A startup RSU is a promise to hand over shares later, and "later" needs a second key: an IPO, a tender the company blesses, or an acquisition. That single detail decides whether your equity is a house, a small cheque, or nothing.
Every private RSU that has time-vested is sitting in front of the same fork. There is no fourth door, and on Carta you cannot sell your way out of it — Carta keeps the records and administers tenders; it is not a market.
↔ swipe the diagram sideways
On Carta you see the grant and the vesting bar. Settlement, tax withholding and any tender are events the company runs through Carta — not buttons you press.
The whole time-vested pile is ordinary income at once, valued at that day's price. Withholding is a flat 22% federal (37% only above $1M), which is below what a high earner actually owes.
Same instrument, wildly different outcomes — and the difference was almost never the employee's effort.
Listed in June 2026 at $135/share. One ex-employee's 6,500 shares ≈ $880k; ~4,400 employees became millionaires on paper.
The lockup was staggered from August 2026, so shares unlock in tranches over months — you sell into a schedule, not a cliff.
No IPO for 15 years. Instead: annual tenders — $91.5B in Feb 2025, $159B in the 2026 letter.
Stripe waives the liquidity trigger each round, so vested RSUs settle and get taxed whether or not you sell. And grants reportedly expire ~7 years after issue — 2019–20 grants were the ones racing the clock.
IPO priced at $78 in Nov 2021. By lockup expiry the stock closed $28.79 — more than 60% below IPO, 80% off the peak.
Tax was fixed at settlement value while the shares kept falling. That is the lockup trap: you can owe tax on money the market took back.
The two broker paths share the same Singapore tax analysis. They diverge in exactly four places: custody, the form you get, the US dividend and estate-tax tail, and the days and basis points between a share and SGD in your bank.
Block 01 · the tax spine
IRAS taxes the gain when your beneficial interest vests: at grant if the award carries no vesting, at vesting if there is no selling restriction, and on the date a real selling restriction lifts. For a double-trigger RSU that lands on the day the shares are actually delivered — that last mapping is a reading of the guidance, not an IRAS sentence.A lock-up, or shares nobody will buy, does not push the tax date back. The vesting bar on Carta is not the tax clock.
Gain = open market value on that date minus what you paid, usually zero. It is Singapore employment income under s10(1)(b), pulled in by the deeming rule s10(6). Your employer reports it on IR8A item d7 plus Appendix 8B, through AIS by 1 March.No PAYE for resident employees. The tax arrives as a bill you pay the following year, not a deduction off your payslip.
Granted while you were employed in Singapore → the full amount is Singapore income, even if you vest or exercise abroad. Granted before you joined → not Singapore income at all, wherever you are when it vests.A vesting period split across two countries does not split the taxable amount. Nothing here is pro-rated.
Singapore has no general capital gains tax. A one-off sale of shares already taxed at vest is capital in the ordinary case; badges of trade — flipping repeatedly, buying to resell, funding trades with borrowed money — are the only route back to a tax bill.The vest-date tax is final for that gain. What the sale can still cost you is a second characterisation, if your behaviour reads like a business.
When a foreign employee ceases Singapore employment, unvested awards are taxed on a deemed exercise basis under s10(7), and the employer must hold your monies until tax clearance is issued. If the real gain comes in lower, s10(7AA) allows a revision within 5 years.Your final payslip can be held against a number computed from a valuation, not from a sale.
IRAS ruled in Advance Ruling 01/2022 that a plan letting you sell only back to the company or to a designated vehicle did not defer tax — the gain was taxed when the shares were acquired, at paper value, with no market. Only a genuine moratorium moves the date. Read the plan document, not the summary of it.
Block 02 · two employees, same grant
Same tax engine on both sides. Only custody, the form you get, the US dividend and estate-tax tail, and the friction between the share and SGD differ — which is why these are one decision, not two stories.
Biggest gotcha: a Singapore broker does not withhold Singapore tax. Proximity is not withholding. The assessment lands the year after delivery; the shares were sellable long before. If the price fell in between, you still owe on the delivery-date value.
Biggest gotcha: the broker did not create the estate-tax exposure — the issuer's place of incorporation did. Moving the shares to a Singapore broker does not remove it, and a Cayman issuer never had it.
Block 03 · the payoff
Block 04 · three gotchas
None of this replaces the five lines in your grant doc further up — settlement mechanics sit on top of the plan terms, not instead of them.
For scale: roughly 62% of seed-stage companies are gone within seven years. A double-trigger RSU at a company that never has an exit is worth exactly zero — quietly, with no tax event to remind you.
These five lines decide your outcome more than the valuation on the term sheet does.