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#side-hustle

Side Hustle

Tax, accounting, and growth tips for side projects, freelancers, and part-time businesses

Getting Paid for Bug Bounties: How Your HackerOne and Bugcrowd Payouts Are Taxed

Bug bounty payouts from HackerOne and Bugcrowd are ordinary income from the first dollar, and for 2026 platforms only issue 1099s at $2,000 per researcher — but the income is taxable with or without a form. Covers W-9 setup, the hobby-versus-business test that decides whether tooling is deductible, self-employment tax, and quarterly estimates.

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.

Flea Market and Secondhand Vendor Bookkeeping: When Your Weekend Booth Becomes a Real Business

Flea market and secondhand vendors owe Schedule C income tax plus 15.3% self-employment tax once net earnings pass $400, and most states require a seller's permit or transient vendor license for regular booth sales. This guide covers the Section 183 hobby-vs-business test, per-item cost-basis records that survive an audit, the state sales tax permit patchwork, and the 2026 thresholds for Form 1099-K ($20,000 and 200 transactions) and Form 1099-NEC ($2,000).