Immediately out of high school, I moved to the Rocky Mountains to work in the resort industry – Jasper, Banff, Lake Louise. At first, I lived in staff accommodation. It was like all the fun of university dorm life – except without the classes!

It didn’t take me long to learn, though, that if I worked hard and resisted the temptation to party, I’d attract positions of greater and greater responsibility. With increased income and decreased expenses, I found my savings account steadily growing and began to feel the weight of a new kind of responsibility: How would I invest my newfound wealth?

I remembered hearing about how my parents had once owned a rental property, so I read all I could about the subject. Shortly after my 21st birthday, I started actively pursuing real estate investments. I looked first in Field BC, and then Golden. Finally I settled on a trailer home in Lake Louise. I made a list of all the wisest people I knew, sought their advice, and before long, I became a Landlord.

While I no longer consider trailer homes to be real estate investments (because they are depreciating assets), this one was located at the base of one of Canada’s favourite ski resorts, and had a breathtaking view of Mount Temple. I arranged a longstanding agreement with Skiing Louise and my little investment became the preferred home of Ski School Directors and Mountain Managers for many seasons to come.

My most impressionable memory came one spring as I spent several months travelling in California. My only source of income was a series of post-dated rent cheques for my trailer. The income exceeded the expenses by $274 per month! What a great feeling it was to provide a home for someone else and make a modest profit in the process.

I vividly imagined a day, in the not-to-distant future, when I would have multiple sources of passive income to deposit each month…

… and that, I believe, is the reason many entrepreneurs frame their first dollar or cheque or contract.

Expert Tip:

Remembering your first deal helps you see how far you’ve come, and gives you courage to press on when new challenges come your way.

Please scroll down, leave a comment, ask a question, or share a story about how you celebrated a first win…