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.

Emilee Hoekstra

I personally love taking risks. I am a thrill seeker at heart. However, I have become more conservative with the type of thrills I seek these days. With business and self I believe if you don’t take risks you don’t grow and if you’re not growing you’re not learning. Being a risk taker can make you feel vulnerable and that can be a hard feeling to feel. I believe vulnerability = growth. Read More>> 

Lisa Siciliano

My entire life has been an adventure. From relocating to Colorado and pursuing photography, to embracing motherhood—every twist felt like a leap into the unknown. I don’t know if it’s my Sagittarius spirit or simply a stubborn need to forge my own path, but I’d rather embrace a gamble and fall short than sit still and stay comfortable. Read More>> 

Judith Weaver

Taking risks has always been a part of my journey. Growing up in rural America, stifled by close minded non-risk takers I bumped heads from a young age. My first life changing risk was to move from that environment to the heart of NYC. There I found culture, academia and life changing opportunities Not knowing uptown from downtown I started my career at Columbia University where I spent 13 years. I also jumped into the political world through staffing a National Advisory Committee based in Washington DC. This got me into congressional hearings and Whitehouse dinners. (Attending the dinner where Shirley Chisholm announced her candidacy for president was a highlight). During this process I also birthed a child.. Read More>> 

Misty Dockins

Risk is where growth begins. For me, taking risks isn’t necessarily being reckless—it means being brave enough to step into the unknown when I believe in something more than I fear it. Every major turning point in my life and career has come from choosing to leap: starting something new, walking away from something comfortable, or betting on a vision no one else could yet see. Risks have brought both challenges and rewards, but they’ve always led me closer to purpose, clarity, and confidence. Read More>> 

Cathy Lucas

A great teacher once told me, “trust where the universe will take you.” That advice has grounded me in ways I didn’t even realize at first. Looking back, I see that I’ve always trusted where my path was taking me, even when I didn’t have a map or a guidebook. I never thought I would spend 20 years in higher education, and I certainly didn’t imagine I’’d go on to build a successful business of my own. But here I am, almost five years into my consulting practice, proof that risk and trust often go hand in hand. Read More>>