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#independent-contractor

Independent Contractor

Contractor payments, 1099 tracking, and compliance

The New AI Side Hustle: Bookkeeping and Quarterly Taxes for RLHF and Data-Labeling Gig Income

AI data-labeling and RLHF gig income arrives with nothing withheld, so annotators owe 15.3 percent self-employment tax plus income tax on every payout and must pay quarterly estimates by the 2026 deadlines. This guide covers the 1099-NEC and 1099-K thresholds, the 90/100/110 percent safe-harbor rules, Schedule C deductions most annotators skip, and a 20-minute-a-month bookkeeping system for multi-platform payouts.

How to Run a Bar Crawl Company: Ticket Revenue, Venue Splits, Guide Pay, and Permits

A bar crawl company sells admission, not alcohol, so it usually needs no liquor license, but a $25 ticket can lose over $3.60 to platform and processing fees before a single guide is paid. Here is how to structure written per-head venue deals, book pass-through covers as liabilities instead of revenue, defer advance ticket sales until the event, clear city pub-crawl permits, carry $1–2 million in liability coverage, and decide whether guides are W-2 employees or 1099 contractors.

New-Hire Reporting: The 20-Day Rule Every First-Time and Multistate Employer Must Know

Every U.S. employer must report each new hire and qualifying rehire to a State Directory of New Hires within 20 days of the first day of paid work, and electronic filers may batch reports 12 to 16 days apart. This guide covers the six required data points, the one-state designation that lets multistate employers file to a single directory, California and New York independent-contractor reporting rules, and the federal penalty cap of $25 per unreported employee rising to $500 for collusion.