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.

Adaire Byerly | Founder, Industry Educator & Neuro Strategist

First, I have to point out that the word ‘risk’ is branched to a negative definition. I focus on that because our association and belief system have a huge impact on words and the way we perceive them. Risk means that there is a possibility that someone will be harmed or in danger. Why is this so important? Because the association with danger is what causes fear, and fear causes us to stay in place. You see our brains are hard wired to choose the path of least resistance or in other words, keep us alive. So “fear” is a very natural experience, we shy away from things that will change our current reality. However, fear and danger are not the same thing. Why? Because fear is inside of you. And danger is outside of you. It is absolutely possible to have no fear but still be aware of the danger outside of you. If we use the word risk, we trigger the experience of fear and If you want to succeed in life, you can not lead with fear. Read more>>

Ash Waters | Entrepreneur

With every high gain there is always a high risk. My whole life I’ve taken risks and high risks, and I gotta tell ya, most of those risks did not paid off. As I mature and I finally get a clearer picture, the risks become “better evaluated”. Growing up I had an extremely hard time controlling my emotions. These emotions would ultimately be the reason my risks wouldn’t pay off. As I have ripened and have learned and better understood how to control my emotions, that then put me in a much better place to win big with my risks. Every day we all take risks, especially with the pandemic we all face. For my brand the biggest risk is obviously failure. The biggest risk for failure is simply “not showing up”! My mentor once told me, “Ash, all you have to do is show up!” “The rest will fall into place” Oh and Ash? “DON’T GIVE UP!” Read more>>

Mat Gurman | Guitarist, Musical Director & Producer

Risk taking is essential. When the big opportunities arise, they often involve big risks and high stakes that can catapult your career is you are successful or set you back if you are not prepared for the challenge. When you are asked to play a difficult musical part on live TV, you can nail it and move up the food chain of A list players. If you are not prepared with the proper skills, you have no business taking that risk because many people are depending on you and the reputation of whoever got you the call is potentially in Jeopardy if you let them down. You won’t get called back. Be honest with yourself when taking risks. If your ready, take it. If not, wait till you feel you are ready for your sake and everyone else involved. Ultimately, it’s the risks that will move you forward and prove what you can be depended on to do.. Read more>>

Quiz | Rapper & Entrepreneur

Risk taking is where you find out what you’re truly made of. It’s easy to perform and execute when things are convenient and comfortable but when you take a risk it’s more difficult to remain mentally and emotionally solid. Risk taking opens the door for fear because you put yourself in position where things can possibly not work in your favor which could set you back. About 8 years ago i took a risk and quit my job to pursue music. Although it was a great experience and it helped me to develop into the artist I am today I also endured some real tough times which have left scars. In hindsight I guess it’s apart of the process but in the moment I questioned my decision often. Read more>>

Jenny Shih | Entreprenuer

The gamble of taking the chance is part of the appeal for my life/career. Risks appear in many different forms and much like other concepts like sacrifice, luck, and the unknown, I think its important to recognize how risks feel within, so that resilience and commitment is grounded no matter what the outcome is. School taught me how to calculate risks with gauging probability, all possible outcomes, and domino effects of the given choice. Life experience has taught me what risks feel like and how to cope with more adversity when facing fears. Some risks can be packaged very nicely, wrapped with ample time and outside resources to minimize the probability of failures. Other risks can be so instantaneous that they call for nothing else but a raw motivation so deeply from within to go for what I believe in. Read more>>

Sei Shimura | Visual Artist & Designer

Risk taking is one thing that all Entrepreneurs have in common, weather it be successful or not. If you have an idea or vision to do something, but your worried that you might fail or have to invest too much money or time to follow your dreams. I have one thing to say. Ask yourself this. Would you rather be working day in day out on someone else’s dreams or your own? Read more>>

