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Toni Pelaez

32, West Loop

Real-life role: Vice president of a private equity firm 
Starring in: Valley of the Dolls

How would you describe your job to someone who failed Econ 101? “I make investments in private companies,” says Pelaez. “The checks we like to write are anywhere from $10 [million] to $50 million.” A Lane Tech grad, Pelaez grew up in West Rogers Park, the neighborhood in which her parents settled after emigrating from Cuba. Their example inspired their daughter’s ambition; after college, Pelaez, a University of Illinois finance major, went on to attend Harvard Business School before landing her current post. “When they came to the States, they started from scratch,” she says of her parents’ drive. “Their work ethic was instilled in my sisters and me.”

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What do you do every day? In the morning, I always make a raw shake. I’m a health nut.

What’s your remedy for a tough day? A foot massage.

Drinks before 5 p.m.: always, sometimes, never? As often as possible.

What makes someone a Chicagoan? Describing distance in terms of time, instead of by miles. I travel all over and everywhere else, people say something is “a half mile away, a quarter mile away,” but in Chicago, people say, “It’s 15 minutes down Clark and ten minutes to the expressway.”

Where would you like to get engaged? Anywhere would be just fine.           

In a dream world, who would you look like? Me, when I was 22. Write like? Jeffrey Steingarten. Dance like? Justin Timberlake. Cook like? My mom. And sing like? Norah Jones.

Favorite movie hero? Dr. Richard Kimble, The Fugitive.

Most quotable movie line? “You can’t handle the truth,” from A Few Good Men.

What was the last movie you saw that made you cry? The Pursuit of Happyness.

Most recommended book? American Pastoral, by Philip Roth.

Name one thing that’s overrated: Patience.

Who are you a secret groupie for? Justin Timberlake.

When you’re alone, who do you play air guitar to? I never play air guitar; it’s so not me. But I always sing One, by U2. I sing it to my one-year-old nephew all the time.

What song will be played at your wedding? Forever My Friend, by Ray LaMontagne.

What’s your go-to homemade meal? Peanut butter and jelly.

Fill in the blanks: Vacations are for exploring, not relaxing.

You pull a Ferris Bueller and call in sick on a beautiful July day. What do you do? A round of golf followed by a full body massage.

What Chicago neighborhoods have you lived in? West Rogers Park, Lake View, River West, and the West Loop.

How long is too long to spend looking for a parking spot? Two minutes. I’m very impatient when it comes to parking; plus, you’ll end up getting towed, anyway.

Teacher’s pet or class clown? Teacher’s pet.

Childhood nickname? “Toni” is my nickname; my real name is Antoinette.

What did you think you’d be when you grew up? A talk show host.

Name one thing you have in your house from your childhood: My baby pillow, but I have a ton of that stuff.

And one embarrassing thing you hide when guests are coming over: Nothing. There’s too much to hide.

Describe the state of your closet: Color coded by season and by type of clothes: all pants are together; all shirts are together. It’s pretty organized, unlike my office.

What’s your power outfit? A black pantsuit, and a gray-and-white-striped shirt with white cuffs. And my black Prada pumps.

How much is too much to pay for jeans? No max, if they make my legs look long and lean.

What’s in your pockets right now? I’m wearing pocketless pants.

Have you ever collected anything? I’m starting a watch collection. I’ve been into watches for a couple of years.

Last time you jumped up and cheered? It was last week, when I got the last first-class seat to Portland [on] an oversold flight. Very insignificant things make me very happy.

Last time you told a lie? Do white lies count?

And the last time you Googled yourself? After one of my classmates, who I just reconnected with, Googled me. He said, “You’re a fun Google.”

Worst advice you’ve been given? In college, before spring break: that getting a “base tan” in a tanning bed before going out in the real sun was good for your skin.

If you could give someone a talking-to, who would it be? The IRS.

What do you do when a server at a restaurant brings you a horrible dish? It depends who I’m with. If I’m with my friends, I send it back. If I’m at a business dinner, I eat around it, and go back and order room service.

Gutsiest thing you’ve ever done? I’m doing it now, exposing myself to the readers of Chicago magazine.

What time is your alarm clock set for? Five forty-five a.m.

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

Dive bar or nightclub? Nightclub.

How do you show someone you’re not interested? I’m not very good at that. I usually don’t return their calls. But that’s bad, because it means I’ve already given them my number.

Fill in the blanks: I’d rather have a significant other who isn’t afraid to tell me he disagrees than who agrees with everything I say.

What did you do on your best date? It was an impromptu second date. We scalped tickets to a Cubs game. The Cubs lost, but I had the best time.


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