We caught up with the brilliant and insightful Southside Jake a few weeks ago and have shared our conversation below.

Southside, thanks for joining us, excited to have you contributing your stories and insights. Are you able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen?

I’ve had quite the interesting professional and creative journey. I started my career in professional sports and worked on the business side of the Chicago Blackhawks front office for 13 years. During this time I was recording music and doing commercial voice-over work on the side. As amazing as it was to work for such a historic franchise and experience 3 Stanley Cups I realized that my true aspiration was to live full-time off of my creativity. I left the Blackhawks to join Cameo, a celebrity video messaging platform, where I was in talent recruitment and relations. Cameo also tasked me with starting and hosting their podcast, where I had the pleasure of interviewing celebrities such as Lance Bass. I was still actively pursuing my music and voice work at this time and both were gaining a bit of traction. I was able to perform on several high-profile stages such as Lollapalooza, The United Center and The House of Blues. In the voice-over world, I signed to an agency and was and was lucky enough to work with some amazing brands, including being the ‘voice of’ Maker’s Mark whiskey. The creative side of my life and the professional side of my life collided in the best way possible when I joined forces with Songfinch, a custom music company out of Chicago. As the Head of Artist Community at Songfinch I am able to work in music full-time and have the absolute pleasure of assisting thousands of artists and songwriters on their creative journeys. Songfinch has afforded me the opportunity to live my true authentic self.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’m from the South Side of Chicago and a product of the Chicago Public School system. My first love was sports and I was fortunate enough to play basketball and baseball at Rockford University. Wanting to stay in the sports realm professionally, I pursued that path and was able to secure an internship in professional soccer with the Chicago Storm. This led to a full-time position with the Chicago Blackhawks, where I spent the next 13 seasons. My second love was music. Although I don’t come from a family of musicians I do come from a family of music lovers. There was always music playing in the house and I was drawn to it at a young age. At the same time I was enjoying my professional career in sports I was also pursuing my music career under the name Southside Jake. I’m so lucky that my passion and profession have aligned at Songfinch. Songfinch is an amazing platform where customers can commission songs from professional musicians and songwriters. Besides enabling consumers to participate in the music creation process, Songfinch is also creating a middle-class of musicians. In 2022 alone, we facilitated over 150,000 songs and paid out over $ 16million to independent musicians. Music creation is a notoriously difficult craft for artists to monetize, with the top 2% of creators earning the majority of the money while the rest struggle to make ends meet. Songfinch solves for a couple of things simultaneously – creating one-of-a-kind, wow moments for the listener while helping artists monetize their craft.

What do you find most rewarding about being a creative?

I love the fact that something that comes out of an artist’s mind and creativity can have such a deep impact on the listener. Regarding music, people often make comments like, ‘This song changed my life”, or “That album got me through a really tough time.” etc. I find it so interesting and rewarding that something that never existed previously, ie a song, can then be manifested into the world and leave a lasting impact. Quite literally creating something from nothing.

Can you share a story from your journey that illustrates your resilience?

Resilience is a crucial character trait for any independent musician. The music industry can be a challenging and competitive environment to navigate. Let’s be honest, before an artist even begins to figure out the music industry, they have to figure out their music and how to record and release it while building a brand. If you want to be an independent musician, you will release music that only a few people listen to, you will play to empty rooms and at times it will seem like nobody cares. However, if you are creating music for the right reasons, you will eventually start to crack the code and get some traction. I’ve found that getting a small victory – maybe a write-up, maybe an opening slot for a bigger act, maybe a viral moment- fueled me to get through all of the inevitable speedbumps and less-than-desirable outcomes. You just have to keep chipping away. The good news is that if you truly love music, it won’t feel like work and one day you will look up and realize how far you’ve come.

Contact Info:

• Website: https://www.southsidejake.com/
• Instagram: https://www.instagram.com/southsidejake/
• Facebook: https://www.facebook.com/southsidejakemusic
• Twitter: https://twitter.com/SouthsideJake
• Youtube: https://www.youtube.com/@773SouthsideJake/videos