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Why entrepreneurs are willing to risk it all

This article is about the road less traveled and looking at your specific surroundings. I’m here to share insights on how being fearless is a developed personality trait and building a tolerance for risk comes in tandem with experience. How some entrepreneurs are, and most must learn to default to being, possibility-driven and hopelessly optimistic. […]

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Why entrepreneurs are willing to risk it all. Photo by Wes Hicks on Unsplash
Why entrepreneurs are willing to risk it all. Photo by Wes Hicks on Unsplash

This article is about the road less traveled and looking at your specific surroundings. I’m here to share insights on how being fearless is a developed personality trait and building a tolerance for risk comes in tandem with experience. How some entrepreneurs are, and most must learn to default to being, possibility-driven and hopelessly optimistic. To shed light on how to stretch yourself beyond your comfort zone and continually reach for the next level to get ideas out into the world. I’ll cover world travel, culture, and why seeing new, fresh perspectives is critical for growth and innovation. I’ve been very lucky to have learned that solutions can come from the most unexpected places and that a cross-pollination mindset can give an entrepreneur an incredible edge. Most importantly, I’ll touch on finding something you’re authentically passionate about and why it’s critical for your fulfillment in life to go all-in on whatever it is that you set out to do and really dedicate yourself.

I graduated from the Rhode Island School of Design (RISD) and when college ended and that new chapter of life began, I threw myself into the water. Right into the world of entrepreneurship. My first venture in business was an Industrial Design consultancy. I then went on to create a series of other companies in a variety of new and different industries as I discovered opportunities and learned along the process. A common question I get is “how were you ok taking on all this risk?” and “It seems like such a tough path” or “how did you decide to jump right into running a business?” and many people want to know where to start. At the time when I graduated from college and started my first business, I didn’t yet realize how hard that path might be and what level of tenacity was required to execute successfully as an entrepreneur. I guess the saying is true about ignorance being bliss and I really didn’t know what I was up against. At the same time, there was a lot of real-world education and personal growth along the way. I made a lot of mistakes. I’m proud of what I’ve been able to accomplish and learn and who knows where I’d be today if I never took the risk and chose to take the path of entrepreneurship. And the point is that you don’t know what is on the other side of the venture you’ve been thinking about, or the book you want to write or project you want to create. Here are some things I’ve learned along the way.

1. Take the road less traveled

I grew up with parents who had a unique approach to life and deep compassion for all people. They found a way to travel to various places world and shortly after getting engaged, joined the Peace Corps and lived in Sierra Leone. I’m adopted and my parents were always ultra-transparent with me about this aspect of life for as long as I can remember. My adoption is, was and has been an authentic part of who I am. I’m fortunate to have parents taught me the value of diversity. They adopted my brother and I at a time when adoptions weren’t necessarily as common and the process was certainly not easy or a normal one with several very testing challenges along the way. They encouraged me to see all aspects of a situation and to not automatically disregard things that were interpreted as “different”, “unusual”, or not in line with the norm of what everyone else was doing in the world at any given time. In fact, having different perspectives and experiences could be advantageous and something to be embraced and not feared or shied away from. They taught me to stand up for and fight for what you believe in while also being respectful of others and seeing all points of view, regardless of whether you agreed with them or not.

My childhood growing up, had a huge influence on me and I learned the importance of being fully engaged in life and living full out. I was very fortunate to be adopted into a remarkable family. My grandfather Norman Phillips, was the head of the former Department of Meteorology at MIT. He also worked on the ENIAC (Electronic Numerical Integrator and Computer) which was the first programmable general-purpose electronic digital computer that was Turing-complete and built during World War II. He spent time in Stockholm writing a numerical forecast program for the Swedish Air Force. Advising also led to trips to Leningrad, Moscow, Lisbon, Hangzhou, and London. In Hangzhou, he collaborated on a report for the World Meteorological Organization on the likely consequences of nuclear war. In 1964 and 1965 he was part of the Commission for Dynamic Meteorology meetings in Leningrad and Moscow during the cold war. He was a man of few words and at the same time, I learned so much from him and from every single person in my family. There are things to learn from everyone you interact with and every person has a different and unique perspective. Taking the road less traveled will lead to true innovation and a life unlike any other. You’ll be able to discover things about yourself and create the life you want to live without following the direct path of another. The truth is that even if you wanted, you can never really emulate someone else’s life exactly. You’re in a different time, place, society and circumstance. Things are always different than you think they will be and the world is always changing. It’s great to have role models and people to look up to and simultaneously, this is your life to build and your unique world to explore.

