Chicago Social: Sam Cushing Takes the Windy City into the Influencer Realm

Sam Cushing

Kanye West. Jennifer Hudson. John Cusack. Barack Obama. Chicago has generated its share of people who emerge as national figures. Our city, however, is weak on the social media scene. Local boy Sam Cushing is changing all that. A native of the Chicago region and sometime city resident, he has amassed a major following on YouTube and Instagram. With a blend of content ranging from LGBT topics to fitness to mental health to a burgeoning music career, Cushing has put the city on the map in the social space. Starting out on Instagram when he was living in South America a scant three years ago, Cushing has expanded his range to YouTube with videos that discuss his experiences and offer advice on everything from exercise routines to travel. Cushing is at the vanguard of a new brand of influencer: socially aware but relatable and sweet. No sanctimony or lecturing. Yes, he does brand partnerships, but in a conscious and thoughtful way. He discusses his struggles as a gay man who deals with anxiety, but keeps things entertaining and light. And he’s left the door open for other topics. His reach is such that the tourism board saw fit to name him as an ambassador to the city last year. Cushing may have gone international but he retains his affection for and fascination with Chicago.

Where did you grow up? What was your family situation?

I grew up in the suburbs of Chicago, twenty-five minutes west of the city, with one older brother in a broken family. My parents divorced when I was in fifth grade. So I was splitting my time, running around the Chicago area staying with both sets of parents. Both of my parents are remarried. I went to Hinsdale Central and was senior class president. And then I went to University of Illinois. So I spent a majority of my life in and around Chicago. Then after I graduated with a double degree in business—supply chain management and marketing—I started my career as a consultant, full-time at PricewaterhouseCoopers.

I was there for two years. The first year, I was in Manhattan. And then the second year I was living in Chicago, which was just the best experience ever. I was living with my best friend. We were right there on the Lake, right on Lake Shore Drive. It wasn’t the nicest place in the world. But it was such a beautiful location. To wake up every single day and see Lake Michigan. It was just stunning.

You’ve talked on your channel about coming out. How was growing up as a gay kid in the Chicago area?

It was a mixture. As compared to a lot of my friends and a lot of other coming-out stories I continue to hear, I was relatively fortunate. I didn’t run into too many hiccups within my family. My mom actually asked me if I was gay when I was about fifteen. I had already come out to my best girlfriend that same year. I told my dad the following year. It’s sort of a funny story. I told him in an effort to get out of a grounding because I’d come home really late. I was in my sophomore or junior year of high school at this point. It was summertime and I really wanted to go to the Pride Parade the next day. I was like, “Listen, dad, I know you’re mad at me, but I have something to tell you.” And he was like, “Okay, you can tell me anything.” And I came out to him and got out of my grounding. It was a pretty smooth coming-out story.

The only real issue that I had when I was in high school. I dealt with a lot of bullying and teasing and stuff like that. Mostly speculation of whether or not I was gay. There was a Facebook group that was created called “Sam Cushing = Big Fag.” Of course I panicked. That was the year I was still kind of unsure. You’re so young at that age, and you don’t really have any frame of reference. So it was tricky. Ten years ago, being gay was synonymous with being disliked. “Oh, that’s so gay.” “This is gay.” It was a negative thing. I didn’t want to be disliked. I grew up in Oak Brook. The schools were a lot smaller and filtering into Hinsdale Central, which is a really large school district, I was the new kid on the block. There were all these rumors swirling around and then that group came out. I reported it. A week later, [the guy who created the first group] uploaded another group: “Sam Cushing = Big Fag 2.”

My friends and I have been able to laugh about it in a strange way. The first few years of high school were kind of rough for me. I had social anxiety. My parents were going through a nasty divorce and I was just coming out. There was a lot that was happening all at once. But then I kind of came into my own. I have a really strong family support system from an LGBT standpoint, and my friends are always supportive. I actually started going out my senior year of high school—very, very young—to Boystown and meeting other gay guys.

Your early career was in the business world. What led you down that path?

I was being risk-averse, honestly. I had a dad who was big into business. He was VP of marketing in his company. So that played a role. You look up to that when you’re growing up in terms of what you want to do with your life. My brother followed in those footsteps. I just set the path of what felt like least resistance, felt the most safe and secure from a financial standpoint. I spent four years in high school prepping to get into University of Illinois, the College of Business, four years in college, working my butt off [and then graduated] cum laude. I was very involved on campus with all sorts of business consulting and business fraternity organizations. I landed a few pretty awesome internships after my sophomore and junior year. So my senior year it was nice because I was just coasting. And I already had secured a full-time offer at PwC.

