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Hillary Sawchuk, A Drink With

Founder: Hillary Sawchuk
Company Description: An online publication that sits down with the most interesting and influential celebrities, artists, athletes and industry leaders one drink at a time.
Company Sitehttp://adrinkwith.com/, Twitter; Instagram
Date of Interview: March 2015

Hillary Sawchuk, A Drink With

Hillary Sawchuk, A Drink With
Art by Brad Lacke

Hillary Sawchuk is the founder and CEO of A Drink With, an online publication that sits down with the most interesting and influential celebrities, artists, athletes and industry leaders one drink at a time. To date, she’s interviewed over 200 individuals including celebrities such as John Legend, Common, Aaron Paul and Daymond John; and has worked with creative partners like Jim Beam, Acura, and most recently, Virgin Hotels. She is building her internet publication one reader at a time, one interview at a time and one drink at a time.

On starting out:
If you check out the site now, you’ll see a sleek, light, modern web page. “We really want our readers to feel like a fly on the wall, and as part of the conversation. We’re really into the photography and we want it to look artsy and feel like a nice magazine.”

“At the beginning, I didn’t know how to buy a domain name; I didn’t know what Tumblr was; I didn’t know what WordPress was. Thank goodness I had a friend, Anthony, who told me I could create a blog for free on WordPress! Then, the spare $250 I had went towards a logo and that just seemed like so much money at the time. Thank goodness for WordPress.”

Since then, the site has gone through two major redesigns and Hillary is already visualizing the site’s next face lift. “It’s always a work in progress.” She reminisces jokingly about how at the beginning, before she learned more about web design, she told her web designer that she wanted to use Beyonce’s website as a model – turns out Beyonce’s web design budget is pretty big… but it’s only a matter of time.

On making it a business:
Since the inception, Hillary knew she wanted to turn A Drink With into a business. Originally, they conceptualized a more traditional ad model to make revenue. Luckily, after watching an episode of Jerry Seinfeld’s Comedians in Cars Getting Coffee​, she was inspired when she noticed that Accura was the sponsor of the series episode.“We definitely didn’t even realize that was a thing!” As a result,[because Acura is a sponsor of the Sundance Film Festival] they reached out to Acura and pitched an interview series featuring the Sundance Film Festival’s actors, directors and producers in attendance.

With every sponsorship that Hillary lands for A Drink With, she gets to work with the sponsoring brand’s creative team and create custom content for their brand, with no traditional web ads. In 2015, A Drink With will be doing one interview a month at Chicago’s Virgin Hotel which you can see on the A Drink With site or on the Virgin Hotel Blog. “It’s really fun to collaborate with brands that align with what we’re doing.”

On what it is really about:
Hillary has the opportunity to interview influential celebrities at the international, national, and local level. Her dream is “to have a presence in every city, and to get to know the up and coming talent and people behind your favorite bars and restaurants.” Even with growing access to big-time celebrities, Hillary always wants to make room to feature the people behind local brands in a city.

“That’s how we started here in Chicago. There are so many inspiring stories out there that aren’t just from celebrities. Don’t get me wrong – I still think it’s awesome to talk to celebrities, but no one is off limits. If someone has a great story that someone else can take something from, and learn something from, that encourages them to follow their own dream – that’s what we’re really all about.”


Looking back, Hillary believes that “everything happens for a reason. I feel like I had to go through some of the lessons I’ve learned along the way so that I can apply them the rest of my life.” Look for Hillary having drinks with all the cool kids at the Virgin Hotel Chicago.

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