chapter fourteen

14 Tax-Loss Harvesting: Improving after-tax returns

 

This chapter covers

  • The basics of tax-loss harvesting - what it is, and the potential benefits
  • The “wash sale” rule and its implications on tax-loss harvesting
  • Implementing a tax-loss harvesting system for ETFs

Investors hold assets that are expected to increase in value over time. However, the increases are never straight lines - there are always downturns along the way. As a result, investors will sometimes hold assets at a loss. Tax-loss harvesting (TLH) is the process of selectively selling assets currently trading at a loss. Selling depreciated assets creates realized losses which can then be used to offset realized gains or ordinary income. The proceeds from the sales of depreciated assets can be reinvested in similar (but not identical!) assets to maintain the investor’s desired exposures.

TLH is a fairly common feature among robo-advisors - half of the robo-advisors surveyed in Chapter 1 include TLH as a feature. This chapter explains the mechanics and benefits of TLH and shows what an implementation using ETFs might look like.

14.1 The economics of tax-loss harvesting

Tax-loss harvesting benefits investors in two ways:

  1. Delaying tax payments from the present to the future - known as tax deferral
  2. Achieving a lower tax rate on realized gains or income

Both benefits are important, and the differences can be somewhat subtle. Let’s go into some more detail on each.

14.1.1 Tax deferral

14.1.2 Rate conversion

14.1.3 When harvesting doesn’t help

14.2 The wash-sale rule

14.2.1 Wash sale basics

14.2.2 Wash sales with Python

14.3 Deciding when to harvest

14.3.1 Trading costs

14.3.2 Opportunity cost

14.3.3 End-to-end evaluation

14.4 Testing a TLH strategy

14.4.1 Backtester modifications

14.4.2 Choosing ETFs

14.5 Summary