Blog
Insights, analysis, and updates from the AI agent economy. Browse by tag.
Regulation D Rule 506(b) vs Rule 506(c): How Founders Pick Between the Quiet Round and the Public Pitch in 2026
Rule 506(b) and Rule 506(c) of Regulation D both allow uncapped private placements but differ sharply on marketing and verification. 506(b) bans general solicitation and permits up to 35 sophisticated non-accredited investors on a reasonable-belief standard; 506(c) permits public solicitation but requires reasonable steps to verify every purchaser is accredited. A March 2025 SEC no-action letter lets issuers rely on $200,000+ individual or $1 million+ entity minimum checks as the primary verification step.
Pooled Employer Plans (PEPs): How Small Businesses Share a 401(k) and Cut Costs Under SECURE Act 2.0
Pooled Employer Plans let unrelated small businesses share a single 401(k) under SECURE Act 2.0, cutting all-in fees from roughly 0.80% to 0.35% and shifting plan-document, investment, and Form 5500 duties to a Pooled Plan Provider while leaving employers with a narrow duty to prudently select and monitor the PPP.
Personal Holding Company Tax Under Section 541: The 20% Surtax That Quietly Ambushes Closely-Held C Corporations
Section 541 layers a 20% federal surtax on closely-held C corporations that fail both the stock ownership and 60% passive income tests. This guide walks through Schedule PH mechanics, the dividends-paid deduction, and four ways — cash, throwback, consent, and deficiency dividends — to zero out the tax before it hits.
Personal Goodwill in M&A Asset Sales: How Martin Ice Cream and Norwalk Help Owners Avoid Double Taxation
Personal goodwill, anchored in the Martin Ice Cream and Norwalk Tax Court decisions, lets closely held C corporation owners shift a portion of an asset-sale price out of the corporate tax layer and onto the shareholder as long-term capital gain. This guide explains the doctrine, when it works, the documentation that survives an IRS audit, and the mistakes that have sunk allocations.
Personal Goodwill in C-Corp Asset Sales: Martin Ice Cream, Norwalk, Bross Trucking, and Howard
Personal goodwill carve-outs let C-corporation shareholders pay 23.8% capital gains instead of 40%+ combined tax on a portion of an asset sale. Martin Ice Cream, Norwalk, and Bross Trucking show when the allocation survives; Howard shows when an employment-and-noncompete agreement quietly destroys it.
PEO vs CPEO vs ASO vs EOR: 2026 Small Business HR Outsourcing Guide
How small businesses should choose between a PEO, CPEO, ASO, or EOR—covering co-employment mechanics, the FICA wage base restart trap that doubles Social Security tax on a mid-year switch, joint-employer lawsuits under the FLSA and Title VII, and the contract terms to verify before signing.
The $141,000 Wound: How Small Businesses Catch Occupational Fraud Before It Ends Them
How small businesses can detect and deter occupational fraud — using the ACFE fraud triangle, segregation of duties, surprise audits, management review, and proactive data monitoring — with a 90-day plan tailored to a 20-person organization.
The NIL Tax Trap: What College Athletes (and Their Parents) Owe on Endorsement, Collective, and Revenue-Sharing Income
How NIL endorsements, collective payouts, and House v. NCAA revenue sharing are taxed in 2026—Schedule C mechanics, the 15.3% self-employment tax, multi-state jock-tax filings, and the planning moves that keep April manageable for college athletes and their families.
The Mega Backdoor Roth Playbook: How High Earners Can Funnel an Extra $47,500 Into Tax-Free Retirement Accounts in 2026
The mega backdoor Roth routes up to $47,500 of after-tax 401(k) contributions into a Roth bucket for 2026, on top of the standard $24,500 employee deferral, by converting after-tax dollars through an in-plan Roth conversion or in-service distribution to a Roth IRA. The IRS Section 415(c) total cap of $72,000 ($80,000 if age 50+) covers contributions from all sources combined, and converting promptly keeps the taxable earnings drag near zero.
Loan Covenants for Small Business Borrowers: How DSCR, FCCR, and Tangible Net Worth Decide When a Performing Loan Can Be Called
Loan covenants—DSCR, fixed charge coverage, tangible net worth, and leverage limits—can put a small business borrower in default while every payment is current. A practical breakdown of affirmative, negative, and financial covenants, cure periods, waiver requests, and what to negotiate before signing a credit agreement.
HSA vs FSA vs HRA in 2026: The Practical Playbook for Picking, Stacking, and Not Forfeiting Your Health Dollars
A 2026 walk-through of HSA, FSA, and HRA rules with the new contribution limits, the limited-purpose FSA stack that adds up to $7,800 of pre-tax room, and how small employers can use ICHRA and QSEHRA to compete with corporate benefits.
HSA vs FSA vs HRA in 2026: Stack a Limited-Purpose FSA With Your HSA and Beat the Use-It-or-Lose-It Trap
2026 rules for HSAs, FSAs, and HRAs — contribution limits, who owns each account, when each one wins, how to stack a Limited-Purpose FSA with an HSA without breaking eligibility, and how employees and employers avoid forfeitures.