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.

Lee Scrimmager | Spiritual Practitioner & Assistant to Film Director

Risk is absolutely necessary in order to achieve any goal in life. Taking risks has confirmed my confidence and lets me know that I can truly do anything I set my mind to (as cliche as that sounds). You don’t know what you’re able to handle until you thrust yourself into it. I’ve realized that I can accomplish a lot though I might not think it at first. All it comes down to, thinking it, putting a plan in action, executing it, and allow everything to work out. Some things might not be smooth and easy but it’s all a part of the journey! Read more>>

Lena Báez | Film Director & Writer

The most fulfilling moments of my life come from taking risks. I genuinely prefer making mistakes to the feeling of regret. The idea that I could have experienced something or learned something new without living them, haunts me, because I will never do and I think “what I waste”. By taking risks, I’m still uncertain of my future or the results from a task, event, etc but I know that something will come out of it and that will help me take a step towards my personal or professional success. Taking risks can be scary, and I think that’s part of the experience. Read more>>

Barbara Close | Lettering Artist & Calligrapher

T.S. Eliot said, “Only those who will risk going too far can possibly find out how far one can go”. And Renoir said, “One must from time to time attempt things that are beyond one’s capacity.” I’m Barbara Close, a Lettering Artist/Calligrapher and Artist. I’ve been doing this work for over 40 years…and still love it. I find, because of great quotes like these, that it keeps me always interested and intrigued enough to “take the risk” -to see what elso can be done. As an artist, I like to ask myself “What if…..” There may be a more exciting way to try something, if only I would take the risk to see what could be done. Read more>>

Samuel Mokelu | Founder of Mokelu Pictures

I think taking risk is a very fragile concept. Yes it’s great to take ask but it’s also very intimidating because you never truly know if it’s worth trying. As an artist my job is to create stories and in hope show people who are willing to listen to what I have to say. I’ve paced myself over the years to take minimal risk yet with a high reward if done well. As years gone by the risk taking has just gotten a bit bigger and I’m able to see what’s really worth taking the risk or not. Read more>>

Michelle Borquez | Cofounder of Lebae Inc

Risk taking is the foundation of any great endeavor because, as the saying goes, without risk there’s no reward. It’s really easy to stay where you’re comfortable, where things feel familiar, and where you feel safe; but if you are someone who has a dream, and you allow fear of failure or fear of the unknown to hold you back from reaching your full potential, then you will miss out on endless moments of personal transformation. Starting a business can feel intimidating, and there will be many obstacles along the way, but if you have the courage to take the leap, I promise you, you will find fulfillment and growth along your journey. Read more>>

Christopher Pedraza | Analog Photographer

I’d be lying if I said risk wasn’t terrifying and that it immediately triggers my anxiety. But…risk is an opportunity – an opportunity to try something new, to overcome odds, to create something you never could have before. Taking risks has been critical in my life and career as an artist, from the very beginning of deciding to become a full-time photographer. When it comes to being an analog photographer every shot is an exhilarating risk of not even knowing if the photo turned out until you pull it out of the developing tank. Being an artist has actually helped me to think of risk differently by accepting it as a fact of life and learning to see the unknown as a sort of freedom. Read more>>

Susanna Brisk Sexual Intuitive® | Helping you tune into your authentic, intuitive sexuality, which I call Sexual Intuition™.

I started out young as a stand-up comic and also acted for many years, so you could say I’m familiar with risk. When I pivoted from the entertainment business to being a Sexual Intuitive® it was a pretty big risk because the term didn’t even exist yet, so yes, risk much and risk often! I teach intuition, which is all about calculated risk. Intuition can be defined as tapping into an unconscious conclusion you draw, which includes what you’ve learned from your senses. So, it is calculated, because you’re not acting on a whim, but on a somatic deduction after some very quick *energetic* observation. There is no reason to think that if any, all or most of your five senses were or are impaired that you would not be able to access it. Intuition, like most things that are felt but not seen (thoughts, feelings, chemistry, humor) live in the energy world, so they can be felt energetically. Some people feel tapping into that kind of power is a risk, but I can highly recommend it. Read more>>

Nicole Boyd | Founder + CEO of Prept

I am a huge fan of taking risks and a believer that the bigger the risk the bigger the reward. I have taken risks throughout my whole career from deciding to jump from one big 4 firm to another to get more into tech/consulting to leaving a corporate job for a boutique consulting firm with a more flexible and entrepreneurial working environment, to spending my personal savings and bootstrapping my company Prept. Read more>>

