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.

Enrique Garcia | Actor

I was very comfortable with my life in Madrid, Spain back in 2022. I was 24 years old, had a pretty good job with very promising projections, had my family, friends and a healthy life balance but quite simply, something was missing. I was living the life I thought I was supposed to live, not the life I was meant to live.  Read more>>

Kimberly Quigley | Distributor, Executive Producer

I think anyone who wants to try something new and venture into a field with original thoughts is intrinsically taking a risk. The people who are leading in the entertainment industry all have that in common. I have heard many times the terrible odds of success, numbers and figures thrown at me and I always dismissed that as a wrong way to evaluate because it is missing the factor as to WHY those few did succeed.  Read more>>

Roper Williams | Producer

In order to not feel bored to death i need to be taking risks. The risks don’t always have to be parachuting out of an airplane, it can be something smaller like not scanning an item at self checkout. When it comes to producing music i feel the same way.  Read more>>

Ashley Bourbeau | Life Coach

There is a one thousand percent chance that if you don’t put yourself out there and take risks, you won’t make progress. Sure, failure can be scary, but so is sitting around later in life wishing you had taken more chances. You can take pretty big risks if you have confidence, a solid mindset and awareness on your side. Read more>>

Rachel Om | Potter & Transportation Planner

I was drawn to this question because this question made me realize I’ve never really contemplated if I’m a risk-averse or risk …positive(?) person. I hesitate to use the term “risky” or “brave” as the opposite of being risk-averse because I don’t think those are necessarily the two options when thinking about life and career decisions.  Read more>>

Garrett Parrish | Art and Creative Director

“Greatness favors the risk-takers” is what I’ve always lived by. To me, if you’re not uncomfortable in your career and experiencing moments where you’re unprepared and out-of-your-league, then you aren’t pushing yourself enough. Read more>>

Seth Cunningham | Filmmaker

If there’s no risk, there’s no business. Every part of my industry is risk whether it’s working as a young director, moving to a completely foreign place, or chasing a industry that’s future looks more uncertain and unstable day by day, it’s a risky time to work in film.  Read more>>

Derek Goh | Actor

I believe that taking a risk on yourself, for yourself, defines what you are doing and the vision you have for where you’re going. If you don’t stick your neck out and try for something you don’t have the answers to right away, you spend your time just doing what other people say and letting someone else steer your career. Read more>>

Serene Zloof | Actor Writer Performer Producer

When people ask me if I bungee jump or skydive, I say “Performing is my Extreme Sport. I get on stage fearing the worst kind of death – the public one.” Performing is about wearing your heart on your sleeve, no matter how the crowd responds. Read more>>

Meghan Samson | Ceramic Artist and Educator

I think the first BIG creative risk I ever made was deciding to study art in college! This was the beginning of my relationship with risk, which has taught me so much how to listen to my intuition and fight the urge to keep things safe. A healthy relationship with risk is a big part of being an artist.  Read more>>

Nate Burrows | Bar Owner & Stand up comic

I think we all are afraid of life to a certain degree, our whole culture is catered to the idea of being comfortable – and I think the real fun in life is seeing what life is like out of whatever subjective blanket we’ve tucked ourselves away in. That being said I’m not fucking Bear Gryls, I don’t mean this in the sense that I’m looking for cliffs to hang glide off of or any shit like that. Read more>>

Anthony Friedkin | Fine Art Photographer

I think all great artists challenge themselves to create bodies of work that involve risk taking. Whether it’s on a deeply personal level, exploring an emotion which is complicated and vulnerable to their soul, or a spiritual question that is mystical and perplexing, or exploring feelings about death, sex, religion or politics…  Read more>>

Joan Young | author, speaker, adventurer

I am pretty sure that humans were designed to require at least some level of risk in their lives to be happy and feel fulfilled. That doesn’t mean we all have to love extreme sports or enjoy dangerous adventures, but I do think there is some threshold of activity that causes excitement to participate and generates a sense of accomplishment when the task or event is successfully completed. Read more>>

Tommy Anderson | Author, Actor, Screenwriter, Producer, Podcast Host

My entire adult life has been that of taking risks and completing tasks under stress and even danger. This started at 18 and going into the military and at that age I had to do tasks both physically and mentally that I never had even imagined doing. It taught me that my only limitations in life were my own that I would put on myself. Read more>>

