Legend holds that Cornelius Vanderbilt had built a massive fortune in the steamboat shipping industry, but then realized the railroads were the way of the future and invested almost his entire net worth into railroads. The gamble paid off and made Vanderbilt one of the wealthiest entrepreneurs ever. But risks are inherently…risky. How do you think about risk and how has it affected your life and career? Some of our community favorites share their perspective below.

Liz Hutchman | Improvisation Instructor and Performer. Co-founder and managing director of Sonoran All-Valley

I am someone who is inherently reserved when it comes to risk taking, so for. a long time I ‘played things safe’ both personally and professionally by keeping risks minimal and moving forward in making choices that were comfortable, where I knew that that in a decision I was making, saying in an investment, wasn’t going to create a huge loss if things didn’t work out. Positioning myself in this way was fine, I was taking steps forward in my life, but what I started to realize is that in keeping potential loss minimal, I wasn’t making huge strides and advancing in my life the way I wanted to. I realized that in order to capitalize on opportunities, I was going to need to relinquish my need to control an outcome and be willing to let go of the fear of what could happen that could be negative, and lean into the notion that the outcome could be tremendous, positive, and create opportunities beyond my expectations. Read more>>

Lindsay Benjamin | Attorney, and Founder of Benjamin Legal & Simple Family Law (2024)

I believe other people think I am a huge risk taker, but I just never stop until I get to yes. You will always find someone who will say no, or point out a million reasons why you shouldn’t do something, but that is normally only a representation of their fears and their limits, not your own. They just don’t have your vision. I never have a Plan B. I solely focus on whatever my objective is, and take small, tactical moves to get there. So, if something does not work as expected, then it’s only a small shift or pivot to get things back on track. I am not afraid of hard work or effort, and I’ve never been someone who “works for the weekend.” I started my own law firm after practicing law for a year and a half of being an attorney and have had a flourishing practice for eighteen years now, and believe me, nearly everyone told me I should work for someone else, but I found that one person who said I should do it. Read more>>

Michael Moreno | Dad, Inventor, Entrepreneur

This is a thought-provoking and interesting question. I view risk as a subjective concept, varying for each individual. Interestingly, during my tenure in several large corporations, I found myself unable to fully commit to the businesses, resulting in a lack of genuine success. One particularly disheartening experience involved being laid off by a company shortly after taking paternity leave for my beautiful red-headed daughter. At the time, with a wife at home and five children, the situation was far from ideal. However, this setback ultimately led to unforeseen opportunities. Unable to secure a new job, I discovered the time and space needed to fully invest in entrepreneurial ventures. As the saying goes, “Bad things happen for good reasons.” Since then, I’ve embarked on the journey of starting three businesses, with Black Beard Belts holding a special place in my heart. Read more>>

Lisa Khan | Owner, Moon River Beef

I believe that most things that are worthwhile in life have associated risk. But, by doing your homework/research, you can minimize the risk so that it becomes a calculated risk that you are able to handle no matter how it turns out. Read more>>