Tax planning can be one of the most valuable steps a Canadian business owner takes before selling their company. In this episode, we explore why the timing of your tax strategy can make a difference of hundreds of thousands or even millions of dollars in net proceeds. Discover why waiting until a deal is underway can mean missing opportunities that require years of preparation, and how early planning can help you keep more of the wealth you have worked hard to build. Learn how the Lifetime Capital Gains Exemption, share ownership structures, family trusts, and corporate purification can influence the tax outcome of a business sale. We also examine the key differences between share sales and asset sales, the importance of modelling after-tax proceeds, and other considerations such as alternative minimum tax, capital gains reserves, and cross-border transactions. The episode highlights why working with experienced tax and legal advisers well before going to market can help business owners make informed decisions. Whether you are planning to sell in the next few years or simply want to prepare your business for a future exit, this episode offers practical insights into maximizing net proceeds and avoiding costly tax-planning oversights. Discover the key questions to ask your advisory team, the importance of starting early, and how a well-structured transaction can help protect your financial legacy.