He turned a $19K house flip into a $2 billion real estate empire and his stock is up more than 4000% since going public. In this episode of In the Money with Amber Kanwar , Amber sits down with Bob Dhillon, CEO of Mainstreet Equity, to unpack how he built one of Canada’s most successful small-cap real estate stories. 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. Timestamps 00:00 Show intro 02:20 How did Bob get the name Bob Dhillon? 03:20 Bob’s origin story 06:00 How Bob got to Canada and created Mainstreet Equity 10:15 Break 11:00 The core principles of Mainstreet Equity 13:00 Why western Canada? 14:30 The stats on Mainstreet Equity 17:30 Mainstreet’s macro thesis 19:00 Why Bob loves Winnipeg + did he ever think about moving to Ontario & Quebec? 20:30 Break 21:00 Are more investors looking at western Canada? Are policies working? 24:00 Thoughts on U.S. relations and the trade war 25:45 Bob’s real estate outlook 27:00 What’s happened to the entrepreneurial spirit? Why has Mainstreet not become a REIT? 29:30 Why Bob has never sold one share of Mainstreet Sponsors For over 25 years, Raymond James has been helping Canadians achieve their financial goals. Visit https:// raymondjames.ca today to discover how you can live a life well planned. With $62 billion in assets, ATB Financial is powering possibilities for more than 820,000 financial services clients in Alberta and beyond. Visit https://ATB.com/inthemoney for more information Over the last 45 years, Middlefield has helped Canadians build and preserve wealth through active management. Ask your financial advisor about Middlefield or learn more at https://middlefield.com today. Discover how The Murray Wealth Group can work for you by visiting https://MurrayWealthGroup.com. World Class Investing. Wealth built Together. Links https://inthemoneypod.com/ https://instagram.com/inthemoneypod https://facebook.com/profile.php?id=61569721774740 https://twitter.com/inthemoneypod https://tiktok.com/@inthemoneypod
[email protected] DISCLAIMERS The information provided in this podcast is for informational purposes only and does not constitute financial, investment, or professional advice.The views expressed by the host and guests are their own and do not necessarily reflect the opinions of any organization or company. The host and guests may maintain positions in any securities discussed on the podcast. Always consult with a qualified financial advisor or professional before making any investment decisions. In the Money delivers expert stock picks, actionable ideas, and timely money management tips. Hosted by business journalist Amber Kanwar, each episode features interviews with top portfolio managers who suggest ways to achieve good returns. Covering everything from ETFs and Canadian stocks to global investing trends, dividend strategies, and risk management, this show is made for DIY investors, stock market enthusiasts, and anyone looking to sharpen their financial strategy. Contact:
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