Sam Rosen: natural born entrepreneur

Designing the future is a journey, not a destination—and Sam inspires us each step of the way. In his Journey, we explore his entrepreneurial beginnings and the lessons he’s learned, teaching us how to thrive in challenging market conditions, the value of decoupling identity from work, and the depth you achieve when bringing full authenticity to your family and your work.

Sidebar: Sam, what was growing up like for you, and did you get any sense of how you fit into the world?

Sam Rosen: My mom is a painter, a very good painter. All the paintings on the Netflix show Grace and Frankie (the longest running show on Netflix) are my mom’s. My dad directed television commercials. I'm a blend between the artistic, expressive, very empathic side of my mom, and my dad who is a very charming, funny, exuberant producer guy.
I grew up in a house with mid-century furniture and books on Japanese modernism, which is funny because that's the stuff my friends are into now. I grew up in this incredibly diverse community and went to a high school where a hundred native languages were spoken. I didn't realize until I was a grown man that’s not everybody's experience. I'm the first Jew some people meet, and I'm like, “I grew up with ten kinds of Jews.” (laughs)

Sidebar: You once wrote, “Since the age of five, you could find me behind my Mac working on my latest scheme to change the world, or at least a large portion of the local playground.” Those are big words, tell me about them.

Sam:  I've always been entrepreneurial. My brother told this story at my wedding that as a kid I would sell rocks out of the back of my Radio Flyer wheelbarrow. But here’s the thing – I would dip half of them in water, and I would charge more for the shiny rocks. I think that sums up my personality really well.
Also, I grew up in a really cool moment in time. When I was five, my dad bought me a Mac, and I remember when America Online introduced the World Wide Web. Since then I've been in this really unique place where people older than me didn't grow up in this digital world, but everyone younger than me did. I've always felt like I’m in this position to be a translator, kind of a bridge between the digital natives and the people who are not. That has afforded me lots of really cool opportunities.

Sidebar: If I've got this right, you've never worked for a company that wasn't your own. Tell me about your intrinsic motivation to create rather than looking for established structure.

Sam: I have really good parents who have always let me do my own thing. My parents were like, “Look, you can be whoever you want, we prefer you're not a lawyer or a doctor.” (laughs) “ But you can do anything else.” My mom is a painter with her own studio, my dad was an entrepreneur, my grandpa was an entrepreneur, so it's in my blood and how I was raised. I've always been really well supported to try new things, to explore, and be okay with failing. I realize this is a great privilege.
It’s funny, these days my biggest fantasy is about working for the man, getting a salary, and not having to fundraise or make big decisions. If I work for a big company, I can learn how other great leaders make decisions. I have this theory that everyone is just making stuff up, especially the boss – the boss is making it up the most. It would be nice to be part of a leadership team that is thoughtful and world-class where I can just learn.

Sidebar: I like that open-mindedness. You've been an innovator in the coworking space before we were even talking about coworking. In 2008, you opened the first coworking space in Chicago, aptly named The Coop (like chicken coop). What drew you to this space, and what's kept you there?

Sam:  So my story here is interesting. The first business I started was a digital agency called One Design Company (which still exists and employs about 50 people). When that business was getting started, I had a girlfriend who lived in Brooklyn. I would go visit every few weeks, and I was running my agency out of her less than ideal garden apartment, with roommates and clothes everywhere and horrible internet and cell coverage. During a kickoff call with our biggest client, I dropped the call like five times, and one of my colleagues was like, “You can't do this anymore, get it together.”
So I did what any self-respecting person would do – I went to the cafe down the street (aptly named The Rabbit Hole), and I would sit there all day with my two coffees and one bagel. And they hated me. One day the internet stopped working, then the power stopped working, and I’m like, “Okay, I’m out of here.”
A friend of mine explained coworking and showed me this wiki that listed the 300 coworking spaces in the world. One happened to be a few blocks away – it was an art gallery that was a coworking space during the day, and it solved my very pragmatic needs – internet and phone that worked. But, more importantly, I met all these awesome people from New York who were in design and media and politics and technology. And they were my people and I was like, holy moly. I fell in love with this concept and this community, and I asked who's doing this in Chicago? And the answer was there was nobody.
So my partner and I at the agency opened the first coworking space in Chicago, and it grew from about eight desks to 70 desks. Ryan Graves, who was the CEO for Uber, was one of our first customers. I became really hooked from that moment on the technology and tools behind how we work and where we work… and I realized this idea of everybody going to the office every day just didn't make any sense! It was clear 14 years ago and it hasn’t changed. It's just that the world has caught up to the idea, which is so cool. So you know, right place, right time… but also sticking with it.

