Legend holds that Cornelius Vanderbilt had built a massive fortune in the steamboat shipping industry, but then realized the railroads were the way of the future and invested almost his entire net worth into railroads. The gamble paid off and made Vanderbilt one of the wealthiest entrepreneurs ever. But risks are inherently…risky. How do you think about risk and how has it affected your life and career? Some of our community favorites share their perspective below.

Two Lewis | Serial entrepreneur, entertainment manager, producer, angel investor, coach, motivational speaker, and philanthropist.

Back in 2004, when I was still creating my first company, PayPal co-founder and Facebook investor Peter Thiel said: “In a world that’s changing so quickly, the biggest risk you can take is not taking any risk.” The act of opening a business itself is a risk. Without taking a risk, there’s rarely a reward. So for me Taking risk is necessary, but t here are a few thing I do before taking a risk. I Look at decisions from a reward-perspective, not from a risk-perspective. I find ways to think outside the box to create solutions. I always view challenges optimistically: as opportunities, not problems. Read more>>

Calibleubird | Recording Artist & Content Creator

Risk taking is essential. Without it, everything would have to be calculated all the time, and that’s just not real life! Of course there are things you can control and plan ahead for, but taking risks is good. I’ve had to learn that myself. I’ve definitely taken [thought out and prayed out] risks. I’m where I am now because of a risk-really several. Read more>>

Dee Fomby | Stock/Crypto Trader & Music Producer

Without risk there is no reward. I would not be successful if it wasn’t for taking risk. You must take that risk. Read more>>

Thomas Cantley | CEO/ FOUNDER

In life it’s all about risks. Everything I do has a sense of risk and every choice I made has all been worth it. People told me I was crazy and couldn’t start my own streaming platform. They said it would be to hard and to big of an idea. But here I am with a killer team. Ex Vice President of VICE MEDIA and Refinery 29 and many more. I have got my first VC round and launching on Oct 28th. If I listened to anyone or listened to that reptilian brain telling me that this is to risky.. than I wouldn’t be building an empire. I also was told that donating a dollar off my subscription to charities was to much.. and I said too bad.. and I was also told it was to much of a risk to keep my content solely focused on “ feel good” because mainstream content needs conflict… and drama.. but I’m moving forward with a clear mission in creating a space for creators and consumers to be inspired , uplifted and fulfilled by contributing to worthy causes. Read more>>

Ava Pinkston | Beautician

When it comes to risk, I believe that its something everyone who has a special talent or skill should take. Taking a risk and quitting my 9-5 to focus more on my business has been one of the best things that I’ve ever done. There’s a saying that says you miss 100% of the shots that you don’t take, and once God revealed this talent to me, I knew that I had to pursue it by any means necessary. After I quit my 9-5 I was still in college, struggling to figure out how I was going to pay my tuition, and that’s when I decided to really take my business seriously and started to invest money that I really didn’t have into it. Read more>>

JJ Williamson | Music Artist

One of the main things I always encourage people to do is “follow your dreams”. For a long time I *thought* I was following my dreams, but it ends up I was just playing it very safe and close to the chest. When I decided to focus solely on my own music career, I realized that I was basically going to have to start over. I was going to have to start from the bottom and make it based on the merits of my talent and my ability to perform… and it wasn’t easy. haha It still isn’t, but it’s fun and I love it. I’m doing what I absolutely love to do and I’ve somehow made a business of it. People say “fake it til you make it”, but *I* say “believe it til you achieve it”. Read more>>

Angel Walton | Janitorial & Landscaping business

Exiting relationships for a season, homelessness, and trial and error with making investments. Read more>>

Sydnee Smith | Hair stylist

I think risk taking isn’t for everyone. But for the people who are not afraid to fall just to see how to properly stand tall. 4 years ago I left my home of 26 years Indianapolis, IN. My mother had passed a year prior and I was at the lowest part of my life. I remember my mother telling me that if anything should happen to her I was to go to Oregon to be with my father. I sold my things packed up my place. My dad came my 6 year old daughter and I away. I arrived in Portland on my mother’s birthday. I knew no one but my dad. I had no job and no place to live. I remember my father asking me what my plans where as we approached the city limits. I told him my plans where to take over. To create a name that’s known from Alaska to LA. Read more>>

Nicole Burton | Fashion Designer/ International Model

I think about taking a risk as a means of elevation. In my career as a fashion designer/model taking risk has played a huge role for me. I’ve pushed myself beyond my comfort zone, mixing fabrics, being photographed in boudoir, networking and meeting new people. Normally these were things that I would talk myself out of, from fear of rejection. Because I’ve taken these chances and pushed the envelope I’m seeing more opportunities and I’ve learned that just when I’m ready to give up, that’s when my breakthrough happens. Read more>>

Donvinnie Boykin | Author, Celebrity Stylist, Model, Actor, Designer, Public Speaker, Philanthropist, Entrepreneur, Producer, & Creative Director

