TOP 100 MAGAZINE

Fred Montgomery: Championing Mentorship with NEL 2.0

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Mentorship has the power to transform lives, businesses, and communities, and few understand this better than Fred Montgomery. With an illustrious career spanning executive leadership in tax, accounting, and legal operations for a major corporation, as well as leadership roles in over a dozen professional, civic, and charitable organizations, Fred has spent decades cultivating expertise and connections that now fuel his greatest passion—empowering entrepreneurs in disadvantaged communities through mentorship.

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For the last two years, Fred has dedicated himself to NEL 2.0, an initiative designed to amplify the impact of its forerunner, the Neighborhood Entrepreneurship Lab. His mission? To inspire businesspeople to become mentors for under-resourced entrepreneurs, to improve access to capital, and to let the expanded reach of mentorship serve as a catalyst for economic growth.

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The Birth of NEL 2.0: A Bold Evolution

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The Neighborhood Entrepreneurship Lab (NEL) was the brainchild of Bob Crawford, a successful entrepreneur and luminary in the Chicago business community. He envisioned a program that brought together entrepreneurs from the South and West Sides of Chicago, private-sector mentors from major financial institutions, and philanthropic backing to foster business success. He partnered with the Chicago Community Trust to support the program financially, and he chose Allies for Community Business in East Garfield Park to manage the program. In just six years, over 120 entrepreneurs participated, with an eye-opening success rate—98% of businesses survived, generating or maintaining 1,000 jobs and creating immediate benefits as well as generational wealth for the owners.

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Recognizing the need to take this initiative to another level, Bob challenged Fred to increase the impact of NEL. He stressed the importance of promoting capitalism with the spiritual element of helping our neighbors. With this in mind, in 2023 Fred began to develop NEL 2.0. After thoroughly exploring government and nonprofit programs and resources in Chicago, he developed a framework based on recruiting a team of volunteers from the private sector, selecting high potential entrepreneurs and forming two novel ways for them to access capital.

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The NEL 2.0 Difference: Beyond Traditional Mentorship

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NEL 2.0 isn't just a rebranded NEL—it’s an enhanced, dynamic approach to mentorship and entrepreneurial acceleration. While NEL focused on 15 member cohorts in structured 10-week programs and is growing this model, Fred saw an opportunity to provide more targeted, timely support, especially for carefully selected small business owners who have great potential.

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Key differentiators of NEL 2.0 include:

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• Smaller, Flexible Guidance – Instead of large groups, the focus of NEL 2.0 is one-on-one mentorship, allowing for deeper, more personalized guidance.
   

• On-Demand Expertise – Entrepreneurs can connect with industry experts when they need them, whether for marketing, finance, HR, or IT guidance, without waiting for a scheduled program.
   

• Diverse, High-Impact Mentors – NEL 2.0 is assembling a powerhouse team of mentors, including a retired president of a $70 million manufacturing corporation, a top advertising agency executive turned entrepreneur, a real estate developer and a software entrepreneur.
   

• Private-Sector Funding Solutions – Two unique funding models—a Bridge Fund and a Catalytic Capital Fund—provide quick access to capital.  One is somewhat similar to a line of credit. The other is pre-seed funding for a business that is too risky for a traditional loan or venture capital.

 

Sunshine Enterprises, a renowned business service organization in Woodlawn, is working with Fred to bring NEL 2.0 to life. Sunshine offers a broad spectrum of training for individuals who want to learn business skills, from side hustles to early stage companies. It wants to extend its reach and can see that offering tailored, industry-specific guidance and easy access to capital can accelerate success in a way that traditional programs cannot.

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A Legacy of Education and Civic Engagement have led to Mentorship and Economic Empowerment

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Fred Montgomery’s journey, from corporate executive to mentor to catalyst for economic growth, is a testament to the power of experience and leadership in fostering community growth. With Swarthmore College, Stanford University, and DePaul Law School among his alma maters, he held leadership positions in the Civic Federation, Taxpayers Federation, Illinois Chamber of Commerce, Tax Executives Institute and First Presbyterian Church of Lake Forest.  And, as co-captain of his college football and wrestling teams, he nurtured the kind of competitive spirit which is at the heart of capitalism.

