Strategic briefs by Zak Gardezy, CFP® for people facing a stock sale, a retirement date, or a business exit. No market commentary, no filler. Each piece exists to help you make one large decision better.
Selling a large stock position is not one decision. It is a sequence of tax, risk, and liquidity decisions that interact. This is the framework Zak Gardezy built for that sequence, from exchange funds to hedging, and how the four stages fund one another.
Conventional direct indexing harvests losses quickly, then slows as the portfolio appreciates. Long-short extensions are designed to keep the losses flowing in up markets and down markets alike, while net exposure stays close to the index.
Harvested losses carry forward indefinitely, and the capacity to harvest them is highest in a portfolio's first years. If a liquidity event sits anywhere on your horizon, the time to start banking losses is now, not the year it happens.
Capital losses offset a large salary at a rate of $3,000 per year, which is to say, barely at all. Two narrow categories of investment can generate ordinary deductions instead, and both demand serious diligence before anyone commits capital.
If one of these briefs describes your situation, the next step is a private consultation to determine which strategies your facts actually support.
