Read practical guides for business sales, real estate exits, equity liquidity, windfalls, and other moments where the right advisor questions matter.
Tax drag is the gap between what an account earns and what you keep after taxes. These are the turnover topics worth raising with your advisors.
An installment sale can spread a capital gain across tax years, but recapture, related-party rules, and default risk all shape whether it fits.
A 1031 exchange can defer a large capital gains tax bill, but the rules are strict and the windows are short. These are the questions to work through with a tax advisor first.
Questions worth raising with a tax advisor about Section 1202 eligibility, the five-year holding period, and what varies by state.
Opportunity Zone funds offer real tax deferral on capital gains, but the compliance windows are unforgiving. Here is what to review before committing.
A stepped-up basis changes the capital gains math on inherited assets entirely. Here is what to review before deciding whether or when to sell.
A look at what changes when you deliberately keep some proceeds out of a 1031 exchange, and the topics worth reviewing with your tax advisor first.
A partially failed 1031 exchange usually comes down to boot. Here's what the term means and what to clarify with your advisor before you close.
Tax-loss harvesting can offset gains after a liquidity event, but the wash sale rule complicates timing. Topics to raise with your tax advisor.
