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.

Kenny Vasko | Co-Owner

I used to think about risk all the time. When I was in Corporate America, I subconsciously always had some sort of exit strategy in the back of my mind; some mythical life plan. The modern American dream of dumping money in a 401k for thirty years and then look like one of those smiling people in the AARP commercials. I might have taken some small risks here and there, but when I look back, they were in some tight guardrails…as long as I made x amount of money each year, for instance, I would be fine. Read more>>

Kim Hefner | Colorado Elopement Photographer

After spending a decade working in accounting and finance, I left my corporate job to pursue building a creative business as an elopement photographer. I can say with certainty that most people in my life considered this a risky move. And I actually agree. Staying at my 9-5 would have offered more financial certainty, at least in the short term, since building a business takes time and there are no guarantees of success. Read more>>

Brie Oglesby | Mrs Planner

When 2008 and 2009 happened, many people’s careers shifted. Owner of Mrs Planner, Ashlee Voda, left her corporate planning role and was certified as a wedding planner picking up any mentorship opportunities she could find. There were definitely financial challenges and lifestyle changes that made it clear her personal life was going to be sacrificed by her professional as she got started. We have never been afraid to take risks and that’s important when pursuing your own passion. This follows through into every couple we meet and the dynamic of their event that we take on. Read more>>

Andy Sovick | Entrepreneur, Publisher, Craftsman

Measured risk taking is the keystone to my personal and business life. As a passionate backcountry skier, climber, boater, and hunter, I find myself constantly calculating risk. In my entrepreneurial life, I’ve found that I perform better, and move through my day with more passion when the stakes are high. The way I see it: Likelihood X Consequence = Risk. Read more>>