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.

Simene’ Walden | Educator, Speaker, Best Selling Author, Book Coach, Publisher

The first risk I ever took was believing what God said about me. I had messed up so much and was not qualified by the standard of people to do anything I was about to embark on, the things I am embarking on, and the things I will ever embark on. Entrepreneur can be defined as a person who organizes and operates a business or businesses, taking on greater than normal financial risks in order to do so. If you are not willing to take financial risk in your business, you will not last long. I have taken many financial risks to learn, grow, and scale my business, my character, and my career. Read more>>

Joey Aich | Musician

Risks are everything for me. I’m the type of person who thrives when I’m faced with uncertainty. It brings everything out of me, which in some instances things I didn’t know I had myself. I truly believe in the trial and error method and failures or losses should be treated as lessons or teaching moments. To me, risks allow me/us to try new things or live outside of our comfort zone and expose us to those teaching moments. My biggest fear is 15/20 years from now, I think “damn, I really should have took a chance and did that,” or realizing a fear of mine held me back from progression. On top of that, I get bored when I win too much, or if something doesn’t challenge me. The thrill of a good “what if” excites me and ultimately makes me better. Read more>>

WeiWei Ding | Recording Artist and Analytics Engineer

I am pretty risk averse but I also believe in taking calculated risks. I took a couple years off of my tech career to pursue music and that was probably the biggest risk I’ve taken in my life. I hedged my risk by find sources of income that were more flexible. I am still making music but have found my way back to technology and am building two careers alongside eachother. I think whenever you take a risk, you have to hedge it. Read more>>

Angela Lark | Licensed Esthetcian/Executive Educator, Alexandria Professional Body Sugaring/ Owner- The Sweetest Skin Company

“…Courage is fear that has said it prayers.” ~ Karle Wilson Baker

I think risk is having both faith in myself and faith in the possibility of the best possible outcome of whatever it is I’m willing to lose. A very wise woman used to tell me, “set the goal, do the footwork and stay out of the results”. It was a risk in 2013 when I was pretty newly separated from my then husband and working for myself when I decided that I was going to fulfill a lifelong dream of going to Africa and hiking Mount Kilimanjaro. The risky part for me was not fear of traveling or falling off the side of a mountain and never to be seen again because I had never backpacked before. It was getting hurt and not being able to follow through with the goal. Read more>>

Kristin Nobles | CEO B Noble Media Group, Artist and Advocate

As a CEO of a media company risk taking has played a HUGE role in my life and career. I think many people calculate risk in terms of the capital lost or gained or the overall “opportunity cost”. I think that some of the least profitable risks I have taken have given me the greatest pay offs, as they taught me the best lessons and gave me priceless experience. I took my first big risk in business at the age of 24 . Passionate about independent broadcast rights I packed my bags and headed to Nashville to start my first internet broadcast company as a single mom. My family and friends thought the internet was a hoax and begged me to get a real job. I went anyway and that company was not a multi-billion dollar exit, but it was my bootcamp. Read more>>

Alexandra Talavera Méndez | Writer & Filmmaker

I’ve always been a little impulsive, kind of like jump first think later type of person, so for me taking risks sometimes came without even realizing I was doing it. When it came to my career though, that was a decision I had to think thoroughly. For the longest time I wanted to be a doctor, that was what I prepared for in high school but towards the end of senior year I had doubts. I got through one semester of med school and I decided to quit, I decided that I’d rather write a show about doctors than be a doctor myself and that was the first calculated risk I took on my future. I knew exactly what I was getting into with medicine, but with film, I was in the dark. Read more>>

Marlys Regina | Wellness, Beauty, & Lifestyle Monetizer

I think that normal is boring. I love when people are be unapologetically FULLY themselves, and that comes with risk. After studying neuroscience on the track to get my MPH in Public Health, I took a risk and deferred my acceptance to George Washington University to launch my wellness business online. Back then influencer wasn’t really a word yet in the way it is today. Most people thought I was crazy, that I would get into referring my favorite wellness products online for a way to diversify my income. But taking that risk, and believing in myself, moving cross country from Pittsburgh, PA to Los Angeles knowing only 2 people (2 of my greatest mentors) was a RISK. It wasn’t safe, I had no where to live, to call my own. I think of risk as necessary process in growth. Feeling the fear and doing it anyway. I could go on and on about this. Read more>>

