A Drink with Kelly & Hillary

StreetStyleChi sat down with Kelly and Hillary of A Drink with Chicago last week at Floriole over iced tea and coffee to pick their brains about college, careers, and anything else they would throw our way. Alex, Joseph, and Amy, ironically enough, literally had a drink with Chicago.
Where: Floriole Cafe and Bakery
When: January 17th 2013 

ALEX: A lot of people at DePaul are studying journalism, but do not actually want to be journalists, and “A Drink with Chicago” does an amazing job of mixing fashion and lifestyle with all of this cool stuff, how did you come up with such an original idea as “A Drink with Chicago?”

KELLY: We were lucky enough to have really great internships, so I think that’s how we both got into this, and then we moved to Chicago later on in jobs that we really were not too passionate about, just in order to get to a big city, so we were stuck in these sales jobs and all we did was talk about what we wanted to do, and journalism, and then I went home to my little sisters graduation one weekend and the Valedictorian gave a speech, and it somehow inspired me, so I was like why don’t we start a website? It originally just started out as something to do while we were looking for our next journalism jobs.

HILLARY: We moved to Chicago with the intention to find our dream jobs, so once we got here we were like “well we love this city, we’re not leaving”, and as soon as she [Kelly] said “let’s start something” we met the very next day and sat at a bench on the lakefront and just started from there. We knew we wanted to interview people over a drink, and we thought we were going to do all of these other things, but then we realized, you know what, let’s just start with this simple concept.

KELLY: And it’s hard not to model yourself off of something when you’re first starting out, but we decided to just stick with “A Drink With” and it just caught on. It was a happy accident.

JOSEPH: It’s great!

ALEX: Whenever I check your website, it’s always original and that’s what I love. I’m never seeing something that I’ve seen on any other Chicago blog or in any other Chicago magazines. 

HILLARY : Yeah we love all of the other Chicago magazines and blogs, but we see all of these people in the press a lot and it is kind of the same thing or whatever they are currently working on, which is great but we are trying to really get to know these people and Chicago on a personal level. We just want to chit chat, we aren’t trying to break a story. Like what would you just kind of talk about if you ran into that person at a bar? We really hope that’s coming across in these interviews, that laid back feel.

ALEX:  It is definitely coming across.  What would you say your favorite interview is that you guys have done thus far?

KELLY: We always wind up saying the last interview [we have done], so right now it has to be the founder of The Laugh Factory, he has such an inspiring life, it gives me chills. He is such a huge influence, but in such a low key way.

HILLARY: He’s such a private person and nobody really knows that much about him, we talk to people anywhere from 5, 10, 15 minutes, and 45 minutes is a long conversation…we talked to him for almost two hours. He was sent to America by his parents to support his family at a very young age. At one point in his life he was sleeping at the Laugh Factory to make it what it is today, and it kind of inspired us…that we can turn this site into what it could potentially be.

JOSEPH: So what obstacles did you guys have starting out, because I’m sure there are a ton!

HILLARY: Well how much time do you have?

JOSEPH: What would you say are your greatest blocks that you’ve had to overcome?

KELLY: Surprisingly, the easiest part is getting the interviews. We had a lot of trouble with the technical side of this,  like how do we make a logo? How do we build a website?

JOSEPH: And because you were just starting out, you didn’t have a budget to hire people for all of this stuff.

HILLARY:  We had no budget, we broke the bank on our logo, and originally he sent us five versions that were terrible, and we almost just started crying because we had spent almost all of our money. Eventually, he gave us a product, and we love it, but I’ll never forget that.

KELLY: One of them literally had a picture of a saloon and cowboy boots.

HILLARY: So that was a learning experience. Especially the business end of things.

KELLY: I mean we both went to school, but we didn’t learn how to do that kind of stuff. They don’t teach you how to build a website.

HILLARY: It was a lot of googling.

KELLY: We just had to ask people and we would go to events that we knew people we wanted to interview were going to be at and we would just go up to them and chat with them and ask them and they would say yes. We started locally [with the people] and it just got bigger and bigger.

HILLARY: And you know, they know someone who connects us to get another interview and so on and so on. I really think we can say, that from every single interview, we have learned something.

 ALEX: I feel like so many people go to DePaul for the business school and then wind up wandering into something else, so that’s why we love interviewing people like you guys. At DePaul, we’re still trying to figure out what exactly we want to do, and there are so many different, unconventional, options. People think they need to have the perfect internship or the perfect job to go into what their ultimate goal is.

KELLY: I still have so many friends that still want to do things and say “oh it’s not the perfect time,” or something and you know, you’ve just got to do it. I mean we never had the perfect interview or the perfect anything.

HILLARY: It might be a little clunky in the beginning, but you’ve just gotta dive right in.

JOSEPH: Are there certain things you avoid when interviewing people? 

KELLY: We like to show their personality. [the person they are interviewing] We interviewed Jenny McCarthy at a very highly publicized time for her, and every other news outlet was going after that one story when they would interview her, and it’s like why would you ask that? She would just shut down. But in our interview, she was happy and laughing, and talking with us, because we knew not to ruin the interview with that one question.

