We’re excited to introduce you to the always interesting and insightful Kailey Tenn. We hope you’ll enjoy our conversation with Kailey below.

Kailey, thanks for taking the time to share your stories with us today Parents play a huge role in our development as youngsters and sometimes that impact follows us into adulthood and into our lives and careers. Looking back, what’s something you think you parents did right?

My family lies at the center of everything for me.

When I was really little I would sit on my Grandma’s lap while she played piano and tap some notes with her. As I got older (and bigger), I transitioned to sitting next to her on the bench. She never took a professional piano lesson, she could just pick out tunes from ear. I would copy her with my little hand an octave up as she played her favorite melodies with both hands down below. Songs like“Fly Me To The Moon”, “The Way You Look Tonight, and “Somewhere Over The Rainbow”. She was the one who bought me my first upright piano so I could keep practicing. We don’t play as much anymore since her dementia diagnosis, but occasionally my family will band together and get her to sit on the bench again. Though my name, her memories, her past has slowly disappeared from her brain, she’s still takes one finger and taps out her favorite melodies. Through everything, she has not forgotten the music. In these moments, as I sit next to her on the piano bench like I first did all those years ago, it feels like she remembers me, even if only for a brief second. I cannot thank music enough for that.

My Dad was just 12 years old when he stumbled across a startup music studio in while walking home from school in Jamaica. The studio itself was small, bare bones, just a few music lovers trying to put things together. Those guys took my Dad under their wing and made him a part of their family. Almost every day my Dad would go mess around with the equipment until he figured it out, eventually becoming one of the regular session engineers. That tiny studio grew to become one of the most prominent studios in Jamaica, Channel One. Music became a center of my Dad’s life and I’m so grateful he shared his passion with me. And though I have since found my own favorite artists and have developed my personal taste, so much of my sound is still rooted in what he’s taught me. Most days, you’ll find us together listening to any genre (albeit mostly Classic Soul/R&B or Reggae) and dissecting the song’s arrangement, production, lyrics, storytelling, everything possible. Whenever I go to write a song myself, that is the thought process I take with me.

My Mom has taught me things that most would not first associate with being a creative, but they’re essential to make it in this cutthroat industry. She’s taught me how to advocate for myself while remaining humble. How to be a leader while remaining a team player. The importance of following your gut, your heart, and never losing sight of your beliefs. I’ve always admired the overall powerhouse she is in her career and day to day life. I strive to be myself wholeheartedly the way she is herself. Outside of these things, she’s also taught me the importance of showing up and the impact that has on the people you love. She was on the sidelines for every softball game, front row for every school award ceremony, and cheers the loudest at any show I have.

The list of influence continues, from studying my Grandpa’s jazz collection, jamming to my aunt’s 80s electronic bops; blasting Fall Out Boy with my sister, singing indie pop with friends. All of these moments have molded me into the artist I am today.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

Growing up on Long Island, I was quite shy outside of my close group of friends. At school, I was often called the “goody two shoes” or “teacher’s pet” by the popular crew and was never one to venture outside the lines (I was too worried about my grades or getting in trouble haha). But like most kids, I was just trying to figure out how to navigate life (and at now 25 years old, that’s still the truth). This is how I discovered my craft: songwriting.

Songwriting has been my compass and my journal since my middle school days, when I began experiencing an array of emotions I had never dealt with before. Friend drama? 6-minute long song. Body insecurity? 8-minute long song. First crush? 10-minute long song 😅 Looking back, those songs were just streams of consciousness diary entries with a few chords behind them. But they opened up a world I could escape into, with the ability to say whatever I wanted, whenever I wanted, however I wanted. It was a chance to take a breath and venture outside the lines I never dared to cross. My family led me to love music, but songwriting made it my passion.

Most of my days after school (and my absurd extracurricular schedule) began to look something like this:

* Step 1: write furiously into my notes
* Step 2: choose some chords and melodies
* Step 3: record myself into my phone using voice memos, the GarageBand app, and the speaker on my terrible wired-headphones.

