From The Mentors Perspective With Hillary Sawchuk

MentorMob has been busy working with a lot of incredible people this year, and today we are excited to highlight someone you should get to know.

The MentorMob team was introduced to Hillary Sawchuk from A Drink With through our friends and collaborators at?the Virgin Hotels. Hillary is a self-made entrepreneur and journalist who created “A Drink With” to put?a unique spin on celebrity interviews by actually sitting down to have a drink with them (makes sense, right?). Her less formal approach allows her interviewees to open up, and more importantly feel more comfortable in an interview setting. The results are consistently enlightening, raw and intriguing stories that remind you of the power of a good interview.

Hillary’s self grown success is something many of us dream of. She quit her job and pursued her passion, a feat that may seem daunting to many. For one afternoon we were able to turn the tables and get Hillary’s story about how she did it.

A Drink With is such a refreshing take on celebrity and mentor perspectives. How did you get inspired to take on a more personal take on professional interviews?

HS: Thank you! I think I knew I wasn’t meant to be your typical sports reporter when I asked the Pistons’ new coach, Michael Curry at the time, if “expectations were too high,” after a losing streak. After all, the Pistons had made it to the Eastern Conference Finals five years in a row, so fans were overreacting. The entire room was silent until coach Curry finally answered— after what felt like an eternity of blank stares on me— and gave an answer that luckily made everyone laugh. I 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.


You have an impressive list of experience behind starting A Drink With. What was the final motivation to stop working for corporate jobs and to start your own company? When you finally did, what was your hardest challenge to keep going?

HS: 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. 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. Some challenges 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. Not every day is a martini with John Legend!


That took a lot of courage, what small piece of advice would you give to someone who wants to quit their day job to pursue a new passion?

HS: 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.


Many people and companies including MentorMob find they have to pivot from their initial vision to find success. Did you experience this with A Drink With?

HS: The vision has always been to have meaningful conversations in a relaxed environment over a drink. I knew I wanted it to be different than the rest of the press. I no longer wanted to be your typical reporter, I was interested in truly getting to know those who were doing notable things. I wasn’t out to get that one sound bite. Collaborating and creating content for brands is a part of the business I didn’t have on my radar in the very beginning. When I started to think about partnerships for the business you could say there was a pivot, but the vision to build an international publication sharing important and interesting stories giving readers a glimpse of what an industry leader is like when the cameras are off and they are relaxing and themselves was my vision from the start.


Do you consider the people you interview mentors? What are the biggest areas in your life do you feel they have influenced?

HS: I do consider the people we interview as mentors! I just soak up everything they have to say about happiness, relationships and business.


Do you consider yourself a mentor? What experiences (business, personal or hobby related) do you reach back to when trying to give someone advice?

HS: I would like to think of myself as a mentor to those in in high school, college and early 20s. I often think about my internships during college — ?one with the Detroit Pistons and one with NBC in Detroit — and how they were so important and what I did to make the most of my time with access to the best broadcast departments in Detroit. I’ve created a business plan, worked through an operating agreement, split from business partners, worked with attorneys and talked to many different types of industry leaders so I feel like I could definitely be someone to talk to if you’re about to go through any of that for the first time.


Running your own company or even being a part of a small company, you have to wear many hats? Were you prepared for this? 

HS: Wearing all of the hats can be overwhelming at times. I’ve tried breaking up my week and playing accountant one day, journalist next day, marketing director the next day, social media manager the following…that didn’t work! If you were to take a peek at my calendar the day is broken down by the hour and each project takes a mind shift. I worked for an event production company in Detroit and had my hands in a lot of different types of projects, so I had been faced with it before so it didn’t come as a shock.


Based on the people you’ve interviewed if you could change your career right now, what would you want to pursue?

HS: If I had to choose a career of someone I’ve interviewed I would pick New York Times Best Selling author Emily Giffin. One of her books was “Something Borrowed”. Who wouldn’t want to write a book and then have Kate Hudson star in the movie? I always thought it would be fun to be an author and check myself into boutique hotels and binge write.


Who was the first and the last person you interviewed? What important things did you take away from that?

HS: One of my first interviews was with Jessica Zweig, the co-founder of and now the president of The SimplyBe Agency. The last interview I did was with Weird Al! Two totally different personalities, but both fun to chat with. I equally enjoyed each of the conversations. I take away something from each and every interview. I am so appreciative of the time anyone gives “A Drink With”.


Totally off topic but if you could learn anything for free starting today, what would it be, and how would you stay motivated to keep learning?

HS: I’ve been wanting to learn Transcendental Meditation. I would stay motivated to keep learning and practicing if I saw results.

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