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.

Chloë Flores

I think about risk differently depending upon how and when it’s applied. For instance, I don’t think of myself as a risk taker when it comes to finances, but when it comes to my curatorial practice, the artist I support, and the choices I make career-wise, I am all in. My decision to maintain an independent curator practice for years felt risky, but it was also done from a privileged place of a dual income household and profitable side hustle. That aside, I have always leaned into challenges, championed alternative forms of cultural production, resisted traditional paths, and been brazen with my choices. Is that risky? Or a product of being othered? Read More>>

Mike Smirnoff

Taking risks is intrinsic to the artistic journey,” I might assert, echoing Kierkegaard’s sentiment that “to dare is to lose one’s footing momentarily, but not to dare is to lose oneself.” It is this fertile ground where creativity blossoms. The act of creation itself is a risk, a leap into the unknown where vulnerability and the potential for failure are ever-present. Yet, nestled within that risk lies the possibility of unearthing profound expression and forging a connection with the audience, the listener. A life devoid of risk, as Kierkegaard suggests, is a life incomplete; it is in taking chances that we truly discover the breadth of our capabilities and the depths of our artistry. Read More>>

Timothy White

I tend to be more reactionary to what is going on around me. Consequently, I stay open to the process and circumstances as they arrive. I am confident that I can handle any situation, in fact, I thrive on the not knowing where a particular experience will take me. There is a risk to that, and it keeps me open to inspiration. As a portrait photographer, I need to be free to see my subject in the moment, and to find that something that allows them to open up and react to me and their surroundings. Read More>>

Chyrah Brooks

Mark Zuckerberg once said “the biggest risk is not taking one” ; and that’s how I view risk now. I used to procrastinate so much that I would never elevate mentally, emotionally, financially, spiritually, physically, or academically. Risk taking is playing a significant role in my life right now, becuse I just recently moved to California from Nebraska : and working towards my dreams at a rapid pace. Read More>>

Leah Avigdori

Growth and expansion can only happen by taking risks and pushing yourself outside your comfort zone. A year ago, I was presented with the incredible opportunity to take over a beautiful bungalow in Beverly Hills. While it was an incredible offer and a dreamy location, I immediately said no facing the reality that I didn’t have the funds to renovate or manage the costs. But I moved forward with certainty and just when I thought I was about to step off into the edge of failure, the universe came through exactly when I needed it most. Read More>>

Bria Clark

You’re losing money right now—and not because of what you did, but because of what you didn’t do. Anytime you forgo the opportunity to indulge in brining your creative thoughts to fruition, you’re willingly dismissing SUCCESS. When we analyze the root cause of what holds many people back from greatness – it’s based in the fear of loss. To overcome this mental block, I trust in my ability to recover more than I fear failure. I have FAITH that overcomes my FEARS! Read More>>

Jayy

Risk-taking has played a huge role in my life. Every day brings new risks and opportunities to navigate. One of the biggest risks I took was pursuing a career in modeling and acting. Looking back, I’ve accomplished so much more than I initially expected. Taking this leap has not only brought me success, but it’s also given me a deep sense of accomplishment. I’m finally doing something I’ve always dreamed of. Read More>>

Sejoya Thomas

I think in life you have to take risk! Especially when you have faith that you will win, go for it! Read More>>

Javier Vasquez

You have to be willing to take risks. There’s opportunities that come by, and you have to be ready to take the risk and jump on it. These opportunities don’t come back so one doesn’t have to fear the risks, simply be ready and when your time comes you will know how to handle it. When the chance came up to buy our restaurant there was some concerns, seeing as we had more experience in the food truck business. We believed in ourselves, our products and our brand that we decided to give it a try. Read More>>

Boston George

You gotta take risks to win big chances make champions Read More>>

Lily Koen

I believe risk is critical for high reward. If you’re not doing something that challenges or scares you a little, then what are you really doing? Growth—both personally and professionally—comes from stepping outside of what’s comfortable.

When our company got funding, I had a choice: stay on a path that was stable and familiar, or take a leap into something uncertain but full of potential. I chose to take a leave of absence from UC Berkeley, a place where I excelled, had an amazing community, and felt secure, to pursue a once-in-a-lifetime opportunity. It wasn’t easy walking away from something I had worked so hard for, but I knew that the biggest rewards come from betting on yourself and the things you believe in. Read More>>

Sarah Hassaine

My relationship with risk, in retrospect, has been beautiful. I would have never pegged myself as a risk-taker. However ironically, the instances in my life where I took huge risks ended up being the best thing for me. They were scary in the moment. I look at risk as a mindset. I know that there are consequences or uncertainties and I tell myself that I have what it takes to navigate them. I calculate the opportunity cost. The biggest risk I took was walking out of a job without another one lined up. Read More>>

Kelly Pantaleoni

Risk is not something I think about, so i’ve done a lot of risky business. A few years ago I packed up my life in Los Angeles – putting everything into storage and booking a one way ticket to Cambodia. I backpacked southeast asia solo for two months living off street food and traveling with people I would meet in hostels. It saved my life during a particularly depressive episode after losing my best friend to suicide. Most people in my life did not understand it, but I knew it was the best decision for my life at the time, despite the risks and safety concerns. It turned out to be the best adventure of my life and one of the best decisions i’ve ever made.  Read More>>

Andre Almeida

When my wife and I decided to open our first business, we were starting from scratch. We didn’t have enough capital (I had to take out a $100K loan with my grandma), we lacked experience (we were just 24 years old), and, honestly, we weren’t fully prepared. But what we did have was an unrelenting drive to succeed, and we were willing to do whatever it took. Long hours were the norm—working 12+ hours a day, 7 days a week—because we knew that dedication was our ticket to success. Read More>>

