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.

Jade Santana | Brazilian Actress

If I hadn’t taken a risk I wouldn’t be where I am today. I was studying for four years to get a major in Architecture and I had a job in one of the best Landscaping offices back home. Two more years and I’d be ready to go, making money, getting ready for the next steps in life and all that. But I knew I wasn’t happy, I had pictured me being a totally different person by the time I had gotten to that stage in life. I realized that I had only done what I was told to do instead of what I’ve actually always wanted to do. In a spur of the moment decision, I bought a ticket to LA and enrolled in an Acting Summer Course just to see what would come out of it. I decided to really take those two weeks to make up my mind about my future. Yes, Acting is great and all that but do I actually have a shot in it? Am I good? Is it possible to make a career out of it? And do I love it enough to risk it all in order to follow what I believe is what I was born to do? Read more>>

Dana Randazzo | Owner & CEO

By its very definition, risk implies that something is in jeopardy. I am a risk taker by nature, I fear little and always tend to side with the underdogs. I believe in equality across the board. I will take chances on an actor or model that has the desire, drive and love for the art. If they are not naturally inclined but have potential, I’ll give them everything I have to help them see that come to fruition. It takes time and there is risk in that. I could work with a client for years and the work may come slowly. Many land roles right out the gate, but sometimes it’s a matter of growth. But, my reward is seeing them come out of the process a more confident, ambitious artist. There’s no failure in that outcome. Read more>>

Joanna Paola Honeyman | Design Strategist

I come from an immigrant family, which by itself means risk played a huge role in my life. My father often tells me about the giant risk he took coming to America with only $120 in his pocket and a dream for a better life and better opportunities for his family. Both of my parents faced a lot of adversity adjusting to a new life with a young family and maybe it was that influence that made me believe that anything was possible – but only if you are willing to take risks. As far as my career goes, I have never taken the safe route, though at times I have stayed at places longer than I should have. Leaving a comfortable corporate job to start my own agency was a huge risk. It was a great job, in a world renowned company with insurance and benefits. I could have climbed up the ladder and lived a comfortable life. Instead I decided to bet on my freedom. I wanted to have the freedom to chose who I wanted to work with and the kinds of projects I could take. Read more>>

Katie Bright | Visual Artist & Creative Director

My life on the edge, a cat with nine risks, I stayed focused on a creative dream, I said yes to everything, I literally jumped ship and ran amuck, move country for work, move country for love, lived life passionately, then eventually all nine risks paid off to a sense of happiness. I’ve established with you I’m a risk-taker, so let’s begin the journey of each of those nine, title with a theme song. Risk 1 – “Don’t Stop Me Now” Queen I left school at 15 and went to art school for 3 years. Halfway through my course, the teachers unanimously, bar one, the incredible Marie Kolesnik, took it upon themselves to tell me I didn’t have the talent to go to one of Europe’s best fashion schools. With only Ms. Kolesnik’s support, I took on the school, and not only did I get my first University choice I was accepted into every Fashion School I applied to Win-Win. Risk 2 – “Live or Let Die” Paul McCartney and Wings I arrived in London and I was definitely a small fish in a big BIG pond, my 39 classmates and I were told no freshers week for you. Read more>>

Pernille Kjeldsen | PR & Partnership Director

Risk has played a huge role in most of my life and career. I’m the kind of person that acts upon my feelings and desires more than being rational and logical, which is not always a good thing. But it has brought me to where I am today, which I’m grateful for. To me risk taking is a necessary part of my life. I have so many dreams and goals I want to achieve, so risk taking is just an inevitable part of it. Even though I know by taking a risk that it can end up failing, I also know that it will teach me a lesson and keep me from doing the same thing again. Sometimes it means learning the hard way but the personal growth I experience ends up being worth it. I’d rather live my life like this, a bit like a rollercoaster, than being stuck in the same place both physically and mentally. The biggest risk I’ve taken so far was when I moved to LA from Denmark four years ago without having a solid plan. Read more>>