Were there other moments that made you think it wasn’t for you?

You know, being gay, I think that played a factor as well. That led me to know that traditional corporate America wasn’t the right bet. I followed my brain and not my heart. I didn’t feel like I was living a life that was authentic to me. I don’t let being gay define me. There were so many other parts of me that just didn’t fit in. I didn’t fit in with the culture of sitting behind the computer screen for eighty hours a week without talking to very many people and feeling like a cog in the wheel and just a number. It wasn’t for me and I felt disillusioned by all this corporate Kool-Aid that I was drinking. It’s not to say that all those jobs or companies are bad. They’re great places for certain people. I don’t think it was a cultural fit for me.

You’ve discussed how that was a very conservative environment. Did that start to bother you at a certain point? I remember you saying you got reported to HR for not wearing an undershirt. Did you ever find out who did that? How did that conversation go?

Yeah, we did have to have a conversation. I don’t want to call it discrimination. It was odd. It did feel a bit targeted. I didn’t have an undershirt on and I guess between two of the buttons, you could see a tiny little bit of skin. I caused a ruckus and made some men uncomfortable and had to have a discussion.

When did you decide to go to South America? Was there a reason for picking that destination?

I ended up in a situation where I was really unhappy. I spent two years working [at PriceWaterhouseCoopers] and I met some incredible people. I have the utmost admiration for my former colleagues. It just wasn’t the right fit. So two years in, I quit. I left it all behind. I booked a one-way ticket to South America, a part of the world I’d never been before. I didn’t know a single person.

I tried to kind of rediscover myself and gain an international perspective. I ended up staying down there a lot longer than I intended. I only meant to go down there for about six months. I ended up staying for two years. And while I was down there, I improved the social media following that I’ve been able to turn into a full-time career.

I knew that I wanted a large city and I wanted a progressive city. I had studied in Madrid back in college and I absolutely loved that experience. And it was eye-opening for me. It was so culturally immersing. I wanted to replicate that but not in the same place. So I just did a bunch of research and Argentina quickly floated to the top of my list. [Being in a] Spanish-speaking city was really important to me. I wanted to become bilingual. I did, which is pretty cool.

It’s unfortunate because their economy is in shambles. They’re not in a good spot economically, but culturally it is so diverse and so interesting. The topography down there is just insane because you have desert, arid, mountainous regions to the north like Jujuy and then if you go down south to Patagonia, you have the entire coastline, which is gorgeous. There’s just so much to do and so much to see. Argentina is unlike a lot of other countries in South America in that it has very heavy European influence, specifically Spanish and Italian.

From an architecture standpoint, when you’re walking around, you see how opulent the city once was. Back in the 1930s, or forties, it was the fourth-wealthiest nation in the entire world because they were exporting so many resources. Then through corrupt politicians, it completely tanked. You see these beautiful buildings [that are now] just decrepit. There are parts where there are trees growing out of the buildings. It’s just such an interesting dichotomy.

What did you do for work?

I found work at a tech start-up. I was working in marketing sales for about a year. They moved me to Medellín in Colombia, where I spent another year. I was heading up an office of seventy engineers. I was in the tech world and I discovered a love for that culture. If I ever went back to a typical nine-to-five sort of position, it would definitely be in tech just because culturally it is more aligned with my personality. But simultaneous to that, I was beginning to grow my social media presence because I was traveling a lot. It was kind of fun to see this American boy traveling around and trying to fumble through his Spanish and figure it all out.

What led you to documenting your adventures?

Everything I was doing was in Spanish. My relationship was in Spanish, all my friends, everything was in Spanish. It was nice to connect with people back home in English. It was also for other people to be inspired to live a life that feels more authentic to them. That’s always my message, which is to be like the you-est you that you can. But just as much as it was for other people, it was also a very personal way to document and imprint this time in my life, for me to reflect back on. I learned so much about myself when I was down there. It was nice for me to be able to go back and be able to say this is what I was doing December 21 two years ago.

When did you start your YouTube channel?

Instagram has always been my core. My YouTube channel actually is fairly recent. When I decided about a year ago to make the move back up to the States, I made the decision to do social media full-time. In doing so, I decided to launch my YouTube channel. So I really have only had the channel for about a year, which is pretty cool considering that I’m coming close to 200,000 subscribers. I just received my YouTube plaque from Google for crossing that milestone.

