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A woman smiling holding a platter of chocolate.
Chocolat Uzma was among the beneficiaries of DishRoulette Kitchen.
Barry Brecheisen/Eater Chicago

DishRoulette’s work isn’t done as restaurants continue to struggle

After the city of Chicago handed Carmen, an immigrant food vendor in Little Village, over $1,000 in citations for operating without a food license, she turned to DishRoulette Kitchen’s Jackson Flores to guide her through the bureaucratic process.

With Flores acting as her translator, Carmen’s violations were reduced to $200 after he helped her “negotiate with the city to bring the cost of tickets down by proving that she was working with us to obtain up-to-date licensure [sic],” he says. It was a lesson — albeit a costly one — on operating a food business in Chicago.

Flores is president and co-founder of the restaurant development center DishRoulette Kitchen — a spinoff of tech company DishRoulette — which provides financial assistance to small, independent businesses owned and operated by women, people of color, and undocumented entrepreneurs. DRK is a much-needed bridge between under-resourced food entrepreneurs and the capital, knowledge, and proper business relationships needed to help keep their businesses afloat, with the long-term strategy to make them profitable.

“I’m a first-gen Guatemalan American and if it wasn’t for a handful of entrepreneurs in Albany Park, I wouldn’t be able to get Guatemalan food anywhere,” says Flores. “If [those food entrepreneurs] didn’t pick up that mantle, I wouldn’t know where to connect with that piece of my culture. There’s so few entrepreneurs that come and have access to resources to be able to start and own their own business; we hope to change that.”

Flores and her team want to give food entrepreneurs, who often trade on their culture and identity and are unaware of the bureaucracy required to monetize it, the knowledge they need to navigate the complexities of owning and operating a food business. Flores, along with Brian Soto, Hector Pardo, Estelle Lozano, and Sany Nguyễn, make up the leadership team. The collective boasts expertise in hospitality, law, accounting, and marketing, among other skills — a valuable knowledge base at the height of the pandemic.

“If people didn’t have themselves set up in the eyes of the city, and state, and a legitimate business license tied to an [employee ID] number with a business bank account, they were just not getting those [financial COVID relief] opportunities,” Flores says. “We started seeing businesses closing down. It happened really quickly, [and that’s] when we decided that we needed to do something.”

DRK launched its first round of funding via Instagram in 2020 with $500 grants. Since then, DRK has awarded more than $75,000 to local small businesses as part of the DishRoulette $1K Campaign, a capital support program for local entrepreneurs left behind by traditional economic relief programs and capital options. They also provided more than $150,000 in professional service hours and education to entrepreneurs on topics ranging from accounting to marketing and communication.

But community-based funding is not why founders Flores and Soto went into business together.

DRK began in 2019 as a food industry tech company called DishRoulette, which offered free social media consulting for restaurants. With COVID lockdowns, the company also kept restaurants connected with social media influencers while helping both parties.

That’s when Veronica Aguilar, former director of the Latinx Incubator at 1871, an entrepreneurial tech hub, met and selected them for the incubator’s exclusive cohort. She remembers how their individual experience impressed her and how well each founder complemented the other.

“They had a really unique and ground-level perspective on how local food concepts could leverage their popular food items,” Aguilar, now an advisor to Flores and her team, says.

DishRoulette had already established a popular food Instagram account with more than 30,000 followers. So expanding its reach seemed like a natural progression. When the pandemic hit, the team pivoted to build DRK, a direct response to the community of food entrepreneurs struggling because of their exclusion from economic relief programs and resources they needed to navigate the pandemic. Traditional restaurants were already struggling to get government aid. Politicians and bankers didn’t know how to help this new breed of small-business owner. Lawmakers haven’t grasped how to write measures to include new businesses (food trucks, for example, in Chicago’s case). Bankers don’t know how to extend their credit — PPP showed that by requesting past financials as part of loan applications. New businesses couldn’t demonstrate a need for money, and therefore many couldn’t qualify for financial aid. For example, a restaurant that opened in the past year doesn’t have financial records from two years ago.

“The work DRK is doing is critical because it’s not only providing immediate financial relief but has expanded to providing financial and operational educational programming,” says Aguilar. “They are building relevant programming and targeting the real pain points for these food entrepreneurs.”

“I’ve never met a more down-to-earth [group] of people who just want to help grow small businesses and ask for so little in return,” adds Cristina Hernandez, a DRK recipient and founder of Tart Pie.

The pandemic showed gaping holes in the societal fabric for people of color, and undocumented and immigrant workers. Consumers were happy, if not eager, to fill the gap in 2020.

“You saw the influx of community-based initiatives everywhere, free meals, free PPE for groceries but I can’t tell you where those programs are now,” Flores says. “The compassion from the early days of COVID has dried up. I hate to say it this way, but people have 100 percent moved on because the world is open again.”

Like many community-based organizations, Flores has the knowledge, access to community, and solutions to address problems at the ground level. She was working in operations as a mid-manager at the members-only University Club of Chicago when the pandemic hit. Her hospitality career includes time at former Michelin Bib Gourmand restaurant Quiote and sister bar Todos Santos, as well as B&B Hospitality Group (co-founded by disgraced chef Mario Batali). The biggest challenge lies in accessing capital to expand reach. Without it, the responsibility of serving these under-resourced communities relies on Flores and her team sleeping less, working more, and having costs come out of their own pockets. Self-funding and long hours to meet demand can be a short-term fix, but it’s not a sustainable solution. The possibility of burnout looms but Flores presses on as the team fights for their own access to capital to ensure they can continue their work.

“We’re currently sitting on a match grant right now,” says Flores. “A community trust said, ‘Hey, here’s $100,000 that you can unlock as long as you’ve matched $100k.’ So we’re in a race right now. We are at 60 percent of our goal and it’s very slow-moving. But we turn every rock over where we can [to meet that goal].”

A $100,000 gift can accomplish a lot for a grassroots organization, but it’s relatively small in the world of charitable giving, where million-dollar gifts exist.

But the DRK team and community aren’t wasting time thinking about what they don’t have. They’re working to turn small amounts into big businesses. The seed money from the DRK $1K Campaign led home cooks to experiment during the early days of COVID. That kitchen tinkering helped launch full-service restaurants like Birria Ta-Ta-Tacos, Tart Pie, and Zeitlin’s Delicatessen — all still serving Chicago diners today.

“This is a stressful job,” Flores says. “There’s times when people find us and it’s too late and they’re closing their business. We have a few DRK $1k recipients who have gone on to close their business, ultimately, because we just got there too late.”

Even Superman can’t save everyone, a bitter pill for Flores and DRK. Even with the holidays approaching, traditionally a time when donations begin to roll in for nonprofits, DRK’s future is clouded. But the team remains prepared.

“I don’t know what’s going to happen next, and we’ve accepted anything can happen,” Flores says. “We are prepared to continue the work. We’re still passionate about what we do, even though it’s not popular anymore. There’s so much importance in business ownership, and not just to the communities in which those businesses are found, but the preservation of culture, through ownership of food.”

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