Took the Company Plane on Vacation? How SIFL Values Personal Flights on Business Aircraft
IRS SIFL rules value personal flights on company jets at cents per mile, not charter cost — H2 2026 rates, control-employee multiples, W-2 reporting.
#executive-compensation
Executive Compensation
Nonqualified deferred compensation, SERPs, equity awards, Section 409A compliance, and other strategies for compensating senior executives and key employees
Why Your Bonus Check Gets a Flat 22 Percent Withheld
The IRS lets employers withhold a flat 22% on bonuses up to $1M and 37% above it. That's withholding, not your tax rate; the gap settles when you file.
Rabbi Trust vs. Secular Trust: Who Really Gets Your Deferred Compensation If the Company Fails?
A rabbi trust defers tax but leaves the employee behind your creditors in bankruptcy; a secular trust is IRS-taxed at funding. Pick by who bears credit risk.
What Startup Employees Should Know Before Selling Stock in a 2026 Tender Offer
A tender offer's ISO disqualifying-disposition income lands on your W-2 with no federal withholding — plan US estimated taxes before the window closes.
RSUs Explained for Startup Employees: Why Vesting, Not Selling, Is the Tax Event
RSUs are taxed as ordinary income on the vesting date, not at sale, and employers withhold a flat 22% on supplemental wages up to $1 million — leaving employees in the 32–37% brackets short by 10 to 15 percentage points each April. This guide covers double-trigger vesting at private startups, why no 83(b) election exists for RSUs, and the $0 cost-basis error on Form 1099-B that makes people pay tax twice on the same income.
Phantom Stock Plans for Small Businesses: Reward Key Employees Without Giving Away Ownership
A phantom stock plan grants key employees hypothetical units that track company value and settle in cash — no shares issued, no dilution, no voting rights. Payouts are ordinary income subject to FICA when paid, the employer deducts them in the same year, and cash-settled awards are liability awards remeasured at fair value each reporting period. Paying within 2½ months after the year units vest satisfies Section 409A's short-term deferral exemption; a two-to-three-participant plan typically costs $4,000–$10,000 to launch.
The 2026 AMT Cliff: Lower Phaseout Thresholds, Twice the Clawback
For 2026 the OBBBA resets AMT phaseout thresholds to $500,000 single and $1,000,000 joint and doubles the exemption clawback from 25 to 50 cents per dollar, so the same income that owed no AMT in 2025 can owe five figures next year. A guide to who is exposed, how to estimate your position, and five planning moves before year-end.
Split-Dollar Life Insurance, Explained: How Business Owners and Key Employees Share the Cost of a Policy
Split-dollar life insurance is an agreement — not a policy type — for an employer and a key employee to divide the premiums, cash value, and death benefit of one permanent policy. This guide compares the two structures (collateral assignment vs. endorsement), explains how the IRS taxes each under the economic benefit and loan regimes, why premiums are never deductible, and how to book the arrangement correctly from day one.
ISO vs. NSO Stock Options: A Startup Employee's Tax Guide to AMT, 83(b), Early Exercise, and the $100K Limit
A practical tax playbook for startup employees holding ISOs or NSOs — covering AMT exposure via Form 6251 line 2i, the 30-day Section 83(b) deadline, the two-year-and-one-year qualifying disposition rule, the $100,000 first-exercisable ISO cap, and the 1099-B cost basis error that causes double taxation.
Section 1341 and the Claim of Right Doctrine: Recovering Tax on Clawed-Back Bonuses
Section 1341 lets a taxpayer who repays more than $3,000 of previously taxed income recover the tax cost—via a deduction or a credit, whichever is lower—on the repayment-year return rather than by amending the old one.
Section 409A: Structuring Bonuses, Severance, and Phantom Equity to Avoid the 20% Penalty
Section 409A taxes noncompliant deferred compensation in the year of vesting and adds a flat 20% federal penalty plus interest. This guide explains the short-term deferral and separation pay exceptions, the six recognized payout triggers, the six-month delay for specified employees, and how to structure bonuses, severance, RSUs, phantom stock, and discounted stock options so founders avoid the penalty.
Section 4958 Intermediate Sanctions: How Nonprofit Boards Avoid 25% and 200% Excise Taxes on Excess Benefit Transactions
Section 4958 imposes 25% and 200% excise taxes on excess benefit transactions between public charities and disqualified persons, with a 10% manager tax on knowing approvers. Following three procedural steps creates a rebuttable presumption of reasonableness that shifts the burden of proof to the IRS.