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.

marysarah ivers | shop owner | The Olive Branch

I have come to love risk, or rather, see that it is essential to my happiness. In starting a shop during this time there was an obvious risk. In starting any business, regardless of a pandemic, there is a risk. But it seemed to me that there were two choices in front of me – either I respond to my fears + the real possibility of failure, or I say yes to the risk + follow my heart. Not to be cliche, that was a real sentiment. When I think about different moments of my life, I can clearly see that the most beautiful things that have happened to me have required taking a risk. I think of my closest friend, whose love for me I would not know without having risked pursuing that friendship, + vulnerability. I think of choosing the study philosophy, accepting the risk that it denied me some clear path to a career. Read more>>

Robin Medina | Owner & Stylist

I believe that most everything you do in life revolves around taking risks — your career, the person you choose to marry, the way you decide to ultimately live your life it is all a calculated risk. However, you do your best to set yourself up with the best possible outcome (or odds). I was so young when I started Felicé Bridal, 22 that I am not sure that I even understood that a business could genuinely fail. I thought that you have a great idea, which at the time meant bringing new and exciting couture designers to Ft. Collins, CO and starting a brand new beautiful bridal boutique. Looking back almost 20 years later, it’s funny to think that I had no fear of failure, success seemed like the only option. Today, I realize how badly that could have gone, and how fortunate I am to still be able to be doing the one thing that I love most – styling brides and sharing such a wonderful experience with them. Read more>>

Ashley Smith | Marketing Director & Family Photographer

I tend to think of myself as type-A risk-averse person. I like control – or at least the feeling of control. And yet, I can clearly look at my life and my career and see that my biggest risks have lead to my biggest rewards. For instance, almost 10 years ago, my husband and I decided to make the somewhat unlikely move from LA to Denver. We both had dream jobs in entertainment and amazing groups of friends. We enjoyed all the perks of good weather, nice restaurants, endless entertainment and nearby family. Read more>>

Corrie Sharp & Jennifer Tom | Co-owners of Bubby Goober’s Baked Goods

Starting your own business is about taking a number of risks that expose you to others’ opinions. It creates a feeling of vulnerability that can be very uncomfortable because you’re sharing something you care deeply about with the community and there is always a level of uncertainty about how people will respond. We like to think about taking risks as the opportunity to be brave. It’s an act of hope. If it pays off, the rewards far outweigh the fear. If it doesn’t pay off, you have the opportunity to try something else and start a new adventure. Read more>>

Gabrielle Herry | Freelance Photographer

I always think of risks in my life with a simple question: will I look back in even just 5 years from now and regret it if I don’t take the chance? Often times, this leads me to dive into opportunities set before me; no matter how much they scare me! If I didn’t take risks, I would have never gone to college, never travelled alone and seen almost 15 countries by the time I was 21, I would have never met my husband, and I would have never started working for myself doing something I have always loved to do, naturally! Read more>>

Janie Halaba | Realtor and lover of aviation

Taking risks is a part of who I am. You will never know if something is possible unless you try it. If you end up failing, it is a learning lesson for the next time. I don’t intend to have any regrets in life, only experiences and memories. This has played a huge role in my life and career. If I think it is possible, I am going to try it. Becoming a Real Estate agent is no exception. As long as you are passionate about what you do, you can accomplish anything you set your mind to. My goal is to help as many people as possible find the home of their dreams, invest, relocate, etc. Read more>>

Brittany Vidi | Yoga, Meditation & Sound Healing Practitioner

Taking risks, for me, has always come down to my heart vs my head. Over the years, I have been consciously developing a strong ability to listen deeply to my heart when it swells up with excitement and something feels in alignment (especially when it doesn’t make much sense yet). This is often distinctly different from what my head is saying, which craves security, stability and will tend to generate a lot of fear around the unknown! Taking risks for me has meant following my heart, learning how to recognize what lights me up inside and then taking action to move in that direction which has guided me too many of the exciting adventures and business opportunities I have taken over the years. Read more>>

Izzy Roig | Photographer and Painter

I think risk taking was something I thought really consciously about when I was in high school/early in college when I was more insecure in my art making process. I would see creative practice in this binary where there was “safe art” and “unsafe art” that didn’t guarantee a good audience reception, but still was fulfilling to make. Since then my idea of risk has changed in that I have become really desensitized to this binary; I think there is just craft. I don’t really care as much about whether or not people will “like” my art. Of course I hope to evoke some kind of response in someone who views my photography or paintings, but whether or not that response is positive or negative doesn’t have any influence over what I make. Read more>>

Marcy Miller | Sandwich Shop Owner

Starting your own business is no doubt risky. Becoming a first time entrepreneur – downright scary. Before I opened my sandwich shops, I would buy a coffee for anyone and everyone willing to sit down and talk with me about starting a business. The first part of the conversation was always “do you know how risky this is and how many restaurants fail?” Of course I did. My answer was always the same: I would rather pursue my dream and fail then to look back on my life wishing I had the guts to give it a try. Read more>>