Meet Jessie Lynn: Award Winning Independent Country Music Singer & Songwriter

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Meet Jessie Lynn: Business Owner and Country Music Singer & Songwriter

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Today I am excited to share a success story interview with Jessie Lynn who is a talented country music singer and songwriter. Jessie created her first business at the age of 15 (Wow!) and created two other businesses while pursuing her master's degree. Jessie shares with us some of the advice she has picked up along the way, her productivity and time management hacks, and a sneak peek at her upcoming project.


Jessie Lynn


My questions are in bold, Jessie's follow in plain text.

About Jessie Lynn

Tell me a little bit about yourself?

 Well, I am originally from Prattville, AL. and am known as “Alabama’s Singing Cowgirl!” There is an apparent reason for this title! I grew up on a horse and spent my entire youth competing throughout the Southeast in various rodeos, equestrian drill team events, rodeo queens/ princess pageants, and later, all around open horse show events.

At the age of 15, I launched my first company, Alabama Extreme Equine Productions, coaching and training various equestrian students and equine athletes! This company is still in operation today and is credited with my learning the “business mindset” at such an early age! I have often said that “if someone had told me that my horses would play such an integral role in my music career, I would have told them they were crazy…” however, it is so true!

“Alabama’s Singing Cowgirl’s” brand was built long before I even considered pursuing my music career professionally! Aside from singing in church since the age of 3, performing at private events and gatherings, I opened a local 4-H Horse Show event. I was n horseback, carrying the American Flag at the age of 7,  later I was given the opportunity to open the NCAA Division II World Series Game at the age of 11, and the Alabama State Senate at the age of 12, 13, and 14! Music and horses have been an integral part of my life from the very beginning!

What made me decide to start pursuing my music career professionally? Well, my passion and dreams just wouldn’t let me settle for less! In the Fall of 2013, I was starting my college career at Auburn University and kept feeling this “need” to pursue a passion and dream I had always had, to be a Country Music entertainer, singer/songwriter, and business owner.

So, I started researching and building my business, just like I did Alabama Extreme Equine Productions, from the ground up! Later, Dirt to Diva Publishing, LLC was launched followed by my most recent launch of Dirt to Diva Productions, LLC. Now note, this all occurred while I was still pursuing my bachelor’s degree followed by my master’s degree at Auburn University and, yes, I graduated with both degrees and was part of the top 10 percent of the entire graduating class when I received my master’s degree.


thumbnail 2What is one thing you have learned from being successful?

For me, the word success is not defined by any amount of money made, the number of shows I’ve opened, the #1 hits or charted songs that I’ve had, or how many places I’ve traveled. Instead, I define success as personal fulfillment that can only come from a person expressing to you how much your songs, an interview that you did, or a show that you performed at touched and moved them.

 I’ve always said, “I am successful if just one person is encouraged to re-ignite their dream or passion, chase that “crazy” idea down the road, or become inspired to make a difference in their own and others’ lives!” I have learned to place humility and reality at the forefront of my music and just to be me!



Is there a mistake you have made that you wish you could change?

Honestly, the only “mistake” I would say that I wish I could change is to have started writing songs and working with co-writers earlier in life. While this has not hurt me in any way whatsoever, I wish I would have had a little more time in the writer’s room to discover more as a writer versus being a writer and an artist at the same time.


What is the best advice you have received?

Don’t change who you are when what you have worked! Duane Allen with the Oak Ridge Boys once told me to “make this stage your own. Let no one steal this spotlight from you… this is your stage, your time, and your show. Go for it!” So I have!


What advice would you give someone getting started in music?

Do your homework. If you do not like to read, research, dig, and work your hinny off, this business is not for you. The music industry as a whole is hard, and like every excellent business opportunity and dream, nothing is handed out on silver platers. Everything that glitters is not always gold.


Professionally, what accomplishment are you most proud of?

Honestly, creating who I am and succeeding in doing so is what I am most proud of. My first single, Boots N Bling It’s a Cowgirl Thing, led to me opening for the legendary group, The Oak Ridge Boys, just six months after I had dropped the single in February of 2016.

