This is the full transcript for Episode #287 of the Wild Business Growth podcast featuring Sam Rosen – Coworking Space Pioneer, Co-Founder of Deskpass. You can listen to the interview and learn more here. Please note: this transcript is not 100% accurate.
Sam Rosen 0:00
This is like the Wild West
Max Branstetter 0:16
Wild. Welcome back to the Wild Business Growth podcast. This is sometimes I say bodcasts like a podcast about any body you want to imagine I don’t know where that was going. Welcome back to the Wild Business Growth podcast. This is your place to hear from a new entrepreneur every single Wednesday morning, who’s turning Wild ideas into Wild growth. I’m your host, Max Branstetter, Founder and Podcast Producer of MaxPodcasting. And you can email me at to save time with your high-quality podcast. This is episode 287. And today’s guest is Sam Rosen. Sam is the Co-Founder and CEO of Deskpass, your spot to find coworking spaces, hybrid office spaces. They got everything there from meeting rooms to individual desks. And in this episode, we talk everything from the very interesting early businesses Sam started him being a pioneer with the first ever coworking space in Chicago. The best lessons and stories from his parents who are both some of the most creative people you’ll ever hear about it not that Sam’s not creative. And his top entrepreneurship tips as well as top Chicago architecture cruise recos. It is Sammy Rosen. Enjoyyyyyy the showwwwww! Aaaalrightyyyyyy we’re here with Sam Rosen, Co-Founder and CEO of Deskpass, one of the deskpassiest companies, I don’t get to say that often. Now one of the coolest companies in the co working space that he’ll come across Sam, so excited to speak to you Mr. Rosen, how you doing today.
Sam Rosen 2:07
I am very happy to be here. So I appreciate appreciate the time excited to chat.
Max Branstetter 2:12
Perfect. Well, I’m very happy to be here as well. And actually, we’re basically family because my mother in law’s maiden name is Rozen. Although it is spelled with a Z Rozen. So I don’t know if there’s a little rivalry between the Rozens and Rosens. Yeah,
Sam Rosen 2:29
I thought we were family. But actually we’re we’re enemies. Unfortunately,
Max Branstetter 2:34
mortal enemies Rozens/Rosens nonetheless. But now we’re really excited to get to all things desk fast. But before that, a little rollerblading birdie told me that back in the day, one of the first companies that you started was a rollerblading delivery service. Can you reveal the awesome sick wheels on that one?
Sam Rosen 2:55
Wow, I out of the gates. Man. I’m so impressed with your diligence here. That’s a deep cut. Yeah, I am. I’m one of those kids who’s always had some, some business and some idea that I’ve worked on one of my first and favorite failures was Lincolnwood, Illinois. That’s the town I grew up in. So good Midwestern boy, suburb of Chicago. And I thought there was a huge demand for a local rollerblade messenger delivery service. Before Uber, you know, had the ability to send packages, we thought, me and a couple buddies could just get calls hop on our rollerblades and transit packages and goods from house to house. It was one of those ideas that like, you know, seemed really good. And concept is like a 11 or 12 year old, but it didn’t. didn’t pan out, unfortunately.
Max Branstetter 3:53
Was it just because your legs got too tired? Yeah, I
Sam Rosen 3:57
mean, the demand was there. It’s just strong enough. Yeah. No, it was hard to market yourself as a 11 year old local delivery service. But I feel like with the internet now, like probably a new opening opportunity for this type of service. But yeah.
Max Branstetter 4:13
Well, there’s something about rollerblades that are so fun, and just like take you back to like the 80s 90s. And those What is it like Beverly Hills movies with like the cops on rollerblades and like that sort of thing. So. So if you picture that and then picture, an 11 year old kid carrying 17 packages, that’s a great combination, but I love the ingenuity there.
Sam Rosen 4:34
It was a fun idea. And I really appreciate you reminding me and opening up with with with with a tough, a tough early childhood failure.
Max Branstetter 4:44
Yeah, of course. Well, next we’re gonna get to that that Lego set that you never finished. No, just it’s pretty impressive. Whenever you hear about kids starting businesses, or at least like you’re about that entrepreneur, entrepreneurial bug starting early even if you can’t print onset. Like, did you always have a history of starting pretty creative outside the box business ideas like that?
