The largest tax outcomes of your life are decided years before the exit. QSBS qualification, stacking, GRATs, and rollover planning all reward lead time and punish delay.
A founder's tax plan has a sequence. At incorporation: confirm QSBS qualification and file the 83(b) election. As the company appreciates: gift shares to non-grantor trusts while the valuation is low, so each trust's Section 1202 cap costs the least exemption. Ahead of a term sheet: GRATs and installment sales move remaining upside out of the estate. At exit: Section 1045 rollovers bridge any holding-period shortfall, and charitable structures absorb what the exclusions do not.
Run in order, this sequence routinely changes after-tax outcomes by eight figures on a large exit. Run late, most of it is unavailable: gifts price at the deal valuation, holding periods cannot be manufactured, and step-transaction risk constrains what can be done once a sale is in motion.
We work with founders from the first priced round onward, coordinating with your counsel and keeping the plan current as the company reprices.
Multiply the Section 1202 exclusion by gifting shares to non-grantor trusts, each with its own per-issuer cap.
Read the overview →Sold qualifying stock before the holding period was met? Roll the proceeds into new QSBS within 60 days and keep the clock running.
Read the overview →Transfer the upside of an appreciating asset at near-zero gift tax cost. The classic pre-liquidity estate freeze.
Read the overview →A separate taxpayer for income tax purposes. The building block behind QSBS stacking, state tax planning, and multi-generational compounding.
Read the overview →Sell appreciated assets inside a tax-exempt trust, defer the gain across a payout stream, and take a deduction up front.
Read the overview →A first meeting covers your situation, the strategies that plausibly apply, and what we would need to review before recommending anything.
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