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.

Lisa M Gunshore | Functional Ayurveda Practitioner and Host of Buddhist Biohacker

I have taken many risks in my career and in my life. I have found that when something lands from Spirit in my heart, I have to say yes no matter what. I don’t usually have any idea how to do what I’ve been given but I find a way. I also find that I am often supported by the unseen guides. One of the biggest risk I took was in 2009. I was in a meditation and had a vision of the Dalai Lama. I knew very little about Him and I wasn’t sure how to act on what I saw. I felt called to connect. with the Dalai Lama and was guided to look at his schedule. I saw that he would be speaking in California the very next week. I had very little money but found a ticket on Craigslist for $50. I bought it. A week went by and I happened to have enough unexpected client sessions that I had enough money to buy a ticket. I also asked a friend and was able to split the hotel costs with them. It was amazing that it all worked out. I went to California and saw His Holiness speak. Read more>>

Laura Black | Owner of Mesa Park Vineyards and Real Estate Agent at Fruit & Wine

I would say that most people that know me well would say that I am not afraid to take risks when it comes to business or my career. I would most definitely not be running a winery in Palisade if I was a risk averse person, my husband and I bought Mesa Park Vineyards 3.5 years ago with zero experience in farming grapes, making wine and operating a winery. I’d like to think that most of the time, in my mind and thought process any way, the risks I choose to take are somewhat calculated and are taking me towards my goal of not just being successful but also feeling fulfilled. I have always been an opportunist and have made it a priority to not just move through life but to actually take advantage of adventure and opportunity and sometimes that means people think I am crazy! But if there is anything I have learned, especially jumping from one industry (real estate) for which I had a very successful career to now (winery life), is that if you are willing to put in the work. Read more>>

Vera Anderson | Professional Visual Artist

The entire experience thus far with this art endeavor has been about risk taking. When I was growing up my dad gave me some advice which I have used periodically in my life “just make a decision and don’t get stuck in the what if’s. It’s better to make a decision than none at all. You don’t know what opportunities will be right around the corner. If you end up making a bad decision you will adjust” In 2015 I quit a job with the airlines without another job lined up. But I was ready to start a new chapter in my life and it made all the difference. Read more>>

Shawn Satterfield | Inclusion Architect

For me, taking risks is essential for both personal and professional growth. It’s not about blindly jumping off into the unknown, it requires a deep connection to your intuition…that “gut feeling”. It took a lot of jumps before I figured that out. My first life changing risk was to move to Colorado, away from all my family and friends. Going from a town of 18k to a city of 1.5m was both terrifying and exciting and yet I knew it was where I was supposed to be. After my son was grown, and years of working in corporate America, I started fine tuning that inner voice which was constantly asking me – What is your purpose? In 2017, I Co-Founded a web development company with a fellow peer, specializing in enterprise CMS platforms. Sounds risky, but it was more like jumping from the big pool into the adjacent wading pool. And the persistent voice continued to ask the same question…What is your purpose? Then one day, the voice somehow acquired a megaphone. Read more>>

Calvin Shepherd | Film Director, Screenwriter, Producer

Risk taking is everything for me. I know there’s a look I get every time I say I’m creating another feature when this stage of the film industry really looks to things like music videos, short films, and commercial work, which I do enjoy doing, but I write features all the time. And if it was just writing, I would be stuck creatively. I know it’s a huge risk every time I take on a new independently funded feature film. But I just love doing it. Read more>>

Lucy Wallace | Founder, Dance To Be Free

Walking into maximum security prison for the first time was a risk and very uncomfortable. Meanwhile I feel more anxious parallel parking or running a board meeting. I find that I am more willing to tackle challenges in life that are beyond intimidating. I plow through the rational fears of what could go wrong and focus on the core of what’s needed. In this instance my fear of walking through prison was over ridden with the glaring need for prison reform – a very worthwhile risk! Since that first day of teaching dance in prison I have entered 17 new prisons with some of that initial fear of taking that risk. My fear is always overtaken with the urgency to help the voiceless and invisible. Read more>>

Valdon Ross | Counselor For Creatives, Seekers, & The Inspired

I view risks as opportunities for growth, a way to gather information, a way to learn about myself and the world, and a way to heal. Learning to enjoy risk-taking has allowed me to develop great confidence in my ability to brave existence and the situations I get myself into. Risk-taking is also a great antidote to perfectionism. The point isn’t about the outcome — the point is using my skills and abilities as best I can at a given moment in a given situation. I can always learn and grow from a situation in this way, particularly by learning to respect my limitations just as much as my strengths. This sort of thinking is called a Growth Mindset, and I dig that phrase. I’m always helping my clients develop this sort of outlook on life and relationship to their experience. To me, it is actually about prioritizing my mental health. Read more>>