Sam Rosen 5:06
Yeah, my next business after that, which I would say in hindsight is quite a success was a beat poetry book called Pure Truth. It was self published. And basically, I don’t think anyone still has copies except for my 96 year old grandma. So you’d have to go real hard to find that one. I don’t think she’s giving it up. There was two editions, there was the first edition, the Pure Truth, and then the second edition and that I thought was kind of, you know, it was like, truth. What is the truth? Why can’t we always find the truth? I hope you find the truth pure truth like that was pretty much the format on multiple subjects. big seller in the local Lincolnwood community. So we did a follow up pure truth, the new addition where my parents told me I sold that which is pretty good lesson for a 15 year old but yeah, published a book sold it at the local healing or at the resources like the local like metaphysical bookstore, made enough money to buy a Fender Starbuck burst guitar, so I’d call that business. But I’ve been, you know, since I was a little kid, I’ve always had ideas and just enough gumption to give them a roll. No,
Max Branstetter 6:23
that’s it. That’s an awesome payoff for any anything fender but how did you at that age get into beat poetry? I feel like you were what you were a poet beyond your years.
Sam Rosen 6:35
You know, my mother is a fine artist. She’s a she’s an incredible painter. My dad directed television growing up and produced television commercials. And I grew up in this really cool creative household that was very, like art meets production. And I grew up with like mid century furniture and books on like, Japanese modernism and Zen philosophy. So I think like, I’m a byproduct of my parents and kind of, you know, their interests.
Max Branstetter 7:12
Let’s use that as a little bit of rollerblading, foreshadowing, because I definitely want to dive deeper into that later in this interview. But for now, let’s get to desk Pass, which you might think has nothing to do with rollerblades and beat poetry but obviously those were influential in more ways, in more ways than one but coworking. We’re recording this at a time where co working is like pretty well known. It’s a lot of people have either cowork to themselves or been, you know, visited a co working space, or at least have familiarity with it. But that wasn’t always the case. Can you explain what that landscape was like in 2008 ish. When you you started the coop, the first co working co working space in Chicago?
Sam Rosen 8:00
Yeah, man. So before the coop and before best paths. And still today, I’m a partner but I founded a design agency called one design companies, wonderful little design branding technology agency that does work in Chicago and all over the world. I was traveling, oh, Fairmount. I had a girlfriend who moved not so far from you and South Williamsburg. And I was traveling there every like three weeks, and I’d go visit her and she was and is still very cool human. I would work and run my little agency business out of her garden apartment, which had terrible internet, terrible cell coverage, and a thin layer of clothing covering the entire floor.
Max Branstetter 8:48
which everybody knows is awful for Wi-Fi connection. Just got Yeah, I
Sam Rosen 8:52
don’t know what the deal is with random clothes and latency. But that’s a real proper
Max Branstetter 8:58
soundproofing. Probably, yeah,
Sam Rosen 9:00
great acoustics. But basically, you know, I was working, she’d go to her job. And I would work out of her apartment. And this little agency was starting to grow. And we just had our first project, our biggest project today for film workers club in Chicago post production company. And we are kicking off the project. And I was in charge of kicking it off, and I was on a call with my colleagues and the client. And I dropped the call five or six times during this kickoff meeting. And my buddy, no colleague was like, bro, can’t do that anymore. And I was like, Cool, cool. Okay, I can’t do that anymore. So I did what any millennial hipster entrepreneur might do. And I went to the local coffee shop, which and I love the names in this story was called the rabbit hole. And it was this really groovy little cafe. And I would sit there all day. They had no clothing on On the floor, but their internet was not much better. And I would say their cell phone service was not much better. And I would sit there all day, I’d get one bagel, two coffees. And over time, I could tell. They didn’t like my kind there. And by my kind I mean loiterers. And basically, at first it was like, can’t use our internet anymore. Like CES, like, no one can use the internet anymore, then it was like no computers over, you know, the lunch rush. And then it was like the outlet stop working. And I was like, Okay, I get the point, I’ll find a new home and this recurring figure in my life, and Noah said, Have you ever heard of co working, and I in 2008, said the same thing that pretty much anybody would say to that, which was cola. And he showed me a Wikipedia of co working. And that was the most authoritative source, I’m co working in the world, and happened to be a co working space a few blocks away from her hubs, which was called the change you want to see. Which in hindsight,
Max Branstetter 11:03
that sounds like an entry from your beat poetry book does actually,
Sam Rosen 11:07
that’s very true. And I thought, That sounds weird. And it was like a gallery, that during the day, they was a nonprofit, co working space. And it was a few blocks away. So I showed up. And I showed up and they said, Hey, like go to the space? Or like, where are these people? There’s a big table, lots of people, much better internet, quiet places to take phone calls. But the guy goes, Are you here for the coworking and I was like, yeah, he’s like, awesome. Got three rules. Don’t be respectful. If you’re gonna take a phone call, take it over there and don’t download any porn. And I was like, Yeah, I can totally, I can totally do those rules. You can get most of those. Yeah, I got two out of three of them very easily. And I know I fell in love with this little place. Like it solved the very pragmatic issues I had around internet and connectivity. But I actually found some really phenomenal people that weren’t my girlfriend or her friends. And so I walked into a community of like people Design and Media and Entertainment and like, made connections and made friends and immediately had like, new people. And I was like, This is amazing. Who’s doing this in Chicago? And the answer was not a sales person, there was a list of people who are interested, which are actually some really cool people, but no like venues. So my partner and I had agents who were like, Let’s turn this empty space we had, which was actually my apartment next to an office. And let’s turn it into the first co working space in Chicago. And that’s how, how we got started. And there was already people wanting to show up. So it filled up really quickly at the beginning.
