From real estate and hospitality to music, art and culture, these six Chicago men are finding big success by blazing their own trails.
(Photo by Paul Octavious)
With more than a half million Instagram followers, 34-year-old photographer Paul Octavious has proven his star status on social media. But the Connecticut native isn’t resting on his name: “There’s a life out there to live, so that’s what I think is important for me—to work on projects that are not Internet-based, that are actual reality.” He’s realized that as founder of Eye Eaters Society, a series of roving pop-up dinner parties that toasts the relationship between food and art. A hit since its inaugural sold-out session—where chef Edward Kim of Mott Street plated dishes inspired by Octavious’ work—the initiative has since graced the MCA and other hot spots both inside the city and out. Says Octavious, “With Eye Eaters, I can walk away from the Internet, breathe and work on something I can get my hands dirty with.”
(Photo courtesy of Cedar St)
The Chicago skyline beckoned Alex Samoylovich early on. “I got interested in real estate at 19 or 20,” recalls the Skokie native and former trader. “I thought it was fascinating to be able to own buildings, especially architecturally significant ones.” He’s realized that youthful ambition as head of Cedar Street Companies (co-founded with the late Jay Michael), innovating Windy City real estate with pioneering concepts like FLATS, the lifestyle-driven brand proffering chic rentals in a “live, work and play” setting. Critical to his success: a focus on adaptive reuse that transforms underperforming properties into modernized developments, perhaps most notably in Uptown. It’s an approach guided by a nobler ethos: “Our goal is not to buy and flip properties,” says Samoylovich. “We’re identifying historic or landmark structures and bringing them back to life. By doing that, we have an impact on the community.”
(Photo by Emiliano Granado/Courtesy of Charles Adler)
Most people know Charles Adler as the co-founder of Kickstarter. But the 44-year-old entrepreneur has moved on, bringing to the city his Lost Arts concept—a platform for creators to realize projects in technology, arts and design. Test-driven in 2015 as a month-long pop-up, the workspace was filled with prototyping tools, 3D printers, table saws and sewing machines, and gained real buzz. So Adler opened a larger, temporary version on Goose Island with an accelerator program, event space, prototyping lab “and even WiFi,” he jokes. In 2019, Lost Arts launches a digital platform and relocates to a new location TBD. Says Adler, “I love that Chicago is an immensely creative city with amazing incubators and fosters ambition in a lot of different capacities. Hopefully, as with Kickstarter, we can help makers of tech and arts reach a larger audience than they could on their own.”
(Photo by Michael Apostolos/Courtesy of Haight Brand)
Chance the Rapper is as much a maverick off the mic as he is on it, famously eschewing major labels to remain independent. Key to his ascent: Sauganash native Pat Corcoran, the manager who’s been at his side for the artist’s breakout moments, including onstage at the 59th Annual Grammy Awards, where the rapper netted multiple honors. “Peering into the crowd and seeing my parents in tears—I cherish that as much as winning the actual Grammys,” recalls Corcoran, who co-founded talent agency Haight Brand in 2010. The 2017 Forbes “30 Under 30” honoree also recently launched No Fine Print Wine in partnership with Lettuce Entertain You wine director Ryan Arnold and fellow talent manager Tim Smith. Suggests Corcoran of his success: “I believe the little things done well equal great and big things. I focus on the little things more than the average Joe.”
(Photo by Marcin Cymmer/Courtesy of Parker Restaurant Group)
Some of Brad Parker’s earliest memories are of family vacations to Naples, Florida. “We used to eat at Tommy Bahama,” says the 35-year-old, “and it had this cool vibe even though everyone was older.” After he sold his first restaurant in 2012, Parker spent time thinking about American vacation spots and how Chicagoans use clubs for urban mini-breaks. So in 2015, he opened Hampton Social, inspired by the breezy affluence of Montauk, New York. The beach-themed boite's instant popularity blew Parker away. “We thought it would crush in the warm months, but it stayed strong in the winter, when people really want to escape,” he recalls. Hampton Social has since grown to three locations, with six in the pipeline through next year. “Our goal is to make our restaurants synonymous with a social destination, especially for girls’ nights out and brunch,” he says. Leave it to a guy with five sisters to devise a dining concept around what women want.
(Photo by Allison Michael Orenstein/Courtesy of Brendan Fernandes)
When Brendan Fernandes left his adopted home of New York City for Chicago, he wasn’t sure what to expect—maybe that his art career was over. Flash forward two years, and the Northwestern Art Theory and Practice prof has earned a solo show at DePaul (through December 16), a 2019 show at the MCA and collabs with the Joffrey, the Graham Foundation and EXPO Chicago. “Chicago allows me to take ideas I’ve been pondering and make them happen through my new community,” says the 38-year-old trained dancer, whose latest work, The Living Mask, explores post-colonial history. His performance pieces are interdisciplinary and hard to define. “I’m a fifth generation Kenyan Indian raised in Toronto who lives in the US. You can’t look at me and put me in a box.”