Discover how Sam Rosen, co-founder and CEO of DeskPass, turned a pivotal moment in New York into a global movement redefining where and how we work. Sam’s journey from designing in Chicago to building a flexible workspace marketplace will inspire you to rethink traditional office environments.
Learn how his unique blend of creativity and technology insight has driven DeskPass to become a leader in connecting companies with diverse workspace solutions worldwide.
You’ll also learn DeskPass’s strategy for standing out in an increasingly crowded market. From offering a variety of workspace options in both bustling cities and quiet rural areas to adopting a user-focused design and flexible pricing model, DeskPass is revolutionizing the way businesses approach workspaces. Sam shares his business’s hiring practices that ensure cultural fit and reveals the keys to building a great team.
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0:00
This is the Remote Work Life Podcast. Yes, it certainly is, and I'm your host, alex Wilson-Campbell. Thank you so much for joining me. Have you ever found yourself trying to find somewhere to work, somewhere that's comfortable, somewhere you feel you can be at your most productive, and somewhere that's got good Wi-Fi? Well, today's guest, sam Rosen, is co-founder and CEO of a business that has solved that problem on a global scale, and the origin story of the business is something to certainly listen out for, as is the refreshing way in which his team goes about the hiring process. So listen up and enjoy today's episode. Today's episode.
Sam Rosen:
0:44
So I am based out of Chicago and I am the co-founder and CEO of DeskPass, which is a marketplace that helps connect companies and the folks who work at those companies with flexible workspaces all over the world. So that includes desks, meeting rooms and offices all available by the hour, up to month to month to month. I'm based out of Chicago and have a nice little family. I live in a little town called Oak Park.
Sam Rosen:
1:16
I came into this industry as a designer. Before this, I started a design firm called One Design Company here in Chicago that does work all over the world for all sorts of really interesting clients, and so my background has always really been the intersection of design and technology and because of that, I came across co-working really really early on, when there are about 300 spaces in the world that call themselves a co-working space, and my on, when there were about 300 spaces in the world that called themselves a co-working space, and my partner at the agency and I opened the first co-working space in Chicago. So I have a really interesting, I think, perspective and there's probably 30,000 plus workspaces to just this change in how we work and where we work, and I've always really taken it from just a perspective of humans and design and human, just how we work and how we think about living our best life.
Alex:
2:18
Next, can you describe a personal story or experience that has influenced who you are today?
Sam Rosen:
2:24
a personal story or experience that has influenced who you are today. Well, to this question is how I came across co-working and, like I mentioned, I owned an agency or still do and I got to travel a lot. There's probably like less than 10 of us and I was traveling to New York a lot from Chicago and I was living out of when I was there, out of my girlfriend's apartment and she was super cool. She had a horrible. She had a garden apartment with a thin layer of clothing always on the ground and very bad internet and very bad cell phone coverage and we actually had the biggest pitch that we had to date and I was kicking off the engagement and I don't know. I dropped the call like five plus times and my colleague at the time was like dude, you can't do this anymore, you need to get your shit together.
Sam Rosen:
3:18
So I did what any I think New York hipster would do is I found a cool cafe that was down the street called the rabbit hole. I always love the names in these stories and I would work out of the rabbit hole all day. Honestly, didn't have much better internet and much better cell coverage and they clearly didn't want me to work there because I had a table tent that would say would say no working during lunch rush. Then the power stopped working and they turned off the Wi-Fi. So I was trying to find a solution and that same colleague said, hey, have you ever heard of co-working? And I said, well, I think most people said at that time which was co-what? And there was like one co-working wiki that had all the co-working spaces in the world about 300 of them and one was in New York, a few blocks away, and I decided to give it a try and the name of that place at the time was the Change you Want to See.
Sam Rosen:
4:11
So I ended up with the Change you Want to See and showed up, had no idea what I was getting myself into, and the guy said, hey, are you here for co-working? And I said yeah. He said okay, great, and helped me to get myself comfortable. I had a few rules to be respectful, to not take over too much internet and at the end of the day, if you liked the experience, to drop a tip in the tip jar, girlfriend, and were in design and media and entertainment and just really absolutely fell in love with this idea of collaborative working and working with people other than your colleagues, but together, and I looked to see who is doing this in Chicago and the answer was nobody. But there were already people who signed up saying I'd be interested in this space. So my partner and I decided to give it a shot and that's really like the origin of how I found co-working and that really, I think has been quite instrumental in my path since then.
Alex:
5:14
As you look back on your life and connect the dots that led you where you are now. What are those dots?
