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.

Alexandra Covucci | Integrative Leadership Coach for Entrepreneurs, Creatives, Leaders and Coaches

I’ve taken a lot of risks in my life from hopping on a one-way ticket to South America at the age of 22 with only two bags, to starting my own business and following my passion, to ending an engagement with my then-partner and best friend because I knew it wasn’t right for either of us. Each risk in my life has had its own flavor, its own life-force, and its own reasoning. Where some risks were impulsive, others were the result of months of meditating on a decision. Read more>>

Justin Hart | NAACP Image Award-Winning Producer

A wise man once said, “The biggest risk is not taking any risk. In a world that’s changing really quickly, the only strategy that is guaranteed to fail is not taking risks.” This particular motto was implemented into my life once I sparked interest in the entertainment industry at a very young age. When taking a risk, you’re blindly inserting yourself into a space of “not knowing” but fully enhancing the ideology of “Faith” and trusting the path you created will lead you to your destiny. In 2011, I was a Senior at Middle Tennessee State University and I made a vow to myself to either move to Los Angeles, California or New York City post-graduation. Read more>>

Donna Isham | Fine Artist

I’ve always been a risk taker in my life and yet the idea of committing to being a fine artist and putting my paintings out there was some thing that I thought was insurmountable. But after much soul-searching I realized that it would be more painful to not pursue what I love. Hence, I begin painting and basically told my friends and family not to tell anybody… Well you can only guess what happened after that. Suddenly I was being asked to do art shows and exhibits and selling work! Very exciting, very daunting! And I continue to take risks in my artwork and what I want to create and put out into the world- Beauty, the renaissance of women, the uniqueness of individuality and the quest for organic materiality in a highly technological age. Read more>>

richard jordan | casting director, actor, entertiner, creative stratigist

People who play it safe all the time don’t have any fun, they may have more money, but they’re not having fun with it. Of course you can have both. If you’re not taking risks you can’t innovate, you’re just following the guide and not changing with the times. Let’s be honest here, the dedication to a life of show business is a major risk with guarenteed failure even for the best of the best. Growing up I was deeply unhappy and that started to change when I began to say “fuck it’; i’m going to do this my way.Yeah, I’m going to miss out on my senoir year and live in France and yeah I’m going to move to Mexico to work at Club Med instead of staying in the state for a 6 month probation after a minor mairjuna arrest and tkae it on my record for 10 years. Read more>>

Jeff Lam | Producer & Actor

Interesting enough I was raised in Hawaii by 2 very loving and very Asian parents. So risk taking wasn’t a part of the Asian culture. You went to school, graduated and either became a doctor, engineer or business major. So I always had that fear of disappointing and playing everything safe. I’ve always had this dream of going to Hollywood and becoming an actor. But it wasn’t till 2000 that I decided to take a risk and moving to LA to pursue my life long childhood dream. Mind you, I had no friends or relatives there. It was a leap of faith that I believe changed my life/career forever. Read more>>

Devonric Johnson | Entertainer | Fitness Pro

Risk is something I believe that must be taken in order to achieve your goals. After suffering a career football injury, Post Concussion Syndrome, I was lost and didn’t know what I was going to do with my life. After trying different jobs I got scouted to model and took a risk and moved to New York which eventually led to me coming to LA. Fast forward to now, if it wasn’t for that risk I took, I would have never never found my calling in Entertainment and Fitness. I have been in several Films, TV shows, Commercials, Print Ads and have been on several platforms as an On Camera Fitness Trainer. I also have been the Head Trainer at several gyms and have been lucky to have several celebrity clients. I would have been able accomplish things without taking a risk. Read more>>

Eugene Hutchins | Arts Director

Risk is a calculation. It’s about the magic word “if.” And understanding what could happen or should happen if I choose what path or another. Being involved as a professional in the world of arts and culture is a risk because it is unpredictable in many ways, but I believe there are ways to mitigate the risks by being prepared and seeing how your actions fit into the big picture. For instance: I have a BA in Dance from UCLA and a MM in Opera Stage Directing from Florida State University. Read more>>