Jodee Debes | Wedding & Travel Photographer

My favorite quote is “Life shrinks or expands in proportion to who’s courage.” – Anais Nin Meaning in order to live a large, fulfilling life, you must be brave. You must take risks. I’m constantly grateful for the feeling of nervousness because it signals to me that I must really want that outcome. And what a gift it is to recognize what it is that you want. Mainly so that you better understand the direction you’re striving towards and what risks are essential to getting there. I’m a big believer in failing forward. If you never hear “no” or “try again”, then you’re not reaching far enough. You’re too comfortable. Sometimes it’s nice to live in that space, but not for prolonged periods of time. I personally seek out more nos than yeses in my career because every once in awhile, you’ll get that yes that you didn’t expect that will propel you towards your goal. Read more>>

Marie Pichay | Maker

My business was entirely built off risk. I have no formal training in art or business— I am entirely self-taught, figuring everything out as I go, and putting up my own money for this dream. I started my art page in August of this year and launched my business at the end of September. It all started with me sharing my drawings and designs with my friends. I had the idea to print one of my designs on a postcard to send to my friends during Safer-at-Home and I got a lot of great feedback. I decided to design an entire collection of postcards and get them professionally printed and they were a hit. I sold out twice and have since added a variety of stickers, prints, drawings—and everything has gone well so far. I owe it all to the risk it took to start, and of course to my friends and family who support and show out. Read more>>

Mat Gurman | Guitarist, Musical Director & Producer

Risk taking is essential. When the big opportunities arise, they often involve big risks and high stakes that can catapult your career is you are successful or set you back if you are not prepared for the challenge. When you are asked to play a difficult musical part on live TV, you can nail it and move up the food chain of A list players. If you are not prepared with the proper skills, you have no business taking that risk because many people are depending on you and the reputation of whoever got you the call is potentially in Jeopardy if you let them down. You won’t get called back. Be honest with yourself when taking risks. If your ready, take it. If not, wait till you feel you are ready for your sake and everyone else involved. Ultimately, it’s the risks that will move you forward and prove what you can be depended on to do.. Read more>>

Moriah Boone | Model, Actress & Creative

I absolutely love this question because risk taking is something that I view as vital step on the pathway to success. Far too often I meet incredibly talented individuals that are not happy with where their life is or what they are doing as a career. When faced with the option to take a leap of faith and follow their passion, they falter as a result of fear and uncertainty. It’s the eternal paradox of the “what if” mentality. It’s intrinsically connected to risk taking and it stops so many of us from really going after what we want or even standing up for what we believe in. What if it goes wrong? What if I don’t succeed? What if they laugh at me? You can choose to think of a potential negative outcome or you can choose to believe in all the positive potential. It’s far better to think about how something might just be one of the best decisions of your life instead of thinking about all the “what ifs” once it’s too late. Read more>>

Justin Campbell | Firefly Fabrication Owner

I am not afraid of risk. In the financial world, investors take calculated risks with the expectations of large returns for their endeavors. Acknowledging risk is often associated with higher returns because of an investor’s willingness to leave some of the outcome to chance, which often yields even greater results. I notice a similar effect on my business at Firefly. However, my ability to take on risk and deal with the potential consequences may be more about my personality than a quantitative calculation like in the financial markets. I enjoy the thrill of uncertainty and thrive problem solving when my risk-oriented decisions fail. Seeing everything through a positive lens, even the worst situations, is one of my greatest strengths. This type of risk and failure attitude spans far back to the early days when I was 23 in Florida and started my first hot dog cart The Pickled Sausage. Read more>>

Tara Garner | Construction Photographer

We can’t seem to comprehend what it is about taking risks that includes opportunity, possibility, and prospect, alongside danger, hazard, and uncertainty. The creation of Under Construction Photography started with many risks, and taking chances continues to be a constant in my career. From stepping on site of that first job and asking permission to photograph alongside the workers, to climbing to the top of the 1,070 ft. Salesforce Tower documenting the construction of what is the tallest building west of the Mississippi; my willingness to step out of my comfort zone has allowed for many rewards. My career has been built on calculated risk and requires the ability to jump to action when an opportunity is revealed, literally. My first tower crane climb was not planned for that day, but when I was offered the chance to climb 250 feet to the top, I wasn’t going to let it pass. Read more>>