Sam Rosen:
5:23
Like when I think about answering this question it always comes to me back to how I was raised and I have a really fabulous family. My mom's a painter, my dad directed television growing up and was in production. So I always kind of grew up in this like mix of art and production and media. That has really guided a lot of how I've thought about and I've always been very, very entrepreneurial. So since I was a little kid I've always had some type of racket, whether it be like self-publishing or doing website design or just trying to find ways to add some value. That led to the design agency, which will be 20 years in January, to the design agency, which will be 20 years in January, and the design agency has really shaped a lot of how I think about the world.
Sam Rosen:
6:11
I've been able to learn a lot about different industries, always sort of thinking about how great design and great brand intersects with really interesting upcoming innovative technology. So that's really been sort of the bedrock of how I think about things. And then I just kind of right place, right time came across workspace and this was a long time ago, 15 years ago but it was always pretty clear to me, using sort of this frame of knowledge that how we work and where we work was backwards. It wasn't oriented around the people who are the workers. It was oriented around their boss or the building owner or the bank. And then, foremost, like these spaces that we work out of are mostly empty, offices have been fairly underutilized for a really long time. Offices have been fairly underutilized for a really long time. So my background in design and thinking about new ways to create value has really driven me into this world of the future of work and how we make work work for us.
Alex:
7:24
Why did you decide to become a leader in your chosen?
Sam Rosen:
7:26
niche For me. I think it's always been about following my intuition and my gut. This path has been very organic and intuitive and I've just sort of learned new things and always been very open to change. So I think it's following what I've learned and how to apply that to new ideas and new things. I think anytime you try to get really good at something, the best way to do that is to learn, it's to listen, it's to build community and connection. So for me, I don't know if I chose this. I don't think as a little kid I thought, hey, I'm going to become an expert in the future of work and the office. But I think just my lived experience and then my curiosity has really driven me to live in this world and learn about this world. And it's been quite fascinating through COVID and over the last few years just to see how much this world has transformed. So it's kept it very exciting and engaging.
Alex:
8:35
What was the best advice anyone ever gave you, and did you follow it?
Sam Rosen:
8:40
One of my favorite quotes is actually a baseball quote. It's a Branch Rickey quote, who was a baseball coach, and my dad taught it to me at a very young age. And that is luck is the residue of design, and I've always really heeded this advice. If you ask anybody, was it luck or was it hard work? It's always a combination of both. And if you just say it's hard work, I think for 99% of people that's ego. Luck is such an instrumental part of opportunity and success. But I think the people that I know that have been really successful have kept this concept in common, which is they work their butts off, they put themselves in the right room in the right opportunities in the right situations and then they let luck do its thing. So I think it's trusting that if you put in the work, you get yourself into the right rooms. If you put in the work and build the right relationships and connections and just be patient, the luck will come.
Alex:
9:50
And what made you choose remote work and how has it benefited you?
Sam Rosen:
9:55
I love this question. For me, remote work was really intuitive. I love this question. For me, remote work was really intuitive. I'm at the age where, you know, in my career, the internet has always been like a big piece of it. So for us, when we're starting the agency, the ability to allow our employees to work where they get their best work done has always seemed very intuitive. The ability to hire people from all over the world, all over different backgrounds and disciplines, has just been made our quality of life, really an experience and ability to execute, I think, much better For me.
Sam Rosen:
10:33
I love remote work, I love people, I love being in the same room with people and I do that as much as I can but having the flexibility and autonomy to work where it makes sense for that day or for that hour or for that project, or being able to respond. I got two little kids, I have a five and a seven-year-old. So being able to adjust my day and my life to be able to support them and be present, adjust my day and my life to be able to support them and be present, and that's what it's all about. I think life's too short to not give yourself, and if you're able to the flexibility to be present and flexible. So I think that flexibility has really been a huge driver for me personally and, as we focus on Desk paths, the ability to help others and make it easier for them to do that has been really quite a joy.
Alex:
11:28
What are your best tips for organizing your day and staying productive?
Sam Rosen:
11:34
Oh man, this is. I mean, I'm like a productivity sort of junkie. So I've tried all the to-do lists, all the apps, lots of different techniques. I think for me, you know, some tactics that are pretty consistent are I have a great, I love a good to-do list. I think really staying organized, having a place like an inbox to put your ideas and thoughts and kind of a process to work through them and organize them, is really cool.
