Rochester Hills, Michigan native Hillary Sawchuk is one of the coolest girls I know. Not because of her impeccable style, charm and wit. And not because she gets to interview celebrities and interesting people like John Legend and Chrissy Tiegen, Candace Bushnell, Adrian Grenier, Richard Branson, and Common. She is one of the coolest girls I know because she had an idea for her dream job and she went out and did everything necessary to make it happen. She is the ultimate #girlboss.

Its easy to look at people on social media and think that their life is so glamorous and exciting and better than yours. The reality is, those people enjoying success most likely busted their #@$ to get where they are. And behind the scenes, its not as smooth as it looks. 

I recently got to catch up with Hillary when she was back in town to interview Josh Linkner and attend the Detroit FUEL conference and hear more about her journey to get where she is. And of course, some of the hurdles she faces, who inspires her and of course, her style essentials! 

{SS}: Can you share with us your career background and when/how the idea for A Drink With came about?

Hillary: I’ll have to tell you the full story over a drink. After graduating from Oakland University I moved to Chicago and I fell in love with the city. I no longer wanted to move to a small town to pursue sports reporting. Since I never got a job in journalism after college I had to take things into my own hands. After saying, “a drink with,” over and over when explaining the type of interviews, I purchased and all of a sudden I was booking interviews, launching a website and falling in love with every minute of it. I also quickly realized I was more interested in personal questions and chatting as if the interview subject was a friend. I didn’t want to spend my life getting predictable and safe sound bites for a news station. I enjoyed the thrill of thinking of questions that hadn’t been asked before and good, quality conversations.

{SS}: What inspired you to leave your job and go at it full time?

Hillary: I went to school for broadcast journalism. I moved to Chicago from Detroit and took a sales job just so I could live in Chicago while looking for a reporting job. 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. As soon as “A Drink With” took off it was the only thing I could think about it. There was no hesitation to quit my full-time job because I finally had something I believed in so much that I would find a way to make “A Drink With” work. It has been four years and now that I’ve built a brand I am looking forward to expanding beyond Chicago. I am excited to highlight all of the exciting things happening in Detroit. I am looking forward to sharing the stories of the hustlers in Detroit making things happen.

{SS}: Who were the key people that helped you when starting your business and how did they help you? Were there any resources for startups/new businesses that you took advantage of? If so, which ones?

Hillary: My parents and my uncle helped me when I started my business. They were the first ones I turned to when I wanted to share a business plan, needed help finding an attorney, etc. There were also so many entrepreneurs in Chicago who were so kind to give their time and meet when I needed advice.

{SS}: SIDENOTE: her uncle is one of my personal mentors too!

{SS}: Which business women, entrepreneurs, etc. have inspired you and why?

Hillary: Joan Rivers has inspired me so much because she never stopped working hard. “Joan Rivers: A Piece of Work” is my favorite documentary.  Sheri Salata, the former president of OWN, is also such an inspiration. She once said, “Do work that you love, for people you love, with people you love,” and I can’t get enough of what she has to say.

{SS}: Can you share with us any lessons learned or business advice you have gained throughout your journey as an entrepreneur?

Hillary: Make sure what you’re doing doesn’t feel like work. You’ll be spending many hours on your endeavor and need to be okay with not getting paid for it. 

{SS}: What do you love most about your job?

Hillary: My favorite part of the job is the moment I truly connect with someone during an interview. When I forget there are cameras around and I feel like I’m getting to know whomever I’m talking to on a personal level.

{SS}: I’m sure most people think your job sounds so fun – interviewing celebrities and influential people, having drinks in cool places, etc. Can you share with us a few of the behind the scenes disasters that you have dealt with and some of the aspects of the job that you don’t love so much?

Hillary: Not every day is a martini with John Legend and Chrissy Teigen. Some challenges in the beginning (and still today!) were deciding what to spend money on for the business, paying your bills when you don’t get a paycheck every two weeks, learning to not take rejections personally and not being able to shut off work when you work and live out of your studio. 

{SS}: Of all of your interviews, which one stuck with you the most and why?

