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.

Katja Rieckermann | Professional Saxophone Player

Risk taking has been a big part of my life and career. I didn’t start playing the saxophone until I was 21 years old but I had set my mind to becoming a professional sax player even at that time. While everybody was telling me I was crazy and I would never become good enough I practiced for hours every day for years in order to become a better player. And a couple of years later I was able to support myself doing gigs back in Germany. When I was in my early 30’s I took another big risk and moved to Los Angeles. Of course I had to start all over again to network here in the US to make the right connections. Eventually I got called to audition for Sir Rod Stewart’s band as a saxophone player and I got the gig. I toured with him for the next 14 years from 2001 until 2015. Read more>>

Sierra Mackenzie | Creative Director, Songwriter, Actress & Model

In thinking about risk, the idea is you never know unless you try. I remember first starting out on my ten year journey as a music teacher, when I was barely fourteen years old and had parents asking me to teach their children. I had played for ten years myself at that point, and didn’t think I was capable, but my mum helped nudge me along to the point where I thought, “I have to try.” (I owe her big time for that one.) Ten successful years and forty-fifty weekly students later, I ended up passing the business along to my sisters as I endeavored on my next risk of moving continents to Australia. The risk taking business is, to be honest, terrifying on the surface; but there’s something – whether addictive or beautiful – about the free fall of that risk and not knowing quite where you’ll end up. Read more>>

Marta Kantorowicz | Executive Pastry Chef, Founder & Creator of MaLA Sweet Treats

I strongly believe the saying, “you’ll never know until you try.” I would never be where I am today if I had not taken so many risks! Risk-taking has always been part of my life and has molded my career every step of the way. I grew up in Poland and studied organic chemistry, thinking I’d work in forensic science. But after I received my Master’s Degree, I realized something else was calling my name. I knew I wanted to spend my time creating and somehow bringing the splendor and magic of my childhood to life. So in 2002, I decided to take that first risk and I opened my own flower shop. It wasn’t long until I realized I had a keen eye for art and design, and my flower shop became a huge success. But even though business was booming and my clients were loyal and happy, I realized I still wanted more. Read more>>

Kelly O’Grady | On-Air Correspondent & Storyteller

I consider risk taking necessary to progress. If I am not taking a risk, then I am becoming complacent. I have learned that it is extremely easy to be lured in by the promise of the familiar, and the stability of following a path others perceive as impressive. There are clear markers of success and there is a comfort in knowing the steps you need to take in order to achieve your goal. Up until a few years ago, I existed squarely within that trap. I had spent my life achieving things in service of this coveted life I mapped out in my mind, without ever evaluating if I truly wanted them; an MBA from Harvard Business School, the management consulting job etc. That does not mean that I didn’t work hard or learn anything during these experiences – far from it. Read more>>

Jacob Yoffee | Composer

As a musician there is risk in everything you do. The idea of paying your bills by performing or creating music is, to put it blunty, ill-advised. But musicians are amazing people, we help each other, we look out for the up & coming generation — it’s almost a familial culture. That makes it work in a lot of ways. But it’s still a risky business. The ACTUAL business side of it is brutal. You get used to a certain amount of uncertainty though and it’s easy to feel like you’re always pushing yourself, living on the edge, thinking BIG. But over time you find that you start following a path of safety; the same gigs start coming around and you can count on them every week, every few months or every year. In order for me to expand as a business I’ve had to take some big leaps of faith – consistently. Read more>>

Liz Marz | Self-Love Coach & Spiritual Teacher

I always say: “no risk, no magic”. I believe taking risks and being courageous is an essential part of the growing and evolving process. If we play it safe, we end up stagnant, and often times settling for “just good enough” in our lives. I believe we incarnated into these bodies to experience life. We were given the gift of our senses to go out in the world and use them, which means trying new things by going to new places and surrounded ourselves with different kinds of people. We are here to be seen. We are here to share our gifts and connect with others. This in and of itself is a courageous act. 5 years ago I left behind my safe life in New York. I had a steady job a great boyfriend and a solid group of friends. The problem was, I wasn’t completely lit up! I felt like something was missing. Read more>>