As an independent artist, opportunities such as that don’t just happen out of thin air! Just from that one single, it later led me to open shows for Montgomery Gentry, Jessica Meuse, Shane Owens, and much more! Being able to say that you have been successful being you is a tremendous honor and surreal moment!


Is there something that you learned from the industry that you found surprising?

Yes, I did! When you look at Nashville as a whole, you tend to think of it as an elite bubble that only certain people can get in and out of, but when you really dig in to the roots of Nashville you find that yes, a bubble does exist, but it actually is much smaller than you had initially thought. Everyone knows everyone! It’s crazy at just how small the music community actually is!


Are there any upcoming projects you are working on?

At this time, we do have a pretty exciting project that we are finishing up in the studio, but we’re not spilling the beans just yet! We will keep everyone on our email list and social media sites updated as we grow closer to the release of that project, but I can tell you that following my current single, “I’m Diggin It” we will be releasing another single from this project just to tease you all a bit! It’s going to be amazing!


Do you have any books you recommend? 

As I mentioned previously, being willing to read, research, and learn your business is an absolute must! There are two books that I would recommend to anyone wishing to start their journey on their music career.

The first one is All You Need to Know About the Music Business by Donald S. Passman and the second book is titled Starmaker by Jim Halsey. Both books provide great insight into the industry and may help you identify where you need to begin in pursuing your career!

Time management and prioritization is such a crucial part of daily, weekly, monthly, and annual routine. I don’t know what I would do without it. It’s so funny. I used to keep a written planner to keep all of my “to-do’s,” events, meetings, and lessons; then things started getting a little too crazy for the planner!

My schedule became so busy that I had to resort to another method of prioritizing and scheduling my life. Thank you for the invention of the iPhone and its calendar feature! It is my life, literally! Every single aspect of my life lives on my calendar and is a great feature to take advantage of if you are overly booked and need to have a quick, easy way to access your schedule. It’s a must for all businessmen and women alike!

Fitness, is it necessary for me and a part of my daily schedule? Surprisingly it is not a must-have for me. I enjoy a nap more than I do the gym! Now, when fitness involves going out to the barn and working my horses and doing all of the typical cowgirl things, YES! Fitness suddenly becomes my entire world indirectly!


Social Media

Has social media factored into my success?

I do believe that social media has factored into my success in several ways. With the invention and ever booming success of social media, it has allowed artists, such as myself to reach my fans and followers across the globe!

Not to mention that we can consistently stay in contact with our fans and keep them engaged with shows, promos, giveaways, and more through all of our social media outlets! It indeed is a great tool when utilized in its proper format!


Any mistakes that you see people routinely make?

Yes. I often see artists that feel they need to express their opinions and political views on social media, but what they do not realize is that when you make that mistake, you lose your respect and credibility with numerous fans. I love what Dolly Parton says when interviewers try and trick her into answering questions about politics, “I’m strictly an entertainer. No one cares about my opinions or views. Plus, I have a number of fans on both sides of the spectrum, and I do not want to offend anyone.”

Everyone can connect with me via the following social media platforms:



Final Thoughts


What is one thing you wish everyone knew?

Overall, I want everyone to feel empowered and to have the confidence to follow their heart, dreams, passions, and more! It’s so important that you actually live and enjoy your life and not just exist while living through it.

 Fun Fact

Jessie Lynn

At the age of 21, I owned and operated three corporations. To this day, at the age of 23, I still own and operate the same three corporations! Dirt to Diva Productions, LLC.; Dirt to Diva Publishing, LLC.; and Alabama Extreme Equine Productions!

I love being hired to do motivational speaking at various events for colleges, high schools, church groups, or just about anything! It’s so great to be able to see your work making a difference in someone else’s life. Sometimes you never know what someone needs to hear to inspire them to chase their own


Thank you for interviewing with Your Money Geek.


Recommended Reading 

Seven Habits Successful People and Celebrities Have In Common


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