Matthew Manning is a man of the world — and his mission is to change it. Early this year, the 26-year-old from Sweden debuted Royal (Royalbeings.com), a multimedia platform that uses various forms of storytelling to celebrate and strengthen black culture.
“[I had] felt my priorities shifting for awhile,” he says, noting that his girlfriend and co-founder, Courtney Phillips, was having the same experience. “Living as black Americans in such a racially polarizing era, and seeing and feeling the discomfort and lack of security we feel simply by being ourselves, despite our privilege, despite the community we live in — it was harder and harder to ignore. [We felt] we weren’t fully celebrated or represented, or even could be ourselves fully in any of the spaces we occupy. … So Royal emerged from both a pain and a grief, as well as a gap, something we recognized was missing.”
By mid-summer, Royal will roll out an online journal called Unbound, a magazine, podcast channel, social media campaign and visual media project, each populated by submissions from around the country and world, and curated by a group of volunteer editors. Manning’s goal: for Royal to be the next VICE Media, which began in the ’90s to give voice to the underrepresented fringe culture and is now a multibillion-dollar company. “It’s a huge vision,” he admits, “and it’s intentionally broad. It’s national and expansive, because that’s the only way to create the community we’re hoping to create.” He’s working without compensation for the time being — while also getting his masters in writing and publishing — to achieve that goal.
“My daily motivation is to bring more joy, to bring more light into the world,” he says. “For people to know their power and their worth and their value, and to know that they’re seen and heard.”
Brandon Phillips knew he wanted to mix drinks since, well, before he could drink. “My older brother is a sommelier, and he’s 11 years older than me, so I grew up with a respect for spirits and wine,” he says. “In high school, I wasn’t the kid trying to pound a 30-rack of Miller Lite — and I probably wasn’t the most popular for it, either — but I always had a respect for and wanted to drink cool beers and good wine.”
Upon moving to Chicago five years ago, Phillips, 30, apprenticed under Charles Joly at The Drawing Room before opening Rockit Ranch’s Bottlefork — and later The Duck Inn — alongside Chef Kevin Hickey; last year, the Chicago Tribune named him Bartender of the Year. Now he’s working on the cocktail program for Otto Mezzo, Rockit’s new spot opening this spring in the former Ay Chiwowa space.
“[Every drink] starts with an inspiration,” he says. “At Duck Inn right now there’s a drink that was inspired by watching leaves fall and wanting to capture that feeling. We use as much nostalgia and storytelling as we can; we like to think of our drinks as being transportive, with the idea that they could take you to a either a memory of your own, or to a different time or place, somewhere you’ve never been.”
Despite his creative laser focus, Phillips is a live-in-the-moment type. “I tend to be along for the ride as much as I’m making the ride happen,” he says. “In five years I’ve jumped leaps and bounds beyond where I thought I would be, and I’m by no means done.”
Friends since they were teenagers, this group has always helped each other out with their respective businesses: Regalado owns a commercial cleaning company while Oviedo and Santo — along with brothers Joey and Nick Santo — have a successful Back of the Yards screen printing company called Culture Studio.
The group’s latest venture was born — as the best ideas often are — out of a need they saw within Culture Studio, for a cloud-based software that streamlines the screen-printing process, from communicating with suppliers to working with artists and packing and shipping orders. The guys teamed up with Matt Gierut and Keval Baxi from tech development company Codal and Stokkup was born.
Culture Studio used the software internally for nearly two years, getting the kinks worked out before opening it up to the market this year. Now, Stokkup has four clients using its software, and there’s potential for many more. “In the United States alone, there are about 50,000-60,000 printers that would be our target market,” Regalado says. Adds Santo: “I see Stokkup being the system that finally unites a classic industry.”
For now, the group is working out of startup hub 1871 a few days a week, while continuing to run their other businesses (Regalado also has plans to launch an on-demand housekeeping app, Ask Roza, later this year). The group of 30-somethings are entrepreneurs at heart, and their goals are anything but selfish. Each hopes to create jobs and give back to the community through the success of Stokkup and other companies. “What motivates me every day,” Oviedo says, “is the overwhelming opportunity there is to disrupt and teach.”
