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.

Whitney Kenter | Glowe Connective Founder & CEO

I have always thought of myself as risk averse, yet when I was asked this question several months ago I spent some time reflecting on my life and to my surprise my actions indicate otherwise. Now, I say that I am an intentional risk taker. I made a list of some of the major life risks I’ve taken and I could summarize the impact of each risk as significant growth. They all weren’t ‘successful’ in a traditional sense, but massive learnings that have led to future risk taking and I would say created the opportunity for quantum leaps. Read more>>

Brendan Flanigan | Residential Roofing and Remodeling Conractor

The entrepreneurial world is filled with inspiring and successful people espousing the merits of a “risk it all” mentality. While this makes for good motivational content, I believe there is something to be said about a more calculated approach to risk taking that doesn’t put you and your family in needless financial disarray. Can you venture off on your own and build a brand from the ground up without any risk at all? Of course not. Read more>>

Ryan Domson | Online Boutique Owner, Secretary + Mama

Taking risks is scary, but often well worth it, and if not, at least you can say you tried & not always wonder, “what if?” Starting this online boutique was definitely a risk, but it has also been a huge dream of mine for as long as I can remember. I always found an excuse/something to hold me back, but I had a huge wakeup call in 2018 that helped me realize life is too short to live out anything other than your dreams 🌙✨ Read more>>

Cameron Rhodes | Fly fishing guide and instructor

In my industry risk taking is huge. Everyday you might take a risk on where to fish or how to fish. I think taking a risk is always worth the reward in this case. Most times I will always take the risk as long as I am not putting clients in danger. Sometimes it doesn’t pan out and all that was lost was the effort. But the reward of gaining that knowledge or catching a fish of a lifetime was definitely worth the risk. I took a huge risk when I started my own fly fishing guide business. I took the risk of burning bridges with people I have worked with in the past. Read more>>

Catalina Escallon R. | Entrepreneur & Artist

If it wasn’t for risk, I wouldn’t be where I am today. Of course, it came hand in hand with the pandemic and so many other factors that I had no way of controlling. By March 2020, I was unemployed and didn’t see many other possibilities than to start something of my own. That is how Noodo Studio was born. Later my business partner Daniela Guarin, joined me in this venture and I knew she will risk as much as I was. For things to work, you need to go all in, which involves a high level of risk. We are both so invested in growing our business that we will risk a lot, hoping, of course, it would pay off. No risk, no gain. Read more>>

Tawni Ledford | Broker Associate and Small Business Event Coordinator

Taking risks has been an integral part of my life and career. We don’t always have the luxury of knowing what lies ahead or have the grace of time by our side. When crossroads present themselves, often times, a decision must be made in a fleeting moment. Some may perceive this as a scary idea, but I find it enthralling! The best moments in my world have been made up by a trail of exciting decisions, and a “jump with both feet in” mentality. Read more>>

Trish Cox | Realtor

Taking risks is SO important!! My risk appetite is quite large, if I could say so myself 🙂 I’m originally from 30 min north or NYC so I grew up fast, thinking I knew everything about life. I left the nest and went far away to college in Indiana (go hoosiers) where I realized the rest of the country is not like NY. I had your typical wild college experience, learned a lot about myself, but came back to NYC because that’s just what everyone from where I am from, does! Read more>>

Paulina M. Johnson | Paper Artist

There is a saying that goes something like ‘what you want is just on the other side of fear’. It’s so true! I believe fear can be paralyzing but on the flip side it can also be a powerful catalyst to action. Maybe fear resides within the things we care about most and that is why when we take the risk to push beyond, we are able to find our own personal treasures. Read more>>

Kirra Hellfritsch | Metalsmith & Interdisciplinary Artist

Risks open doors. And sometimes they close doors, but perhaps that wasn’t your door. Move on and don’t be afraid to try another risk. In the art world, almost every move is a risk because we create our own structure in which to move forward. I’ve always loved making and I’ve always loved art. I almost moved out of art to pursue a more academic path, seeing my friends around me put down their creative endeavors in an effort to get more serious and plan for the future. Read more>>

Daniel Wagner | President & Thrill Seeker

I’m a true believer that the “greater the risk, the greater the reward”. Without risk taking, we would never get ahead in life. Whether it’s buying a new house, starting a new job, or falling in love, it is all a risk. We all must be willing to risk something in order to get the things we truly want. Because of this, I enjoy the thrill of taking a chance. The thrill of the unknown. The “what if’s” and the “lets find outs”. Read more>>

Britanny Gutierrez | Esthetician and Makeup Artist

When I think about risk I think of the unknown. I’ve always been a person whom likes to know what is next as far as what I’m going to do with school, work and let’s just say have for dinner a day ahead. Risk has definitely played a huge role for me. Just to give a small background of myself, I come from a Latina background. My ethnicity is: Guatemalan, Mexican and Salvadorian. Both my mom and dad were always telling me I needed to go to college and get a degree. It was embedded in me that I had to do this. Read more>>

Brandon Rutherford | Model and Recording Artist

I love risk taking, it has made me exactly for who I am today. I have taken risks that nobody will rarely take. I wanted to get results that no one else was. It has played a big role due to the fact of the people that I have met, the connections I have built, the places that I’ve been, and the doors that I have opened. Risking everything for my life and everything that I have obtained came exactly from me taking a risk. Read more>>

Shaylen Broughton | Abstract Artist & Muralist

Risk-taking is a major part of being an artist. We have to be willing to take big risks both in our work and creative process and with our business. It was a huge risk for me to leave my corporate job as an interior designer to follow my passion and pursue art, I moved on faith, I knew it would be difficult and that I wasn’t going to get rich but it’s what made me happy. Read more>>

Ben Crocker Laura Farley | Pizza Business Owners

When it came to opening up the pizza shop, opportunities, timing, and disciplined were the key factors towards a plunge into an entrepreneurial career. Ben was coming from a firefighting career that was more than willing to take him back should things have gone south. He decided to stay on as a volunteer for several months while doing initial setup of the Pizza shop before switching completely. Read more>>

Veronika Sprinkel | Creative Writer

Oof… Risk… What is risk, really? Life is a risk. The world is crazy. Anything can happen any time. And I think the common practice is to view risk as some sort of an equation: If I do X, it will result in Y. If I do A, that’ll get me B. Read more>>

Gabby Maldonado | Lash Artist

Risk can be scary, change is always intimidating but if you don’t take the chance there is always that “ What if” thought that goes through your head. I started my business risking everything, risking my financial status, risking it failing, I risked it all. I have always been a risk taker because I believe it you don’t take the chance you will regret it. Read more>>

Tayo Okunade | Attorney

There is something exciting yet scary about taking risks and venturing out into an unfamiliar territory. Yet, from an early age my parents instilled in me the values that are embodied in the adage, “nothing ventured, nothing gained.” Born and raised in Nigeria, my mother, siblings, and I immigrated to the United States following my father who immigrated previously and was working on sabbatical at the University of Mississippi. Read more>>