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.

Alex Weinstein | Artist

My mother never lets anything stand in the way of something she wants to discuss, understand or explore and will throw her intellectual curiosity at a topic without restraint. By comparison, my father is purposeful, academic and critically rigorous in his interests. As a team, they are so strong because of their complementary strengths. I mention them because I wonder if “risk” isn’t more easily observed by the person standing next to you than it is by your own view of things. I was a gregarious kid; physically confident, athletic. I wouldn’t think twice before hucking myself off of jungle gyms or sliding down handrails in preschool. Later, skateboarding literally consumed my life and skaters crash, a lot. I guess my sense of risk was very physical as a younger person and now it’s more philosophical and by that I mean that while I’m not skating much these days, I do look for projects with challenges and uncertainties that I want to learn from. Read more>>

Kim Guerra | Creator & Author

Risk requires courage and vulnerability. It also requires you to believe in the power of your dreams. It asks you to say yes to yourself and trust your wings. Risk has been a key factor in my life. I took a risk when I decided to start sharing my writing on my Instagram feed. “What if people think it’s stupid? Why would they care about what I have to say? Should I delete it?” I kept writing and sharing. The poems and affirmations I wrote turned into a book called Mariposa. The butterfly is the perfect example of a being who risks its entire being in order to gain wings and potentially fly. “Mariposa” became an Amazon bestseller. This was a year ago. I was a recent divorcee living and healing in Seattle. I packed up all my fear and belongings and went on my very first book tour. Another beautiful risk. There was no certainty. Nothing was guaranteed. I had no idea if people were going to show up. Could I actually go ahead and do this on my own? I did. And they did too. Read more>>

Laura Haug | Life Coach, Energy Healer & Yoga Instructor

Risk is an integral part of life. No matter what decision we make, some level of risk is at play. Risks can be opportunities, leaps of faith, and taking chances. I would consider myself a risk-taker. Taking chances feels like a large part of my adult life. Packing up my car and moving from Missouri to Los Angeles right after college was a significant risk. I had nothing lined up, and thankfully things began to fall into place quickly. When I realized working in entertainment had taken its toll, I quit a steady job to launch into being self-employed doing yoga, energy work & life coaching. When I ended a long-term relationship, four months away from our wedding that was a leap of faith. Moving back to Missouri and then to Portland were opportunities. Each decision brought with it grief, healing, a deeper understanding of who I am, a knowing of who my ride-or-die friends are, and experiencing life and its emotions to the fullest. Each risk had a cost associated with it. Read more>>

Tony Chang | Empowerer & Motivational Jeweler

Risk is a requirement for Success. What I mean is, if you don’t take risks in life, you will not go far. It is because I took risks that I failed and learned from my failures to become better and do better. Before I met my now Wife, I took risks by expressing my interest in the girls I liked. Although I got rejected, I did not stop. I kept going and BAM I met my now Wife and we have a wonderful Daughter. In business, I took risks and I lost money, but, I also received more money. I attracted people who took advantage of me and people who really helped me take myself and my business to the next level. If you don’t risk it, you will not get far in life. Read more>>

Matthew Jones | Founder, Director & Producer

Taking risks is necessary for growth. I put my business into high gear in 2020 – a risk in itself. My original plans for aspects of my business had to shift. At that point I became curious and tried new tactics by launching a fully remote podcast studio, and focusing on videos for essential and small businesses. I didn’t know if it would work. If I got a no – oh well, I tried. But taking a risk gives the opportunity for a yes – and when you land that yes it’s incredible and the first step to living in your purpose. Read more>>

Kendre Streeter | Musician & Producer

I believe that my entire career has been defined by taking risks. As an artist, it’s incredibly important to be authentic with yourself and with your audience. You take risks every day when you create music, experiment with different vocals and instruments, and then put it out for the world to see. It’s an incredibly thrilling and nerve wracking thing that never seems to get easier. Looking back at my career, I think the first big risk I took was when I launched my first gospel EP. It was the first time I recognized myself as an artist and it was important for me to pay homage to my upbringing and the church. My immediate family and friends loved the EP but my church was not happy with the music and felt that I was miscommunicating the teachings of the bible. It was the first time I really felt that my music was making an impact and starting good communication. I’m all about change so if it’s controversial, so be it. Read more>>