Samantha Joule Fow | Entrepreneur, Author, & Activist

Recently I was asked about the biggest sacrifice I’ve had to make to be an entrepreneur. The answer that I gave was simple: “security.” I have had to put my own time, energy, and resources on the line to establish and grow my business. It is a process that has taken years and involved countless trials and errors. Even so, there has never been any doubt in my mind that I would succeed – and this is partially because I have been able to make friends with fear. Starting a business is risky, and being fearful of taking such a big step is rational. But in truth, fear can be a great friend. It can help guide direction during new experiences. It can help you understand and assess threats to your professional wellbeing. And perhaps, it may even be the driving force behind your will to succeed in a highly competitive marketplace. Reward seldom comes without risk. For me, the rewards of being an entrepreneur, activist, and thought leader are far greater than the risks I took to get here. As a result, I am grateful for the opportunity to have taken professional risks. Read more>>

Pags | International Superstar

In my humble opinion, I think it is important to take risks – especially when you’re younger. Not many people know this but the illusion of safety is very real… and just that, an illusion. Safety doesn’t truly exist, it’s a constructed concept in our society. In this case, let’s use the idea of safety around a career… no one will tell you this but you can still fail at something you chose to ‘play it safe’ with. At the very least, I’d rather fail on my terms. Read more>>

Lauren May Woodruff | Dressage Barn Owner, Sport Horse Breeder, Business Development Professional & Inventor

The ability and willingness to enthusiastically approach risk in business and life is one of the founding characteristics of all entrepreneurs. We are a breed of people who will sit with the spark of an idea and pour effort, money, time, consideration and drive into it until this small thing begins to breathe on its own. No person at the beginning of the creation process knows if their concept will become a living, breathing business with a life and inertia of its own and yet we all passionately pursue that ending. It’s a special flavor of crazy and without it our society would be without progress or innovation. Through my own creation process with both businesses, The Hillside Center, and RecoverEASE, I jumped into those industries with both feet after having seen a niche in large markets that I could fill. My passion for business development and ability to market those ideas to the consumer had truly overshadowed the risk of failure or rejection that inherently comes with growing a concept. Read more>>

Drew Schaefering | Hairstylist, Cruxe founder, Artist, Co Creator of The podcast “The Strands That Bind Us”

Risk is a funny thing. The saying “no risk no reward” seems to ring loud with many of us and while that’s true, it certainly doesn’t mean that the reward will be following. My risk tolerance began to build prior to stepping into my career when I stepped back from a Business Administration Marketing degree to enroll back in school to get my cosmetology license. My train of thought was that I had already given years of my life to college, soccer and a degree, which may no longer serve me how I once thought. I felt I was able to push the envelope and take greater risks to make up for that time. I got into the hair industry as a way of not playing it safe. Turning down corporate and office jobs, I stepped into a career where I would be steering my path and have the freedom to make what I wanted of it. I didn’t really think about the risk at the time when I started the journey, all I thought of was what I wanted to achieve or do. Read more>>

Tara Alvarez | Owner of Naturally Restorative

Have you heard the saying “don’t rock the boat”?
It is safe to say I am someone who likes to sail smoothly on “my boat”.
I am typically most at ease when I know what to expect. When I have the opportunity to organize and have day to day life run as smoothly as possible.
There have been times in my life when I had to be thrown out of the boat to initiate change or risk. With age and life experience the correlation between personal growth and risk is indisputable. Risk involves the possibility of failure, but risk can also lead you to extremely great rewards. All though I had been self employed for over 20 years, founding Naturally Restorative was truly a profound moment when I leaped with zeal into risk and change. The realization, results and excitement that I experienced made the risk of starting a company in a relatively new space an easy decision. Read more>>

Isabelle Garver | Sugar Cookie Artist

I am not a risk taker by any means. If you asked me to describe myself, “rule follower” would be at the top of my list of traits I’d use. I’ve navigated life overthinking every decision, from going back and forth on what my college major should be, to talking myself out of getting a small tattoo. Taking risks can be overwhelming and scary, and the outcome a little too unpredictable for my taste, But then in March of 2020, the pandemic hit, and the fate of the world looked a little uncertain. After spending 6 weeks with no work and nothing to do, I decided to take a risk and start my business. I launched for Mother’s Day, and the response was overwhelmingly positive. Almost a year later, I still struggle to put myself out there, and I’m not sure if I’d strip away my “rule follower” title, but I do know that that first big risk has really payed off. Read more>>

