Bringing tax counsel in at signing is like calling the surgeon after the operation, you can clean up, but you can’t unmake the cuts. And yet it’s the fastest way we see deals die or prices inflate by 30%.

The pattern is depressingly consistent on both sides of the table. Week 1, the LOI is signed and everyone’s optimistic. Week 4, diligence surfaces a historical reorganization that didn’t qualify for the rollover everyone assumed, or an unreported s. 84.1 issue, or passive investment income disqualifying the small business deduction. Week 6, price renegotiation begins. Indemnities expand, escrows balloon, trust erodes. Week 8, the deal closes at a worse number, or doesn’t close at all.

Early tax integration changes the math. A pre-LOI structuring memo weighs share vs. asset, hybrid, butterfly, or amalgamation before the price is locked.

Sell-side vendor due diligence cleans the tax house before buyers arrive almost always surfacing more value than it costs. Tax-efficient earn-outs and rollovers under s. 85, 85.1, and 86 preserve deferral. Cross-border planning addresses withholding and treaty positions before they become deal points. Purchase price allocation under s. 68 moves real money. And tax indemnities, when drafted properly, are anchored in actual exposure rather than boilerplate.

If a sale is eminent, or even in the foreseeable future, it’s always a good idea to reach out and have a conversation with a tax lawyer about the health of your business and whether it’s ready for the transaction.

Have questions? Reach out!