Suzanne Reilley | Life Transition Coach

As I reflect on this question, I can see that I generally take a risk when enough of the knowns are in place, and I’m willing to figure out the rest from there! I also consider my ability to catch myself, or heal if I fall. So, far my track record on either winning, or getting back up is solid! Because I’m committed to my own personal growth, I’ve gained a great deal of wisdom and resourcefulness from the challenging times. Taking risks in my career has also lent to really great opportunities I wasn’t expecting. A random idea from a past client led to me teaching at Rancho la Puerta, #1 International Destination Spa in Travel + Leisure’s 2020 World’s Best Awards. And a bit of curiosity led to me being featured in DailyCandy when they were at the top of their game. Basically, the risk of saying hello to people and not knowing the outcome has led to incredibly fun experiences. Read more>>

Sarah Flora | Homebrew Educator and Content Creator

I’m a pretty risk averse person. Starting Flora Brewing grew organically in the beginning and now I’m starting to take more risks in attempting to make it a full time job. Since I began the Instagram and Youtube channel I’ve been working a full time job on top of creating content and honestly, it’s rough sometimes. I’m about to take the big step of going part time at my job to pursue the content creating in a larger way and though it’s exciting it’s also really scary. Read more>>

Danielle Sabolch | Motion Designer

Risks are important. Risks sometimes lead to mistakes. Those mistakes are what help us develop new skills and ways of thinking. We grow from it. When it comes to my career I’ve always done things that made me uncomfortable. Taken risks. I’ve left the US a couple of times in pursuit of my creative development and to generally switch things up. Leaving everything I’d ever known behind, starting from scratch, not knowing if I’ll make it or not – it was incredibly challenging. But worth the risk. Working with different people from all over the world taught me so much. Try to make an effort to shake things up and take yourself out of your comfort zone. Read more>>

Mingjie Zhai | Journal-Artist, Entrepreneur, and Speaker

Risk is a critical ingredient to success, like yeast to making the bread rise while it’s being baked. I believe that everything worth doing takes risk. However, the caveat to this answer is that there is a fine line, a balance, a “calculated” risk taking that goes with decision making. Risk doesn’t mean to put yourself in dangerous situations or to go out of your way to suffer, but to lean into the parts that are still uncertain. It’s important to do your research, to listen for guidance, to seek mentorship, to do some market research, background checks, before making a choice. As for my personal story, I had chosen to leave a career in education to pursue a media company that fuses mental health because it was a pressing problem for me. I made a calculated risk: meaning the risk of staying the same (doing the same ole same ole way of treating my mental health via the pill, the therapy. Read more>>

Jamie Wozny | Reiki Master and Soul Empowerment Coach

I see risk taking more as a heart following. To the outside eye it can look crazy and wild and silly or illogical to some but to me “risk” when used in an intuitive way is a deeper pull of the soul. A jumping off point. A feeling of- I can’t do this anymore. Not from the level of the frantic brain but more from a level of deep knowing. A sense, a feeling, an image, a sound, a hunch that it’s time to do something bold. It doesn’t come from the level of our anatomy. It comes from the level of the soul. Those that follow the heart, the soul to me are seen as risk takers. There is more of a safety in it when we see it this way, like, “Oh, I’m just following my soul path. I’m safe there. I”ll be met there. There are safety nets from the Divine there.” Risk taking in this sense for me has been everything. Doing things in a non conventional way, following signs, readings, deeper inner guidance, dreams and the like has led me to new energy, expansion, healing. Read more>>

Joseph P. Gerges | Visual Artist

Risk. It’s the culprit of failure and the instigator of joy. Risk is my creative companion. It has accompanied me through the trials and tribulations of failure. Risk has greeted me in my fear of the “new” and has beckoned me to return to it time and again coaxing me onward. As I approach new challenges and push the limitations of my talents and expectations, risk spurns my ego. It slyly creeps into an idea, sneaking its way through from an earlier thought. It asks me to face it head on, to acknowledge the newness of an experience and embrace it. Risk is an opportunity to learn, to grow, to challenge myself and feel alive. I recall it egging me on at little league try-outs as a ten-year old, alone in a field of unknown faces. I remember it as a 16-year-old, new to painting, stepping into the discomfort of my first figure painting class. Read more>>

