400 tagged with "Compliance"
Navigate regulatory compliance and maintain audit-ready financial records
The Interest-Free Loan That Isn't: How Section 7872 Imputes Interest on Family and Shareholder Loans
A below-market loan triggers Section 7872, which treats forgone interest as taxable income to the lender even when no cash changes hands. This guide covers the $10,000 and $100,000 de minimis exceptions, the gift tax connection, and how charging the AFR avoids the whole problem.
NIL Collectives and 501(c)(3) Status: What IRS Memorandum AM 2023-004 Means for Donors
IRS Memorandum AM 2023-004 holds that most nonprofit NIL collectives fail the 501(c)(3) operational test because compensating student-athletes is substantial private benefit, not charitable activity — meaning donor contributions are often not deductible.
Why Most NIL Collectives Aren't Real Charities (and Your Donation Isn't Deductible)
The IRS memorandum AM 2023-004 concluded that NIL collectives paying 80-100% of donations to athletes confer substantial private benefit and fail the operational test for 501(c)(3) status, so contributions to them are generally not tax-deductible.
The SBA 8(a) Program in 2026: A Survival Guide to Federal Set-Asides After the Ultima Reset
A practical guide to qualifying for the SBA 8(a) Business Development Program in 2026 — the $850,000 personal net worth, $400,000 three-year average AGI, and $6.5 million asset caps, the post-Ultima social disadvantage standard, $7M and $4.5M sole-source thresholds, and how to survive the nine-year graduation clock without losing certification.
Section 414 Controlled Group and Affiliated Service Group Rules: How Multiple Businesses Can Sabotage Your 401(k)
Section 414(b), (c), and (m) treat related businesses as one employer for retirement-plan testing. This guide explains controlled-group and affiliated-service-group rules, the spousal and minor-child attribution traps, and the steps multi-business owners should take before opening a 401(k).
Section 45E After SECURE 2.0: How Small Employers Recoup 100% of Pension Plan Startup Costs on Form 8881
SECURE 2.0 turned Section 45E into a 100% refund of pension plan startup costs—up to $5,000 per year for three years—for employers with 50 or fewer employees, stacked with a per-employee contribution credit worth up to $1,000 and a $500 auto-enrollment credit, all claimed on Form 8881.
Section 530 Safe Harbor: How Businesses Survive IRS Worker Reclassification Audits
Section 530 of the Revenue Act of 1978 blocks the IRS from assessing back payroll taxes on reclassified 1099 workers if a business proves reasonable basis, substantive consistency, and reporting consistency. Revenue Procedure 2025-10 now requires examiners to consider the relief first and sets 25% / 10-year thresholds for the industry-practice safe harbor.
Section 530 Safe Harbor: How to Avoid IRS Back Payroll Taxes on 1099 Workers
Section 530 of the Revenue Act of 1978 bars the IRS from collecting back employment taxes on misclassified contractors if a business met three tests—reporting consistency, substantive consistency, and a reasonable basis for treating the workers as 1099 contractors.
Section 6751(b) Supervisory Approval: The Procedural Defense That Can Erase IRS Penalties
Section 6751(b) requires a real IRS supervisor to personally approve penalties in writing before assessment. A working guide to using Chai, the Graev trilogy, and the December 2024 final regulations to defeat accuracy-related, fraud, and information-return penalties — which penalties qualify, what documents to demand, and how to raise the argument at Appeals before paying for Tax Court.
Section 7508A Disaster Tax Relief: How FEMA-Declared County Residents Get Postponed Deadlines, Coordinate With Form 4868, and Decide on a Prior-Year Casualty Loss
Section 7508A lets the IRS postpone almost any tax-related deadline by up to one year after a federally declared disaster. This guide explains who qualifies as an affected taxpayer, how postponement interacts with Form 4868, what happens to penalties already accruing, and when to elect a prior-year casualty loss under Section 165(i).
Section 7874 Anti-Inversion Rules: Why a Foreign Parent Does Not Always Mean a Foreign Tax Bill
Section 7874 treats a foreign parent as a U.S. corporation when former U.S. owners hold 80% or more, and penalizes inversion gain for 10 years at 60-80%. The substantial business activities safe harbor requires 25% of employees, assets, and income in the foreign country.
State Unclaimed Property and Escheat Reporting for Small Businesses: Dormancy Periods, Due Diligence Letters, and NAUPA Holder Reports
A practical guide for small businesses on identifying unclaimed property — uncashed vendor and payroll checks, customer credits, gift cards — applying state dormancy periods, mailing due diligence letters, and filing the NAUPA II holder report before Delaware or another state opens a contingency-fee audit.