High‑income tax planning thread

A tax thread aimed at people with $250,000 to $500,000 salaries and $1 million to $5 million equity or bonus payouts took off on X on April 14, pushing high-earner planning into the feed before year-end deadlines arrive. (x.com) Thomas Kopelman, co-founder of AllStreet Wealth, framed the issue around workers whose pay comes in uneven chunks: salary, restricted stock units, and large bonuses that can land in a single quarter. His public bio says he works with equity-compensated clients, and AllStreet’s intake form targets households earning from $250,000 to more than $2 million. (thomaskopelman.com) (allstreetwealth.com) The core warning is about withholding, not whether tax is owed. Internal Revenue Service Publication 15 says supplemental wages are generally withheld at 22 percent, and at 37 percent once supplemental wages paid in the year exceed $1 million. (irs.gov) That flat withholding rate can miss a high earner’s actual bill when salary, state tax, and vesting stock push total income far above the withholding default. The Treasury regulations define bonuses and other non-regular pay as supplemental wages, which is why a large vest or bonus can leave a cash gap even when shares are sold to cover taxes. (ecfr.gov) (irs.gov) Restricted stock units work like deferred pay delivered in shares, and the tax clock starts when they vest, not when the grant is first awarded. The value at vest is treated as wages on a Form W-2, and any later move in the stock price becomes a capital gain or loss when the shares are sold. (summitry.com) (turbotax.intuit.com) That is why planners often tell clients to decide in advance whether vested shares will be sold immediately or held as an investment position. A same-day sale can limit exposure to a single stock after tax has already been triggered at vesting, while holding shifts the question from compensation planning to portfolio risk. (summitry.com) (irs.gov) The retirement-account piece in the thread lines up with 2026 contribution limits. The Internal Revenue Service says workers can defer up to $24,500 into a 401(k) plan in 2026, with total employee deferrals generally rising to $32,500 for people age 50 and older because the standard catch-up is $8,000. (irs.gov) Health savings accounts are another lever for workers enrolled in high-deductible health plans. Revenue Procedure 2025-19 set the 2026 limit at $4,400 for self-only coverage and $8,750 for family coverage, with a $1,000 catch-up for people age 55 or older. (irs.gov) The charitable-giving point centers on donor-advised funds, which let a donor contribute assets now and recommend grants to charities later. Internal Revenue Service Publication 526 says a donor-advised fund is an account where the donor can advise on distributions or investments, and contributions can be deductible if the taxpayer itemizes and follows the limits and recordkeeping rules. (irs.gov) For people sitting on appreciated stock, the appeal is usually tax timing and capital-gains avoidance rather than a bigger gift alone. The playbook Kopelman described is less about finding a loophole than matching cash reserves, withholding estimates, equity-sale dates, and annual contribution limits before a windfall turns into an April surprise. (x.com) (irs.gov)