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.

Dynasty | Hip Hop Soul Artist & Creative Entrepreneur

I think that in order to move forward, some level of risk is always necessary. The only place where there is no risk is in our comfort zone. I was born and raised in Queens, NYC. After college, I took a risk and moved to Tampa, FL where I had NO friends. (I just wanted to move somewhere warm.) Well, the city embraced me and championed me so much that I went on to launch a wonderful indie career there. I worked with hip hop legends (including DJ Premier) – while I was in Tampa. Consistent shows and first major radio spin.. Tampa. I started touring internationally – from Tampa. The move proved to be a risk more than worth taking. I worked in corporate HR for years before venturing out to follow my passion full time. That was in 2015. I left to pursue music and to run my arts-based youth empowerment program. Read more>>

Anthea Zeng | Programming Coordinator

I grew up with my parents always telling my brother and I to opt for safety over risk, which has of course influenced how I approach life. Being able to take the uncertain path is a very privileged option. I think depending on your responsibilities and circumstances, the riskier option can bring about amazing opportunities, but can also lead to more stress like not being able to pay your bills. So in the end, it’s definitely up to each person’s risk comfort level and other factors. However that being said, for the most part, I am a fan of risk (even though it makes me nervous!) if it means that it could lead to better opportunities or a happier life. I have always been an advocate for exploring new options–if someone approaches you about an opportunity, schedule some time to learn more about it! You never know what could happen. Read more>>

Shannon Vivo | Boutique Owner

My mom tells a story of taking me to a big ballet audition when I was young. I was very intimidated & at the last minute told her I wanted to back out. Being the supportive mom that she is, Bonnie didn’t force me into anything and we left. When she got to the car she turned around and I wasn’t there; I’d turned around and gone back in to audition. Risk taking has never really scared me. Well, I shouldn’t say it doesn’t scare me, but I don’t let the fear of risk taking hold me back. I actually have a lot of fear and anxiety that I work through. But there’s a switch that I’m able to flip on within myself when facing fear/risk. I’ve come to think of it as what’s the worst that’s going to happen? I fail? Taking on a business that I knew nothing about was a big risk. But I had the confidence in my work ethic & creativity to believe that I could figure it out. Read more>>

Kadina Grant | Entrepreneur

I believe risk taking is needed, without it we wouldn’t have the reward that feeling of your hard work paying off. Risking taking allowed me to put faith into myself and my plans knowing that this will either pay off and end in a reward or I will learn a valuable lesson. Read more>>

Yoana Obregon | Entrepreneur & CEO

Risk-taking is something I’ve gotten very comfortable with over the years and come to think of it, risk is something I’ve never really feared. Growing up I was an adrenaline junkie – I’ve skydived, raced cars, rappelled and jumped off buildings, I’ve even done ladder climbs off flying helicopters, and most recently I flew a plane. As an entrepreneur, fearlessness and risk are one in the same and they are both essential, in my book. Being someone that has been exposed to or even sought out such risks, has been a huge asset in becoming an entrepreneur. There is a big unknown when you decide to take that initial leap – a huge risk; financially, mentally, emotionally and socially, but you have to be able to trust yourself and trust your abilities. I strongly believe the most important part of any risk is trust, within yourself. Read more>>

Dorothy & Cassandra | Owners of Ambiance Event Designs

Taking risk is inevitable when starting a business. You put your heart and soul into something with no idea of the outcome. Anytime you step out of your comfort zone and take a chance there can only be two outcomes; success or failure. With either one, one thing that’s guaranteed , is a lesson learned. We originally started off as a rental company with tables and chairs then quickly realized that we had a lot more to offer and tapped in to the balloon decor industry. With zero idea of what we were getting into, we still took the leap of faith and it has been by far the best decision yet. And as we grow, we are continuously taking risk and finding new ways to perfect our craft. Read more>>