2. Realize what’s around you

Being raised in Schenectady, New York gave me a special perspective. Schenectady is a once-booming industrial town that inevitably fell on hard times as manufacturing jobs and contracts in the United States moved overseas. If you’ve ever visited, it’s not a place that you’d automatically think, this is a place of bountiful opportunity and promise. A lot of people I grew up around would tend to put it down at times, saying they didn’t expect much to happen from being in Schenectady. Yet, it’s also the same city that was featured in “The Place Beyond the Pines” with Ryan Gosling and Bradley Cooper and various other moves have made references to it. Schenectady has a rich and important history and is diverse in all regards. Settled in the 17th-century by Dutch who arrived in the Hudson Valley area. Schenectady eventually went on to be where Thomas Edison founded what today is General Electric. George Westinghouse also invented the rotary engine and air brakes in this part of New York State. American Locomotive Works, also known as ALCO, once made virtually every steam and diesel locomotive for the United States. The General Electric research facility called Knolls Laboratory was originally located in Schenectady and relocated nearby to Niskayuna. Needless to say, there is an abundant concentration of people much smarter than I, who hold Ph.D.’s located in the area where I grew up.

As urban, gritty, and sleepy as Schenectady might have come across to me as a kid, it also undeniably helped inform me and my mindset. In addition to manufacturing and technology, the legendary Basketball coach Pat Riley was raised in Schenectady which has always been inspiring to me. Peers from my high school ended up going all different routes. Some dropped out and seemed to disappear, some went to Harvard, Berkeley, Cornell, MIT, West Point or local colleges and others stayed in the area. Many ended up packing their bags for New York City if they wanted to get out of town. Schenectady wasn’t the most glamorous or manicured place to grow up but it was real and authentic. The teachers at Schenectady High honestly cared about the students and they were passionate and came from all walks of life which is incredibly lucky for a public school. It didn’t matter if you were in an art class or AP physics, this trait held true for teachers across the board.

3. Be fearless and bold

In thinking about risk-taking and being fearless – I’m now confident that it’s a muscle that is built over time. Some people are lucky to learn this at a young age while growing up, depending on the environment they were born into or through pivotal experiences they might have had early on in life. For most of us, learning from your mishaps and gaining wisdom while not going through life, afraid to take risks when things might not have worked out prior, is often a learned trait. It’s a fine art that requires practice and some seemingly painful lessons along the way. In reflecting back on my life growing up and thinking about how I got here – there have always been aspects of my personality that have been entrepreneurial. When in high school, I was heavy into two things. Skateboarding and fine art. It was almost like I had to find something I loved and make a dent in the universe. I wanted to be really good at skateboarding and also enjoy the process of getting there and building skills. I also enjoyed the social aspect of meeting people through skateboarding culture and the dedication people had to the somewhat rogue sport. With art, it was thrilling to brainstorm ideas and think about all of the things that could be done and put out there into the world. I couldn’t sleep many nights in high school because the inspiration would just keep coming all hours. It’s almost like I was unable to turn it off and just go to bed like a normal person.

Being raised in upstate New York, I used to drive into Albany on Friday nights in the dead of winter, which in retrospect can be brutal in that part of the country, to attend figure drawing classes simply because I wanted to be a remarkable artist and illustrator. Honestly, probably not what normal kids at that age were up to or found interesting but I wanted to learn new things and grow – it fueled me. I always wanted to take on learning something unique and something insightful. I really enjoyed hanging out with people who cared deeply about whatever it was they were involved in. I found that putting myself into cultures and social circles that were progressive with purpose and outside of what was trendy just for the sake of it, was where I was able to flourish and contribute. I saw going through life in a constant state of wonder as an advantage because it allowed for a well-rounded perspective. Knowing about more things is a way to connect with other people and what matters to them. It creates a bond and inspiration and I learned later that what happens in one area or industry, can fuel solutions in another. Getting new perspectives and knowledge can only help to bring a unique and fresh view to cause breakthroughs in an array of places in life.

4. Be possibility driven

I suppose in a way, I’ve always had entrepreneurial tendencies. When I was in high school I screen printed branded t-shirts to sell. In the summertime, I pressed skateboard decks in out of hard rock maple in an effort to make some extra cash. I couldn’t afford the industrial press equipment used in factories and I had been given my grandmother’s old boxy and rusted out 1984 Chevy Caprice as a first car. To make the skateboards from the wood veneers and laminate the sections together, I would park it on top of a two-part cast mold that didn’t look pretty at all and wasn’t sophisticated but got the job done. The goal was always to make things to sell that others would want or be interested in. I didn’t know it at the time but I was developing a brand, thinking about the story behind a product, building affinity and thinking about the marketing of anything that might catch on. As a kid, it was all just fun and something new to explore.