Mark Creery | Wedding & Portrait Photographer

I think without any risk, life is boring.  For me taking chances has always been a way of life, which means that so has making mistakes.  My adventurous spirit started with my travels at a young age. My parents are from England and the Czech Republic, and we would travel back often to visit family.  After high school I lived in France for one year with my twin brother, Kevin, and we traveled around Europe that summer together by train for 2 months.  We would take a train to a new location and then rush to find a hostel based on a Let’s Go Europe book recommendation and hope there was room.  Sometimes it worked out, sometimes not.  On another trip I remember taking a train through 5 countries trying to make it as far as I could using my one-day pass and ending up having to sleep outside in Stockholm because I didn’t have any local currency to pay for a hotel.  Then I got into visiting tropical locations, exploring wild jungles and caves by myself, which in hindsight seems kind of foolish.  These are the kinds of experiences that have helped form the risk-taking spirit that has fueled me to become an entrepreneur. Read more>>

Justin and Lycia Scott | Multi Business Owners

We found raising two kids and being very involved in their lives, from academics to sports and family time corporate jobs were not going to work for us. We decided to step away from jobs that were Monday through Friday, 9-5pm and start our own businesses. We cashed in our 401k that we’d been building since our teen years and invest in ourselves, and family. Read more>>

Jason Feucht | Chief Innovation Officer and Head Magister of Pit Liquor

I believe strongly in the value of freedom, and to me that means face risk and overcoming it. We never know if we are going to wake up tomorrow. If a car accident is going to take us, or a meteor. Risk is a fact of life. Whenever I think about risk I think about riding avalanches or the time I went swimming in a crocodile estuary. It was an accident, and I lived and it was beautiful. I would have missed that experience, that story and that richness of life if I didn’t take jump in and take that swim. So when starting Pit Liquor Erica and I were talking about deodorant, we had something science based, some thing that worked, and so we talked about the risk. What did we have to lose? Our meager life savings? We could rebuild it. Our Sleep? We were new parents. Our sanity? We jumped, and as always, it brings that freedom, the wind in your hair, the snow in your toes. It brings life. Read more>>

Jennifer Beck | CEO & Co-Founder of Jihi

I think risk threshold is something unique to everyone, but it’s important to be comfortable with it if you’re an entrepreneur. Being an entrepreneur is inherently risky, but I think it’s also risky to sit in a “stable” job. First of all, it’s important to remember that there aren’t any guarantees – whether you’re working for someone else or yourself, life can change in an instant. The worst case scenario for an entrepreneur is losing everything, but the end of the day, we don’t leave this earth with our material possessions. When I wake up I ask myself, “am I living with purpose today?” “am I doing my best?” “am I creating something I’m proud of?”. To me, the biggest risk is waking up and realizing I’ve wasted my precious life building someone else’s dream. In this pursuit, I might have a greater feeling of personal responsibility, financial exposure, and fears to work through on a daily basis than if I had a steady job and paycheck, but I also have more potential upside. I’m building equity value, my personal brand, and contributing my best to the world around me. Read more>>

Jimmy McMenamin | Artist/Muralist – Glossblack, LLC

I believe that taking risks is a necessary step in order to grow as a business and as a person. There are so many different areas of my career that I’ve learned specifically from taking risks. I continually find myself pursuing an area of art that I know nothing about, like graffiti, airbrushing, sign painting/lettering, sculpture, wood working, screen printing, and the list goes related to the business/client end of things. I risk failing every time I start, but I started each none the less, not really knowing if it will work out. Will it just be too difficult for me? Will it take years of work to get where I want? Maybe. But it’s never wasted time pursing a risk, even if it doesn’t turn out how you expected. I learn from these wins and losses and that’s something I can’t say if I simply didn’t try. I believe that putting yourself in uncomfortable situations will give you more perspective, more empathy, and more respect to those that are pros in the field. Read more>>

Chloë Urbanczyk | Artist and Aspiring Writer

I have so much I want to accomplish and experience in my life— so many things I want to make, places I want to see, things I want to try. Because of that, I always feel as though I’m in a race against time, to do it all (so to speak). And as I race the clock, I don’t have time to evaluate something like ‘risk’. It feels arbitrary, to me, weighing the cost of failure. The only failure I can think of is not trying at all. I start a drawing, and so much can go wrong. I have my bottles of ink stacked around me, and alas, one falls, spilling across the page. The original image I had in mind, is gone. And I’m filled with excitement for the many options this opportunity has suddenly given me. I can start again, or I can continue onward, working with this new and wonderfully unexpected puddle of ink. The puddle might at first look like a failure, but because I tried, I’ve risked nothing. And I’ve gained everything. Read more>>

