We were lucky to catch up with Joshua Allen recently and have shared our conversation below.
Hi Joshua, thanks for joining us today. How did you come up with the idea for your business?
JamSessions Productions didn’t come together in a flash; rather, it was a gradual process of trial and error until one day I realized I had something special. What my business is today is certainly not what it was when I first started.
My entrepreneurial journey began in 2017, during my seventh year teaching middle school band in Chattanooga. While it was a rewarding job, I started feeling the limitations of education and desired to offer the kids I served more opportunities beyond the classroom. For the next 2 years, I initially worked on a nonprofit called “World Music Edu,” which aimed to be an after-school music program providing enriching experiences in music, learning, and team building. Interestingly, I literally called 50 churches, one by one in the area for help. The last church I reach out that I ended up partnering with was walking distance from the school I taught at. They liked my vision and provided the space and access to their after-school program to run the my program.
It actually started off really good, however, running a nonprofit, leading a team, and fundraising proved to be more challenging than I anticipated. Life events such as getting married, buying a house, and changing schools added to the complexity. Eventually, I pivoted the nonprofit into a for-profit private music lessons venture, which was more manageable.
Realizing I needed to commit more time to get this venture off the ground, I left public education in late 2019 and became a full-time entrepreneur, running a private music studio in my basement. However, just as things were starting to take shape, the COVID-19 pandemic hit. By March 2020, I lost all my in-person students, one by one, which was a tough blow.
2020 was a year to stay afloat; teaching online music lessons, podcasting, online music performances on my saxophone and even creating a performing jazz instrumental group. By this time, I was looking for anything that would “stick,” i.e., generate some income during this time. During this time is also where the name “JamSessions” originated. A friend of mine was keeping up with what I was doing, and at the time I was known as Joshua Allen Music on my YouTube channel. He suggested I call myself “J.A.M.” At first, I thought it was stupid. All I could think of was peanut butter and jelly. However, after playing around with it more and adding “Sessions,” it stuck.
BY Mid 2020 i was really into NPR’s Tiny Desk Concerts, I decided to organize my own “tiny desk” via live streaming recording called “Quarantine Sessions” by JamSessions for my band. It was an ambitious project. I did not make any money from it (I was out about $2,500). However, later on, my trumpet player from the band liked what I was doing and asked me to produce her online music performance. Considering I had experience organizing this type of thing for my group, I agreed Only this time, I would be fully behind the camera rather than in front of it. And with that, JamSessions Productions was born.

Joshua, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
It’s actually funny because even though I produced that first performance for my trumpet friend, I was all over the place within the industry. Though I was new to all of it, what I did have was time and the personality type to learn. I remember hearing early on the advice, “Invest not in gear, but in yourself and your learning.” If it was in a book (or YouTube channel), I was reading or watching. My wife can confirm that; I spent many late nights in bed on the iPad soaking it all in. I definitely poured a lot of time and money into online classes and books to learn everything: photography, video production and editing, audio production. It allowed me to cover a variety of things like photography headshots, weddings, events, produce commercials for small businesses, social media posts for non-profits. You name it, I did it. The second piece of advice that I didn’t take, which I should have taken starting out, was to pick a client focus and product and stick with it. This industry is fun and allows you to be creative, however, if it’s not a hobby but a means to produce income, it’s still business. (That lesson took about a year to learn, lol). And though JamSessions Productions has the capacity to do all of it, our main bread and butter is professional video live-streaming and production for performing arts and corporate events.

Can you tell us about a time you’ve had to pivot?
By early 2023, my business wasn’t generating enough revenue to sustain myself, so I had to step back into the W2 world for about 9 months. While it initially felt like a failure and I was uncertain about the future, it turned out to be the best thing that could have happened in my entrepreneurial journey. It allowed me to rest, refocus personally, and redefine my business goals, gaining clarity on what I wanted it to mean in my life and how to achieve those objectives. I also had the opportunity to meet people who came on board to help me with my business. Although my business was treading water to avoid sinking, it ultimately helped me get back on course. For the full story, watch here: https://youtu.be/x9LFL4zF0DY?si=5NYeeaMOz8bwWP36
Are there any books, videos or other content that you feel have meaningfully impacted your thinking?
YES! – Profit First by Mike Michalowicz
– Never Split the Difference by Chris Voss (All-time fav)
– Unreasonable Hospitality by Will Guidara
Contact Info:
- Website: www.jamSessionsPro.com
- Instagram: https://www.instagram.com/jamsessionsproductions/
- Facebook: https://www.facebook.com/jamSessionsPro
- Linkedin: https://www.linkedin.com/in/jamsessionspro/
- Youtube: @jamsessionsproductions
Image Credits
Last Photo taken by HiveThink – Chattanooga Business Accelerator