Sidebar:  As a founder and entrepreneur, we're in a much more challenging market than we were 6-12 months ago. What advice would you offer to other founders or creators who are in this headspace with you right now?

Sam: Life is short, and there's only so much you can control. I have kids and some assets and it's definitely scary. I'm out there fundraising and talking to people all day and it's definitely hard. But look at the best ideas and innovations – they come from these times. And there's unbelievable opportunity out there. The best people find that opportunity and thrive in these times. One of the key attributes I've seen in the most successful people is perseverance, just the ability to keep going. I know that in times like these, it's really, really hard to keep going. So my advice is to keep going!
My other advice, which is the inverse to keep going, is knowing when to give up. The most successful people I know are also the ones who can lose a business and say, “Yeah, I lost but I learned a lot, I met some great people, I figured out what I'm going to do next, and I raised my kids along the way.” People who instead of just seeing the bad, find value, let go, and move on. Those are the people who are not just the most successful, but I think the happiest too.
There’s this constant tension between being persistent – and not giving up even when it's really, really hard – but also being smart enough to know when you have to walk away.

Sidebar: Let us all be able to walk that line, Sam. What do you believe are the “must have” qualities of a great leader?

Sam:  I think vision and empathy. Creating a great vision that people can coalesce around, but really recognizing that we're all just humans – we all have good days and bad days and life’s not just about work.
From those core values, it’s crucial to build a great team by surrounding yourself with people who have different perspectives. As a leader, you're just the conductor. Being a leader is not having all the answers and making all the decisions, it's building an environment where people feel comfortable that they don’t have to know everything… that collectively, you’ll sort through it. Leading this way involves being really clear about your goals and also understanding how people are motivated, so that you can coalesce everyone around a shared vision.

Sidebar:  That’s well said. What would you say are your biggest accomplishments?

Sam:  A while ago, I had an investor come into my life who was going to make all my dreams come true. Six months later, I nearly lost everything on the three businesses that I was building. I came home on New Year's Eve to my now wife, in tears, and was like, “I lost everything, I lost it all.” And it was such a pivotal moment because she didn't care at all… because she loves me.
I was so tied to my identity as an entrepreneur that the idea of losing my businesses was like losing my identity. And in that moment, I realized that my businesses are not my identity. I’m proud that I've surrounded myself with good humans who love me and we’re all supportive of each other. I have this beautiful family that I could come home tomorrow and be like guys, “I'm shutting down the business,” and I know they will not give a f***.  I had to learn that, but to know it now is really empowering. I know that as much as I tie my identity to my work that's actually not my best accomplishment. My greatest achievements are my friends and my family. They really are.

Sidebar: That perspective is such a refreshing reminder. Thank you. It seems like that perspective allows the risk of creating to feel… well, less risky.

Sam:  There's so many people who are afraid to take the first step because they don't look at it as stairs. They look at it as a cliff. I have many people in my life who come to me with this idea they’re thinking about quitting their job to pursue. These people are at the precipice of the cliff and they want to jump, they just want someone to push them and say JUMP!
I always say, “What's the worst thing that happens?” The worst thing happens is you fail and you can probably get that sweet job back that you have right now.  I would argue that you will be a better employee (and generally more employable) because you understand the pieces of starting and running a business. So sometimes I feel like I'm just the guy people find to push them off the cliff, and I'm like, “Oh just fall, it's gonna be fine.”

Sidebar: You mean push them up the stairs?

