Pre-Exit Planning
The Tax Moves That Expire the Day Your Deal Closes
March 29, 2026 • 2 min read
Most founders discover the best tax strategies after it's too late to use them. QSBS elections, charitable remainder trusts, installment sales — they all have windows that close at signing.
Most founders meet their wealth advisor after the wire hits. By then, the most powerful tax strategies are already off the table.
QSBS exclusions can eliminate up to $10 million per shareholder in federal capital gains — but only if the stock qualifies and the election was made years before the sale. Charitable remainder trusts funded with appreciated pre-exit stock can generate income for life while eliminating gains on the contributed shares — but the trust has to be established and funded before the transaction closes. Installment sales to intentionally defective grantor trusts can spread recognition across years and move future appreciation out of your estate — but the note structure has to be in place before the deal is signed.
These aren't obscure strategies. They're well-established tools that sophisticated tax counsel uses every day. The problem is timing. Your M&A attorney is focused on the deal. Your CPA is focused on the return. Nobody is sitting between them, mapping the tax implications of every deal term in real time.
That's what we do. We engage 12-24 months before a liquidity event and build the tax architecture around the deal — not after it. The structures we implement in that window routinely save founders more than the difference between a good deal and a great deal.
The math is simple: a founder selling $100M in stock without pre-exit planning might keep $60M after federal and state capital gains. With 18 months of preparation — QSBS elections, trust structures, installment sale mechanisms — that number can be $75M or more. That's a $15M difference. And it's entirely a function of when you start planning, not how good your lawyer is.
If you're 12+ months from a potential exit, this is the highest-ROI conversation you can have. If you're closer than that, some options are still available — but the menu gets shorter every month.