Caitlin MacGregor, CEO and co-founder of Plum, was telling a story. She was describing how, in the first year of her company’s existence, she moved from New Hampshire with her husband and seven-month-old baby back into her mother’s house in Petrolia, Ont., to save money. She was in her early 30s. She and her husband, Neil, and their baby, would sleep on two mattresses in her brother’s childhood room. She thought it would be for three or four months. It turned out to be a year and a quarter.