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.

Dr. Staci Emerson, Mary Elizabeth Gentle and Alia Tarraf Hidden Star Films | Production Company

Sometimes you have to go after the things you want in life, but sometimes life comes after you. We initially came together to make one documentary film about our friend who died in the prime of her life. The existential tragedy left us each in our own deep waters of grief and questions about the meaning in our respective lives. We all have jobs and family obligations, but this passion project brought us together in a way we hadn’t intended and certainly didn’t expect. We affectionately refer to Allison – the hero of our film – as the woman who brought us together. Around the time we finished Hidden Star, we each came to the realization that though the experience of making the film had ended, it was just the beginning of a different way of looking at purpose in our lives. Read more>>

Chris and Jen Anderson | Co Owners- Balto Farms and Boulder Lavender

Risk has played a huge role in both of our lives. We have chosen career paths where the largest risk was working for ourselves and not knowing where the next paycheck is coming from. The key to risk taking is taking small and incremental risk , so that when mistakes are made, recovery is possible. Managing risk by starting small and growing year over year is the best way to manage risk and the model that we follow. Read more>>

Niki Cicak | Owner of Day Lily Salon and Spa and Author of Thriving In Salon Ownership: What They Don’t Teach You About Owning A Salon

You can’t be an entrepreneur unless you are a risk taker. In fact, I know you can’t. After-all, it’s even in the definition! Merriam Webster defines “Entrepreneur” as one who organizes, manages, and assumes the risks of a business or enterprise. There is no gain without taking risk. Now, you can take educated, calculated, researched risk; but still taking a risk all the same. There is of course some fear that can accompany those risks, but you will never reach your goals without taking the leap. Every day you open the doors to your business you’re taking a risk. But those risks pay off as soon as customer walk through the door. Read more>>

Dylan Donaldson | Owner and Founder of Karing Kind LLC

Risk is an essential foundational component of any business, especially for an entrepreneur. Entering into any new business or even a new job can seem and feel risky. We should never allow risk to dictate the direction we should take any given project, task or business. But we must be ready to take the right risks at the right time to achieve greater success than one could achieve making ‘safe’ decisions. Understanding and analyzing all potential opportunities, even seemingly risky ones, is a great way for a person to develop a sense for the depth of risk versus reward that any particular opportunity may offer. Finding successful opportunities in risk can be a powerful tool for anyone in most any situation. Read more>>

Emma Luecke | Co-Founder of One Life Matters

I believe risk taking — while often uncomfortable — is necessary if we truly want to make a positive and lasting difference in the world. I once read a quote by Christian author and pastor, Eric Ludy, who said, “We should always remember and never forget that those who risk for nothing, commit to nothing, and stand for nothing in the end rarely accomplish anything.” In the biblical account of David & Goliath, there was tremendous risk for a young shepherd boy (David) to go up against the seasoned warrior giant (Goliath). Yet when his brother approached him with both criticism and skepticism, David responded: “Is there not a cause?” Risk taking of course must be coupled with wisdom — but I think the world needs more people like David who are willing to take risks for worthy causes. Read more>>

Peter Freischlag | Artist – Big Moose Studios

Risk has played a significant role in the passionate pursuit of my art. I meet emerging artists at every fine art show I participate in who are hesitant, fearful, or reluctant to take their art to the next level. They are unable to even show me pictures of their work and dismiss their creativity as inferior or unworthy. In the art world, you have to put yourself out there on display and I understand their hesitation, however, the reward is in the journey. My focus has always been on the process and adventure in creating. The outcomes of this endeavor are simply a by-product. Art is about being brave. Read more>>

