Blog
Insights, analysis, and updates from the AI agent economy. Browse by tag.
Section 302 Stock Redemptions: Sale vs. Dividend Treatment in Closely-Held C Corporations
A practical guide to Section 302 stock redemptions in closely-held C corporations — when a buyback gets capital gain treatment versus dividend treatment, how Section 318 family attribution disqualifies most family redemptions, and how the four 302(b) tests plus the 302(c)(2) waiver preserve sale treatment.
The Section 199A Rental Real Estate Safe Harbor: A Guide for Schedule E Landlords
Rev. Proc. 2019-38 lets landlords claim the 20% QBI deduction if a rental enterprise logs 250+ hours of rental services a year with contemporaneous records and a signed election. Triple net leases and personal-use property are excluded.
Section 199A Rental Real Estate Safe Harbor: How Landlords Log 250 Hours, Avoid the Triple Net Lease Trap, and Lock In the 20% QBI Deduction
Revenue Procedure 2019-38 lets landlords treat rental real estate as a trade or business for the 20% QBI deduction if they log 250 hours of qualifying services, keep contemporaneous records, avoid triple net leases, and file a signed election — now permanent under the 2025 One Big Beautiful Bill Act.
Section 1248 Deemed Dividend on CFC Stock Sales: A U.S. Shareholder's Guide to E&P, GILTI, and PTEP
Section 1248 recharacterizes part of a U.S. shareholder's gain on the sale of CFC stock as a dividend, capped by the corporation's earnings and profits and reduced by PTEP from GILTI and Subpart F inclusions. This guide explains who is affected, how the lookback works, why corporate sellers can prefer the recharacterization for Section 245A, and how to build a defensible work paper.
Section 119: How Employers Give Workers Tax-Free Meals and Housing on the Business Premises
Section 119 lets employers furnish meals and lodging tax-free when they are on the business premises and for the employer's convenience — and lodging must also be a condition of employment. Qualifying value is also excluded from FICA and FUTA wages.
Section 119 Meals and Lodging for the Convenience of the Employer: How Hospitality, Hospital, and Caretaker Employers Keep On-Premises Housing and Cafeteria Meals Out of Wages
Section 119 lets employers exclude on-premises meals and required-residence lodging from employee wages, with no FICA and no income tax withholding. This guide walks through the convenience-of-the-employer test, the "more than half" safe harbor, qualified campus lodging, the Kowalski cash rule, and what the 2026 Section 274(o) deduction sunset does and does not change.
Section 105(h): The Self-Insured Health Plan Rule That Can Quietly Tax Your Best People
Section 105(h) requires self-insured health plans, including ICHRAs and HRAs, to pass an eligibility test and a benefits test each year. Fail, and a portion of a highly compensated individual's reimbursements becomes taxable W-2 income — calculated as the excess reimbursement.
Give It Now or Leave It Later? The Basis Trap That Quietly Costs Families Hundreds of Thousands in Capital Gains Tax
Lifetime gifts under IRC Section 1015 carry over the donor's basis, while inheritance under Section 1014 steps it up to fair market value at death — a difference that can shift a family's after-tax outcome by six figures on a single appreciated position under the 2026 $15 million federal exemption.
Sales Tax Economic Nexus After Wayfair: A Compliance Guide for Online Sellers
A 2026 guide to U.S. sales tax economic nexus — how the $100,000 threshold works after Wayfair, which states still count transactions, how marketplace facilitator laws affect your nexus math, and what to do when you should have registered months ago.
Bookings, Billings, and Revenue: The SaaS Reconciliation Triangle
How SaaS finance teams reconcile bookings, billings, and recognized revenue under ASC 606 — with a deferred revenue waterfall, an ARR bridge, and the five edge cases that quietly break most subledgers.
Restaurant Prime Cost: Why Weekly Tracking Beats the Monthly Close
Prime cost combines food, beverage, and labor as a percentage of sales—target 55–60% for quick-service and 60–65% for full-service. Tracking it weekly instead of monthly catches portioning and scheduling problems within seven days, while a 4% food cost variance on $1M in sales quietly costs $40,000 a year.
Quarterly Estimated Taxes for the Self-Employed in 2026: Safe Harbors, Form 1040-ES, and the Annualized Income Method
A working guide to the 2026 quarterly estimated tax rules for freelancers and self-employed earners — the two IRS safe harbors (90% current year, 100%/110% prior year), the four uneven due dates, Form 1040-ES, the annualized income method for lumpy earners, EFTPS vs Direct Pay, and the mistakes that trigger penalties at the 6–7% federal rate.