Getting Cheeky in Chicago

When Jessica Zweig and Erica Bethe Levin met they became fast friends. They would go out for drinks one weekend and dinner the next, but it was challenging to find any online city guides that were geared towards women and what they liked to do. Thank goodness for brilliant ideas thought up over cosmos. Meet Jessica and Erica, founders of Cheeky Chicago.

Jessica ZweigErica Bethe LevinALR: How did you and Erica meet? How long before you two created Cheeky Chicago?

CC: Erica and I met at a day job in 2008 and clicked immediately. Over the course of about three months, we bonded over our mutual love for going out and trying new restaurants and would make “girlfriend dates” every other weekend, checking out the city together. We were using the web at the time to explore the city and found nothing spoke to us: we wanted a city-centric, female-centric complete guide to Chicago and couldn’t believe it didn’t exist. We thought to ourselves: “If we want this, other girls must want this too.” So we took a big leap of faith, quit our jobs and launched Cheeky Chicago.

ALR: What were some of the goals for starting Cheeky Chicago?

CC: We wanted to create the ultimate resource for the cosmopolitan girls of Chicago of where to go and what to do, but we wanted it to have a heart, and a community. We created our events based on this philosophy, and our desire to bring women together to network, but also to empower each other. We wanted to inspire women to be kinder to each other. Gossip is gross, being nice is cool. That’s the true mission of our brand.

ALR: Having started our own business recently we’re curious, what was the biggest driving force that created your strong following in such a short period of time?

CC: Not a lot of sleep and a Starbucks IV. JK….not really. Cheeky came up when Facebook and Twitter were truly exploding, so we used social media to our benefit to build our online presence and community. But in all honestly, the city of Chicago is a rather welcoming and collaborative city. When you have a solid new business, have your ducks in a row and put yourself out there with passion and purpose, people really do open their doors to you. We are very grateful for the warmth we received when we first began, and to all those people that simply said “yes” to two girls they’d never met before. It’s really been a gift.

ALR: What are some of your fondest Cheeky moments?

CC: Every anniversary party in October blows my mind. Our 1,2,3,4 and 5 year anniversary events continue to draw out our fan base, new and old, and I’m amazed at how emphatic, loyal and supportive our Cheeky community is.

CC: I also love to recall Blanca, one of our most loyal Cheeky readers. She has not missed one Cheeky event in years…  Blanca came to her first Cheeky event on her own, wanting to connect with new people. She showed up and asked us if it was “okay” to be there by herself. We couldn’t have been more excited! That’s what Cheeky is all about! And a few years later, having found a new community in Cheeky, Blanca sent us a hand written card in the mail, thanking us for so positively impacting and truly changing her life. I could cry just thinking about that.

Cheeky CardALR: What are some of the biggest perks of being a Cheeky card holder?

CC: Wanna reap $2900 a month in value from this bad boy? Yah, you do. The Cheeky Card is our golden goose. It hooks you up at the hottest places in town. I am obsessed with the Edith Hart perk (free champagne, personal styling and 20% off), Maxine (comped champagne & a free deep conditioner), NAHA ($6 season cocktails) and Sunda (a complimentary sushi roll). There’s also Botox, Pilates Sessions, designer shoes and more hookups. I could go on, but you should just buy the card. ;)

ALR: With so many evening and weekend events, how do you and Erica balance your respective work load and family?

CC: To be honest, we’re bigger homebodies than anyone realizes. We do take many nights in (we have to schedule them like we do a meeting, but hey, whatever works). We have a lot of friends and “goings-on” that aren’t Cheeky related, which provides some healthy space. We travel, we take yoga, we cook at home with our boyfriends, we meditate… we definitely make that “balance” a priority.

ALR: Having recently celebrated Cheeky’s 5th anniversary, what are some of your goals for 2014?

CC: We’re launching two new cities this year! More deets soon, but expect to see a LOT of changes at Cheeky.

Whether you live in Chicago or are just planning a visit, make sure to sign up for a Cheeky Card today. You will enjoy instant perks and get to know their network of strong and talented women. There’s nothing cheekier than seeing women supporting other women!

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Posted in chicago decor, chicago dining, chicago lifestyle, chicago shopping, chicago travel

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