Business Spotlight: Black Entrepreneurs Leading By Example in Chicago

February 17, 2021 |  Business Spotlight: Black Entrepreneurs Leading By Example in Chicago | By Gustavo Ustariz, NMSC

Left and right: Iesha Malone of Rose Cafe interacts with customers. Center: The Ware Ranch Restaurant.

Opening and running a small business is no small business. When you add a worldwide pandemic, lockdowns to reduce the spread of COVID-19, and an ensuing economic downturn, it becomes a battle for business survival. The health and economic challenges of the past 12 months have affected everyone, but for Black people in the United States these challenges have been exacerbated by tragic events that highlighted systemic racism and inequality. And yet, every day across the country Black entrepreneurs are working hard, starting and running businesses, strengthening the social fabric of their communities, and serving as an example to future generations.

For Black History Month, we want to recognize and celebrate the Black business owners and entrepreneurs who have overcome challenges and obstacles in launching and running their own businesses, thanks to resilience, creativity, and hard work. We reached out to Andrea D. Reed from the Greater Roseland Chamber of Commerce, one of the Chicago organizations serving as corridor managers for Chicago’s INVEST South/West initiative and an UrbanMain partner. Andrea enthusiastically put us in contact with Judy Ware and Iesha Malone. Judy is the owner of the Ware Ranch Restaurant, a steakhouse in the Roseland neighborhood in Chicago. Iesha is the owner of Rose Café, a bookstore and coffee shop also located in the Roseland community. This Q&A is a peek into their entrepreneurial story:

Why did you become a small business owner?

Judy Ware: “I became a small business owner in 2007. I had just left corporate America and at my age I figured my prospects for gaining employment would have been slim to none, so I made the decision to start my own business...a transportation company.”

Iesha Malone: “Honestly, I became a business owner to be living proof of what you can do if you really wanted something. I live in a neighborhood where there isn't a high expectation and therefore people do not strive.” 

The takeaway: Since starting her transportation company in 2007, Judy has also owned a daycare and is now the owner of a restaurant. Iesha is using her love for books and business skills to serve as a positive example to people in her community. 

Tell us about your commercial district. Why did you choose to locate your business where you did?

Judy Ware: “The South Michigan Avenue Commercial Corridor, it’s a commercial district that has seen better days. There are organizations such as the Roseland Chamber of Commerce, and many more that are working with the City of Chicago to bring South Michigan Avenue back to its rightful place in history. My husband, Victor L. Ware, Sr. heard that the Ranch Restaurant was up for sale. We decided to explore the idea of owning a restaurant. We used our savings to purchase the restaurant, in the neighborhood where we had purchased our home. We were fully invested in the revitalization of this community.”

Iesha Malone: “I was born and raised on the South side of Chicago but now I work in Evergreen as an educator. There is a big difference in resources that are available. Roseland has nothing… I don’t want to go all the way to Hyde Park for a good book and cup of coffee; that's insane!”

The takeaway: The pride of home and place is key to these entrepreneurs. Local residents starting businesses in their own neighborhoods help strengthen the social fabric of their communities. This sentiment aligns with UrbanMain’s work with Chicago’s INVEST South/West initiative which seeks to build community wealth through developing strategies for area residents to own commercial property and start businesses in their neighborhood.  

What would you encourage other commercial district programs to do to support their small business community?

Judy Ware: “Take a real good look at what's missing and speak with the stakeholders and residents to see what they would like to see in their community. Make sure the businesses that want to set up shop will enhance the beauty of the community and bring something the community needs and wants.”

Iesha Malone: “I would encourage people to use social media platforms to connect. Your business is only as big as your connections.”

The takeaway: Know the market, look for opportunities, find an unmet need or demand, and get the community on board. Make good use of the power of digital channels and social media to amplify your message and expand your reach. Network, network, network.

What advice would you give others who are looking to start a business?

Judy Ware: “My advice to anyone who wants to start a business is to do your homework. There are many challenges operating your own business. Make sure you have money in reserve should you fall on hard times. Don't think you are going to get rich overnight, have a passion for what you do and most of all make a positive contribution to the community you have chosen to start your business.”

Iesha Malone: “I would say have some money saved up and have a job to help fund your business… Be patient, it's coming.”

The takeaway: Like many entrepreneurs and small business owners Judy recommends taking the time to plan your business and to know the market. Ask yourself, what need can your product or service supply? Both agree that patience is key and that a rainy-day fund is very important, especially during the start-up period. Establishing connections to local business-serving entities, such as Greater Roseland Chamber of Commerce and regional Small Business Development Centers, can be a saving grace to new and existing businesses as they seek out resources. 
A big thank you to Judy and Iesha for sharing their stories with us! Join us this month (and all year long!) in highlighting Black businesses in your Main Street district and telling us how you support them.