In those days, I had no idea what I was doing but I just knew I wanted to create my own version of the proverbial lemonade stand. The idea of being able to create and manufacture something from nothing that other people found value in has always been incredibly enticing. To be able to generate value and create real, authentic equity out of thin air is a fascinating pursuit that I constantly think about to this day. How can we make the world more fun, more interesting, more sustainable, healthier, more advanced, all while encouraging and ushering society into the future? In the beginning, as a young entrepreneur, I gravitated towards what was trendy or looking at what had already been done, to try and follow what was out there. I was learning and growing and it was later on in my career that I remembered the lessons my parents taught me about diversity. I realized the value of doing things that were different, and not just for the sake of being different. Doing things that were different with purpose and taking risks could be an incredible advantage to attract early adopters who would then attract others to the product or idea.

One of the fundamental aspects of an entrepreneur I’ve learned is to be able to put yourself out there with bold actions and audacious goals and ideas. People may not understand or get it right away. A vision is created and shared and evolved over time. You have to put something out there and put something at stake and be different to stand out. It’s fundamental to keep standing up again and again when it feels like you’re constantly being knocked down. Optimism in entrepreneurship is an important part of standing up and bringing solutions when things may seem stacked against you, your idea, or your company. When I started my first company and in retrospect, the idea, and excitement around being able to create something remarkable and impactful, dramatically outweighed the potential risks of failure that might have mentally come up. I wasn’t thinking of all the things that could go wrong, I was automatically thinking of all the things that were possible.

5. Stretch yourself and continually reach

While in high school, most of my time and focus was spent on fine arts classes and honestly kind of disregarded my liberal arts classes for the most part. I didn’t think much about the type of work I was doing in those “regular” academic classes and didn’t think I had much control over what I was studying. A good friend at the time one day told me “You know, you’re a smart kid. You should probably put yourself in some type of more advanced class or classes. It’s no wonder you’re not engaged in these courses. They aren’t that challenging.” That one comment changed everything and really resonated. My first thought was ‘Yeah, you know what? You’re right, I can!’ I immediately signed up for more advanced classes and everything started to shift and become more interesting all of a sudden. Instead of just doing the bare minimum, I was now being challenged and I was around other kids who wanted to be there too! This was when I realized that if you put yourself around high-performers, at least for me, this gave me energy and a support system. Once I signed up for these advanced classes, I also discovered that I could tap into a lot of the other resources the school had to offer. I put myself into the indoor track program and later ended up running marathon distances.

I additionally signed up for the new crew rowing team that had started at the school that same year. As an inner-city program with very limited funding, we had a lot of challenges. One day at practice, our boat sank the first year of the team. We had gotten two old free heavy wooden boats that were in pretty worn from the neighboring town of Niskayuna. They were heavy and most of the modern boats were made of much lighter fiberglass material. It didn’t matter though because the opportunity was there and the boat almost sinking was a funny story we could all bond over and laugh about later. The coach had been involved with the Harvard rowing team and we got to learn from a great teacher. Sometimes having poor tools can mean that you’re able to focus on developing the skills versus just obsessing over or being distracted by the equipment and it pushes you to do better. When you finally do upgrade to the “nicer” fiberglass boat, you’ll also appreciate it that much more.

6. Explore places and perspectives

A close childhood friend’s dad was a painter. He used to live above the world-renown artist Chuck Close in New York. Occasionally, their family would take me to New York City to drop off paintings in Chelsea and SoHo and I got exposure to life in the city. I made many trips to New York City growing up to visit skateboard, visit gallery openings, to experience what one of the most worldly cities had to offer and what New York meant and stood for. I was fortunate enough to be able to get a scholarship at Maryland Institute College of Art (MICA) to study Illustration and then later, to RISD to study Industrial Design. Through these college education experiences, I got to meet and interact with people like musicians and artists such as David Byrne of the Talking Heads. Ironically, I actually got to meet him twice, once at MICA when he was visiting and the following year at RISD. I did work-study in both schools, assisting with audio and video, and was asked to help out especially when visiting artists came to present. Ironically, David had also attended MICA for a period before later studying at RISD. I got to meet people like Steve Wozniak when he came to Brown University and collaborate with student engineers at Brown University whose fathers worked for places like Porsche, Boing, and NASA.