Sam Rosen:
12:04
I use a tool called Aki Flow today, a-k-i-f-l-o-w, which is really cool and I've tried all of them. But one of the big principles in there is time blocking and I think time blocking is really a powerful tool, especially as you're remote. A powerful tool, especially as you're remote, which is setting these dedicated blocks to put the work in and keeping distractions out. So really setting a goal for an amount of time, figuring out the best way to kind of eliminate the distractions that can come from that and just really staying at top of that. That's probably like my favorite tool and tactic right now is a good tool like this hockey flow, time blocking or use like sound to kind of and just like a couple things that I do on my desk to like make sure I know that I'm in a work mode rather than play mode and that might be like hiding other windows or lighting an incense or playing music. That sort of stimulates focus.
Alex:
13:03
So now I want to find out more about the company that you're part of. So can you please begin by telling me more about the company that you're part of and its origin story?
Sam Rosen:
13:13
When we were building a co-working space and being a company that builds technology and design, we started to really riff on ideas and tools to help people run these co-working spaces, and that was called desk time and through that and interviewing and meeting hundreds and hundreds and hundreds of different workspace providers, we realized, man, what these spaces need more than anything.
Sam Rosen:
13:37
It's not fancy technology to run, billing and connect community as much as it is a tool to get butts in seats, really to drive people into these workspaces. So that was really the initial concept behind DeskPass. It was modeled after ClassPass, which did the same thing for gyms, and we thought that was such an interesting model and I think for us, listening to our customers, listening to the data, we've really evolved that model over time to really support companies that are thinking about remote work and hybrid work and allowing their employees to work more flexibly. And we've just sort of listened and evolved the business and the product to support the changes that we're seeing. And I think from when we started almost 15 years ago thinking about coworking or I did so much has changed and evolved and improved. So it's been this yeah, this very natural path from design shop co-working operator to building co-working software to helping these flexible workspace providers connect with individuals and companies that are looking for great workspaces that are more convenient to them in their life.
Alex:
14:53
And what's unique about the company.
Sam Rosen:
14:56
There's a bunch of, I think, really unique things about DeskPass. I think often people compare us to other single operators like Quora in the UK or Industrious, which are all really successful co-working brands. What's cool about DeskPass is it's a marketplace of thousands and thousands and thousands of bookable resources all over the world and they're not all like WeWork or Regis. There are lots of mom and pop shops, there are lots of local operators combined with the big guys, so you have one place where you can see lots of options in your neighborhood. You can find the right space for you and compare it and book it and do all the billing through our platform. So we don't own any of the office space but we partner with all the best operators all over the world. And this means downtown but also like much more rural communities. So that's really unique about our platform. I think. Just also, we really care about design. We really care about user experience. We really care about the brand.
Sam Rosen:
16:10
Like I said, my origin is building a co-working space. So, like a lot of our team members are operators, they've run co-working spaces, they are remote employees. We practice what we preach. And then I'd say, lastly, our model is really cool. Our model is completely pay-as-you-go.
Sam Rosen:
16:31
It's completely utilization-driven, meaning if you're a company and you want to offer DustPast to your employees, you can build a branded to your company solution. You can roll it out to your employees. They get access to it. If they don't use it, you don't pay for it. If they use it, you pay for it. So you only pay for what you use. There's no licensing or minimums or software fees and you can set restrictions and rules to allow you to really kind of control budget and how much someone gets to use this. So it's a really cool way to offer this unbelievably large network of different types of workspaces, but do it in a way that's really flexible, really inexpensive and can adapt to your company and your needs or your personal needs. That makes us a lot different than certainly the traditional office, but even just like a WeWork membership.
Alex:
17:24
What's your philosophy on building a great team? I'm going to keep this one pretty short.
Sam Rosen:
17:29
To me, it's don't be a dick, do the right thing. To me, it's building a great team, is building a great company, building a place where people want to work. Trusting your employees, listening to them, talking to them that's what really matters. I just think life is too short to not build a place where you want to work, and I think that's what we really focus on is building a place where our employees can thrive, where they feel valued, where we are mindful that we're all humans, we're all doing our best, we're all learning. Try to give folks the tools, the guidance that they need, to feel supported, and I think we've been really good at that. Our company is both the best and one design unbelievable retention, like if you take care of your people and they know you're doing the best you can for them. I think it gives you a lot of leeway, a lot of latitude and a lot of flexibility in the hard stuff that comes from running a business and the hard decisions you have to make.
Alex:
18:36
Can you talk me through the steps of your hiring process, sure?
