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Insights, analysis, and updates from the AI agent economy. Browse by tag.

Collecting W-9s and Avoiding 24% Backup Withholding: A Vendor-Onboarding Playbook for 1099 Compliance
·mike

Collecting W-9s and Avoiding 24% Backup Withholding: A Vendor-Onboarding Playbook for 1099 Compliance

A practical vendor-onboarding playbook for collecting W-9s, passing IRS TIN matching, handling CP2100 and B notices, and avoiding 24% backup withholding and 1099 penalties in 2026.

tax-compliance
small-business
bookkeeping
Accounting for Customer Loyalty Rewards Programs: ASC 606 Points Liability, Deferred Revenue, and Breakage
·mike

Accounting for Customer Loyalty Rewards Programs: ASC 606 Points Liability, Deferred Revenue, and Breakage

Under ASC 606, loyalty points are a separate performance obligation — part of each sale is allocated to a deferred revenue liability using standalone selling prices, recognized when points are redeemed, with unredeemed value booked as breakage in proportion to redemptions. This guide walks through the journal entries, the proportional vs. remote breakage methods, the chart of accounts, and the state escheatment rules that can block breakage income.

revenue-recognition
small-business
liability
Beancount MCP: Connect Your Ledger to Claude, Cursor, and Any AI Assistant
·mike

Beancount MCP: Connect Your Ledger to Claude, Cursor, and Any AI Assistant

The Beancount MCP server connects your plain-text ledger to Claude, Cursor, Windsurf, and any MCP-compatible AI client over OAuth 2.1 — ask questions, run BQL queries, and commit ledger edits without leaving your AI tool.

ai
llm
automation
Beancount.io's Ask AI Can Now Write Entries and Read Receipts
·mike

Beancount.io's Ask AI Can Now Write Entries and Read Receipts

Beancount.io expanded its Ask AI assistant from a read-only Q&A tool into an action-capable agent that drafts and writes ledger entries, reads uploaded receipts and bank-statement screenshots, and commits nothing without explicit user approval — live at /agent.

ai
llm
automation
Passing Credit Card Fees to Customers: Surcharges, Cash Discounts, and Dual Pricing in 2026
·mike

Passing Credit Card Fees to Customers: Surcharges, Cash Discounts, and Dual Pricing in 2026

Surcharging, cash discounts, and dual pricing are the three legal ways to pass card fees to customers in 2026—surcharges cap at 3% (Visa) and are banned in CT, ME, and MA, while cash discounts and dual pricing are legal in all 50 states and skip the 30-day network notice.

payments
small-business
compliance
Buy Now, Pay Later Is Quietly Breaking Your Books: A Merchant's Guide to Accounting for Klarna, Affirm, and Afterpay
·mike

Buy Now, Pay Later Is Quietly Breaking Your Books: A Merchant's Guide to Accounting for Klarna, Affirm, and Afterpay

BNPL providers pay merchants the full sale price minus a fee, then report gross volume on a 1099-K — so recording only the net deposit understates revenue and triggers IRS underreporter notices. Record gross sales through per-provider clearing accounts to keep fees, reserves, and 1099-K totals reconciled.

e-commerce
payments
revenue-recognition
Cash vs. Accrual Accounting: How to Choose the Right Method (and When the IRS Forces Your Hand)
·mike

Cash vs. Accrual Accounting: How to Choose the Right Method (and When the IRS Forces Your Hand)

Cash accounting records revenue when money is received and expenses when paid; accrual accounting records revenue when earned and expenses when incurred. IRS Section 448 mandates the accrual method once a business's three-year average gross receipts exceed the $32 million threshold for 2026, and changing methods later requires Form 3115 plus a Section 481(a) adjustment.

accounting-basics
accrual-accounting
revenue-recognition
State Tax Residency Audit Defense After Moving to a No-Tax State
·mike

State Tax Residency Audit Defense After Moving to a No-Tax State

A practical guide to surviving California FTB and New York residency audits after moving to Florida, Texas, or Nevada — the domicile and statutory residency tests, day-count documentation, equity compensation traps, and the convenience-of-the-employer rule.

tax
tax-compliance
audit
The Short-Term Rental Loophole in 2026: How W-2 Earners Offset Income with Material Participation and 100% Bonus Depreciation
·mike

The Short-Term Rental Loophole in 2026: How W-2 Earners Offset Income with Material Participation and 100% Bonus Depreciation

A walkthrough of the Section 469 seven-day rule, the three realistic material participation tests, and how the One Big Beautiful Bill Act's permanent 100% bonus depreciation lets short-term rental owners offset W-2 income — plus the bookkeeping habits that survive an IRS audit.

real-estate
tax-planning
bonus-depreciation
Bookkeeping for Independent House Cleaners and Solo Maid Services: A Practical 2026 Guide
·mike

Bookkeeping for Independent House Cleaners and Solo Maid Services: A Practical 2026 Guide

A 2026 bookkeeping playbook for solo and small residential cleaning operators — ASC 606 deferred revenue on recurring plans, OBBBA tip deductions up to $25,000, W-2 vs 1099 ABC-test pitfalls, care/custody/control insurance, and the KPIs that predict retention.

bookkeeping
small-business
self-employment
Cryptocurrency Miner, Staking Validator, and DeFi Yield Farmer Bookkeeping: The 2026 Tax and Recordkeeping Guide
·mike

Cryptocurrency Miner, Staking Validator, and DeFi Yield Farmer Bookkeeping: The 2026 Tax and Recordkeeping Guide

A practical 2026 guide for independent crypto miners, Ethereum validators, and DeFi liquidity providers covering entity selection, Form 1099-DA basis reporting, Rev. Rul. 2023-14, OBBBA Section 174 R&D expensing, FBAR/Form 8938 thresholds, and KPI tracking.

cryptocurrency
crypto-bookkeeping
defi
Yacht Broker and Marine Service Yard Bookkeeping: ASC 606 Commissions, Trust Accounts, and Travel Lift Depreciation
·mike

Yacht Broker and Marine Service Yard Bookkeeping: ASC 606 Commissions, Trust Accounts, and Travel Lift Depreciation

Yacht brokerages recognize commissions at closing under ASC 606, segregate deposits in Chapter 326 trust accounts, and depreciate travel lifts with Section 179 — and the service yard runs on technician utilization, parts margin, and slip occupancy KPIs.

bookkeeping
accounting
revenue-recognition
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