early days that you're like, "Oh, I made that furniture store website" or the kind of the crazy stuff that you do right out of the gate?

Sam Rosen: I mean, it's funny. I've been going through this purge mode and cleaning through all of these old files and boxes of stuff that I've been ignoring for many years, and a lot of it is just that, and it's stuff like in high school, and it's me pitching Paper Source, which is a big like ... Now, a national brand, but was just a few shops based out of Chicago. And again, it was like, "Mom's friend." I still have the whole original pitch proposal.

Sam Rosen: So, I did their website. That was the answer to one of your questions, but I still have the proposal and a couple other proposals that I made from that time. They were so embarrassing and so cringe-worthy and so, "Ugh!" I remember at one point, I said, "Money, money, money. Who wants to talk about money? No one." That's how I opened the section on how we're going to charge for the project.

Chris Arnold: A little tongue in cheek proposal writing.

Sam Rosen: Yeah. There's a lot of old projects for DJ companies and little stores that I did before I really probably should of.

Chris Arnold: Yeah, that's so good. That's so good. There's a little bit of a gap here. You're cranking on websites, you're a young entrepreneur. You end up starting a business around 2005, but we'll get to that in a second. What happened in that time period where it went from tinkering to this could become a real business for me?

Sam Rosen: You know, it always sort of was a business. At first, a lot of the projects I did were for school or they were for personal projects, but I think as soon as other people got exposed to the fact that I could do them, because there were just so few people who could, it very early became apparent that it was a business too and it was a way to make money and move things forward.

Chris Arnold: Right. And at that time, it was such a specialty too, right? It was a new technology. I would argue that our generation, we didn't grow up with it, but we grew up into it, and then we were at that age where we learned it pretty quickly and we ultimately became the first generation specialists in it.

Sam Rosen: Yeah. That's totally right. Everyone older than me had no fricking idea what this was or how it worked, and everyone younger than me grew up with it. The ability to be able to thread the in between for these two groups is a huge part of my career, what I still think I do, and what is still something that's vital to succeed because it's a big difference. If you grew up with this stuff and you didn't, you can very easily have a different way of experiencing, and looking, and learning through the world.

Chris Arnold: So in 2005, you started a company called One Design Company out of your apartment, which is crazy to say because One Design is a really successful firm out of Chicago that has done incredible work, but how did you get that started? What's the story there?

Sam Rosen: It was very gradual. I think it was really from those types of projects to working for my parents' friends and friends of friends, and then it just started to make sense to have a business entity to do all of this out of because I thought that was the professional thing to do. I had a theater company with my friend Josh called the One Theater Company, and I was doing all the design work for that, so the name came really easily, One Design Company. Very original name.

Sam Rosen: It was really just a shell to allow me to do work. And then what happened really naturally was the demand of that work exceeded the supply, and I was living downtown, and getting connected with really awesome, creative, wonderful people and realized that we could work together and collectively do work together, and make money together. It all happened very, very naturally.

Sam Rosen: Quickly thereafter, I met Pat Griffin, who is one of my partners and is my longest partner.

Chris Arnold: No, that's great. Going from teenager in the bedroom to young adult in the apartment to, I think you had an office in Fulton Market, is that right?

Sam Rosen: Yeah. Right above the Pelican, the most delicious restaurant in Chicago in my humble opinion.

Chris Arnold: What was that time period like? I know what it is like in some senses to have the business getting off the ground, and you're meeting new people, it's an exciting time, and kind of on the cusp of something bigger. Did you feel that all along? Did you feel the snowball effect starting?

Sam Rosen: It was really fun. I always felt like I was in the right place at the right time. Fulton Market was so cool. I was the third tenant in a building that was mostly creative people. A lot of creative opportunities came directly from the building.

Sam Rosen: It's a lot easier in hindsight to look at this and be really romantic about it and being like, "It was the best of times," but it was just some people, I think, do a good job of insulating their work from their life and they have them separate from each other. That's never been the mentality that I've had. I feel like I always have work and life in one giant jar that shakes around together. It felt like that. It was just like I was living and breathing work and this creative environment, hanging out with these awesome people, and it was a really fun time. It was really hard work, but it never felt like a lot of hard work. It always just felt like a cool way to live your life.