Jennifer Ridel | Interior/Product Designer, Business Development Consultant & Entrepreneur

Risk is also hope. With maybe a side of delusion. Partly, I had nothing to lose and everything to gain. Coming from a very humble upbringing-the plus side of that-I see now, is the ability to survive & be scrappy and innovate. You’re forced to make shit work, because you have no choice and its sink or swim. I always chose to swim. I never made my upbringing a reason why I couldn’t or would kick ass. Even though I wasn’t sure what exactly I wanted to do, I knew with certainty, what I didn’t want for my life. What gets me going in the morning (other than coffee) is the sense of possibility. Quite literally, anything is possible. How great is that concept? For me, for you. I can do nearly whatever I want and provided the time & energy, make what I want to happen and put those wheels in motion. With my work life, in the beginning of my career. Read more>>

Candace Veach | Acupuncturist, Chinese Herbalist & Healer

I think it is important to distinguish between a true risk that puts you in danger and the “feeling” that something is risky because it is asking you to TRUST in your own ability. It is never wise to risk something you can not afford to lose, such as your life, your health, or the well-being of anybody you love. Having sai My first career was in the film business. After applying myself very aggressively in that career for many years. I faced the choice to let go of something I knew well, was good at, and paid well to pursue an interest that meant going back to school. All signs were my success was on an upward path and within a year I’d be buying a house. Letting go of that to respond to a deeper soul-driven desire felt a like I was opting to jump out of an airplane without a parachute. But I wasn’t really jumping out of an airplane. My life was not really in danger. I was going back to school to study Acupuncture & Chinese Medicine and become a holistic healer. Read more>>

Lana Lekarinou | Writer, Director, Designer & Creator

Risk-taking is part of being an artist and the central theme of my award-winning film, “The Sparkle.”   I think in general it is part of the execution in the creative process.  What I had not realized is that creativity can also become a liability. It is something that can not be purchased and therefore a direct threat to those who can’t possess it. At times they will even go to great lengths to suppress it in another. This was the situation I found myself in and it was this journey I wanted to document in my film.  I think many creative women find themselves in circumstances where their talents are squandered, overlooked, and underutilized. Unfortunately, it can take a long time to find the courage and the strength to extricate oneself from certain relationships that are detrimental to the well being of the artist within.  The decision to make the film also called for my taking a big financial risk. My father had passed away and left me some money. Read more>>

Yiming Amy Hua | Art Director & Fine Artist

Risks are part of a balancing act you have to play if you want to do exciting things. I’ve taken plenty of risks in life, including co-founding an experiential marketing agency and putting myself out there as a fine artist. It’s all about how you choose to look at it and how you weigh the consequences, because there is some risk in every decision you make. When people talk about risk, what they’re really talking about is the fear of failure or harm. The way I see it, if something could potentially harm me (like petting a bear), I’ll think twice about it. However, if the risk is failure, I’m much more likely to go for it anyway because I know that even if it doesn’t work out, I’ll learn a lot. For instance, early in my adventures in fine art, I had the opportunity for a solo show at a tea shop. I was so excited! When the closing party came around, I was too nervous and insecure to market it properly, so hardly anyone showed up. Read more>>

Kelly Wackerman | Master Trainer , Founder & Creator

I really owe everything I have gained in starting theLODNONmethod to the first big risk I took in 2015. At the time, I was one of many teaching an exercise technique here in America known as “Barre”. I read a book written by the founder of Barre’s daughter that explained some very interesting twists and turns the technique had taken since it’s inception and reached out to the author to find out more. Intrigued by my questions, I was given direct contact info to this woman that would change the course of my life forever. I discovered that the woman who started barre, named Lotte Berk, had a different version of her work that was living with her only daughter, Esther Fairfax in England. I learned that what I (and many Americans) had been teaching was actually not the Original version of this very effective exercise method. Wanting to know more I was asked to train with her and flew to England to see what I was missing. Read more>>