HOW MUCH WAS YOUR FIRST HOME AND HOW WERE YOU ABLE TO AFFORD IT?
THE DRAGON, MICHELE ROMANOW: So I am going to be the only contrarian here, because I’m probably the only person here that doesn’t own a house. I spent my money investing in tech companies. The fact that I didn’t own a house gave me an enormous amount of freedom. So I was able to sell a company to Groupon and move to Chicago. Then I moved to San Francisco. My first home was really a sailboat with two bedrooms. We have to stop thinking of rentals as something you do when you can’t afford a house because there is a new group of millennials that does not have their goals set on home ownership. THE CONDO KING, BRAD LAMB: Well, my first home was not a home to live in. I was living at my parents’ house. I was squirreling money away to become a real estate investor. I bought a townhouse in London, Ont., for $34,000 in 1985. I sold it a year later for $57,000. THE PLANNER, JENNIFER KEESMAAT: My first house was with my husband, we too squirreled away. I lived with my in-laws in order to save up. Then when we bought the house, this was 18 years ago, and rented out the main floor and basement. We lived in the top two floors. We saw that as a strategic way of entering a market in Toronto, which at that time, we thought, was really overheated, even to the point where we moved into Roncesvalles. Our neighbours came over when they heard we’d bought our house for $360,000, and said, "Oh my God, what have you done? You don't understand this market. You paid way too much money.” Of course, that house now, which we are no longer in, would trade at well over $2 million. THE FINANCE ACE, JOE OLIVER: It’s 1973. My first son was one year old, so it was time to buy a house. We started looking. It was either a small, old place downtown, or in the suburbs around York Mills and Leslie you got a big barn. So we opted for the latter. In the six months that we were looking, prices went from an astonishing $55,000 to $65,000. So I was distraught. My financial life was in ruin. I went to the bank, and I spoke to Earl McLaughlin, who was head of the main branch, who later became the CEO of the Royal Bank. “How much do you wish to borrow,” he asked. “$65,000,”I said.