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A Drink With
People Profiles

Over a Drink, Hillary Sawchuk Inspires Candid Conversations

Published June 26, 2018 by

From Kelly Rowland to Richard Branson and Dan Gilbert, A Drink With uncovers what drives and inspires influencers.

By Ashley Zlatopolsky

Sitting down with industry leaders, influencers, musicians and athletes, Hillary Sawchuk sparks honest, open conversations over a drink. Whether she’s deep in discussion with Richard Branson, the billionaire entrepreneur behind the Virgin Group, or actor Sterling K. Brown of NBC’s hit drama “This Is Us,” there’s one element she aims to uncover in every interview: What drives and inspires people?

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“This Is Us” actor Sterling K. Brown.

“I’m always inspired by those who follow their dreams and have fallen and gotten back up and didn’t stop,” says the 31-year-old Detroiter, who recently moved back to her hometown after seven years in Chicago growing the A Drink With brand. The interviewees each have their own inspiring success story. “That’s what keeps me going, having a real conversation.”

Over beers, cocktails, coffee, tea, smoothies and even milkshakes, Sawchuk and her editorial team of six — along with an army of contractors — conduct interviews with celebrities and up-and-coming talent. The videos they produce have no frills or expectations attached, and the goal is to forget the camera is even rolling. “I thought open and honest conversations were missing in media,” explains Sawchuk, who grew up in Rochester Hills and graduated from Oakland University in 2009 with a degree in broadcast journalism. She had set her sights on becoming a sports reporter — it was her dream. Yet in the locker rooms, she says she noticed conversations “weren’t very meaningful.” That stuck with her.

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Hillary Sawchuk at the Sundance Film Festival interviewing Chloe Sevigny and Natasha Lyonne.

On weekends, Sawchuk sent demo tapes to small markets, hoping to land a job in broadcast. But no one called back with an offer, so she left Metro Detroit for Chicago to take a sales job. “I realized the traditional reporting path wasn’t the job I wanted to take,” she explains. “I started meeting with new people in Chicago over a coffee or a beer. I formed great relationships, and I wanted to start sharing these stories (we had over drinks).”

Casually, a friend called these outings “A Drink With,” and that was the lightbulb for Sawchuk. “It’s simple — you know exactly what you’re going to get,” she says. “The show is about the moments that happen over a drink. You celebrate over a drink; you bond with people. You learn. There’s something about a drink that makes it feel more relaxed.”

A Drink With officially began in 2011. There was no perfect business plan. It was to be tested with trial and error. Sawchuk cold-pitched people for interviews. She saved $500 and bought a logo. Through Google, she learned how to form an LLC. She created a website and called her father, an entrepreneur, almost daily with questions, sometimes crying out of frustration or asking for advice. In the early stages, she continued working her sales job while following her dream on the side. During lunch breaks, she’d step out for photoshoots with people she’d interview.

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Sawchuk interviewing Quicken Loans and Rock Ventures founder Dan Gilbert.

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A Drink With founder HIllary Sawchuk with the cast of “The Land” movie.

“I knew that I could scale this to other markets,” recalls Sawchuk, who now works full time as the platform’s founder and CEO. “It started as A Drink With Chicago, then I dropped ‘Chicago’ because I realized I could take it anywhere.”

She grew the concept by networking and connecting with brands for sponsored content. She aimed to make interviews relatable for readers and viewers so they too could make a connection with someone else’s story. “When you hear that a New York Yankee gets nervous before a baseball game, you realize it’s OK to be nervous,” says Sawchuk, referring to an interview with Curtis Granderson. “You realize that everyone, no matter where they are in life, can learn from (other experiences).”

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Hillary Sawchuk interviewing comedian Chelsea Handler.

Now, A Drink With has produced more than 350 interviews, with everyone from John Legend to Chelsea Handler (her favorite interview). But Sawchuk wants to take the platform to the next level. Being in Detroit again, she has witnessed the changes taking place in the city and sees an opportunity for her brand to align with that growth. “I saw the city in a new way,” she explains. “I fell in love all over again, and I haven’t left since.”

Sawchuk plans on making Detroit the headquarters for A Drink With. “I want to keep interviews going in other markets to keep growing, but I have been so inspired with the people in the city of Detroit and everything that’s been happening,” she continues. “The city of Detroit is not going to give up, and neither are our interview guests. It feels right to make Detroit our home.”

In Detroit, Sawchuk finds a sense of community. “Everyone has this bigger passion to make this city a bigger and better place,” she says. “I just love being a part of that. Something special is happening.”

Read more in 20 Questions with Hillary Sawchuk.

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