Tax Loss Harvesting (Part 1 of How to Reduce Your Tax Bill like the Big Boys)

In the interest of saving time, a course of in-depth lesson breakdowns will come a bit later. In the meantime, we’ve attached a few articles to help out as an introduction to something most of you have never heard of. WARNING: this stuff is boring as hell… but if you truly want to get a better grasp on the types of things that separate the wealthy from the middle class, this is a must. You probably also don’t want to get an IRS bill saying you owe for something you didn’t know about. Note that Real Estate Tax Strategy is vastly more complicated and will come at a later time.

Now is a perfect time of year to learn the difference between Short Term vs. Long Term Capital Gains and FIFO vs LIFO (first in, first out vs. last In, first out) if you’re new. **Be EXTRA sure to read carefully about wash sales.** More investors get screwed over by these rules than anything else this time of year. Simply put, you can’t just sell something for a capital loss just for the tax benefit and then buy it right back within a month.

Quick Overview on Capital Gains

Short Term vs Long Term Capital Gains

Understanding Tax Lots (TD)

Tax Loss Harvesting (TD)

5 Tax Loss Harvesting Considerations (Fidelity)

How to Avoid Violating Wash Sale Rules

Taxes on Dividends

Basic Capital Gains Tax Calculator