Risk is the most common topic that comes up in our conversations with entrepreneurs and so each week we ask entrepreneurs to talk to us on the record about how they think about risk.

Heather Whiteside | Artist

Being successfully self-employed cannot be without risk, but with skill and conviction in one’s product and/or services and confidence in one’s self, the opportunities are limitless. I rely solely on my own abilities with no guarantee of a return and not a day goes by in my career, that I don’t take risks. However, over the years I have learned to not be overly stressed with all of the uncertainties. Read more>>

Savannah Toal | Houseplant Stylist

Risk is a necessary part of life, especially for your career. You have to discover your line in the sand. I personally feel like risk taking has been apart of most of my life and an even bigger part of what I do now. I was always a bit of a wild card or dare devil growing up. Read more>>

Noah Gibbings | Songwriter

I guess I think about risk like I think about everything in my life: I follow my gut. If it feels right, risk it. Risk is also subjective though. Most of the world would consider me pursing a career in music as a risk. And though statistically that might be true, it is the only thing I am sure of. So to me the real risk would be NOT to follow my passion. Read more>>

Grant Emerson | Web Designer & Developer

Risk taking is an opportunity to challenge myself and grow my skillset and knowledge through taking on work that is adjacent to my current skillset. Whether its agreeing on a Tuesday to play a 4hr cover set on a Friday (I’m a musician as well as designer/developer) or rebranding a business in a sector I have yet to work in, there is always something to learn from each opportunity. Read more>>

Sarah Jameson | Fashion Designer`

I think about risk as an amazing opportunity..I believe that on the other side of risk is great reward regardless if you *fail* or succeed. Risk can seem scary but I truly think the ability to believe in yourself and your skills to take on the challenge at hand implements a level of confidence and pride that can only be gained by facing the uncertainty of risk. Read more>>

Shayla Maddox | Party Rentals and Event Services Owner

Hey! Thanks for having me! Well, if it wasn’t for me ‘taking a risk”, I definitely wouldn’t be where I am today. For a matter of fact taking on several risks. I had to finally let go of a lot of things that were holding me back from my vision. Things that kept telling me no, giving me self doubt or just to hold off for another year.  Read more>>

Bailee Barnett | Singer/Songwriter

Risk is something that is very scary yet very important thing in our lives as individuals. I personally have one situation where I took a huge risk and I would not be where I am at in my life today if I hadn’t taken that leap of faith. I was finishing college in May of 2020 and my plan was to pack up and move to Nashville shortly after that. Read more>>

Carlos Spencer | Writer, Photographer, Filmmaker, Dreamer

Risk can be life or death. Having something practical to rely on waivers the caution of leaping into the dark without knowing where you’ll land, so life has taught me to always have an anchor. Taking a chance on yourself is never a bad bet, but doing so without any idea of the end result or a back up plan, can be your demise. Read more>> 

Patrick Tohill | Film Director

If you’re not putting yourself out there and trying new things you’re never going to learn. Just do it. Read more>>

Sunshine James | Artist/Musician

Every single move you make in the music industry is a risk. Theres no college course, no training, no past reference and no insurance that guarantees success in this business. It’s all a gamble with trial and error. Then after a decade or two you just hope you finally find your place and audience. So I just make sure my overhead is minimal and I am available for any and every opportunity that comes my way. Read more>>

Tracy Silverman | Electric violinist, composer, educator

Well, one person’s risk is another person’s dreams. When I graduated from The Juilliard School, the expectation was that I was well set-up to pursue a career in classical music–if not as a soloist, then as a member of a string quartet or orchestra or as an instructor/professor at the university level. Read more>>

Rachel Swatzell | Higher Education Coordinator & Business Owner

I think about risk as stepping outside of my comfort zone or trying something new for the sake of growing. I feel that I take risks each time in my business as I take a step forward to grow. I took a risk starting my business as a young adult with little experience, especially in the economy coming out of COVID. Read more>>

Tommy Karlas | Professional Country Music Songwriter

I think choosing to try to be a professional country music songwriter was probably one of the riskiest things I could’ve chosen to pursue whole heartedly as a career. More than I even knew at the time I started. When I moved to Nashville at the age of 19 in 2001, there were over 2000 signed songwriters in all of country music. Read more>> 

Kerbi Howat | Business Owner

Before I had kids and, specifically, when I started my business, I was way less risk-averse. For me at the time, the fear of regretting not taking a chance on myself was riskier than the business itself. I was looking for a type of satisfaction in my career that I hadn’t been able to achieve and I needed to take that risk in order to find it (and I did). Read more>> 

Ayanna Jahneé | Musician & Artist

I remember the first time I was labeled as a risk taker. It was for a teacher/student award ceremony and to be completely honest it felt like I was the butt of a joke. Regardless I humbly accepted the award and from then on reflected on what it truly meant to be a risk taker. I started to recognize that I was the type of person to take the unconventional route.  Read more>>

Erica Ross | Creative Entrepreneur

Taking calculated risks is crucial in both our personal and professional lives. I’ve always been a risk-taker, but not necessarily a calculated one. In the past, if something seemed like a good idea, I would dive in without much thought. Read more>>

Madi Hendry | Country Artist & Songwriter

Risk is all about perspective. When I view risk as an opportunity to try something new, it gives me a newfound appreciation for my career. To me, risk is placing a bet on yourself in hopes of the situation turning out in your favor. Read more>>

Ele Ivory | Poetic Pop Artist

I’ve tried to reframe “risk” as unexpected adventure in my life. A few years ago a friend asked me about the balance of staying comfortable & in control while pursuing a creative path; I had never really verbalized my thoughts on this before but I realized that the artistic path is constantly living outside of your comfort zone.  Read more>>