Ali Manning | Food Scientist & Consultant

“If you are not willing to risk the unusual, you will have to settle for the ordinary.” – Jim Rohn. I’m a firm believer in taking risks, yet sometimes those risks are not always calculated. I was “set free,” a fancy word for fired from my job back in August of 2019, and I knew I was about to embark on a transformation. I describe it as a wave of joy and peace rushing over my body. See, I didn’t quite rush off to find work; I had been a shell of myself for so long that it was important for me to discover who I truly was and rediscover what I liked to do. So, After months of self-care, inner work, and constant meditation Umami Food Consulting was birthed, and I finally felt like I was on the path to realizing the risk. Read more>>

Daniel Suk | Artistic Director and conductor

I think there is always some risk in everything you do, especially if it’s something new. My life has been constant: Going to unknown places Learning new languages Meeting a total stranger Starting a new career Starting a new relationship Building companies Everything I did was an adventure, but for other people, it was a risk. Read more>>

DJ SWANZY | DJ, Artist , Producer, Entrepreneur

Risk taking is probably one of the difficult task, or thing to do, the feeling of uncertain is what makes it hard. The What if factor is the thing that will drive you to make the decision or not. The one thing I learn about taking risk, is I always tell myself what do I have to lose, and why not, its either the decision gets made, I learn from it, or I would never in the world know what the outcome will be, so most of the time, when I personally take risks, I go for it, because I never know what it might lead to, not taking it at all and living in fear can also cost you a-lot. Read more>>

Jamilah Lang | Professional Organizer and Interior Stylist

I’ve never like to play it safe. I’ve always been the one that with the optimistic attitude of “let’s see what happens.” When I was younger, risk taking was easy. If I failed, I was young and hopeful enough to pick myself back up. If I succeeded, it only boasted my confidence and I was ready to make my next move. But risk taking became life altering once I had children. While having a young son, I took a major risk and left my corporate career to pursue my entrepreneur dreams. It was a risk, but I was confident in my abilities. What followed were major failures, financial depression, and my darkest days. I thought I’d never recovery. These dark days eventually lead me on a spiritual journey, which led me to my current career and passion! I mean, it was tough! But, I thank God for the hard lessons learned. My work now is so aligned with my soul purpose. With this work, I feel grateful and lavishly blessed everyday. Read more>>

(Chris)tina Havis | Director of Development/Talent Manager

Great question, risk-taking is fundamental in entrepreneurship. The risk-taking started early in my journey. For me, taking a risk was as simple as having the audacity to think for myself. The first risk I made was the decision to leave my career in law enforcement and move to LA. That first risk and leap set the foundations for where I am today. Risk-taking has always been easy for me. I always felt if you want a reward for your risk you got to do the research. Haha, I guess you can say I’m more of a calculated risk-taker. I knew applying for a position at a global talent management company was risky. This is due to my lack of formal education and years of experience in the entertainment industry. Read more>>  

Shardul Sharma | Film & TV – Producer

I believe that taking risks is a part of everyone’s life. Winning and losing are both equal parts of the game and I believe that regardless of the side you find yourself, you have already come ahead from where you were before the game. So, according to me the key to success is to always believe in yourself, take the steps ahead and don’t be afraid of failing or what anyone or everyone will think if you do not success. Like Billy Wilder said “Trust your own instinct. Your mistakes might as well be your own, instead of someone else’s.” Read more>>

Raheem Amir | Chef/Entrepreneur

My whole cooking journey so far has been full of risk. From Deciding not to pursue a Childhood dream of being an entertainer to developing and building a passion for something even bigger than I could ever imagine. The Risk of missing out on the things an young man looks forward to being apart of, from quitting jobs because I felt stuck and like I learned as much as I could. Being an entrepreneur comes with a list of risk some a learning experience and some extremely rewarding but, all definitely not understood. These very risk I speak of have gotten me where I am today, taking those chances on myself , believing in myself enough to know I deserved so much more. I went from people talking down on me for staying at jobs for months at a time because I felt stuck after reaching my learning capacity. Little did they know that these very jobs were learning steps needed to gauge own career. I’m well versed in the kitchen and I owe it to the risk that we’re taken along with the people who supported those risk, my family. Read more>>

