It is rare when one can say they have been mentored by a legend. A legend of not just their profession, but also of life in general. Well, I am one of the lucky few, as I had the extreme good fortune of being taken under the wing of the great Howard Weinstein. Howard passed away last week after a brief illness at the age of 77, leaving behind a legacy few in the real estate field can match.
A lifelong Chicagoan who was raised in the Albany Park neighborhood, Howard entered the real estate industry immediately after graduating from his beloved University of Illinois and was hired by the original Chicago real estate icon, Arthur Rubloff. It did not take Howard long to rise up the corporate ranks as he was eventually running the show, opening offices up all across the country. Rubloff & Company was THE place to work in real estate back in the 1970’s and 80’s. So many individuals had the privilege of getting their start at this prestigious firm and Howard played a central role in their development.
In the early 1990’s, Rubloff & Company split into three parts, with the commercial side merging with Koll (and ultimately becoming the modern day CBRE). Howard and his long-time partner Tom Horwich purchased the residential division in 1996 and grew Rubloff Residential Properties into a Chicago powerhouse.
When I entered the commercial real estate business in 1996, my first assignment was to serve as the leasing agent of two Loop office buildings owned by Tom’s family, 100 West Monroe and 30 North Michigan. After 2 fortunate years of experiencing some success, the firm I was working for at that time became mired in some difficulty and I needed to make a change. Tom took pity on me and suggested I come work for Rubloff, as their non-compete clause just expired and they were able to practice commercial real estate again. The catch was that I had to persuade Howard that this was a good idea.
Prior to the meeting, I asked as many people in the industry as I could about Howard Weinstein and the same message kept being conveyed: if you have the chance to work for this guy, do it! The second I walked into his office, it was obvious he had a certain air about him where you could just tell he was someone important. We talked for a few minutes and I somehow convinced him that a 25-year-old schmuck was worthy of using the Rubloff name. He hired me the next day.
Very early on he established two rules that always stuck with me: (1) Don’t embarrass the Rubloff name and (2) Make me a lot of money. I am not sure I was successful with either, but can say without hesitation that working at Rubloff and for Howard was the greatest. He gave me complete autonomy to do my thing and always was there whenever I needed anything. I would’ve stayed there forever if I could have, but that darn recession led to the sale of the firm and yada yada yada, Willard Jones was born.
Early in my Rubloff career, a new owner of a building I had been representing asked me to take over a renewal negotiation that he had been working on with little success. The tenant had a well-deserved reputation for being quite difficult and seemingly had one foot out the door. As a Hail Mary of sorts, I was asked to take a crack at keeping him in the building but warned the odds were slim-to-none. Somehow, I was able to convince the owner of the firm to meet for a few minutes. He basically ignored me and nothing was being accomplished, so I decided to leave. On my way out I handed him my card which he surprisingly glanced at and saw that it said Rubloff. His demeaner abruptly changed and he asked if I knew Howard Weinstein. I told him that he was my boss. Suddenly, he started blurting out all these stories about projects he and Howard once worked on together. Sensing that the tide had turned, I asked if he would like to talk with Howard on the phone. Fortunately, Howard picked up and the two spoke for 20 minutes, laughing hysterically as they recounted old times. As the conversation was ending and the topic of why I was there finally came up, Howard told him to, “stop f-ing around and sign the damn lease.” Sure enough, we completed the renewal, I made a new friend and the owner felt like I pulled off a miracle. That was the power of Weinstein.
Then there were the Rubloff holiday parties. This was Howard’s annual night to shine. He would throw these over-the-top galas at some of the most classic Chicago locations imaginable: the Chicago History Museum, Adler Planetarium, Chicago Cultural Center, Newberry Library, Peggy Notebaert Nature Museum and Chicago Yacht Club to name a few. He always used to tell me that the revenue from the commercial division I ran was used to cover the cost of the party and let me tell you, that was a ton of pressure as I know how important that night was to him. He went out of his way to create a pleasant environment for his agents, which is why so many remained loyal to him and the reason why so many moved on once he sold the business.
No one could command a room like Howard Weinstein. The second he walked in anywhere, he immediately was the center of attention. It was partially because just about everyone in the real estate industry knew who he was, but for those who didn’t, he had a certain approachable swagger about him. However, he never acted like he was better than anyone else. To the contrary, he was always curious to learn about your background and find ways he could relate whether you were the CEO of a Fortune 500 company or the janitor of a building. This is one of so many reasons why people loved him.
Over time, no one had a bigger influence on my career than Howard. I affectionately referred to him as “The Chairman” of Willard Jones Real Estate. We typically got together every other month for lunch and regularly talked about real estate, the Bears and life in general. He talked me off the ledge thousands of times, gave me an immeasurable amount of advice (never expecting anything in return) and taught me Yiddish in the process.
Our cherished phone conversations always started the same way. At Rubloff, it was something like this:
Howard: Jonathan? Weinstein! Did you make me any money today?
Once I started Willard Jones, it changed slightly:
Howard: Jonathan, this is the Chairman calling. Where are my dividends?
Me: As soon as I make my first profit, you are next up on the list
Howard: What am I going to do with you?
The topic would then shift to sports. He was a huge Chicago sports fan, especially the Cubs (one of the few things we disagreed about). I will miss our Monday calls about the Bears (aka “your crap team”) where he would often tell me how he was a better quarterback than Jay Cutler.
Howard also loved his food and regularly consumed the classic Chicago menu: Italian beef, steak (medium rare), deep dish pizza, hot dogs (NEVER with ketchup) and Long Grove Confectionary candy for desert. I always let him select our lunch spots and he usually leaned towards the classics (Manny’s and The Berghoff were two of his favorites). The truth is, I never much cared where we went. I just enjoyed his company and wanted to soak in as much knowledge as I could.
Howard Weinstein was the true definition of a mensch: an honorable, decent stand up person. Not having Howard in my life is going to be tough, as I now have to fall back on 20 years of guidance to solve my problems. While he will be missed so much by so many people, I am enormously grateful for our time together. RIP, Mr. Chairman. Thank you for making me a better person.