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Investor and financial coach David Lester.
Investor and financial coach David Lester.

Me & My Money

Treating money as a best friend Add to ...

David Lester, 34


Financial coach

The portfolio

Penn West Petroleum Ltd., Imperial Oil Ltd., Husky Energy Inc., Cineplex Inc., Bell Aliant Inc., Telus Corp., Goldcorp Inc., AltaGas Ltd., Pengrowth Energy Corp. and the big banks.

The investor

As befits someone who has self-published a book on money - I (Heart) Money - David Lester has always had a great relationship with it. "I've always had this really positive association with money. When I was a kid my grandfather would bring over buckets of coins and I'd sit there and roll while I watched cartoons."

Mr. Lester's view is that what often holds people back financially is they have the wrong relationship with money. "If your parents fought over money, or you think it's complicated, you may decide you just don't want to deal with it." His view? Treat money as you would a good friend: "Respect it, trust it, and enjoy it."

His approach

Mr. Lester looks through the TSX 60, and cherry-picks the top-yielding stocks that also have a history of increasing their dividend. "You know you have companies with a solid cash flow and that have been around."

When markets are moving up and down again, it's a great time to sell call options, Mr. Lester says. (The transaction means Mr. Lester agrees to sell a set number of shares for an agreed-upon price up to a certain date, in return for a premium.)

Best move

Thanks to buying them on the cheap at $13 in the recession when shares were getting pummelled, Mr. Lester's shares in Cineplex are currently yielding him around 11 per cent. "I knew the company was worth a lot more," he says. "When people don't have [a lot of]money to go out for dinner, they still go to the movies, it's an-all cash business, and I love those cash-flow-positive companies."

Worst move

One of the investment strategies he's tried is buying calls, basically paying a premium to purchase a set number of shares of a company at a predetermined price. It worked with Apple. It worked with Research In Motion. So it made sense it would work with Google - except it didn't. "Right before earnings were announced I put a big bet on the stock rising, but it just didn't," he says. "It's what taught me to sell options rather than buy them."


"Really get to know your money. Read The Globe, read some books, and learn other people's strategies. Don't outsource the care of your money to others. If you use an adviser, participate in the decisions."

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