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By tax concept
83(b) & elections
RSUs
Restricted stock
How restricted stock is taxed (and how 83(b) flips it)
Restricted stock is taxed as ordinary income as it vests, unless you file an 83(b) and flip the whole thing to capital gains. That one form is the difference between a tax bill on tomorrow's value and one on today's, and it quietly starts the clocks that decide your rate years later.
How to file an 83(b) election, step by step
The letter, the 30-day clock, the line-by-line fields, and the proof you keep, in one checklist. Filing 83(b) is simple, but it is unforgiving, so the order of operations matters.
Should you file an 83(b) election? The decision and the breakeven
For early-stage stock worth almost nothing, filing the 83(b) is close to a no-brainer. It only gets hard once the shares carry real value and the tax you prepay stops being a rounding error. The breakeven is the price where prepaying finally beats waiting.
Missing the 30-day 83(b) deadline (and skipping it on purpose)
The 83(b) election has a hard 30-day window and no late forgiveness. Miss it, or skip it, on early-stage stock and you can hand the IRS a tax bill that grows every year the company does well, on shares you cannot sell to pay it.
A founder's restricted stock, start to exit
Follow one founder's restricted stock from incorporation to acquisition, and watch how a single form filed in week one decides what the exit actually pays. The tax fork happens at the beginning, not the end.
RSAs vs RSUs: the differences that actually matter
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.
Profits interests vs equity at an LLC
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.
2026 update on filing the 83(b) election
The current filing and proof rules for an 83(b) election, including the IRS's official Form 15620. The 30-day clock has not budged.
Case study: the missed 83(b) that cost six figures
An early hire skipped the form, then vested into a unicorn valuation. The tax bill arrived years before any chance to sell.
ISOs
NSOs
NSO exercise strategy: when to exercise, hold or sell, and the moves around it
The one lever an NSO hands you is the calendar. This is the whole playbook: when to exercise, whether to hold or sell, how to spread it, how to fund the tax, and how to give the shares away.
Early-exercising NSOs and the 83(b) election
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.
QSBS
Case study: a founder's QSBS exit, mostly tax-free
Five years held, the qualified small business stock exclusion claimed, and a large chunk of the gain off the table. The win was set up at incorporation, not at the sale.
Planning around QSBS: setup, stacking, and the 1045 rollover
The QSBS exclusion is mostly decided at the moment you get the stock, not the moment you sell. This is the planning playbook: lock in qualification early, multiply the cap with gifts and trusts, and use a Section 1045 rollover to rescue a forced early exit.