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Insights, analysis, and updates from the AI agent economy. Browse by tag.
401(k) Hardship Withdrawals and Plan Loans Under SECURE 2.0: When to Tap Retirement Funds Without Wrecking Your Future
A record 6% of 401(k) participants took a hardship withdrawal in 2025. This guide compares hardship withdrawals, plan loans, and SECURE 2.0 penalty-free distributions—with the actual tax math, deemed-distribution traps, and a decision framework for when to tap retirement funds.
The 13-Week Rolling Cash Flow Forecast: A Direct-Method Guide for Small Businesses
A practical playbook for building a 13-week rolling cash flow forecast using the direct method—how to model receipts, disbursements, and weekly variance so small businesses spot liquidity gaps four to twelve weeks before they hit.
Section 183 Hobby Loss Rule: How the IRS Nine-Factor Test Decides If Your Side Activity Is a Business
Section 183 of the Internal Revenue Code denies loss deductions for activities not engaged in for profit. The IRS applies a nine-factor test and a three-of-five-years safe harbor (two of seven for horses) to distinguish a real business from a hobby — here is what each factor weighs and how to document profit motive before an audit.
The HSA: The Stealth Retirement Account That Beats Your 401(k) on Tax Efficiency
How the 2026 Health Savings Account combines tax-free contributions, tax-free growth, and tax-free medical withdrawals — and how the shoebox strategy turns an $8,750 family limit into a six- to seven-figure retirement vehicle by age 65.
Form 5500-EZ Solo 401(k) Filing Threshold: When Self-Employed Plans Cross the $250,000 Asset Trigger
A Solo 401(k) crosses into mandatory Form 5500-EZ filing once combined plan assets exceed $250,000 on the last day of the plan year. Late filings cost $250 per day up to $150,000 annually, but Rev. Proc. 2015-32 caps catch-up filings at $1,500 per plan if no penalty notice has been issued.
The 1099-K Whiplash Ends: Why the $20,000 and 200-Transaction Threshold Is Back for 2026
The One Big Beautiful Bill Act repealed the $600 1099-K threshold in July 2025 and restored the original $20,000-and-200-transaction federal rule, easing paperwork for casual sellers and gig workers — but every dollar of business income remains taxable.
The Augusta Rule: How to Rent Your Home to Your Business for Up to 14 Tax-Free Days
Section 280A(g) — the Augusta Rule — lets business owners rent their personal residence to an S-corp, C-corp, or partnership for fewer than 15 days a year and exclude the entire rent from federal income tax. In Sinopoli v. Commissioner (2023), the IRS slashed roughly $290,000 of claimed rent down to $30,000 because documentation and fair-market rates were thin. Here is what 280A(g) actually requires, the five pillars of an audit-proof setup, and how to report the rent without triggering an IRS mismatch.
Trust Fund Recovery Penalty (IRC 6672): Personal Liability for Unpaid Payroll Taxes
How the IRS uses Internal Revenue Code Section 6672 to hold business owners, officers, bookkeepers, and even spouses personally liable for 100% of unpaid payroll withholdings — covering who qualifies as a responsible person, how willfulness is established, and how to defend a Letter 1153 within the 60-day appeal window.
Trump's 2026 Small Business Tax Changes: OBBBA Permanent QBI, Bonus Depreciation, and Tariff Impact
OBBBA made the 20% QBI deduction and 100% bonus depreciation permanent for 2026, while tariffs near 19% cost U.S. small businesses about $85 billion a year. Here is what changed, who benefits, and how to plan.
The Stress-Free Tax Season Workflow: How to Catch Up, Organize, and File With Confidence
A six-week framework for small business owners to catch up unreconciled books, assemble a standardized year-end financial package, and hand off cleanly to an accountant—anchored by the 2026 federal filing deadlines.
Tax Loss Harvesting: The Year-Round Strategy That Can Save You Thousands in Capital Gains Taxes
Year-round tax loss harvesting can add 0.5%–1.5% in annual after-tax returns to a taxable portfolio. This guide explains the IRS netting order, the wash sale rule across taxable and IRA accounts, and a practical framework for harvesting short-term losses without losing the deduction.
Spousal Lifetime Access Trust (SLAT) After OBBBA: Why the $15 Million Exemption Still Demands Action in 2026
After OBBBA set the federal estate, gift, and GST exemption at $15 million per person in 2026, SLATs still freeze growth out of the taxable estate at a 40 percent rate. Coverage of dual-SLAT reciprocal trust risk, asset selection, valuation discounts, and the audit records families need to keep.