Rachel Lorin | Singer/Songwriter/Dancer/Actress/Model

I think risk taking is absolutely a necessity for any budding artist. It allows you to think outside of the box and take chances on yourself. I will always bet on me. Taking leaps of faith may not always work, but a lot of the times I have been pleasantly surprised at the miracles that have come. If I fall, I’ll fall on my feet and try something else. Nothing wrong with trying again, as long as you’re trying. Risk has played a massive role in my career as I’ve changed genres a few times against the will of labels and management. I followed my own intuition and gut even though it cost me quite a lot of special and prestigious people in my life. I’ve rebelled so many times, taking chances on new sounds and new music even though others didn’t agree and it always turned out better than I could dream. So, that all being said, risk taking is very important to me. Read more>>

Aaron Jay Rome | Actor & Filmmaker

I don’t live my life a quarter mile at a time, but I do recognize that I only get to live life one time (that I remember). A life which consists of a constant barrage of options. I often picture myself in my deathbed looking back at life, satisfied, knowing I got here making the boldest choices I could, given my options at the time. This isn’t to say I run through 10 lanes of traffic, swim with sharks, or eat only expired meat on a daily basis, but when it comes to career goals and life choices I’ll usually always opt for what has the greatest reward. Read more>>

Adam Sartain | Actor, Voice Actor, Producer

When I think of risk taking, I think of a Poker game. You can’t win unless you take a risk, so take the best risks you can. I left a career with the State of California, a house, and seats on 3 different non-profit boards 5 years ago to come to LA so I could start a full-time career as an Actor and Voice Actor. I cashed in my retirement a year and a half later so I could stay. I have made risk after risk. Sometimes the little risks have paid off, sometimes they haven’t. But I have yet to see if the biggest risk has paid off. So far, things are looking pretty good. Within 2 Months of moving to LA, I had an agent. Read more>>

Jacob Gago | Music Producer

Most homes teach their children – go to school, get a job after college, get married, save for retirement blah blah blah. I thought by following this safe system I’d be happy, make my family proud and be set. I worked 60-70 hours per week as a CPA (Certified Public Accountant) for one of the largest accounting firms in the world making close to six figures. It wasn’t long till I realized me playing it safe by working for someone was actually fulfilling their dream. This is the riskiest decision someone can make in their short life span. One day on my way to work a friend sent a post of an elderly lady on her death bed saying the biggest regret she had in life is not living her dream but enslaving herself working for someone else. This dramatically changed my life on the spot. Read more>>

Edit B Kiss | Holistic Mentor, Success habit coach and founder of Release with Ease.

I am the kind of person who grows wings while jumping off the cliff. I always been a dreamer and I had influencers around me who gave me good ideas or trends to follow. So that made me believe that what is possible to achieve: if they can – I can. I also love the variety in life. I got bored if I do not have enough stimulus. So I went through life learning by experiences. I am a cosmopolitan lived in 8 countries and visited other 13. I have two children and their presents did slow me down at the beginning of my family life because the society made me believe I need to provide them a steady life and keep them in their comfort zone which made me physically sick because I let myself controlled by the people around me. Read more>>

lilo (aka lilo on paper) bergqvist | Artist

My friends always say that I have lived multiple lives in one lifetime, with all the experiences I have had. (And no: I am not THAT old! Lol) I knew from I was a teenager that I didn’t want to sit in my rocking chair as an old lady, thinking back of all the missed opportunities I didn’t take and on the life I didn’t live. So very early on I promised myself that I would never live a “what if” life. I quickly learned that it is essential to take risks if you want to grab the opportunities you are lucky enough to get. Read more>>

Kelly Mazzotta | Brand Strategist & Website Designer

“To live a life of excellence, you will have to take risks. You will have to step into new territory and climb new mountains. If you’re up to something as big as you are, it’s going to be scary. If it feels safe, you’re probably underachieving. To leave a mark in the world, you will have to stand some place you’ve never been willing to stand before.” – Debbie Ford Risks can be scary and invigorating and terrifying and jeopardizing and rewarding all at the same time. Read more>>

Sara Kinney | Cinematographer

Risk is everything. I think it’s important to take a lot of risks, both in life and in your career. I try to say yes to everything, and figure out how I’m going to actually pull it off later. I collect experiences; I’ve rafted the Grand Canyon in winter, rode my bicycle around the perimeter of Iceland for fun, and I once quit the only day job I ever had, sold my belongings and moved to Berlin. I try to say yes to all opportunities and then I figure out how I’m going to actually pull it off.
My risk-seeking inclination has taken me all around the world shooting various documentary projects. Read more>>