Peach Rosemary | Award Winning Director

I love taking risks, especially in film and the art behind it. My projects are becoming that right now. I think for those who have a weird gut feeling like they should, do it, the worst thing is the worst thing you thought of, and that’s the learning curve. Read more>>

Shalyn Delhaes | Producer & Filmmaker

The biggest risk I ever took was at 18, just after graduating high school in Germany. It was a pivotal moment when my dad received a job offer in the U.S., presenting me with a daunting decision: to leave my home country behind and venture into the unknown. Read more>> 

David Cerquetti | Composer & Songwriter

Taking risks is everything. I believe that in any artistic field if you don’t risk something you will never achieve success. Well, then you also have to know what success means, it is so different for each of us what this word means. I believe that anyone who wants to pursue this kind of career must have a predisposition to risk as well as to make sacrifices. Read more>>

Isabela Gaya | Actress & Performer

Moving from Mexico to New York City was one of the biggest risks I’ve ever taken, both personally and professionally. It meant leaving behind familiarity and comfort to pursue my dreams in a new and daunting environment. However, it was also a risk filled with promise and opportunity. Read more>>

Jack Brady and Matthew Zeko | Mack Imagine

We both are risk averse people in general, so taking risks is something that both of us understand that we need to continue to work on, considering how important it is within the music industry as a whole. We both have already taken the risk of pursuing a career in music together and we know risks can pay great dividends for people in entertainment and music. Read more>>

Meredith Mansfield | YouTuber

Oof. I love this question. My first major risk in life was taking a gap year in between high school and college — and going through that risk, at such a formative age, transformed the way that I thought about “risk” in general. Read more>>

Ibby Day | Designer & Founder of ATC

Risk-taking, or perhaps risk tolerance, is a quality I’ve thought about to a great extent lately. In January, I left my marketing job with nothing lined up because it was a poor fit. While it wasn’t a completely thoughtless decision, I think it would surprise most people to know that it was an easy decision for me in the grand scheme of things. Read more>>

Lauren Corugedo | Head of Marketing, Chef Merito

Taking risks for Chef Merito has led to some of the company’s greatest achievements like our first-ever and now ongoing partnership with the Los Angeles Dodgers. As a small brand, the risk with partnering with such a large entity was the investment that we had to make when batting up against some of the other major players in the space. Read more>>

Robert Wagner | Stand up comedian

Risk is vital to life and having a strong career. Risk helps build confidence in whatever you do in life. Without it I wouldn’t have fallen in love and I wouldn’t be pursuing Stand up comedy or writing. Risk helps you connect with things and people you love and gives you that thick skin for failure.  Read more>>

Suzann Christine | National Recording Artist & CEO

Taking Risks activated my faith and allowed me to receive opportunities that I know for sure I would not have ever had, if I had not taken the risks. I’ll never forget when I first quit my full time job to follow my dreams of becoming a music artist, I submitted my song “Closed Casket” into a contest. Read more>>

Joey Gholam | Actor

Risk taking has played a major role in my life and career, I believe taking risks is important in life. It plays a major part in success. Growing up I’ve always loved acting and entertaining people. Watching movies I’d imagine doing the same thing too. One day, I went to my first audition and I immediately wanted to pursue acting professionally after the audition. Read more>>

Marina Ogalla | Actor and Singer/Songwritter

I believe that taking risks is a very important part of a successful career, mostly a creative one. If we avoided taking risks we wouldn’t do anything in life. Putting out a song is risky, making a short film and submitting it to places is risky, and being on stage is risky. Read more>>

Bea Qian | Cinematic Artist & Narrative Designer

I’ve always been a risk-taker throughout my creative journey. I’ve been making films since my middle school years, it has always been my favorite way of creating art and expressing my thoughts. But in the last year of high school, after a 6-year longing to attend a film school, I switched my passion to animation. Read more>>

MARISA | Singer & Songwriter

I think as an artist it’s really important to take risks, especially in the music industry. I personally took a huge risk when I started making music. In 2017 when I moved to LA, I had just finished my theatre degree and was heavily pursuing acting. I actually went on an audition that required me to sing and dance and after that I just completely switched directions and focused on building a music career as a recording artist. Read more>>

