Founder liquidity planning
The tax clock on your stock started when the shares were issued, not when the banker sent a term sheet. Most of the work that still matters has to finish before you sign an LOI.
Last reviewed September 5, 2026. Figures below are federal, as of 2026.
Why the window closes at signing
Once a deal is binding, several of the highest-value moves are already gone. Gifts of stock, charitable transfers, domicile facts, and some entity clean-up cannot be unwound later without looking like you did them because of the sale. The work is sequencing: what has to be true in what quarter, with which adviser, before anyone is locked in.
Clexperus sits on the personal side of that calendar. Transaction counsel owns the purchase agreement. The CPA owns the return. We hold the picture that connects QSBS, trusts, state tax, and what happens to the proceeds after the wire clears.
What we do before a liquidity event
- Pull issuance records and map which QSBS regime each tranche sits in.
- Flag gifts, trust funding, and charitable transfers that must precede a binding agreement.
- Separate stock-sale economics from asset-sale economics so you are not surprised by ordinary income.
- Size cash for the actual tax bill, not a guess, then stage what stays liquid versus what can be invested.
- Coordinate banker, deal counsel, CPA, estate counsel, and the wealth plan so you are not the messenger.
How does the tiered QSBS exclusion work?
It depends on when the shares were issued. Stock issued on or before July 4, 2025 still needs a more-than-five-year hold for the 100% federal exclusion, a gross-asset ceiling of generally $50 million at issuance, and a per-issuer cap of the greater of $10 million or 10 times basis. Stock issued after July 4, 2025 follows OBBBA (P.L. 119-21): 50% exclusion after three years, 75% after four years, 100% after five years; a $75 million gross-asset ceiling at issuance; and a per-issuer cap of the greater of $15 million or 10 times basis. The $15 million cap and $75 million asset limit are indexed after 2026.
Which QSBS cap applies to my shares?
Issuance date is the split. Stock issued on or before July 4, 2025 uses the older $10 million (or 10 times basis) cap. Stock issued after July 4, 2025 uses $15 million or 10 times basis, whichever is greater. Mixed lots are common after a conversion or a later financing. Pull the stock ledger and the 83(b) files now, not in diligence week.
What tax planning should I do before I sign an LOI?
Start with entity and QSBS eligibility, then gifts and trust transfers that have to be old news before the deal is real, then domicile facts if state tax is material, then charitable transfers of low-basis stock. After that, model cash for tax and lockup. Counsel drafts. The CPA confirms basis and holding periods. We keep the order honest so a late idea does not blow up a closed window.
Can QSBS exclusions be stacked across trusts?
Non-grantor trusts can, in the right facts, each use a per-issuer cap. Transfers after the deal is in motion usually fail. State situs of the trust matters, and corporate counsel and estate counsel have to agree on the same facts. This is not a last-quarter project.
Does my state follow the federal QSBS exclusion?
Federal and state are separate questions. Several states have not conformed fully to Section 1202. A large federal exclusion with a large state bill is a common surprise. Domicile is evidence and timing, not a new address on a utility bill. Confirm current conformity with your CPA before you treat the federal number as the whole answer.
How should I invest proceeds after selling my company?
Cash for the tax bill first, sized to the actual return, not to a round number. Then staged deployment against real spending, concentrated leftover equity, and any lockup. Private markets can wait until the liquidity calendar is honest. See also financial planning for business owners and what a multi-family office actually does after the wire.
Educational only, not tax or legal advice. Coordinate with your CPA and counsel. Clexperus does not draft legal documents. Ask about relationship pricing if document preparation is in scope with outside counsel. Clexperus is a registered branch office of A.G.P./Alliance Global Partners. Figures: OBBBA P.L. 119-21; IRS Rev. Proc. 2025-32 for 2026 estate and gift amounts where cited elsewhere on this site.
Next steps
If a sale, recap, or secondary is on the calendar, the useful conversation is the order of work, not a product list.