Max Branstetter 12:46
I got me I already mentioned porn, but I got scared for a second when you when you said that. You started to say there were no clothes at this coffee shop. I thought you meant like it was like a nudist colony or something. I’m like, oh, you know that that spans wonderful ideas there. But like many businesses, I’m sure were started that way. But no, you were just saying no clothes on the ground there. But that’s like a really, it’s overused, but organic way of coming up with a business, like an aha moment because you literally experienced the problem yourself, and then look for answers. And I can’t even tell you how many guests on this podcast, like super successful, awesome entrepreneurs. Like went to Google something, and it just wasn’t there. And they’re like, oh, okay, why don’t I create this? And so it’s awesome that you did it as well. Shout out Wikipedia. But what was helpful in terms of making the jump from like, Alright, there’s clearly a space in the market for this to alright, I’m actually starting this and actually, we’re going to take this a step further even.
Sam Rosen 13:53
I think organically the co working space just worked because kind of Right Place Right Time. I mean, some really cool original members like Charles Adler, the co founder of Kickstarter, Ryan Graves, who was at one point the CEO of Uber, like the fucking can I swear, sorry.
Max Branstetter 14:13
You can Yeah, you can even say James Yeah, yeah.
Sam Rosen 14:16
The James Bond like title sequence was done in our like, one of the animators is we’re gonna
Max Branstetter 14:24
go to the movies movie or Yeah,
Sam Rosen 14:26
yeah, well, movies. Not all of it, but like a part of it was kind of in
Max Branstetter 14:32
half a second. No, just
Sam Rosen 14:35
took three years. But it was just like, This is amazing. This is a amazing little community and vibrant and I again, I met like really interesting people that I don’t think I would have come across and it just, it was something that was very obvious to kind of grow and scale and I think me My background is really in design meets technology. Immediately you start going to this place of what type of technology can make this better, you know? And it started with, how do you manage the space just in the building and the scheduling and community. And that’s where this path of creating something more in the space other than just a physical co working space really started.
Max Branstetter 15:20
So where do you see an opportunity to, I guess, hint at something closer to what desk pass is today like this type of business? Yeah,
Sam Rosen 15:27
man, I think I’m having like a full circle moment recently. Because I think, again, like being a designer, you really, I think, often have a perspective that’s different than other folks. And I think co working is a real estate play, right. Like, it’s always been a workspace solution. And I think when I started to kind of focus my thoughts on the office, I realized a couple things that are, this was, you know, 16 years ago, but I think that are even more prevalent today, which is, offices are pretty empty, they were pretty empty. 15 years ago, they might be more leases, but actually like utilization butts in seats, like it was very clear then that the average dusk was sat in like three hours a day. And that was considered like fully occupied. I’m no mathematician, Max. But that’s like 15% of the day, or the full day, and you looked at a city like Chicago, and you knew like, you don’t have to build another building for the next 20 years. There’s enough office here for to adopt for the next 20 years. And just that this idea of the way in where we work seems misaligned with the workers, right, that the Office experience had more to do with like, your boss, and where your boss lives or like your landlord, and like their relationship with the bank, compared to like, what is max doing today? How where does he have kids? Does he have to pick them up from school? Like, is there traffic, like it does need to be creative today. So it just seemed like there was a miss opportunity. And then just a whole ton of empty space. So that’s what really got the kind of brain work. And I’m like, can you start creating, make this easier for people and create a place for people to share their empty space?
