Raymond Hall, EA

A large position in one stock usually arrives the same way: years of equity compensation, a founder's shares, or an acquisition paid in the buyer's stock. At some point the household decides to reduce it. Whether and how fast is an investment decision. But every way of reducing a position has a tax result, and the tax result depends on records that many households cannot produce on short notice: basis, acquisition dates, the type of grant, and any restrictions on sale. This post covers the tax side of reducing a concentrated stock position in 2026: what records to assemble, how the main approaches are taxed, and which questions belong to your preparer, your investment advisor, and counsel. It is not investment advice and it does not recommend any strategy. It is a framework for walking into that conversation with the facts ready. Start with the lot record Before any decision, build a lot-level record of the position. For each lot: Acquisition date and how it was acquired...

Investments in space, defense technology, and other frontier companies tend to arrive through unusual paths: a friend's seed round, a special purpose vehicle (SPV) organized by a syndicate lead, a convertible note, or shares received for advising a startup. Whether to invest is not a tax question. But each of those paths produces a different tax record, and the records are often thin. Years later, the household needs to prove basis, holding period, qualified small business stock status, and value for gifts, and the company may have moved on, merged, or closed. This post covers the tax and document questions to ask at the time of an early-stage investment in a frontier company, and the records to keep afterward. It is not investment advice, it does not evaluate any company or technology, and it is not buyer diligence. It is a list of what your preparer and counsel will need from you later. First question: what exactly did you buy? The instrument decides the tax treatment. Write...