Bevin Luna | Musician, Music Curator & Small Business Owner

There are so many factors involved with risk. The first thing that comes to mind is uncertainty. When considering risk through my decision making process with my music business, I always remind myself to consider the potential magnitude of the result based on the risk itself. When choosing to pursue an opportunity, I ask myself, “will the uncertainty of this risk present a high probability to propel my business forward? Will this result in a product or a partnership of high quality?” I also think about the likelihood of something beneficial versus something detrimental happening based on taking that risk. Accepted risk is necessary to move forward; however, it can also stifle progress and creativity if risks are taken carelessly. It’s a fine line that requires confidence in the decisions that are being made. Read more>>

Jen Booth | Salon Owner

When thinking about risk I tend to look at the reward as well. Im a big believer in risk vs reward. I feel that risk and reward have to match up. It’s like going to Vegas for example. If you gamble or risk losing $10,000 you have to be ok with the fact that the reward may not be what you think. You have to be ok with losing that $10,000. Since most people tend to avoid risk,I feel those who are brave enough to take risks already have a competitive advantage. For most circumstances the higher the risk the higher the reward. I also like to learn from failed risks by asking myself what’s the lesson here, what would I do different next time. I believe being an entrepreuner is a risk in itself. I also believe that being an entrepreuener can have a big reward as well. Read more>>

Nancy Bratton | Graphic Designer | Artist | Entrepreneur

For me a certain amount of risk taking is a necessary step to have new opportunities, to grow my business, and to learn. Early on in my business I realized that I would have to let go of the comfortable steady on-site freelance work from other design firms in order to be available for my own clients, to focus on their needs and to have time to market my own business. I had to have confidence that losing money in the short-term would be more profitable and more satisfying in the long-term (which it was). Read more>>

J. Marshall | Singer-songwriter

To me, risk-taking seems to the be the whole point of creativity. In regular business, there are ways to calculate risk. You could even say the definition of business is using empirical thinking to minimize risk — “What is the most least-risky, sure-fire way I can make money?” However to me, as a creative, risk is a different thing. What I personally consider to be good creative-work is always derived from genuine originality and expression, and it is always a risk to be your true self in our society. With musicians especially, it is incredibly hard to do your own thing. It’s hard to be yourself and accept the judgement from other people. Read more>>

Melissa Fathman | Executive Director of the Dairy Arts Center & avant-garde cabaret singer

When most people consider risk, they think of risk as it relates to finances or personal safety—two areas I don’t take risks. But the sort of risk that relates to new ventures, concepts and ideas are more related to risk of failure. The first half of my adult life was spent as a performer, when every night had an element of built-in risk of failure—technical issues, forgotten words, missed cues. Over time you learn to be comfortable in that space, excited by the unknown, even joyful with the improvisatory aspects of getting out of a jam. It’s a strange kind of tight rope feeling—a blend of scary and exciting—ex-scare-itement. When I feel that, I know I’m onto something! Read more>>

Chloe Welton | The Art of Aerial Dance

Risk, It’s something that every person must accept for themselves in various degrees and with each new day. I’m sure you know for yourself that doing even the most normal or mundane tasks, like driving and eating, can all have risks that are associated. My name is Chloe Welton, I am Creative Director and Owner of Shangri-La Aerial Arts in Colorado Springs. In my company, life & career, I’ve chosen to regularly evaluate and mitigate my risks as best as possible. Even in an inherently risky profession such as the aerial arts & live performance production industry. My company, Shangri-La Aerial Arts is proud to offer a combination of local aerial dance classes and performing artistry to the surrounding communities and states across the USA! We’ve been providing fabulous entertainment and corporate party services since our establishment in 2017 and we’ve raised funds and awareness for associations such as The Children’s Hospital, Firefighter’s Calendar Fundraiser, the American Heart Association and TESSA’s abuse prevention events. Read more>>

Callie Young | Singer-Songwriter

Risk taking is a huge part of any creative career, especially a career in the music industry. Most industries have a set path, where if you go to certain courses and get a certain degree then you are guaranteed a job in that field. In the music industry, there is no set path to follow to ensure your success. The industry is more about who you know, getting in front of the right person at the right time, the right person coming across your social pages, or the right fans hearing your music and spreading the word. You can be an extremely talented artist, but if you struggle with the other aspects like social media or marketing, you will have a hard time succeeding in music. Risk taking is a huge aspect of pursuing a career in anything where your success is based on what other people think of you. Read more>>

