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Life, Values & Legacy: Our Chat with John Covelli of Lakeshire

John Covelli shared their story and experiences with us recently and you can find our conversation below.

Hi John, thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: What is something outside of work that is bringing you joy lately?
I was recently laid off from my fulltime day job, and I was able to put all my time into testing my app, SlideMaster. In that process I became proud of inventing such an app and started to embark upon marketing the app so that I can share it with other trombonists.

Can you briefly introduce yourself and share what makes you or your brand unique?
I’m John Covelli — a trombonist, composer, and creative entrepreneur whose work bridges jazz performance, technology, and storytelling. As the bandleader of Hard Bop Messengers, I blend classic jazz with unexpected influences like the Grateful Dead, transforming familiar songs into improvisational journeys. My concept album Live at the Last Hotel has evolved into a graphic novel project that explores music, memory, and redemption through rich visual storytelling. Alongside my artistic work, I founded Covelli Consulting and developed SlideMaster, an app that helps trombonists “play smarter, not harder” through data-driven insights into slide technique. Whether I’m arranging a modern jazz chart, designing an app for musicians, or helping businesses “JAM” with data, my mission is the same — to fuse creativity, precision, and soul into everything I do.

Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What’s a moment that really shaped how you see the world?
Getting clean and sober nearly 12 years ago, as a 48-year old, I finally started to understand the world around me for what it actually is, versus what I want it to be or think it is. It is a practice I engage in daily to ask a higher power for the wisdom to know what I cannot change and what I might have the opportunity to shape or influence.

What fear has held you back the most in your life?
Fear of not being good enough is a large part of my psyche, and I work a daily program to remind myself I am still learning. I try not to engage in S.H.A.M.E. which is the belief that I Should Have Already Mastered Everything. Instead of criticizing myself I work to try hard to become what I want to be.

Next, maybe we can discuss some of your foundational philosophies and views? What’s a belief you used to hold tightly but now think was naive or wrong?
I used to think that because I didn’t get all the requests to play music, with other musicians as much as I thought I deserved, that it means that I am not good. I have learned to appreciate my musical gifts and be grateful for the opportunities that I get to share that with people.

Okay, so before we go, let’s tackle one more area. Could you give everything your best, even if no one ever praised you for it?
I have ventured out in recent years to lead a band and okay a brand of music in which I believe . Although I get some positive feedback, I would say that I do not receive PRAISE for that. I keep doing it because it is what I need to do.

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Image Credits
Taylor Hobbes, John Schmitt

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