Two Friends Get Serious About Being Cheeky

Business /

In 2008, Chicago had the Magnificent Mile, deep-dish pizza, and even Oprah. What it was lacking, apparently, was a website for Chicago women that was definitively bold and saucy.

In 2008, Chicago had the Magnificent Mile, deep-dish pizza, and even Oprah. What it was lacking, apparently, was a website for Chicago women that was definitively bold and saucy.

Enter stage left: Erica Bethe Levin, professional writer and theater major, and Jessica Zweig, professional actor, whose website would fill the void. When they met at the gym, they hit it off instantly and discovered they had a shared passion for dressing up, hitting trendy shows and restaurants, and critiquing their experiences. They just needed a little more cooperation from the Internet. So Levin and Zweig launched CheekyChicago.com in October 2008, a digital hub for the women of the Windy City. It produces more than 35 articles each week, monthly events, a networking community, and a membership program called the Cheeky Card.

 “We’re not just a web site – we’ve really created this community with our events. The monthly events started as an internal marketing tool. We didn’t realize how fun and successful they would become.”

 “Our business is tech-based,” Levin said. “We’re an online magazine; we don’t have a paper product. If you run a website, you need a computer to keep up with the website.” One piece of the tech puzzle is still coming together. CheekyChicago boasts the Cheeky Card program, a VIP program offering perks such as discounts on fitness centers, salons, skincare boutiques, merchandise, food, and cocktails. “We think the Cheeky Card should transition into an app,” Levin said. She envisions something that would list destinations and their perks, and let you know when your friends are there.

Levin believes in “pay it forward” and likes to share advice with startups. The business has been Chicago-centric until now. But Levin and Zweig are ready to put some mileage on their stilettos. “We are a startup, but now that’s it been six years, we’re kind of a ‘standing up,’’’ Levin said. With an eye to the future, they have purchased Internet domains in other cities in the U.S. and Europe. They hope to launch in Los Angeles, Austin … and even Paris.

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