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"The number of shares you can sell depends on both individual limits and the total level of participation. If you have held the shares for any period before the tender offer and sell the stock at a premium over your company's current internal valuation, the tax treatment for that part of the gain is uncertain.... Advisors often recommend selling shares to diversify. However, the potential downside to selling shares now is that it could take away from much greater gains later in any IPO."  MORE >>

"[1] Always report stock sales on Form 8949 and Schedule D, even if you sold all the shares immediately after acquiring them.... [2] [T]he cost basis reported by your broker on Form 1099-B is likely to be too low, requiring an adjustment on Form 8949. [3] Watch for the common error of double-reporting stock comp income on Form W-2.... [4] After an exercise/hold of ISOs, always calculate your alternative minimum tax (AMT). [5] If you owe the AMT, remember to use any AMT credit you may have."  MORE >>

"[1] Understand the vesting schedule of your restricted stock units (RSUs).... [2] Know how your company will withhold the taxes on your RSU shares.... [3] Have a plan for the RSU shares you will receive at vesting."  MORE >>

"In July 2025, the 'One Big Beautiful Bill' Act of 2025 (OBBBA) made permanent the tax rates of the Tax Cuts & Jobs Act (TCJA) that were set to expire at the end of 2025. However, it also brought some changes that may affect planning for equity comp and company shares at year-end 2025.... [myStockOptions] asked many leading financial advisors, from different regions of the United States, for their ideas on financial and tax planning for the end of this year and the start of the next. [This article provides] their selected responses, presented in their own words."  MORE >>

"When you are evaluating whether to exercise stock options or sell shares from vested restricted stock/RSUs or an ESPP, you want to consider the thresholds that may trigger higher tax rates for you either this year or next. Assess whether you should defer income into next year or accelerate income into this year. Project your income from equity awards to see whether it will trigger the additional Medicare taxes on high incomes this year or next year."  MORE >>

"A 'Scenario of Least Regret,' presents a little-by-little approach that can balance the competing interests of ambition and anxiety. Dollar-cost averaging is an effective way to inch out of a concentrated stock position. Check your overconfidence level by considering what you have to lose. Reframe your thinking out of tunnel vision on the stock price and consider the things you actually want to accomplish in your life with your stock wealth.... Form a plan with an advisor just one stage at a time if necessary. Focus on what percentage of company stock you want to keep, i.e. your 'legacy anchor position.' "  MORE >>

"While it's a good idea to have a plan for any equity awards, tax planning is especially crucial for incentive stock options (ISOs). The special tax treatment that ISOs offer under the tax code is offset by the tradeoff of risk and more complicated taxation."  MORE >>

"[T]he higher cap on the SALT deduction comes with ... a phaseout for those with yearly adjusted gross income (AGI) exceeding $500,000.... [P]lanning ideas to try to hold your AGI below the phaseout zone ... include maximizing contributions to qualified retirement plans ... putting salary or bonuses into any nonqualified deferred compensation plan that's available; and exploring eligibility for other retirement or pension plans that defer income.... [E]valuate whether to avoid triggering more income, such as with Roth IRA conversions, nonqualified stock option exercises, and asset sales."  MORE >>

"The 'One Big Beautiful Bill Act of 2025' (OBBBA) made permanent many of the tax provisions in the Tax Cuts & Jobs Act of 2017 (TCJA) that relate to stock comp planning, with a few changes.... This quiz is also a course of study. The answer key links to content on the topic for follow-up reading."  MORE >>

"[T]he 2025 tax law ... [includes] changes that influence the calculation of the alternative minimum tax (AMT), most notably in the significantly raised cap on state and local tax (SALT) deductions. Other provisions in the law concern the special tax treatment for startup company stock and tax planning around charitable donations. Some of these new provisions will become effective in 2026. Others take effect sooner."  MORE >>

"[1] Rates and brackets of individual income tax ... [2] The calculation of the alternative minimum tax (AMT) ... [3] Trigger point for the 20% tax rate on long-term capital gains ... [4] Estate planning and charitable contributions ... [5] Qualified small business stock (QSBS) ... [6] Section 83(i) tax-qualified stock grants for private companies ... [7] Performance-based exception to section 162(m) limit on deductible comp."  MORE >>

"Questions to ask before RSU vesting ... [1] Tax-withholding trap at RSU vesting ... [2] RSU vesting years: reduce taxable income ... [3] Hold or sell the stock at vesting? ... [4] RSU selling plans impacted by insider-trading rules ... [5] RSU taxes can motivate diversification."  MORE >>

"Donating wealth to charities and passing it along to future generations are important financial goals. What planning techniques are optimal if a large portion of your wealth comes from stock compensation?"  MORE >>

"Decision-making moments come at you fast when you have stock options, restricted stock units, an employee stock purchase plan, or other forms of company equity comp.... What grants do you expect? ... Job changes ahead? ... Tax planning for withholding ... ESPPs ... Tax returns ... Special issues for incentive stock options."  MORE >>

"January is an excellent time to consider your tax planning for 2025.... [T]hree sets of tax figures in 2025 that all employees should know ... relate to compensation from work ... [1] The Social Security wage base ... [2] Your income-tax bracket and withholding ... [3] Your contribution limit for qualified retirement plans ... [2] Inflation adjustments for health savings accounts."  MORE >>

"The longer-term outlook for the tax laws and the stock market is a key factor at year-end 2024 for employee stock options, restricted stock units (RSUs), employee stock purchase plans (ESPPs), and related holdings of company shares."  MORE >>

"Year-end is when many participants in NQDC plans ... choose how much of next year's pay to put away for the future. Generally, you defer income via nonqualified plans only when you know you will max out your yearly contributions to qualified plans, such as your 401(k). Crucially for this decision, the IRS just released the 2025 contribution limits for qualified retirement plans."  MORE >>

"There are various scenarios with equity compensation -- specifically restricted stock, stock options, and LLC interests -- in which making a timely Section 83(b) election with the IRS can be an important move for tax planning and minimization.... The welcome new Section 83(b) election form [IRS Form 15620] ... will be mailed to the IRS, but under the IRS modernization program it will eventually be submissible by e-filing."  MORE >>

"Start with your personal goals.... Be realistic with yourself.... Know how much tax will be withheld.... Sell the company shares or hold them?.... Automate selling under your plan where possible.... Capital gains tax."  MORE >>

"Case law abounds with disputes between former employees and companies over valuable stock options. While companies often prevail in such litigation, a recent lawsuit over startup company stock options in California ... resulted in a lucrative win for the plaintiff (a fired employee) and a notable ruling about how damages involving options can be calculated." [Shah v. Skilz, Inc., No. A165372 (Calif. App. Apr. 8, 2024)  MORE >>