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.

Michael Glines | Musician, Music Teacher & Videographer

Everybody takes risks all day every day. Every decision you make, you’re taking a risk. I remember people telling me when I was younger that the odds of making a “making it” as a musician were not very good. For every great band that you hear about, there’s a thousand bands just as good that you’ll never hear about. But for some reason as a kid I didn’t let that deter me. Maybe I didn’t know how badly I sucked at the time, or maybe I just knew that everyone who ever made it had to believe in themselves despite the odds. And anyway I felt like I’d rather fail trying to do what I wanted than succeed at anything I didn’t want to do. So for me it wasn’t really a matter of risk-taking. I could have just as well failed at anything. People drop out of law school or medical school every day. Engineers get fired from their jobs every day and have to figure out how to make it. There really is no true security in life. Read more>>

Lelia Symington | Actress & Singer

Risk is built into the life a professional artist. Most actors don’t know where their next paycheck is coming from, and there’s no guidebook that says “Do this, and you will be successful.” I’ve wanted to be an actress since I was 5 years old, and so I sort of wove risk into my life from the start. Whenever a teacher asked “Who wants to go first?” my impulse was always to shoot up my hand. Backpack? Move to LA? Try this weird food? Karaoke? Yes, yes, absolutely yes. And it’s not as if I am fearless. Not by a long shot. It’s that I have trained myself to act before the fear gets too loud. Of course as you get older you also train yourself to differentiate between risk and danger. It’s not a perfect science, but all of the things I am most proud of came to be because I took a risk. Read more>>

Michaeline | Celebrity Hair & Makeup Artist

I’m pretty sure that most people become more risk averse as they age. It’s funny because I’m the opposite! When I was younger, I was too nervous about the potential consequences of taking risks and thought that venturing even a little bit from my path wasn’t even an option.  With more life experience, I’ve come to admire risk-taking.  I like the process of weighing my options, debating the pros and cons, asking others their opinion and understanding that life doesn’t have to be a straight shot. My whole career as a makeup artist was built on a leap of faith.  I had no experience as a business owner or friends in the creative field.  I knew that I wanted to succeed and that was enough.  I left my job as an engineer to pursue my passion. I treated it like a do-or-die scenario. I honestly gave myself no option to fail, but of course it was a huge gamble to leave security for a dream. Read more>>

Amber Rose | Hair & Makeup Artist

I never really thought of myself as a risk taker in my personal life- but in my career I’ve taken quite a few. I grew up in a very small town (pop. 67) in Southern Minnesota where a lot of people in the area are born, get married, have kids and choose to spend their entire lives there. From a young age I knew I didn’t want that, I wanted to be in the beauty/fashion industry and knew I would have to move to a bigger city to achieve that. California was always the goal but I never thought it was in the cards for someone like me…a low risk taker, small town girl from a low risk blue collar family. Moving to Minneapolis for Cosmetology school was my first ‘big’ risk (and scary for me at the time) but well worth it. After graduating from the Aveda Institute I worked in a few salons for 5 years but didn’t feel fulfilled…I wanted to be doing hair and makeup on set for models, actors and celebrities. Read more>>

Kim Kovacs | CEO

Many would think that getting into the cannabis industry was one of the biggest career risks I’ve made, but for me, it was a very calculated and planned move so not that risky after all. I am actually very risk-averse. I keep most of my investments in cash vs the stock market and I hate leaving things to chance. I use data to help me make decisions and take the emotion out as much as possible. Good data and a little foresight will go a long way in helping to de-risk decision making. I also tend to look at risk as an opportunity that most people won’t touch so it makes it actually more attractive. If there are a lot of people doing it and it’s easy, then it will be harder to be successful in my opinion. Read more>>

Trine Churchill | Visual Artist

Risk? I don’t think you can be an artist without it! For me at first it was the quiet risk of a choice spoken, that had already been introduced to me by way of my dad. He was an artist, supporting us, his family, with the cartoons he was creating from his home studio north of Copenhagen in Denmark. Therefore my choice to also become an artist, although not a cartoonist but a painter, at first was not dangerous – it didn’t at the time occur risky, at all. But soon enough, out of art school, Otis College of Art and Design, and now face to face with the big, hairy beast called “reality”, being an artist came with a price of frequent rejections, which in turn fostered self-doubt, and worse – scary little money to get by on. A healthy portion of naivety paired with an unshakable stubbornness along with – fortunately – a true passion to keep making art made me embrace the risk involved, regardless. Read more>>

