From Professional Sport to Tech Startup: My Journey into Entrepreneurship

When was the last time you stepped out of your comfort zone?

Take a moment to reflect on this question.

It was this question that lead me to deliberate some of my ownlife choices; mostly, my then-current career circumstances. Let me take you for a short ride through my experience and the decision to step out of my comfort zone.

I had always been fortunate to have good opportunities available with regards to my major life decisions. I graduated from Cornell University where I was a team member and a captain on the varsity hockey team. (If you watched the video, that was me getting hit, resulting in two separated shoulders, a concussion, and cracked sternum.)

I recovered from that hit, was drafted into the National Hockey League, attended a few NHL camps, and played a couple American Hockey League games before going on to play two years in the East Coast Hockey League. After finishing hockey I felt as though I was herded like cattle from one corporate company interview to the next. With each company came a different industry, a different letterhead, and a different job offer. I eventually settled on a “promising” job with a large company, in an industry I knew nothing about. Warning bells should have been going off, but I needed a job and picked the “best.”

After I started work, however, I was like many other college grads: working a desk job, punching the clock, droning away the hours and (unknowingly) feeling entirely complacent. I felt I was working an 8am-to-who-knows-when-o’clock job all to realize someone else’s vision. 

In hindsight, I maybe could have done something to change things sooner, but my ego had been satisfied with the good impressions I had made on upper-management and my wallet had been satisfied by the promotions that I had received. It was just my stifled mind and waning motivation that kept nagging me… what was missing? 

I wasn’t passionate about my job or my industry and was lying to myself believing that making six figures, driving a nice car, living in a great city, wining and dining, would truly make me happy. This was easy, this was comfortable,  this was already achieved. Even as I typed this post I recognized that lifestyle sounded pretty good—yet I wasn’t happy with the direction my career was going. I wanted the freedom to let my creativity, innovation, and work ethic flourish so that I could realize my vision. 

Truthfully, I was starting to believe that Loverboy had it all figured out when they said that everybody was “working for the weekend.” I felt like I endured each week only to to make it to the weekend and throw money away chasing one adventure after another. 

I was working a good job, making a good salary, and had a promising future in the company. But I didn’t feel challenged or that I was living my life to its fullest potential. I started questioning my life’s accepted values. 

I did not want to be complacent in my life or in my career, and when I was presented my next offer for corporate promotion, I kindly declined. I left behind the status quo and ignored the expectations of others; I gave up a $100,000 job with the potential for more and embarked into entrepreneurship.

While working for a large company I spent evenings and weekends working on a tech startup: Get in the LoopMatt Crowell, the founder, had recently left a career in corporate finance himself, in order to pursue entrepreneurship. Oddly enough, Matt’s career path had been strikingly similar to my own; NCAA hockey at Rochester Institute of Technology, professional hockey in the USA, a large corporate job and finally hockey in Belgium where he attended the Antwerp School of Management while completing his MBA.

When I first met Matt I was enthused by his vision for Get in the Loop, encouraged by his passion, and inspired by his commitment to helping others in need. 

Get in the Loop is a mobile marketing service that connects businesses with our paid members. Our service allows for full control by our business partners, who are some of the biggest brands in British Columbia, Maniotba, Canada, and the world: Brandon Wheat Kings, Canad Inns, Moxies, Boston Pizza, Harvest Golf Course, Sparkling Hill Resort to name just a few. Further, we also work with local charities and organizations to help raise money for their mission and goals.

For me, this was a deer caught in the headlights opportunity. An opportunity to work with a guy who is as passionate about learning as he is about life. So why did I even hesitate when Matt suggested I join him in an effort to take Get in the Loop to the next level? I knew exactly why: risk. 

Risk. That looming fear that holds us back and keeps us from chasing our dreams. The Oxford dictionary defines risk as a situation that involves exposure to danger, harm, loss—or worse, that ever-dreaded wounded ego. 

So how do we decide to accept the risk? In my experience it takes self-awareness and courage. The awareness to recognize what it is that you’re “risking” and what’s really holding you back: salary? Pride? Status? And the courage to accept and understand those things. 

I could have, and you can, stay in the cubicle and complain about the boring monotonous job or you can step out of your comfort zone and go after something that inspires, excites, and encourages you to improve. For me, the tipping point came when I realized the biggest risk of all is that of regret; looking back on missed opportunities and wondering what might have been. 

I had deliberated for months before deciding to take the leap into entrepreneurship and the tech industry, but ultimately, I knew that if I was unhappy with my current situation I was the only person who could change it. 

Opportunities are presented daily, weekly, yearly; and along with the pros and cons of each taken or passed over, there will always be the doubts and questions left unanswered. 

I could have stayed in my current position, accepted my newly acquired and specialized knowledge in an industry that I was not passionate about, and eventually regretted my failure to take responsibility for my actions. But I chose the road less traveled. 

I stepped out of my comfort zone and eight months ago Get in the Loop launched in Kelowna and recently raised capital valued at $2 million. We are currently entering three other Western Canadian cities and have plans to expand to five others in the upcoming months. 

I accepted the risk, had the courage to pursue an opportunity and left the comfortable confines of corporate salary to set out on my own. 

In the words of John Keating, Carpe Diem. You only live once; make your life extra ordinary.

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