Bob Crawford’s Journey from Business Leader to Philanthropic Changemaker

Individual giving remains the driving force behind philanthropy in the United States. Even amid market uncertainty, giving increased by 3.3 percent in 2024 over the previous year after adjusting for inflation, according to the latest Giving USA report.

Bob Crawford understands the difference that one committed person can make. As the founder of Brook Furniture Rental, he spent more than three decades growing a company that would eventually employ nearly 1,000 people nationwide. After selling the company, Bob turned his entrepreneurial spirit towards philanthropy.

In this Q&A, Bob shares the story behind the creation of the Neighborhood Entrepreneurship Lab (NEL), a program he launched in partnership with The Chicago Community Trust. He reflects on the inspiration behind the initiative, the stories behind the lives it has transformed, and the urgent need for philanthropy in today’s uncertain climate.

What inspired you to create NEL?

BC: After selling Brook Furniture Rental in 2014, I found myself at a crossroads. My wife and I took a few well-earned vacations, and then I began to think seriously about what to do next. I had two options: to support private businesses as an advisor or investor, or take a bold step into philanthropy. After decades in business, I felt a deep calling to give back. I had reached out to an old friend, Terry Mazany, the then-CEO of The Chicago Community Trust, and shared an idea that had been weighing on my heart: to help under-resourced individuals build businesses and create generational wealth. Terry was immediately supportive, and we began a months-long journey of community immersion, interviewing leaders, entrepreneurs, and organizations across Chicago’s South and West sides. We discovered a clear need for entrepreneurial training programs.

Eventually, we partnered with the nonprofit Allies for Community Business to launch what has become a highly successful initiative, the Neighborhood Entrepreneurship Lab. Over the past seven to eight years, we have supported over 152 entrepreneurs and helped to create and maintain around 1,000 jobs. This work, raising nearly $1 million annually, has been among the most rewarding of my life. It is a testament to the power of entrepreneurship to transform communities.

Can you share a story about the impact NEL has made on the people it serves?

BC: Two of the most inspiring success stories from NEL are Jimmy Williams and Kia Smith. Jimmy had faced challenges in the past, including being in and out of the justice system. But after turning his life around and getting married, he started a small lawn care business with just a hand mower. He joined our 15-week entrepreneurial training program, which is rigorous and transformative. At the end, he applied for a $20,000 grant to purchase a piece of equipment, a ride-on mower with multiple blades that would allow him to scale his business dramatically. He got the funding, bought the equipment, and today he employs 10 people and has secured major contracts. Kia Smith leads the Chicago Dance Group. She had been performing for years but used the training to expand her vision, creating a teaching studio and mini theater.

We have also seen success with entrepreneurs launching food trucks, cleaning services, and even niche ventures like a plus-size bridal shop, born from one woman’s personal experience, that has now expanded into a second location. One of our earliest participants made bean pies, a staple food in the African American Muslim community. With our support, she moved from her kitchen to a contract packer and into retail stores. These stories reflect the power of targeted support and training.

How and why did you determine the Trust was the right partner for your philanthropy?

BC: My deep involvement in the Chicago community made choosing The Chicago Community Trust as a philanthropic partner an easy and natural decision. I came to know the organization and leadership through many civic initiatives, and I was consistently impressed with the Trust’s work. The Trust shared my vision for being practical and innovative, and that has been the foundation of a strong and impactful partnership.

This is a particularly challenging time for nonprofits, with major shifts in federal funding. Do you have a sense of greater urgency now?

BC: There has never been a more important time for philanthropy than now. Many beneficial programs are being cut or downsized while the needs of our community are only growing. This creates a challenge for philanthropic organizations, but also creates an opportunity to focus on where they can make the greatest impact. For those who can give during this time, now is the time. I am fully engaged in my philanthropy efforts, especially during this increased time of need.

What would be your advice for others who are determining their own approach to giving at this time?

BC: My advice is to start by understanding your strengths and interests. If there is a specific cause or organization that you are passionate about, that is where you should begin. In my case, having spent nearly my whole life as an entrepreneur, I naturally gravitated toward supporting others who are on the same path. If you are unsure where to give, I recommend working with an organization like The Chicago Community Trust, which can help you align your giving with your values and connect you to meaningful opportunities.

“My message to you is simple: get involved. This work has brought incredible happiness and purpose to my life. We have a choice, to serve ourselves or serve others, and I have found the latter far more rewarding.”