Tax-loss harvesting still works
Realize losses in taxable accounts to offset realized gains dollar-for-dollar. Excess losses up to $3K/yr offset ordinary income; the rest carries forward indefinitely. The wash sale rule (30 days) is the main trap.
Why holding 1 year and 1 day matters
Short-term gains tax at ordinary rates (10–37%). Long-term at 0/15/20%. On a $50K gain, the difference between 35% ST and 15% LT is $10,000. Set calendar reminders for cost-basis lots.
QSBS exclusion (Section 1202)
Founders of C-corps held >5 years can exclude up to $10M or 10× basis in capital gains — federal tax = $0. State varies (CA, PA don't recognize). One of the most valuable tax provisions for startup employees.
Related guides
Long-form playbooks on the same topic, written by the RevenueLab editorial team.
State of Side Income 2026: Real Net Hourly Pay, Breakeven, and Tax Across 15 Side Hustles
Our annual report on side income in 2026 — gross vs net hourly pay for 15 paths, startup cost and breakeven timing, six-month income and quit rates, and what side income really costs in tax. Free to cite.
Read the guideLong-Form vs Shorts in 2026: A Channel-by-Channel Revenue Strategy
The actual per-view payout gap (often 50–200×), why Shorts-only channels plateau at $2–8K/month, and the four channel archetypes that win when they pick a primary format and stick with it.
Read the guideYouTube Creator Tax Guide 2026: 1099-NEC, Self-Employment, and the 24% Withholding Trap
How AdSense reports your income, why non-US creators get 24% withheld until they file a W-8BEN, quarterly estimated tax math for US creators, and the deductions most channels under-claim.
Read the guideFAQ
Does NIIT apply to all gains?
Yes — both ST and LT capital gains count as 'net investment income' when AGI exceeds $200K (single) or $250K (MFJ). The 3.8% is on top of regular tax.
Can I avoid state cap gains tax by moving?
Only if you establish full residency before the gain is realized. Stock options/RSUs vested in CA generally remain CA-taxable even after a move. Sale of a privately held company has more flexibility — talk to a CPA.
What about crypto?
Crypto is treated as property — same LT/ST distinction applies. Every swap (BTC → ETH) is a taxable event. Track basis lot-by-lot or pay the wash-sale-rule penalty (note: wash sale doesn't currently apply to crypto, an open loophole).
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