Chicago's Men of the Moment

Men's Book
Mar 27, 2017
Tate Gunnerson, Sarah Ryan, Jessie Sardina, Lisa Shames and David Zivan

Photography by Quinn Wharton

From a self-taught artist whose iconic work has been exhibited all over the world to a real estate entrepreneur moonlighting as a TV show co-host, the men of Chicago are having a big moment. Here, five trailblazers sound off—in their own words.


Real estate mogul Sean Conlon lends his expertise—and dollars—to Chicago home renovators whose projects are underwater on CNBC’s new show The Deed: Chicago.

“I’m a real product of the American dream. I truly came here with nothing. In Ireland, we have an excellent appreciation for real estate—that may go back to a hundred years ago when the Irish weren’t allowed to own our homes. So when I grew up and we had nothing else, the house was the most important thing. I still sell real estate first and foremost because it’s home. But I can tell you my philosophy in home flipping—I’ve done an awful lot of it: If it can go wrong, it will. While The Deed: Chicago shows the unblemished side of things, it also shows the real side of it. I lend real money, the emotions the people show are real and the wins are also real. My interactions with the flippers are very no-nonsense because at the end of the day, I’m pulling for them. I love an underdog. What I like about doing the show is that knowing exactly who I am allows me to combine all sorts of skills I have gained. I couldn’t have done this seven or eight years ago, or 15 years ago. I wouldn’t have been equipped to do it. I tend to work very hard for everything I have. I rarely had things aligned perfectly, ever. With this show, it seems, timing is perfect for me.”

Shot on Location at Sean Conlon’s Gold Coast Condo; Styling by Amy Geister