Max Branstetter 17:23
And I think if you look at desk paths today, just like even from exploring the website, you can see like, how easy to use it as how, like how simple the, I guess value proposition is, in the in the service it provides. And anybody who has wanted to use a co working space in the past and hasn’t used desk pass knows that like, kind of like the start of your story, like, you’re kind of scurrying around, like how do we even know where to where to find a spot? Like where do I find a conference room or a desk or something for this call? It’s a real solution. You’re providing their experience? Yeah, of course. What would you say is the most common way that people are using desk pass today? Like, is it more like big scale corporations looking for lots and lots of rooms or more like indie printers, you know, individual desks, like, I have no idea what the landscape is, like. I
Sam Rosen 18:16
think like, you know, it’s like the curve of adoption, right, like the early bleeding edge. People were like creative freelancers, like very early remote workers. And then I think we’re sort of past the sort of tranche and the chasm, as they sell
Max Branstetter 18:34
quick tranche is an incredible word. I don’t know. No, I’ve heard trough but tranche I think is a new, a new way. Almost. I, that sounds good to me. Let’s go with it. Yeah.
Sam Rosen 18:51
But I think what’s happening now is COVID really accelerated people, the understanding of companies that their employees don’t have to be in the office every day to get their work done. That doesn’t mean they don’t have to be in the office. That doesn’t mean the office isn’t important. But this idea that like, you have to come here, nine to five, to make a living, I think is probably the most enduring legacy of COVID. Right. And the reality is the office has always been this like one to many thing, like we have one office, that’s where you get trained and educated. And that’s where everybody is, and communication. I think, what’s happening as we’re seeing this, like many to many changes you saw with like, media and entertainment, where it’s like, what is the right configuration for Max and his life? Today might be different than tomorrow, which is probably different than sounds, or Judy’s, you know, like so. What you’re starting to see which is really cool is you’re starting companies, some of the biggest companies in the world. We have a contract with the federal government, right, that are starting to say to their employees is look, we recognize office is evolving from just one place you go every day to an ecosystem of neat workspaces where you can get your best work done. And we’re going to support you. So that’s really what we’ve been doing is we’ve been helping companies and individuals alike find this network of space and use it when they need it. Like for exactly how long that they need it for.
Max Branstetter 20:25
If you don’t mind sharing, what are some of the like, the bigger name companies or like, companies that I’ve had many people use your services that some people might recognize that our clients here’s?
Sam Rosen 20:35
Yeah, I mean, we have all sorts of interesting customers. I think some that I can like, say out loud, or like, Synchrony Financial good RX. Like we want a contract for GSA, which is the administration hub of the federal government. So you have, you know, federal agencies that access our I think, right now, USGS was a customer of ours help us get in trouble.
Max Branstetter 21:00
We’re just gonna set we’re gonna, well, we can always call it out. But basically, anybody who’s an acronym is like, yes, we want desk pass.
Sam Rosen 21:09
We crush it with acronyms. That’s our ICP.
Max Branstetter 21:16
Wow. Now, in the spirit of making me look like an idiot, can you tell me what ICP means?
Sam Rosen 21:24
It’s like the customer persona that you’re going after. So it’s,
Max Branstetter 21:28
I was gonna guess. Yeah, yeah, I
Sam Rosen 21:31
forgot the eyes for right now. But I’ve just because I’m on the spot, ideal, ideal customer persona.
Max Branstetter 21:36
Oh, there we go. Perfect. I would just call it ICP. But anyway, way cooler. What has been key in attracting and attracting these acronyms, like what has been key in attracting these big name clients and continue to snowball with that over the years. This
Sam Rosen 21:51
is like the Wild West. This is a new territory. So I think like, ideally, people get it. They’re like, Yeah, this makes sense. I think companies are complicated and rigid and sometimes move slow to different companies. Some have been really quick out of the gates to adopt this. Some have adopted it long before COVID. Right. But I think companies, you know, the first thing they do is they say like, what do my employees want? And then they ask their employees, at least smart companies do that. The problem with that is I don’t think employees know. And I use the stupid metaphor, but it really like resonates with me, which is like you’re working and you have a light switch and the light switches in office out of office. Oh, should have probably turned off those reactions out of office. And
Max Branstetter 22:45
for those for those listening a giant thumbs up just appear next to Sam’s head. So we are just living in the metaverse here. Nice. I’ve
Sam Rosen 22:54
been waiting for that to happen on a podcast. And I I’ll save the best hand signal for last. But so you have this you have this light switch on and off. And essentially what companies are doing is they’re they’re installing a dimmer and in your office configuration, and they’re saying how much light do you need? And you’re like, Well, I only had 0% and 100%. I don’t know, maybe I need 30% light, maybe I need 70% light, right? So I think like what we’re trying to do is make it really, really easy for companies to install a dimmer and not just ask their employees what they want, but give them the option and then understand and learn their behavior. So there’s no Harvard Business study at about, like the best practices, there’s a million emerging thought leaders that talk about this that like they’ve been doing this for 20 years. But the reality is, I think just the awareness that these solutions exist to the maturity of the supply, like there’s way more awesome spaces that sure helps. And then you know, the reality that some people are saying, I’m never going back to your office. So if you want to keep me around, you’re gonna have to offer me something else.