Growing up, I had never left North America until halfway through college. I was accepted into Strate College which at the time was located in Paris to study Transportation Design and I had to get a passport for the first time. I didn’t know anything about other languages or cultures and threw myself into the water. I ended up learning basic French while I was there by studying at Alliance Française in Paris in addition to attending Strate College. Once again, getting exposure to many leaders, I was able to meet several car design experts and realize that deep influence was possible. I later found that I could take another leap to do work in Seoul, Korea when my first company got a design project with a company that was based there. I didn’t know how it was going to work out or exactly the steps to take but it got figured out along the way and it was an amazing experience.

7. Solutions can come from unexpected areas

As a skater in high school, our group of friends listened to a lot of hip hop as many skaters on the east coast did at the time and we had read a few places that the Wu-Tang Clan were really into playing chess. That instantly made chess “cool” and there wasn’t a lot to do upstate New York at that age. Someone in our group heard about a local club where you could volunteer and keep elderly seniors company by playing chess with them. We went a few times and it was definitely the path least chosen. Once again, probably not something my peers were doing at the time. Opportunities like that gave me a chance to chat and spend time with people who had a deep life experience and expanded my mind. I’d like to think those unique interactions had a profound impact on me, even as simple as they might have been.

While attending RISD I had the chance to learn about the Bauhaus movement which was incredibly inspiring. The idea of cross-pollination and interdisciplinary study was highly attractive and is deeply rooted in RISD culture. While living in New England, I visited the Gropius House which was the family residence of famous architect Walter Gropius located in Lincoln, Massachusetts. Walter Gropius was a German architect and founder of the Bauhaus School. Along with Frank Lloyd Wright, Mies van der Rohe, Le Corbusier, and Alvar Aalto – he is widely known as one of the main pioneers and masters of the modernist architecture movement. In starting my first company I constantly thought about this and sought out inspiration from other industries, professionals, and visionaries. How could you take something over there from a seemingly unrelated industry and apply it over here to this area?

I wanted to get as much exposure to as many skills as I could early on and I took on a handful of internships in college. From working at an architecture firm to a photography studio, a model-making shop outside of Boston and a job at a medical design company – they all provided different skills and experience. When I was a sophomore in college, my professor hired me to design for Arena, the leading swimwear brand. One thing led to another and I realized I could make money by freelancing, regardless of my age. It set off a chain reaction and took me down the path of exploring what is possible in business and how to make things that people want and are a contribution to society. Things that create real value and actually change the world.

8. Find something you really care about

Find that thing and pour yourself into it. It’s important to find something that sets your soul on fire. Doing something you love will actually fuel you versus drain your energy. That’s the difference between dreading the day to day mundane routine, versus leaning into whatever you’re doing and loving every minute of it. You don’t know what’s on the other side of the fence until you start taking action on that project, company, or idea. If you have a passion for what you’re doing, even if it’s challenging, you will feel fulfilled and can look back at the end of the day satisfied knowing that you’re living a life full out – even if it’s hard as hell. For me, one of my passions is teaching others and I believe in sharing knowledge and perspectives that are unique and authentically letting people in. One way is to share it candidly through content like this and this post is a reflection of some of my life lessons so far and I’m sure there will be many more to come. I’ve had a lot of chances and these unique opportunities have helped me develop many eye-opening perspectives early on. Today I always look out for and try to work on the really big shifts happening in the world and work to predict what’s ahead and important to society.

What matters to me now is the idea of time. I wish someone told me when I was young, that time is the only thing you can’t buy or get more of. For everyone, there are 24 hours in each day. Not necessarily in the way that some high-performing people think of time, in terms of trying to maximize every single minute and second at any cost just for the sake of efficiency. What are the keys to living life in a way that counts in the ways you want it to, in a way that is a contribution, in a way that has an authentic impact? In business, every new venture is going to have it’s set of challenges. As I think of launching new business ideas, I think to myself, what is worth working on and dedicating myself to? It’s not so much about the level of difficulty and it’s more about will it be worthwhile to do at the end of the day? Startups are challenging and what will get you through the darkest hours and the biggest challenges has a lot to do with how much you care and believe in the vision.

It seems the most successful attribute for any entrepreneur to have is the ability to get back up, day in and day out, no matter what gets thrown your way. Anyone can learn from this trait of resilience. No one is out of time. Even if you’re 70, you can take that art class or publish a book you’ve always wanted to write. There’s still time and opportunity. If you truly do what you love, that may very well be the key to not aging prematurely and loving your life – waking up your soul. You don’t even need to quit your day job to pursue these things. Or if you have a naturally higher risk tolerance, you can go all in and get a job later if things don’t work out to get yourself back on your feet. Whatever you do, follow your heart.

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