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Two business owners sold nearly identical companies for $3 million each. One paid $800,000 in tax. The other paid close to zero in tax. In this video, I break down the 5 tax mistakes that caused an $800K gap — and one deal that fell apart entirely because nobody planned ahead. In this episode, we cover: How treating tax as an afterthought can cost you hundreds of thousands Why failing to qualify for the $1.25M Lifetime Capital Gains Exemption can cost $334,000 How one simple “purification” step could have preserved the exemption How estate freezes and family trusts can multiply exemptions across family members Why waiting until a buyer is at the table limits your options The real reason some deals die during due diligence Why your accountant (even a good one) may not be enough for a sale 💡 The biggest tax savings in a business sale happen before the deal — not after it closes. If you’re planning an exit, model your numbers, clean up your company, and build the right advisory team before going to market. Links: 🔗 Download the Pre-Sale Tax Checklist: https://theadvisorstable.com/800k-tax... 🔗 Instagram: / advisorstablepodcast 🔗 LinkedIn: / the-advisors-table-podcast 📞 Looking for Trusted Tax Advice? Connect with Sankalp (Sunny) Jaggi, at Cedar Consulting Group 📧 Email: sunny@cedargroup.ca 🌐 Website: https://www.cedargroup.ca/ 🔔 Subscribe for deeper breakdowns on deal tax strategy, exemptions, estate freezes, and how to structure your exit properly. 👇 Comment below: Are you planning to sell in the next few years? Have you modeled your after-tax number yet? *LEGAL DISCLAIMER:* This video is based on a real case, but names and some details have been changed to protect client confidentiality. This content is for educational purposes only and does not constitute legal or tax advice. Always consult with a qualified tax professional before making financial decisions. 00:00 – $3M Sale, $800K Tax Difference 00:31 – The $3M Deal: What David Missed 01:13 – Mistake #1: Treating Tax as an Afterthought 02:17 – Mistake #2: Losing the $1.25M Exemption ($334K Cost) 04:18 – Multiplying the Exemption with Family (Estate Freeze) 06:02 – $800K Completely Avoidable 06:11 – The Deal That Completely Died 07:28 – Mistake #4: When Tax Kills the Deal 07:40 – Mistake #5: Wrong People Leading the Deal 09:29 – What To Do Before Selling (1–3 Years Out) 10:31 – Build the Right Deal Team 10:46 – Free Pre-Sale Tax Checklist