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NEL 2.0 is more than a mentorship program—it’s proof that with the right coaching, contacts and capital, entrepreneurs from historically disadvantaged communities can build businesses that thrive, create jobs, and revitalize their neighborhoods. As NEL 2.0 expands, Fred’s invitation is clear: if you have the expertise, experience, and willingness to guide an entrepreneur toward success, now is the time to get involved.

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We spoke with Fred to learn more about his mission for NEL 2.0.

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You’ve had an extraordinary career spanning business leadership, community engagement, and education. Instead of retiring, you chose to invest your time mentoring young entrepreneurs in Chicago. What inspired this transition, and how did it lead to your leadership role in NEL 2.0?

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I have deep roots in Chicago—I grew up in Marquette Park and Morgan Park and know how those neighborhoods have changed—so when Bob Crawford asked me to volunteer for NEL, I was immediately drawn to its unique concept. I jumped in as a mentor, and it didn’t take long to see that helping entrepreneurs was a much more positive approach to improving a community than hiring more police or social workers. A year later, Bob Crawford came to me and said, “Fred, we’ve proved this concept works. How can we expand it?” This question set everything in motion.

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My career in the corporate world was professionally challenging and rewarding, but I was basically in the back office, not interacting with and helping customers. The goal was simply to make money for the company. With all of society’s ills and the misfortunes of individuals, I wanted to “give back” in some way. For me, NEL opened the door, and the more I looked inside, the more I could see that individualized training and access to capital were keys to entrepreneurial success and societal change.

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NEL 2.0 takes a unique approach by providing entrepreneurs with full mentoring teams rather than just individual mentors. What inspired this model, and how does it benefit entrepreneurs?

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After mentoring several people, I could see that high performers needed more than a structured program for a limited period of time. Our focus is on acceleration, not incubation. We work with entrepreneurs who have already been in business for a few years, most with revenue, and are ready to scale. Matching them with a team of mentors from educational, civic, and religious organizations across Chicago is becoming a reality. Corporate retirees would also be a good source for a team so I would like to find HR executives to drive this area of recruiting.

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What sets us apart is that our mentors come from the private sector—not government agencies or nonprofits. These are real-world businesspeople and professionals who understand the pace, complexities, and challenges of successful companies . By pairing entrepreneurs from the South and West Sides with a network of subject matter experts—in finance, real estate, advertising, retailing, wholesaling and more—we strive to ensure they receive targeted support tailored to their business needs as they grow and evolve.

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The beauty of this model is its fluidity—as an entrepreneur’s needs change, so does their mentorship team. One mentor might step in to help navigate the bidding process, another might focus on a marketing strategy, and when it’s time to secure a physical storefront, a real estate expert takes the lead. This dynamic approach keeps momentum strong and ensures that entrepreneurs have the right expertise at the right time to keep moving the ball forward.

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Access to capital is a major hurdle for entrepreneurs in under-resourced communities. You’re introducing two innovative solutions—a Bridge Fund and Catalytic Capital Fund—to address this critical need. Can you share how these funds will work and why they’re so important?

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We’re extremely excited about these funds! Both will be privately funded, and philanthropic donors are initially curious,  then enthusiastic with this new approach. The reality is that business moves fast, but too often, entrepreneurs get stuck waiting for capital. Government and nonprofit programs typically have long, tedious processes for approving loans or they require businesses to spend money first and then seek reimbursement. Many small businesses barely have enough cash flow to operate so these delays will limit their growth at critical moments.

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We designed these funds to be responsive and agile, ensuring entrepreneurs can act on opportunities immediately and keep their momentum going.

