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Bisnow One-On-One: 16 Questions With Fifield Realty Corp. Chairwoman Randy Fifield

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This series profiles men and women in commercial real estate who have profoundly transformed our neighborhoods and reshaped our cities, businesses and lifestyles.

If Chicago real estate has a royal couple, it would have to be Steve and Randy Fifield. Steve has been a fixture in Chicago real estate since the mid-1970s as chairman of Fifield Cos. He was primarily an office developer with a heavily overleveraged portfolio when Randy approached him in 1992 for advice about a residential development she was pursuing. In Randy Fifield, Steve found an equal who encouraged him to diversify his assets into multifamily, and later a business partner.

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Fifield Realty Corp. Chairwoman Randy Fifield with former President Barack Obama.

The Fifields, who married in 1995, have developed more than 4,600 new apartments in Chicago since 2010, and own multifamily projects in Los Angeles, San Francisco, Florida, Las Vegas and Hawaii. Today, Randy is chairwoman of Fifield Cos.' development arm, Fifield Realty Corp., and oversees the design, marketing and execution of Fifield developments.

Bisnow: How do you describe your job to people who are not in the industry?

Fifield: I describe my job as being a maestro — we bring everyone together and make our projects sing!

Bisnow: If you weren’t in commercial real estate, what would you do?

Fifield: If I [were] not in real estate, I would be a preschool teacher.

Bisnow: What is the worst job you ever had?

Fifield: I have never had a job I did not like.

Bisnow: What was your first big deal?

Fifield: Buying the high-rise portion of the Civic Opera House for $19.2M in 1994, at 28 years old.

Bisnow: What deal do you consider to be your biggest failure?

Fifield: Not being able to stop Steve Fifield from wanting to build condos between 2004 and 2008.

Bisnow: How do you define “making it”?

Fifield: Making it is having love, laughter, good health, curiosity and a job that you do because you love it like a hobby.

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Century West Partners Managing Director Alla Sorochinsky, Fifield Cos. Chairman Steve Fifield, Fifield Realty Corp. Chairwoman Randy Fifield, Century West Partners' Michael Sorochinsky.

Bisnow: What is your biggest pet peeve?

Fifield: People that say “I can’t.”

Bisnow: Who is your greatest mentor?

Fifield: My husband — Steve Fifield.

Bisnow: What is the best and worst professional advice you've ever gotten?

Fifield: Best advice — life will pay whatever price you ask of it, and you can never fire a bad employee too soon. Worst advice — you do not need to do a peer review on construction projects if you have a good architect.

Bisnow: What is your greatest extravagance?

Fifield: Buying and renovating apartment buildings and homes.

Bisnow: What is your favorite restaurant in the world?

Fifield: My favorite restaurant in the world is Jean Georges in NYC ... eat the tuna ribbons with avocado and ginger sauce.

Bisnow: If you could sit down with President Donald Trump, what would you say?

Fifield: My advice — give Twitter a rest; count to 10 before speaking and please listen to your advisers. In addition, thank you for not taking away the 1031 and leaving carried interest alone.

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F&F Realty President/CEO David Friedman, F&F Realty designer Ronna Friedman, Alderman Walter Burnett, Fifield Realty Corp. Chairwoman Randy Fifield and Fifield Cos. Chairman Steve Fifield celebrate breaking ground at the 727 West Madison construction site.

Bisnow: What's the biggest risk you have ever taken?

Fifield: Having five children, marriage and signing personal guarantees on millions of dollars. I have been very lucky across the board!

Bisnow: Whose work do you most admire?

Fifield: The work I admire most — anyone with passion for what they do.

Bisnow: What keeps you up at night?

Fifield: My husband.

Bisnow: Outside of your work, what are you most passionate about?

Fifield: Outside of work, I love my husband, kids, my dogs, walking anywhere, mystical or serendipitous moments, reading, art, fashion and travel. (And ... looking for real estate deals.)