April 2020

CRE Future Leaders: Jack Brennan

CRE Future Leaders | Jack Brennan


As the new vice president, industrial services for NAI Hiffman, Jack Brennan assists private and institutional tenants and owners with leasing, sales and development of industrial properties and land in Chicago’s western suburbs. Brennan established himself as a top producer at his prior firm by facilitating $25 million in industrial sale and lease transactions.

Tell us about your background. Where did you grow up, where did you go to school?

I grew up in the Chicago suburb of Oak Park. I’m one of three kids with two sisters, one older and one younger. I went to Fenwick High School in Oak Park and Marquette University in Milwaukee.

When you were young, what did you aspire to be?

In my younger years, I wanted to be a professional basketball player; didn’t take long to realize that was a pipe dream. When I tempered my expectations, I wanted to follow in my dad’s footsteps (as most sons do) and trade commodities. The landscape of that industry changed vastly over the years I was in school, so I was forced to pivot. Real estate wasn’t on my radar until after college. As I learned more, I found it to be an extremely attractive industry, as it aligned well with my skill set and allowed me the opportunity to run my own business in a way. One of the degrees I received was in entrepreneurship, and I always wanted to chart my own course. Brokerage allows me the opportunity to have more control over how I choose to do my work.

How did you get your start in the industry?

Shortly after graduation, I went to work as a headhunter within the manufacturing sector. Looking back, although it wasn’t the long-term career for me, it enhanced my sales skills and prepped me for the future. After about a year, I reached out to people in my network who were generous enough to put me in touch with a few brokerage shops, and I was able to start my real estate career in early 2016.

Did you have a mentor who helped you get on your feet, or is there someone you turn to now for support?

I spent my first four years in the business at Cawley Chicago. All of the senior brokers there were a great support system and allowed me the opportunity to grow. I could always turn to someone with a question, which I’ll forever be grateful for. Additionally, I’ve always been able to lean on friends and family. A lot of my buddies are involved in real estate in some capacity, so I’ve been able to bounce a lot of questions/concerns/thoughts off them, and I still do so regularly. Since joining NAI Hiffman, I’ve found the collaboration and guidance from senior brokers in the office to be nothing short of impressive. I look forward to working with the company’s deep roster of talented individuals and learning from some of the industry’s finest and most respected professionals.

What does a day in the life of Jack Brennan look like?

One of the best parts of our industry is that every day is different. One day I may spend entirely in the office, cranking out calls, conducting research, or compiling proposals or LOI. The next day I could be on a client tour, walking through seven or eight buildings. I’m usually an early riser and like to get into the office early, have my coffee, check world news and industry-related articles, then begin my calls/follow-ups. If I don’t have a lunch, I usually have an open house or building walk-through/showing in the middle of the day. Afternoons are usually in the office, finishing up calls and doing some research for days ahead. If possible, I like to end the day with a workout and home-cooked meal.

What do you like most about your job?

I love the competitive nature of it, coupled with the mutual respect amongst brokers. Oftentimes, we’ll be at a luncheon at the same table as a broker we pitched against a few hours earlier, without even knowing it. We compete against one another all the time but also get to work with each other to get deals done. I love the collaboration within the brokerage group at NAI Hiffman and how clients’ interests are put first at all times.

Looking to the future, what do you hope to achieve/work on that you haven’t already?

Since I got into the business, I’ve always targeted and been interested in full-lifecycle land projects. I’d love to chase an off-market land site, close on it with a developer, see a building(s) go up and be responsible for fully leasing the project.

How do you spend your time away from the office?

When I’m not working, I like to spend time with friends and family, golf, try new restaurants or watch the sunset with a cooler.

What is your favorite place that you have traveled to? Where do you hope to go next?

I’m not the world traveler that some folks are, although I’ve been to Ireland and it was beautiful; I’d love to go back. Hawaii and Italy are also high on the list.


As seen at REJournals.com

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