For experienced investors

Finance 401

Past the basics? These are the more advanced strategies that higher earners and experienced investors tend to run into. Each is a short overview with a link to the full details. Educational only, not financial advice.

Tax-loss harvesting

Tax-loss harvesting means selling an investment at a loss to offset gains (and a limited amount of ordinary income) while staying invested. This covers the mechanics, the wash-sale rule, and where it fits.

Tax-loss harvesting

Wills & trusts (advanced)

Beyond a basic will, tools like revocable and irrevocable trusts, CRTs, GRATs, and ILITs address specific goals around control, taxes, and giving. This is an overview of the more advanced estate structures and what each is for.

Estate planning guide

Equity comp: ESPP, ISO, NSO/NQSO, RSU

Equity compensation comes in several forms, each taxed differently: restricted stock units (RSUs), incentive stock options (ISOs), non-qualified options (NSOs/NQSOs), and employee stock purchase plans (ESPPs). This is a tax-aware overview of how they differ.

RSUs & stock options

Donor-advised funds (DAF)

A donor-advised fund is a charitable account: you contribute (and can take a deduction) now, then recommend grants to charities over time. This explains how DAFs and deduction bunching work.

Donor-advised funds

Charitable remainder trust (CRT)

A charitable remainder trust can provide income to you or others for a period, with the remainder going to charity, alongside potential tax benefits. This is an overview of how CRTs are structured.

Charitable remainder trust

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Educational content only, not personalized financial, tax, or legal advice. Descriptions cover how strategies work in general; individual situations differ.