Benj Gallander lives and invests against the grain


This stock-market iconoclast outperforms the pros

Benj Gallander - Guru

Contra the Heard Picks

returned 52.3% last year

By Peter Boisseau

If all the world’s a stage, then Benj Gallander is one of the stock market’s greatest characters.

He so abhors watches he asked his girlfriend to get rid of hers. “I don’t want to know the time that badly.” He doesn’t carry a cell-phone. “I don’t want to be that accessible.” His dress code is more Main Street than Bay Street. “I like the freedom of being able to wear what I want.”

But when your stock picks return over 50% in one year and you still have the good sense to get out before the crash, he figures you’ve earned the right.

And anyway, the playwright/investor with an MBA and half-dozen theatrical credits fits right in at the artists’ co-op where he lives in Toronto. Many of his friends don’t know about his life as a financial expert, unless he pops up on the news talking shop.

The jeans and T-shirt approach also fits the proudly contrarian philosophy of Mr. Gallander’s books and
Contra the Heard investment newsletter, whose subscribers include many brokers and financial analysts.

His latest book,
The Uncommon Investor, continues that tradition of going against the grain, while allowing Mr. Gallander to indulge his creative bent with a cast of characters who discuss investing while watching a mythical World Series game between the Toronto Blue Jays and New York Mets.

The book, which hit the stores Tuesday, ridicules old standards such as buy and hold investing, dollar-cost averaging and borrowing to buy on margin. At the same time, he pitches a philosophy he calls “anti-investing”.

“The smartest thing a lot of people can do is pay off their credit card debts, and when they have the cash on hand, then look at the stock market. But not before."