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An IPO can detonate years of double-trigger RSUs into one tax year. The income stacks, the withholding falls short, and the bill arrives while the stock is still locked up.
Move to a no-tax state and your RSUs do not all become tax-free. The state where you worked while they vested can still tax that slice of the income.
An RSA is real stock you own at grant; an RSU is a promise of stock later. That one distinction decides whether you can file an 83(b), when you owe tax, and whether you vote your shares from day one.
The startup-equity cousin that works very differently for tax. A profits interest can be worth zero today and still hand you real upside later.
Exercise before vesting while the spread is tiny, file an 83(b), and you tax the gain now at a near-zero number instead of later at a big one. The risk is real cash on stock that can go to zero.
Move to a no-tax state and you still owe the old state on the part of the spread you earned there. The income follows the workdays, not your new address.
When the ESPP and your RSU tax bill compete for the same paycheck, one of them is a near-certain return and the other is a bill you already owe. That settles the order.
QSBS is a federal break, and states get a vote. California taxes the gain in full while New York generally follows the federal exclusion, so the same sale can split two ways.
California ignores the QSBS exclusion entirely. A gain the IRS lets you exclude in full is taxed at up to 13.3 percent by California, and the only real fix is residency, set up years before you sell.