Standing Alongside Women in Business

DRK participated in the Chicago Sky Foundation's 2026 Women's Small Business Cohort, presented by Lendistry, joining a community that connects the visibility of women in sports with opportunity for women in business. That connection matters: when women have a platform, they can use it to open doors for others. For us, the cohort was an opportunity to learn, contribute, and help make room for more women to be seen, supported, and included in the relationships that shape business growth.

The program brought us together with women building businesses across health and wellness, beauty, food, retail, pet care, and children's literature, alongside our work supporting small businesses.

Fellow participants include Vinyasa Vibes Yoga Studio, Casa Soluna, All Jazzed Up, Candyality, Chicago Flower Market, Thrive Wellness + Aesthetics, Division Chiropractic, Erin's Cup, Pooch Town, ¡Viva! Los Libros, and La Juicy Jars.

The cohort gave us space to learn alongside women navigating different industries and many of the same decisions: how to reach customers, build a team, finance growth, and expand without losing what makes their work meaningful. It also brought greater visibility to the businesses and organizations these women are building across Chicago.

For DRK, that connection matters. We support entrepreneurs every day, and we also benefit from being in a room where we can ask questions, exchange experience, and build relationships as peers. The program culminated in a live pitch competition, but the relationships continue through the alumni network.

Our commitment to women in business extends beyond participation in a program. It means sharing opportunities, making introductions, referring customers, and recognizing the expertise women bring to one another's work. We want our visibility to help more people discover the businesses beside us.

Connecting Youth Talent with Small Business Needs

In summer 2026, DRK piloted the Career Lab with a small group of high school seniors and incoming college freshmen. The pilot helped us explore how workforce development and small business support can strengthen one another when young people contribute to real projects and learn directly from the people running a business.

Small business owners wear many hats. Serving customers, managing finances, and keeping daily operations moving can leave little time for marketing or making a business easier to find online. Participants helped develop practical tools, systems, and processes using technology and AI, connecting their learning to work that business owners needed help moving forward.

Their contribution went beyond knowing how to use digital tools. Young people see how their peers discover a new place, decide what is worth their attention, and choose where to spend. As they enter the workforce and gain purchasing power, their perspectives can help businesses understand the next generation of customers. We want those voices represented in the tools we build.

The learning moved in both directions. Students brought ideas, curiosity, and an understanding of digital culture. Business owners brought experience with customers, budgets, and the daily tradeoffs of entrepreneurship. Financial literacy and technical assistance became part of that exchange, giving students context for how their work could support a business.

The pilot is shaping our approach to expanded workforce programming in 2027. We are interested in what young people and small businesses can build together: affordable tools, clearer processes, stronger online visibility, and professional relationships that continue beyond a single project. The goal is practical experience for students and useful support that businesses can sustain.

Supporting Pilsen's Businesses and Future

Pilsen's small businesses help carry the neighborhood's culture forward. They are places where people work, gather, share traditions, and build a livelihood. Improving a commercial corridor means investing in those connections as well as the buildings that house them.

As Pilsen Corridor Lead for Chicago's Commercial Corridor Storefront Activation program, DRK supports efforts to bring vacant storefronts back into use along 18th Street between Morgan and Ashland. This work connects business owners with opportunities to rehabilitate spaces, improve the block, and contribute to a local economy where more dollars circulate among neighborhood businesses, workers, and families.

Our support continues beyond grant selection. Applicants who are not selected will receive continued education and guidance to explore other City funding opportunities, understand requirements, and prepare their next steps. The work of developing a project, gathering information, and planning an investment should remain useful even when one funding opportunity does not move forward.

Bringing Small Business Voices into Neighborhood Planning

DRK joined the Pilsen Industrial Corridor Study process to help ensure small business needs are part of the conversation about the corridor's future. Alongside residents, community leaders, and neighborhood organizations, we bring the perspective of entrepreneurs whose livelihoods depend on the decisions being made around them.

Our storefront work gives us a practical understanding of what those decisions mean: whether a business can find a suitable space, afford improvements, hire locally, and remain in the neighborhood as it grows. The study offers another opportunity to bring those needs into planning and connect investment with the businesses, workers, and cultural life that make Pilsen what it is.

We contribute as neighbors and collaborators, learning from the people and organizations that have long cared for this community. We also see an opportunity to share what we learn with delegated agencies and partners across Chicago, helping connect small business support, workforce development, and neighborhood planning in ways that reflect each community's priorities.

Learn about the Pilsen Industrial Corridor Study.

Supporting the People and Stories Behind Our Communities

In 2026, DRK became the fiscal sponsor for Échale Ganas and Equity in Care. Fiscal sponsorship gives these initiatives an organizational home as they develop their work. It also allows DRK to support community needs that are closely connected to entrepreneurship: whose stories are heard, how people access information, and how the people building businesses care for themselves.

Échale Ganas | Community Journalism

Founded by Jesús Montero, Échale Ganas is a Chicago newsroom bringing journalists, reporters, editors, and community storytellers together to report and tell stories collaboratively. His vision makes room for different experiences and forms of storytelling within independent community journalism.

We see a meaningful connection between this work and the communities DRK serves. Stories help people discover a neighborhood business, understand someone else's experience, and participate in conversations that affect their lives. Supporting a community newsroom is one way to support the people who document, explain, and give visibility to that everyday life.

Through fiscal sponsorship, DRK is helping give Échale Ganas room to develop its work and build those connections.

Explore Échale Ganas.

Equity in Care | Mental Health and Entrepreneurship

Equity in Care is a mental health initiative for Chicago small business owners. Building a business can bring independence and purpose alongside uncertainty, financial pressure, and the responsibility of keeping others employed. Entrepreneurs and creators from communities with fewer resources may face additional barriers just to access the support others can more readily reach.

The well-being of business owners matters to their families, teams, and communities. Through fiscal sponsorship of Equity in Care, DRK supports the recognition that mental health is part of what people need to build and sustain a business.