Lisa Guerriero | Documentary & Editorial Photographer

After graduating from Hollywood High School, I began working in the Motion Picture and Television industry as a Camera Assistant. I had a successful career for twenty-five years. In 2014, I took my first enormous risk. I finished my last full-time job on the TV show “Mad Men” and announced to all my colleagues that I was quitting the business to become a photographer. With no contacts, assignments, or any idea of how I was going to make a living as a photographer, I began shooting my street and documentary projects. There is a constant risk when shooting this type of photography. For the majority of my projects, I travel alone across the country, drive through small towns and most of the time, meet strangers on their front porches. Many times I get invited into their homes to chat and eventually I get the opportunity to take more photos. Read more>>

Geo Dillon | Designer, Creator & Owner

Risk is a necessity to start and grow your business but risk doesn’t always feel so good. From my personal experience, taking risks in business can leave me feeling unsure and frightened but I realized that this is totally normal, it’s our thinking mind trying to keep us safe. I have learned to overcome this uncertainty in the following ways. First, do not take your life savings to Vegas and bet on number 7! Educate yourself, do as much research as possible and be honest with yourself, “is this level of risk worth the reward” Use your intuition, it is usually correct. When I started my 1st business, I did my research and purchased the latest engraving equipment and the best brand available, I listened to my educated inner voice which kept telling me that there is a business to made from this technology, I was correct. This was a $30,000 investment which I put on my credit card, not a comfortable feeling. Read more>>

Alexandra DiMarchi | Airbrush Tanning Artist

The biggest risk I took for my career was completely uprooting and moving to the West Coast. I’m from the Washington, DC area, which is mostly known for government-related jobs. Most people there have traditional nine to five careers. But there I was wanting to make it in a beauty industry, so the move had to happen. But it wasn’t easy mentally nor financially and I actually went into debt making that move. So I struggled when I was first starting off and I had to make a lot of sacrifices. Because I’m so far from home I’ve missed a lot of birthdays, graduations, weddings, and even funerals. But I don’t regret these sacrifices because I feel like they’ve all gotten me to where I am today. I’ve always had this burning desire to succeed and have been willing to do the work to do so. Read more>>

Brendan Uegama | Cinematographer

Taking risks is so important for creative satisfaction in your career and personal life. It can lead to growth and artistic/personal fulfillment when it pays off. As a cinematographer.. risks are presented daily on set and with each job I decide to take. Sometimes risks don’t work out.. but that doesn’t mean they aren’t worth it in the long run. Without them, work and life would be rather dull in my opinion. Read more>>

Peter Fenn | Music Producer, Writer & Artist

To me, you can’t build your own business or pursue your dream without risk. The cliche saying really is true, no risk, no reward. When I knew I wanted to pursue a career in music, I was working at Dropbox in San Francisco. It was a comfortable job and a lot of people (including myself) thought it was so risky to quit and go build a career from scratch in music. Even now that I’ve been doing music full time for 3+ years, I am still taking risks everyday. I’m saying yes to working with new people I’ve never met, or trying new production techniques I’ve never tried, or writing a line that’s maybe too honest. Risk plays a big role in my life and in music. Read more>>

Adelheid Waumboldt | President

In my life, the most beautiful discoveries, innovations, adventures and memories have come from risks I’ve taken. The other side of that coin, is that I’ve made life-altering mistakes from risks as well. I find that a risk needs to be calculated: are there more benefits than deficits that will likely occur from this risk? Am I the only one who this decision will affect, or will anyone else either benefit/suffer from this decision? If a risky decision could harm someone else’s life or livelihood I would caution strongly against that. In this world, good intentions are met with good fortune and so anything done with positive motivation and in a spirit of helping will be met with an equally uplifting result. Secondly, knowledge often erases or significantly reduces risk. The more you know of any given topic, the more likely you are to make an informed decision. Read more>>

