Direct indexing and charitable trusts, without the pitch.

Direct indexing, generically

Direct indexing means owning the individual stocks that make up an index, or a custom sleeve of them, instead of a single mutual fund or ETF share class. The usual marketing claim is tax-loss harvesting at the lot level, plus the ability to underweight a stock you already have too much of, such as employer shares.

That last point is why tech executives hear about it. If most of your net worth is one ticker, buying a fund that also holds that ticker is not diversification. A separately managed account can sometimes exclude or underweight that name. Fees, tracking difference, wash-sale rules, and whether you even have taxable account space all matter. None of that is a recommendation to open an SMA.

Charitable remainder trusts, generically

A charitable remainder trust (CRT) is an irrevocable trust that can pay a stream to one or more non-charitable beneficiaries for a term or life, with the remainder going to charity. People discuss CRTs when they have highly appreciated stock and a charitable intent. There are also charitable lead trusts, donor-advised funds, and outright gifts. They are different instruments with different tradeoffs.

A CRT can involve income-tax deductions, capital-gains treatment inside the trust, and payout-rate rules. It can also be a poor fit if you need flexibility, if the charity remainder is an afterthought, or if the trust is sized wrong. Irrevocable means irrevocable. This page does not size a trust, pick a payout, or tell you to fund one with employer stock.

Donor-advised funds are not CRTs

A donor-advised fund is a simpler charitable account at a sponsoring organization. Contributions can be cash or, in some cases, appreciated securities. Grant recommendations go to public charities later. DAFs and CRTs get conflated in dinner conversation. They should not be conflated in documents.

What belongs in a professional meeting

• Do you have a genuine charitable intent, or only a tax problem?
• Is the position long-term appreciated stock, recently vested ordinary-income RSUs, or both?
• Are you an insider who cannot gift or sell without pre-clearance?
• What is the rest of the balance sheet besides the one ticker?

Bring those facts to a CPA and an estate attorney. If you later want an advisory conversation, that is a separate engagement with disclosures. The public site stops at the map.