Jeff Consoletti | Founder, Principal & CEO

I’m a firm believer that taking chances can only enhance and help further guide one’s path to success. This certainly doesn’t mean jumping at anything too hastily, but really thinking strategically and identifying opportunities that can allow both myself and my company to flourish. This has been my approach with JJLA. We are seasoned event professionals and overtime, have developed into a robust, full-service agency. I look at the challenges our clients throw at us as learning opportunities. I tend not to say “no” and instead beg our team to figure out “how” when we are challenged with something that is new or potentially out of our traditional scope. Anytime that we’ve tried something new, and taken a risk, we’ve succeeded. Read more>>

Lacy Fisher | Actress|Writer|Acting Teacher

Risk is at the heart of every great story. As an artist in the world of storytelling risk is a requirement if one wishes to express themselves with authenticity. However risk is not easy because it asks of us to abandon the familiar, surrender relentlessly to our human need to know, and just ride the waves of uncertainty. I have learned over the years in my development as an actress, and working within the artistic field, that in order to really take on the challenge of being vulnerable in a very public way, mission and purpose are vital. In my many years of mentorship with Diana Castle and her brilliant teaching, that empathy is at the heart of the art of acting; it is through the empathic embrace of telling stories that allows for risk taking in the face of every dragon. Read more>>

Adrian Quihuis | Comedic Innovator & Life Artist & Adrian Entertainment Streaming Network

Risk Taking? What’s that? I view Risk, like Magic. If you know the art and how to do magic, tricks, and illusions then you can get away with a lot. People see the final product and they are trying to wrap their brains around it on how did they do that, or how did you think that? I love playing the risk card, that’s the only cards I use. Pushing the boundaries of what can be done or what is imaginable. I think risk plays a big part of being innovate, bold and standing out. Risk has a played a big part of my life and career. I feel like it’s going to be there my whole life and career. Read more>>

Kelli Gasaway | Salon Owner, Hairstylist & Educator

When I think about risks, I tend not to focus on the uncertainty of the outcome but instead view them as an opportunity for new experiences that will help me become a better, more well rounded person. Every risk comes with the potential to work out for us or end in failure, but 100% of the risks we take provide the necessary tools to overcome our fears & develop character, courage, confidence, resilience & persistence. In my opinion, developing these traits are some of the greatest gifts life has to offer. Taking risks means we don’t always win but guaranteed we will always gain new perspectives that we can learn & grown from. Read more>>

Samantha Fall (Harris) | Multiple Business Owner & Author

Risks abound in our daily lives; some even occur without our own awareness. However, some choices and risks we are presented with may carry more weight than others. The decision on “what to do with my life” may feel destined for many, and for other individuals it may feel like a constantly changing path with an unknown outcome; a dead end here, a sharp bend there, and a rocky trail up the mountainside further ahead. Being entrepreneurs and creatives, I feel many of our minds may drift to fruitful ideas, but placing those concepts into effective action can be a struggle…and a risk. Especially if it is your own livelihood on the line. Read more>>

Sam Bartlett | Musician and artist

I think much of my career has been like walking down the knife edge of a mountain trail. I just try to focus on the one foot wide path that I need to step on, and NOT on the thousand foot drop on either side. Now that I’ve survived to the age of 59, still doing music and art, the fall worries me a lot less. Of course now I feel my mortality more than ever, the shortness of our days, and I am happy that I have taken such a risky path. My father was a tenured professor of soil science at the University of Vermont. I tried really hard, but was a terrible student and became obsessed at the age of 14 with playing the banjo and drawing. Read more>>