John Irwin | Filmmaker

I don’t think life without risk would be very interesting. It keeps everything evolving, and continually shifts my perspectives on what’s really important. In any creative project I find worth doing, I know there will be risk- it’s a lot of why finding new challenges feels exciting to me in the first place. I try to push myself beyond what I’m familiar with in every new directing project, and that in turn is the only way to find fulfillment through it. It’s an ongoing struggle, especially since clients that seek me out for commercial work tend to want something very similar to a project I’ve already done. Creative people need to stay vigilant, guarding control over what it is we want to make next. Part of that is knowing how often to say no. With practice, it gets easier to say no to more stable paying jobs and resist being led down roads where the trade for more stability (and often, money) is met with less risk and control. Read more>>

Om Bleicher | Gallery Director

Risk the only way forward into the unknown. The key is to poke around a bit first so its at least and educated risk. But big risks are sometimes needed as well. There is more than one occasion where I’ve had to risk it all to chart the way forward. Read more>>

Cathy Immordino | Photographic Artist & Actress

As as photographic artist, risk taking is a big part in success. When I was just starting out, everything was a risk. It was risky emotionally and financially. I wasn’t sure if what I was making would be collected, loved and cherished by art collectors; but I kept making work. My style kept improving. My concept deepened. Over time, the emotion risk helped me to grow as a person and better understand the poetry of life around us all. As for financially, when I was nobody, galleries, museums and other opportunities were harder to come by. I invested my time and energy in to hiring a team to help fill my weaknesses. I began showing in a lot of art fairs. It was not a cheap venture. Most times, nothing sold. Financially, this was a huge risk for me; but I had put aside money from a former career to cover these expenses. Read more>>

Kyla Wright | Marketer & Entrepreneur

My entire career is built on taking risks. By day, I work in corporate America for a major player in the beauty industry, and by night I own my own lifestyle brand, called Apartment 119. Working a 9-5 and a 6-10 is tough, but it is 100% worth it. Apartment 119 is my way of investing in myself and expressing my creative side, which is a fairly large pivot from my job in the makeup world. My career was built my career from the ground up, and it has been nothing but risk-after-risk from day one. I began as a makeup artist-by-day, who was moonlighting as a creative entrepreneur at night. After several years working around the clock, I also found myself in a long distance relationship. I made a giant move across the country for love and in the process, it also jump-started my career. I was able to maintain my job, and grew leaps within the company over the next few years. Read more>>

Adam McAtee | Pilates Instructor

As Nelson Mandela voiced, “there is no passion to be found playing small and settling for a life that’s less than one you’re capable of living.” To reach one’s potential, they must take risks. In order to do so, it’s essential that we relinquish the fear of failure, and recognize that failure is part of the process of our evolution. One’s success does not rest in their ability to avoid failure, but in their courage to fail. Thomas Edison failed over 1,000 times to make the light bulb, but that isn’t his legacy. His legacy is the successes he had from the risks he took. I’ve taken plenty of risks in my career, and I have recently taken a risk of going back to school to achieve a doctorate in physical therapy. I’ve invested over $110,000 in my education in hopes of creating more in return. It’s easy to look at that figure and call it an awful investment, but how would I reach my potential as a movement educator if a backed away from achieving the highest education available to me? Read more>>

Marguerita Hagan | Artist, Ceramic Sculptor & Environmental Advocate

When your mother finds you walking across the mantlepiece at 9 months, it’s clear from the start that life is an open-armed discovery. Risk? What is risk, really? It’s all relative. It’s never occurred to me to choose “safe” over what I love. Love is an investment so there is no sense of risk. However, it requires focus, listening and following intuition. For me it is a responsibility. It is instinctive. Today, it is more vital than ever. What one cannot risk is allowing life, your path, your passion to pass you by. This quote by Helen Keller was printed on my business card for many years: “Security is mostly a superstition. It does not exist in nature, nor do the children of men as a whole experience it. Avoiding danger is no safer in the long run than outright exposure. Life is a daring adventure, or nothing.” It is hard to imagine the challenges she knew, which makes her insight all the more powerful. Read more>>

