DishRoulette Kitchen: Empowering Chicago’s entrepreneurs for generational change
The DishRoulette Kitchen team gathers by a communal table originally from the first restaurant they worked with. Crafted now into a conference table, it remains a symbol of DRK. Credit: Jesus J. Montero
Jesus J. Montero is an award-winning journalist and passionate storyteller. He's known for his investigative work covering social justice, music and culture. Jesus J. is also a producer, curating dynamic experiences that highlight culture through storytelling and dialogue. You can follow him on Instagram at @JesusJMontero. Photo: Olivia Gatti
Community is power. That's the driving force behind DishRoulette Kitchen, a support hub for local food entrepreneurs in Chicago's Pilsen neighborhood.
DRK was born in 2020, at the height of the COVID-19 pandemic. It started with an observation from Brian Soto, an accountant who saw firsthand how many of his small business clients were ineligible for government relief programs because they lacked the necessary paperwork or tax documentation. So many of these businesses were shut out of crucial government funding," explained Chris Cole, DRK's director of partnerships and communications. Brian realized that this wasn't just an issue for his clients, but for small businesses across Chicago."
Brian partnered with Jackson Flores, and together they founded DRK to address these challenges. The goal was simple: to provide grants, coaching and the financial and operational expertise small businesses needed to survive - and thrive. From helping businesses manage their taxes to offering guidance on rent and payroll, DRK has since become a lifeline for many local entrepreneurs.
We're scrappy," admitted Jackson, DRK's executive director. We bootstrapped this entire thing, and we're going to keep making it happen, no matter what, because the people we serve deserve the chance to thrive, to create the life they've always dreamed of."
Support for real-time challenges
When an entrepreneur comes in with a problem, we create a roadmap to turn that into a success," explained Brian Soto, director of finance at DishRoulette Kitchen. Credit: Jesus J. MonteroEach member of the DRK team brings a wealth of experience, including from the corporate, finance, tech and hospitality industries. Now, they're applying those principles back into the community, giving entrepreneurs the tools they need to succeed. Since its inception, DRK has created a space where self-made entrepreneurs can tap into that corporate expertise and gain the resources they need. The team offers tailored workshops, consultations and one-on-one coaching.
It's not just about the business. It's about the whole person, the family, the community," said Hector Pardo, DRK's director of strategy and operations. When we see one of our entrepreneurs thrive, it's like popping a bottle of champagne. We're in this together, and their wins are our wins."
For many on the team, this work is personal. DRK Program Analyst Melissa Villalba grew up watching her parents' small business struggle. She knows firsthand how a resource like DRK could have transformed their experience. Our parents came here with nothing, but they made it work," Melissa said. That's what inspires us - to see what's possible when you have the right tools and support."
DRK tailors its guidance to meet the real-time challenges its entrepreneurs face. When an entrepreneur comes in with a problem, we create a roadmap to turn that into a success," Brian explained. The team adjusts their lessons as needed, evolving alongside the businesses they support.
Going digital and beyond
Each member of the DRK team brings a wealth of experience, including from the corporate, finance, tech and hospitality industries. Credit: Jesus J. MonteroA key part of that evolution is helping entrepreneurs build and maintain a digital presence, which is crucial in today's marketplace. A digital presence is everything for small businesses now," Chris noted. We help them not just set up websites, but actually understand how to track their traffic, engage with customers online, and manage sales. We walk them through it one-on-one because too many small business owners don't get formal training in these areas, and they need someone to show them the ropes."
DRK's impact goes beyond just small businesses in Chicago. They've worked on national partnerships with major organizations like the James Beard Foundation, and even collaborated on a project with Bad Bunny. But their heart remains rooted in supporting local entrepreneurs.
We've done so many iterations of what we're doing now, and it's finally starting to get the attention and support we need," Jackson added. The team's diverse leadership is building not only businesses but also a legacy of freedom and opportunity for a new generation of entrepreneurs.
DRK is proof that when local businesses thrive, entire communities benefit. What started as an urgent response to a pandemic-induced crisis has transformed into a vital entrepreneurial hub, one that will continue to create ripple effects throughout Chicago's neighborhoods for years to come.
A vibrant mural celebrating the rich cultural heritage of Chicago's Pilsen neighborhood against the backdrop of the city's skyline. Credit: Jesus J. MonteroChicago's small business owners are shaping their communities with purpose. In this series, we highlight the entrepreneurs behind local gems - each of them building something bigger than just a business. Through Solo, Mozilla's free AI-powered website creator, they're exploring new corners of their community online. Check out DishRoulette Kitchens Solo website here.
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