Sam Glaser | Composer, Performer & Producer

I am risk averse. I don’t enjoy gambling in Vegas or elsewhere because the pain of a loss is too intense. Certainly not worth the upside of a nominal cash prize from winning. I notice among entrepreneurial friends that their risks eventually pay off and offer a degree of wealth far beyond those who play it safe. Any time I’ve made an investment in any enterprise other than my music, it has failed, filling me with regret. Any time I’ve invested in music, however, even if I finish the project in the red, I still enjoy the life satisfaction of the accomplishment. My life isn’t without risk, of course. Making music is a crazy, unpredictable endeavor that challenges me daily to reach my potential and keep my family fed. Overcoming the risk of attempting a challenging project or performing new material for a large audience is an ultimate thrill. Read more>>

Wednesday Aja | Designer & Photographer

Taking risks is essential to creative and personal growth… it leads to unimagined adventures, new possibilities, new friends, and new obsessions. On a whim I packed up my Volvo station wagon, my cameras and drove around the country. I ended up in Austin, TX… and stayed for years. There I worked as a graphic designer for advertising agencies, design firms, and a long and rewarding stretch at a letterpress studio. In the same spirit of adventure and expanding horizons I moved to Paris, France to work with a friend creating visual merchandising for Lacoste. That lead to collaborating closely with fashion designers and photographers, documenting the fashion scene, producing behind-the-scenes photos of shoots for various fashion magazines. One of the fashion designer’s atelier was just around the corner from the world famous Cirque d’Hiver. Late at night, if the wind was just right, we could hear the roar of the tigers. Read more>>

CJ Johnson | Startup Advisor & Content Creator

Taking risks and swinging for the fences has is a way of life for me. I’m a firm believer that fast action will always bring you results. Playing it safe and conservative usually produces stagnation and self-doubt. But if you leap into the unknown, win or lose you’re one step closer to achieving success. As I’ve gotten older and grown my family I take more calculated risks using my past experience and forecasting. I like to think of life as a game of chess where I’m making one move to impact two more down the line. Read more>>

Diana Corpus | Wardrobe & Costume Stylist

Without risk taking, I would not be where I am today. I attended university and earned my BA in Communications and a minor in Anthropology, this was my plan b. My plan a, was to become a wardrobe stylist. When I wasn’t working or attending school, I was interning in Los Angeles and going to events to network. All while living in Corona, CA. I sacrificed my social life and dedicated it to earning my BA and yearning for my opportunity that would eventually land. Through hard work, passion, dedication, and perseverance, I finally had landed my first styling job. From there, my name grew and I started getting referrals. Along my journey, I had no support from anyone when it came to my dreams. I learned early on, I was the one who had to go out and make it happen. Read more>>

Mona Elyafi | Public Relations Communications Specialist & Champagne Expert

To me the word “Risk” means to be bold. Taking a risk is an opportunity to succeed. If you don’t ever chance it you never move forward. Everything in my life and business has always been centered around the idea of “risk-taking”. Early on, when the Civil War started in Lebanon in 1975, my brother and I, amidst the daily bombings, were put on a plane by ourselves to escape the danger. I was 4 years old but very clearly got the sense that the fact that my family and I were taking a leap of faith and throwing ourselves into the unknown was a liberating feeling. Being a risk-taker actually rids you of “fear”. You also become more in tune with your intuition thus opening the door to internal growth, getting to know who you truly are. You only learn and advance in life when you’re at risk. Following a back surgery, I battled a drug addiction (to crack cocaine) for three years. Read more>>

Jake Fraczek | Author, Podcast & Radio Show Host

Risk is merely a part of life. How much of the risk one chooses to, or is forced to engage in, depends on the individual’s experience. Risk for me, I’ve come to know, is woven into my DNA, embedded in my character, an extension of myself as intimate as my astrology or simply my right arm. I could blame my parents. I could thank my parents. The latter feels better. I’ve taken risks my whole life, at times rewarded, and at others punished and condemned, but regret and wonder never lingered as a painful reminder. I embraced risk taking without even knowing probably. Art, Skateboarding, surfing, travel, running the streets, testing the limits, overstepping the boundaries, I was consumed by it all. All of my dreams, desires, and interests, relied upon risk. I felt the fear, as I still do, but have been able to use that burning dread as an energy pushing me towards my eagerness. Read more>>

