What "pre-liquidity" planning means
Pre-liquidity planning is the work you do in the window before a sale, recapitalization, or IPO — while the highest-value tax and estate strategies are still available. Once a deal is under a letter of intent, most of them disappear. Timing, not effort, is what determines how much you keep.
36 months out — foundation
- Clarify your goals and your after-tax "number."
- Confirm your entity structure and evaluate QSBS eligibility (this can start a holding-period clock).
- Assemble your team: fee-only fiduciary advisor, M&A attorney, CPA, and banker.
Section 1202 changed materially in July 2025, and the rules now depend on when the stock was issued. Stock issued after 4 July 2025 follows a tiered exclusion — 50% at a three-year hold, 75% at four years, 100% at five or more — with a per-issuer cap of the greater of $15 million or ten times adjusted basis, and a gross-asset ceiling of $75 million at issuance. Stock issued on or before that date keeps the prior rules: a full five-year hold for any exclusion, a cap of the greater of $10 million or ten times basis, and a $50 million ceiling. Exchanging older stock for newly issued shares does not change which rules apply. A company that issued shares across that date may have shareholders facing different outcomes at the same exit. Eligibility also turns on requirements many businesses do not meet — the issuer must be a domestic C corporation, stock must be acquired at original issuance, and professional services, financial services and hospitality are excluded regardless of size. This is an area where the details decide the outcome, and it requires review by a CPA or tax attorney who works in it specifically.
24 months out — structure & estate
- Gift appreciated equity into trusts while the valuation is still lower.
- Consider grantor trusts and QSBS "stacking" across family members.
- Update the business valuation to support gifting.
12 months out — tax positioning
- Model asset-sale vs. stock-sale outcomes with your CPA.
- Design charitable vehicles (CRT/DAF) to be funded before any LOI.
- Review residency/domicile (Florida's no-income-tax advantage) and insurance/liability coverage.
90 days out — execution readiness
- Finalize charitable funding before the letter of intent (to avoid anticipatory assignment of income).
- Set a cash-reserve plan and a post-sale investment policy.
- Put sudden-wealth guardrails in place.
The day after — concentration to diversification
Once the wire clears, the job shifts to investing the proceeds thoughtfully and tax-efficiently. If you took part of the deal in acquirer stock, our concentrated-stock guide covers the unwind. For the full picture, see our pillar guide on financial planning before selling your business.
Disclosure: Skyview Financial Group, LLC is an SEC-registered investment adviser (CRD #310581). This content is educational only and is not individualized tax, legal, or investment advice. Figures and rules cited are current as of August 2026 and subject to change; please consult your CPA and, where applicable, legal counsel. Examples are illustrative and do not reflect any specific client.