Max Branstetter 24:09
I dig the dimmer analogy. Like there’s, there’s so many nuanced situations these days where it just helps to have so many of those individual situations available. And so you’re making so much of that possible, um, like the actual physical spaces and like all the different companies that you know, are co working spaces themselves that are part of your, your network, if you call it how do you create connections that way and, and also on top of that, sorry for asking two questions. On top of that, how in the world do you manage like 1000s of spaces like this? Yeah,
Sam Rosen 24:44
so we’re like a marketplace or a connector, right? So we connect these individuals and companies with existing professional folks who do this for a living, right. So, you know, we’re a technology company that has figured out like Lots of these spaces are different. They use different technologies, they have different rules, they have different pricing. And we’ve just tried to put like the train tracks down and that help connect the dots, you know, between them. That answered your second question, but I don’t remember your first.
Max Branstetter 25:17
That makes at least two of us. Yeah, it was more about, you know, like, it’s one thing to attract customers in terms of people that are actually using these spaces. It’s another thing to actually attract these spaces as part of the network, like, how do you? Yeah, have you been able to scale that over the years? Frankly,
Sam Rosen 25:35
that’s the easier part of the equation. The reality is like, today, I’m in Washington, DC, and I’m in the middle of K Street, and like, I’m looking at these office buildings across the street, and they’re empty. And the same thing in Chicago, probably the same thing in a book and I don’t know
Max Branstetter 25:54
about can I like it.
Sam Rosen 25:58
These offices are changing and demand is changing. So I think if you there’s just a lot more opportunity for these spaces. So you’re seeing for a long time, the first gen were people like me and the coop, that would lease the space from a landlord now essentially arbitrage right, like I’m paying this rent, and I can collect this around, but I’m on the hook, irrespective of whatever happens right? Now, what you’re seeing is you’re seeing landlords themselves saying, Look, if part of this building has to be flexible for my tenants, to be a competitive building, then I have to do this. And I might do this by building my own brand. So there’s landlords that are building their own co working brands. And then there are folks like our partners and industrious and a bunch of other smart savvy, co working and flex operators, that partner with the landlord and they say, look, you’ve got empty space, I can help fill it up. I can drive revenue to the building and turn that empty space into revenue. But I can also activate this space build community and be this awesome amenity for your tenants already write? For us. We’re driving people and money into their spaces, and they’re looking for those two things. So it’s an easier proposition than convincing people to get out of their, their cozy homes into these spaces.
Max Branstetter 27:22
A cozy virtual space that you you shall enjoy. I don’t know I said it like that, that you might enjoy is on YouTube @MaxBranstetter Yes, there are full video interview episodes like this one was Sam, that you can check out on YouTube @MaxBranstetter. You just might even catch thumbs flying every which way hopefully up. Make sure to hit subscribe while you’re there. That is YouTube @MaxBranstetter. Now let’s get a little Hollywood to which the critics are saying two thumbs up two more thumbs up. So let’s switch gears a little bit before any you know flying thumbs up any more come up because you got to watch out for that but but thumbs up all around, but you foreshadow this swimmingly earlier, as we hinted at, as we foreshadowed the fact that you have to incredibly creative, inspiring parents that, you know, have the creative skill set, obviously, like careers in the creative space and, of course, impacted your own design career, which we’ll talk about, but to set the groundwork for that, you know, I know you mentioned that you’re dead, that budget of TV commercials and directing, producing that sort of thing. But I also know that your mom’s paintings have a bit of a Hollywood tie as well. Can you share that hack?
Sam Rosen 28:47
Yeah, I there are fewer things I’d like to talk about more. is literally my friends that are artists. My mom is like the artists artists since I was a little kid. I grew up in her studio, and she has 1000s and 1000s of paintings. And she would paint all day every day, irrespective of if anyone ever bought one. She doesn’t care. That’s not why she does it. She’s just a she’s a maker. She got connected to the team at Grace and Frankie, which is the longest running show on Netflix. It was there last season, I think it was last year with Lily Tomlin and Jane Fonda. And if you haven’t seen the show, it’s brilliant and hilarious. And in the show, Lily Tomlin is Frankie, and she’s a painter. And all of the paintings are hers that my mom’s paintings are the studio is like, remnants of my mom’s studio that were shipped from, you know, Chicago to Hollywood. So that was a very cool thing and has given my mom really interesting exposure all over the world.
