We were lucky to catch up with Keshena Armon recently and have shared our conversation below.

Alright, Keshena thanks for taking the time to share your stories and insights with us today. Talk to us about building your team? What was it like? What were some of the key challenges and what was your process like?

I come from a family of entrepreneurs and business owners and much of what I learned about business was from watching and closely working with those family members. By the time I graduated high school, I knew I wanted to pursue music as a career, but I was also fascinated with business management. My parents promoted education throughout my childhood, and I took business classes while still in high school that led to me earning my first associate degree in small business accounting before 20 years old. Even before taking legal steps and filing the necessary documents, I started offering private piano lessons. In the beginning, it was just me meeting clients at the church that my father pastored. He trusted me to open and close the building which gave me a huge sense of responsibility that I took very seriously. Over time, clients picked up but I realized that music performance and production was also a way to make money doing what I loved.

With over 15 years of musical experience as a singer, organist and music director, I enrolled at the Wisconsin Music Conservatory for theory and jazz vocal classes. This was when I discovered that I could and should pursue music as a career. I knew it would be challenging but so many experiences working in the church, alongside my parents, gave me a drive that I was sure would be beneficial if I stayed consistent. As a young lady in my early 20’s, accounting and early education was heavily promoted. Most thought that me pursuing music as a career was not a good move for a lady so there wasn’t a ton of support, however, over time, many came to see that my career choice allowed me to touch lives in a very special way.
Juggling part-time work as an employee while building my business and managing life as a single mom was not fun. There were a lot of weeks I did not know how I’d make ends meet for my family. I learned that some of the people I deemed ‘teammates’ were only in it for fun and I had to make hard decisions.

After about 15 years of teaching, producing and performing as a supporting musician in bands that performed blues, hiphop, and experimental styles, I ended up taking a step back to recharge and focus. I needed to prioritize my health and well-being while finding stability, which meant letting go of the jobs and gigs that were not conducive to where I wanted to be. It took some time (about 2-4 years) before I started to see and feel the shift. I restructured my business and focused on the elements that brought me joy and fulfillment which is how my band, Shuga Blu, came into fruition. After several years of working with other musicians who did not share the same work ethic and sense of community, I shifted and started opening myself up to the genres that I actually enjoyed hearing and playing; reggae, rock and soul music.

Recruiting the first couple musicians was pretty easy because we’d been already practicing extensively in another band that would rarely play shows. We shared interests in reggae and performing out so I began finding places that would allow us to play. We started as a 3 piece, playing in a tiny piano lounge. We did not have 4 hours worth of music that we rehearsed together, so they’d show up ready to watch for cues and learn songs right on the spot! The adrenaline and good times together is what kept us showing up and, somehow, the trio grew to 7 piece in about a year. I would regularly visit the professors at the college I graduated from and that’s where I’d meet other amazing musicians I would eventually invite to play with Shuga Blu. My vetting process was simple – are they decent humans on and off the stage? If we couldn’t rehearse together without drama or weird incidents, I wasn’t willing to book shows. This absolutely took my business from “running me” to me running it:)

I think the thing I’d do differently, if I was to start my business today, is don’t be so afraid to let go of the things and people who were not headed in the same direction. I spent a lot of time trying to please too many people that did not carry the weight of major day-to-day decisions. I cannot emphasize how important it was to find mentors and experts in music management and performance – even if I don’t know them personally, there is so much information available when we search. The other piece to that is learning how to focus and put into action those things that help the business to scale.

Keshena, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

My dad and his siblings had a gospel quartet group, and I’m convinced hearing my mom and them sing and play instruments as a baby is what caused me to fall in love with composing, producing and performing. The story to how I got in the industry is my dad taught me the C major scale on an organ in the middle of a rehearsal just to get me out of the way – I was around 4 years old then and eventually started playing organ in church around 6. :) Traveling with them and the church choir all over the US primed me for what I am doing today. There’s not one show that I’ve performed where I’m not thinking of them, whether it’s a solo performance or big band, live or studio recording.

