The place where we share our thoughts on financial planning for equity compensation, retirement planning and other issues that impact tactical planning for corporate executive's wealth, pay and benefits.
Monday, June 8, 2026
Leaving a job before options vest? Learn what typically happens to unvested grants, key plan terms, and time-sensitive steps to consider.
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Monday, June 1, 2026
Learn what a startup tender offer is, key terms to review, common timelines, tax considerations, and how to weigh liquidity vs. future upside.
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Friday, May 29, 2026
Avoid common RSU tax-return mistakes like double-counting income, wrong cost basis, and under-withholding. Learn practical steps to reduce errors.
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Thursday, May 28, 2026
Learn whether you can be granted both ISOs and NQSOs, key differences, common limits, and planning steps to align equity decisions with your goals.
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Wednesday, May 27, 2026
Learn how RSU vesting often shows on your W-2, which boxes change, and what to check to avoid surprises at tax time.
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Wednesday, May 27, 2026
Wondering if your equity is QSBS? Review a practical checklist on C-corp status, issuance, assets, business type, and holding period.
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Tuesday, May 26, 2026
Learn which tax forms you’ll receive after selling company stock (1099-B), what to review for cost basis, and key equity-compensation pitfalls.
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Tuesday, May 26, 2026
Key retirement planning questions for stock options, RSUs, and ESPPs—taxes, vesting, diversification, and income planning for confidence.
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Tuesday, May 26, 2026
Learn what an 83(b) early equity exercise is, why people file it, key deadlines, and trade-offs to weigh before deciding.
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Monday, May 25, 2026
Learn what a 10b5-1 plan is, how it works, and why executives use it to plan stock trades while managing insider-trading risk.
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Monday, May 25, 2026
Learn how blackout and lockup periods can affect stock options, ESPPs, and trading windows—and practical steps to plan ahead.
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Sunday, May 24, 2026
Exercising ISOs can trigger AMT due to the option “spread.” Learn when risk rises and what planning steps to discuss before exercising.
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Saturday, May 23, 2026
Moved after earning stock options? State taxes may depend on residency and where income was earned. Learn key rules and planning steps.
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Friday, May 22, 2026
Learn tax-aware options when selling company stock, including staged sales, charitable gifting, QSBS/NUA considerations, and loss offsets.
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Wednesday, May 20, 2026
Learn what Net Unrealized Appreciation (NUA) is, how it may tax employer stock in a 401(k), and key trade-offs to consider near retirement.
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Tuesday, May 19, 2026
Learn how NQDC plans defer income today for future payouts, how taxes and distributions work, and key risks like employer credit exposure.
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Tuesday, May 19, 2026
Learn what stock option dilution can look like in pre-IPO private funding rounds, what drives it, and steps to set expectations and plan ahead.
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Monday, May 18, 2026
Learn what short-swing profits liability is, who it applies to, and how stock options, RSUs, and sale timing can create unexpected risks.
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Monday, May 18, 2026
Selling ISO shares before 1 year from exercise (or 2 years from grant) is usually a disqualifying disposition. Learn key tax and AMT issues.
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Sunday, May 17, 2026
Learn why companies favor RSUs over stock options: simplicity, perceived value, retention, dilution considerations, and planning tips for recipients.
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Friday, May 15, 2026
Learn how stock options may be divided in community property states, including timing, vesting, time-rule formulas, and key planning steps.
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Thursday, May 14, 2026
A practical framework to evaluate vested stock options: exercise & hold, exercise & sell, or wait—plus key tax, risk, and planning trade-offs.
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Wednesday, May 13, 2026
Learn which stock option and RSU terms may be negotiable at hire, what to ask HR, and how to evaluate equity offers in your plan.
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Monday, May 11, 2026
RSUs vesting soon? Learn key factors to decide whether to sell or hold—taxes, concentration risk, goals, and a practical “sell some, hold some” approach.
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Friday, May 8, 2026
Learn how to manage RSUs, stock options, and ESPPs with a clear plan for taxes, diversification, vesting timelines, and long-term goals.
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Wednesday, May 6, 2026
Unsure whether to exercise oldest stock option grants or oldest vested tranches? Learn key factors: expiration, ISO/NQSO taxes, and risk.
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Friday, May 1, 2026
Learn key considerations for financing an early stock option exercise, including taxes, liquidity, borrowing risks, and concentration planning.
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Monday, April 27, 2026
Learn when ISO exercises affect your W-2, why some don’t, when wages may appear after an early sale, and how AMT can factor in.
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A step-by-step guide for senior executives. Here’s the uncomfortable truth: Deciphering the complexity of your financial world is a full-time job.
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Friday, January 9, 2026
Year-end stock comp checklist: taxes, vesting dates, concentration risk, withholding, selling strategy, and key records to review before year-end.
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Thursday, October 30, 2025
ISOs are quite often exercised with the intention of holding the stock to qualify for long-term capital gains treatment on the full gain over the exercise price. Year-end planning and review is a must.
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The critical time for tax planning is at year-end. Of course, you should be thinking about tax planning all year, but year-end is when you can adjust any portion of your strategy that may have gotten off track due to market movements.
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Get ready for a roller-coaster ride! With your IPO company's stock price, you want to hope for the best but plan for the worst. Be serious about this new-found wealth. It's no longer pie-in-the-sky money.
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Market volatility and sharp declines rattle even the most experienced holders of stock compensation. Sooner or later, market volatility will probably force you to make decisions that affect your financial future and long-term wealth.
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Does you Advisor Understand Your Equity Compensation Well Enough to Help you Plan it?
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While many recipients of equity compensation intend to use it to boost their savings and lifestyles, I find that many of them do not see it in the bigger picture of retirement savings.
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I see too many smart people with substantial gains in stock options who do dumb things. A disciplined stock option exercise strategy can prevent some big mistakes and significantly increase the value of your option grants.
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SEC Rule 10b5-1 had a significant impact on how directors, officers and other employees who are subject to “blackout” periods diversify their company stock holdings.
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Restricted and performance shares have continued to accelerate in popularity over other equity compensation alternatives, so it shouldn't surprise employees that their company is now granting them in place of stock options.
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If you are one of the fortunate employees of the almost 10,000 public company employers in the US who receive a portion of your compensation in company stock, you should think seriously about the advice you get.
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At some point with your company stock, too much of a good thing can cause you to worry, lose sleep, and become too focused and frustrated about its performance.
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Many Baby Boomers might not be ready for retirement, but younger workers have a chance to do better – if they make the most of their 401(k)s. The return and principal value of stocks fluctuate with changes in market conditions. Shares when
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Divorce can be a major disruption to a family’s financial plans. Surprisingly, the Internal Revenue Service (IRS) and Congress have actually worked to make a difficult proceeding less overwhelming and burdened with taxation.
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