Bob explains why mid-market, value-add apartments in Western Canada remain his competitive edge, how buying buildings at a fraction of replacement cost created long-term upside, and why he doubled down during downturns instead of retreating. He also shares how immigration shaped his entrepreneurial path, why he’s never sold a single share of Mainstreet, and what he sees as the future for housing affordability in Canada.
Over 25 years, Dhillon has grown Mainstreet to 18,600+ rental units with $270M in revenue, while delivering 14 straight quarters of double-digit returns. He reveals why he resisted the REIT model, why Toronto and Ontario didn’t fit his strategy, and how Western Canada’s overlooked markets provided him with runway others ignored.
Whether you’re an investor looking at small-cap opportunities, interested in real estate cycles, or curious about how one entrepreneur built a $2B empire from the trunk of his car, this episode is packed with insights on long-term conviction, value creation, and compounding returns.