HILLARY: In our interviews, there’s really nothing off limits, we always go into the conversation with these, I don’t want to say easy questions, but it’s just a normal conversation. When people feel comfortable, they will naturally start talking about personal things and relationships. But our ultimate goal isn’t to get that. We are always so surprised with how much people open up to us.

AMY: Where do you guys see “A Drink With Chicago” going in the future? 

HILLARY: Well, we want to make it into a brand, like “A Drink With…” because we think every city has these cool, interesting, fun, people to have drinks with, and people love to get to know people behind you know, their favorite restaurants, or something so that would be very cool, to expand to other cities.

KELLY: To be honest, we don’t really know. We didn’t really know in the beginning, what this was going to be, we don’t know what next month is going to be. We just know what we do not want to be, for sure, and we know that we want to carve our own path, and not model ourselves after anyone else.

HILLARY:  We know that we want to stick with the concept, of getting a drink with someone, it’s just getting to know people. We know we will be doing video soon, so it will be very different, and very behind the scenes.

ALEX: How would each of you describe your personal style? Sorry, gotta throw this in there somewhere! 

KELLY: I’m very casual.

JOSEPH: I saw you at the E-Drop Off Christian Siriano event, and that was the first time I had ever seen you guys in the flesh, and you guys looked gorgeous. What were you wearing? 

HILLARY: I was wearing a skirt from “Sophia Boutique” and an Americal Apparel body suit. I wear my fur muff thing everywhere, and a leather jacket, and my Nana’s costume jewelery. I love throwing that in. I can tell you what I like to think my style is. I like the preppy, classic…polo. I love a good “pop the collar.”

KELLY: I was wearing [at the Christian Siriano event] an Akira peplum top. I am the anti-hourder. I love going through my closet and getting rid of stuff, that’s why I don’t buy really expensive pieces. I love Zara, Akira, what I’m wearing now is Forever 21, and Nordstrom. I buy nice jeans and shoes though. I’ve never been a label girl.

ALEX: Are there any small boutiques that we can find you guys shopping at?

HILLARY: We love SARCA, and Sophia Boutique.

KELLY: We interviewed Luxury Garage Sale, I love Luxury Garage Sale, like they have the cutest stuff ever! But I love the Sophia Boutique vibe.

HILLARY: It’s very California, like Rachel Zoe.

ALEX: Where is that? I want to go!

KELLY: I think it’s on Oak.

HS: I can’t even imagine being a student in Chicago. You guys must be making the best connections, and having everything at your disposal. Like starting to network so young.

ALEX: Through this blog I’ve gotten to meet so many cool people. And I have the opportunity now to work at E drop-off which is awesome.

KELLY:  Yeah Corri’s story is just so inspiring, she’s great.

ALEX: It’s very cool to see the business side of fashion.

HILLARY: So how old are you guys?

AMY: 21
ALEX: 19
JOSEPH: 19

HILLARY: I can’t even imagine, if I was in college in Chicago and being 21 with Studio Paris and all of these things. 

KELLY: We were very lucky we were not in college here.

HILLARY: I just can’t imagine if I was thrown into Chicago nightlife, in college.

JOSEPH: It wouldn’t be a drink with Chicago it would be “Blackout with Chicago, homeless the next day.”

*Everyone laughs because Joseph is hysterically funny*

ALEX: So one last thing, do you guys have any words of advice for people our age? 

HLLARY: I would say do internships. You know, I was in the locker rooms of professional sports teams, and getting to meet the producers and having access to their cameras and tapes and being able to do demos on the court. After college, that is just taken away, and you’re never going to get that media pass ever again. And, do not be afraid to just go up to people and ask them for advice, or help, or to pick their brain. The second they agree to meet with you, they open you up to all of their connections and truly just learning.
Even still, Kelly and I are at events and stuff and we know “oh, maybe we want to interview them, or maybe they can help us get an interview.” And yeah sometimes maybe it is uncomfortable, but you just have to get over that and introduce yourself.

KELLY: Ever since I was little, my dream was always to work for CMT. I always had in my brain, “alright, what do I have to do to get there?” So I started working at my student newspaper, and I worked at magazines, and I worked at the local ABC station, and then I worked at a publishing company in Chicago. I got local radio experience with a country music station so I would have that on my resume. I built what they would want to see, and eventually I got there. And it was the best experience ever, but it was definitely a series of stepping stones.
You need to start now.

HILLARY: Fake it til you make it.

KELLY: If someone has your dream job, google them. And see what they did to get to where they are. Reach out to them! See if you can chat with them, even if it’s for 15 minutes on the phone.

HILLARY: Stay in touch with the connections you make. If you have an internship and it ends, even six months later, shoot them an email and see how they’re doing. Keep your name in their brains, so then when an opportunity is available at that place, they think of you.

KELLY: And while you are at your internship, pretend you’re an actual employee. If feels really scary, you are around all of these professionals, but they want you to help. And even if you don’t know what you want to do in the long run, that’s okay. My internship experience was so random. One was music, one was radio, one was television, I worked at a magazine and in publishing, so I was always like “shoot, I don’t know what I want to do” but that’s how you find out. Do not feel like you have to do any one certain thing, as long as you are doing something.

*Photos by Joseph Kerins for StreetStyleChi