Chris Arnold: What I really love about your story, Sam, is that there comes a point right around this time in your history where coworking and the idea of using space surfaces in way that you probably didn't even think about it at the time, but in retrospect, is really intriguing because you had a girlfriend in Brooklyn, you were traveling back and forth around this time; there wasn't really anywhere to work, and so you ended up at a specific café. Is that right?

Sam Rosen: Yeah, exactly. I ended up at this café because I thought it was going to be a better work environment. Basically, my business was growing. I had a conference call in my girlfriend at the time's garden apartment that I dropped five times. That was our biggest client at the agency. One of my business partners now said, "Dude, you've got to do better." So what I knew to be better was this little café across the street in Brooklyn called The Rabbit Hole. It became really clear that they didn't want me there.

Sam Rosen: First of all, the internet wasn't much better, the cell phone connection wasn't much better, and then all of a sudden, there was a table tent that said you couldn't work there during lunch rush and the power stopped working, the internet stopped working. I was like, "Okay. I get the point."

Sam Rosen: A buddy of mine and a colleague, Noel Bernson, said, "Have you ever heard of coworking?" And I had no idea what that was. It was almost nine years ago. There happened to be one of the first 250 or so coworking spaces in the world a couple blocks away. I walked in and there was a bunch of interesting looking people around a big table in an art gallery type of space. A guy looked at me and he said, "Are you here for the coworking?" And I said, "Yes." He said, "Awesome. Welcome. We have a couple of rules: be respectful, don't download any movies or porn, and be a good citizen. At the end of the day, if you like it, put a $20 donation or so in the box."

Sam Rosen: I fell in love. It solved a very pragmatic problem I had around not dropping important phone calls, but it also put me in a new environment with really interesting, like-minded people in a way that was really interesting, and really cool, and nothing I'd ever experienced before.

Chris Arnold: That started something else for you and a new avenue of entrepreneurialism.

Sam Rosen: Yeah. We decided to take that concept and see if anyone was doing it in Chicago, and there wasn't. There were a few people that seemed kind of interested in the concept of coworking in Chicago, and there were people certainly sharing their space in Chicago, but there was no coworking spaces in Chicago. My partner Pat and I decided to take our extra space next to One Design and turn it into the Coop, which was the first coworking space in downtown Chicago.

Chris Arnold: How was that received at the time? Was it you open the doors and everyone flooded in or was it a slow burn where, over time, it gained in popularity?

Sam Rosen: It was a lot different, I feel like an old man when I say this, then than it is now. Right? There were zero coworking spaces and there was a list of people interested in coworking.

Sam Rosen: When we opened, there were people who immediately came that were looking for something like this, and some of those people were really cool people likes Charles Adler, who's the Co-founder of Kickstarter was working out of our space on Kickstarter at the infancy of Kickstarter. Our friend Linus was working on titles for James Bond. There was just this really interesting environment that filled up pretty organically, not super rapidly, but with minimal work at the very beginning, which is a lot different than what it is today.

Chris Arnold: Yeah. So this is actually another pivotal moment for your career in that this idea of using space in a more unique or efficient way really prompted you to start a new endeavor alongside of your other business that was already rolling along, One Design Company. What was this first iteration called and what was the goal?

Sam Rosen: Yeah. Being a guy who's interested in technology and design, as soon as we started operating a coworking space, we became really interested in the tools and technology around it, and just the whole ecosystem of how office space works, and how people use it.

Sam Rosen: The first thing that we did was we started a software ... Well, first thing we really did was we built a directory of coworking spaces called Desktime and it was just a way to find these spaces because at this time, there was a Wiki that had most of the coworking spaces on them, but there wasn't really a directory that showed all of these spaces all over the world that were popping up.

Sam Rosen: We started doing that, and that very quickly pivoted into building software to manage our space, The Coop, but also the day-to-day operations of anybody like us who wanted to take some space and operate a coworking space. We raised the money and we built software to help people solve this problem, and that was a business called Desktime.

