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

Ashleigh, looking forward to hearing all of your stories today. Risking taking is a huge part of most people’s story but too often society overlooks those risks and only focuses on where you are today. Can you talk to us about a risk you’ve taken – it could be a big risk or a small one – but walk us through the backstory.

Any time you start your own business, you take a risk. Any time you support a start up, you take a risk. Any time you choose a business partner or client, you take a risk. Any time you pursue art as a career, get on a stage in front of hundreds of people, you take a risk. I have taken numerous risks, and risked all of the above. I’ve been lied to, used, “played,” underpaid, lost money, paid for someone else’s mistakes, and made money . . . all as a result of taking these risks. I can say I have failed more than I succeeded, which is part of life’s greatest lesson. I am stronger, wiser, and more resilient for it. The lessons never stop, and neither does risk or opportunity. Now, I calculate risk and its consequences differently.

Ashleigh, 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?

I am a creative business strategist and communicator. I co-founded Level Up Collaborative, a boutique marketing and PR agency, that I now run as a solopreneur. I am a published writer, and am currently a Forbes Communications Council Member. I front several bands, including Ashleigh Chevalier Band, CheDu, Barren River, and Willin’,

Level Up Collaborative creates customized business development and integrated marketing and public relations strategies for small businesses and thought leaders. We have served tech brands, retails stores, restaurants, real estate agencies, creative brands, personal brands, and nonprofits. We are proud to support entrepreneurs and small business owners in their impassioned efforts to serve their communities authentically and successfully.

As a songwriter and performer, I lean into roots rock music for inspiration. I am known for a cross-genre sound, fiery stage presence, and dynamic vocal style. I have released two full length albums, five singles, and have another album scheduled for release early 2025.

The core of all these efforts is a commitment to authentic vision, voice and actualization. We aren’t afraid to be seen and make space for you and your business to be seen and successful.

The same is true for music. As an artist and performer, I embrace the opportunity to share an avenue for genuine expression, introspection, and a deeper emotional experience.

Can you share a story from your journey that illustrates your resilience?

I have been an entrepreneur since I was 14, and I didn’t even know it. I simply started pulling weeds for a friend’s mom, and by 21, I had my own landscaping business and clients. At 23, I went through a divorce, but still managed to be published in UPI while studying PR in London and launch an underground music circular and website highlighting all the live music in a little town called Fredericksburg, Virginia. I started my first band, started teaching music lessons, booking talent at over 12 venues across Virginia, and doing free lance marketing work. I went on to host a music and arts show on Comcast Public Access television and free-lance write for several publications. I earned my B.S. in Marketing from George Mason University, and released my debut album, From the Soles, the following year. I was honored to work alongside Grammy Winner Jon Carroll, featuring celebrated tenor saxophonist, Ron Holloway.

It sounds like a solid beginning after a bad relationship, but I got tangled with the wrong person, that same year and I experienced domestic violence. The pain, turmoil, and shame that follows these incidents aren’t fathomable. I have never been the same. But, I am stronger, wiser, and more resilient.

I now run Level Up Collaborative – a boutique marketing and PR agency that focuses on supporting small businesses and startups. There is a lot to learn as a business owner. I have lost a lot, learned a lot, gained a lot. I am proud of what I do and the clients I serve. I am a Forbes Communications Council member and recently released my sophomore album, Cayenne Roses, after several singles.

My daughter is 11 and thriving in school and ballet. We have a rescue pup, a kitten I found in the middle of the road, two fish and lot of plants. I have found a new passion in CrossFit and weight lifting and am training for a sprint triathlon. We are a happy family, and consider ourselves blessed by God.

We can’t give up. We have to prioritize what will get us through. In my case this is sleep, consistent exercise, and reasonable time off to unwind, write, play music, take in my plants, and connect with others. The balance of these things with the high demands of work is the only way I have been able to process and move through the strain of the past and realize the true, magnificent future that is possible for us.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

“You’re too much. You’re too opinionated.”

There is no such thing.

Society slings this around to men and women, but women experience it differently because there are a different set of deep rooted cultural expectations. A person’s inability to handle another is that person’s issue. I am not talking about discernment, timing, or professionalism. We must all discern, for our own sakes, really. I am talking about authenticity and courage.

I have always been extroverted, strong minded, and persistent. These traits have carried me on and off stages for music and for business. I am not afraid to think for myself. I am not afraid to be wrong. I am not afraid to mess up. (And, I have! Ask my pillows! There are so many stories with tears within them.) I balance this with a pursuit to be introspective, mindful and gracious. But many times, it is the grit that gets me through the things most people won’t dare to do. It is the grit and my faith that pick me up off the ground when I feel absolutely defeated. It’s the conviction I have and the fierce energy within that will not let me give up. That doesn’t make me “too much” or “too opinionated.” It makes me courageous and strong, with a high capacity to achieve and do what I must and wish to accomplish. Reframing this has taken my life time. I’m still on that journey.

The pictures included are a light collection from November 2023 to today with clients and in music: Me after running a personal best 5K, wearing Hoss Tabrizi’s t-shirt “Unleash Your Greatnesses,” a selfie with Annette Stone, a female entrepreneur who has owned several restaurants and has been in business for over 20 years, in the garden of 37th and Zen, where I perform and do the marketing, at a national press conference I supported for Nebula Space Enterprise in Pennsylvania, a photo I took and edited for marketing a newly renovated restaurant, The Green Onion in Norfolk, Virginia, and an action shot from my latest album release in Fairfax, Virginia alongside a dear friend and legend, Ron Holloway.

Contact Info:

• Website: https://levelupcollab.com/, https://ashleighchevaliermusic.com/
• Instagram: https://www.instagram.com/ashleigh_chevalier/
• Facebook: https://www.facebook.com/ashleighchevalierofficial/
• Linkedin: https://www.linkedin.com/in/ashleigh-chevalier-65569b1a0
• Twitter: https://x.com/iamachevalier
• Youtube: https://www.youtube.com/ashleighchevalier
• Soundcloud: https://soundcloud.com/ashleighchevalier

Image Credits

Jim Williams, Jason Hillian (All You Photo), Ashleigh Chevalier,