John Whitehead is someone who follows his heart, which in turn led him to NAI Hiffman where he was recently named executive vice president and shareholder. Real estate has always had a presence in his life, his grandfather owned a 4th generation Whitehead Realty in Rockford and it was a source of pride for his family. However, John never worked at the company and he didn’t study finance or business in college–he decided to carve his own path.
On the college experience…
“I only applied to schools in Colorado as I loved to mountain bike, camp, snowboard and ended up having a Vail pass for 5 seasons. It wasn’t until after I got to school that I realized that I had made the perfect choice in going to Regis University in Denver. I made amazing life-long friends, and had some of the most committed teachers who took pride in what they did. A fact that has frankly shocked most of my industry peers is that I majored in Fine Arts with a Photography emphasis. My intention was to use this choice in major to get into the Advertising world.”
On figuring out his career…
“My interest in real estate was something that came about after working in a few other industries. Through my art background, I initially gravitated towards the creative field of advertising. I got a job in Leo Burnett’s in-house production studio called Capps Digital. While I wore many hats for the company, the most interesting role was in the photography studio where I was a production assistant. While it was difficult to quantify, I had a hand in helping to bring in more work for the photography group through the relationships that I was making. It was at this point when I realized that there had to be a better way than working 80 hour work weeks for a salary of about $21,500! I wanted to get into sales. I moved to San Franscisco and did a stint with a dot com then sold copiers and fax machines. I ended up really enjoying the people and company, and stayed four years working my way up to manager.”
On discovering his specialty in real estate…
“My interest in Industrial was essentially through a process of elimination. I did not like the emotions tied up in residential transactions, and I was especially turned off by the sheer number of people trying to make a living in that sector. Office and retail seemed too volatile with what seemed to me much more extreme peaks and valleys. Ultimately it was the geography of my surroundings that helped me to choose my industry. Chicago benefits from its access to so many rail lines as well as an efficient highway network, allowing for companies to get their product to their end users quickly. Being the third largest industrial market in the country and the logical location for companies needing a presence in the middle of America, it made me feel confident that Industrial real estate was the logical choice for me. I ended up getting hired by the late, great Len Caldeira when he was still heading up the Staubach Industrial group. I was there from 2005-late 2008, until I made the move to Hiffman where I have been ever since.”
On what he’s proudest of…
“My family. Colleen and I met on a blind date in 2005. We actually like to call it a double-blind date as the woman that knew me did not know Colleen, just as the person that knew Colleen had never met me. She is beautiful and a driven woman with a passion that I love and find motivating. We ended up getting married on Halloween in 2009 where we had a black-tie masquerade ball. We had my daughter Lauren in June of 2012 while still living in the West Loop. Then like most people in our situation we moved to the suburb of Indian Head Park and my son Brandon ended up joining us in March of 2015. It is amazing how much life changes for the better once you have kids. Colleen, Lauren and Brandon are everything to me.”
On the best advice he’s ever received…
“Your reaction has little to do with what’s in front of you, and everything to do with what is inside of you. In an industry where tempers can escalate, I think that more people could benefit from these words…”
Questions and answers have been edited for clarity.
