The Entrepreneur’s Journey – The Black Sheep

This is a guest post from Neil Shepherd and is part of The Entrepreneur’s Journey series.

When asked as a young child what I was going to do when I grew up, my response was:

“I’M GONNA WEAR A SUIT! CARRY A BRIEFCASE! AND GO TO WORK!”

I always knew I was going to do my own thing, that I didn’t want to work for anyone else, that I wanted people to work for me.

The First Steps

I moved to Canada from Barbados in 1979 with my parents and two older sisters because the economy was poor in Barbados, and my parents wanted to provide a better life for us. My family left everything they had worked for and built in beautiful sunny Barbados, and had to completely start over in Canada.

We arrived on a Thursday and by Monday morning my father had a job as a security guard making $3.25 an hour supporting 5 people. My mother took a job as an elevator operator until she was able to secure a position back into her career in banking.  

I became a father at the age of 17 while I was still in high school. Although I was young, and ill prepared to raise a child, I knew that I had a responsibility to do whatever I could to support my daughter.  So came my first full time job, working for a cleaning company scraping gum off the sidewalk in front of the Royal Bank Plaza in downtown Toronto.

I’ll be the first to admit that it wasn’t the most glamorous of jobs, but it paid the bills.

Sitting out there in the scorching heat all day taught me one major lesson – this was definitely NOT something I wanted to spend the rest of my adult life doing.

So at 19, in an attempt to make a change in my life, I made a decision to enroll in the Restaurant/Hotel Management course at Humber College in Toronto. While I was waiting for the program to begin, I was offered a 3-month contract at Sovereign General Insurance company as a mail clerk. After my 3 month stint, upper management took notice of my raw talent and offered me a full time position in the file room with the promise of paying for my insurance education.

I accepted the position, and my quest for insurance knowledge began there. My dreams of carrying that briefcase and wearing the fancy suit now started to became more of a reality.

Am I Doing The Right Thing?

My biggest fear was that of becoming just ‘another number’. To be given an opportunity to live life to it’s fullest and to waste it, just throw it out the window, like so many others do.  I wanted to be different, wanted to leave a mark and create something big.  This fear is what drove me then, and what still drives me today.

The fact that I may not have made that happen, or didn’t have the opportunity to make it happen, I suppose would be classified as my biggest fear.

Roadworks Ahead

My biggest challenge or obstacle, if you can call it that, was the fact that I didn’t inherit my business – I had to work for it.

Insurance is typically classified as an “old boys club” – it’s filled with suit wearing, scotch drinking, cigar smoking generations upon generations of men who have been handed their opportunities in life.  The difference between myself and them is that I wasn’t given it – I worked for it, and worked bloody hard for it.

My father, although not wealthy by any means, had a wealth of knowledge; I learned so much of what I know from him. He never took a day off sick, he never complained and he always fought for what he ultimately deserved and more often that not, received.

He didn’t have the luxury of being a member of the boys club as he had a family to take care of and support, kids to feed…and I truly believed he liked it that way.

One of my biggest obstacles is actually myself. I believe that my inherent need to constantly dissect everything, or drill it down to it’s purest format can sometimes be to my detriment.

Roads Most Traveled and Rocky Paths

“The reason partnerships fail is because of lack of candor – which is why I’m up front, and always say what’s on my mind.”

I’m not sure that anything I have done throughout my career I’d consider a failure. I truly believe that all experiences are to be learned from, whether positive or negative.

I suppose to the outside world a few of my partnerships could have been viewed as “failures”; however, I learned from them and only saw them as opportunities to grow and change. I always say I don’t believe in luck; I believe in timing, and luckily for me, timing has always been on my side.

Making The Grade

I am a grade 12 graduate who is now the sole owner of a $10 million brokerage without having any letters behind my name, or a silver spoon in my mouth. I had a lot of people hedging bets on my failure over the years and I have to say, there is no greater success for me than to have proven them all wrong.

Making It Happen

Don’t allow yourself to be spoon fed in this life, or wear rose colored glasses. You can’t expect someone to teach you, and you can’t expect success to be handed to you.  You must take the initiative and strive to learn on your own.

You have to grab a hold of your seat at the table and push yourself to expand your knowledge.  You need to have the ability to predict what will happen in the future, use all of your senses, stay ahead of the game, never let them see you sweat, and never let anyone intimidate you or make you feel less than what you know you are.

I have been called a visionary – and while I think this is a huge compliment for which I’m grateful, I also feel that it’s not just something unique to myself.  Everyone has a “visionary” inside – it’s just whether or not they choose to tap into that, and share it with the world.  That in itself is what makes us unique.

The End Game

My goal is to take this old school industry and turn it upside down.  It’s time to see things from a different perspective, and take on my “Be Different” philosophy. That’s what I’m all about, and what I will continue to be in the future.

I will end this with one of my favorite quotes, so poignant to me that I had it tattooed on my right arm: “I do not think that there is any other quality so essential to success of any kind as the quality of perseverance.  It overcomes almost everything, even nature.”

Be yourself. Be different.

Neil Shepherd is the CEO of The Shepherd Group, one of Canada’s leading insurance brokers who are looking to make people rethink how they view insurance. You can read more at The Shepherd Group blog and find out why they’re happy to be the black sheep of insurance.

- Disclosure: The Shepherd Group is a client of Bonsai Interactive Marketing.