Robbie McLean | Actor & Producer

I think about risk as a necessity in the industry of story telling and especially was an actor, without risk you will never make the big moves needed to succeed. Risk has always played a vital role in my life and success. I made the difficult decision to drop out of University in South Africa and decided if I wanted to be an Actor I should go out there and make it happen for myself and wait for it to potentially happen. This was a hard decision and it was scary to walk away from a degree and pathway to a nine to five job. So I took the path less travelled. Read more>>

Alejandro Amezquita | Music Director & Guitarist

Risks are growth. Risks are the best opportunity to become better and move forward twice as fast as someone who doesn’t take them. Most people tend to think about the downsides when going into the “unknown”. What they need to realize is that going into the “unknown” is what’s going to take you places people don’t tend to get because they are afraid of taking that step. Moving to LA has been one of the most rewarding risks I’ve ever taken. I wouldn’t have been able to work with Mickey Guyton, Randy Jackson, Brian King Joseph if I didn’t take that risk. Saying “yes” to opportunities is also very important, even if you feel you are not ready. The truth is, there’s no such a thing as being ready. How are you going to be ready for something you have never done before? The moment you take that risk and get out of your comfort zone is the moment you grow. Read more>>

Jalen Nelson | Fashion Content Creator and Marketing Mentor

I personally love risks! A lot of people are afraid of risks and they’re afraid to take them but that risk you’re afraid to take will be the risk that ultimately changes your life. Before I started taking risks, my life was very much at a stance of just being comfortable. And the thing is, taking a risk could either be a win or lose situation but the point is you took a risk and now you feel more confident to do things. I started getting extremely consistent with my content this year and started taking major risks. I didn’t know it was going to get me this far in my career but it did. So if there’s anyone who wants or needs advice on taking risks, just take them. You never know what can come out of them, my entire career changed in 6 months just from taking a risk! Read more>>

Amber Lawson | Actor, Director & Dancer

When I was a younger artist, I was raised in a very competitive atmosphere. I grew to believe “risk” & “fear” were in the action of me putting myself out there to have others judge me. I actually lost myself in winning first place, actually finding my value in what place I received. Somehow, without the marks of competition in front of me, when I moved to Los Angeles from my comfortable hometown, I wasn’t able to create a distinction on what risk was. I kept busy, and that to me was giving it all I had. I played my career rather safe, played it small frankly and all the while, I was still able to nab some great bouts of success. It was “great”, I had something to write home about, make my parents proud, friends around me had wonderful things to say and I could convince myself that I was “giving it my all”. From the surface, I still showed so much promise, but I hadn’t even come close to unleashing my potential. Read more>>

Rachel Joseph | Nail Artist & Beautician

I would definitely not be where I am today if I didn’t take any risks! I have moved around a lot in my life growing up so starting over is something I’m used to. Meeting new people, exploring new areas, learning new languages, etc. My first big risk I would say is moving to NYC alone from a small town when I was 20, knowing it would be difficult but full of opportunities. I had to sacrifice a ton of my free time and pick up multiple jobs just to live in my dream city. Had to step out of my comfort zone multiple times which was scary but helped me learn a lot. I wasn’t aware of how hard it would be to get into the beauty scene so for awhile I wasn’t a part of the industry at all. Read more>>

Jennelle Williams | Writer & Filmmaker

Risk is definitely worth the reward. Every time that I have stepped out on faith and betted on myself, I reached new heights that I never even dreamed of. 2017 I drove across the country to start my career in entertainment. In 2018 I left my survival job after feeling stuck at that job and depleted creatively. A month later, I started as a Writer’s PA and worked my way up to staff writer in less than a year. in 2020, during the pandemic, I shot my mostly self-funded six episode web series. There were so many ups and downs, but we recently got accepted into our first (of many!) film festival! No one told me to move 3,000 miles away from everyone that I loved. No one told me what the future held after it didn’t work out with my survival job. And certainly no one told me to go into production during a panini and self fund most of the project as a first time filmmaker. But I had to take those risks to get to glory. I’m usually a planner, but some times you have to step out on faith and just DO. Read more>>

Alastair Ballentyne | Transformation, Alignment & Spirituality Coach

Risk is everything, it is an invitation to excellence resting on the other side of our own fears. Risk is something that has been the central pillar of my life from an early age as I didn’t have a choice, my path began because of risk. My career started as a musician, I took myself out of mainstream education to study music professionally (a big risk at aged 18). Once you start following the noise, it’s difficult not to be curious about the next whisper of a heartbeat over the horizon if you are aware of it. Read more>>

