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.

Lindsey Jones | Experience Creator & Graphic Designer

Let’s talk about risk baby let’s talk about you and me let’s talk about all the things that could be…let’s talk about risk! **in my best signing voice** On a real note though, taking risks has taught me a lot about myself, my relationship to others, what could and couldn’t be in my life/career. As an Aries sun and Capricorn moon, I oscillate between being very practical and logical to an impulsive warrior goddess. My logical side approaches risks by consulting friends/family, weighing the rewards/impacts and just sitting with it and seeing how I feel (often I’ll consult a tarot deck or 2) BUT back in 2016 warrior goddess side took over and I just jumped in headfirst, taking a risk with a friend to start a cannabis-infused event company (High Dining) that was unlike any other. Read more>>

Biggie Babylon | Entrepreneur & Recording Artist

Sometimes you have to completely start over and risk it all to get what you want. But of course, don’t mistake a risk for a gamble. You should be calculated and do your due diligence in any risk you take, especially in business. Have a goal in mind, make a plan, and execute with 110% effort. Give yourself the best opportunity to succeed but if you do fail, don’t be discouraged. Use your experience as a lesson learned and get ready to risk it all again because life is too short to not go after your dreams. Read more>>

Jason Santiago | Artist & Photographer

There’s no risk found in the dream, no failure in the imagining of success. Dreams of where you’d like to be as an artist, and the directions you’d like to take your work are nice like that. Its easy to have plans for your future take prolonged… if not permanent residence in the ethereal. It seems to us as a way of protecting them and ourselves. We (falsely) believe that if we don’t make an effort to manifest them into reality, they can’t fail, we won’t be exposed. It’s in that fear of risk that prevents us from reaching our true potential as creators. The risk that is so terrifying, is the lifeblood of our work. Without the courage to face it head on, and possibly fail… which will almost certainly at times happen, we cannot expect to fulfill those dreams. Personally, I have taken many risks in my life, and have failed many times. Read more>>

Rebecca Friedlander | Film Producer, Author & Creative Artist

Theodore Roosevelt said, “No man is worth his salt who is not ready at all times to risk his well-being, to risk his body, to risk his life, in a great cause.” I believe each of us caries a dream in his heart, but it often takes great courage to risk the adventurer required to put that dream into action. First, there’s the personal risk of being willing to put pen to paper and draft the muttering ideas in our head into a logical blueprint. Whether it’s a film, book, song, or a crazy idea to renovate a family cabin in the forest, my ideas all start with a concept that rolls around in my brain for a while and eventually makes its way onto a crisp, white piece of paper. Just putting the thoughts on a page is the first risk. Not every idea is a great one. Being willing to sit down with a notebook and write my ideas out requires me to risk the creative process. It’s something that every dreamer has to wrestle with: the courage to take the first step. Read more>>

Alexia Bregman | Entrepreneur

I love the concept of risk. In my Vuka coaching business I’d say that perceived risk and fear are two of the greatest barriers to people moving forward in their businesses and lives. And I am highly aware of the fact that I don’t see risk in the same way as others. I’ve always been a risk taker – I moved from my native South Africa to a completely unknown country and society (shoutout to my Denver peeps!). I started a business in 2008 at the bottom of a recession in an industry littered with brands that hadn’t made it. I’m currently running three new businesses and am in school trying to finish the degree I took a risk and left in the 90’s. I’m learning to surf, which at 47 is risky! Read more>>

Vicki Murphy | Quantum Energy Coach & Intuitive Healer

My first ginormous risk was following my heart and pursuing art as a career, despite hearing over and over again that I would be poor, starving, and unable to support myself. My next big risk was not as scary, because the first one brought so much success, and an understanding about how the universe “answers” you if you are “willing to take a risk” that is based on your hearts wants and needs – those that are healthy for you and feed your soul. My second big risk, following my successful art career, was in stepping out of the proverbial “psychic closet” and allowing others to “see me” and my abilities. Again, as this ended up serving me and creating success, and because of this, all subsequent risks were less scary. As a matter of fact, I now embrace risks, and the fears that define them as risky, with enthusiasm. Read more>>