Risk taking is the key to my success. Life is all about taking risk, and betting on yourself. I had to take on the fact of what’s the worst that could happen. I am a true believer that what you put out is what you will get back in return. With taking risk it builds confidence and opens up possibilities. By taking risks, you give yourself permission to try things out, I’ve learned, to fail, to grow and to explore. I got a chance to test my limits and go beyond what I believed was possible for me. From the start of my career I took a risk and entered into the fashion industry as a model knowing nothing about the industry. Read more>>

Ayanna Maria | Women’s Streetwear Brand Owner

For me, life is a risk. Waking up and assuming that your day will go as planned is a risk; physically and mentally. With my brand I throw out ideas and designs and I risk that they will be received with excitement (and orders placed). A lot of times, that’s not the case. Taking those risks though have allowed me to grow and develop on a personal and professional level. I gain more knowledge every time on how to navigate situations, what designs my market wants to see, and just how to roll with the punches. Risks are necessary. Don’t be to scared to do something! Read more>>

Jessica Kretchmer | Freelance Illustrator

As scary or terrifying as it may initially seem, risk taking is so essential – not just for an artist, but for everyone! Playing it safe or sticking closely to your comfort zone are completely fine ways of living out your life (I know I am certainly guilty of it) – but how else can we truly exceed if we don’t take the occasional risk? Besides the endless support from loved ones, I feel like risk taking has greatly shaped my artistic career. I took a risk going to an art school (shoutout to SCAD’s illustration department), knowing I could land myself in a giant hole of debt and wind up in a dead end job just to survive. I took a risk with my cut paper style, knowing that it isn’t the most popular or commercialized form of art out there. Read more>>

Amber Staples | CEO and Creative Director of Stapled, LLC

My mantra is that nothing worth having comes easy. Life is full of risks that you’re taking every single day. No matter how small the risk is, we are constantly making risky decisions to bring us to the next stage in our lives and careers. When I started my business, Stapled Events, I was working a full time job with a Fortune 100 company. I worked my way to the top of the company and demanded a 6-figure salary. In my corporate career I faced discrimination and unfair treatment, as a minority woman. I did not let this stop me and I continued to fight against the odds, to be at the highest level possible. Read more>>

Donyetta Washington | Mompreneur and Founder of Koko’s Closet, a children’s clothing boutique

Risk is the roadmap for me, I’ve been able to expand the Koko’s Closet brand by taking huge, scary leaps of faith. I think any entrepreneur will agree that’s the key to growth. If you let fear stand in the way, if you feel like you can’t make a move until you know every detail of the results, your business becomes stagnant. I remember how scary it was to travel for last minute celebrity pop-up shops, but making those moves has helped me create so many priceless relationships that never would’ve happened otherwise. Read more>>

Christy Phelps | CEO, Designer, Seamstress, Sewing Educator

I believe life itself is about taking risks. I believe taking risk is what makes or breaks your business. Risks is what helps push you ahead of the game. Everything that has been invented was by taking ricks. If you believe in yourself and your vision that’s what matters. Read more>>

Alex Berdysheff | Visual Artist

3. Taking no risk at all is a risk too, isn’t it? For an artist, each new piece is a great challenge and risk, no guarantee how good the final result can be, no idea how much time it will take to finish it, and there’s always a great uncertainty with the sales. Don’t forget to add a possible damage or loss of a shipped work. There’s a great adventure behind each piece of art, and what’s Art if not a Terra Incognita? Risk and success always come together. Success is mostly a result of all the desperate attempts to change the given reality and just partly of a fortune. Read more>>

Emery Gholston Jr | Co-Owner

Risk taking can be disastrous or prosperous depending on the reward and goal. Our business started off as a part time means of making extra money until I was laid off from my job. My beautiful, loving and supporting wife encouraged me to concentrate on the business full time and everything will be fine. It was pretty scary not knowing what the outcome or the hurdles you come across when having a business. But with a strong support system at home and faith, blood, sweat and tears you can overcome anything. Read more>>

Varick Brown | Master Baker/Cake Artist

When I think about Risk taking I think about being able to step out on faith and to fully trust God during the process to know that he will never leave me nor forsake me. This has played a major role in my life/career because I have a relationship with God and I listened and played attention to the confirmation, signs and prophecy that was placed before me over my life. So when I think about Risk taking I think about having enough faith to trust and believe that no matter what the situation maybe God will continue to lead me in the right direction Read more>>

Lindsey Locklear | Model/Actress/Influencer

It has played a tremendous role in my life& career or boy I wouldn’t be where I’m at today! Life is all about taking risks and knowing when something is right or wrong for you! I tell people all the time you don’t never know your full potential unless you take risks and set boundaries for yourself don’t waste yourself!! Read more>>

Scott ‘Doc’ Dachroeden | Touring Music Photographer and Guitar Technician

I’m a firm believer that big things come from taking big risks. I moved to America from Australia 22 years ago with $500 to my name, hoping to continue my career in the music industry. I started touring in vans, moved on to RV’s then eventually tour buses and private jets! I had no formal education in anything, just a desire to see the world and not have a boring life. Had I never taken that initial risk I might not have ever found this life/career. Read more>>