Markel Badallo Latorre | Audio Engineer & Composer

Deciding to follow an unorthodox career like music or art is always a risk, but I would say that trying to create a business on an industry that is still under development and constant change, like the video game industry, is even more adventurous. Sometimes it feels like walking through an unexplored jungle. However, I couldn’t be happier about taking this path. It might be risky and scary, but it is better than regretting not doing it, or having a job that you hate and doesn’t make you grow. I also took a huge risk coming to the America, being the first member of my family emigrating, but it was worth it, so I think you have to be brave and follow your dreams. Read more>>

Jeta Stephens AKA “My Banker Jets” | Finance Storyteller & Educator

Baybeeee. I’ve been playing a game of leap (of faith) frog since I quit my job as a banker two years ago. It started with handing in my resignation without having another job lined up. Then months later, relocating to California from Pennsylvania, still with no job prospects in sight. It’s been a continuum of risk-taking ever since! With each leap, I’ve been shocked by, not only my ability to land on solid ground, but my ability to fly. Every day I see the immeasurable benefits of partnering with God on one’s journey to success. Read more>>

Michael Armstrong | Singer/Songwriter & Producer

With a lot of creative professions, the biggest risk you run into is your own anxiety and fear of failure. But when you stop to asses the potential outcomes of those failures, you realize you’re not risking much at all. I personally come back to the mantra that the process of making the art is the unwavering reward for putting yourself out there. Read more>>

Jeremy Sample | Stunt Coordinator

Risk is defined as a situation involving exposure to danger. I left a corporate career to pursue a new path in stunts. The nature of my profession exposes me and others to situations that would make most people uncomfortable. We take calculated risks to create the action sequences people enjoy in their favorite films. Read more>>

Hilary Bilbrey | Human Capital Consultant, Life Coach and Podcast Cohost

If you aren’t a little afraid, you are living in your comfort zone and now growth can happen there. Healthy risk-taking is one of the primary ways that I push myself and my clients to become better versions of ourselves. Healthy means we are not knowingly putting ourselves in a catastrophic situation or one that could cause us harm, physically or emotionally. When we take a risk and find our way through to the other side, we come out more confident, more trusting of ourselves and more empowered to take on the next challenge life will inevitably throw at us. One of my favorite “risks” was when I hiked the Grand Canyon Rim to Rim. Read more>>

AdaPia d’Errico | Investor, Entrepreneur & Executive Advisor

The way I have related to risk has changed over the course of my life. I used to think about risk as something to avoid because it could come with a bad consequence. In my mind, I could never be the person to have the ‘big reward’ that is often related with the positive payout of risk. Even in investing, we say that higher risk investments come with the higher ‘reward’ of higher returns. However, I now think about risk as an opportunity to question how to achieve something. It’s an opportunity to pause and deeply consider possible outcomes, as well as areas where I might be holding myself back from taking action out of unexamined discomfort or fear. The truth is, I’ve taken a lot of risks in my life, and some have not worked out well, and others have been incredibly positive. Read more>>

Courtney Lin | VO Artist, Actor, Choreographer

It’s funny because I’ve always been a pretty risk-adverse person. You won’t catch me playing the lottery willingly, trading a ton of stock, or gambling. However, in pursuing the arts as a career I have spent the last 5 years betting intensely on myself, knowing that with the way the industry is, you could be the most talented person in the world, but if that right role doesn’t come at exactly the right time, it’s possible to not be able to make a full career out of it. Yet, in the last year, somehow, by a combination of a miracle and an incredible amount of sweat, time, money, and effort, I’ve been able to transition to artist full-time. Taking this risk has been one of the most challenging and scary things I’ve ever done, and I am so grateful for it. There aren’t a lot of things I would bet on, but I know I can always count on myself. Read more>>

Nathan Christ | Director, Writer, & Producer

Much of the stories I’ve sought out have been risky, and have taken me around the world. Historically my projects involve musicians and music cities, from Bamako, Mali, to Sao Paolo, Brazil. Making films about music communities requires a lot of trust. I’ve had to put myself out on a limb on many occasions while chasing down a story, and sometimes that can go south, or not yield the results I want. This can lead to a lot of heartache but, when you get it right, it’s so gratifying. Read more>>

Brian Hettler | Artist. Creative Director. Drag Nun. Lover of Life.

