Jeff Weinberg on Building a Real Estate Empire with Chicago Roots

Real Estate Moguls

Jeff Weinberg, President of Drexel Properties, has a fascinating story that intertwines the worlds of hospitality and real estate. Born and raised in Chicago, Jeff’s roots are deeply embedded in the city’s rich restaurant culture. His family owned several well-known establishments, including the iconic Diner Grill on Irving Park in Lakeview, which has been serving the community since 1934. Jeff fondly recalls the vibrant energy of the diner, a place where late-night revelers would go to sober up or enjoy a post-game meal after a Cubs game.

Despite the allure of the family business, Jeff felt a different calling in his mid-twenties. As his friends started buying condos, Jeff realized he didn’t just want a space in the sky—he wanted to own the ground beneath it. At 26, he purchased his first property, a two-flat in West Lakeview, marking the beginning of his real estate journey. A decade later, he founded Drexel Properties, starting with a 20-unit building in Hyde Park. This transition from hospitality to real estate wasn’t just about financial growth for Jeff; it was about creating lasting value.

Jeff's success in real estate is rooted in his ability to see properties not just as investments, but as communities that need nurturing. His background in the restaurant industry instilled in him a strong service mindset, which he applies to his property management business. Jeff says, “I run my property management company like a restaurant. I want my tenants to love where they live and feel great every day when they come home.” This philosophy has been central to his success, as he believes every business is ultimately a service business.

In the early 2000s, Jeff’s ventures expanded beyond buying properties. He took on challenging projects like converting apartment buildings into condominiums and even building a single-family home from the ground up. He enjoyed the tangible progress of construction, likening it to the satisfaction of seeing wood being cut and buildings rising. Yet, his heart remained in managing multifamily apartments, where he could directly impact people’s lives.

Jeff’s approach to real estate is deeply personal. He values relationships and believes in taking care of people, whether they are tenants, investors, or partners. He recounts a story of a building with numerous code violations that others wouldn’t touch. Jeff saw an opportunity and worked closely with city officials to resolve the issues, demonstrating his problem-solving skills and dedication to improving communities.

His service mindset extends beyond his professional life. Jeff is actively involved in mentoring programs like Chicago Scholars, which supports first-generation college students from inner-city high schools. He also participates in Students Run Chicago, a program that trains high school students for marathons. Jeff’s commitment to giving back is rooted in his own experiences of humble beginnings and the desire to create opportunities for others.

Jeff’s dedication to service and community is evident in every aspect of his work. He advises businesses to adopt a service mindset, focusing on solving problems immediately rather than making excuses. He believes that taking care of people leads to better business outcomes and a more fulfilling life. “If you solve the problem first, people will help you solve the problem,” he says, highlighting the importance of empathy and proactive problem-solving.

As Jeff looks to the future, his goals include pulling back from the day-to-day demands of his business to focus more on mentoring and giving back. He wants to help young people find paths to success, just as he did, and create generational wealth and independence. His story is a testament to the power of showing up, taking care of people, and staying true to one’s values.