Lorenzo Bellini | Pianist, Composer, Educator

The attitude of risk taking has been one of the key elements of my career. During my development as a musician, I found out that I grew the most when I’ve been able to overcome the fear of failure or of rejection, the fear of a bad mark and, in a way, the fear of being judged by others. Read more>>

Marsha Rosales | Tattoo Artist + Interdisciplinary Designer

I think risk became a large factor in my life and career as early as deciding to pursue an art degree, the lowest of all the humanities. No one is hyped for you when you tell them you’re an art major. No one is egging you on or trying to persuade you to study art the way they do for medicine or law. Read more>>

Stephanie Roussinos | Videographer, Editor, DJ, Artist Management, Social Media Manager

Take risks! It’s the scariest thing in the world to make a jump into the unknown, but if I stayed where I was I’d still be working a 9-5 mundane job wondering, “what if”? After years of following through with university and landing that classic job that pays salary and benefits, I found myself to be extremely unhappy. Read more>>

Linda Graveline | Owner, Eleven Interiors Home Staging

Being an entrepreneur takes a lot of courage, especially when you don’t come from money or have access to additional funds to fall back on as it grows. I already had a successful Reiki practice, so I slowly but surely tipped the scales from that to staging over several years. Read more>>

Deanna Fainelli | Travel-Inspired Painter

Risk taking is important for success in any career but it is an especially important factor when creating art. As an artist, it is important to overcome the fear of failure to keep creating new and innovative work. Read more>>

Christopher Zapata | Photographer & Film-maker

If you want to lead a life that isn’t stagnant, take risks. It’s a pivotal part of growth and decision making. When you look ahead to the future and see a better one because of a risk/decision made. I say, do it. At the end of end of the day, it comes down to living in your authentic truth. Read more>>

Dana Mackin | Actor & Producer

At the end of the day, after considering grit, strategy, or likeability, I always lead with integrity – and as a creative I really feel that integrity and authenticity are synonymous. In the entertainment industry, there’s this overwhelming sentiment of “fake it until you make it,” but when you’re on camera or onstage, that just doesn’t ring true; people won’t connect, they won’t resonate with it, and the project won’t succeed.

Neda + Zabie Studio MUKA | Architecture + Interior Design Office

Over the past few years we’ve honestly become increasingly more comfortable with risk and risk taking. The reality is that the risk of failing or losing out on something can often trick the mind and can refrain you from taking steps that allow for personal and professional growth. In business, especially when starting a new business, everything is a risk. Read more>>

Samantha Reckmeyer | Multidisciplinary Designer

I believe taking risks is essential for personal and professional growth. Remaining within our comfort zones stifles evolution. Every remarkable achievement stems from a willingness to take chances. When faced with decisions involving risk, I’m often reminded of the saying, “Nothing changes if nothing changes.” Hence, I advocate for embracing risks in both career and personal life as a pathway to self-improvement. Read more>>

Mac Cherny | Comedian and Playwright

I think about risk quite a bit because my entire artist career has been one! Being an artist is a risk to begin within. It’s unstable, subjective, and breeds insecurity. However, I am my best self when I am creating and performing so that’s why I do it.  Read more>>

Oscar Bautista | Musicians & Creative Producer

Risk has always been at the forefront of the projects and paths I take. Moving down an artistic route, regardless of the medium, I find myself balancing out what effort and resources go into a work versus the integrity I wish to maintain. Read more>>

Jerry Gureghian | Actor, Write, Producer

Diving into acting in my 50s was like deciding to jump, blindfolded off of the Cliffs of Insanity. The fear of failure was huge because, let’s face it, in the cutthroat world of business and even among friends, failing gets you sympathy at best. Read more>>

Nekeith | Actress, Model & Recording Artist

I think risk taking is vey crucial for anyones career, you definitely need to have a strategic plan. Taking risks has played a major component in my career because I believe in my art with my whole heart and I take risks to be bold and go against the society norms. Read more>>

Bryan “Ace” Torres | Actor & Model

I look at risk as opportunity. A lot of opportunities are presented when you takes risks. Along my journey I’ve had to make sacrifices which has been risky in itself. Without risk, there’s no opportunity. Read more>>