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Insights, analysis, and updates from the AI agent economy. Browse by tag.
Audited by an Algorithm: What the IRS's New AI Governance Policy Means for Your Small Business
The IRS's February 2026 policy, IRM 10.24.1, formalizes how AI models — now running 126 active projects across six annual cycles — flag small business and self-employed returns for audit, requiring mandatory human review before any AI referral becomes an examination.
App Store External Purchase Links: The 2026 Accounting Guide for iOS Developers
US iOS developers can currently run external purchase links at 0% Apple commission while courts settle a replacement rate. This guide covers the bookkeeping fallout — the merchant-of-record shift, sales tax nexus, reconciling two 1099s, and Apple's 15-day transaction reporting rule.
Are AI Coding Subscriptions Tax Deductible? Section 162 vs. Section 174
Claude, GitHub Copilot, and Cursor subscriptions are fully deductible under IRC Section 162 as ordinary business expenses, while Section 174 R&D amortization only applies to labor and compute tied to genuine new product development — and the 2025 One Big Beautiful Bill Act restored immediate deduction for domestic R&E costs.
2026 HSA Contribution Limits: What Small Business Owners Need to Know
The IRS raised 2026 HSA limits to $4,400 self-only and $8,750 family (Revenue Procedure 2025-19). A small business owner's guide to the S-corp more-than-2% shareholder rules, the 35% comparability excise tax, cafeteria plan workarounds, and how to avoid excess-contribution penalties.
The White House's 2026 Fintech Executive Order: A Small Business Banking Guide
A May 19, 2026 executive order pushes banks and fintechs closer together, reviving the layered-partnership risks the 2024 Synapse collapse exposed — here's what small business owners should watch and do before the 90- and 180-day regulatory deadlines hit in August and November 2026.
Visa and Mastercard Just Tightened Chargeback Monitoring Again: What the 2026 VAMP Threshold Cut Means for Merchants
Visa lowered its VAMP excessive-merchant threshold from 2.2% to 1.5% on April 1, 2026, with fines of $8 per flagged transaction, and Mastercard's Excessive Chargeback Program still triggers at 100+ monthly chargebacks — here's how the ratio math catches small merchants off guard and how to bring it back under the line.
The USMCA Joint Review Started July 2026: A Small Business Guide to Tariff Risk
The USMCA's mandatory six-year joint review began July 1, 2026, giving the US, Mexico, and Canada until 2036 to decide whether to extend the agreement—small businesses claiming preferential tariff treatment should audit certificates of origin now, since a paperwork gap can be treated as customs fraud during heightened review-period scrutiny.
Toast vs. Square vs. Clover: Choosing the Right POS System for Your Restaurant or Retail Business in 2026
Toast charges roughly 2.99% + 15¢ per transaction, Clover about 2.3% + 10¢, and Square 2.4–2.6% + 15¢ — a side-by-side breakdown of POS pricing, hardware costs, and contract terms to help restaurant and retail owners pick the right system in 2026.
Timeshare and Vacation Ownership Accounting: Maintenance Fees, Special Assessments, and Reserve Funding
Maintenance fees, special assessments, and reserve funds need separate ledgers — commingling them is why timeshare and vacation ownership resorts end up issuing surprise assessments averaging $1,800 or more per owner when reserves run dry.
Substack Newsletter Taxes 2026: A Creator's Guide to Schedule C, 1099-Ks, and Quarterly Payments
Substack newsletter creators are self-employed under IRS rules, owe 15.3% self-employment tax on net profit via Schedule C, and receive a 1099-K only above $20,000 in gross payments and 200 transactions — though all income must be reported regardless.
The Subchapter V Bankruptcy Debt Limit in 2026: What Small Businesses Need to Know
In 2026 the Subchapter V small-business bankruptcy debt limit is $3,424,000, down from the pandemic-era $7.5 million ceiling that expired in June 2024 — a bill in Congress could restore the higher threshold for businesses currently locked out of the cheaper reorganization track.
Stripe Billing vs. Chargebee vs. Recurly: Choosing Your SaaS Subscription Platform
Stripe Billing suits developer-led SaaS teams under roughly $500K MRR, Chargebee fits non-engineers managing complex pricing above a monthly platform fee, and Recurly's ML-optimized dunning recovers 40-70% of failed payments versus about 15% with no intervention.