Adam Tanaka | Merch Consultant & Advocate for Children’s Mental Health Awareness

It is scary as hell to think about stepping out into the unknown, with no roadmap on how to navigate. And if you sit and think about it too long, fear begins to creep in which can push you back even farther and will soon convince you that it’s not a good idea to move, and that you will more than likely fail…..But for me, sitting back, thinking, and succumbing to that fear is closer to failure than anything else I’ve experienced. Read more>>

meredith rodriguez | Sales & Entertainment Executive

There are days when I think of myself as very risk adverse, but then when I think about it, I have taken a lot of risk. Varying levels of reward have come, but I’ve never regretted the decisions I have made, since I would not be right here without them. I’ve been known to take an unconventional path, and sometimes that in itself is risky. I have always been driven to take on things I have not done before, to accept a challenge I can’t even see how to solve, but despite any self doubt I may have, failure was never on my radar. I had a manager once that used to call me The Firewoman. I could run into any fire and calmly figure out how to put it out, but also save lives and salvage everything I could along the way. Sometimes that meant I was assigned projects or accounts I did not ask for, but they ended up being great fits for me. Read more>>

Vanessa Loney, CMP | Event Consultant

When I think about risk, I think it’s so funny how far I’ve come. When I first graduated with my degree in accounting, I was very risk adverse. I had chosen a career with an amazing firm that had a clear trajectory: every year I would get a promotion and salary increase based on performance. I never had to worry about asking for professional development, bonuses or any perks because they were always offered in this job. It was the perfect job…on paper! But I felt something was missing in my professional life. I ended up taking a leap of faith and quit that amazing job to follow my passion for event planning. I took a pay cut and ended up with invaluable experiences that I never would have had otherwise. I got to travel to Kenya for work, won countless awards for the events I produced and gained the courage and confidence to eventually start my own company. Embracing risk allowed me the room to grow into the professional I am today! Read more>>

Demel Bolden | Photographer and Creative Director

I thrive off of pivotal moments where risk is involved. I love freezing time and displaying emotion through my images. Often times I find myself questioning to myself, “Do I climb on top of that?” or “Is laying in the middle of the street worth it?”. Often times that answer is yes, and I feel that some of my most captivating images come from those moments where I risk it all for that one shot. Read more>>

Da Eun Kim | Director, Screenwriter & Podcaster

To me, taking risks means choosing to trust and believe in myself. As a daughter of immigrants, I’ve been conditioned to default to self-doubt, to avoid the “road less-traveled,” and to settle and be grateful for what I’ve settled on. I find that when things feel risky, oftentimes I’m my own limiting factor, and in a world where people like me can already be denied so many opportunities, I should instead be my biggest cheerleader, believer, and advocate. By taking risks, I’ve grown and learned the most I’ve ever grown and learned. I’ve made a career change and have continued to embrace the inevitable changes that life will throw at me, and I’ve begun to see life as an adventure. I’ve attracted incredible friendships, partnerships, and relationships, and I’ve reimagined the bond that I get to have with my parents. Taking risks has only ever given me valuable lessons and empowerment; I wish we could rename “taking a risk” to “opening up a possibility.” Read more>>

Isaac Mashman | Business Owner, Creator, Public Relations Leader

Taking risks has been fundamental in the growth I’ve had over the last several years both in my personal life and in my business ventures. Without them, I think my growth would’ve been stunted. From taking one way flights to France and the only way I was getting home was if I closed a client, to staying in California without a secure place to live, these times helped shape me into who I am today. What some would label as immature, or as outright idiotic, I view as opportunities to increase faith in myself, develop skills, and experience things nobody in my life ever chose to. Read more>>

Megan Johnson-Zucaro | Virtual Online Host, TV Host and Author

I believe if you do not try you fail. Everything has a risk but in life you have to give all your creations a start and if you do not start and try you have failed. Working with so many people I have determined their biggest regrets are not trying and not giving something a shot so I always run towards the Roar and I have faith and know that if it does not work something better is coming. When you have faith in God and yourself you always will keep moving forward in a positive way. The key is confidence and Faith so that you believe in your self and know you can do it. Read more>>

Elisabeth Mack | Cannabis Entrepreneur, Clinician, and Educator

Like many, I was naturally risk averse, staying safe and looking for a way to contribute to my employer. But in 2015 I found CBD after a 2014 bicycle accident, and as I began healing I knew I needed to help others. I researched how the cannabis plant can modulate our body back to homeostasis or balance, and studied how to use all of these novel products to our gain. The passion I developed as I created my company Holistic Caring ignited my true purpose – and that led me to accept risks. Fast forward 6 years, I have created patient care services through a host of nurse coaches. Read more>>