Chris Arnold: Desktime was the first app to find coworking spaces, that we're aware of, and it became something that led to, I would say, version 2.0 for lack of a better phrase. What was the transition like from Desktime to what we now know as Deskpass? Are they the same business or are they different businesses entirely?

Sam Rosen: They're different businesses now legally, but they're the same product that has evolved out of Desktime into this Deskpass business. I think it really stems from this idea of when we opened The Coop, there was zero spaces in Chicago and about 250 spaces in the world. Fast-forward today, there are a reported 175, 200 coworking spaces in greater Chicago alone, and close to 30,000 of these flexible work spaces all over the world. It's so unbelievably different, it's hard to fathom unless you have been fortunate enough to watch it firsthand like we have.

Sam Rosen: What we quickly understood, not so quickly, it took a long time to figure it out, but is that the way we can really help and the biggest problem that we see in this space right now is that most people don't know these spaces exist. Most people have never been to one or tried it or knows there's an interesting, creative workspace near their house that might be cool. If we can help find these people, and educate them, and bring them into this ecosystem of all these wonderful, flexible coworking spaces all over the country and ultimately the world, then we can provide a ton of value because for me, it was easy to open my coworking space, but if you open today, there are good competitors, there are interesting spaces. It's a much more competitive world.

Chris Arnold: Yeah and I imagine, even on the technology side of things, I feel like it's easy to gloss over that and when we talk about it, that's a given, right? There's something that's powering this platform on the web, but what was that challenge like, building the actual management software on the backend to power a Deskpass-like platform?

Sam Rosen: You know, a learning experience. I think we can probably both empathize about this given our collective experience and knowing your background. Running a services business is extremely hard. Working for clients is difficult and having to earn every dollar you make one hour at a time is really hard. I always had this fantasy while I was really focused on One Design that building a product and our own app and technology to solve a problem is a much easier thing to do than run a consulting business.

Sam Rosen: And I was wrong. I don't think it's easier, but it's got to be as hard, right? It's different challenges, it's different problems, it's a different domain. I'm fortunate enough to have a lot of experience to help other people build their own products, so mechanically, to get a concept from idea to something on the internet that people can use is something that I have a lot of experience with.

Sam Rosen: The most challenging part, for us, was not that. The challenging part was getting something that people want to pay for and buy and use, and then getting it in front of them, and once they're using it, making sure they know how to use it, and if they want to leave, encouraging them not to, and if they have a problem, understanding how to support them. It's like when you work out a new exercise or a new part of your body and you're like, "Ugh, I didn't even know there were muscles here. I didn't even know this was a thing that I was going to have to worry about."

Sam Rosen: So I don't know if it's easier or harder than a consulting company, but I think the biggest challenges for us has been how do we really spend our money wisely to get to a point where we can know if something's working or get to a place where something is working? That's been a lot of learning.

Chris Arnold: And as a business owner at this point, two individual businesses, one very client services-focused, one product app-focused, how did you find yourself splitting your time, especially at first, between One Design and Deskpass so that you felt like you weren't spreading yourself too thin, or that you were still checking in with your teams, or was that in and of itself a challenge?

Sam Rosen: It is a big challenge. The only reason it's worked for me is because I have the most awesome team of people that I work with, and really great partners in the things that I do, both with Deskpass and One Design. It's been a long, slowish transition. It wasn't like one day, everything's going to change; it's been evolutions of change over time.

Sam Rosen: I'm not actively involved in One Design's day-to-day business. I help however I can, but the business runs and operates and grows and is doing as great as it's doing because of Noah, David, and Pat, my partners there.

Sam Rosen: As someone who's started a business, it's like at the beginning, you want to just keep the fricking roof up and you feel like you're using all your own energy to keep the roof off, and then you meet someone like Pat, my partner, and he helps hold the roof up with me, and it's easier. And then you get some other partners and they're all holding it up and then you get to the point where you can start stepping away and realizing that the further you step away, the higher the roof gets, and the better the company does, and it's finding great partners and building longterm relationships with them.

Chris Arnold: Yeah, that's a great analogy. I think this is something you alluded to earlier, Sam, but you were talking about this, I'm going to date myself here, but this Field of Dreams kind of idea of if you build it, they will come. But I think many of us know if you build something on the web, this app, this great idea, that doesn't necessarily mean people are going to come to it.

