Five Questions With Essex Director Dan Shepherd
February 25, 2021

Welcome to “Five Questions,” a 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 Director Dan Shepherd.

Introduction: Dan Shepherd joined Essex Realty Group, Inc. in 2020 as a Director and focuses on business development and the sale of multi-family real estate in the Chicago area. Dan began his career in 2017 as a multi-family acquisitions analyst for a Chicago-area family office, though the role quickly grew to include property sales, property management, asset management, and leasing. He has already represented sellers in numerous transactions across land, multi-family and residential asset types.

Dan graduated from Indiana University's Kelley School of Business in 2017 with a Bachelor of Science degree in Finance and Real Estate.

Outside of work, you can find Dan playing golf or basketball, eating at the best local restaurants, or cheering on the Chicago Bears.

Q: How do you define what you do every day?

Dan: We help the buyers and sellers we work with achieve their goals. Whether that is putting a value on their building, guiding them through a transaction, or simply sharing new information about the market, the goal is to help those who need it.

Q: Why were you interested in starting a career in Real Estate?

Dan: I went to school at Indiana University, and like in many college towns, housing goes fast. I remember I would start school in the fall and immediately start hunting for houses and apartments for the following school year. Oddly enough, I actually enjoyed this arduous process of finding the best possible housing, so I started to wonder if real estate was a field I might be interested in. Eventually, I went to a Real Estate Club meeting on campus to test the waters, as I had absolutely no prior exposure to real estate other than watching HGTV. The first meeting I went to featured a speaker who worked in the commercial brokerage industry in Chicago. I was so intrigued by what I had heard that I wrote a list of about 50 questions and brought them to the head of the real estate program the next morning. We chatted for an hour or so as I soaked it all in, and as soon as we were finished talking I headed straight to my counselor’s office to switch my major to Finance and Real Estate. The rest is history!

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

Dan: I grew up in the Chicago suburbs, so it was a relatively easy choice. But just because it was an easy choice doesn’t mean it was my default choice though. I’ve been to two dozen countries and Chicago is still my favorite place in the world. The food is incredible, the architecture and history are world-class, and it has all the highs and lows you could want from city life. People who complain about the winter have never seen an entire block of neighbors come together to help dig a car out of the snow or been to a dimly-lit neighborhood dive bar after a blizzard. There is something about this city and the experiences that you share with your neighbors that really make you feel connected with the town and it’s inhabitants, regardless of where you are from or where you are headed.

Q: What is your favorite thing to do when you are not doing brokerage?

Dan: Golf! I have been playing golf since I could walk. A few months ago I decided to challenge myself so I started playing golf left-handed. I’ve been playing right-handed for 23 years and am a +2 handicap righty, but I figured it was time to push myself a little further. My next golf goal is to be a single digit handicap both right and left-handed. So, if you see me at the Diversey Driving Range with lefty clubs that clearly don’t fit, shanking ball after ball, just know I’m deep in the process.

Q: Describe one effect on the market you see stem from the reaction to COVID-19?

Dan: The pandemic caused an interesting shift in the real estate market, which we are calling (to borrow from Doug Imber) a “flight to quality”. Transactions of 10+ units in Lincoln Park and Lakeview more than doubled from 2019 to 2020, and cap rates on those transactions dropped almost a full percent, meaning an already desirable market became even more desirable. To contrast that, Uptown and Edgewater transaction velocity decreased by over 70% from 2019 to 2020. When the market is spooked, investors will eschew riskier developments and perceived riskier neighborhoods and return to buying “trophy” properties in areas that they are confident will continue to have low vacancy and with strong tenant bases.


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

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