Max Branstetter 29:59
That is one of the best Fun Facts I’ve ever heard. It’s not just a fun fact. It’s like your mom’s career and it’s been seen by what millions and millions now, I mean that that is just awesome. My wife Dana loves that show. And I know so many like so many diehard fans of that show, so it’s a great to make sure we have to make sure when she rewatches that she looks pays extra close attention to the paintings.
Sam Rosen 30:22
There’s a episode that is like Frankie’s big art show where they like blew up my mom’s paint and she’s an extra in that episode. I’d look for that episode, which is like the gallery one. And
Max Branstetter 30:34
then how about your dad so your dad did all the greatest painting? No, I’m just kidding. So what kind of what kind of commercials and things to do dad direct slash create?
Sam Rosen 30:44
So my dad was like a very early you know, Chicago, which is was more of a hub for for this type of stuff back in the day less so these days, but with shoot big, you know, half a million multimillion film commercial productions for you. I mean, you name it and like the glory and heyday of commercial filmmaking. So like, I don’t know, my favorite commercials are probably most notable were like, for when there was the Michael Jordan, like addition, Chevy Blazer, and he had like a Chevy Blazer, like floating in the air. And Michael Jordan was in the commercial. But he’s done all sorts of really interesting, cool commercials. And it was really fun. Growing up, like, and I attribute so much of like, my character to like, you would be pacing down the halls like, you know, producing and I just have our house and I just like I loved growing up in that environment.
Max Branstetter 31:42
Does your dad get to meet? We’ll call him Michael as part of that.
Sam Rosen 31:46
Oh, yeah. He directed him.
Max Branstetter 31:48
I was gonna say that. That’s better than meeting does. Does he have any stories? His interactions with him?
Sam Rosen 31:54
Like I just remember asking and him being like a super nice guy. And my dad’s actually met a fair amount of, you know, hilarious like Cal Ripken, Jr. and Bobby Cox and like, some funny figures throughout throughout the years, John Smoltz. Yeah.
Max Branstetter 32:09
Did he do a lot of work with the Braves? Or is that just a coincidence?
Sam Rosen 32:12
weird coincidence? I think it was more like the Atlanta lottery.
Max Branstetter 32:18
All right. No, that’s, that’s a dream, though. Like, when you could do something professional. And obviously, like, with your career with your parents careers, like we’ve we’ve talked about very different forms of this. But when you can do something that you love for a living, it’s a game changer. And it’s like when there’s something that you can just be excited talking about. And from your parents standpoint, that your, your son can be very excited talking about publicly and sharing embarrassing stories, no, just guy. But it’s, it’s a really powerful thing. And you know, you’re on a good track there. But from your parents is there. If you had to pick one, what would you say is the most valuable lesson you’ve learned from them about creativity and business?
Sam Rosen 32:59
I think one of the things that I really loved about my childhood, I’m a nice Jewish boy from the North Shore, right? And it was Sam you could do and be whatever you want, when you grow up, we’d prefer if you are not a doctor, or a lawyer. And I think that pretty much sets the sets the setting for how I was raised, right, like, and I’m a dad. And I think this is a really important value that has been given to me, which is my parents wanted me to find what gave me joy, and what lit me up. And were very, very supportive, and allowing me to figure it out. They didn’t prescribe. I wanted to be a director, you know what I mean? But they never told me to, they let me follow my bliss, supported me, never told me what I could or couldn’t do. And I think that is like a really valuable lesson. And I know I have unbelievable privilege to be in that situation where I have that opportunity and that choice and, you know, loving parents who said, Do what fills your cup.
Max Branstetter 34:11
That’s really special. I mean, that you can literally change your kid’s life and trajectory forever when you when you have that sentiment and support and encouragement. And as a nice Jewish boy from the south side of Solon, Ohio. My parents also had that same sort of sentiment, and we’re just so encouraging no matter what I wanted to do, like, if I wanted to go into the corporate world, leave the corporate world startup business startup, you know, when I was younger, playing music, like anything, just so supportive and encouraging and helpful along the way. So that’s, it’s really special when you can be that way. Parent. Now. I’m like talking to parents out there. So on that, on that sappy note, let’s wrap up with some rapid fire q&a. You ready for it? Let’s go All right, man, power clap thunderclap events. Let’s get wild. If you could only eat one restaurant in Chicago for the rest of your life, what would it be?