Chris Arnold: When it came to Deskpass and building something that people actually want to use, what was that pitch process like or what were those communications like with potential partners because to some degree, I feel like that does, at least in the beginning, feel like client services where you're trying to just sell, sell, sell, but what was that time period like with Deskpass?

Sam Rosen: Yeah. I think what has worked effectively for us is when we built Desktime, when we were trying to build space management software, we over-engineered it. We raised some money. It was a lot of money for us, and we hired amazing engineers, and we tried to build an app that's going to scale that looks and works fricking awesome. But we couldn't move fast enough to get to the point where we had a product that people actually wanted to pay for and buy.

Sam Rosen: When we started to focus on Deskpass, we took a very scrappy approach. We tried to build something that didn't scale that well, that we can change more quickly and we knew at some point we're going to have to totally redo, but we could get there faster, and get feedback faster, and iterate faster, right?

Chris Arnold: Yeah.

Sam Rosen: So it didn't have to be the fanciest, it didn't have to look the best, even though we wanted to look great and work great, you know what I mean? But it had to prove the concept.

Sam Rosen: That was the big change for Deskpass. We knew that getting butts in seats was a good idea, and collectively, this business model, which is we aggregate all of these coworking spaces all over the country and you get one membership that gives you access to all of them. It's often the least expensive option with the most amount of spaces. We knew that was a compelling idea, but we didn't want to spend a lot of money and time to prove it out.

Sam Rosen: That's been the big difference with Deskpass is we've taken a more granular, iterative, experimental approach that allowed us to know this was working at every step of the way before we started to put larger investments into it.

Chris Arnold: Quick tangent. I have to ask, someone that has grown up around designers, around creativity, doing your own projects as a teenager, how hard was it for you to not focus on the creative perfection of Deskpass, letting that go, and focusing on building something that works and that can sell over the pretty picture?

Sam Rosen: Pretty hard, but also, I have an analytical bent. I'm analytical enough to look at quantitative information and I think that was one of the biggest revelations is so much of what we do at Deskpass is quantitative, like what are the results? You can see what works and what doesn't if you're tracking it correctly.

Sam Rosen: One thing that I've learned over and over and over again doing Deskpass is my assumptions are wrong! A lot! Especially when it has to do with communication, and marketing, and advertising. When we run experiments to see what ads are going to work the best, what landing pages are going to work the best, I'm almost always wrong about what performs the best. That's been a soul-searching process because as a designer, especially as a partner in a design firm that does this for a lot of people, you want to think, "I know what's best. My assumptions are best. I have good assumptions."

Sam Rosen: And I think about it. The group of people I surround myself, the feedback loop that I get is not indicative or a good indicator of the type of people who are using my product or just mainstream America, and that's been really humbling. I've had to realize that sometimes the best design is not the prettiest, and sometimes the best design is the bluntest, and sometimes you don't need nuance; you need a fricking hammer. It's been a thing I've grappled with because I want to make something that I'm proud of, that's well-crafted, that is a great experience, but the only way to get there is for people to love it and use it.

Sam Rosen: So, it's this dance and we're still trying to figure it out, but it's been humbling.

Chris Arnold: I bet, yeah. With that in mind, let's pivot back to the real estate side of the equation because that's obviously a huge part of Deskpass. There's a figure that you gave me and I was shocked at this. One of the big players in the CRE industry, JLL, mentioned that we're still at a sub 5% flex office workspace situation, so coworking office centers, amenity incubator type spots, and by 2030, you told me that they expect that to be upwards of 30% in terms of utilization. How does that landscape impact what you're doing with Deskpass and how do you see that landscape growing?

Sam Rosen: Yeah. It's pretty unbelievable to believe. It's easier for me to see because I saw this go from one space in Chicago to almost 200, but this is saying that it's going to be five, six times more. There's going to be 1,000 spaces in the next 10 years.

