Jay Michael


Born In
Skokie, IL

Chicago, IL

Job Description
Lifestyle Architect. In search of
the world’s best way to live.

Favorite Cities
Tel Aviv, Brussels, Hanoi,
Hong Kong, London & Memphis



Jay Michael is…

A lifestyle architect and real estate developer with a keen eye for form, function, and just the right touch of unique personality. I love to connect with the world around me in the broadest sense, be it with friends, families, or even strangers in the places I visit.


You are the COO and Co-Founder of FLATS Chicago. How did you get started there and how do you keep it thriving?

I started FLATS with my business partner and childhood best-friend, Alex. We saw a need for improved living in the mid-level housing market and approached the need with a plan unlike anything the Chicago real estate market has seen. Alex and I have two entirely different skill sets that complement each other like a marriage! He always tells me that he has 3 women in his life: His wife, his mother, and me.


What would you say is the luckiest break you’ve gotten in business?

I found my lucky break in a rather unfortunate situation. I was at my dad’s funeral about 10 years ago and coincidentally ran into Alex after years of lost contact. We were both interested real estate and decided to partner up. It’s not often that a run-in at a funeral changes your life forever.


What is the worst job you’ve ever had?

My high school job working at Outback Steakhouse. Hands down. Slingin’ Blooming Onions around all day didn’t exactly satiate my teenage angst or my then-acne.


How do you successfully remain an active member of Chicago’s LGBT community?

I’m involved with a few different LGBT organizations around the city, but most importantly, I think a valuable part of being a member of the LGBT community in Chicago is the way you live your life. I always assume I can live with the same rights as anyone else, be it gay, straight, married, single, etc. If straight people can hold hands walking down the street, then so can I.


You have a definite case of wanderlust. Where is the most interesting place you’ve been?

A few years back, I biked the valleys on the China / Vietnam border with my business partner for his 30th birthday. We fell in love with the people in one of the small villages along the ride. For two groups of people that were comprehensibly different from one another, there was an undeniable connection we felt to them in our conversations. We even cancelled the plans on our last day of the trip to spend the day hanging out with them.


How do you manage to balance work and an incredibly active social life?

Eat healthy. Rest well. Stay in good company. Rinse and repeat.


How do you stay healthy and what keeps you feeling good?

I am adamant about staying active every day. If I don’t think I’ll have time to work out, then you can be sure I’ll be biking to work. There’s always time to incorporate some form of physical activity into your day. I’m also big on eating raw fruits and vegetables from local sources. Throw in a trip to Chick-Fil-A once a month and I’m all set!


What level of importance does your family plays in your life?

Family is and always has been a top priority for me. I have a great deal of respect for people who prioritize family as well. Family is an open-ended word for me though and means more to me than solely blood relatives. Friends can just as easily become family. Life feels lonely if you don’t have people you can call at whatever time for whatever reason. I’m fortunate enough to have people I can always count on.


What can’t you turn down?

(Ever)– I can almost never turn down a good challenge! And a Chick-Fil-A sandwich on a Sunday… thankfully they are closed that day.

What would you say is the key to living an enjoyable life?

Live life as a journey without a specific end-game. Find value in all of the experiences you have along the way. I have found that some of the most challenging moments in my life have transformed me just as much as the joyous ones have. The sweet isn’t as sweet without the bitter.


The options are endless. Who is your dream date? Where would you go and what would you do?

A “bring him home to mom” dream date? Hugh Grant. A “bring him home from the bar” dream date? Channing Tatum. Hell, I could probably bring either one home to mom, but I think she might have a little more of a soft spot for the smooth-talking accent of a Brit.


What is the worst date you’ve been on (names not included, of course)?!

I went on a date with a (supposed) high-end stylist not too long ago. He said he loved my shirt and asked me where I got it from. I told him it was from LL Bean and his face went completely blank. The “stylist” then proceeded to ask me what LL Bean was. NEXT!


Give us the lowdown on your adorable French Bulldog, Louise.

She’s basically the cutest bunny-pig alive. Her mom is a bunny and her dad is a pig. At least that’s what I tell the kids who live on my street. And no, they didn’t question it for a second. Her personality is out of this world hilarious and she has formed quite a successful modeling career posing for all of our FLATS ads. Someone call Tyra and get this dog on ANTM.


What would you say is your biggest pet peeve?

People with long lists of pet peeves…You are entitled to a few, but let’s not get carried away.


What lies ahead for you?

A couple of babies and a LOT more wanderlust.