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.

Kaitlin Meyers | Photographer

Our business has really been influenced by taking risks, starting when my husband quit his job to learn videography and joined my photography business. We then renovated a school bus and traveled across the country, which was an exciting yet unpredictable move. Taking those risks taught us a lot and it thrust us into not only creating a really diverse travel portfolio but also learning a lot about running a successful business. We learned that sometimes taking a risk is necessary as a business and you’ll always be wondering ‘what if?’ if you don’t follow your dreams. Try new things, and when they aren’t successful, accept it and pivot your plans according to what you’ve learned. Read more>>

Christine Lacayo | Multilingual Content Writer

I guess you could say I’m a faith-filled risk taker. I grew up with parents who took a big risk in immigrating from Latin America to the US not knowing if “the American dream” would work out for them but following their faith to where they were called. My dad became a very well-respected doctor in Atlanta and my mom made sure to raise us with strong values and deep-rooted faith. Read more>>

Flo Sherry | Realtor & Story Teller

I have always welcomed risk in my life – in terms of trying new things. I’m not a dare devil and you won’t see me bungee jumping off a skyscraper anytime soon but risk makes you feel alive. It’s exciting and scary not knowing what the outcome will be. It’s fun dreaming about possibilities and all the wonderful things that might happen. But even worse is looking back later in life with regret. wishing you took that chance. I met my husband when he was on a business trip in Toronto, and I had just graduated from college. Read more>>

Mad Dog Friedman | Musician, poet & digital artist

Starting my own band after 50 years of playing in bands, in which I was limited in my ability to explore new sounds and ideas in my song writing and performance, was a considerable risk. To pursue my dream of starting an contemporary acoustic harmonica blues band, I had to let go of a successful band I played with about 10 years. This new unique sound blending mandolin, acoustic guitars, stand up bass and harmonica and melding the styles of traditional country blues with the “Colorado Sound” (jam grass) was not something I had heard before, Read more>>

Kevin Conn | Owner/Operator, Rapid Image Photography LLC

Risk taking has always had a special place in my heart. My mom would love that I chose this question, as I grew up with her constantly reminding me that I had a tendency to “throw caution to the wind”. I’ve since learned how to better evaluate risk, and subsequently make more calculated decisions regarding those potential risks, but the excitement of the unknown is still probably my largest driving factor and motivator in both my personal and professional lives. Having always been an adrenaline junky, risk taking has been a constant for me. Read more>> 

Coastless Creatives | Concert collective, Talent buying agency

We think about risk as a bi product of progress. Any time you decide to move to a new place in your career or your life you face challenges. Even when you move to a new home, that change involves the risk of your stuff breaking, the movers costing you too much etc. But when you move houses you aren’t focused on the risk taking, you’re focused on finding a better home. This is how we approach risk taking. We want to move this company forward to places it hasn’t been and to better places that will help the music community the best that it can. Read more>>

Keller Paulson | Comedian, Musician, Actor, and Podcast Host

I have always been an adrenaline junky. I used to snowboard and skateboard, I’ve gone skydiving; I’m always pushing my limits and testing what scares me. This directly transfers into how I live my life. Not in a lawless, chaotic way. But, in a way that keeps me alive. If something scares me or seems risky, I’ll ask myself where that’s coming from or why I feel that way. If it’s something that’s intended to keep me safe and out of harm’s way, I can understand that. However, if what I’m feeling is based in fear of the unknown or fear of change, I know that it’s something worth checking out and pursuing. In order for me to grow and learn more about myself and gain experience, I need to continue to take risks. Read more>>

Katie O’Hara | Writer

Risk-taking has played a really major role in my life, but I honestly wasn’t consciously aware of it until I was asked this question. I have always taken risks in pursuit of marching to the beat of my own weird little drum, following my heart, and listening to my intuition. I often jump with both feet – without looking first – into everything that I do, and this is most evident in my academic and professional careers. I applied to ONE college – because that was where I was going; there was no second option. Read more>>

Stacy Read | Commercial Developer and Small Business Believer

I believe that risk = reward. While there can be varying degrees of risk, and other factors that contribute to the level of reward, I do believe that taking risks is why I am where I am today. Creating businesses, and developing concepts that are new or different can be welcomed or can fall flat in the eye of the public. My decision making with risk taking has evolved over time, but I have definitely been on the high end of the risk scale for most of my adult business building life. If I have a passion for my work or the project, I will work to a high degree to develop and set up the new business for success the best that I can. Read more>>

Josh Allison | Photographer

Risk is a great question. I have a little bit different perspective then most, and it has played a huge role in my life. I started rock and ice climbing at a very young age and eventually pursued it to almost a professional level. With ice climbing, the risk is very high, especially at an elite level. The consequences can absolutely mean death, and same in the fire service. That has played a large role in my business where risk is financial, so I was kind of all in. I really don’t get too afraid ever. I feel like risk is more just discomfort that I need to overcome and succeed at all cost. Read more>>

Elicia Hodge | Content creator and realtor

Risk-taking, to me, is facing your fears head-on and trusting that it will work out in the end. An excellent example of this for me personally was when I separated from the Air Force to rediscover myself and pursue my passions which resulted in me going to college full time and starting my business. However, when I separated from the military, I settled in Colorado, where I had no family or friends- I didn’t know anyone, and I was pretty much on my own. But I trusted that I would be okay through this journey. Read more>>

PartyKing Jeff | Music producer / Event coordinator

The saying is “nothing ventured nothing gained” and I’m a firm believer in that statement. In other words I believe that risks are a part of the grind to become great . Trying new things out and being the first person to do it has taught me how to face adversity and to understand that not everyone will see your idea through, because they’re not supposed to and that’s what makes you different . Ultimately being different has gotten me to places that otherwise I wouldn’t have been . Read more>>

Gary Ruiz | Lifestyle/ Conceptual/ Fine Art Photographer

I think risks have played a big part of my business success. Taking risks have taken me to where I am now. One clear example was when I decided to move to the United States. Sometimes, I think about what would have happened with me if I would had decided to stay in Mexico. I know that if I wouldn’t have taken the risk of leaving Mexico (which was super scary because it was a big decision), Read more>>

JD Fridlund | artist, musician

My whole life has been about taking risks. Not for the sake of taking risks, but out of a conviction and a passion for my work. I dropped out of school after ninth grade, was accepted into a one year art school program and after that went on to another, two year art school, and then one more two year school.
This was all in Sweden, where I am from. Read more>>

Elsa Verrier | 51:10 Youth Ranch Director

My husband and I spent 20+ years in corporate America. He was corporate finance and accounting, and I was in Human Resources. We both have multiple degrees, but it’s through the adoption of our three children that we decided to take some risks. Or, as we say, we stepped out in faith. Our son was adopted from Nepal and came home at 18 months of age. Our twin daughters came from Bulgaria, and they came home just before their fourth birthday. It’s with the adoption of our daughters that our family pursued counseling to help our family adjust to our new way of life. Read more>>

Eugene Ebner | Media Personality/Vocalist/Producer

Risk is a part of life. In my opinion, taking risks allows us an opportunity to grow personally and professionally. As a creative entrepreneur, I have had to take many risks over the years. Some risks have paid off; while others have been valuable and important, yet sometimes challenging, especially in the last few years. I think what I had to learn over the years was that risk-taking is not only a choice but that, even when something is considered a failure, it’s really not. Because you evolve and learn what to do better next time. You never know when that one risk will pay off. That’s where the true magic lies! Read more>>