Sam Rosen:
18:41
So I think for us, first we try to hire slowly, we try to be pretty mindful. It's fun to hire someone, it's never fun to have to let somebody go. So we really try to hire slowly, we try to be pretty mindful. It's fun to hire someone, it's never fun to have to let somebody go. So we really try to hire people. When we know there's aires and the philippines and africa all over the united states and canada, that gives us a lot of flexibility and ability to to hire this much broader talent pool. But yeah, I mean, you do your job description, you get the word out there and then we, once we find candidates that really seem like a good fit from a qualitative perspective, we really try to make sure that they get to meet the team, the team meets them, that it's a good cultural fit. We often do a contract to hire so that we can, if it's possible, so that people can kind of get a vibe of the company and make sure it's the right place for them and that they're the right people for us.
Alex:
19:53
How would you describe the company's success so far?
Sam Rosen:
19:57
Man? That's a hard question to ask an entrepreneur. I think, from my perspective, we're always trying to grow, we're always trying to thrive, we're always comparing to grow, we're always trying to thrive. We're always comparing ourselves against others. We're in a relatively nascent new market where there's not a lot of established players and people feels like you're behind and there's always more to do. And then every once in a while you get to kind of step back and have some perspective or have a conversation or some sort of recognition or acknowledgement to realize like no, you've, we've come a really far, long way. I think for us we're one of the sort of most enduring brands DuskPass, you know, flexible work and co-working, I mean, especially here in the States. I think we drive as much traffic to workspaces as any other marketplace provider in the world and we get to work with some of the coolest, most innovative, interesting companies in the world. So I think like we've had a lot of success. But you know, there's always so much more to do.
Alex:
21:15
And what's next on the horizon?
Sam Rosen:
21:18
We really started our journey with external capital, so we raised angel money, we raised some venture capital and that's been really the driver that has allowed us to grow and scale the business. For us, we're focused on a couple of things a, building the best experience in the world to find flexible workspaces, learn about them, book them and experience them, and that's we're always trying to iterate our product and our tool and the tools that we offer teams to really manage this for their employees. And we're focused on continually evolving and improving the platform and the technology and the brand to support that. And then laser focused on building a business that is a profitable, cash flowing business, which we're very close to and I think will give us a lot of flexibility and the ability to endure the future and really control our destiny to what we want to build, how we want to build it, sort of what the right pace and right decisions are for us.
Alex:
22:26
Is there a particular team or company whose culture you admire?
Sam Rosen:
22:32
Well, I'm a Chicago boy so I tend to think about companies here that really inspire me. I mean, I think the one that always comes top of mind is Basecamp, the project management software, the 37 Signals that's built all sorts of other really wonderful tools written New York Times bestsellers on remote work has really built a philosophy around remote work, around a quiet, calm company, about a profitable, cash-flowing company, controlling your destiny, really supporting employees in a work-life balance and not sort of mixing business with family. There's other companies in Chicago, like Field Notes, which is such a cool brand, or Jim Cuddle, who's the founder, is a really inspiring human to me. Yeah, I like Tiny, which is not a Chicago company but that has built so many cool projects that kind of came from design and then investing and building and supporting other companies. So I mean those are companies that come to mind. Growing up I was such an Apple Steve Jobs nerd so I always sort of look to them and see what's happening. So yeah, I think those are a few acts that come to mind on the fly.
Alex:
23:51
And, as we begin to wrap up, what excites you about what's ahead?
Sam Rosen:
23:58
One of the things that I think is so cool about how the world has changed post-COVID, around how people work and where people work, is the world has become.
Sam Rosen:
24:08
Corporations have become a lot more adaptable and recognize that people can be productive and effective outside of the office and, at the end of the day, what that means more freedom, more autonomy to the 99.9% of people who are not the boss, who have to get the work done, and giving them the tools and the flexibility to really build a life, a lifestyle that is much more cooperative with their job and less of like a job versus life, and allows people to kind of build the right chemistry that supports them. So I think one of the coolest things about this drive and growth in remote work and worker flexibility is really just allowing people to live. I think that will continue to happen. I think that we're just still at the beginning of this and there's going to be so many more tools and technology and cultural changes that are really going to support this and we're really even though I've been doing this almost 15 years we're still in the early innings and I think it'll be really, really wonderful for, hopefully, the humans that have to do the work.
Alex:
25:31
And what do you like to do when you're not working?
Sam Rosen:
25:34
I'm a dad man. I have a five-year-old, I have a seven-year-old. I love being their dad. I think one of the coolest things about being a parent is a reminder to be present. And I just have this wonderful little window where the kids are young and we all love each other a lot and we're their world and I just like I'm trying to spend a lot of my time and energy appreciating that and enjoying it while it's here, before it changes Other than that. I love to travel, I love to eat, photography, I love taking photos. Those are the things that. Really. That's more than enough with a full-time job running Best Pass.