Dayna Safferstein | UX Designer & Freelance Illustrator & Brand Designer

The greatest advancements in my career have happened when I’ve made myself uncomfortable, either unintentionally (by getting fired) or intentionally (by taking a risk). When I got fired from a design job I’d worked at for 3 years, I quickly started interviewing at a small design company that would’ve been a step down in my career. I could almost definitely have gotten that job, but I chose instead to remain unemployed and take a UX bootcamp. This transformed my career and that wouldn’t have happened if I had acted out of fear and taken the first job offered to me simply to avoid being uncomfortable. Read more>>

Valeriya Mushkaeva | Business Owner/ Artist : SoulfulArt

When it comes to risk taking, there are failures, setbacks and even complete start overs along the way. But what I learned is if you don’t risk something, you’ll never gain anything. Take a chance on your dreams and see how life rewards your courageous decision. Prior to embarking on my journey as a mural artist, I had to take many risks in the pursuit of my dreams. SoulfulArt started out as a part-time art hobby. When I started my small business, I was stuck working in a dental profession that did not give me a sense of fulfillment. After graduating dental hygiene school I had a choice to make. Take my exams and begin yet another chapter in the dental field or summon the courage to continue growing my small art business. With Covid delaying all my exams, I took it as a sign to embark on the risky journey of pursuing my dreams as a full-time artist. Read more>>

Leann Nelson | Macaron Baker

I believe that taking risks is so important to getting the life and career you want. I always knew I wanted to own my own business, but I never really knew exactly what it was going to be or look like. It wasn’t until January of 2020 that I decided to start trying to bake French macarons. I experimented with multiple recipes, adjusted the temperature on my oven, and tried many different techniques for months before I finally got them right. I started posting pictures on my social media of my baking progress (even though they were far from perfect), and I had friends and family inquire about me selling them. Read more>>

Patricia Gillmore | Re-Sale E-Commerce Boutique

Risk, that’s a word most small business owners live by or a motto that has been drilled in our head’s the day we created our ideas. Risk-taking to me is “faith” taking that gamble on myself. This is where we as individuals reach deep within and ask ourselves what are we put here to do? Are we here to change something or a system? Are we here to make other’s feel good? Are you here to showcase your unique talent? These are the hard questions, mine was “I am here to give back, and through that, I am here to leave a company longstanding so it may continue to give back long after I am gone” Read more>>

Mallika Chandaria | Artistic Director & CEO of The 98 Art Collective

I think risk is essential. The greatest barrier I face personally when it comes to taking a risk is the presumption of failure. The bitter paradox: whether you stay stagnant or take a leap into the unknown, failure is always a possibility. Given this, I think I would rather fail because of a bold risk, than by remaining the same person. Life is short and precious. I want to fail. I want to make mistakes. That is how growth happens. Risk-taking has been an invaluable aspect of growing up. I took a risk by pursuing the arts (coming from a family and culture that emphasizes traditionally intellectual pursuits). This led to a butterfly effect that resulted in my start-up: The 98 Art Collective. Because of that initial risk, I have had the opportunity to create shows around the world and meet dynamic collaborators. Read more>>

kathryn kalamaras | Artist

Being a dancer, itself, is always risky. Being any kind of artist can be seen as dangerous. Every day we question ourselves, our worth and find ourselves asking all the time ‘Is this worth it?” We realize though that the energy and process is really more important than the destination. The love and drive that goes into something is why we do it. Starting my own company, creating my own full length performance is a risk I’m ready to take on this year. Moving to Colorado was a risk for myself in the first place. I moved here three years ago to pursue my career as professional dancer. Joining my first company was a dream come true, and since then I’ve had the pleasure and opportunity to work with several professional dance companies and performances. Read more>>