#equity-instruments
Understanding stock, SAFE notes, convertible notes, and startup financing structures
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.
A 409A valuation is the IRS-recognized appraisal that sets the strike price on every option grant. Without one, founders risk 20% federal excise penalties, premium interest, and California's 5% piggyback tax — all falling on the employee.
How founders use zeroed-out GRATs to transfer pre-IPO stock appreciation to heirs tax-free, leveraging the IRS Section 7520 hurdle rate while preserving the lifetime estate exemption.
Profits interests let LLCs grant equity to service providers tax-free under IRS Revenue Procedure 93-27. This guide covers the safe harbor's three conditions, the threshold value rule, Rev Proc 2001-43 vesting fix, and the self-employment tax tradeoff partners should expect.
ASC 718 requires startups to recognize the grant-date fair value of equity awards as compensation expense over the vesting period, even when no cash changes hands. This guide covers measurement, recognition, forfeitures, modifications, disclosures, and the audit pitfalls that derail funding rounds.
