The Truth About Real Estate Investing... for Canadians

Byron Darlison founded Rise Vision in 1992 in Toronto and ran it for 30 years without raising a dollar of outside equity. For 25 of those years, by his own admission, the business was unfocused, unpredictable, and running him. In year 25, he hired a Metronomics coach and installed a business operating system. In the 5 years that followed, profits went from break-even to 20% sustained net margins, his work week dropped from 60 hours to under 10, and the business grew to serve organizations in over 100 countries. In year 30, he sold Rise Vision for an 8-figure exit to a Taiwanese industrial display manufacturer, with no earn-out and no employment clause. His team still runs and grows the business today. He now coaches a small number of founders privately and serves as Mentorship Chair and Accelerator Coach at Entrepreneurs' Organization Toronto. In this conversation, we cover: Why 25 years of hard work without a system produced inconsistent results, and what changed in year 25 What a business operating system actually is, why most founders fail to self-implement one, and why a coach changes everything How Byron's team internalized the system to the point where the business self-corrected without him What made Rise Vision attractive enough to sell with no earn-out, no employment clause, and a premium multiple The owner's outcome framework: why most founders never ask what they actually want from their business Why the definition of strategy is the word no, and how narrowing to 1 core customer changed everything The founder's dilemma: why founders who solve every problem are the biggest bottleneck in their business What the great wealth transfer means for buyers and why many boomer-owned businesses are deeply undervalued Why Byron says entrepreneurship is less risky than employment, not more, if you are willing to do the work How AI has allowed Byron to run a 14-agent software development pipeline from his home, solo, at a fraction of traditional cost Byron's arc is one of the clearest illustrations of what TAFI is now built around: multiple paths to financial independence, and the discipline to pick one and execute it properly.

In this episode, Erwin Szeto sits down with former corporate CFO turned personal wealth strategist, Winnie Tsang, to unpack why so many Canadian real estate investors feel stuck—and what smarter, more resilient wealth planning actually looks like today. They dive into landlord challenges, diversification beyond property, leveraging the stock market, corporate‑owned life insurance, and how families can build long‑term financial security without sacrificing time, health, or peace of mind.

Mike Rosehart shares his real estate journey from buying his first student rental while in university to scaling hundreds of units across residential, hotels, and motels in Canada. We talk house hacking, leverage, market timing, selling at the peak, and why hotels and motel conversions offer massive opportunities today. A raw, numbers-driven conversation on what actually works in real estate investing.Listeners can connect with Mike at: 🔗Instagram - https://www.instagram.com/mikerosehart/

Discover how to sell a tenanted property in 2026! Investor and property manager Tim Hong joins host Erwin Szeto to break down market trends, new regulations, and practical strategies for selling with tenants in place. Get expert tips on maximizing your investment, navigating challenges, and making smart decisions in today’s real estate market.Plus, get a sneak peek into the upcoming FREE webinar: "How to Sell an Investment Property for Maximum ROI" on January 13th, 8 p.m. EST. 🔗Link to register: https://www.eventbrite.ca/e/how-to-sell-investment-property-for-maximum-roi-tickets-1976760405586?aff=podcast