Joel De Villiers (Spaceman Dela) | Rapper, Writer & Musician

I think that risk taking is an essential component to making progress in life. Whether it be creating art/content, running a business or inventing some new product, the idea of leaving one’s comfort zone and taking (calculated) leaps of faith is always a crucial factor in becoming great at what you do and blazing a path. Now this might not be the ideal way to go about things for most people, meaning you have to be prepared to fall flat on your face, to be humbled time and time again, and to face failure with resilience. I feel like many of us are way too caught up with our image and live with a deep-seated fear of messing up in front of others. If you operate out of fear, decisions never get made and therefore progress is hindered (trust me, I’ve learned this from experience). The goal is to not be stagnant; the path to success is not linear and it is far from easy, but you need to keep moving. Read more>>

Skyy Hinson | Businesses Owner

Everything in life requires risks. Waking up, going outside is a risk. However, sometimes, it’s not about the risk, it’s about how bad you want a different life. That same fear and procrastination that you’re allowing to control your life is the same risk that could change you. Read more>>

Pablo Grand | Music Artist & Event Curator

Risk, I feel, plays a huge role in my life and the steps I’ve taken to get here. Not many people are willing to wake up and say I’m going to pursue music and look for legitimate ways to make it happen. If you think about it every great story involved greater risk. Cinderella meeting her lover at the ball she risked to sneak out to. MLK and the famous sit-in protests for equality; they risked their lives for the greater good that ultimately came. Aladin freeing Genie was risking his love for Jasmine in a sense. So yeah, I feel like it’s pretty important to getting far and surprisingly I think a lot of people don’t take enough risk. The risks I’ve taken in my life have only solidifed one thing for me; anything is possible if you set your intentions on it. Truly I tell you, you will will never cross the ocean if you don’t risk losing sight of the shore. Read more>>

Reuben Stratum | Songwriter & Producer

I think risks are an important part of any endeavor you choose to pursue. Of course, your risks must be calculated and safe to the degree that you know the terms of whatever those pursuits are. However, if you know the benefits of taking a risk are too valuable to pass up on, it’s best to take them especially if you’re young and don’t have major responsibilities and commitments that you are attached to. Recently I had a conversation with a producer friend of mine who says he had a beat stolen from him by an unnamed major artist. He says it was just a play beat, nothing he took seriously. so given, he was more honored than upset about the exchange. I had to tell him though, that it was deeper than that. A lot of times I think smaller and local artists put themselves in the “I’m just doing this for the art”. Read more>>

Dr. Ashley Little | CEO/Founder Ashley Little Enterprises, LLC

I am a BIG risk taker! I believe in taking risks regardless of the outcome. Taking risks has been a blessing and very rewarding for me throughout my life and career. I am thankful and blessed for all the risks I continue to take on a daily basis. I am not leaving anything on the table and will give 200% or more every day. People miss a lot of amazing opportunities because of the fear of taking risks. We only live once so why not take risks and live your life to the fullest. Shoot your shot!. Read more>>

Laudz Fenelus | Singer/Songwriter

Risks have played a huge part in my life! Especially with my music. As much as I love music and I love making music it requires a lot of investment. I have to invest in myself before anyone else will invest in me. It is a huge risk that sometimes I don’t even realize how much I’m actually investing. I just believe in myself so much that there’s no need for a second thought. Risks are very important to any career if you want to advance you won’t get there by playing it safe all the time. The greatest opportunities will never be in a safe zone. Read more>>

Marley Desinord | DJ Marley

I hear the word risk and think to myself opportunity. You cannot grow without taking risks, especially in DJing. If you do the same thing over and over and never try something new, you will be boring and be like everyone else. If you want to stand out from everyone and be unique you have to take the risks and try something new. My career has been helped from risk-taking from the very moment I got over my fear of performing on Instagram and posting videos for the world to see and judge. Read more>>