Sam: Yeah. Push them up the stairs (laughs)

Sidebar:  Amazing. So as a member of Sidebar you're committed to self growth and becoming a better leader. What's something you're working on with your group right now to improve?

Sam:  I've always been a people pleaser and a consensus builder, which is great to a point. Sometimes you don't need consensus, you need force and strength. And I’m navigating that blend, because I’m very empathetic and want everyone to like me and be pleased. But I’m recognizing as a leader I’m not going to please everybody all the time, not just in my career but in my life. I'm working on that with my Sidebar group, and they’ve helped me see that more clearly and have given me more confidence in navigating that.

Sidebar:  Interesting. Is there a specific instance where something you took away from your Sidebar group changed the trajectory of your work or life?

Sam: I'm navigating all sorts of interesting stuff with work and my co-founders, and there's been a lot of proof points with Sidebar, showing me I’m not crazy. And that’s giving me confidence in the decisions I’m making. One of the best things about Sidebar is just knowing the problems that I have are not unique to me – any problem that comes up in the group, most people are like, “Oh yeah, I dealt with that.” And I’m like, “Oh, you too have dealt with that? Because my wife hasn't dealt with that, my therapist hasn't dealt with laying somebody off or pitching somebody or having a really tough conversation with a partner. They don’t understand these immense pressures, where you feel very alone.” That's been a huge benefit of my Sidebar group – knowing I'm not alone, and these things aren't uncommon. Knowing other people have tackled these problems and can give you great advice from their experiences is really cool.

Sidebar: I love that, and it's interesting because your sentiment seems like a very common theme across these interviews. I'm curious, what surprised you the most about Sidebar?

Sam: I’m going to answer this slightly differently. What drove me to Sidebar was that I started therapy two years ago, and I realized that a lot of the problems I was really stuck on were work related. Sidebar has provided me a venue to think and talk about these work-specific problems. Being in this community of business people, in a similar place as me, has helped unblock so much, and that’s been really empowering. I didn't realize how blocked I was on some of this work stuff, and having the right audience to talk to has opened up space to work on other things in my life. That's been really useful.

Sidebar: Switching gears a bit. You have a family, and I'm wondering if there's anything you want to add to the idea of navigating career growth with a family?

Sam: I think cultivating deep vulnerability. That’s where I’ve had the most intense growth in all of my relationships, including my wife and family. Creating an environment where you’re comfortable saying, “Hey I'm struggling, I’m uncomfortable,” that's where the magic happens.
Also as a dad, instilling in your kids that they have the space to figure out who they want to be and what they want to become. And that they’re comfortable making mistakes and saying the wrong things. I implore people to be vulnerable not just in family but in work.

Sidebar: With someone who's achieved such objective success as a creator their whole life, where do you draw the inspiration to keep going?

Sam: I love the idea of the more I see the less I know. I'm a very lucky human being – I've gotten to go all over the place, I've gotten to meet all sorts of amazing people, and the more that I see, the smaller I feel, which is really empowering. That dynamic has always encouraged me to keep learning and keep trying, and that’s fun for me.

Sidebar: What's the hardest thing you've ever said no to?

Sam: Sometimes you have to let go of things before filling them back up – I've had to say no to things when I didn't know what was going to replace them. That's really really hard but if you're just waiting your whole life for the next thing to appear so you can transition safely, you're going to be waiting a long time and that thing may never happen. But being able to let go of things and create emptiness… that's where the cool stuff happens. The universe will fill up that empty space, but you have to make the space first. And that’s hard to do if you don't know what's coming next.

Sidebar: I love that. Any last thoughts that you think people could benefit from?

Sam: I will leave you with my favorite motto: “Luck is the residue of design.” The luckiest people have the most success, and there’s definitely genuine kismet involved, but it's not an accident. The most successful, smartest people are in the room for this lucky thing to happen. They made the right choices to get closer. You cannot create luck, but you can certainly put yourself in a position to be more likely to get it. That’s one of my little guiding principles to how I approach the universe, which my dad taught me.

Sidebar:  That’s so good. I’m leaving this conversation feeling very inspired. Thank you Sam.

Sam:  Thanks yeah, I'm excited too.

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