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The Bridge Fund: If an entrepreneur has applied for a bank loan or a state program but won’t receive the funds for 45-90 days, this fund bridges that gap, allowing them to begin a project right away. Or, if a business has an unexpected expense but steady cash flow from revenue, the fund can bridge the gap. The fund can provide $5,000 to $15,000 (possibly more) quickly based on the recommendation of their mentor, not on a formal application and decision process.

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The Catalytic Capital Fund: This is structured to prepare entrepreneurs for long-term success through either a patient loan or a grant. A patient loan is interest-free for a few years and then paid off at a low  rate over a reasonable period of time. A grant is to provide pre-seed funding for a very promising business. The goal of the funds is to help entrepreneurs develop the financial strength so that they can either secure a bank loan based on their own credit or be attractive to venture capital. We want to bridge the gap between early-stage survival and full-scale financial independence.

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How has the NEL team of mentors helped entrepreneurs overcome challenges and achieve growth? Can you share some success stories and a “lesson learned?”

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A Natural Juice Business: A woman began selling her fresh fruit and vegetable juices at farmers markets, later expanding to online sales and then wholesale distribution to a grocery store chain. Along the way, she faced significant obstacles related to government licenses and funding, but with support from mentors, she secured the food licenses and capital needed to keep going. Her journey has been recognized, including a five-minute interview on ABC TV. Now she wants to buy and renovate a store for retail sales and production, so a real estate mentor joined the team to guide her through architect and contractor proposals, zoning and finance.

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A Childproof Electrical Outlet Protector: A mother invented a unique childproof electrical outlet cover with a hinge. She successfully obtained a patent, found a manufacturer and a packager, and even secured a purchase order from Walmart. However, she lacked the capital to begin production. Through pitch competitions, which I helped her prepare for, she won two competitions that provided the capital she needed. Within five months and the advice of a production expert, her product was on Walmart’s website. Now, we’re bringing in a marketing mentor to help scale her brand.

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A Janitorial and Cleaning Business: A couple in their late 20s started a cleaning business and got a boost by helping store owners clean up after the unrest on Chicago’s West Side following the George Floyd incident. Their reputation grew quickly, leading to commercial contracts. Today, they employ 10 people, including ex-offenders. Despite incurring the increased cost of treating independent contractors as employees, with our guidance they successfully bid on new and larger accounts.

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A Preschool Daycare Center: A woman operated a preschool on the first floor of a two flat in Englewood for 25 years. She’s an exceptional educator. The first time we met, she showed me pictures sent by the parents of former students after they graduated from high school or college. She had strong connections in the public school system and wanted to open an afterschool STEM program for 1st–3rd graders. However, she struggled with accounting and financial management. Over 18 months, we helped her work with an accountant to provide a P&L, balance sheet, budget, and forecast. Despite her dedication, she was unable to learn the skills and this limited her ability to grow. Her story underscores a crucial lesson: financial management is key to scaling a business.

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While not every journey leads to growth, NEL 2.0 wants to provide the resources and mentorship to help entrepreneurs maximize their potential.

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The Call to Mentorship: Why Professionals Should Get Involved

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Once a person sees an aspiring entrepreneur with a dream and the drive to succeed, it is easy to get hooked. They are hard-working, focused, common-sense individuals who just need the right guidance and resources make their business sustainable. It is very rewarding to be a part of the “family and friends” they don’t have and to watch them succeed.

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One of the best ways to get involved, besides contacting me, is to volunteer at a business service organization like Sunshine and coach a pitch competition, attend a workshop, or shadow an experienced mentor. Being a mentor is not about having all the answers—it’s about listening, asking the right questions, sharing experiences, and providing strategic insights. The most rewarding part of mentorship is seeing an entrepreneur take a dream and turn it into a successful business.

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Fred Montgomery
Mentor, Advisor
NEL 2.0
LinkedIn: https://www.linkedin.com/in/fred-montgomery-b279a422/