No Guts, No Glory

Eric Gilbert-Williams - EO Calgary

Article by:

Eric Gilbert-Williams
EO Calgary

Eric Gilbert-Williams is the founder and CEO of The Roof Hospital, a residential roofing and exteriors organization. Fun fact: Eric travels across North America performing with an amateur salsa dance team. Contact Eric at [email protected].


The road to entrepreneurship can be a rocky one, but no one ever tells you how big the rocks are. When I was 16, I dropped out of high school, had a drug problem and nearly lived on the streets. As the only son of a single mother in a family boasting of generations of respect- able careers, I was the black sheep. I was raised well and given plenty of love and support. My environment didn’t lead me down the road to destruction, I chose it. It was only when I turned 18 that I started to take a hard look at my life. Friends were getting hurt and some didn’t make it— I needed to make a change.

It’s amazing the parallels that are drawn between life and entrepreneurship. In many ways, I used entrepreneurship to change my life. I had the “spark” for as long as I can remember. Buying and selling used lawnmowers, while running multiple paper routes, were among my earliest ventures. When I realized that I had nothing to lose and everything to gain, I decided to quit playing around and take this “business thing” seriously. With ripped jeans, a cheap haircut and a thick silver chain around my neck, I started conducting business-to-business sales, cold-calling, knocking on doors … I was relentless.

Move on while you still can

The odds were stacked against me early on. To help me navigate through mistakes, I created a “Lessons of the Day” list, and found that jotting down insights anchored them deep within my consciousness. The more lessons I put to paper, the more effective I became. This became my roadmap to get ahead. And before I knew it, I started selling enough to scrape by. Soon, I was wearing the best sports coat Value Village had to offer. Goodbye, silver chain! I kept at it, and went on to discover the merits of 100-hour work weeks. It was tough at first, but there was one lesson that kept me going: “Move on while you still can.” So I did.

Never stop learning

As I matured, I began to open my mind up to the opportunities all around me. I read voraciously and hung out with every successful person I met. I attended workshops, seminars, networking events … and before I knew it, I started running them. At age 20, I launched my first company, which created, organized and hosted business events. I informed speakers that they could promote themselves if they delivered keynotes for free. I offered a website company the title of “event sponsor” in exchange for a website. I notified everyone in my Rolodex that a great keynote was coming to town, even if I hadn’t secured one yet. I never stopped learning, which meant I never stopped moving.

Putting it all together

After finding my rhythm as an entrepreneur, I thought I had finally made it. I thought I had done enough, and that my events were raking in the profit … but then reality hit me like a shovel to the head: I discovered I was dead broke! Each month, I had to transfer balances from one account to the other just to meet my minimum monthly payments. I was back to the beginning, struggling to move forward. The time had come to apply all of my lessons learned and get myself ahead for good.

I had been roofing on and off in Calgary for years just to earn some pocket cash, so in 2006, I made the leap and started a roofing business. I bought a rusty van, a used nail gun and hit the road. Thanks to particularly good winter clothing, an iron will and a small loan from my parents for winter tires, I picked up contracts and kept moving. Profits started flowing, and before I knew it, I was out of debt. Today, my company has 54 full-time team members, and we closed 2013 with more than US$5 million in revenues.

Throughout my rocky entrepreneurial journey, I kept writing down my lessons learned, reminding myself about the importance of growth through experience. Ultimately, I discovered that things happen for us, not to us. This is an attitude and mindset I’ve chosen to adopt. I always have a choice. A person chooses to do or be anything. I can choose what to do with the time I have right here, right now. And so can you.​


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