Nikkilette Wright | Professional stuntperformer

According to the dictionary “risk” is a situation involving exposure to danger. By definition I live my daily life with risk. Even though I have just gotten into Stunts five years ago I have always been a risk taker. Without risk, life would be very Mandane. Granted my life involves much greater risk than the average person, but I would like to think my risk are very calculated. The spirit of courage was stalled in me from my mother, from a young age. This spirit helped push me two sell my car, house, leave my job at 14 years and move to Los Angeles to pursue a career I knew very little about. It was because of this courage and taking the risk that I was able to achieve a career and Stunts in Hollywood and living the life of my dreams.. Read more>>

Anuj Jamadagni | Filmmaker

I somewhat believe in what Elon’s musk says “ we are probably living in a simulation”. Life is full of opportunities and chances. Opportunities to be happy and successful and chances to change something for the better. Once an opportunity reveals itself to you, grab it. If you have a deep will or desire for anything, you’ll attract those opportunities automatically.That’s the secret. Read more>>

Serge Gay Jr. | Visual Artist

Risk taking have always been the biggest thing to me, when I started my career as an artist. I’ve always told myself to not be safe, to not continue doing the same repetitive pattern that is taught in school: “to create one significant style”, that’s just not me and not always true. Risk taking gives me that sense of freedom and makes me this innovative storyteller. Which adds new elements to help me grow as an effective artist and a better human being. Taking risks also helps me do things that are critical in society that is not talked about in this field than doing just pretty art. Read more>>

Crystal Loverro | Actor & Model

Some of the best experiences in my life have come from taking risks. I consider myself to be a go-getter and a risk taker. Switching from the medical field to the entertainment industry was a huge risk for me, but I am so grateful that I made the transition. I am a firm believer in the saying, “you won’t know unless you try.” We are in control of our lives, and we are one decision or risk away from breaking the stagnation of a mundane routine. I never want to look back on my life and wish that I did something that I chose not to out of fear. Read more>>

Amy Williams | Director , Producer , writer

Without risk there is nothing, Reach further than your grasp is my thing. No Success, change or growth comes without risk. Have to believe and stay in belief of what we are creating , working towards and fighting for . Never giving up in the task at hand. We can’t know ever if we don’t try ,with an open heart and give it our all in good faith. Read more>>

Jalen Ty’ron | Singer, Songwriter, Actor

Taking some risks is the only way to “live”, to me. If you’re always in a place of comfort and complacency, then you will never fully realize your true power. I took a huge risk four years ago by moving here to LA at 18 yrs old because I believed that there was a chance that I could be the person I saw in my dreams. No, every day is not sunny and I want to give up sometimes but my love for what I do will always be bigger than my uncertainty. And seeing where/who I am today, I will always applaud my bravery. Conquering risks is one of the best feelings ever, especially if the odds aren’t in your favor. I’m not saying go and do something crazy, but always be intentional. And stand firm in your decisions because the outside noise and doubt will always try to creep in. Read more>>

michael foulkrod | artist painter contemporary realist

Even midgets started small. We start at the beginning “tuff” but understand it won’t last long.The key is 3 phone calls before 12pm everyday towards what you want.Even if someone cant help you ,call them back in 2 weeks just to say hello thus relationships are created. I cant help you but i know some who might will begin to happen. Research and then more research in how to focus your target people.i walked into the top people in my field telling them i dont yet understand everything but i am honest and happy to be of service. people are attacked to honesty you dont have to do a song and dance act because they will see it. After 35 yrs at one thing i decided to go full time at another at the risk of not making it but somehow based on my experience i knew i had to find my new circle of people to bounce off of till i could do for myself Read more>>

Jordan Serpentini | Creative activist

I look at risk like fruits on a tree. If there’s a certain fear I have with doing something, anything really, that means that fruits for me. For within the doubt and the fear our mind says, lies a task of growth to expand out of just our heads. Pushing us further from our head into our hearts, and giving us strength to make amends with our dark. So risk is a part of this human game or a simple step on the ladder. Where what you focus on materializes. Within this game you have to jump before you pull the parachute, dive into trust and self understanding first which keeps us in our most illuminated and activated state. You don’t need risk to be successful by any means however you do need the tension of fear to overcome in order to embody worthiness of receiving your dreams, living your truth and finding life’s ultimate connection. Read more>>