Conversations with John Brewster

Today, we’d like to introduce you to John Brewster.

Hi John, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers.
My name is John Brewster, and I am a 28-year-old singer-songwriter living out in Denver, CO! Originally from South Carolina, I’ve got an awesome family. My dad is a humble high school teacher and a lover of basketball. He drove me to school every day growing up.

My mom is a go-getter and did whatever she could to be a stay-at-home mom for me and my sister. She did all kinds of cool entrepreneurship jobs along the way, and now is in real estate! My younger sister, Catherine, is truly a best friend, and also lives in Denver! She’s a talented visual artist, graphic designer, and just a good, inspiring human. We recently collaborated at a wedding where I played music, and she painted the scene! So fun.

In general, I feel like I owe it to myself and my family to keep putting myself out there for the greater good. To share, to sing, to inspire. I’ve been so blessed to have come from a loving family. It wasn’t until I was 17 that my grandma handed me my grandfather’s guitar one night and my life truly changed. I was on track to be a college baseball player, but my life completely shifted.

My grandma, Tada, encouraged me to sing and write a song! Out of nowhere, I finally found an outlet that I really connected with deeply. It was also great timing that I was going through a summertime heartbreak, and when I wrote my first song called “Bittersweet.”

Over the last ten years, so much has happened. I dropped out of college to pursue music, my dad fought cancer and WON, and I moved out to Colorado! I went from being a full-time Uber driver to now being a full-time musician. I released my debut album, 42°, in 2021 shortly after moving to Colorado. I’m so grateful and proud of the life I’ve lived so far, and yet, I still want to keep pushing to grow, give, and become more of who I can be.

I feel like I got a late start in some sense. Some people started singing and playing guitar at age 5. I started when I was 16. This really motivates me to work hard and unwrap my gift with a humble dedication. I love it. Some of my early music influences are Jason Mraz, Coldplay, Ed Sheeran, Phil Collins, John Denver, and The Beatles.

Would you say it’s been a smooth road, and if not, what are some of the biggest challenges you’ve faced along the way?
In 2014, I went off to the College of Charleston for school, and after a few semesters, I took a leap of faith, dropped out, and made the decision to start an original band with my friends. We went all in, bought a van, and hit the road for a few years of extensive touring up and down the East Coast.

At the end of 2018, after all the touring, I eventually hit my version of a personal rock bottom. I was exhausted, super broke, and spiritually in a dark place. My first big dream of being in a band and “making it” didn’t work out as planned. I felt like a failure. My dad was going through cancer treatments at the time when I moved back in with my parents.

I was Ubering full-time to get by and had no plan of how to move forward with my life after all the touring. I gave it my all, and it didn’t work out. Now what? Terribly confused and unsure of what to do next, or how to put myself out there again, I started to write more songs just for fun. I slowed down, and really got to know myself for the first time.

Going into 2019, I was finding spurts of inspiration from listening to podcasts, journaling consistently, getting into a meditation practice, and reading… but the thought of dreaming up a new dream and actually taking action invoked a nearly paralyzing amount of fear in me.

Eventually, I worked up the courage to delete the Uber app at the beginning of 2019 and give myself no choice but to dive back into music FULLY. I made a promo video for myself of me singing cover songs, and I started to book solo acoustic shows at local restaurants in the area. A new chapter began. In 2020, I released my first original song, Every Time I Chose It:

Everywhere I go
In my heart, I know
Everything it grows
Every time I chose it.

As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
From 2019 to 2024, I’ve been blessed to have 95% of my financial livelihood come from performing live music as a musician. 

Let me pause to take that in. Wow. This was once a dream… a passing thought… a daydream… and I’m now living that life more and more! A true blessing and opportunity.

Every year, I aim to play hundreds of shows, ranging from private events to yoga classes to original shows, to even Justin Bieber’s wedding in South Carolina a few years back. That was pretty wild and unexpected.

After moving to Colorado in 2021, I released my debut album, 42°. In 2022, I was the featured artist for Trevor Hall’s VIP acoustic show at the Red Rocks Hotel. In 2023, I started to release a series of singles working towards my second album. And in 2024, I released my first full-length concert, COMING HOME, which is available to watch or stream.

You can find all my music and upcoming shows on my website, JohnBrewsterMusic.com

What were you like growing up?
Growing up, sports took up most of my time. I was big into baseball, basketball, and even bowling! I thought I was on track to be a college baseball player, but music slowly took over more of my life.

There were two memorable turning point moments that stood out to me. One was seeing Ed Sheeran play in 2012 when he first began touring in America. A few friends in my class really wanted to go see this “new up-and-coming artist” so I went along with them just for fun. The next day, I felt like my whole world had completely shifted. Going to baseball practice in high school didn’t seem like the long-term plan anymore.

The second memorable moment came the same year when my grandma, Tada, handed me my grandpa’s classical guitar out of nowhere and encouraged me to learn how to play and sing. Things started to shift more directly towards music once again.

The next summer, instead of getting a summer job, I collaborated with other local artists to play live music at restaurants 3-5 nights a week. For the first time, I could see how music could one day turn into a potential job, a lifestyle of an opportunity to pursue with purpose.

Contact Info:

• Website: https://www.johnbrewstermusic.com/
• Instagram: https://www.instagram.com/john.brewster.music/
• Facebook: https://www.facebook.com/JohnBrewsterMusic
• Youtube: https://www.youtube.com/@JohnBrewsterMusic
• Other: https://open.spotify.com/artist/3MX9NAXyBzs5SYSyFmabNl?si=4H4h11OYRxCYwTTTlfkYng