Calvin Davis Jr. | Artist, Songwriter & Producer

I view risk in a positive manner. I have taken many necessary risks in both my life and in my music career. I wholeheartedly trust in the process. I’ve learned that things may not always go as expected, but as long as you keep a positive mindset and learn from the experiences thrown your way, you will grow and evolve. I embrace being in uncomfortable and challenging situations. Taking risks are meant to scare you and overcoming this fear is your VIP ticket to experiencing new and exciting things. This is where you learn some of life’s most valuable lessons. You are able to self reflect and build self awareness, which, in turn, builds character. This pandemic has inspired me to innovate how I market myself and my music to fans. Being a risk taker gives you the ability to analyze situations and gives you the perspective into your own capability. Read more>>

Mackenzie Martin | Choreographer, Director & Founder

Risk is such a crucial element of success and a critical cornerstone of building beautiful things. I have often found when I’m approached with questions seeking answers in how I’ve built three businesses, a lot of it correlates with risk taking. Considered risk is advantageous because it unlocks doors and opportunities you might have left shut and opens your mind to possibilities you’ve not yet dreamed. I find people’s fear towards assumption of risk is a deterrent because of it’s possible proximity to an outcome of failure. To utilize risk in business and in life, we have to be okay to fail. This is not to say risk blindly without well researched and robustly informed information. But it is to say that most great success stories lie dormant on the steps of life’s front porch because we are too crippled with fear of potential failure to open the door. Read more>>

Kayla Greene | Fashion Model

I feel that risk play a major role in your life. Without taking risk you can’t say that you tired because you never took a risk to see how it plays out. Learning how to balance my work life with my home responsibilities while trying to model was a great battle. I had to weigh out my options on making a huge decision to travel for modeling. At the time I wasn’t making a lot of money , my mother and I made enough to get by but not to just get up and leave whenever. Therefore I saved money from 3 paychecks to help support me get from the New Orleans all the way to Los Angles California. I told myself no matter what happens I will make sure that I put enough effort in. Therefore I might not walked away being a top model overnight but I gained a lot of knowledge and gained a relationship with others in the industry. Read more>>

K. Elle Jones | Personal Brand Consultant, Producer, Filmmaker & TV Host

At the root of every decision, lies a potential risk. I’ve never been one who has liked rigid rules or believed in the ‘status quo’ mindset, so while taking risks can come with its own set of obstacles, I focus on the potential opportunities that may result in my taking a risk. I’m an avid storyteller at heart – it’s in my DNA, but I haven’t always had a career or jobs that allowed me to fully embrace my deep love for creativity and storytelling. This became a big issue for me, and I decided to do something different. Read more>>

Kendell Smith | Singer, Songwriter & Musician

I think of that sage advice that many of us hold as true, but need reminders as of how to live it, “The biggest risk is not taking any risk at all, and If you risk nothing, you risk everything.” I would be fooling myself if I say that I do not think about risk. You may be asking yourself, why would a family man with a wife and two children ages 5 and 3, who is an assistant principal entering his 16 year in the field of public education, with multiple credentials and graduate degrees, who has taught two courses for a UCLA graduate program, want to venture into something like the music business.? I have to know if that small voice inside of me is telling the truth. The calling. I remember an interview about John Frusciante, guitarist for the Red Hot Chili Peppers, in short, he said that the music will never let you go. Read more>>

Juanita Caldwell | Personal Trainer

Risk taking has played a major role in my happiness and overall success. The biggest risk I’ve taken has led to me making the best decision of my life! I moved across the country and created a fitness brand that started out as just an idea! Before August of 2018 I’ve always played things pretty safe, my next step was always calculated, and I always had my plan b-z already figured out. Playing things safe started to get boring- I was yearning for more, waiting to discover my passion but scared of failing along the way. The first step to taking these risks was embracing my fear of failure and then accepting it. Once I became comfortable with the idea failing, the risk started to seem more attainable. So far my two biggest risk; moving to California and starting Nït Fit have been huge successes that keep fueling me to take more. Read more>>

