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.

Alex Winter

I love discovering new things in my life. The unknown always carries a certain degree of risk, and for me, that’s completely natural. Risk is also about making choices. Of course, I assess potential threats as much as possible and avoid acting recklessly — that wouldn’t be risk, that would be foolishness. But it’s simply impossible to predict everything in advance. Read More>>

Silvana Vengoechea

Risk taking has been a huge part of my career from day one. My mom, a retired colorist always taught me that being afraid was going to be the only thing holding me back from growing. I see risk as an essential part of growth. Every major milestone in my career, from opening my first salon to stepping on stage as an educator, came from saying yes to opportunities that felt both exciting and uncertain. Read More>> 

Jessica Portillo

For me, risk has been the foundation of every major leap in my career and life. I bet on myself in the early 2000s when I left a lucrative career in San Francisco to move back to Los Angeles for beauty school—working full-time while studying full-time. Fresh out of school, I took another big gamble by heading straight to Beverly Hills with my brand-new résumé, determined to work in high-end beauty. That risk paid off, leading to over a decade of working in 90210 alongside some of the best in the industry. Read More>> 

Daniel Herrera

I’ve always believed that on the other side of fear lies something amazing. Everything truly worth having in life comes with some level of risk. I’d rather take a chance and have it not work out than live with the regret of never knowing what could have been. Growing up, my dad would always say, “What’s the worst someone can say? No? Who cares, go for it!” That stuck with me, and over the years I’ve seen firsthand that risks are often worth the reward. From making a bold career change 15 years ago, leaving teaching to join law enforcement, to writing and publishing a children’s book and experiencing the incredible opportunities that followed, none of it would have happened if I hadn’t faced my fears and stepped into the unknown. Read More>>

Valerie Pinon

In a government municipality and hospitality setting, risk-taking often involves balancing innovation with public responsibility. Personally, I view risk as an essential part of growth and development. In my career, taking calculated risks has allowed me to explore new ideas and improve services, whether through implementing new programs, enhancing guest experiences, or optimizing operations. Read More>> 

L Fried

Risk played a pretty big role in my life following college. After I graduated, I decided to move to Seattle—a city in a region where I had little to no connection. For most people from Florida, NYC is a natural move upon graduating, and I was actually born there. Though I had a decent sized support system in New York, I really wanted the challenge to immerse myself in an environment that was pretty unknown for me. So that brought me out there, where shortly after arriving, I landed a graphic design internship at the Seattle Art Museum. Read More>>