“I’ve probably made every mistake you can,” says John Roa, a West Looper from Grosse Pointe, Michigan, who at just 33 has been an entrepreneur for almost 20 years. “I’ve been broke, I’ve had a lot of failed businesses. I had very little to fall back on if things didn’t go well, and so it forced me to only take on things that could help change that situation. I had to give up on a lot of things people take for granted — friends and personal relationships and fun and a normal college life — to achieve my dreams.”
It was worth the grind. In 2015, Roa sold his most successful company, tech consulting and design firm ÄKTA, to Salesforce — and the payoff put him in an ideal entrepreneurial position: “These days,” he says, “I have the ultimate luxury of being able to pick and choose whatever is exciting and invigorating and interesting to me, and not have to work on anything [that isn’t].”
Among those projects, which he handles through his holding company, Roa Ventures: He’s building villas in Greece, investing in fashion labels including the Chicago-based Ellison eyewear, writing a book and opening a members-only cocktail bar later this year in Chicago. He’s fielding pitches constantly, for tech startups and movie scripts and dozens of other things; this year alone he’s invested nearly $5 million into various projects — and it’s only March.
“I just love the business of business,” he says. “I love seeing something go from what might be an idea or a random thought or even a dream, [to] a thing that you’re selling or people are experiencing. That ability to create is what keeps me going.”
Ever since he started making music, Na’el Shehade’s career has seemed pretty solid: He licensed his first song and started a studio at 17; by his mid-20s, he was producing songs for artists like Chance the Rapper and Kanye West. But all was not as it seemed.
“I was working with a $1 million budget [for a record label] at 25 years old. [But] my life was in shambles. My dad was [sick] … I was traveling from LA to New York to Chicago; my girlfriend left me. But that’s what makes for a great artist or great producer or businessman — you have to go through these challenges that are basically [telling you] you’re not meant to do this. You have to fight it, and that’s what I did, I fought it.”
It all got him where he is now, producing the music he wants to produce: his own. As part of the duo Drama with singer/songwriter Via Rosa, Shehade, 29, is producing what he describes as “emo dance music.” “I write the music and Via writes all the lyrics,” he says. “It’s about her life, about her breakups. My music is very dark, so it fits hand in hand.”
It turns out, following your passion works. Offers are rolling in: SoundCloud paid for Shehade and Rosa to fly to Austin and perform at South by Southwest, they’ve licensed two songs for upcoming films, and they’re in talks with retailers like Starbucks and Anthropologie to have their music played in stores.
“In order to make music you have to have an open mind,” Shehade says. “You deal with different styles, different people, different lyrics, different emotions. … To see people sing your songs and to get emails saying ‘this song got me through whatever [struggle]’ — it’s an amazing feeling.”
Rob Rose is not your typical businessman — the organization he leads, the Cook County Land Bank Authority, fills a community need with a deep social purpose. The CCLBA reclaims distressed properties and cleans them up — both physically and financially — to make them desirable for new buyers. It may not sound sexy, but in the next decade it could quite literally change the landscape of Chicago, and as executive director, Rose is the force behind that change.
“My driving principle is equity,” Rose, 46, says. “A kid’s future shouldn’t be determined by the zip code in which he’s born, right?” Rose has made it his mission to clean up those affected parts of Chicago — places like Washington Park, South Shore, Chatham and others.
“In a healthy market when a house is vacant, two or three people may put in an offer,” Rose says. “But [in] a lot of these neighborhoods, a house goes vacant and it may be 10 years before someone tries to reoccupy it. So we’re going in there” — paying off back taxes, fixing code violations — “and facilitating a transfer to someone who can rehab it or someone who wants to live in it.” In 10 years, he says, “we want to see an equitable distribution of investment around the city, instead of the winner-and-loser pattern of investment we have now.”
Since its formation in 2013, the CCLBA has acquired nearly 500 properties and created more than $8 million in community wealth.
Rose’s motivation is simple. “It’s my turn to make a contribution,” he says. “I have a pretty unique set of education and experiences to bring a lot and to grow, and here’s what I can do to make things better.”