Trisha Williams | Founder & Product Director

Pigeon Hole Production’s story has been defined by risk. When we (Joseph Unger and Trisha Williams) founded PHP, it wasn’t just creating a new business, it was the beginning of a new life. As partners, we’d been working together in the game industry for years and decided to start anew in San Diego. We had no connections here, just the grit to make our story happen on our own terms and a goal to become part of a community. Working with new technologies is always risky, and we wanted to ensure that we didn’t completely rely on just the fun, cutting edge tools, but also strongly on Research & Development, and World Building. Introducing those elements to each other in combined projects wasn’t always easy, but with patience and determination, we began to integrate technology such as virtual and augmented reality into communities in order to create a shared, aspirational world that could be experienced together. Read more>>

Hedras Ramos Sr. | Music Producer & Musician

I’ve taken many risks in my life, but probably the biggest one was to leave the established security of owning a nice house back in my home country to come to California to start a new life from scratch in one of the most expensive cities of the US like Los Angeles. But when you have a dream, faith, and hope for a better future is all worth it. Read more>>

Claire Petretti Marti | Author & Yoga Instructor

I’ve always loved taking risks and avoiding following a traditional path. I’ve lost several people close to me, including three of my brothers, who passed away much too soon. From a young age, I knew on some level that my choices were shaping my life and that I didn’t have time to waste. I’ve chosen and continue to choose to follow my passions. When I became a lawyer, I knew it was the wrong path for me. Over the years, I quit practicing law, and tried on a variety of hats, including running a non-profit animal rescue for a Hollywood actress, selling legal software, teaching Pilates and yoga, and of course, writing books. I have many interests and never thought twice about leaving an established career when I felt the calling to do something new. Read more>>

Clint Brandon Cave | Digital Media Creator

I am a calculated risk taker, I am a firm believer in “no risk, no reward”. All of the best experiences that I have gone through in my life all stem from risk. I like to think of it as shaking the dice. Once you muster up the strength to actually do something that you’re nervous about, the chain of events that take place after are amazing. My career started with me shaking the dice to leave a job to go and travel, which led to me picking up a camera, which led to me creating beautiful content, which brought me to California, and so much more. I just firmly believe that in order to get a reward, risk needs to be involved. Read more>>

Marlon Saunders | Singer, Songwriter & Teaching Artist

I feel that risk taking is a key to a successful business that you envision or dream of. Those of us who decide to follow our passions are deciding to not follow a safe, practical route. This immediately puts the mind in a space to think outside of the box. My entire career has been about taking risks, deciding to move to NYC with no job and knowing that I was going to break into the music industry and I did. My creating my new business venture with ENSE Music and taking a risk of creating my single, ‘Dark Day’ at a time in our country where taking a risk and speaking up for what you feel is right can cause tension with people in your life. For me there is so many amazing opportunities in life and to allow space for them requires taking a risk. Read more>>

Caryn Blanton | Community Advocate

Not long ago I read an article that talked about how parents should encourage their children to take big risks. The author gave the example of his college aged daughter going away by herself to Korea to work for an international organization. She was in a totally different culture, didn’t know anyone there, didn’t speak the language, found herself alone is some pretty sketchy situations…and she loved it! She grew in maturity and in confidence. The author felt that the bar for risk was set high and she would be better equipped to handle what life would bring. For him, this is the way that we can instill the knowledge that they can do hard things. Agreed. I feel that from a young age, I’ve been fearless. I’ve done a lot of hard things in my life, starting at a young age, and because of that, I know that things have a way of working out – and usually, for the best. Read more>>

Rick Crandall

My whole business career has been about taking a risk – starting a tech company, breaking new ground, helping over a dozen other venture CEO’s get past their challenges – and helping companies navigate the risk of a strategic transformation. In few words, I say: 1: pick and attract the best possible team, do not settle for “OK”, 2: infect them with your enthusiasm for the mission; 3) proceed into the unknown with a strategy and focus as though you know for sure it’s going to work – your team wants to believe you have all the answers even when you don’t., and 4) believe in your heart that there is a way to succeed and get past the risks. The secret here is if you see an element of the plan or a team member not working – change them early and then proceed with the same belief and confidence and passion. Read more>>