#TaxLossHarvesting
Tax-loss harvesting is selling losing investments to offset capital gains taxes, then buying similar (but not identical) assets to maintain market exposure. Betterment and Wealthfront robo-advisors automated this, claiming to add 0.77% annual alpha through systematic harvesting. Wash sale rule prevents buying identical securities within 30 days. Most valuable in taxable brokerage accounts during bear markets when losses are plentiful. Bogleheads debate whether DIY or robo-advisor harvesting is worth the complexity.
Sources: Betterment TLH whitepaper, IRS Publication 550, Bogleheads wiki