Hillary: It’s almost impossible to pick just one. I learn so much from each interview and have also made lifelong friends. I definitely won’t forget having tea with Richard Branson. He was fun!

{SS}: Your secret to work/life balance?

Hillary: I love what I do so much that I don’t feel like work and life are separate. However, working out, getting good rest and eating healthy as much as you can is important. I try to do activities that take me away from my phone, so it’s actually impossible to take a peek. The best feeling is getting out of a boxing or spin class and realizing you weren’t thinking about a certain work issue for a solid hour. I also like to go back to my parents’ house for a break from the city.

{SS}: Who is on your wish list to interview? Why?

Hillary: I’d love to interview Oprah. Not only does she seem like someone you could learn so much from, she seems like she would be a lot of fun to have a drink with!

{SS}: And we can’t not ask – what is your favorite drink?

Hillary: Champange, St. Germain and soda.

{SS}: You travel all the time for work. What are your current favorite go-to product(s) when you are on the road? 

Hillary: Bose noise cancelling headphones (QuietComfort 25 Acoustic).

{SS}: What are your top 2 or 3 travel tips?

Hillary: Plan your outfits in advance, only pack what you need and never leave your bag on the hotel floor (bed bugs… gross!)

{SS}: What do you typically pack for these work trips? Any tips to make packing for work easier?

Hillary: In order to fit everything in a carry-on I usually pick one jacket that is my look for a trip: either a leather jacket or a blazer. Something you can dress up and wear to meetings, but also wear on the plane.

{SS}: What are you currently listening to?

Hillary: “Lemonade.” However I’ve listened to the album so much I think I need a break.

{SS}: What are you currently reading?

Hillary: I always have the latest issue of Inc. magazine in my bag.

{SS}: When you aren’t traveling for work, what is your favorite travel destination?

Hillary: My cottage in Northport, Michigan.

{SS}: In regards to your personal style, do you have a signature accessory? (i.e. hat, bracelet, one of your pieces you always wear)?

Hillary: Lately I can’t stop wearing my Adidas Stan Smiths with everything. I also love a black turtleneck in the winter. My Detroit Tigers hat is also a staple. You can’t go wrong with a baseball hat, jean shorts and white t-shirt in the summer.

Left to Right: Adidas Stan Smith Sneakers $75, Splendid Black Turtleneck $85, Red Jacket Detroit Tigers Ballpark Hat $25 Caruso Caruso, IRO Luciana White Tee $81 Sam & Lex Boutique, Distressed Denim Shorts $44 Cotton and Copper Boutique

{SS}: A few items in your "Styleshack" A.K.A closet that you can't live without?


  1. I’ve had a classic Nicole Miller black dress for almost 10 years that is my go-to black dress if I have nothing to wear.
  2. My Sandro leather jacket. You can wear it any time of year.
  3. Grey Ralph Lauren cardigan. I think I stole this from my aunt’s closet. Another item that is over 10 years old.

Sandro Leather Biker Jacket $391.30, Nicole Miller Cap-sleeved Ruched Dress $101, Acne Studios Oversized Alpaca & Merino Wool Cardigan $400

{SS}: Who inspires your style?  Favorite Style Icon?

Hillary: Victoria Beckham

{SS}: What is your Styleshack Style Profile? 

Hillary: Classic. So true!

{SS}: Favorite fashion, lifestyle, food or business blog?  

Hillary: Chiara Ferragni – The Blonde Salad

Photo via The Blonde Salad

{SS}: Favorite local (Chicago) places to shop?

Hillary: Lori’s Shoes

{SS}: Favorite designers?

Hillary: I’ve loved Missoni for as long as I can remember.

{SS}: Favorite place to eat?

Hillary: RL and Fred’s at Barneys in Chicago and Lipuma’s in Rochester Hills, MI.

Photo via: Stu Stuart

{SS}:  Favorite quote or words to live by?

Hillary: Work hard for what you want because it won’t come to you without a fight.

Now you know why Hillary is one of my cool-girl crushes. Join Hillary on her journey by subscribing to A Drink With here and following her on Instagram and Twitter