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.

Deb Leal | Artist & Director

I found that time and trust are keys to better understanding the personal risks I take for my practice. It takes time to know yourself and the goals you have at large, which informs decision-making when considering risks both big and small. Much of my risk-taking involves diving into new environments: The same way I dove into living and working in the San Francisco-Bay Area was the same way I dove into New York City ten years later– with two checked bags, a carry-on, and a very loud belief that whatever is to unfold will only benefit the photo work I set out to do. Change is good to stay curious and always find your way back with new eyes and experiences. Read more>>

Hisham Dahud (aka Rizik) | Creative Catalyst: Founder, ArtistPro | Musician & Producer (RIZIK) | Music Marketing Veteran

When you possess crystal-clear vision, what may seem like a risk to others transforms into a necessary move. To me, risk isn’t just a blind leap into the unknown—it’s a calculated step toward something you can clearly see, even if no one else can. The fear doesn’t go away; it sits there, looming, but becomes something you learn to overcome or at the very least manage, because you believe so deeply in the path you’ve envisioned for yourself. Read more>>

Brandon Glova | DJ Bonics – DJ / Radio Host / Producer / Brand Ambassador

Taking risks is the jelly and the jam. That’s where the magic is. I often reference the time I quit my radio job as the afternoon host on Pittsburgh’s 96.1 Kiss to tour with Wiz Khalifa full time. That was a choice that changed my life forever. When i had to make that decision, my sister offered me the advice of “no risk, no reward.” The risk is is what makes “the movie.” My decision set me up for an adventure of a lifetime. I’ve touched stages around the world and been to places i thought i’d never been. Follow what makes you feel! Read more>>

Erika Klash | Drag Artist

I fell in love with the art form or drag as soon as I turned 21 and was able to go to bars & clubs to see drag shows. As a theater kid and theater student, I saw the opportunity to sort of be a one-person theater company. That’s reflected in my work today, where I custom edit my performance materials and make the most out of venues’ lighting and visual capabilities. Read more>>

Halim Lee | Multidisciplinary Graphic Designer & Educator

As a multidisciplinary graphic designer, I believe creativity thrives when we embrace risk rather than fear it. I explore new possibilities in graphic design by blending various media, from print to digital. While some attempts may fail, each new endeavor brings valuable knowledge and lessons that lay the foundation for better future projects. The greatest reward I gain from this process is the pure joy of creation. Read more>>

Marguerite Truckey | Producer

I believe that without risk comes no reward — taking risks in my personal and professional life has been daunting but in many cases, has turned out to be the next step in success, as I walk down my path in life and film. Moving across the country, falling in love, jumping into a new workplace — these are all moves that took courage. The biggest since moving out to California has been the transition from director to producer, one that has really transformed my relationship with the industry, but has also made me a stronger creative and efficient director (when I switch back for a project or two). That goes to say, some risks haven’t paid off, and therefore didn’t feel rewarding nor electric. But those risks didn’t pay off, those little “failures” i’ve experienced…ultimately, they led me to the place I am now, so in their own ways, they were stairs to my steps of success. And I need the stairs! Read more>>

Marcus Wooling | Dancing Accountant

Risk is a powerful catalyst for growth. For me, taking risks has always felt like a leap of faith—but that’s where the magic happens, right? For me, risk isn’t just about throwing caution to the wind; it’s about stepping out of my comfort zone with intention. It’s scary, exciting, and transformative all at once. In my life and career, risk-taking has been a constant companion. Balancing my passion for dance and modeling with a full-time career in accounting and finance has been anything but predictable. There were times when I wondered if I was biting off more than I could chew. But those risks—whether it was saying “yes” to a new project, chasing an opportunity that seemed just out of reach, or investing time in something uncertain—always taught me something valuable. Read more>>

Nancy Gao | Graphic Designer

I believe risk is an inherent part of life. From an early age, we learn how to take risks. For example, the first time we learn to walk or ride a bike feels risky because it’s unfamiliar—we lack the experience and are uncertain of the outcome. As we grow older, risks evolve. Choosing a career that may not align with the expectations of family or society can feel daunting. However, since risks are unavoidable, why not learn to accept and embrace them? Read more>>

Chrissy Stuart | Jungian Coach | Depth Psychology Practitioner | Creative Facilitator | Holographer/Artist

To take a risk is to encounter the unknown. I see risk as a necessary tool for psychological expansion and creative growth. From a psychological perspective, the unknown is the realm of the unconscious — the wellspring of our creativity. Creativity requires a relationship with the unknown and therefore involves risk-taking. When we consciously engage with the unknown and the unconscious, we begin to move from an ambiguous, stagnant place of uncertainty, doubt, and fear into a deeper state of creative flow, authenticity, self-knowing, wholeness, and empowerment. True creativity emerges when we merge the conscious, known parts of ourselves with the unconscious, hidden aspects of self. Radical transformation and creative breakthroughs occur in this experience of integrating our ego-consciousness with the unconscious psyche. Read more>>

