The Chicagolite Spotlight: A Drink With's Hillary Sawchuk

If you could have a drink with any celeb who would it be? I’m sure now you already have a running list of celebs that you wish to meet. Some of you may be willing to give up your right arm to meet Beyonce while other’s just want the opportunity to sit in the studio and have a drink with Kanye. Personally, I wish I could have had the opportunity to meet Freddie Mercury. While for obvious reasons I will never meet Freddie Mercury; this next Chicagolite Spotlight took what many of us would consider a fantasy and changed it to a reality.

Hillary Sawchuk was selected as a Chicagolite Spotlight, not because of her incredibly impressive resume, but because she did what many of us are afraid to do. Hillary took a risk and now the fruits of her labor are evident with her pride and joy “A Drink With” While working a job fresh out of college that she wasn’t quite fond of, she and a friend thought to themselves, who would we have a drink with? From that moment, the rest is history as Hillary has now interviewed hundreds of celebs including John Legend and Chrissy Teigen, Bethenny Frankel, and Richard Branson. When celebs come to Chicago, it wouldn’t be right if they didn’t stop and have a drink with Hillary.

I personally admire Hillary because I found that her story has some similarities to mine. I’m sure other journalism students can relate to this, especially those that are interested in pursuing entertainment. We’ve been told that you have to pay your dues for years before you can work for E! and interview celebs. Professors may say that at a minimum, you probably have to work in a small town for about 5-7 years before you can even think about Chicago, LA or NY. Well, luckily we have examples like Hillary that show that you can create your own path no matter how difficult it may seem. Hillary created the life she wanted and she can only go up from here. Without further ado, let’s get to know the genius behind “A Drink With”

Photo Credit: Kristin Miccoli — Photo Credit: Kirsten Miccoli

TCL: Give us a little bit of background on your early beginnings. What were some of your interests growing up and how did that inspire A Drink With?

HS: Barbies and dress up. I’m not sure how that connects to “A Drink With”! When I was in elementary school I definitely had an entrepreneurial spirit. I went beyond your average lemonade stand. I created a carnival in my driveway where I made root beer floats, raffled off Beanie Babies and set up games to win prizes. I remember I made $80 in one day. I also set up dance recitals in my backyard. I created a flyer and asked all of the girls in the neighborhood to make up a dance. I set up a tent for hair and makeup in my backyard and all of the parents would come and watch. I even went as far as writing lines for a friend to be the host since she didn’t have time to come up with a dance routine one summer.

TCL: “A Drink With” is incredibly innovative, and I’m sure many people think to themselves “Why Didn’t I think of That” When did the idea for “A Drink With” come to you?

HS: Wow, thank you! I went to school for broadcast journalism. I moved to Chicago from Detroit and took a sales job just so I could live here while looking for a reporting job. A friend of mine was in the same position and after a couple of years in the city we realized it was time to do something creative while we applied to jobs. We kept saying over and over, “We could have a drink with…,” and finally we decided to keep it simple and just call it “A Drink With”.

TCL: Your website has seen massive success from covering Sundance to partnering with Virgin Hotels. Share the moment when you knew that you were onto something big. (Your Ah-Ha moment)

HS: I had some interest from investors in the beginning. I think it was at that moment I realized this could really turn into the business I was dreaming it up to be. I’m currently the sole shareholder, but I’ll never forget walking out of some meetings in the early days realizing other people believed in the concept just as much as I did, so much so that they wanted to invest

TCL: As you created your own brand, what would you say have been some of the rewards and challenges?

HS: It sounds corny, but “A Drink With” is my baby! One of the rewards is being able to learn by just doing it yourself as you go. A challenge could be that your personal and business life blend together, you are your brand. Your reputation is important, how you manage your personal finances is important and it can be hard to turn off work.

TCL: We often times say, I wish I knew then what I know now. What is something you would tell your younger self about the journey you are on?

HS: There isn’t anything major. Sometimes you have to just learn the hard way. However, to give some kind of answer I’ll say I wish that I wrote shorter emails. I now try to keep emails as concise as possible.

TCL: Having interviewed many celebs and influential figures, share a memorable moment from A Drink With?

HS: The experiences at Sundance Film Festival with Acura I’ll never forget!

TCL: Your interview subjects are relaxed and so at ease with you. What would you say is the key to bring out the best in your interview subject?

HS: The key to a good interview is making your interview subject feel comfortable. You have to be prepared so you earn their trust and respect, but also you have to be able to go with the flow and take the conversation in a direction you weren’t planning on if you’re having a meaningful, good chat about a certain topic.

TCL: Entrepreneurs all have that story or moment where they knew they were meant to be an entrepreneur. What was the moment when you knew entrepreneurship was for you?

HS: The first day I sat down in my cubicle at my first job after college. Just kidding! Actually, it was that first year. I was unhappy with my job and knew that wasn’t what I was meant to do. I put together a business plan for another business and it was during that planning “A Drink With” came to be. I turned my attention to “A Drink With” and now that I’ve been doing it full-time for 2.5 years I can’t picture my life any other way.

TCL: During your journey, what has been the greatest advice you’ve received and the best lesson you’ve learned?

HS: My boss in Detroit, Jon Witz the producer of Arts, Beats & Eats, told me learning sales skills will be beneficial no matter what career you want to go in. Because of him I took the sales job in Chicago. I now use what I learned at SmithBucklin while selling sponsorships for “A Drink With”, however now it doesn’t feel like sales!