Since restructuring in 2019, my small company offers premiere entertainment for festivals, corporate and private events throughout Southern Wisconsin and Chicagoland. Over the last few years, I’ve been able to secure several music residencies as a solo performer in Milwaukee and Chicago, which I am very proud of. I could not have done this without referrals and partnering with talent agencies. I am beyond grateful for those who hire me because it allows me to not only take care of myself and family but extend opportunities to others in the Milwaukee music community. Just about every place I perform, I bring a bandmate – and this has proven to boost morale and performance opportunities. One mission of my company is to provide internships and paid opportunities to music students and enthusiasts. Shuga Blu, the Kenzie & Keshena Duo, and Keshena & Friends are three projects I’ve been able to find much success with and we’re looking forward to growing our fanbase with new show material and collaborations.

Stories I love sharing: the first time I attended a secular concert back in the 90s. I’d only been exposed to church revivals and music concerts in schools before going to see George Clinton and Parliament in Milwaukee, WI. I was used to great music but not such a spectacle! I remember saying to myself, “I want that kind of band.” Seeing so many people on stage, in sync, and moving the crowd completely mesmerized me. I laugh out loud to this day when I think of that show. I was a huge Prince fan so seeing who influenced him was huge. A few years later, I drove to Minneapolis to see him perform a 1 a.m. show and that show left an even bigger mark on me. We stood outside Paisley Park in a line that wrapped around the building. I had no idea what to expect and when I saw him with a full stage of musicians (and that big old Hammond B3), I was hooked. I knew I wanted to be a musician forever and began figuring out what I needed to do to make it happen. I am almost shocked 30 years later, I’m doing exactly what I dreamed. I was blessed to travel to Jamaica with my parents as a teen and I performed there. Somehow, I managed to play keys and sing Bob Marley’s One Love when I traveled to Mombasa, Kenya back in 2023 with the most amazing house band at the Voyager Resort. These three specific moments in time are what propel me to keep going. The excitement, communal experience and pure bliss are what I aim to bring to every single show I book.

Have you ever had to pivot?

There was a period of time I was a church musician, teaching private lessons and performing in blues bands while raising a beautiful daughter who was approaching high school. I remember being depleted and desperate for a change because of the grueling schedules and little to no fulfillment even though I was doing what I loved. It seemed like a hit some sort of imaginary ceiling and I couldn’t advance. I’d been performing with various bands for over 15 years and it seemed like the time and effort wasn’t worth the trouble anymore. I needed to make sure my daughter felt supported and my work schedule had become a huge issue. I decided to step down as the weekly church organist and keyboardist/singer for one of the blues bands in order to free up my weekends and be available for home and family needs. Temp service assignments and referrals for regular music lessons is how I made money and this was a wild time because 3 part-time jobs felt very similar to the schedule I had before.

This is when my life started to rapidly change. The manager of one of the part-time accounting positions I held referred me to a well-known non-profit and I was hired on full-time with benefits. It had nothing to do with me performing musically. It was connected to the arts and engaged my interest in finance. Not only did it allow me to fully support my family financially, I met people that I now consider friends. I worked at the organization for almost 4 years before taking an adjunct music instructor position at a local college. It is remarkable when I think of the network of people I’ve been able to connect with, by stepping outside of my comfort zone. Those years of not working ‘in my field’ allowed me to figure out what I wanted my future to look like. Trading the nights of performances for days of business meetings was one of the best decisions I made. My daughter will be graduating college this year with a degree in finance and I’m the happiest I’ve ever been.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

Learning how to use modern technology and navigate through systems are ways that significantly impact the way I move. Another resource that comes to mind that opened my understanding with how to relate to people as an entrepreneur of faith is Relational Intelligence by Dr. Dharius Daniels. It speaks to heart of those who love the people of God and realize their purpose is to serve.

Contact Info:

• Website: https://www.keshenaarmonmusic.com/
• Instagram: https://www.instagram.com/kamco414/
• Facebook: https://www.facebook.com/KAMCO414
• Linkedin: https://www.linkedin.com/in/keshena-armon-71339935b/
• Youtube: https://www.youtube.com/@KeshenaArmonandCompany