In our experience, most folks, including ourselves don’t have enough of an understanding of risk and the role it plays in our lives and careers and so we have made a concerted effort as a team to have conversations about risk with our interviewees. We’ve shared some highlights below.

Jonathan Cook | Owner/Founder of The Jonathan Cook Team at Keller Williams Realty

With great risk comes great reward. I have lives by this my entire adult life. When we approach a decision on The Jonathan Cook Team we ask ourselves how can we take the maximum advantage over competitors through calculated risk. I have watched so many amazing no brainer home run decisions be turned to the tune of 10s if not 100s of thousands of dollars just because the person says I’m not a real risk taker. Read more>>

Art Fairchild | Sculptor

Taking risks always pushes boundaries. In my life, the level of risk I have been willing to take has been on a sliding scale. As a young person, I was fearless and stepped out in blind faith that my pursuits would be met with success.  As I grew older, I met risk with a more calculated approach. When I decided to completely change my path to a career as an artist, I took the knowledge and skills acquired throughout my life, paired it with renewed zeal and moved forward without trepidation. When I was a young man and introduced to the trade show exhibit business, the intrigue and fascination initially made me hungry to learn carpentry skills needed to fabricate these types of structures. After having worked in the industry for a good number of years, I accumulated the knowledge and skills to weigh the risk of continuing to work for other groups or beginning my own entrepreneurial path with unlimited possibilities. Read more>>

Jason Keung | Designer & Founder of Harepin Creative

Risk is almost required in any industry let alone being an entrepreneur. Even though I’ve tried to play it safe by doing as much planning and research as possible to mitigate risk. I’ve had my share of failures, however I have learned a great deal from each one. After my career industry was hit by a recession in 2008, entrepreneurship became the end goal. Depending on someone else for working didn’t sit well with me anymore. I ended up jumping into a different industry for better opportunity and growth. Over the next few years I had developed and attempted multiple business models with some success. I will say that if it wasn’t for the support of my close friends, family, and mentors, I probably wouldn’t be where I am today. Read more>>

Mary Clay Gupton | Small Business Branding and Web Designer & Freelance Writer

If someone asked me point-blank if I was a risk-taker, I’m not sure I’d answer with an emphatic “yes!”, but as I reflect on my career… there’s really no other answer. A self-proclaimed late bloomer, I had no idea what I wanted to be when I grew up, and I took a job out of college in the Oil and Gas Industry in Fort Worth largely because I loved Fort Worth. After growing up in Amarillo and attending The University of Texas in Austin, I found it to be the perfect combination of the two cities, both geographically and culturally. In my time in Oil and Gas, I always knew it was not the lifelong career for me. After 7.5 years in the industry doing everything under the Landman umbrella from leasing to title work to lease analyst and currative title, I knew the time to leap was nigh, and my first itch to take a career risk started to fester. A writer at heart, but vividly aware I had no background or experience, I started to look for a role to allow me to write as a novice. I was newly married, and my ever-supportive husband encouraged me to take the leap out of OGL and into something more creative. Read more>>

Roxie Reese | Cosmetology School Owner & Educator

Roxie Reese is both a passionate educator + entrepreneur striving to bring opportunities to her community. She is the founder of DFW Lash University in Carrollton Texas and a Dallas native. At only 20, Roxie started her journey in the fashion industry, her expertise in both visual merchandising + manufacturing. Her passion for business grew throughout her time in the fashion industry. In 2015 her life took an unexpected turn, she ended up involved in a crime. This changed her life’s trajectory… She knew her life was at a crossroads. She enrolled in the eyelash extension specialty program to become a licensed lash tech. Roxie went forward to gain her Master Educator License and opened DFW Lash University after building her independent lash business, Roxie Lashes. She was able to hit the ground running with her business in 2020 despite the obstacles caused by the pandemic. Roxie Reese stands by her mission: Passion is easy, execution is hard, improving the beauty industry by empowering the lash artist and master educators of the future. Read more>>