CRA Trap Of Excess Corporate Cash
How poor tax planning can turn a $3 million business sale into an $800,000 tax problem – and why the biggest deal-saving strategies happen years before a buyer every appears.
Show Notes
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 solo, Sunny breaks down the 5 tax mistakes that caused an $800K gap – and one deal that fell apart entirely because nobody planned ahead.
In This Solo, 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.
📥 Resources from this episode
Pre-Sale Tax Checklist
The Advisors TablePre-Sale Tax Checklist
The tax planning steps every business owner should complete 1–3 years before going to market — base-case modelling, optimization gap, structure cleanup, and the strategies that turn an $800K tax bill into something materially smaller. Same workflow used internally with private clients.
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Need more than a podcast? Cedar Group handles tax planning, restructuring, and sale-readiness advisory for founders.
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