Keli Murphy | Multi Passionate Entrepreneur + Founder/Creator of Whimsy Sugar Scrubs

Risk is true surrender and trust mixed with adrenaline that fuels action. It is something you have to be willing to do in order to grow! RELAX, LET GO, AND ENJOY THE RIDE is a constant theme song in my life. While so many run away to avoid taking a risk or doing something risky, my whole life I have embraced it. From wishing my 1st airplane ride, at a very young age, would go upside down and jumping off roofs in my pre-teen years to a Professional career as a Dancer and Stuntwomen, you could say I am not afraid to take a risk! On my 30th birthday I went sky-diving and was waiting to feel nervous or afraid, instead I couldn’t run out of that plane fast enough! That was one of the best rides of my life. Risk is something that excites me. It reveals worlds I would have otherwise not discovered. You find your grit and strength when you take a risk and are able to tap into your true potential. Read more>>

Megan Hersch | Interior Designer & Entrepreneur

When I look back at my careers, taking risks has always been a part of my M.O. In the Film Business, I worked for the toughest players and then as a rising Studio Executive I took the biggest risk of all and decided to change careers and go back to school to be an Interior Designer! Needless to say, that was the best risk I’ve ever taken. In Design, I continuously look for new ways to solve a space and I am always drawn to techniques and compilation of pieces that have subtly never-been-done. Without taking risks, you cannot be innovative and without innovation, you are left sitting in the same row boat. 3 years ago I took another big risk and launched roomLift; a digital-first service that brings high end Interior Design service to customers easily, digitally and affordably. In a historically non-digital space, roomLift embarks on this road less taken to give everyone sitting at home an avenue to a well-designed space that they love. Read more>>

Jenny Hill | Small Business Owner & Work From Home Mom

I am not the type of person that would willingly go sky diving or climb a mountain or even ride that loopty-loop roller coaster at my local amusement park. However, as a business owner, I’ve found myself in risky situations. Acting on the very idea to start a business is in itself a risk. What if I fail? What if no one wants to use my service? What if I have to go back to waiting tables at the Bubba Gump Shrimp Company on the Santa Monica Pier? These are all questions that briefly crossed my mind when my business partner and I decided to establish our company. But one truth drowned out all of these doubts – I knew we had a GREAT idea. I knew that if we stuck to it and worked as hard as we could, we would succeed. My faith in the service that we could provide never wavered. Read more>>

Nicole Pittman | President

I think any business owner has felt the challenges of taking risks from time to time. It’s hard to know when you should take a risk or play it safe. I think in the end you really need to learn how to trust your gut. You may not always make the right decision but I believe going with your guy is the best option. If you analyze something for too long you become too fearful and usually don’t end up doing anything of value. When risk is involved, weigh the pros and cons and go with what feels right. Starting our own business from scratch was a huge risk but here we are 8 years later and am so glad that we did. It can be very stressful but it also allows for a lot of freedom. The risk was definitely worth it. Read more>>

Marilyn Espitia | Photographer/Creative Director/Artist/Health Coach

For me, I believe taking risks come from a place of fear. Fear of unknowing and uncertainty and not knowing the outcome of it. I’ve taken many risks in my personal life and career and it has definitely made me the person I have wanted to become and am still becoming. Once upon a time I made a decision to quit a secure job (knowing the risk that it may never become permanent) while pregnant for a better outcome to my future and my unborn child. I gained better/more experience and became well rounded in my job as well as gaining more access to opportunities and growing in my position, 2 years in I got a promotion and to this day it was still the best move I have ever made. I don’t have a job anymore, (company went under) but that’s okay. Im actually very happy spending more time with my kid and giving my brain and body some well rested time until I am ready to hop into the entertainment business again. Read more>>

