A collar combines two options on your existing position. You buy a put option that sets a floor, protecting you if the stock drops below a certain price. You sell a call option that caps upside. Done correctly, the call premium offsets the cost of the put, making the strategy cashless. You remain invested. No shares sold. No tax event triggered. But if the stock drops 30%, your losses are capped.

The most painful words in finance are "I should have sold." A structured sale is the antidote. Predetermined triggers, a target price, portfolio concentration thresholds, and time-based schedules all execute automatically. The market goes up and you're tempted to hold for more. The market goes down and you're afraid to lock in a loss. A structured plan executes regardless of how you feel that week.

Securities-based lending lets you borrow against your existing portfolio as collateral. The stock stays intact. No shares sold. No capital gains triggered. Interest rates are typically comparable to a home equity line of credit. Particularly valuable during blackout periods or when you want to defer a tax event to a future year when your income may be lower.

An exchange fund lets you contribute your concentrated stock and receive a diversified interest in a pool of assets contributed by other investors. No stock is sold. No immediate capital gains tax triggered. You contribute your shares, own a piece of a diversified portfolio, and no longer hold a concentrated single-stock position. Requires $1M+ minimum and a 7-year lock-up.

When you sell concentrated stock, capital gains in California can exceed 37%. Tax-aware investing builds a reservoir of losses in your broader portfolio to offset those gains. Direct indexing owns the individual stocks in an index rather than an ETF, harvesting losses daily. For very large, low-basis positions, a 130/30 long-short strategy amplifies loss harvesting further, potentially saving six figures or more in taxes over time.