#executive-compensation

Executive Compensation

Nonqualified deferred compensation, SERPs, equity awards, Section 409A compliance, and other strategies for compensating senior executives and key employees

30 postsView all tags Back to All Posts

July 27, 20269 min read

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.

Mike Thrift

insuranceemployee-benefitsexecutive-compensation

May 23, 202617 min read

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.

Mike Thrift

equity-instrumentstaxtax-planning

May 17, 202610 min read

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.

Mike Thrift

taxtax-creditstax-deductions

May 16, 202613 min read

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.

Mike Thrift

taxtax-complianceexecutive-compensation

May 15, 202614 min read

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.

Mike Thrift

nonprofittax-complianceexecutive-compensation

May 14, 202611 min read

Section 457(b) and 457(f) Deferred Compensation Plans: How Nonprofit, Government, and School Employees Stack Pre-Tax Savings on Top of a 403(b) or 401(k)

A detailed 2026 guide to Section 457(b) and 457(f) deferred compensation plans — how public-sector and nonprofit employees can stack a 457(b) on top of a 403(b) or 401(k) for up to $65,000 in deferrals, when the special three-year catch-up reaches $49,000, and how 457(f) vesting can trigger a tax bomb under Section 409A.

Mike Thrift

retirement-plansretirement-savingstax-planning

May 14, 202612 min read

Section 457(b) and 457(f) Deferred Compensation Plans: Stacking Pre-Tax Savings on a 403(b) or 401(k)

A 2026 guide to Section 457(b) and 457(f) plans — how public-sector and nonprofit employees can defer up to $49,000 pre-tax by stacking a 457(b) on a 403(b), and how nonprofit executives use 457(f) without triggering the substantial-risk-of-forfeiture tax trap.

Mike Thrift

retirement-plansretirement-savingstax-planning

May 14, 202613 min read

Section 4960: The 21% Excise Tax on Nonprofit Executive Pay After OBBBA's 2026 Expansion

Section 4960 imposes a 21% excise tax when a tax-exempt organization pays a covered employee more than $1 million. The 2025 OBBBA expansion redefines "covered employee" as anyone employed since 2017, widening the tax base for hospitals, universities, and foundations filing Form 4720 in 2026.

Mike Thrift

taxtax-compliancenonprofit

May 14, 202614 min read

Section 83(i) Tax Deferral on Private Company Stock: A Five-Year Lifeline for Pre-IPO Employees with RSUs and NSOs

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.

Mike Thrift

taxtax-planningequity

May 13, 202613 min read

The ISO AMT Trap in 2026: How Tech Employees Get Hit With Six-Figure Tax Bills on Stock They Can't Sell

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.

Mike Thrift

taxtax-planningequity-instruments

May 13, 202613 min read

ISO AMT in 2026: Bargain Element, Form 6251 Line 2i, and the OBBBA Phase-Out Cliff

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.

Mike Thrift

equity-instrumentstax-planningstock-basis

May 13, 202614 min read

Section 1259 Constructive Sales: How Hedging Appreciated Stock Can Trigger a Phantom Tax Bill

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.

Mike Thrift

tax-planningcapital-gainsequity-instruments

Start Free→Documentation