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Alumni Spotlight: Margaret DeWoskin

Posted By Paige Riemann, Saturday, February 29, 2020




WREAA Social Media Intern, Paige Riemann, interviewed Margaret DeWoskin (BBA 1992) about her career, her time at UW-Madison, and her advice for young women aspiring to be successful in the real estate industry. Margaret is currently the Senior Vice President for JDI Realty, LLC in Chicago. 

Can you tell us about your background and career path before your current role at JDI Realty?


I graduated from UW in 1992 as an undergrad in the real estate program. Following graduation, I went to Chicago to become an analyst at Richard Ellis, which was a predecessor of CBRE. When the two companies merged, a group of us went to Jones Lang Wootton which was a predecessor to JLL. I later received an offer from one of CBRE’s clients, Klaff Realty, which is a boutique real estate investment and development firm. I started in an analytical role and moved into acquisitions and asset management and was exposed to the full life cycle of real estate. We acquired predominantly retail assets and followed numerous corporations, like Montgomery Ward, through bankruptcies. Klaff pioneered the acquisitions through the tenant bankruptcy a path to get to the retailers’ real estate assets that were undervalued and required re-tenanting. That was a great experience. From there I took a turn into banking with a local real estate-oriented bank. I originated real estate bridge and construction loans across the country, many of which were sponsored by the opportunity fund investor that backed Klaff Realty. Following the bank, I joined ORIX Real Estate Capital, Inc. The then recently installed CEO was a former colleague from JLL. He took over in 2004 with the mission to restructure the company and deal with the problem assets. I eventually became the Chief Investment Officer and COO. It was during my time at ORIX, that I was named in the Crain’s Chicago Business 40 under 40 list. When the economy came crashing down in 2009 and ORIX moved their operation to Dallas, I stayed in Chicago. I went back into banking and special assets work for a different local bank, which today is Fifth Third Bank. I later became a partner in an advisory company that specialized in advising distressed banks and dealing with sub and non-performing loans and real estate. The private equity group that recapitalized Byline in 2013 was our largest client. When the acquisition closed, we merged our firm into the bank where I became the head of special assets. I saw that through to the point where the non-performing assets were largely worked through or sold in a bulk sale to a private equity firm. My goal was to move back to the principal side of real estate investing. I returned to Klaff Realty as the director of acquisitions. After spending a year at Klaff, I realized that the broader based real estate investing approach that JDI Realty (a real estate private equity firm) was pursuing was better suited for today’s market. I joined JDI as a senior vice president originating bridge debt and acquiring real estate assets primarily through joint ventures. 

Can you walk us through some of your duties in this position?


Founded 31 years ago, JDI Realty is a boutique real estate private equity firm. We originate structured bridge debt and invest with joint venture partners or directly to acquire value-add properties. We have invested in over $2 billion of real estate and originated over $1 billion in debt. I seek debt and equity opportunities to deploy our capital throughout the county in a wide variety of real estate asset classes.


How has your Wisconsin Network helped you in your career so far? 


In my final semester, before there was an online database, I took WREAA’s paper directory and began contacting alumni in New York and Chicago. Throughout the network, alumni of all levels of the industry open their doors and helped me ascertain numerous job offers. Fast forward 28 years later and I am still constantly connecting with fellow alums. Some of those are Wisconsin relationships that go back to the early 90’s, and others are new alums who have only been out for a few years. The Wisconsin network has been a constant influence throughout my career since the very beginning. The network’s breadth and depth and the participants wiliness to assist one another are endless.


What was your favorite memory from the program or REC?


My favorite memories are of the various intersessions, which were 3-week study abroad courses from the end of spring semester to the beginning of summer school. Professor Rod Matthew was the driving force behind the international trips. In 1992, we went to Tokyo, Seoul, and Hong Kong. It was an amazing experience. We talked to a wide range of real estate developers, investors and bankers. A developer in Hong Kong took us up the construction hoist to the top floor of a high-rise that was under construction. We could see the whole Hong Kong Harbor. That is an experience that I still tell people about 29 years later. 


Who influenced you the most during your time at UW? 


There were many who influenced me at UW. Rod Matthews had one of the most profound effects. He taught the real estate law course, took us around the world, and was a Graaskamp original. He was close with Jim, and he embodied everything that the Graaskamp School of Real Estate was.   


Do you have any pieces of advice for aspiring young women in the Wisconsin Real Estate program? 


My advice is that women shouldn’t see themselves as any different in ability from men. I have never looked at life through the lens of male/female. I have always viewed the world as an open equal playing field. I think that has been very helpful in that I didn’t see anything as a job I couldn’t do, worried that somebody wouldn’t hire me, or felt I was in anyway disadvantaged versus a man. In my opinion, there is nothing that a man can do that a woman can’t. I would never shy away from an opportunity, because I thought I wasn’t qualified. I talk to different owners, developers, and investment advisors every day. It amazes me how few women are in those fields. I encourage women to pursue a career on the transaction side or the investment side of the business. I encourage other women to go out there and not just start as an analyst but continue their careers. Become the person who runs the deals or the group. There is no reason that you can’t run a fund or do whatever you want.


When you aren’t working, how do you like to spend your time? 


I still love traveling the way I did when I was in school, but now I do it with my family. Whether we are showing our kids Paris for the first time or traveling throughout the US and Canada, being with my family and traveling is my favorite combination.



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