A liquidity event turns paper equity into decisions you cannot undo on a whim. IPO unlocks, tender offers, secondaries, and large option exercises all create the same shape of year: more cash, more tax complexity, and a concentrated position that suddenly has a market.
This checklist is for that year. It is educational, not personalized advice. Use it to organize the work, then run the numbers with a qualified professional who sees your full household.
If you want the service view, see post-liquidity planning. For grant-level mechanics before cash hits, see the equity compensation advisor page and the hidden math of liquid tech equity.
1. Inventory what is becoming liquid
Write down every instrument that can create income or gains this year:
- RSUs vesting on the ordinary schedule
- ISOs or NSOs you may exercise
- Shares released from lockup
- Tender or secondary proceeds
- Any 83(b) or QSBS facts that still matter
For each line, note quantity, cost basis if known, expected date, and whether proceeds arrive as cash or shares. Incomplete inventories are how people miss a stacked W-2 and capital-gains year.
2. Build a tax map before the first big sale
Ask for a projection that includes:
- Ordinary income from NSO spreads, some tenders, and RSU vests
- Alternative minimum tax risk from ISO exercises
- Short-term vs long-term capital gains on share sales
- State taxes if you moved, split residency, or still file in a prior state
- Withholding already taken versus what you will actually owe
Employer withholding on supplemental wages is often 22% federally (37% above $1 million). If your real rate is higher, the gap is your problem to fund. The RSU tax calculator and RSU tax advisor pages cover the vest-side version of this gap. ISO holders should also read ISO AMT planning.
3. Set cash for taxes and the next 12 to 24 months
Before you redesign the portfolio, ring-fence cash for:
- Expected federal and state tax beyond withholding
- Quarterly estimates if this year jumps your income
- Near-term goals you do not want funded by a forced sale later
- A basic reserve so market moves do not dictate your next decision
Diversification works better when tax cash is already spoken for.
4. Pace diversification to lockups and concentration
A staggered lockup is a calendar, not a single payday. Match sales to:
- Unlock tranches you actually control
- Tax brackets across this year and next
- How much employer stock remains as a share of net worth
- Where sale proceeds will go so you are not swapping one tech bet for another identical one
If QSBS may apply, confirm eligibility and holding periods before you sell founder or early-employee stock. The QSBS exemption guide covers the mechanics.
5. Put tax and planning on the same team
Liquidity years break when a financial advisor recommends a sale schedule and a separate CPA only sees the result in March. The cost is not only two invoices. It is missed timing on estimates, AMT, and cash.
Nino puts a dedicated CPA and CFP on one flat-fee membership so equity, taxes, and cash share one model. Read tax and financial advisor for the coordination problem, and flat-fee CFP and CPA for the pricing model.
6. Book the work while the window is open
If you are deciding now, book a demo. Through August 31, 2026, new members who start a one-year membership get $500 off their first year. Every plan includes a 30-day money-back guarantee.
Bring your unlock schedule, grant summary, and a rough sense of other 2026 income. The useful consult output is a clearer tax and cash map, whether or not you join.