Jessica L’Whor | Drag Entertainer

Risk taking is huge for my business in this industry. Not only in the content I am creating, but it is about setting the bar high and going after opportunities regardless if people say no. Risk taking has gotten be extremely far in life. I always say “the worst thing someone can do is say “no””, and you are back where you were. This goes with trusting your gut, reading a room, and knowing when it is your time to showcase yourself and your business. Read more>>

Sarah Parsons | Acrobat & Performance Artist

I see taking risks as something that’s apart of many aspects of everyday life. Whether it be mental, physical, or emotional risk – it’s often present in some shape or form. I’d say I am someone who is fairly comfortable with taking risks. I see myself as someone who leans more towards calculated risks, but then I think people see being an acrobat as inherently “risky”. In order to grow within the practice of acrobatics one must be fairly open to taking risks. Learning acrobatic skills and tricks while balancing on people high up in the air requires a lot of trust and willingness to take risks. I also think learning something new requires a level of comfort with risk taking, and requires a lot of courage. Being comfortable with trying new things has taken me far in my life. I think this type of risk taking is incredibly important in keeping life exciting and for moving through hard times. I do experience some levels of fear when addressing risks, but I try to manage them so they aren’t paralyzing or keeping me from something important. I like to think that things will turn out more often for the better than for the worst. Read more>>

Michelle Rasul | Pastry Chef

There is so much in life that involves taking risk. I have always had the same goal of owning a bakery, since I was very young. When you have a specific path that you are set on, and your every decision is based off of that dream, that path, you end up taking a lot of risk. There was a mentality of “do whatever takes to get there”. A lot of people will tell you not to put all of your eggs in one basket, but sometimes, you need to give everything you have, to an idea that there’s a chance you can achieve. That’s how it was for me when it came to Gateaux. Read more>>

John Hohnhorst | Music Artist and DJ

When it comes to pursuing a music career, I feel this is something you learn to get comfortable with. The first thing I ever did to pursue music, was take a risk. August of 2018, I moved by myself to Colorado so I could pursue music full time. Though yes, it was a very vulnerable and scary move, this also was the best thing I ever did for myself. I learned so much about myself in such a short amount of time. I always tell people, that it’s hard to become something new, when you are around people who remember who you were. I feel through great risk, comes great reward. As long as you are willing to put the work in and follow with action on the decisions you have made. This reward can come in many forms too. Not only with your career/business but also in your personal development. When you take risks, you either succeed and feel energized or you fall and learn how to pull yourself back up to try again. I see risk as opportunity. Of course, you have to be able to spot when to be risky and when not to be, but I feel the more uncomfortable we allow ourselves to get, the more we can develop our passions and ourselves. Read more>>

Jwlç Mendoza | Artist/Muralist

Risk taking plays one of the most important roles in my career as an artist and in my life. Trying to make a living doing what I love has been all about taking the risk without the fear of failing. In my mind and in my heart, I’m doing what it feels right to be doing in this life, and that’s thanks to the risks I have taken to get to where I am. From leaving my office job to asking the owner of the building where I painted my first mural to trust my vision. Even just trying a new medium on a painting can be a big risk. But learning how to use spray paint was something I wanted to learn to take my art to another level. Specially when I started doing bigger scale murals. I was afraid of messing up my paintings but I decided to risk it and not be afraid. Until now I’m still learning techniques on spray painting but it it wasn’t because I risked it and decided to learn a new medium my art wouldn’t be the same right now. Read more>>

Pamela Webb | Owner Phryne Metal Jewelry and Webb Shafer Fabrication, Making Architectural Metalwork or Jewelry For buildings!