Sam Rosen 35:13
Renga-Tei. It’s a sushi place I grew up going to. Oh, no, take it back. It’s too late. Yeah,
Max Branstetter 35:19
it’s 2 places. But yeah, you can go for it. Go for it.
Sam Rosen 35:23
I mean, the most classic, most wonderful restaurant in Chicago is Lulu cafe. And if you haven’t been there, it’s been there. 20 years, and I would pick Lulu I rescind during a great restaurant, but more of like a deep cut.
Max Branstetter 35:39
Sam Rosen gets cancelled by Renga-Tei. That’s the headline after this one. All right, what’s like a physical co working space in the desk past the desk past the desk past network that is in like a really cool, unique location. So
Sam Rosen 35:56
one of my favorite spaces in Denver. There’s a space called furniture. It’s like a triple entendre. I don’t know, I might be making that up too. Basically, in the back is a print studio like letterpress printing studio and and printing. What you put on the letterpress is called furniture. But it’s also in an old furniture shop that they retrofitted into a coworking space. So I think like I just love all the pieces to that story. And it’s also a wonderful, wonderful workspace, but it’s just like a printing studio in an old furniture shop called furniture.
Max Branstetter 36:36
It’s very, very supportive. Great back lumbar support. Perfect. Alright. As was actually formative to the business. You know, you spent you said about once every three weeks traveling to South Williamsburg to visit your girlfriend and her close. I’m just going from Chicago. What advice it doesn’t have to be relationship wise. But what advice do you have for anybody that has to commute? has to travel like that frequently and make it part of their life? Like, what’s the best way to go about that without being burned out? burned out? All right, Max, that relationship didn’t work out. No. Maybe you have an example that we can use as a learning moment.
Sam Rosen 37:18
No, man, I mean, like any relationship, man, it’s all based in trust and communication. So I like my, my dear, dear wife, she she gives me a long leash and she trusts me and I was I’m staying with a buddy and he was like, Do you have like your windup bedtime routine call you have to do and I’m like, Nah, they don’t need me like this. Like they don’t care. It’s fine. We’re good.
Max Branstetter 37:45
No, I actually I’m gonna spend an hour ranting about a place called furniture instead. So I can’t do that. All right, and then last one. Sorry, kidding. Second, last one, what is the hidden gem in Chicago that like, it’s not quite as touristy as then you’re not gonna have the mobs of people taking pictures of the bean, or whatever it’s called. I always forget the name the but it’s like a really cool spot to check out. If you’re visiting Chai, Chai town,
Sam Rosen 38:12
and underrated thing. It’s kind of touristy. But like it’s, it’s never busy and crazy, because I hate things like that. So growing up, I grew up in Chicago, and everyone’s like, Oh, Chicago, like gonna go to the city. It’s such a beautiful city. And it is. But like, I don’t know, like a good architecture, like I never really appreciated it. And I went to do the architectural boat tour. And there’s a few different architectural boat tours, but there’s one that’s I think it’s architecture.org. And it’s by like the, like historical like architecture society and the docents. They don’t get paid, they just love it. And you take this and then same thing, there’s a just a river walk, you get the same experience, but the boat tour is really really cool. It’s such an unbelievably beautiful, awesome way to experience Chicago. And I remember the first time I did that a little picnic on the boat and like wine and cheese and and just being like, oh my god, this is such a beautiful city. If you want to go kind of another really great Chicago hack, same river, is you can rent an electric boat for like a couple hundred bucks, get like a group on or something like that. You don’t need any training. You don’t need any license. You don’t need any experience. And you can take a little boat out on the river with some friends and just like rip up and down the river. And that is so fun to do. And just like you when you’re doing it, you’re like I feel like this is not legal, but it is. I think
Max Branstetter 39:46
yeah, camping legal. No, those are those are those are awesome recommendations we did. We visited my buddy Spence in Chicago last summer. Actually a little funny story about him. We did a boat tour with him because it’s like you got everybody you have to Do It and it is awesome. It like exceeds expectations. And the docents are awesome. Spencer, actually, who lives in Chicago had a work event the day before, where he did that same boat cruise. But he still did it again with us the next day. He’s like, Oh, why not enjoyed it the second time too. But also, throughout it. We Yeah, exactly. We saw plenty of bachelorette and bachelor parties on those rental boats. And let’s just say it’s fantastic people watching, if anything. No doubt. All right, last one, for real you, somewhat recently, at the time of this recording, did a merger with breather and so you had your company, I guess is in transition. But it’s a really cool thing. Whenever a company goes through a merger, any sort of big milestone like that, what um, we don’t need to you to like spill out all the financial agreements and everything, but maybe your social security number, but besides that, what’s just a piece of advice you can share for anybody that is considering going the merger route,
