Five Questions With Jim Darrow
May 28, 2020

Welcome to “Five Questions,” a new monthly series where Essex Realty Group, Inc. brokers share their observations and experiences gained while working in Chicago’s real estate world. This month we are getting to know Essex Principal Jim Darrow.

Introduction: Jim Darrow is a third-generation investment real estate practitioner with in excess of $1 billion worth of closed transactions. With more than 25 years of investment real estate experience, Jim’s expertise covers the acquisition, disposition, management and development of every type of commercial property. Jim actively owns and manages investment properties throughout the City of Chicago in the neighborhoods of Lincoln Park, Lakeview, Edgewater, Uptown and Pilsen. Jim’s knowledge and proficiency have allowed him to work with many of the most prominent financial institutions, management companies, developers, and Chicago investors. A few of these companies include First Midwest Bank, Lakeside Bank, Kass Management, CA Ventures, Centrum Properties, Marc Realty Residential, and JAB Opportunity Funds.

In addition to his work at Essex, Jim has been recognized, on several occasions, as one of the top Multi-Family/Investment brokers in Chicago. He is the current president of the Lincoln Park Builders of Chicago, serves on the Board of the Real Estate Investment Association, and is an active member of the Edgewater Uptown Builders Association. Moreover, he served as the Chairman of the Chicago Association of Realtors CommercialForum Committee, and as a Director for the Association.

Q: Why were you interested in starting a career in real estate?

Jim: I grew up in the Chicago real estate world. Both of my grandparents were investors here in the Chicagoland area on a small scale; they owned apartment buildings and investment properties. My father and uncle were commercial developers in the Western Suburbs buying vacant property, entitling it and then developing office, retail and recreational properties. Today my family continues to stay involved in the real estate world, so much so that to this day my sister and I always joke that real estate is in our blood! My sister, two cousins and I are all active in real estate in some form or fashion.

It is funny though, because I grew up in the real estate world and was constantly surrounded by it, I took it for granted. After I graduated college I moved back to Chicago and was able to talk someone into hiring me at the Chicago Board of Trade, the job market for recent grads in the 1980’s was much more challenging than what it has been in recent history. That detour did not last long. While at the CBOT I started selling homes, condos and apartment buildings to the people on the floor and in the pits. Once I purchased my first investment property myself and saw I could live rent free, it was game over. I quickly realized real estate was the industry for me and after a few years I left to pursue a full-time career in investment brokerage full time and never looked back.

Q: Why did you choose Chicago as your home base?

Jim: I was born and raised here in Chicago, and like many people who were born and raised here, after you finished college, the natural thing was to head back to Chicago and get a job. We sometimes take it for granted, but Chicago really offers so much – you get to enjoy that big city feel but without fighting for outrageously priced apartments and dealing with the high density and sheer volume of people like in New York City. My wife and I have raised our kids in the city and continue to live in the city, we love the different neighborhoods and all the unique attributes that they all possess. Yes, Chicago is a big city, but it is also a livable city and I cannot imagine living or raising my family anywhere else.

Q: How have you seen the real estate industry grow since your first day as a broker 25 years ago?

Jim: When I started working as a broker approximately 25 years ago, it was very different compared to what it is like for young brokers working at Essex is today. There wasn’t a big push to educate young brokers as a way to invest in that broker to ensure their long-term success. There were no weekly training sessions, no industry leaders invited as guest speakers to educate everyone about tax assessments, building systems, CAP rates and financing deals like we offer today at Essex. Even the three-year analyst training program we offer today is a completely different way for someone to enter brokerage, it simply didn’t exist back then. There wasn’t a sense of camaraderie and collaboration, I remember on my first day it was more like, here is your desk, here is your phone, good luck, get started and let’s see what happens!

Another big change I have noticed is the types of investors who own real estate. When I first started out mid-market multi-family real estate was operated by family-run businesses. There were more mom and pop-style owners. Today you see more owners operating under a more corporate type structure where you are working with investment/opportunity funds, high net worth individuals, family offices and out-of-state institutional groups.

Q: How do you think technology has impacted the industry?

Jim: There have been so many changes that have helped make the real estate market so much more efficient today, compared to when I first started out. There is so much information available at the tip of your fingers! Brokers today can quickly and easily find rental data, ownership information, and who is in the market to buy, or sell. When I first started there weren’t databases, instead we kept rolodexes on our desk with contact information and little notes from our calls. Brokers today have so much more time to create relationships with owners because the research piece of our job can be accomplished much more efficiently. I remember when I would have to set aside an afternoon or a whole day to go to the county building, head to the basement and review microfiche deed records to figure out the property parcel number and ownership information. It took hours upon hours to find even the most basic owner information, then I would take that info back to my office and spend even more time trying to get ownership contact information. Today this is accomplished with a few strokes of a broker’s keyboard and the information is instantly available.

How we marketed property was also completely different. If the owner allowed it, we used to put a sign in front of the building. We also did what was called a 50 up/50 down, which meant when you had a new listing you called the 50 people who owned similar properties in that immediate area to see if they were interested in adding another building to their portfolio. We did not have the robust databases that we have today filled with buyers and sellers for the reasons mentioned previously. You were lucky to show the property to two or three investors in a week, at their convenience. Today we set up specific tour days, multiple times a week, with half hour time slots to tour. 25 years ago, I would have never believed there would be opportunities like there are today to show a building to 50+ investors in the first few weeks of the release of a property and have multiple offers immediately thereafter.

These efficiencies have led to more transactions than ever before. When I first started, I was doing a handful of transactions a year, and now depending on the market conditions, a broker could do 30 to 50 transactions a year. The efficiencies surrounding how we research, communicate and market properties combined with the consolidation of owners has really increased velocity in the market.

Q: Has the global market opened opportunity for investors to invest in Chicago over the last 25 years?

Jim: Yes, and in my opinion, Chicago has always been a great real estate market filled with exceptional real estate entrepreneurs, so we are ready for global attention. Chicago has become an international city, so now not only are we seeing more out-of-state institutional investors, but international investors as well. One reason is that investors have noticed how affordable it is to invest in Chicago, compared to other major metropolitan cities in the US, like New York City or Los Angeles. I think out of state investors see investing in Chicago and the surrounding suburbs as an opportunity to take advantage of better returns without the huge swings in values the cities on the coasts historically experience. Investing in the Chicagoland market is viewed as a safer bet, and a steadier long-term investment strategy.

Q: What is your best deal story?

Jim: How much time do you have, it’s like saying who is your favorite child? All kidding aside, I really don’t have one favorite and can’t narrow it down because every deal is so unique and each one has its own story with its own cast of characters. One of the best and most challenging parts of the business is working closely with people on a daily basis and working with all the different personalities that come with them. But that is what makes the industry so fun and exciting and why I can be going on 25 years in the industry and ready for 25 more!


Since 1990, Essex Realty Group, Inc. has served Chicago's investment real estate market as a top multifamily brokerage firm. Contact us today to learn more about our recent multifamily and mixed-use property sales.

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