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Rising Stars: Meet Sydny August of Chicago

Today we’d like to introduce you to Sydny August.

Hi Sydny, we’d love for you to start by introducing yourself.
Music has always taken part of my existence in some form–through singing and recording; piano, vocal and ballet recitals when I was younger; creative writing; listening to jazz on vinyl with my dad–music was divinely embedded in my life. Singing felt like it was part of my identity and most of the time it speaks for me.

When I was 12 I started posting covers accompanying myself on YouTube–before this I would write original songs in my room on my electric keyboard. I wasn’t particularly the best at academics and music made me feel like I had purpose and something worth sharing. So, when applying for high schools in my city (Chicago), we take placement exams-naturally, freaking me out. The only high school I was accepted into was one that I auditioned for to take part of the music program. Since then, each year I learned about theory, took up percussion in band, and ultimately choir and performances. This is where I realized I want to make music more independently. From posting YouTube videos to recording on Garageband for SoundCloud, to meeting other creatives and artists in Chicago’s Underground music scene, I began performing at local venues and building relationships with producers, radio stations, and local blogs.

The Underground scene was a community I never thought was possible to be part of, and continuing to meet more local artists to this day. Upon graduating high school, I decided to leave the city to attend the University of Kansas. I studied Creative Writing and Business; set up my home studio at the dorms and later, the room in my apartment. From here was the beginning of my beautiful, little career (posting onto SoundCloud and performing at different local venues). Being back and forth from Chicago to Kansas, I met my best friend, brother and engineer, Castle. After releasing my first EP ‘6th Floor,’ Castle and I have worked on 11 projects (all streamable)–both in person and virtual sessions.

It was October 2019, senior year began and it was also my birthday. Castle posts a birthday video on Instagram Stories of my singing some Lil Durk songs. I repost and tag Durk, thinking nothing of it. He late reaches out to me through DM asking if I am signed and how he loves my sound. With everything I’ve experienced at home; being an independent artist; performing local venues; knowing how to track myself and distribute my music; I felt it was time to branch out and try something different with my career. January 2020, I was in LA with my dad and manager to meet Durk for the first time and pulled up to one of his sessions. It felt full circle seeing Cole Bennett (Lyrical Lemonade), he recognized me from an audition he was judging in for the opportunity to perform at a Chicago festival. I signed to Only The Family (OTF) the summer of 2020 after releasing my debut album ‘Miss August.’

Durk has been a big brother, supporter, and believer of my musical journey. Signing gave me opportunities to travel and have sessions with songwriters and producers. This gave me insight on recording processes I continue to use to this day. OTF allows me the creative freedom and independence I need to explore my artistry and I’m forever grateful.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
I haven’t necessarily had a smooth road–there are constant “no’s,”; rejections from shows I thought would be perfect for me; expecting reciprocated support from those I show up for and will go out the way for. There’s a reason for everything; I never question why things don’t work out. Another struggle is trying to not compare YOUR journey to someone else’s.

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?
I love to experiment in the studio; challenging myself with cadences, harmonies, writing styles, and beat selections. I want my people and family around me to experience it too. Continuing to put my people on, connect with new creatives or opportunities. I’m most proud of all the work and the discography I’ve successfully produced, and continue to create, with Castle intentionally and soulfully. I’m consistent and authentic, that’s all I can do.

What was your favorite childhood memory?
Most my favorite childhood memories are with my sister, Piper. We would invite my parents to a show we’d put on in our living room, because they had no other choice. Singing Dixie Chicks in the car with my sister and mom. I was a major tomboy growing up, Pip wanted to dress like me. It’s funny because she’s a stylist now and I want to dress like HER! Piper continues to be in my favorite memories because we do so much together and have so much more to do.

Contact Info:

Two women in a room with wooden walls and purple lighting, one working on a computer, the other standing behind.

Young woman with glasses and headphones in recording studio, holding a phone, microphone in front, pink wall background.

Woman singing into microphone with eyes closed, stage lighting in background.

Group of people posing indoors, some wearing hats and casual clothing, with colorful background art.

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