Trading quantitative models in a self-directed brokerage account creates a unique friction point: the disconnect between strategy-level iteration tracking and tax-level compliance. When operating algorithms like my Augmented Income Strategy (AIS), Standard Deviation Dips (SDS), or purchases triggered by Dollar-Cost Averaging (DCA) where losses are obvious on previous iterations at higher prices, individual trade iterations are naturally executed across various price tiers. Over time, high-basis legacy lots can act as "capital anchors" locking up cash in stagnant positions while the rest of the engine actively cycles realized gains. Harvesting losses on those legacy lots is a disciplined, well-planned move to free up capital velocity and offset taxable income. However, if your automated system triggers a buy signal on that same ticker within 30 days, the IRS Wash-Sale Rule kicks in... disallowing the tax deduction and adding the lost basis back into your new position. Her...
Systems, Iron, and Yield: Periodical logs on programmatic trading, augmented infrastructure income, and the discipline of a structured life by an algorithmic quant Trader.
A periodical by Michael Medeiros