Starting a business always involves risk. Most businesses require a fair bit of investment to get going. In my case, I needed tools, materials, and ideas for pieces I could fabricate myself and sell online and in stores and galleries. Coming up with inventory is a huge investment of time and money, and I am still always taking classes to get better at various skills. Most creative business owners use funds we make working for others to finally branch out on our own. The biggest risk is sometimes letting go of that ‘day job’. It can be difficult to believe in your business plan enough to let a good job go. Don’t be afraid to take business classes, there are many free and low cost classes and workshops offered by the SBDC or Small Business Development Center. I started my jewelry business first, as I was selling in outdoor markets and needed to learn to file and pay sales tax. Later, we added the architectural steel business to our offerings, once we slowly acquired another set of tools for working steel. Read more>>

Samson Jagoras | Real Estate Entrepreneur, Developer & Professional Investor

Risk is the currency of success. You have to take on some level of risk if you want to build a business, improve your career, make more money, have kids, get married, etc. On some level, every single thing we do in our life has a level of risk. More specifically, in business, people are often afraid to lose their income, their status, or their perceived achievements – people are afraid of losing. But the reality is, most people are playing the wrong game. Business and life are not finite, they are infinite. There are no winners and losers. Just knowledge gained and experience earned. What prevents most people from taking on risk, is not all of the external factors, but deep down inside it’s their lack of faith in their ability to solve the unknown problems and their fear of losing their perceived level of success. Because ultimately if it doesn’t work out, there is no one else to blame but yourself. Read more>>

Cynthia Rose | Alternative Healing Arts Practitioner

I prefer to think of it more as “taking leaps of faith” when speaking of things which may feel “risky” or uncertain. We can never know what the outcome of any decision we make, will be. We also each have different definitions of what we feel “risk” is. What one person feels may be “risky”, another person may feel is a natural and comfortable choice to make. We also change our point of view on “risk” over time. What I used to feel was a “risky” decision, is now a thrilling and vibrant experience for me, as I challenge myself to reach to greater heights in my own personal growth and development. I feel that in life, we will be offered many opportunities to notice where we may be operating with fear-biased programs or imprints. These programs can cause us to become self-limiting in the way we explore the world around us, and in such, we may deny ourselves the opportunity to reach our full potential. When we are offered the opportunity to observe that we feel “afraid” of something (i.e. something that feels “risky”), this is an opportunity to be courageous and to overcome these self-imposed limitations. Read more>>

Beth Ronsick | Executive Coach & Leadership Consultant

In this season of spring, the daffodils and crocus dotting front yards are perfect metaphors. It’s simply in their DNA to bloom. Year-on-year, they follow nature’s directive: To gather enough energy to push through the soil and to unfurl toward the sun. In doing so, they’re not immune to snow, dog paws, an errant soccer ball. But what is set in motion is bigger than any individual flower; they’re participating in capital “L” Life, in the whole of it, all unfolding together. Read more>>

Nicholas Emery | Artist

As an artist I live by a kind of paradoxical relativity I call structured fluidity. Although that sounds esoteric there is a simplicity to it – you can think of it like a house, I require the structure of the walls in order to inhabit the space freely. As a painter, in general, I am confined visually to the dual shapes of a square or a rectangle, whether large or small. Therefore, the image is constrained by that geometry, and yet I may be able to unearth an image and take risks with it, using the elements of color and texture as mood. I believe risk is the path of the harbinger, and that is how is how I measure success as an artist, if a piece or body of work is both personally and culturally poignant, a kind of unseen zeitgeist. Read more>>

Andriy Polietov | Videographer

Risk is something that really hits home for me actually. I see my dreams manifesting into reality because I embraced risk. I went to the full extreme and never looked back. In my early college years, I went in as a business major. I never really had many passions or interests in life, I wasn’t great at anything just about average at everything. I had a well paying sales job and was two semesters away from graduating. None of it felt right to me. I was just going through the motions. There is so much more to life then just settling for whatever falls into your lap. I decided to quite my job and not pursue my degree any further. It took some time to find my interest but photography was the firsts thing to catch my eye. That then transitioned into videography. I hope to one day start my own small production company. Read more>>

Dominique James | Founder of Real Estate Investment Firm

I’ve always been a bit of a risk taker. I think risks are a very important part of being an Entrepreneur, however I believe in taking calculated risks. The more I know about the subject matter, the greater chance I have to minimize my risks. Read more>>

Kayla Bell | Local Leasing & Business Development Manager

The road to success is never easy and majority of moving forward in your career and business is taking the necessary risks that push your comfort zone. I think 2020 had a lot to do with risk and made a lot of business owners uncomfortable, but the trick in managing risk is never letting your fear outweigh your faith, especially for something you believe in. Our business went through multiple ups and downs during 2020 and as a company and as a Leasing Manager, we decided to take the risk of putting our tenants needs first. Asa a result, we signed longer term deals with all existing tenants to stay with us at The Pueblo Mall. Risk in business takes grit and passion and I could not be more proud of the business owners in our program coming into 2021. Read more>>