Sergio Teran | Artist/Educator

Choosing to be an artist was a lifestyle risk especially coming from a working class background. That is, It’s financially uncertain, and although there may be intrinsic value it can seem really impractical. I understood that I might fail, but it was the only way to find myself on the other side of this career choice. Taking risks inside and outside of the studio is imperative, for an artist. The tricky part is getting up and dusting yourself off. If you want to learn and endure, learning is in the failures of ones choices. Read more>>

Thien A. Pham | Producer-Director

I see life as a continuum of risk. At any given time, everything we do carries a degree of risk. In the past, the word ‘risk’ invoked an automatic negative connotation, and I approached it from an opportunity cost perspective. When assessing risk, I used to make decisions based on what I considered the optimal choice at the moment — essentially, the choice that would reduce my exposure to risk as much as possible. Now, I no longer see risk as something ‘scary’ that teeters on the opposite end of the see-saw. Instead, I’ve shifted my mindset to embrace that life is a continuum of risk, an inextricable part of life. In decision-making, whether for personal or business, I focus my energy on clarifying my key priorities, and if meeting those priorities outweigh the perceived risks. This fresh mindset has allowed me to direct my decisions and actions more purposefully towards my life goals. Read more>>

Stephanie Y Jolivet | Sayezz Pilates & Beyond Owner, Intuitive Mover & Teacher

You know, I’ve never thought of myself as a risk taker. But when people learn that I walked the 40 miles of the Maryland portion of the Appalachian Trail in a single day; or that I climb aerial fabric; or when they see I ride a motorcycle; or when I introduce myself as a Los Angeles transplant who moved to the city nearly 7 years ago with her husband and two dear friends without jobs, I get a chance to see myself from the outside, and say to myself, “Huh. But those aren’t risky behaviors. I followed my gut in all of those adventures.” I began climbing and moving and performing before I can remember, really. There’s a famous story in my family of the time I opened up the kitchen drawers next to the refrigerator to use as steps and ended up perched atop the fridge, my – what I image must have happened – little naked feet dangling over the edge, smiling down on my mother, as she very calmly, very gently, asked what I was doing up there. Read more>>

Carrie Stevens | Author, Health Advocate & Entrepreneur

With high risk comes high reward. It was my teenage son who reminded me of that while I was comentplating female solo travel in 2018. While traveling, I was writing my memoir, UNRATED “Revelations of a Rock ‘n’ Roll Centerfold” (now available on Amazon). As I examined the external factors of my life, I realized that every choice I have ever made was risky, and sometimes crazy. But had I not lived my life unconventionally, what would I have to write about? My son is smart. I guess the apple doesn’t fall far from the tree. I wish I was as smart at my scientist father though. He is the brains behind my business, StayYoungandSkinny.com and the inventor of my revolutionary antiaging and weight loss product, The skinnynnaX System. We make a great team because he’s ultra conservative and I am ultra creative. It’s a perfect balance. Read more>>

Katie Toscano | Digital Marketing Strategist & Business Owner

I always considered myself a risk-averse person growing up. In fact, much of my childhood was spent actively avoiding taking risks and hiding behind my shyness. I grew up in a very stable home, chose a very stable degree in business, and started my career at a well-established financial firm straight out of college at 22. I always envisioned I would grow my career there, steadily climb the corporate ladder and retire somewhere around 60. But I think I had it wrong. I wasn’t risk averse; I was calculated in my risk-taking. I weighed my decisions with so much care, but ultimately, I always went with my gut. And risk, for me, was not always about taking huge chances, sometimes it was just choosing to do the hard thing, or get uncomfortable. By the time I had kids and was powering through the corporate world, I quickly learned that the risk wasn’t necessarily taking a giant leap, the risk was in NOT taking it. Read more>>

Michael Blevins | Director, PGA Producer, & Entrepreneur

I have a tattoo on my arm. It says “Fortune Favors the Bold” Rewards in life directly correlate to risk, and most of the time, the amount of reward can correlate with the amount of risk you agree to put yourself through. Life is scary man. Everything can kill you. A lot people hide resentment for people doing better than them. Nothing is guaranteed. All you can do is say ‘Fuck it, I’m just going to do what makes me happy and I’m going to figure out a way to make it work where I can do what I love and still live the lifestyle I want to live.’ Eventually you’ll get paid more and more for doing what you love because you will be really GOOD at it. Read more>>

