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What is CheekyChicago.com and how did it start?

Before starting CheekyChicago I was working all of these random side jobs to support my life as an actress, which is how I met my business partner. We were both working at a health club and immediately clicked. We simply liked dressing up, talking, being girls, going to new restaurants, trying new cocktails and drinking wine. We were utilizing the web to explore where we were going to go next so one day we thought, “We should start a food blog about our travels through the city as women trying to live the best cosmopolitan life.” We also wanted to give it this spin of how we became friends and endorse this philosophy of how women should be cheekier. Ever since then it’s been this snowball and very fast process in the last three years. The learning curve has been incredibility steep but we built a brand. We have built a business.

How has starting a business together changed your friendship?

Erica [Bethe Levin] and I were fast friends. She was someone I knew for three months and then we decided to start a business. It was like a fast and furious love affair and then you just elope. Here is the thing about a business partnership, it’s like a marriage. In fact in many ways it’s more intense than a marriage because CheekyChicago.com is my child. I don’t love anything more. I have sacrificed time, friends, family and relationships for my business. That’s how much I love it. To find that balance between what a business partnership needs to feel like and what a friendship needs to feel like has been a very challenging process for both of us. I will say that through the ebb and flow of that experience, she is my life. I love that girl and I know that girl in a way that no one else does. I couldn’t live without her and she would say the same for me. We are rock solid. I would trust her with my life.

Would you say you have your dream job?

Yes, 150,000 percent.

We imagine your office to have pink walls, chandeliers and white furniture.

We are getting there! We have an office, it’s adorable. It’s in the middle of River North. We have the most ridiculously cute little setup. It’s in a big open space so we share a huge floor with a couple other tech companies. We have our own pod.

With all of the socializing, how do you get your rest?

I’ve been known to burn the candle at both ends.  I get colds and get run down. I try to travel regularly. With all of the drinking and eating I do, I have to work out and I have to book nights to stay in because if I don’t, I could go out every night of the week. 

After a night out, what are your tricks for being fresh for the next day?

Always drink a lot of water. Also I use Copacabana by NARS. It’s a shimmer stick that adds glow.

Are you a “Real Housewives” fan?

Obsessed.

Most cheeky housewife?

Bethenny Frankel. Everything she has accomplished, it didn’t fall from the sky. It was something she earned and worked really hard for.

What is something you’d say is un-cheeky?

Non-receptiveness. If I’m in the women’s bathroom at a restaurant and there is a girl in the mirror next to me putting on her lip gloss and I look at her and I say, “I love your lip gloss,” or, “That is a great bag,” the un-cheeky thing to do is to shrug and say, “Thanks.” The cheeky thing to do is to say, “Thank you! I got it at NARS, it’s this color and you should buy it!” Unfortunately, women are non-cheeky in those settings. I think it’s so simple and you can make someone’s day by complimenting their fabulous makeup or their beautiful sweater or whatever the case may be.

How do other cities compare to Chicago in terms of cheekiness?

I think we are the cheekiest. In general Midwest women are really cool. If Chicago was warm every single day of the year we’d be the most crowded city in the world.

Are you dating anyone?

I am a single Sally!

How have you changed since creating CheekyChicago.com?

I always say that this experience of starting my own business has been my real life MBA. I’ve learned it on my own, nobody taught me. I googled marketing proposals and wrote them from scratch, now I have templates that I wrote and send employees. It’s a totally different ball game. I have changed exponentially.

What’s next?

We just launched the Cheeky Card. It enables our audience to live a cheeky lifestyle every single day. We want to grow that to a national program and go from there.

If you could have a drink with anyone, who would it be?

Lady Gaga. I think no matter what you do in your life you should live it with no apologies. She is the icon for bravery.

Photography by Neal Agustin

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