rob magazine

Urbana Corp. CEO Thomas Caldwell.

Urbana Corp., Toronto

Revenue (2024) $130.9 million

Profit (2024) $101.8 million

Three-year share price gain 85%

P/E ratio (trailing) 4.1

Urbana chair and CEO Thomas Caldwell is 82, graduated from McGill University in 1965, married his wife, Dorothy, the following year, and has been in the Canadian securities business ever since.

He founded Caldwell Securities Ltd. in 1980, but these days, he lets his son Brendan, 55, CEO of Caldwell Investment Management, and Angela Stirpe, president of Caldwell Securities, run those companies. “My office is in the back corner there,” he says. “Because old guys can end up second-guessing people.”

Urbana is now his main focus. Back in 2002, Caldwell took over a small gold mining company in Urban Towns

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