My favorite story to tell people is how I went from being a broke part time drag queen/part time chef living in a 7’x7′ room in a commune in El Sereno to working as a creative director at one of the best ad agencies in America. I truly fell ass backwards into doing what I do for a living, and it’s all a byproduct of saying yes and being my authentic self. You might ask, how DID you do that? And it’s all about saying YES to opportunities even if you’ve never done things before. Ten years ago, when I moved to LA, I came to be an artist. Big dreams, no money, and no job prospects. Read more>>

Bryanna Jacobs | Makeup artist and Model

When you’re in the freelance industry, you take risks a lot, especially in the the beginning of your career. For me, the risk I took was moving across the country at 18 by myself with no connections or friends to become a makeup artist. It definitely hasn’t been easy but it’s a risk I’m willing to take. Read more>>

Derek Robinson | Cinematographer

Risk is inherently part of every experience, relationship, and worthwhile pursuit we engage in, and the entertainment industry can be an intimidating, confusing, and frustrating place to navigate risk and reward. If you approach a creative project from practical perspective, working based off of previous experiences and leaning into things that pleased everyone in the past, you may miss out on an opportunity to develop new skills and push your work into more interesting areas. On the flip-side, you can lean too far away from your instincts and miss the mark because you wanted to experiment when it wasn’t best for the material. Read more>>

Yolanda Mariah Morgan | Screenwriter & Director

When I think of risk taking, I think of faith. Concurrently, I also think of fear. Risk taking is an action of stepping out of one’s comfort zone in the hope of a desired result. Sounds scary right? One of the scariest parts of risk taking is that there is no guarantee you will have a positive outcome. The average person experiences a multitude of emotions before they even embark on their risk taking journey. One of those emotions is fear. That negative feeling of fear can often stifle a person from ever stepping out of her comfort zone. Bishop T.D. Jakes once said, “Faith and fear cannot occupy the same space at the same time.” Throughout my life and blossoming career, I have learned that this quote holds true. As a young filmmaker, one of the most important lessons I have learned is that taking risks is vital to my personal growth. Read more>>

Larry Ulrich | Landscape Photographer. larryulrich.com

In the late 60’s I was in the Air Force Reserves and was assigned to a radar shop at Travis Air Force Base in California. The four other guys I worked with were all fanatically into photography. Once a month they would bring their most recent images to the shop to share and to critique their work. At that time I had no interest in photography but I joined the fun of these critiques. One of the guys taught photography at a local junior college. and after a year of joining the discussions he pulled me aside and told me that I had a very keen eye for composition and I should consider taking up the craft. Read more>>

Antonio King | Entertainer & Teaching Artist

Risk taking is everything. If I didn’t take risks, I’d still be in Indianapolis, Indiana surrounded by corn. (I do love and miss Naptown though.) It reminds me of one of my favorite quotes by Emmy nominated actress Neicy Nash, “You can’t be on tv by sitting at home watching it everyday”. You have to get up and take those risks. But I’m also aware of how blessed I am. I was raised with so much love and support, so I was prepared to take risks because I knew I had a safety net below me. Read more>>

Yainer Ariza | Professional Dancer & Choreographer

Taking risks is one of the most important tools to utilize in a creative career like dance. If we don’t take risks I don’t believe we can jump to higher levels and we wouldn’t find out all that we are capable of. Risk has been principal to my career advancement. You take risks but then need to work very hard so that it turns out well. Read more>>

Kwan Leung Ling | Composer/Performer

I started practicing Suona (a Chinese wind instrument) when I was ten years old, focusing on traditional Chinese music in Hong Kong. After ten years of traditional Chinese musical training, I decided to embark on my new music journey in the United States, starting my Western musical training. This has put me at risk of language barriers — Communicational, musical, and cultural . I started my first semester in the U.S. with a weird class schedule – a 7:30 a.m. class and an evening class. Read more>>

