The five-year exit plan may seem like a smart strategy for Canadian business owners who believe they can earn more by continuing to operate their companies rather than selling today. This podcast explores why the “run it five more years” mindset can cost owners millions in potential wealth. Through a real-world-style manufacturing business example, discover why a company’s EBITDA is not the same as cash in your pocket and why the value of a business today may outweigh years of future earnings. Learn about the six key financial and operational factors that challenge the five-year exit strategy, including tax implications, the Lifetime Capital Gains Exemption, the time value of money, business continuity risks, dividend tax misconceptions, and the personal cost of remaining at the helm. The discussion also explains why buyers are willing to pay multiples for businesses and how future earnings, growth opportunities, synergies, and risk tolerance influence a company’s valuation. Whether you are preparing to sell your business, planning your retirement, or considering succession options, this podcast will help you evaluate your exit timeline with greater clarity. Discover the critical questions to ask before deciding to hold on or sell, and understand how thoughtful exit planning can help protect the wealth you have built and support your long-term financial goals.