#equity-instruments
Understanding stock, SAFE notes, convertible notes, and startup financing structures
Section 83(i) lets qualified employees of qualified private companies defer federal income tax on RSU settlements and NSO exercises for up to five years. The 80 percent grant rule, mandatory escrow, and 30-day election deadline explain why adoption stays in the single digits — and when the election still pays off.
Exercising and holding ISOs adds the bargain element to AMTI on Form 6251 Line 2i, which can produce a six-figure tax bill before a single share is sold. A 2026 guide to the tightened AMT exemption phase-out ($500K single / $1M MFJ at 50¢ per dollar), the qualifying disposition rules under IRC §422, and the planning moves — AMT crossover exercise, §83(b) early exercise, same-year disqualifying sale, and multi-year laddering — that keep tech employees out of the trap.
Under OBBBA, the 2026 AMT exemption phases out at $500K single / $1M joint with a 50-cent rate, doubling the stealth bracket on ISO exercises. Here is exactly how the bargain element flows into Form 6251 line 2i, when a same-year disqualifying disposition eliminates the AMT adjustment, and how to plan exercises to avoid a six-figure phantom-income tax bill.
Section 1244 lets eligible founders and early investors convert up to $50,000 ($100,000 joint) of capital loss on failed C-corporation stock into ordinary loss deductible against W-2 wages, freelance income, or interest. This guide covers who qualifies, the $1 million capital ceiling, Form 4797 reporting, and the formation steps that keep the deduction defensible.
Section 1259 treats short-against-the-box trades, equity swaps, and tight collars on appreciated stock as constructive sales — taxable today, even with no proceeds. Covers the variable prepaid forward workaround, the 30-day closing exception, and the related-party trap.
Section 351 lets founders incorporate without immediate tax only if the transferor group owns 80% of voting power and every non-voting class right after the exchange. Miss the control test, contribute services instead of property, or assume liabilities greater than basis, and the gain surfaces anyway. A practical playbook covering boot, the Section 357(c) trap, basis carryover under Sections 358 and 362, and how to preserve QSBS eligibility under Section 1202.
Section 368 defines seven reorganization types (A through G) that defer corporate and shareholder tax in M&A. This guide covers the 40% Continuity of Interest test, Type A statutory mergers, Type B stock-for-stock swaps with the 80% control requirement, Type C asset deals, and forward/reverse triangular merger structures with their consideration limits.
Section 83(i) lets qualified rank-and-file employees at eligible private companies defer federal income tax on RSU vests and NSO exercises for up to five years, but FICA is still due at vesting, the 30-day election window is unforgiving, and the 80 percent broad-based grant rule keeps most startups from offering it.
Section 280G disallows the corporate deduction and imposes a 20% Section 4999 excise tax once parachute payments to a disqualified individual reach three times the executive's five-year average W-2 compensation, with the penalty applying to everything above 1× the base amount. Private companies can eliminate the consequences entirely through a 75% disinterested shareholder vote paired with conditional waivers signed before closing.
How publicly traded U.S. corporations compute the 1% Section 4501 stock buyback excise tax in 2026, apply the netting rule, claim statutory exceptions, and file Form 7208 — including what the November 2025 final regulations changed and where Form 720-X refund opportunities apply.
Section 1045 lets non-corporate taxpayers defer capital gains from a QSBS sale by reinvesting proceeds into new qualifying small business stock within 60 days. After the 2025 OBBBA expansion (75M gross assets cap, tiered 50/75/100 percent exclusion at 3/4/5 years), the rollover can convert a missed Section 1202 exclusion into a deferred, and potentially excluded, gain.
A practical guide to phantom stock and SARs for private companies — how the plans work, why Section 409A's 20% penalty is the rule that breaks most informal arrangements, how ASC 718 liability accounting affects EBITDA, and when synthetic equity beats options, RSUs, or an ESOP.
