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Compliance

Navigate regulatory compliance and maintain audit-ready financial records

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NIL Collectives and 501(c)(3) Status: What IRS Memorandum AM 2023-004 Means for Donors
·mike

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.

nonprofit
charitable-giving
tax-compliance
Why Most NIL Collectives Aren't Real Charities (and Your Donation Isn't Deductible)
·mike

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.

tax
charitable-giving
tax-deductions
The SBA 8(a) Program in 2026: A Survival Guide to Federal Set-Asides After the Ultima Reset
·mike

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.

sba
small-business
compliance
Section 414 Controlled Group and Affiliated Service Group Rules: How Multiple Businesses Can Sabotage Your 401(k)
·mike

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).

retirement-plans
solo-401k
tax-compliance
Section 45E After SECURE 2.0: How Small Employers Recoup 100% of Pension Plan Startup Costs on Form 8881
·mike

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.

tax-credits
retirement-plans
small-business
Section 530 Safe Harbor: How Businesses Survive IRS Worker Reclassification Audits
·mike

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.

tax-compliance
payroll
audit
Section 530 Safe Harbor: How to Avoid IRS Back Payroll Taxes on 1099 Workers
·mike

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.

tax
tax-compliance
payroll
Section 6751(b) Supervisory Approval: The Procedural Defense That Can Erase IRS Penalties
·mike

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.

tax
tax-compliance
compliance
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
·mike

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).

tax
tax-deadlines
tax-planning
Section 7874 Anti-Inversion Rules: Why a Foreign Parent Does Not Always Mean a Foreign Tax Bill
·mike

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.

tax
tax-compliance
business-acquisition
State Unclaimed Property and Escheat Reporting for Small Businesses: Dormancy Periods, Due Diligence Letters, and NAUPA Holder Reports
·mike

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.

small-business
compliance
audit
Texas Franchise Tax 2026: Filing the Public Information Report and Avoiding Forfeiture
·mike

Texas Franchise Tax 2026: Filing the Public Information Report and Avoiding Forfeiture

Texas raised the franchise tax no-tax-due threshold to $2.65 million for 2026 and 2027 reports, but LLCs and corporations still owe a Public Information Report by May 15. Missing it triggers forfeiture, personal liability for officers, and loss of access to Texas courts.

tax
tax-compliance
compliance
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