Cara Monday | DJ Miss Monday

If I go a day without taking a risk then I have settled for complacency. Exploring the unknown is a daily routine. I feel comfortable being uncomfortable. There’s so much to learn and improve. I’m grateful for every struggle and success. More importantly, I don’t fear failure, I fear not trying. It takes drive, determination, sacrifice, and motivation to be the best we can be. Without taking risks, we would never know how great life can be. Read more>>

Tara Gonzalez | Hair Stylist & Owner of TGHairLove

I think of risks as motivation to live a very blessed and fulfilling life. If you don’t take the risks then you stay in the same spot your whole life and never grow to your potential. The world has so much to offer and taking that next step to your dream is all worth it! If I never left my job at a credit union to pursue my passion for hair I wouldn’t be where I’m at in my career today. If I never left my corporate salon job then I wouldn’t be the business owner I am today. Everything falls into place when you follow your dreams and take that risk. Read more>>

Tony DeVoney | Visual Artist

Risk taking is something I personally see as crucial to growth and success. In my own life I’ve taken risks to explore and embrace my sexuality as a gay man, since in todays society and in certain areas of the world its frowned upon, some even labeling the ”decision” as a setback or flaw. Risks are necessary. It follows over into my career as well, with almost every choice I’ve taken in the pursuit of my art. Moving to California from my home state of Louisiana at the age of 20, where I knew no-one, surviving only off of an idea of what could be. To recently quitting my full-time job and living strictly off of my savings to direct all my focus into my work, having no clue if anything will ever come of it. In my experience though, it’s the things that scare you the most that seem to have the biggest turnout. We all only have one go at this, so why not risk it, who knows what could be. Read more>>

William Hung | Motivational Speaker & Professional Poker Player

I see risk as potential new opportunities. When I auditioned for American Idol back in 2004, it was one of the biggest risks I took because I had no professional training for singing or dancing! But I was able to turn negative into positive. Same thing for other endeavors, like video games, trivia competitions, and poker. I am willing to try new things and I am determined to create the life I want, not what other people tell me I should do. Read more>>

Bryan Norton | Concept Artist, Visual Development Artist, & Illustrator

Life is all about risk management and how you perceive risk-taking. No matter what your profession is eventually there is a risk you take at some level. It may be high or low or somewhere in the middle, but it is always there. As an artist, I knew I was entering a world full of risk and maybe more so than say being in a “safe” job. Being an artist almost requires a certain level of risk tolerance just to participate. To thrive, it demands it. Read more>>

Zack Hurley | Entrepreneur

Most people would define risk as “the possibility of something bad happening” or of having a loss of some kind. This assumes that high risk is a high possibility of something bad happening and low risk is low possibility of something bad happening. The problem here is that we’re leaving out the part of the equation where we define “bad”. When I think about risk I try to focus mostly on this area. What is the worst possible scenario? What is the best possible scenario? In business, this can take shape in a few different areas. Psychological rejection: This is less about losing something of material value and more about getting your feelings hurt. When you’re an entrepreneur, selling yourself and your ideas is paramount to success. So what is the risk factor here? Worst case scenario in most cases is simply being told NO. Thats it! a simple no, or no thank you is pretty much the worst case scenario. Read more>>

Peggy Kelley | Event & Wedding Designer, TV Host/Producer, Speaker, Coach and Soon to be Author

Risk to me is trust and courage, the ability to live in the uncertainty which is so true today. Risk equals…What if? My “what ifs” are many…They started here…. What if I sell everything I own and move from Cleveland Ohio to Houston Texas? You start fresh and build a new life… What if I take a job in radio not knowing anything about the media? You work for three top radio stations and learn a new skill that you can use going forward… What if I put a U-Haul on the back of my car and drive to Los Angeles to start again? You learn that your little girl dreams come true…What if I fall in love and it doesn’t work out? You learn about love, and all of the magic it brings…you learn about divorce and the pain that comes with it and most important you learn you are stronger than you think…What if I become successful in the events industry…cater the Emmys… cater the Oscars…actually attend the Oscar’s as a guest? You learn the importance of collaboration and service. Read more>>