Whether you’re celebrating a promotion, striking a business deal or unwinding with friends after a long day, grabbing a drink is a social activity that covers all the bases — and Hillary Sawchuk saw that as the ultimate opportunity.
Sawchuk started her website, A Drink With, in 2011 and has since interviewed more than 200 celebrities, entertainers and musicians — each over ‘a drink’ at a local Chicago restaurant or bar. Celebrities like Modern Family’s Jesse Tyler Ferguson, Oscar and Grammy winner John Legend, and Chicago P.D.’s Sophia Bush have dined and drank with Sawchuk across Chicagoland’s favorite spots.
Splash spoke to Sawchuk about her booming success, how to manage your career while drinking seven days a week — and who sipped an entire martini (spoiler: Chrissy Teigen).
SPLASH: How did you originally come up with the A Drink With concept?
HILLARY SAWCHUK: I went to school for broadcast journalism because I originally wanted to be a reporter. I was living in Chicago and had a friend who was in the same boat — we wanted to start a website and we just kept saying over and over again, “We could have a drink with so-and-so, a drink with, a drink with.” So I just said, “Let’s just call it A Drink With.” It was one of those things that just snowballed.
S: Is there any sort of balance you have to strike between keeping your guests comfortable while still getting your questions answered?
HS: You want the interview to be conversational, but if you have fifteen minutes, you can’t spend it all on chitchat; we want it to be questions you would naturally ask over a drink, but at the same time, we want them to share their inspiring success stories. It’s definitely a balancing act. I try not to ask anything that’s been asked before, or [I try to] expand even more. I like hearing about how someone met his or her significant other and then taking it a step further, and asking them the moment they knew he or she was the one.
S: Which celebrity were you either most excited or nervous to have a drink with?
HS: I was pretty excited for Bethenny Frankel. That was exciting and nervous because she was someone [who] I had her Forbes cover printed out, pinned up at my desk — so it’d been five years of admiring how she has built this business. And Richard Branson — I was pretty nervous for him, too.
S: Have you had any awkward moments? Any spilled drinks?
HS: There’ve been plenty. I had my first spilled drink two weeks ago and it was a latte. We’ve done over 200 drinks and I’ve only spilled a latte.
S: How was it interviewing the never-serious Chrissy Teigen?
HS: I still to this day just can’t believe that Chrissy Teigen and John Legend showed up at the time and the place that we asked them to. She drank a whole martini.
S: Do you switch up your drink order depending on who you’re talking to?
HS: I always drink whatever they want — I think it’s fun. I’m willing to try anything. Sometimes I do fake drink a little bit — I’ll just take a little sip and then sometimes people will say, “Oh, I thought we were going to have more than one!” But, this is my job! I can’t always turn off the recorder and have another.
S: Which celebrity made you laugh the most? Or someone who stayed longer than you should have and ended up having a really great time?
HS: The singer, Børns. We brought a bottle of wine to Lincoln Hall and talked to him pre-show, and then we were done he wanted to keep chatting, so we finished our glass of wine [because] we only made it through half in our conversation. Then one of his band members came in [and] we poured him a glass of wine. [That] kind of brought me back to the very beginning — actually really having a drink with someone pre-show and having moments like that.
S: If you could have a drink with anyone in the world, dead or alive, who would it be?
HS: Joan Rivers. I want it to be at her house in New York and I want to have a glass of wine with her.
To read some of Sawchuk’s interviews, visit Adrinkwith.com