How did you decide what kind of content you were going to post? When did you decide that you could monetize this through brand partnerships?

The pandemic hit soon after [I got back] so travel went out the window. There were always a few other themes in my content, one of which is fitness. Another one was wellness—health and nutrition. Music was my fourth pillar. I just decided to double-down on the latter three.

I had a few friends who were in the content creation space and they really sold me on [the brand partnerships]. It’s a bit scary because I came from such a conventional background. I had my life pretty mapped out for me. Going to business school, everything was very step-by-step. In that world, you work toward your next promotion, and you work for another promotion, and it just continues on and on. The social media world was very foreign to me. Especially growing up in the Midwest, entertainment, media, social media are just not as prevalent as they are for some of my friends in L.A. or New York.

For the first few months, I was earning nothing, which was totally fine, because I really enjoyed doing it. I luckily had a bit of savings. When I moved back to the States, I moved in with my family for a little while. So that was hugely helpful. I’m very fortunate in that respect that I’ve finally gotten to that place [where I can make a living].

I want to make sure that I really believe in the brand and believe in the brand mission. I don’t want to become like an advertisement for any company that offers to pay me.

When did you get into fitness and discover you could make money in that sphere?

My older brother got me into it. He was your typical jock growing up, which is the antithesis of me. We always bonded over it. I just felt so much better about myself after leaving the gym, not even from a superficial standpoint of wanting to look good, where you fill out your clothes nicely. It was really internal. We always felt really good about ourselves. So a lot of it for me is wanting to share that with other people.

How do you go about deciding on your partnerships? What are you comfortable promoting?

Typically, there’s an inbound strategy and an outbound strategy. There are a lot of brands that will approach me. If I haven’t already used the product, or I’m not familiar with them, I’ll request that they send it to me, and then for a few months, I’ll try it out. There have been a lot of different brands that I turn down. I don’t believe in it, I didn’t love the product, it didn’t feel worth sharing. I’ll look at corporate responsibility, on who they are as a company, what they stand for, who they donate to. Things like that are important beyond just the product itself. I would never work with a company that has historically very anti-LGBT policies. Then there are other products that I just genuinely use in my day-to-day. I’ll reach out to them, like Hey, I love your stuff. I’m happy to engage. It doesn’t even have to be some kind of contrived [situation]. Even if there is no monetary benefit to that, I believe in them as well.

How do you decide what to share and what to reveal when you talk about personal things?

It’s a scary thing when you share something that publicly, because one thing I’ve learned this year is that our parents were right. When you put something out on the Internet, you can’t come back from that. So you really have to commit. It’s a commitment for life. I think it’s a matter of striking a balance. There are certain things that, out of respect for people in my inner circle, I wouldn’t want to necessarily reveal to everybody. But if it’s a story that I genuinely think will help other people and I feel like the impact is there, I enjoy being authentic in that way. For example, I came out with this video [where I] talk about my anxiety, which is something that I’ve struggled with for a long time. I used to have a bit of a facial tic. It was a manifestation of my anxiety and it would ebb and flow. Even to this day, I still sometimes struggle with that. I thought that in honor of Mental Health Awareness Day, what better time to share my story and help somebody else who may be going through something similar? I think it’s about how I can impact other people.

What are some of your quintessentially Chicago activities?

I did a partnership with Choose Chicago, which is the official tourism agency, to promote the city. They hosted me for a little staycation. I created this video, “Top 8 Things to Do in Chicago.” A lot of the people who follow me have probably never been to Chicago. So things like the Signature Lounge up at the top of the Hancock, Millennium Park, the Riverwalk. I put Sea Dog on there as well as part of your Navy Pier day. Things like heading to Uptown and checking out the Green Mill Cocktail Lounge that has this whole mobster history, where there were these underground tunnels in that part of the city where Al Capone would escape if the police raided the bar.

I’m such a Chicago fanatic. I read all sorts of literature on the history of Chicago. My friends always laugh at me because I’m the king of Chicago fun facts. Anytime we’re walking around the city, I always know weird, quirky facts about the architecture or the history or the food thing that Chicago was really known for. So it was fun to work with that piece of content.

I mean, there are seventy-seven neighborhoods. Every single one has its own individual flare, which is really interesting. I lived in eight different cities in the last eight years, which is really cool. But I always tell people—of course, I’m biased because I grew up in this area, but—as many flaws as Chicago may have, I think that it’s the best city and the most beautiful city and it’s so stunning.