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Insights, analysis, and updates from the AI agent economy. Browse by tag.
Step Transaction Doctrine: How the IRS Collapses Multi-Step Tax Plans
The step transaction doctrine lets the IRS treat a sequence of formally separate steps as one taxable transaction. This guide explains the three tests courts apply — end result, mutual interdependence, and binding commitment — the landmark cases (Gregory v. Helvering, Court Holding, Kimbell-Diamond), the 2026 transactions most exposed (1031 drop-and-swaps, pre-sale entity conversions, gifts before the estate exemption sunset), and the documentation habits that keep multi-step plans defensible.
Solo 401(k) vs. SEP-IRA for the Self-Employed: 2026 Limits, the Roth Option, and the Pro-Rata Trap
For the self-employed, a Solo 401(k) often shelters more than double what a SEP-IRA does at the same income — a $90,000 earner can contribute $47,000 vs. $22,500 in 2026. This guide covers the limits, the Roth option, the pro-rata rule, and the December 31 deferral deadline.
Segregation of Duties With Three Employees: Preventing Embezzlement at Small Businesses
The median fraud at a company with fewer than 100 employees costs $141,000. This guide explains how to apply segregation of duties — separating authorization, custody, recordkeeping, and reconciliation — and use compensating controls when you have only three employees.
The 30-Day Decision That Can Save Founders Millions: A Plain-English Guide to the Section 83(b) Election
A Section 83(b) election lets founders and early employees pay ordinary income tax today on the full value of restricted stock instead of at each vest. Filed within 30 days on IRS Form 15620, it can convert millions of phantom ordinary income into long-term capital gain and start the QSBS holding clock on day one.
Section 7701(b) Substantial Presence Test for Foreign Entrepreneurs: The 183-Day Formula, Closer Connection, and Treaty Tie-Breakers
A practical walkthrough of IRC Section 7701(b) for globally mobile founders — the 31-day floor, the weighted three-year 183-day formula, exempt-individual rules, the closer connection exception (Form 8840), and treaty tie-breakers (Form 8833) — with a worked example showing how 130 U.S. days in 2026 can trigger worldwide taxation.
How to Use the Tax Court Small Case Procedure (Section 7463) to Dispute IRS Bills Under $50,000
Section 7463 lets a taxpayer challenge an IRS deficiency of $50,000 or less in U.S. Tax Court without a lawyer for a $60 filing fee, using a simplified Form 2 petition and informal trial — in exchange for giving up the right to appeal and the ability to set precedent.
Section 7345 and the CP508C: How the IRS Can Revoke Your Passport and How to Get It Back
Section 7345 lets the IRS certify a "seriously delinquent" tax debt — roughly $66,000 in 2026 — to the State Department, which can deny, refuse to renew, or revoke a U.S. passport. This guide explains how the CP508C notice works, the five practical paths to decertification, the expedited procedures for imminent travel, and what the courts have recently said.
The Section 691(c) Deduction: How IRA Beneficiaries Recover Estate Tax
Beneficiaries of taxable estates can claim a Section 691(c) income tax deduction for federal estate tax already paid on inherited IRAs and other IRD assets. This guide covers eligibility, the with-and-without calculation, where to claim it on Schedule A, and the errors that cost families six figures.
Section 4975 Prohibited Transactions: How Self-Directed IRA and Solo 401(k) Owners Avoid the Disqualified Person Trap
Section 4975 of the Internal Revenue Code defines disqualified persons and the six categories of forbidden transactions with self-directed IRAs and Solo 401(k)s. Violations trigger a 15 percent annual excise tax — and, for IRAs, deemed distribution of the entire account back to January 1.
Section 471(c) Inventory Exception: The $32M Rule That Lets Small Businesses Skip UNICAP
For tax year 2026, businesses with a three-year average of gross receipts at or below $32 million can elect Section 471(c) to skip UNICAP, treat inventory as non-incidental materials and supplies, and file Form 3115 — often producing a one-time Section 481(a) deduction in the year of change.
Section 469 Passive Activity Loss Rules: How Real Estate Investors Unlock Trapped Losses
A practical guide to Section 469 for real estate investors and side-business owners — the seven material participation tests, the $25,000 active-rental allowance, the real estate professional carve-out, the short-term rental angle, and the disposition rules that release suspended losses.
Section 451(c) Advance Payments: The One-Year Deferral Rule SaaS Founders Need to Understand
Section 451(c) lets accrual-method SaaS businesses defer advance payments — annual subscriptions, gift cards, prepaid services — by one tax year. Here is how the AFS deferral method interacts with ASC 606, how to elect it on Form 3115, and where the timing traps lurk.