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.

Sherry Chen | Real Estate Agent

I am drawn to risks, which is why I made the decision last year to take the plunge and become my own boss. I decided to leave my long-term career in digital marketing, and if that wasn’t risky enough, I started my own business doing something I’d never done before — real estate. Fast forward to now, I’ve closed over $10M in real estate in my first year with another $4M currently in escrow. Thinking back now, I am so grateful that I had the determination to follow my instinct and finally take the risk to do something I’d been wanting to do for years. There will never be the perfect time to make the leap, and there will always be plenty of reasons not to do it. Just follow your instinct and success will follow. Read more>>

Colette Naylor | Co-Owner of Inflate San Diego

By nature, I’m fairly risk adverse! In addition to co-owning Inflate San Diego, my fiancé Max is a full-time paramedic so I guess you could say he’s used to riskier situations. We’d always wanted to own a business together but never really knew what that would be. We would see people starting up and running awesome small businesses and think “wow, that’s awesome. We should do something similar”. But I was always afraid of starting something and not liking or it failing miserably. Read more>>

Simón Sepúlveda | Artist

I think risk is necessary, if you don´t take it you will do always the same and your work doesn´t evolve. For me when I do the same many times I start feeling a big nonsense on that activity, even if I know that people like that. I used to do tapestries but I got bored of doing the same. I have taken risk in many situations in my life: moving to different countries, changing from design to art and recently I did a performance in a self-made boat that the ocean almost take my life. Read more>>

Jillie Reil | Stand-up Comedian: THE COUGAR OF COMEDY®

I have always loved the saying “You can’t win if you don’t play.” As an artist or creative, you MUST put yourself out there. I have so many people that come to me saying “I’ve always want to try stand-up comedy” followed by a list of excuses. I always encourage those people to go NOW and hit up a mic wherever they may be. What do you have to lose? I have taken so many risks in my life, but after my divorce in rural Minnesota was a pivotal moment. I gave up every belief engrained into me as a child…organized religion, marriage, 2.5 kids, the white picket fence, climbing the corporate ladder and going to law school. Read more>>

Jacob Graham | Photographer

I feel that I have always been drawn toward risk-taking, even from a young age. The sports I was drawn to and the career paths I have followed throughout my life have always leaned toward things that were higher in risk. I was a Volunteer Firefighter and an EMT on a 911 Ambulance from age 18 to 24. From there, I went on to become a Deputy Sheriff until I was 32. I was drawn to the risk and the service to others in all of these careers. Read more>>

Amany ZAma | Handbag designer

Risk taking is a huge part of life. Almost everything we do is a risk, even something as simple as leaving your house. With a career, risk taking can be very scary because if signifies change; you could take a risk and end up homeless or take one and end up on top of the world. We should be open and accepting to taking risk because that is what life is all about. Risk taking has played a huge role in my life like any other human. Deciding to make bags with an unconventional material was a huge and is still a huge risk, but I am allowing myself to be open and accepting to taking risk, whatever the outcome may be. Read more>>