Michèle Jochem Yunus | Fashion Designer

Looking back, risk has always played a big part in my personal life as well as in my career, although it didn’t feel like a risk to me at that time. Moving from Germany to Los Angeles seemed like a big risk to many, but I actually thought things through for years before taking the leap. It really depends on the person and what they define as a ‘risk’. For me, I always try to take calculated risks. I try to listen to my heart first before thinking it through and making realistic plans. It’s definitely a balance between emotions and pragmatism. Read more>>

Brennan Manuel | Designer

I think risk is a natural part of our lives, but it’s something that we are taught as a society to avoid as much as possible. The avoidance of risk is not an ideology that I necessarily agree with. We allow other societal norms to be classified as less risky or not risky at all, while categorizing others as extremely risky. For example, having kids can be just as risky as investing in the stock market. The former statement would get labeled as apocryphal and the latter would be lauded as truth. Then you have to think about where the prevailing narrative of risky societal behavior comes from. I believe it’s a top-down directive to keep most people from having a relationship with risk, understanding risk, and hedging risk. Having a relationship with risk is how you build wealth and protect yourself and your posterity. Read more>>

Kirsten Potenza | CEO + Founder of POUND – Rockout. Workout.

I think by nature being an entrepreneur is about going all in. I started POUND when I was 24, in an industry that was-at the time-predominantly male and centered around body image and weight loss. We were trying to break the mold and whether that was eliminating body-centric language from how we spoke or building an instructor training model instead of owned studios, it all felt risky. But those experiences and I guess who I was, really helped shaped the ethos of our brand. Read more>>

Laura Rebecca | Artist/Writer/Teacher

Risk taking is something way out of my comfort zone, which is one reason I’ve pushed myself to lean into it. I’ve changed careers several times in my life–from teaching high school, filmmaking, fitness/wellness, marketing/advertising–and moved across the country three times. All of it was uncomfortable, but essential to my growth as a person and artist. If you’re someone who is particularly sensitive to the voices and opinions of others, ask yourself this: how does it feel when you get feedback and advice (solicited or not): does it feel like it lands? Does it seem accurate? Does it identify with something you already know about yourself, even if that’s uncomfortable to acknowledge? In other words, listen to YOURSELF. Read more>>

KAREN MIRANDA | Entrepreneur & Podcaster

Risk taking can be very scary, but my mantra is, if you want to grow, you have to go for it! Many times, going for it, however, involves taking risks. The plain definition of risk states: a situation involving exposure to danger or exposing you or someone or something to some type of danger, harm or loss. Of course thinking of a risk in that manner, human nature will tell us to avoid danger at all costs, yet my personal experiences have shown me that risk taking is a must in order to grow to new levels, to open doors you didn’t know existed, to expose yourself to new things, new experiences, new opportunities, new adventures, and new friendships. Read more>>

Cassandra Due | Actress & Filmmaker

There is no chance without risk. Whatever decision you make, there will always be consequences, whether good or bad. As an actress, people tend to say that some choices are “risky” when it comes to choosing how to perform a certain role. Some people even say that an acting career in itself is “risky”. But is staying on the “safe” side of things not a risk as well? I know for a fact that if I didn’t pursue what I’ve been wanting to do since the age of 6, I would have regretted it. I would not have met the people I care for the most, I would not have had the opportunities I’ve gotten and continue to be presented with, and most importantly, I don’t think I would have been happy as a whole – there would have forever been this silent guilt towards myself for not even trying, and therefore, succeeding. Read more>>

Allon Avgi | Real Estate Entrepreneur

I love taking risks. When I was broke and had nothing to lose, risking everything I had was hard because the loans I was accessing weren’t as calculated as I would’ve liked. Today, as I keep building my portfolio and money comes in, I see it all as more collateral to leverage into bigger more calculated risks. Without constant risk taking, I wouldn’t have close to what I have today. Read more>>

Tiffany Caldas | Racial Equity Consultant

Risk taking is usually defined as the exposure to danger or harm, or the possibility of experiencing loss because of exposing oneself. When I decided to move to Miami to college, I was told I was at risk of losing sight of my education, and becoming a conceited and selfish person. When I decided to leave my full-time job and to instead work for myself, I was told that creating my own company and working for myself was a risk, and asked if it was something I could really afford to do. Read more>>