Kumar Patel | Founder & CEO

Risk is a part of life. Humans have come up with a numerical value and labeled it as “odds.” When the odds are against you, it’s deemed “risky.” Most people consider skydiving to be very risky…but if you look closely, the odds of you dying are only 1 in 100,000. However, the chances of getting in an accident every time you drive are about 2 in 100. So, to put it in perspective, driving is riskier than skydiving. “90% of new startups fail. 75% of venture-backed startups fail. Under 50% of businesses make it to their fifth year. 33% of startups make it to the 10-year mark.” – Forbes. It’s about using the data to put the risk in perspective – and the data can range from general market research to case studies to a conversation with an industry veteran. The goal is to find things that work to reduce the risk. We don’t stop driving – so I don’t expect to stop driving my company forward. I embrace the risk by learning, understanding, educating, and implementing new theories. This is how you turn the odds in your favor and keep innovating. Read more>>

Emily Burton | Musician & Silversmith

I’ve always taken the “no risk, no reward” philosophy to heart, but I’ve had to reconcile that with the “be prepared” motto of any proper Girl Scout. Marrying the two I find that I like to take calculated risks. A few years ago, I felt stretched too thin and decided to leave my secure agency job to try to find more life balance freelancing and pursuing other artistic callings. I won’t say that it wasn’t extremely scary, but I had financially and mentally prepared as much as I could and knew I was at a “now or never” moment. Since then I’ve been able to partake in so many projects, adventures, travel opportunities, artistic and musical endeavors, and friendships that I wouldn’t otherwise had the time to pursue. It also set me up to be self-reliant and diversified enough with my business to weather the unforeseen challenges of 2020. Read more>>

Portlynn Tagavi | Writer & Director

Risk is the secret sauce to the ultimate reward… growth. I find myself in a constant balance between two states of being, comfort, and discomfort. It’s something I struggle with. The desire to grow and progress in my work is always at odds with my desire to continue with things the way they are. When I graduated from Cartoon college in 2014 I was presented with opportunity after opportunity in the animation industry. I was making money and working my way up slowly, but something was missing. I really wanted to work in live-action as a director but I was scared. I was scared I wouldn’t be good at it. I was scared it would be a waste of money. I was scared people would judge me if I failed. I would have judged me if I failed. I had put off pursuing this goal for a few years until the level of stagnation I had felt with my path had become too much. I pushed through my fear of taking the leap and applied to AFI’s directing program a month before the due date. Read more>>

Hilary Lentini | Founder & Creative Director

Taking risks is how you get ahead in business. Every impactful growth opportunity in building my business came from my leaning into risk. Starting my firm was a risk. Hiring my first employee was a risk. Taking on my first business line of credit was a risk. Now, decades after taking risk after risk, it’s much easier to go ahead and make that tough call. That said, even know, when I see an opportunity in front of me that scares me, I know that’s a sign that it’s a risk. And the more scared I am to take that path, the more I know I should take that path. Because that’s where my and my firm’s growth lies. For me, there’s almost always been a reward after the risk. Read more>>

Jamie Koplin | Artist & Veterinary Technician

When I think about risk, I think about all of the things I’ve accomplished by taking risks. I wouldn’t be where I am today if I didn’t take the risks I did. I used to be agoraphobic, but now I can travel and even moved across the country to start a new life here in LA. Risks are essential to my artwork as well. Working with watercolors and ink is always risky. Things just kind of move where they want to, and the end result is never exactly how I pictured it. Some of my favorite artworks have started as one idea, but surprised me by doing their own thing – turning into something completely beyond what I imagined. I surprise myself when I take risks, and I think a person can only grow by taking risks. Risks have taught me how to be a better artist, a better person, and how to cope with changes in a more mindful way. Read more>>