Dan Rosenboom | Musician, Recording Artist, Trumpet Player, Composer & Producer

Choosing to live as an artist is inherently a risk, and thus every subsequent aspect of one’s life and career carries an element of risk. Throughout my life, I’ve often made the riskier, less stable choices because the soul-filling rewards seemed too enticing to ignore. I’ve been so fortunate that many of those risky moves have resulted incredible experiences and successes. There have been obstacles, setbacks, and failures along the way, but embracing risk and charging forward has allowed me to cultivate an authentic and exciting life, and defined the very nature of the way I view the road ahead. Read more>>

Chase Constantino | Choreographer & Creative Director

I think we all fear risk, we are afraid of the consequences of it. What will happen if this risk I am taking doesn’t work out? What if I fail? What if people judge me? I think risk brings about many doubts in our mind that allows ourselves to second guess our intentions. I would be lying if I said I don’t fear risk, I do. For someone that prides themselves on their accomplishments, I am always afraid that the task I take on will not be perfectly executed. But I think it’s important to have fear, because it shows us that we actually care about what we are doing, that it means something to us. I think we should take inspiration from the fear to push us to take risks for the things we are passionate about. As simple as it sounds, we will never succeed unless we try, and try, and try. Read more>>

Stacie Martinez | Designer, Illustrator & Owner of The Lucky Bandana

Taking risks is not something that comes naturally to me, and for most of my life it’s something I have avoided whenever possible. I like (and prefer!) stability and predictability vs. the uncertainty inherent in taking risks. However, there have been a few times in my life when I saw that the consequences of doing nothing were far more risky than doing something. Twice in my life now I have pivoted my career, both times leaving behind stable positions to pursue other interests and avenues. And I don’t regret it for a minute. I have learned that taking risks takes practice – it’s never comfortable for me, but it does get easier. Read more>>

Callista Mei | Host & Pastry Chef

Risk is the scariest yet most satisfying die to roll. The uncertainty of your decision is something many people wouldn’t even gamble with but like they say; there’s no reward without risk. When I decided to go out on my own and create a brand that was uniquely me, of course I was terrified. But I had spent almost all my life being told what to do, how to look, what to wear, what was wrong with my body and what roles I fit into; exhausting. I got to a point where I thought, “If people aren’t going to like me, they may as well not like the real me.” Funnily enough, the moment I decided to embrace truly who I am and what I stand for, people gravitated more than ever. There’s something about a person who takes the risk of being unapologetically themselves, with no regard of the negative feedback, that I think people see as brave and inspiring. Read more>>

Chris Ngo | Fashion & Business owner

If you’re not willing to lose it all than don’t even bother getting into business. Business isn’t simple and if you are going to be safe about it, don’t get into it. It’s a lot of calculated error that can and will happen so your best bet is to be willing to take a Huge L because nothing is guaranteed. Read more>>

Lisa Brugger | Artist, Musician, Entrepreneur, Business Owner & Creative “No-Box” Genius

I feel risk-taking is vital to a life worth living and a successful business. Without risk, there is no growth. Success in any way takes risk and growth. They go hand in hand. There are no expectations, so it allows you to be open to possibility. My life would look completely different without risk. Without risk, I would still be living in the small mid-western town in MO that I grew up in doing what most everyone else did, stay put. I would also be living with regret for the life I missed out on. Not every risk brought success immediately, some quite painful at the moment, but as I look back, those experiences allowed me the success I have today. I took a risk when I left a job with a nice income 4 years ago that was making me sick and ONLY serving the owner of the company. I took a risk when I started my network marketing company not having a clue what to do. I stayed with it until I did. Read more>>

Jennifer Archie | Butta Maker

Taking risks has always been tough for me! The fear of the unknown or what’s on the other side of this has usually stopped me from taking risks. Being comfortable is easy, but you pay a high price for unhappiness. In 2018, I was extremely unhappy, stressed, and miserable at my job. I needed to take ownership of my life and make some serious changes. So, I decided to quit my job. I had no idea what my next step would be, but I felt better just to know I was free. After numerous job rejections and dead ends, Junie Bees Butta was born! Read more>>

Tory Jones | Founder & Designer

Risk excites me. The greater the risk, the more appealing things are to me. Nobody starts their own business without a great amount of risk. Be it financial, emotional, social, or otherwise. I would never have been able to build a business, raise children, travel, or partake in many of life’s daring adventures if I didn’t believe the rewards have always been worth the risk. Read more>>