We’re excited to introduce you to the always interesting and insightful Jackson Flores. We hope you’ll enjoy our conversation with Jackson below.
Jackson, looking forward to hearing all of your stories today. What was it like going from idea to execution? Can you share some of the backstory and some of the major steps or milestones?
I lost my job at the start of the pandemic. My best friend and co-founder of Dish Roulette Kitchen owns and operates an accountancy on the northside of Chicago and he saw first hand how hard the pandemic was hitting small businesses, especially restaurants. That’s when he decided to self fund the first round of microgrants through DRK. At this point we did not have capital beyond the first $1,000, but we had industry knowledge, a network, and the desire to help people navigate what felt like the most difficult time in our history. We created an application with eligibility and requirements and sent the news into the world that we were providing microgrants without any hoops to jump through. At the same time, civil unrest was at an all time high because George Floyd had just happened. In Chicago, small businesses were being vandalized and ransacked so we made a pivot and put a pause on the microgrants and focused on supporting small businesses by cleaning them up so they could reopen. We created a social media post calling on small business owners that needed help cleaning up or boarding up their businesses and put out a call for volunteers. All of a sudden there were 200 volunteers in a tiny church parking lot, each equipped with bags and gloves and brooms to put our communities back in order. When things felt like they were calming down we continued the conversation with business owners and the most natural progression was “what else can we help you with?” The answer was simple- food, healthcare, resources. So we partnered with World Central Kitchen and a local non profit and started a pantry. We distributed hot meals, PPE, covid vaccines, and testing to communities on the south and southwest sides at a frequency of 3 times a week. With that visibility a funder found us and asked us if they were to give us $60,000 would we know what to do with it? The answer was simple– yes. We were in communication with small businesses every day. This money meant that we could fund the grant program and help businesses and the communities they are located in fight to live another day. I never went back to a regular job. Our current initiatives are grant distribution, giving BIPOC their first access to capital, and education so that all businesses can be scalable and sustainable.
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
My name is Jackson Flores and I am the co-founder of DishRoulette Kitchen (DRK) a 501c3 that directly supports women, BIPOC, and undocumented entrepreneurs through funding and education. Before founding DRK, I worked in the service industry as an operations manager creating systems and process for international, multi-concept dining, and quick service operations. I specialize in developing operational foundations and processes for high volume concepts; built to launch, scale, and sustain profitability from concept to completion. Previous experience includes; Starbucks, B&B Hospitality, Michelin-Rated concepts: Quiote and Todos Santos, and the University Club of Chicago.
My parents immigrated to Chicago from Guatemala in 1983. They spent a lifetime navigating the duality of being Guatemalan- American and what it meant to raise children that were not from there and not from here. My earliest memories are of watching tv in only english as my parents struggled to acclimate to their new life. My siblings and I flourished, while my parents kept their wings tucked away. My father grew curious about our neighborhood, the smells, the textures, the people, and he began indulging in the American experience by mouth. Babka, and biryani and tacos de huitlacoche all nestled on the same block. He wanted to learn about America and so we ate. He would make us order and giggled as we struggled to pronounce menu items or interact with the staff. “Now you know how i feel everyday” there was no better way of understanding his perspective than by trying my hardest to order from the halal market with just my hands. It was in a polish restaurant in Jefferson Park where he learned of the trades, and decided to join a union after tittering with the shop owner of how to make “ real money” in this city. We gnashed on pierogi while this man gave my dad a piece of receipt paper with a number to a friend of friend that could help him get the certifications he needed to become a maintenance engineer. That was almost 30 years ago. My father went on to work in Local 399 and is now retiring with a full pension. If it was not for this exchange I have no idea how he would’ve fed and clothed 4 of us. He became a union worker, a homeowner, a proud Navy dad all thanks to a pierogi. It was this moment that I realized that community is everywhere as long as you are willing to learn and break bread from people that are different from you. We looked for that shop owner many years later to thank him, only to find out that he had passed. The restaurant was now a Thai restaurant. And the cycle continued. I didn’t understand why there wasn’t anyone to take up that mantle. He never knew what he did for us. I spent many years lost. Despite my parents’ many sacrifices I was not a good student. I fell through many cracks in a system that was not designed for me. As a child I struggled with conventional things like math and science, but I knew how to make a dollar. More importantly, I knew how to offer goods and services that other people wanted. I was failing geometry, but I knew that if I charged $20 for a forged report card 3 times a reporting period I could in fact cover the cost of printing at Kinkos and would be well on my way to affording my first semester of college. After a failed attempt at college, I joined the workforce. I started working in restaurants and I did everything I failed to do in school. I could make sense of this chaos. I worked my way in corporate restaurant structures, barista to shift supervisor, to AGM and onward. I was a teenager making a full blown salary and I realized– I can teach others to do the same. I bounced around from different corporate restaurant settings but my ethos was the same- teach others how to make money while being part of this system. I see people for what they are, and play to their strengths.
Dish Roulette Kitchen is now a 501c(3) restaurant development center, community cafe and workspace located at 1316 W 18th St in Pilsen. We provide funding and education to women, people of color, and undocumented entrepreneurs. Since 2020, we have distributed over $80,000 in microgrants and over $135,000 in professional services across operations, financial, legal, and marketing. At DRK, I work closely with small businesses to create systems and processes that allow for their businesses to be scalable and sustainable.
Let’s talk about resilience next – do you have a story you can share with us?
In 2018 I was working at a Michelin-rated restaurant as a general manager. We had just secured a second Bib-gourmand and reservations were out the door. Despite my schedule, I managed to start a catering business with my friends. We were cooking for local non profits and businesses, Jordan brand, Vic Mensa, Complexcon. We put something into the universe, and word of mouth started doing the rest. We were in the room. It was surreal. Everything was at my finger tips, but despite every opportunity in front of me, I couldn’t execute. I couldn’t produce. I could barely get out of bed. I did my best, and looking back I really gave that time everything I had. While thoughts of putting a gun to my head became a comfort, I kept saying yes to work. What I didn’t realize is that I was battling depression, and extreme burnout. My mental health deteriorated and I watched everything I had slip through my fingers. I am grateful to that version of me because she got me to where I am now. Had I given into the darkest parts of me, I wouldn’t be here to see the rest of the story through.
Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?
To heal, I needed to admit that I wanted to be here. That I was strong enough to try. When you get so used to carrying your baggage, you forget that you’re the only person that can put the weight down. Asking for help is ok. Asking for help takes courage.
Contact Info:
- Website: www.dishroulettekitchen.com
- Instagram: @jacksonsays @dishroulettekitchen @dishroulette
- Linkedin: https://www.linkedin.com/company/dishroulette-kitchen
- Youtube: https://www.youtube.com/watch?v=9uQ-kHfS-8g
- Other: https://docs.google.com/document/d/1d-c89SDOmJBd6lob2DO5kdHCL0XA-HbaO1W3BM94HXI/edit
Image Credits
Azuree Holloway