Jacob Goldstein joined Chicago’s Greenstone Partners in September as a director. It’s the latest stop in what has already been a successful commercial real estate career for 30-year-old Goldstein. Since becoming a licensed broker in 2016, Goldstein has been involved with more than $100 million of multifamily and mixed-use transactions in the Chicago area.
We recently asked Goldstein about his career, the secrets to his early success and his goals. Here is what he had to say:
Tell us about your background. Where did you grow up, where did you go to school?
Jacob Goldstein: I grew up locally in the North Shore Chicago suburb of Highland Park and graduated from the University of Illinois Urbana-Champaign.
How did you get your start in the industry?
Goldstein: I learned a lot about the industry from a pretty young age, thanks to my dad, who has extensive experience as a commercial broker and owner/operator of a variety of commercial assets. His guidance and insights helped shape my path in commercial real estate. I enjoy the entrepreneurial aspect of the profession, where I have the freedom to build my own business, set my goals and directly see the impact of my efforts. I also find it rewarding to build meaningful relationships with clients, helping them navigate important decisions and achieve their aspirations.
I started at Essex Realty Group, where I began my career as an analyst for a team that focuses on North Side Chicago multifamily and mixed-use transactions and gained extensive experience in this role. Over the years, I worked my way up to becoming a director, building a strong network of clients and deepening my expertise. This foundation paved the way for my current role as a Director at Greenstone Partners.
Did you have a mentor who helped you get on your feet, or is there someone you turn to now for support?
Goldstein: I’ve been fortunate to have several mentors throughout my career. My Dad and Grandpa were instrumental in guiding me from the start. Their guidance, through participating in real estate-related discussions and addressing challenges early on, was extremely helpful to navigate obstacles as a broker just getting on my feet.
During my eight years at Essex Realty Group, I worked closely with a handful of mentors who played a pivotal role in my development. Their guidance was crucial in shaping my professional skill set, and I continue to seek advice from colleagues and industry leaders to stay informed and grow in my role. I firmly believe that being paired up with a solid mentor early in your career is essential for navigating the commercial real estate brokerage landscape.
What does an average day at work look like?
Goldstein: Most days at work have a good rhythm, though I keep things flexible. I usually start by checking out new listings, recent sales, and any industry news that could affect my clients. From there, I focus on what needs to get done—whether it’s catching up with clients, showing properties, or diving into market analysis. I most enjoy meeting with owners at their buildings, as I gain valuable insights and learn a lot from these firsthand interactions.
There’s always something unexpected that pops up, so I’m often jumping in to solve problems or handle negotiations. I tend to spend a lot of time in my car, so I’m always listening to podcasts that relate to commercial real estate, sales or investing in multifamily assets.
I also make a point of planning my week on Sundays since no two weeks are alike. Staying organized and adaptable is key in this job, and I try to bring that energy to everything I do.
What do you like most about your job?
Goldstein: What I like most about my job is the ability to add value to my clients and the flexibility of controlling my own schedule. This is a people business, and I enjoy making connections, learning from others, and being a valuable resource. It’s rewarding to work with such great people on a day-to-day basis and to contribute to their success.
Looking to the future, what do you hope to achieve/work on that you have not already?
Goldstein: Looking to the future, I hope to work on larger opportunities across core North Side Chicago markets. I’m excited about growing my role and tackling new challenges in these key areas. Additionally, I aspire to become an owner/operator of multifamily properties, as I believe firsthand experience in ownership will further strengthen my ability to advise clients with greater insight.
How do you spend your time away from the office?
Goldstein: Outside of work, I stay active with activities like pickleball, boxing, basketball, and working out, enjoying the mix of social and competitive elements, especially meeting new people through pickup sports. I also love playing guitar, going to live shows and spending time outdoors. A show I really enjoyed this year was the Marcus King Band at Salt Shed, a new riverfront venue that’s quickly become one of my favorites.
