42 tagged with "Equity Instruments"
Understanding stock, SAFE notes, convertible notes, and startup financing structures
Section 368 Tax-Free Reorganizations: How Type A Mergers, Type B Stock Swaps, and Type C Asset Deals Defer Tax in Strategic M&A
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) Explained: A Five-Year Tax Deferral for Private-Company RSUs and NSOs
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 Golden Parachute Payments: The 3× Trigger, 20% Excise Tax, and the Private Company Cleansing Vote
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.
Section 4501 Stock Buyback Excise Tax in 2026: Computing the 1% Tax, Netting Issuances, and Filing Form 7208
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 QSBS Rollover: How Founders Defer Capital Gains by Reinvesting Within 60 Days
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.
Phantom Stock and SARs: How Private Companies Reward Key Employees With Synthetic Equity Without Diluting the Cap Table
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.
409A Valuations: A Founder's Guide to Stock Option Strike Prices and Safe Harbors
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.
Grantor Retained Annuity Trust (GRAT): The Wealth Transfer Strategy Founders Use to Move Appreciating Stock Tax-Free
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 Under Rev Proc 93-27: A Guide to Tax-Free LLC Equity Grants
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 Stock-Based Compensation Accounting for Startups: A Practical Guide
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.
SAFE vs Convertible Note: A Founder's Guide to Choosing the Right Early-Stage Financing
A SAFE is a contract granting future equity with no maturity or interest, while a convertible note is a loan with 4–8% interest and an 18–24 month maturity that becomes due if no priced round closes — and Y Combinator's 2018 post-money SAFE locks each investor's ownership at Investment ÷ Cap, dilution that hits founders, not prior SAFE holders.
ESPP Tax Treatment: Qualified vs. Disqualifying Dispositions Explained
How qualified versus disqualifying dispositions change the tax bill on a Section 423 ESPP, with worked examples covering ordinary income, adjusted basis, Form 3922 cost-basis fixes, and a decision framework for when holding two years actually pays off.