Zoe Messinger | Writer, Cook & Humorist

Risks, though dangerous, are delicious, like a bowl of pho in Vietnam—you don’t know what will happen (in my case I got a parasite). I live my life inviting risk: backpacking, bungeeing and parachuting out of planes in the wilds of New Zealand (not my natural habitat), moving to Europe to run a food truck at 21; first in Milan, then in Amsterdam (having only spoken Food French), walking into a restaurant for a line cook job in Los Angeles, with nothing but a knife bag and my passion to cook, stand up comedy (the last thing I thought I’d do), and writing—these risks have taken me to a place I can honestly say feels right, maybe even comfortable and joyful. Read more>>

Laura Tate | Growth Marketer, Writer & Editor

If you don’t take risks, you lose the ability to challenge yourself and improve your life. It’s all about balancing the risk with a plan. I took a 100 percent risk in loss of income and stability when I launched my digital marketing agency Crackerjack Scribe more than nine years ago. As a mother of three, I had the responsibility of supporting my family, yet I needed to take control of my life and how I wanted to live it, with more freedom. I wanted the freedom to work from home and from wherever I was around the world. Most importantly, to spend more time with family. So I left my job as editor and associate publisher of The Malibu Times and Malibu Times Magazine. The job was gratifying in many ways—I love the process of putting a publication together from start to finish, and reporting and writing. However, my former boss was old school and believes that if you’re not in the office, in your seat in front of the computer, you’re not working. Read more>>

Angelica Reyes Escribano | Cinematographer & Colorist

Taking risk is what moves us forward, but we need to understand that we are accountable of every decision we make. As a Cinematographer we take risks to make the best product we can; but i need to be responsible with the people that work with me, they need to feel and be safe. Read more>>

Veronica Graye | Stylist & Creative Director

Risk is such a funny thing to me because everyone’s risk level is measured so differently. I am probably riskier than I should be in regard to my career. I began building my business with absolutely no connections and a one-year old strapped to my back. I hustled, I kept my head down, I worked hard and brought my daughter along with me for the ride. I haven’t always said yes, which I know goes against a lot of entrepreneurs advice, and is risky in and of itself. Creativity is a risky career to be in because there is no best in these fields, there is only different, and sometimes different is more desirable. If I had never taken that initial risk of trusting and believing in myself and my talent, I don’t even know the person I would be today, probably a bit more miserable regretting that I never bet on myself. Read more>>

Eliza Swann | Artist, Intuitive, Educator & Writer

My work involves studying, teaching and making art at the intersections of mysticism, mediumship and creative practice. For me, the energy of art and the energy of spiritual practice are evolutionary revolutionary power. When you give yourself over to the lightning of art it is inherently risky – every creative action that I have surrendered to has radically transformed me, brought me into contact with new friends, places, material realities, ideas and vibrations – sometimes I land at the bottom of the sea and find a wormhole into heaven there, Sometimes I land at the bottom of the sea and creatures nibble me into pieces. It took me some time to learn to surrender to the lightning bolts of inspiration – the surrender had been hidden by the competitiveness and success-aggression that my art education demanded. Read more>>

Shaina L. Simmons | Artists & Yoga/Meditation Instructor

Risk taking is a integral step needed to achieving purpose, goals, success, and healing. I have taken several risks over the process of my career as an artists from moving across the country to attend grad school at CalArts ( or even pursuing a Masters in Acting in the first place), or moving to Thailand for five months. Risks have opened endless opportunities for me. I have met the most incredible humans from all over the world and been challenged in ways that evolved me into my destiny. I am currently pursuing my 2nd Masters in Social & Environmental Practice in the inaugural cohort at Prescott College. A program developed by Patrisse Cullors, co-Founder of Black Lives Matter. I took a risk applying, got in, and continue to take risks as I navigate how to afford the tuition in the middle of a pandemic. I started #KeepShainaInArtSchool to lean in on community for support as artists. Read more>>