Count and Jessica Foreman | Street Vendors, Caterers

Count Foreman: Risk has been a key factor in my life and my business. I would have not seen any progress if I didn’t take the RISK to bet on myself and build a business without capitol. I was denied by banks for small business loans and pressured by private investors that wanted to control the creative ideas and have a say in the way the business was structure . I had to silence all the noise and we set out to raise the money as a family. We been able to fund our business by becoming Street Vendors and with the income of our cleaning business. Instead of saving or taking family trips , we bought cooking and catering equipment. One of the biggest risk was becoming a street vendor in 2008, which in many area are frown upon. When we first started to vend we had to invest in equipment and gain the trust of the community. Read more>>

Killian Grondin | Realtor / Real Estate Investor

Taking risks is a great thing, hopefully they’re taken intelligently. When taking risks and succeeding, you often end up with a much higher reward than you would have gotten with a more low-key play. When you take a risk and fail, you learn something valuable about your decision and circumstances, and become more confident (understanding that failure isn’t the end of the line). I encourage people to take risks 24/7. The predictable path might be safe, and feel at home but it prevents you from achieving greatness and significantly limits your options. Especially when you are young, you’ll have less to lose. You’re making a decent salary in a company you’ve spent little time with. You aren’t married in most cases, you don’t have children, and you don’t have any other significant responsibilities. Read more>>

Alex Quin | Digital Marketing Expert & Brand Builder

Throughout my career I’ve always taken calculated risks when executing my business development strategies. Taking measured risk is something that will often play in your favor if you are well prepared and informed. Thinking with a balanced mind is key so you don’t make decisions based off emotion. All risk you take in life should be measured and calculated with logic and data if possible. The biggest risk you can take is one in which you are informed little about. Don’t be afraid to ask questions or reach out to experts who can consult for you. It can be tempting to give in to advice on social media, or to take advice from fiends or family but you must always keep in mind that not everyone is qualified to give advice. It is also important to keep in mind that you should not compromise your values, or your integrity in the process of taking risk. Read more>>

Annie Tao | Speech Therapist, Pianist, and CEO/Co-Founder of Always Keep Progressing

Quitting my full time job to start my own business and pursue entrepreneurship was the biggest risk I’ve ever taken. Raised in a traditional, Chinese household, I was always taught to do the “safe” thing. At first, leaving the stability of my job was scary to me. I didn’t want to break away from what I had been raised to do and I wasn’t sure what the outcome would be. Being a young, minority woman, I was not sure if I had what it takes to run a healthcare company, given that the healthcare industry is dominated by the older generation. However, I used all of these obstacles to motivate myself rather than let it bring me down. Fast forward 2 years, and I now have my own healthcare clinic with a team of amazing therapists that provide services to children with Autism and other disabilities. I still think back sometimes and realize that if I had never taken the leap, I would not be where I am today. I’m very grateful for my co-founder, who has always pushed and encouraged me to face my fears and reach my full potential. Read more>>

Chris Klapper & Patrick Gallagher | Collaborative Art Team

Risk is very much at the heart of creativity – financially, professionally and emotionally. Artists by nature are entrepreneurs. We are heavily invested in ventures requiring deep levels of commitment of time, effort and resources. All without a clearly defined path, zero guarantees and no safety nets. A benefit of direct collaboration is that it allows us to bring both of our expertises together and helps us push towards more ambitious projects. As interdisciplinary artists, we’re always looking for new mediums and technologies to incorporate into our immersive installations. We have never shied away from complicated concepts. Currently our work is focused on decoding subjects such as particle physics, higher dimensional math and raw data, which are all great inspirations for us. We also really like to push the boundaries of mediums, so the risks associated with experimentation always comes into play. Read more>>

Ruben Figueredo | Creator

My life has been full of risks, in both my personal and professional life. Over the years, I have gotten better at making more calculated risks where I don’t lose everything I put it, whether it’s time or money or both. I have created or been involved in 6 startup companies in the last 8 years where I risked my time and personal finances. Half of those were a total bust, and 2 of them are still moving along (2 stagnant due to COVID19, and 1 was founded during the 2020 Pandemic). Of course, the reason I took the risk every time was because the potential reward outweighed the risk 100 to 1. Taking those risks to reap the reward motivates me to keep pushing forward as I don’t have a choice but to put 100% of my effort to it’s success. Risk it for the biscuit. Read more>>

Jake Dewar | I Help Doers Achieve More of Their Person Goals.