Sam Rosen: The only way this works is if everyone adopts it: big companies, small companies, freelancers, independent workers. That is going to represent a huge, huge part of the office and a huge part of space. So I fundamentally believe that the way we work is changing and everyone's relationship to the office is changing. It doesn't mean your HQ office is going to go away and you're not going to have to go to that office from time-to-time, but it means that work is going to become an ecosystem of space, and you're going to be able to use space as you need it based on where you are or what you need for that day, what you're doing, and you can use a network of space, both within your company, other companies, coworking spaces, cafés, and I think that's what this represents.

Chris Arnold: Yeah. There's this idea too that space is often thought of as being used from 9:00 to 5:00 or 6:00 to 6:00, but then what happens with that empty real estate from 6:00 PM to 6:00 AM as well? I think that's an interesting aspect of how commercial real estate is evolving too, and probably one of the big shifts among many that you're seeing in the space, that I'm assuming is impacting your business or at least themes that you have in mind as your business evolves and how the real estate world function in general. What do you think about those thoughts?

Sam Rosen: Yeah. Again, I came into this from design and the more that I learned about specifically office space is that it's inefficiently used. Like you said, just the average desk in a business where someone is sitting at their office desk is used three hours a day, butt-in-seat time. So 21 hours of the day, that seat is empty. That is inefficient and that means if you have 100% of your seats full, you're still only using them like 15% of the time. And most people aren't. Most people have a lot of empty space.

Sam Rosen: There's so much inefficiency that's already happening in real estate, and it makes sense if you think about it. Most commercial real estate is driven by brokers and tenant representation, and a tenant rep is incentivized right now for you to sign a big, long lease. The more square feet, the longer the time, the more money they make, and the more money everyone else makes. It's creating huge inefficiencies in the way that we use space and there's economists that say in a city like Chicago, we already have enough office space for the next 20 years if we just actually use our office space better.

Sam Rosen: That's one of the things that's so compelling about the space to me.

Chris Arnold: Yeah, I love that, and I love the fact that you're thinking about space in a non ... Let's see if I can see this well. A non-antiquated way, a way that is not thought of as the old guard way, which is as you said, big contracts, as much square footage as possible. How can we slice that pie in a different way to still make it really efficient, and in many ways, much more flexible for businesses and certainly the evolving workforce?

Sam Rosen: Yeah, I think you're right. I think a lot of traditional real estate solution to this is a big company saying, "We're going to build our own brand of coworking and do this ourself," which doesn't seem like the solution, or "We're going to have little brokers. Instead of focusing on big deals, we're going to focus on little deals."

Sam Rosen: But as you and I know, and to the point of being in the line of the old and the new, that's just not the way that we're going to consume things in the future, especially something as big as our space. I'm not going to consume things five, ten years at a time; I'm going to consume them one hour at a time, one day at a time, one month at a time, as I need it, as it's efficient to me and makes sense for me. The idea that this old way of solving the problem is going to solve this doesn't make sense to me. I think you actually have to think about human beings, and how they work, and how they spend their day, and what motivates them, incentivizes them to get their butt out of their house or out of the office, and that's where there's real opportunity here.

Chris Arnold: Sam, before we start to wrap up, let's tap into a big question in the coworking industry from operators to facilitators like yourself, and that is options are great, amenities are great, but what if you go to an office space and it smells or the internet's really slow? I think that's a really big challenge that you're certainly facing, and I'm curious, how do you manage expectations on that level with a product like Deskpass?

Sam Rosen: Yeah, it's a great question. The thing that's cool about our platform is when people think about coworking, they think about WeWork, they think about Industrious, they think about Regus, and if you look at WeWork and Regus combined, they have about 1,000 spaces in the United States, but there are actually 4,500 other spaces in the United States that are independently owned, regional, that are all in small communities, niche communities, all over the country. That is our bread and butter and the types of environments that power Deskpass.

Sam Rosen: It creates something really cool, kind of like Airbnb, where you can get into really interesting spaces and really interesting communities instantly, but it creates a disparity in quality and expectations. Some of our spaces are un-fricking-believable. They are like Four Seasons. And some of them are sort of chill and hippie and much more laid back.

