Insights
The After-Tax Brief
A short weekly note on what changed in tax law, markets, and planning, and what it may mean for investors, business owners, families, and the accountants who work alongside them. Written to be read in five minutes.
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Latest
Recent issues
- Markets
- Tax law
- Retirement
- Equity compensation
- Concentrated stock
- Liquidity events
- Charitable planning
- For accountants
Too much of your net worth in one stock? Five ways to reduce the risk, and the trade-offs of each.
Staged sales, loss harvesting, gifting, option hedges and exchange funds: the tools for reducing a concentrated stock position and the trade-offs of each.
Read the issueBeyond 'convert in a low year': how to build a multi-year Roth conversion plan.
How to size Roth conversions year by year, the window before RMDs, the effect on Medicare premiums and Social Security, and why paying the tax from outside the IRA matters.
Read the issueSelling your business? Most of the tax outcome is decided before the letter of intent.
Asset versus stock sales, the expanded QSBS rules, and the charitable, family, residency and installment moves that need lead time before a business sale.
Read the issueRSUs, ISOs, NSOs and ESPPs: a plain-English map of how your equity compensation is taxed.
How RSUs, NSOs, ISOs and ESPP shares are taxed, why RSU withholding often falls short, the ISO AMT trap, and how to build a plan for company stock.
Read the issueTax-loss harvesting: what it does, what it does not, and the rule that trips people up.
How tax-loss harvesting works, why it usually defers rather than eliminates tax, how the wash sale rule applies, and where it adds the most value.
Read the issueThe IRS drew a line around Section 351 ETF exchanges. Here is what it covers and what it does not.
A new revenue ruling treats certain ETF seeding arrangements as taxable, and a companion notice flags several other tax-aware fund strategies. What it means if you hold a concentrated position, and the questions worth asking before you act on headlines.
Read the issueHave a situation one of these issues touched on?
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