Leila Broumand | Stylist, Vintage Curator & Creative

When one searches for the word ‘Risk’ on google the definition you receive is “a situation involving exposure to danger.” For me, risk has been something I’ve been exposed to at a very early age. I was raised in a family of risk takers, all successful entrepreneur starting with my father who would tell me never be afraid of trying something you really believe in, and failure is not an option. He was very instrumental in my outlook for life, wanting to always try new things, and meet new people. I was sent to a boarding school in Switzerland when I was 8 years old. That was my parents taking a risk to give me a great opportunity as a child. 16 years later who would have thought risk was something I would incorporate in my daily life. Read more>>

Alex Elena | Music Producer, Photographer

If you don’t take risks life would just be a flat line from the moment you are born until you depart to the other side. Risks are just brave decisions.
Without them you wouldn’t be able to grow and have stories to tell.
Stories that will often inspire other people to change or take a leap.
I took a risk leaving Rome for London when i was only 17 years old with 100 quid in my pocket and not knowing the launguage. Read more>>

Gregg Deal | Artist and disrupter

Risk has always been apparent in my life, if not my own work. Moving outside of popular culture, as an Indigenous person, always puts me at risk professionally. Things have gotten better, for sure, but I wouldn’t be where I am if I had not made some significant calculated risks. Having made my bones as an artist in Washington DC, I was asked to make my work “less Indian”. Not making that compromise has not only set the tone for the consistency and integrity of my work, but has established a standard that BIPOC often need to create in order to make work that is unapologetically true to ones self. Read more>>

Emily Murphy | Educator

In my personal life, I would generally describe myself as risk-averse. I love having a plan and knowing what to expect. The stock market scares me (no judgement). However, in many ways, taking risks has defined my career. I’m a big believer in trusting your gut when making decisions about work. There have been a number of points during my working life when I have chosen the less-obvious path, or perhaps made a decision that seemingly doesn’t make sense, but each of these choices felt right in the moment. Read more>>

Satele | Music Producer & DJ

Risk takes a big part of my life. When I was younger, I was always told by my OG’s that you cannot grow in comfort which why they call them “growing pains.” Without taking risks, you will never rep the reward from taking those changes. More recently, I’ve taken the risk of leaving my job after 9 years of working for the company and I am not sure what will happen, but I know the risk is better than being complacent. Read more>>

Sonia Barcelona | Musician & Photographer

As a songwriter and performer, I think risk taking plays a large role in my career. I started writing songs and sharing them in public just because friends pushed me. Looking back at where I started, if it wasn’t for them and for a certain amount of drive to get better, I don’t think I’d be where I am. It takes a bit of bravery to share art with the world, especially if you’re art comes from a vulnerable place. Read more>>

Keyonna Jones | Full Time Artist, Executive Director of Congress Heights Arts + Culture Center

I think the word “Risk,” itself is the reason many people don’t take them. Risk is defined as a “situation involving exposure to danger, harm or loss”. A “chance” on the the other hand is defined as “a possibility of something happening” – which allows for that something to be good or “bad”. I take chances. When I take chances, I’m betting on myself and allowing spirit to guide me to the experiences that I’m destined to encounter. Even the “bad” ones provide a perspective I can learn and utilize for better outcomes in the future. Taking chances has allowed me to advance and find myself in spaces and interactions that I’ve never even contemplated before. It has allowed me to understand the abundance of opportunities and possibilities that can be afforded to me, just by trusting and moving as my authentic self. Read more>>

Angel Phoenix | Emotional Expressionist & Social Media Slayer

Observing key differences between myself and those pedestaling my success, it becomes clear that the ability to enthusiastically embrace risk, marks the difference between them (non risk-takers) and I (risk-taker). Ironically, this risk is the same thing that has me vilified when said risk does not fruit reward. This is to say, that taking risks is a gamble in itself for the brand or business owner. Most people are confronted by those brazen enough to challenge mediocrity or safety. There is generally a lack of support towards those moving against the current. When things go wrong, a loud synchronised ‘we told you so!’ barrels in from the bleachers. When things go right, those same people round an eager applause for the victorious underdog. All of a sudden, the villain becomes the icon – the risk once demonised becomes the risk taking we fetishise. Read more>>

Melissa Meier | Artist

To me, risk taking is everything in art – you can’t make art without taking risks. While risk taking is surely a way to innovate and evolve one’s work, I look at it as a way to express myself in the truest form possible. For without risk, I lose a critical sense of excitement and engagement. Not being afraid to fail is the driver behind all that I do; failure is just part of the process. Discarding a piece after days of work, while painful, allows for growth and understanding of the material. And often with failure comes surprise. Read more>>