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.

Michelle & Richard Hammond | Owners of Le Bijou Holistic Spa

Risk plays a huge role in our business as well as our marriage and personal life. Our life experiences are very contrasting, not only due to our difference in appearance, but our upbringing as well. Choosing to be together has been risky, even if only socially, only because one of us experiences far greater risk on a daily basis than the other. The very appearance of us standing next to each other in the same room reminds others of risks they did or didn’t take. Read more>>

Laurie Skantzos | Visual Artist and Educator

When I look back on my art career, there is a direct correlation between risk and growth. Typically, preceding these occasions, a feeling of restlessness or dissatisfaction would arise and this would be uncomfortable enough for me to initiate a change of some kind to my practice. There have been many evolutions to the type of artmaking I’m involved with, and I have often risked losing my audience in order to explore a different direction. I feel that I’ve grown into the artist I am by following my heart and curiosity, despite taking a chance of alienating past collectors. Read more>>

Williy Lau | Film Director & Screenwriter

I think it’s the same as a lot of other creatives and artists, doing what we do is already a big risk that we’ll have to take, both financially and mentally. Because most of the time we don’t really know where we’re going, and what’s waiting for us at the other end. So we struggle, but if we could overcome the challenges, then we might become better at what we do. It’s kind of like hiking, you see this huge mountain in front of you, and you know you’ll have to get to the top to see what it’s like from there. You get tired and frustrated but you go on. Then you get to the top and see the beautiful view from there, but you also see there are bigger mountains in front of you waiting. Read more>>

Karina Felix | Pet Groomer/Photographer

I feel that taking risks is what has helped me grow my business. I have been very worried or scared at times I would fail and I have but I have succeeded more. I always persevere to try and learn new things and/or better my ways. Read more>>

Tania Mackey | Fashion Designer & Entrepreneur

I think about risk as opportunity. I always believed that if you thought too much into something, you can talk yourself out of anything. So in that regard I absolutely thrive off of taking risks. Don’t get me wrong, I’m not a gambler. I also don’t put money on the line I don’t have. But I always bet on myself. Everything I have done by launching NICZKA has been a risk. Working on NICZKA patterns at past jobs, getting me fired. Turning down huge promotions, because I wanted to launch my own company. Deciding I wanted a brick and mortar in a virtual world. There are always reasons you shouldn’t do things, but I believe you always have to take the risk on what feels right. Read more>>

Kryssy Simmons | Healthcare worker & Beauty & Lifestyle Influencer

When I consider taking risks I have to think about it different ways. Naturally, my first thoughts are all the great and possible things that will happen. Next thoughts of comparison creep in along with what will “they ” think. Lastly I think of all possible repercussions. After spending time going through the motions I remember that as long as I’m doing what makes me happy then taking risks on myself will always be worth it. Read more>>

Kimbles Hume | Stand Up Comedian, Producer, Owner of Kimbles ‘n Bits Comedy

I’ve never been afraid to jump in with 2 feet and honestly on occasions act on a whim or gut feel. When I was working as a marketing manager in London aged 28 I was having my annual review with my boss and out of nowhere I told them I wanted to be transferred to the states (I worked for an International publishing company). Read more>>

Nicole DeSimone | Entrepreneur & Model

In the words of Mark Zuckerberg, “the biggest risk is not taking any risk.” Taking risks has played a monumental role in my life and professional career. Growing up, I used to let fear consume me. I was a straight-A student all through school. I was motivated by fear of failure and falling short of perfection academically. I missed out on sports, clubs, football games, and recreational activities with my classmates. All because I was unwilling to take the risk of falling short of what I thought was “perfection.” Believe it or not, my father actually paid me $100.00 to earn my first B grade during college because he wanted me to understand that the college experience is more than just what is learned in the classroom. Read more>> 

Misty Conteh | Social Media Manager & Workout Enthusiast

I think taking risks is the best part of the reward. Taking a risk requires courage to face the fear of uncertainty. Are they scary? Absolutely. Not knowing what the outcome of something will be is terrifying. But if you don’t take risks you’ll never know. Taking risks is especially terrifying for me because I like to be in control of my life. I like having control over situations and knowing that everything will be okay because I’m making sure it’s okay. That’s where risk-taking really steps up to the plate. If I would not have taken risks, I would not have lived so many lives at the young age of 26. I wouldn’t be living in my favorite city in America. I wouldn’t be able to share my story if it wasn’t for taking a risk. Read more>>