Sam Rosen 41:03
it takes a long time. You know, like, I think, look up mergers on marriage, you want to really take the time to get to know your partners, and you know, the platform and kind of what you’re getting into I think for us, we were really lucky we breathers is really cool business that like exploded, and then kind of got hit with COVID, just in a hard way. And it was owned by industrious, which is a wonderful, wonderful, second biggest co working brand in the world. So this this deal formed a partnership between us and industrious. And then we got this wonderful business in breather to kind of inherit and try to operate. But I think like, Yeah, I think like, you want to do your best to get to know what you’re getting yourself into. And then you want to make sure to build like the right long term relationships, because I think that’s what really drives value through and through, but I don’t know, it’s like, as an entrepreneur, as someone who’s tried, you know, have some cool, sold a company, you know, been able to buy a company, like, it’s a really fun thing to like, get to like work with somebody else’s business in an intimate way. I think as an entrepreneur, you’re always just like, you know, I don’t care what you say, like you don’t know what you’re doing. You’re trying to figure it out as you go. And it’s really fun to like, start working with somebody else or another business. We’re like, oh, that’s how you made it. Right, like, and this is how we’ll make it up together. And that’s, so you want to find the right people to do that with
Max Branstetter 42:33
lots of great improvisers out there. Well, Sam, thank you so much. Lots of great poets, as well by the sake in rollerbladers. But, Sam, thank you so much. This has just been fantastic. And it really appreciate you sharing your journey and everything from your mom’s paintings to your second favorite restaurant in Chicago.
Sam Rosen 42:52
It’s a banger. Where
Max Branstetter 42:54
is the best place for people to check out Deskpass, which I finally pronounced correctly. And if they want to connect with you somewhere online,
Sam Rosen 43:02
yeah. So I’m Sam, at SammyRosen.com. Go to SammyRosen.com. And you’ll kind of see all my tentacles You know, on the desk past,
Max Branstetter 43:13
sorry, I took that totally the wrong way. Sorry, go on over your mind, your mind.
Sam Rosen 43:22
On the Deskpass front, like we help companies small, medium, ginormous, tackle this problem of what they’re going to do to support their employees and their team in the future. And that’s what we love to do. And we have a great team of people to do it. So like, that’s fast.com Sam deathbeds.com Hit us up, like we’re here to help even if we’re not the right solution. Like, I think we have as much domain experience and helping companies figure this out as anyone else. And that’s what we love to do. So just hit us up and we’re here to help. Perfect.
Max Branstetter 43:57
And then last thing, Final Thoughts. It could be a quote, a line of like a slam poetry to end with or it could even be just revealing one of your tentacles, whatever you want. Send us home.
Sam Rosen 44:10
Oh, man, you know, I think my like one of my favorite mantras and I think it kind of fits my little narrative and it’s something my dad taught me is luck. It’s a baseball quote too. So we’re really like we’re really tying it all together here.
Max Branstetter 44:25
You’re knocking out of the park.
Sam Rosen 44:27
It’s a hey, it’s a Branch Rickey quote, and it’s luck is the residue of design. I believe that I’m the most successful people that I know and you know, it’s not an accident. Like there’s a lot of a lot of luck involved but like, you know, putting yourself in the right room putting yourself in the right position. That’s where you you can get on base.
Max Branstetter 44:54
A grand slam for the pennant from Slammin’ Sammy Rosen. Thank you so much, Sam, for coming on the podcast, sharing your incredible Deskpass and even rollerblading and painting journey. And thank you, Wild Listeners, for tuning in to another episode. If you want to hear more Wild stories like this one, make sure to follow the Wild Business Growth podcast on your favorite podcast app. And subscribe on YouTube. That is at @MaxBranstetter. And tell a friend about the podcast. If someone you know loves entrepreneurship, and the wonderfully best jokes you’ve ever heard, like in this interview, make sure they know about Wild Business Growth. You can also find us on Goodpods, where there are good podcasts and podcast recommendations. And for any help with podcast production, you can learn more at MaxPpodcasting.com and sign up for the Podcasting to the Max newsletter that is at MaxPodcasting.com/Newsletter and it’s where Max stumbles over his words. It is where podcasting meets entrepreneurship and terrible jokes. Until next time, let your business Run Wild…Bring on the Bongos!!