Danchi (diamanta) Zhao | Production Designer

For me, choosing to study art was already a huge risk—one that felt even bigger growing up in China. In my family, art was encouraged, but only as a hobby, a way to cultivate taste or build character. It was never seen as a viable career. Like many parents, mine hoped I’d choose a more stable path. They sent me to piano lessons and ballet classes to refine me, not define me. The idea of pursuing filmmaking was far outside their expectations—and, to be honest, it was outside of mine at first, too. Read more>>

Xinzhen April Yang | Film Editor & Director

The idea of taking risks has been an actual defining element in my career, always pushing me to confront uncertainties and to take on challenges that define not only my work but also make me grow as a filmmaker. One of the riskiest projects in my career during my lastest production: Broken Finger, was dealing with East Asian identity, societal expectations, and complexities within LGBTQ+ relationships. It wasn’t just about telling a bold story; rather, it was a tightrope act: treading creative integrity in association with real-world constraints. Read more>>

Anton Usikov | Director of photography

I come from a city called Luhansk in eastern Ukraine. I don’t know if it was the same for everyone, but I spent most of my days daydreaming about living abroad and working on exciting things. There was nobody and nothing around me that would even suggest that a creative career is something I could do. Looking back now, my unwillingness to accept reality as it was fueled my motivation to learn English, and leave. Read more>>

Cody Runkle | Model & Actor

You will always miss the shots you don’t take. I took a huge risk moving to California from Connecticut, especially during a pandemic which I will say driving across the country when no one was on the road was amazing and an experience I would have never had if I didn’t take the risk. I will say it allowed me to have a fairly smooth transition to this place that’s so different from what I’ve known my entire life. I was 21 when I moved here and have had 4 amazing years with so many life lessons, explorations, and experiences that have formed me into the person and artist I am today. Read more>>

Estevan Ramos | Stylist/ Fashion designer/ Tailor/ Illustrator

I’ve been a freelancer since 1993 after my last full-time position was dissolved from the company downsizing and ultimately closing. Self-employment for over 30 years is a Big Risk in itself. It really isn’t for everyone. You really have to be very self-disciplined, motivated, patient and have the drive on a daily basis. I’ve always been a non-conventional type of employee since my first real job as a stock boy in shoe retail back in the day. Read more>>

Trella | Singer & Songwriter

When I started my career as an artist, I had no idea that I was “taking risks.” I was 23 years old and I was dead set on making music that pushed the envelope and made people feel seen and understood. I was willing to do anything it took to make the music in my head come to life and to do it well. I strived for excellence, and naturally every dollar that I earned and wasn’t spending on my basic needs, I invested back into the music. I had zero savings, no family money, and worked as a songwriter and a preschool teacher. I did not consciously make this decision at the time, but looking back I basically gambled all of my money away on a dream that felt like the truest thing to me. Now that I’m years into my career, I consciously make measured risks alongside my team.  Read more>>

Albert Salinas | Trinity University – Tiger TV – Operation Manager

Taking risks has played a pivotal role in shaping both my life and career. I’ve often made decisions that might seem risky to others, but they’ve been crucial in pushing me toward my goals. During the COVID-19 pandemic, while many international students either chose to return home or take a gap year, I made the firm decision to stay in the United States. This allowed me to observe and experience the unique challenges faced by international students, particularly Asian students, who were not only grappling with the pandemic but also with heightened discrimination. Feeling compelled to address these issues, I decided to create a documentary capturing the experiences of international students during the pandemic. Read more>>

Amy Keoroghlian | Huge foodie, restaurant critic, Content Creator on Instagram and Tik Tok

I feel like my entire life has been one big risk taking journey. If you don’t take risks in life, you’ll just get stuck and you won’t move forward or move on. I’m not the type of person to wait and see what happens if someone else tries something new and different. I’m usually the one that will take the risk in trying new things, you can say it has been my entire life’s motto. I think my husband has played a huge role in that as well because we’ve always taken risks together and so far we’re happy with where our life has gone not saying life has been perfect and 100% but we get through things together. If you don’t take those risks, you’re just missing out on what could be. Read more>> 

Cat Charles | Artist & Director

I believe that taking risks is the key to a vibrant and fulfilling life. I have met the most incredible people and found the most beautiful community here in Los Angeles, all because I pushed myself outside of my comfort zone. I take risks both inside and outside of my work. I often deal with difficult subject matter, and I don’t know what the general reaction will be. Some people absolutely hate my work, but some people don’t. Either way, I hold a lot of value in the information I receive from viewers, due to the artistic risks I take. Read more>>