Nothing great was ever accomplished without taking on a little bit of risk. Risk is one of those things that I believe is best approached with thorough research and proper planning. When you’re tasked with making a risky decision, having appropriate insight and prior knowledge into whatever it is you’re deciding on ALWAYS allow for a higher rate of outcome success. As an entrepreneur, taking calculated risks is essential for not only taking the first step towards self-employment and creating a business, but also for making daily decisions that may impact my business as a whole. “Possibility” and “Chance” are both synonyms for the word risk, and to me, those go hand in hand with progress and innovation. What type of business do I want to create?. Read more>>

Amy Rodriguez | CEO & Lead esthetician of Skinfluence Miami

Risk taking is an absolute must when you are growing a business or even starting one. When you get comfortable you definitely stop growing because you are okay with the space that you are in, which is amazing if you feel like you are good there but if you are looking to grow as a person or if you’re growing a business there has to be risk involved. To me risk can be little things or big things like interacting with new people that can help your business, Asking for guidance, getting rid of the things that are holding you back, even purchasing that one expensive thing that although it costs it will help your business grow! Just do it! Do it smart but do it!. Read more>>

Laura Waitze Zuckerman | Mother / Wife / Entrepeneur

I believe people over think everything, including risk. Life is about taking chances and going for it! I had worked in the garment center in New York City in my early twenties for an amazing husband and wife team who were starting their own clothing line. It was just the two of them so the knowledge that I gained in a short period of time was unimaginable! I learned everything from cold calling to how to design and make a garment. These tools gave me the understanding know how to make my own piece. At that same time in my life, I started to work out at the gym and found that the bra tops were incredibly unfashionable. Coming from the fashion industry, I thought, I want to change that. Again, working in the industry gave me contacts and the knowledge to proceed full throttle and turn my idea into fruition. I did not even think about “if” I was going to accomplish it and the risk involved, I followed the steps I learned from my bosses and proceeded until I had samples to show to potential buyers. Read more>>

Joy Williams | Vegan Chef

I view risk as opportunities for growth, staying in your comfort zone can only get you so far and in some cases it’ll hold you back. Taking risk has allowed me to become a career firefighter at 22 years old and a vegan chef/business owner at the same time. Read more>>

Honorable Kelli Ann Thomas | Board Member, Community Council 14, Sub Area 144

The quote “No risk, no reward” comes to mind. Last year, I took a huge risk in my career. I decided to take of leave of absence in the summer to run for a position on my local community council. Being a organizer, I had strong relationships with members of my community, political knowledge, and experience in electoral politics. My background gave me the confidence to stop working and campaign. However, I did have to sacrifice. Not working for 3 months was tough on me financially. I exhausted my savings and had to borrow money from my parents. Also, campaigning during a global pandemic was uncharted territory overall for politics. Knocking doors and talking to voters are proven tactics of winning an election. However, doing those activities would put myself and voters at risk of transmitting COVID-19. Thankfully, I was elected despite those challenges and proudly serve as a board member on Community Council 14, Subarea 144 in unincorporated South Miami-Dade County. Read more>>

Maidenly Pham | Copywriter

Risks keep life fun! I find the the risk/reward ratio to be subjective since the desired outcome might not always happen, but that brings a lesson which is a reward in itself. 2020 started with me taking a huge risk. I left Ogilvy NY, a global agency that’s backed by a holding company to join Founders, a creatively led independent agency with a team of about 30. We’re based in Miami but have offices in Mexico City, Kingston, Buenos Aires, and now New York! Some people thought that was an insane decision since we were still in the midst of a pandemic and job security to them meant staying with a large shop. But my partner and I both felt it was the right time, the right opportunity, and the right risk. And we were 100% correct. Read more>>