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John May

36, River North

Real-life roles: Roving CEO, nonprofit guru 
Starring in: Breakfast at Tiffany’s

What, exactly, is a roving CEO? In his professional life, May joins troubled companies and shapes them up before moving on. It means one short-term gig after another, but don’t call the East Carolina University grad a commitment-phobe; May dedicates nearly all of his nonwork waking hours to two local nonprofits. In addition to serving as president of the cancer support group Imerman Angels, May is launching Next Step to a Career, which will match young professionals with mentors. In the meantime, May dispenses wisdom to his kid brother, a college freshman: “He needs advice on everything from class to girls, and he needs it frequently, so he gets it daily.”

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Childhood nickname? GQ. I always dressed nice.

Have you ever collected anything? Wine corks. They bring back memories, usually of an experience with somebody.

Who are you a secret groupie for? I hate to admit this, but Catherine Zeta-Jones. She’s exactly my type.

Do you have any tattoos? No, but I’d make sure the girl I was dating did—anything sexy on her lower back.

What’s in your pockets right now? Nothing. But I do have pants on.

In a dream world, who would you look like? Brad Pitt. Write like? It was my job. Dance like? Anybody worthy enough to be in an MTV video. Cook like? Chef Nobu Matsuhisa, the founder of Nobu. And sing like? Frank Sinatra.

What do you do every day? Take a shower, brush my teeth, watch MSNBC and ESPN, work out, eat, take a vitamin, and check my e-mail.

Most recommended book? Leading with the Heart, by Coach K.

Name one thing that’s overrated: Sleep.

Who are you a secret groupie for? I hate to admit this, but Catherine Zeta-Jones. She’s exactly my type.

When you’re alone, who do you play air guitar to? Coldplay or Rush.

What song will be played at your wedding? I’ll leave that up to the girl.

What’s your go-to homemade meal? D’Agostino’s pizza.

Fill in the blanks: Vacations are for relaxing with friends, not having anything stressful to worry about.

You pull a Ferris Bueller and call in sick on a beautiful July day. What do you do? Work out, call my friends, go to the beach or the pool, and hang out all day. Or, catch a flight and go down to Mexico.

What Chicago neighborhoods have you lived in? Just River North.

How long is too long to spend looking for a parking spot? Two minutes, and then I’m bolting.

Teacher’s pet or class clown? Clown. I was always mischievous.

What did you think you’d be when you grew up? Honestly, a successful businessperson. When I was six years old, I was going door-to-door selling rocks.

Name one thing you have in your house from your childhood: My old basketball shoes, Air Jordans.

And one embarrassing thing you hide when guests are coming over: All of my mail, because I only check it once or twice a month, so there’s stacks upon stacks. I stick it in one of my closets.

Describe the state of your closet: Somewhere between packed and a disaster.

What’s your power outfit? Jeans and a T-shirt.

What’s too much to pay for jeans? I’d say $250. Jeans are pretty expensive these days.

Last time you jumped up and cheered? When Duke beat Carolina.

Last time you told a lie? A really long time.

Last time you Googled yourself? About a year. I couldn’t find anything, other than business stuff. I’m all clean.

Worst advice you’ve been given? To look out for yourself, rather than others. In the business world, you’re ingrained to look out for yourself, but I disagree.

What do you do when a server at a restaurant brings you a horrible dish? Usually just shove it to the side and order something else.

Gutsiest thing you’ve ever done? I left a fairly comfortable position to go turn around a troubled company with a lot of risk involved. But it turned out to be a success story.

What time is your alarm clock set for? Six-thirty a.m.

And how many times do you hit the snooze button? Four.

Dive bar or nightclub? Both, depending on the night.

Drinks before 5 p.m.: always, sometimes, never? Never.

What’s your remedy for a tough day? Going to the gym and hanging out with my friends.

Fill in the blanks: I’d rather have a significant other who is sexy and fun than gorgeous and boring.

How do you show someone you’re not interested? Put space between us. I wouldn’t be quite as attentive as I was prior to, and not quite as responsive.

What did you do on your best date? Cozied up to a wine bar, talked for hours, and took a stroll under the moonlight on a beautiful summer night.

Where would you like to get engaged? Either where we went on our first date, if it was memorable, or on a beach somewhere exotic and far away: Greece or Barbados or St. Tropez.

What makes someone a Chicagoan? A passion for the city. It’s an insular culture in that, once you’re here, it’s almost impossible to leave. People are real and down-to-earth.

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