Alecia Ashcraft | Child Photographer

I feel the rewards are always greater when you are taken. When I decided to go full-time with Photography I had been running a large family childcare for the past 16 years very successfully and it was a sense of security and comfort. Giving that up to go full-time with Photography was a giant risk but I’m definitely glad I I took it. I’m not one who’s afraid to fail I’m always willing to take a risk if I feel like I can succeed Read more>>

Simitha Singh Rambiritch | Dentist, Researcher & Entrepreneur

I learnt very early on life from my father that life is about taking risks. Despite living in apartheid South Africa, my dad, a person of color, gave up a stable monthly income to pursue his own business and his hard work paid off. I guess my entrepreneurial sprit comes from him and his determination. Like him, while working in a stable government job in healthcare, I opened a women’s accessory business in a new busy mall in South Africa, but very quickly learned that overheads, like high rent and wages can crush your profits quickly. Read more>>

Marsha Ashby | Owner, Star Room Reiki

Throughout my life I have always been wary of taking risk and have taken the safe, secure path. After all, a bird in the hand is worth two in the bush, right? All of the things that have happened in the world over the past three years caused me to take an honest look at my life. I realized that by taking the safe path, I was not being true to myself, but more importantly, I was cheating others out of receiving the gifts I have to share. That realization led me to make a decision that is bringing me great rewards. Read more>>

Mark Neal | Photographer and Digital Marketer

Risk is exactly what got me started in photography. After college I had no job opportunities worth mentioning and was running out of options. Then it was suggested to me to do something completely different – go live abroad for a bit. So I did. I lived in Madrid for two years and fell in love with photography initially due to people asking for more photos of my travels. Later this love was intensified when a good friend of me lent me my first film camera – a Minolta XG-1. Without the first domino falling of moving abroad I never would have found this passion. Read more>>

Urban Royalty | Singer, Songwriter, Rapper, Producer, Artist

Risks are a major play in any creatives life. You have to stretch yourself to new heights and be comfortable with being uncomfortable, change is inevitable. How will you truly know your power? A risk is betting all on you and being all in. Standing on your true capabilities. Walk alone. We live in a era and a city where the common sound gets you recognition. A risk is saying “Im stepping away from what everyone else is doing”. A risk is getting a knock on your door saying you have 30 days left in that place your staying. A risk is sleeping on your cousins floor. A risk is spending that little bit left on your passion. Read more>>

Katie Ganhewa | Areola Tattoo Artist

I believe that taking risks is a natural and necessary part of life. There are so many unknowns and each unknown requires some level of risk, in my opinion. Regardless of the outcome, there is always so much we can learn through the process of taking risks about ourselves and the world around us. My family and I moved to San Diego a little over two years ago from Virginia. In doing so, I was afforded the opportunity to choose to take a risk and begin a new career path. I have always had a passion for creativity and art. Read more>>

Raziel Cariaga | Hairstylist

I believe risk is necessary in life. “What if I fall? Oh but my darling, what if you fly?” To me, the only way to find specific answers or to get what you want in life, is to take that risk. When taking risks, there will always be a chance you won’t get the results you hoped for, and jumping into the unknown is really scary, but as a result you can say you were brave enough to try, it was a life experience/lesson, and you are able to walk away with more wisdom, then you move forward with your next game plan. Read more>>

Kate Tova | Artist

It felt like a big risk when I started doing street art around San Francisco during the bad part of the pandemic. All my life I’ve done everything by the rules and always asking for permission. It hurt me to see so many of San Francisco’s businesses hopelessly boarded up, and I felt like I was drowning in negative news all the time. I decided to create these large colorful hearts to uplift spirits and bring hope to the community. I’d paint and embellish them on canvas at home. Then, in the morning I would go and glue them to boards outside and spray paint the outline with drips. Read more>>

Judy Lin | CEO & Founder of Digital Marketing Doctor Agency

I believe a part of being an entrepreneur is the ability to take risk. If you are completely risk-averse, then entrepreneurship is not for you. Better to get a 9-5 job. In my career and especially in my digital marketing agency, I have taken many risks that felt uncomfortable, but logically was the right step and the right choice. A part of growing your business is having to take that leap of faith with a new service, a new partner, a new technology that never really guarantees positive outcomes or success, but your first step forward offers that opportunity of success and opens up a new possibility that may not have been presented before. Read more>>