Rising Music Star Drew Haley of The Highway Women On The Five Things You Need To Shine In The Music Industry

An Interview With Edward Sylvan


Never give up. It’s true that the roads less traveled lead to the best views but they’re also filled with the most pebbles and stumbling blocks along the way. In other words, it ain’t easy! If it were, everyone would do it and stick with it. I’ve seen a lot of people come and go in this industry.

As a part of our series about rising music stars, I had the distinct pleasure of interviewing Drew Haley.

Singer/songwriter Drew Haley’s East Texas roots flow through her voice naturally with a unique element of soulful sincerity. As a writer, Haley is able to connect personally with her audience through the honest storytelling she implements in her songs. From her experiences with heartbreak, motherhood, and fierce friendship, Haley is fearlessly forging her way down Music Row to the beat of her own drum. Drew has made a name for herself in the country music industry and joined the female-fronted band The Highway Women in September 2019. Drew will be recording and touring with the band in addition to her solo career. Drew’s solo two singles “Fool to Remember” and “Wildflower” have also been featured on Apple Hot Tracks and CMT. She also appeared in several episodes of the hit TV show “Nashville” and is a co-founder of the collaborative initiative “Be a Highway Woman” which was featured in Forbes Magazine in September 2020.

Drew is currently working on a new EP that is set to be released in the summer of 2021, beginning with the single release of “High in Denver” on July 2nd, 2021. “This EP is 100% honest, raw, and created based on some of my personal experiences of being a mom and the highs and lows that go along with this crazy, messy, beautiful, ever-changing thing we call life,” says Drew. Writing songs has always been therapeutic for the singer, and there is nothing more rewarding than sharing her release with others.

Thank you so much for joining us in this interview series! Can you tell us the story of how you grew up?

I grew up in a small town in east Texas. My grandmother has a fishing marina on Toledo Bend Lake and we spent most summers there on the water. I sang 3-part harmony in church with her and my aunt.

Can you share a story with us about what brought you to this specific career path?

I’ve always loved singing since I was a little girl. When I started writing songs at 12, I started to take it more seriously. Writing is therapy for me and I can’t see myself ever not writing songs.

Can you tell us the most interesting story that happened to you since you began your career?

When I moved to Nashville in 2011, I started booking writer rounds for female artists. It was called “Get It Girl Nashville” and it went strong for about 5 years. Back then, I saw right away was women in the industry were not getting the opportunities or radio play that the guys were, so I was determined to showcase the female talent around town. I’m proud of what we accomplished in raising not only awareness about the issue but also funds for nonprofits. We put on many charity fundraisers and also volunteered at the local women’s shelter.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I made a ton of mistakes! I started out singing in bands while I was still in high school in east Texas and then at 18 moved to Austin and played for five years on 6th Street and around town. One bar I played at refused to pay me one night after the gig, so I jumped over the bar and chased the manager down until she finally coughed up my money. Looking back, it was pretty funny because I had to be tough at such a young age. Luckily, my band always had my back! I promise I’m a lover, not a fighter!

What are some of the most interesting or exciting projects you are working on now?

I’m working on finishing up this EP which I’m very excited about! I love recording and the whole process. Releasing your new songs, which are like your babies, into the world is a scary and exciting feeling but I live for it.

We are very interested in diversity in the entertainment industry. Can you share three reasons with our readers about why you think it’s important to have diversity represented in film and television? How can that potentially affect our culture?

This is certainly a hot topic and one that needs to be discussed. Part of what makes this country so amazing in my opinion is its diversity. To have that represented in film/television/music is a given.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

1. Never give up. It’s true that the roads less traveled lead to the best views but they’re also filled with the most pebbles and stumbling blocks along the way. In other words, it ain’t easy! If it were, everyone would do it and stick with it. I’ve seen a lot of people come and go in this industry.

2. Know your WHY. Figure out what that why is and then let that be the driving force behind everything. When you start to lose your way or it gets too hard, come back to it. Remind yourself why and never lose sight of it. I do everything for my kids and for the big dreams I had at their age.

3. Write what you know. Someone actually did tell me this at a songwriter workshop when I first moved to Nashville and it’s always rung true. All writers should remember this golden rule.

4. Always spend the money to have an attorney look over any contracts before you sign! You don’t know everything, so find someone to help you along the way.

5. You get what you pay for! Don’t skimp on the things that matter.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

You have to have a greater purpose in why you’re doing it or you absolutely will burn out. Sometimes you need to take a step back especially if you’re at that point and reassess everything. I’ve done that several times in my career and always come back stronger and more focused.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I just want people to hear my music and feel good. Music is healing and we need it right now.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My parents! They have been my ride or die and are always there to support me along the way. I wouldn’t be doing this without their love and belief in my gifts. They are a neverending support system for my unconventional career path.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Jeremiah 29:11 — “For I know the plans I have for you, declares the Lord, plans to prosper you and not harm you, plans to give you hope and a future.”

I’ve certainly had moments in my career and life in general where I felt like I blew it. I knew I stumbled off the path the Lord had set me on and time and time again, he reminds me of this promise and that as long as I’ve got breath in my lungs, I’ve still got a song to sing.

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. :-)

Dolly Parton! I’m her biggest fan!

How can our readers follow you online?

On Instagram, Facebook, Twitter, and TikTok at Drew Haley Music!

This was very meaningful, thank you so much! We wish you continued success!

About The Interviewer: Growing up in Canada, Edward Sylvan was an unlikely candidate to make a mark on the high-powered film industry based in Hollywood. But as CEO of Sycamore Entertainment Group Inc, (SEGI) Sylvan is among a select group of less than ten Black executives who have founded, own and control a publicly traded company. Now, deeply involved in the movie business, he is providing opportunities for people of color.

In 2020, he was appointed president of the Monaco International Film Festival, and was encouraged to take the festival in a new digital direction.

Raised in Toronto, he attended York University where he studied Economics and Political Science, then went to work in finance on Bay Street, (the city’s equivalent of Wall Street). After years of handling equities trading, film tax credits, options trading and mergers and acquisitions for the film, mining and technology industries, in 2008 he decided to reorient his career fully towards the entertainment business.

With the aim of helping Los Angeles filmmakers of color who were struggling to understand how to raise capital, Sylvan wanted to provide them with ways to finance their creative endeavors.



Edward Sylvan CEO of Sycamore Entertainment Group
Authority Magazine

Edward Sylvan is the Founder and CEO of Sycamore Entertainment Group Inc. He is committed to telling stories that speak to equity, diversity, and inclusion.