Live Shows, Little Voices, Big Heart: How Mom & Musician Jessie Ray Is Building Community Through Music

Interview by Heather Anderson

Photo by Loren Hansen Photography 

Jessika Ray, founder of Jessie Ray Music (JRM), is on a mission to bring unforgettable live music experiences to events across the Bay Area. With a background as a musician, DJ, and music educator, Jessika has built JRM into a dynamic entertainment company that offers everything from live bands and DJ services to music mentorship. We sat down with her to talk about her journey, the inspiration behind her work, and what makes live music so special.

What inspired you to start Jessie Ray Music, and how did your journey as a mom, songwriter, and performer shape this vision?

I’ve always loved to sing, but my formal introduction to music didn’t come until middle school band and high school choir—where my passion truly came alive. Though I didn’t feel prepared to pursue music in college, I continued to develop my skills while earning a degree in Child Development and raising my young family. While my kids were young, I taught music in my own daycare program, and vocal directed community productions. Soon after my youngest entered school, I knew it was time to fully embrace a music career. I started a band, learned to DJ, and became a licensed Music Together® teacher. What began as small steps has grown into what JRM is today: a company that provides high-quality live music and DJ experiences while also fostering a supportive community for musicians. Through Music Together, I also have the privilege of nurturing a love of music in children, bringing my journey full circle by giving back to the next generation.

“Live music creates an immersive experience. It brings people together in a way that a playlist just can’t. When I perform, I get into this zone where I feel completely connected to the audience, and I bring them along with me.”
— Jessika Speer

Can you tell us more about your band, The Vinyl Countdown? What kind of gigs do you play, and how has it influenced your work with JRM?

The Vinyl Countdown is a 70s, 80s, and 90s cover band. We play everything from Madonna and Pat Benatar to Journey and Alanis Morissette. It started as a passion project, but it’s helped me expand JRM into booking live entertainment for all kinds of events. We’re open to community events, private parties, and weddings—really anywhere people want great live music. And I’m also excited to be working on original music, which I hope to share soon!

Your company offers a blend of services, from live music and DJing to music education. How do these elements come together to create a unique experience for your clients?

It’s all about options! Whether a client wants a live band, an acoustic duo, or a DJ, we can customize entertainment to fit their event. For those who want the energy of a live performance but the flexibility of a DJ, we can seamlessly blend both elements. It’s all about crafting the right vibe for the occasion. On the flip side, for those who are interested in developing their music skills, I can be their mentor every step of the way!

You also collaborate with other musicians and DJs. What do you look for in a collaborator, and how do you ensure they align with the high standards of JRM?

I work closely with Heart of Gold DJs, an amazing collective of women and nonbinary DJs in the Bay Area. They have been incredibly supportive and have helped me grow as a DJ. When I collaborate with other musicians and DJs, I look for people who are not only talented, but also professional, and genuinely passionate about creating incredible experiences for clients. JRM is all about high-quality performances and positive energy, so I’m careful about who I bring into the fold.

How did your experience with Heart of Gold DJs help jumpstart your DJ career and influence JRM?

Heart of Gold DJs played a huge role in my launch as a DJ and continues to foster my growth. They welcomed me in, mentored me, and provided opportunities that allowed me to develop my skills. What I love about them is that we’re all independent, yet we support each other. There’s no competition—just a shared goal of creating amazing events. This collective inspires me to bring that same spirit to JRM.

You also teach music classes as a Licensed Music Together® Teacher. How has that influenced your work as an entrepreneur?

Yes! I found Music Together back in 2021 and fell in love with the curriculum instantly, so I became a teacher and started teaching in the North Bay Area. Then in 2024,  I moved back to my hometown of Brentwood, and opened Music Together of Brentwood. I offer classes at Be Exceptional and The Playhouse. Teaching has been a constant in my life, and I love how it connects  our community and the next generation of creatives. Seeing kids light up when they engage with music reminds me why I do what I do.

What’s the most unexpected song request you’ve ever received as a DJ, and how did the crowd react?

I once got a request for "It’s All Coming Back to Me Now" by Celine Dion, which isn’t the most unusual request—but the crowd’s reaction was fire! As soon as I played it, the entire room started belting it out at the top of their lungs. Some of the guys even took off their shirts and waved them around. It was a full-on moment, everyone loved every second of it. That’s the magic of music—you never know how impactful a song can be.

How do you think live music impacts the atmosphere of an event compared to other forms of entertainment?

Live music creates an immersive experience. It brings people together in a way that a playlist just can’t. When I perform, I get into this zone where I feel completely connected to the audience, and I bring them along with me. Whether it’s a DJ set, a live band, or a solo performance, music has the power to transform an event and create lasting memories.

Can you share a memorable moment from one of your performances or bookings through JRM?

One of my favorite moments wasn’t actually from a gig—it was from one of my music classes. A mom told me that her daughter set up a "music class" at home, arranged all her stuffed animals in a circle, and started strumming her ukulele while singing hello to them, just like we do in class. That was such a beautiful reminder of how music sticks with people and becomes a part of their lives.

What’s next for Jessie Ray Music?

I’m expanding! We’re bringing more live music to the Bay Area, and I’m working on writing original music. I’m also looking to bring more musicians into the JRM family to help connect artists with gigs. And, of course, I’m continuing to teach and grow our music classes in Brentwood. My ultimate goal is to open a School of Rock in Brentwood!

How can interested artists or clients get involved with JRM?

If you’re looking to book live music or a DJ for your event, or if you’re a musician looking for gigs, you can connect with me in a few ways:

You can also find Jessika Speer (aka DJ Jessie Ray) on The M List, The Mamahood’s searchable database of mom-recommended resources, or connect and collaborate with her inside The Club membership for women founders.

Heather Anderson