Sam Rosen: What we believe, as a software solution and the middleman that helps make this all work, is that we're in the hospitality business, we're in the expectations management business. What we're trying to do is let you know what you're going to get, and what we found is location tends to trump anything else. If you have a very specific location you need to be, maybe it's the courthouse, maybe it's near a library or near a meeting, you will often pick a location close to that and be more forgiving on quality, but it's our job to let you know what you're going to get and what you can expect.

Sam Rosen: But then it's customer service. In a product like ours, we have 7:00 AM to 7:00 PM customer service. Basically, you just call us. If you get in and you don't like it, it smells, you can't get in, the internet sucks, it's not what you expected ... I like to use Grub Hub as an example. If you have a bad Grub Hub or Seamless experience, depending on where in the country you are, you don't call the restaurant; you call Grub Hub and you say, "That sucked," and Grub Hub goes, "Well, we're going to call them. We're going to take care of it and we're going to credit your account."

Sam Rosen: We want to provide that so people know they're going to have reasonable expectations of the environments, we're going to make it really easy to get in there and automatically unlock the door through our app, and buy things, but if things suck, you can talk to us and we'll fix it and it's a real human that really cares, you know?

Chris Arnold: Sam, what is next for Deskpass?

Sam Rosen: We're growing and part of that is geographically. We want to be in a lot more cities by the end of the year all over the country. And then a big part of what we're working on is how do we work with large teams, large businesses, and large groups because to JLL's points in the study that they did, if real estate office space is really going to be 5% to 30% for flexible space in the next 10 years, it's all about big teams and big groups adopting it. We're trying to figure out how to help solve that problem for the biggest teams and companies so they can take advantage of little, awesome, indie coworking spaces in rural environments or cool neighborhoods or places that you don't get exposed to most of the time.

Chris Arnold: Right, absolutely. Sam, I really appreciate your time today and I don't want you to run out with answering one of my favorite questions, which is you have so much experience, you have so many great connections and stories with the work that you do, so tell us, tell the listeners who we should be paying attention to, who's doing groundbreaking or inspiring work that you want to point us towards?

Sam Rosen: I'm a Chicago boy, so I tend to like to represent some awesome people that I think are doing really interesting things in Chicago. Two of my hometown heroes are Jim Coudal, who is the founder of Field Notes and has a ton of other really awesome projects, but also his wife, Heidi Coudal, who runs Big Delicious Catering, which is a really cool food company that does catering out here.

Sam Rosen: I'm a dad, I've got two kids at home, so I'm always looking for people who do that work, who can build businesses that are really inspiring on their own terms and live their own life, but also have a beautiful family, wonderful kids, doing it all right. It's not necessarily about being the biggest or the very, very best, but it is kind of about being the best, but also just having a good life and doing it right. Those guys inspire the heck out of me.

Chris Arnold: That's fantastic. South Side and North Side represented, right? Chicago through and through.

Sam Rosen: Yeah, represent.

Chris Arnold: Thank you so much for joining us on the podcast today. Right now, I want to roll out the red carpet for you. Tell the world what you're up to, where we can find you and your businesses online.

Sam Rosen: Yeah. I'm Sam Rosen. I've a little website, SammyRosen.com, which links to all this stuff, but my agency, One Design Company for branding and digital work. And then if you're interested in learning more about coworking or checking out coworking, go to Deskpass.com. We've got a free trial and you can try an awesome coworking space for free.

Chris Arnold: That's fantastic. I can personally attest to Deskpass. This is not a paid advertisement, but the coworking space that I frequent is also a member of Deskpass now, so great platform-

Sam Rosen: Shout out to Furniture Coworking. It's a cool space.

Chris Arnold: Furniture Coworking. HQ, Denver, Colorado.

Sam Rosen: Represent.

Chris Arnold: Sam, thank you so much again. Appreciate your time.

Sam Rosen: Thank you, Chris. Appreciate you and the podcast. Take care, brother.

Chris Arnold: Thanks.

Chris Arnold: Transforming Cities is brought to you by Authentic Form and Function, the digital design and development team that just might be a perfect fit for your next urban project. If you're a new listener, you can follow along at authenticff.com/transformingcities or you can simply subscribe through your favorite apps, including iTunes, Spotify, or Stitcher.

Chris Arnold: Thanks for joining us.

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