Today, my 25-year-old self operates more like the following:

* Step 1: Become overwhelmed with some sort of emotion and write it down
* Step 2: Turn the key concepts into melodic lyrics stitched together with chords
*Step 3: Record the acoustic demo in voice memos
* Step 4: Load up Logic Pro on my computer
* Step 5: Add a bunch of production and finalize the arrangement
* Step 6: Antagonize my perfectionist self by playing it over it again & again
* Step 7: Convince myself it’s ready with the help of some peers
* Step 8: Release the song (maybe?)

Comparing those steps side by side, it’s interesting to see how much has changed yet still remains the same all these years later. Sure – the thought process behind the music is lengthier, my creative choices are more intentional, my recording equipment is better; but everything still starts from a feeling. I believe that’s what I’m most proud of, that I haven’t lost the why behind the music’s purpose.

I couldn’t care less about the social media followers or the amount of streams, that’s not the point of music. The most beautiful thing about music is that it brings people together regardless of their background. It doesn’t matter the language you speak, the color of your skin, the amount of money in your bank account, etc. We can bond over the same song, the same melody, we can feel the same even if just for a moment. When I decided I was going to step out from behind the curtain in 2022 and begin releasing these songs I’ve kept to myself for so long, it wasn’t because I overcame the fear. It was because I realized that we’re all experiencing the human condition and maybe something I’ve written is what someone else has been waiting to hear for so long. We’re not alone in our emotions. When I think of my “brand”, I want my audience, no matter how big or small, to find comfort in connection. I make music for anyone who has ever felt anything at all.

Are there any books, videos or other content that you feel have meaningfully impacted your thinking?

Pyscho-Cybernetics (Updated and Expanded Edition) by Maxwell Maltz was a game-changer for me when it came to my mindset, confidence, and approach toward my goals. I’ve always felt a disconnect between my self-esteem and the things I knew I wanted to achieve. I’m someone who likes to dream, problem-solve, and work hard to see things through. But I also woke up most days feeling low, like I was a failure compared to others, like I wasn’t beautiful, all of these overwhelming negative beliefs. This book was eventually recommended to me and now I recommend it to you. From de-hypnotizing yourself from false beliefs to providing actionable items you can take to become the person you’ve always imagined yourself becoming, there’s much to take away. It may not solve all your problems but it may just have you thinking in a way you never have before. And from someone who feels they’ve tried every book, podcast, and tool under the sun, this book has always stood out to me.

What’s been the most effective strategy for growing your clientele?

I’ve found the most success growing my audience from the following two strategies:

1: Playing local coffeehouses, open mics, virtual performances, etc.
* These moments are a chance to connect with the audience face to face, actively grabbing their attention vs. them passively listening while doing chores at home. A chance to speak with them afterwards and get to know them and receive feedback. Don’t get me wrong, it has taken serious work to get over my stage fright; honestly, I still get nervous before performances. It was a big shift to go up on stage myself with just a microphone and my acoustic in hand. I grew up playing percussion with my peers in school band or drums with my jazz band, I was never alone. But I’m learning to have fun and keep returning to my why: music is about connection and those performances are the best moments to make it happen.

2: Playlist Pitching
* This was formally taught to me in one of my music business courses at school (shout out Hofstra U!), but the more I thought about it the more it made sense. If I love to make playlists for random occasions, genres, etc. then I’m sure others do too. If I could get my music into those playlists, I would then be connected to the niche that those playlists represent and whoever is listening to said playlists would likely enjoy my music. Try reaching out to any real user-created Spotify playlists you felt like your music would fit in genre-wise, lyric-wise, demographic-wise (female songwriter, women of color, etc.) and see if they’d consider adding your song to the mix.

Contact Info:

• Website: https://linktr.ee/kailey10music
• Instagram: https://www.instagram.com/kailey10music/