Corey Peters

Risk-taking is a way of life for me, and is deeply integrated with my philosophy of how I want to contribute while being alive on this planet. I understand that “risk” has multiple interpretations and my methods of risk-taking may not be conducive to someone else’s and vice versa. The biggest risk in life would be to not do the things I have passion and energy for. This gives me tremendous motivation to fight for spending as much time as possible doing the things I love. Time is my most limited and valuable commodity.  Read More>>

Aja Dawson

Risk analysis has always been an interesting process for me. Over the past few years, I have been trying to reverse engineer my process for decision-making and how I make decisions on next steps. I have been operating my business, (abeautifulife) Jamaican, for 12 years and I have found that “gut feeling” and intuition are always going to guide you in the right direction. There is always going to be risk involved in anything that is worth pursuing. Grit, stamina, and timing make risk become less of an obstacle and allow space for the belief in self to come to center stage. All things are possible to the tenacious and determined. Read More>>

Douglas Clarke

I view risks as leaps into the unknown. Even if a general goal is the purpose and driver behind a decision, the fear I may feel that turns the decision into a risk inherently indicates the discomfort that the unknown of that decision brings. When thinking about growth and expansion, I understand that if I’m only recreating experiences that I’ve had in the past, though it may feel comfortable, I am severely limiting what new knowledge I will be able to acquire. Read More>>

Carrie-Ann

Risk and me? We’re old friends. As an improviser, I’ve spent decades leaping into the unknown with nothing but trust, a ‘yes, and’ attitude, and the belief that something magical will happen if I stay present. That philosophy has shaped not just my career, but my life.

Risk is the spark that ignites creativity, the necessary leap before you learn you can fly (or at least land on your feet). Whether it was co-creating The Second City’s Los Angeles Diversity in Comedy Festival, expanding YADA’s programming, or diving into executive leadership, every big move I’ve made came with uncertainty—but also immense possibility. You just gotta get out of your own way. Read More>>

Rosslyn Castro

Risk Taking: Embracing Uncertainty for Growth and Purpose

When I think about risk, I see it as an essential ingredient for growth—both personally and professionally. Risk-taking is not just about stepping outside of your comfort zone; it’s about daring to pursue what truly resonates with your heart and soul, even when the odds seem stacked against you. It’s about having the courage to believe in your vision, even when others doubt it. Read More>>

Jessy Richmond

Risk-taking is the most important thing when it comes to growth. If you’re not willing to take risks in life, how are you ever gonna grow? It’s the same in your career—if you wanna be the best, you have to do the things that will make you the best. DM that brand, buy that camera, upload your content, email the clients you wanna work with. There will always be one yes, but you’ll never get it if you don’t put yourself out there. Read More>>

E.m.

Risk-taking is an integral part of both personal growth and professional development. When I think about risk, I view it as a balance between opportunity and uncertainty. Risks can often lead to new experiences, innovation, and unexpected rewards, but they can also come with challenges or setbacks.
I am definitely a risk taker, but only when my gut feeling gives me the green light. I do believe that if your inner compass navigates you towards your dream or happiness, then you should definitely make the leap and go for it. Read More>>

Alina Harmann

In a feat of admiration for an actor I deeply respect – though our paths will likely never cross – I borrow from Tom Selleck, “Risk is the price you pay for opportunity itself.” The Tom Selleck fandom runs deep in my family. After all, my mother “broke up” with Paul Newman to crush on Tom Selleck when Magnum, P.I. debuted, so I was reminded of his words as I embarked on my journey as an actor and moved to LA. Read More>>

Rhea Mahajan

For me, risk-taking isn’t about reckless leaps—it’s about making informed decisions based on deep research, pattern recognition, and trusting that no one is going to build the life I want except me.

1.) My First Big Career Risk: Leaving Accounting

For years, I followed a structured path—majoring in Accounting and Finance, becoming a CPA, and landing a stable job in forensic consulting. It was a career with clear steps, but after two years, I knew I wanted more. The idea of leaving something so secure was terrifying, but I didn’t make the decision impulsively. Read More>>

Angelina Kovach

I have made many bold and risky decisions throughout my life. From leaving my hometown at a young age to move across the world, to exploring different paths that intrigued me, I have always embraced uncertainty. I believe that without the willingness to take risks, I wouldn’t be where I am today.

Becoming a content creator was one of those risks. Back then, it wasn’t considered a career—there was no clear path, no defined profession. We didn’t fully understand where this journey would lead. It was similar to moving to America—stepping into the unknown, uncertain of what the future held. Yet, every risk I have taken has shaped me, pushing me toward new opportunities and personal growth. Read More>>

Khrissy Briscoe

Taking risk is so important because nothing grows in your comfort zone. My entire career I have taken risk and trusted GOD throughout the process. I’m very persistent with every goal I give myself. My biggest accomplishments have thrived from me not being afraid to fail. Once you shift your mindset and start looking at things from a different POV, you’ll see how much more further you can go. Read More>>

Arnaud Rebotini

For me, risk taking is the root of creativity, it’s the way to create something new, something personal.
I often take risks in my career, for me it’s also my way to express my artistic freedom, I’m never afraid to sometimes surprise or even be where people want me to be. Read More>>

Max Devereaux

Hello thank you for your question. I think about risk taking as being fundamental to an artist’s journey. Because artists are ultimately expected to invent, it is very important that you are always finding time to experiment and journey into unknown territory. This exploration is essential as a means to broaden the scope of your own creative output and thus potentially expand the possibilities in your chosen artistic field. Read More>>