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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.

 

Wednesday, September 23, 2026

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.

 

Saturday, September 19, 2026

Key questions to ask about stock options, RSUs, and ESPP for retirement planning—vesting, taxes, concentration risk, cash flow, and selling strategy.

 

Saturday, September 19, 2026

Moved after retiring? RSU vesting and option exercises may be taxed by your new state, your former work state, or both. Learn the basics.

 

Saturday, September 19, 2026

Explore Social Security timing and how restricted stock units (RSUs), stock options, taxes, and cash flow can influence your decision.

 

Thursday, September 17, 2026

An S-1 filing starts the IPO process. Learn the common next steps, lockups, and equity planning considerations for employees and executives.

 

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Monday, September 14, 2026

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.

 

Sunday, September 13, 2026

ESPP participation usually doesn’t limit retirement contributions, but paycheck cash flow, employer match, tax planning, and concentration risk matter.

 

Friday, September 11, 2026

Considering financing an early equity exercise? Learn key risks—taxes, concentration, loan terms, illiquidity, and cash-flow strain—before you borrow.

 

Thursday, September 3, 2026

If something ever happened to my marriage, could I lose the stock options I earned?” If you’ve had that thought, you’re not being pessimistic. You’re being practical.

 

Wednesday, September 2, 2026

A practical framework for deciding whether to sell or hold RSUs at vesting, covering taxes, concentration risk, diversification, and goal-based planning.

 

Tuesday, September 1, 2026

RSUs vesting soon? Learn what “lapse” may mean, how RSUs are taxed at vesting, key elections, diversification considerations, and a prep checklist.

 

Sunday, August 30, 2026

Wondering when RSU capital gains holding starts? Often it begins at vesting when shares are delivered. Learn how basis and timing work.

 

Saturday, August 29, 2026

Learn why employers often grant RSUs over non-qualified stock options—simplicity, retention, value stability, and planning considerations.

 

Friday, August 28, 2026

Explore practical ISO exercise strategies to manage AMT when you also have NQSOs, including timing, staging exercises, and liquidity planning.

 

Friday, August 28, 2026

Learn the ISO annual $100,000 limit, how “first exercisable” is calculated, and what happens when part of a grant is treated as NSOs.

 

Friday, August 28, 2026

Key ISO rules beyond the $100,000 limit: plan requirements, exercise pricing, holding periods, post-employment deadlines, and AMT considerations.

 

Friday, August 21, 2026

Learn how ISO AMT credits are typically treated at death, whether they can be used on a final return, and key planning considerations.

 

Thursday, August 20, 2026

Learn when IPO shares can be sold, how lock-up periods work, and key tax and trading considerations for employees and investors.

 

Friday, August 7, 2026

Learn how to plan around RSUs, stock options, and ESPPs—taxes, diversification, and goal-based strategies to integrate equity comp confidently.

 

Thursday, August 6, 2026

Consulting equity grants can differ from employee awards. Learn key issues with options and restricted stock: vesting, taxes, liquidity, timelines.

 

Wednesday, August 5, 2026

Learn how RSUs and stock options may be assumed, converted, accelerated, or cashed out in a merger—plus key next steps to review.

 

Tuesday, August 4, 2026

Learn how 2025 tax updates and withholding mechanics affected RSUs, stock options, AMT exposure, and year-end planning for stock compensation.

 

Monday, August 3, 2026

Understand how employment claw-back provisions may work, common triggers, repayment terms, tax considerations, and smart questions to ask.

 

Sunday, August 2, 2026

Thinking of gifting company stock to a GRAT? Section 16 reporting may still apply. Learn why beneficial ownership matters and key next steps.

 

Saturday, August 1, 2026

Explore tax-smart ideas for equity compensation, estate planning, and charitable giving—plus key questions to discuss with your advisor team.

 

Thursday, July 30, 2026

Learn when an 83(b) election can apply to early-exercised stock options, key deadlines, and common risks to consider before filing.

 

Wednesday, July 29, 2026

Learn how private company stock and options are valued, including 409A FMV, common vs preferred shares, option pricing, and key value drivers.

 

Tuesday, July 28, 2026

Learn what double-trigger RSUs are, how private-company RSUs and stock options work, and the common tax rules to discuss with your CPA.

 

Sunday, July 26, 2026

Need cash and hold company stock? Learn how MNPI, blackout windows, and trading policies relate to insider trading risk and next steps.

 

Saturday, July 25, 2026

Learn how the SEC detects insider trading through surveillance, filings, tips, and digital trails—and why trades aren’t truly “confidential.”

 

Saturday, July 25, 2026

Learn when Form 4 is due, which equity comp events trigger filing, and the practical steps senior executives use to report insider transactions.

 

Thursday, July 23, 2026

SEC updated Rule 10b5-1 plan requirements in 2023, adding cooling-off periods and new disclosures—alongside heightened scrutiny and enforcement focus.

 

Wednesday, July 22, 2026

Exercising ISOs can trigger AMT due to the option “spread.” Learn when risk rises and what planning steps to discuss before exercising.

 

Tuesday, July 21, 2026

Donating ISO or ESPP shares may count as a disposition. Learn how holding periods affect disqualifying disposition rules and what to review first.

 

Sunday, July 19, 2026

Avoid common stock option exercise mistakes with dividend-paying shares: taxes, AMT, holding periods, diversification, cash needs, and timing.

 

Saturday, July 18, 2026

Learn practical, tax-aware strategies to reduce concentrated stock risk—staged selling, charitable tools, hedging, and portfolio alignment for retirement.

 

Thursday, July 16, 2026

Noncompetes can appear in equity grants and may affect career and financial planning. Learn what to review and the next steps to consider.

 

Wednesday, July 15, 2026

Form 3921 after an ISO exercise: what it means, what to save, AMT considerations, and key next steps for tax reporting and planning.

 

Tuesday, July 14, 2026

Learn how ISO stock sale gains may be taxed, including qualifying vs. disqualifying dispositions and possible AMT considerations.

 

Friday, July 10, 2026

RSUs can create a tax gap. Learn when estimated tax payments may help, alternatives like paycheck withholding, and a practical decision framework.

 

Thursday, July 9, 2026

Are you worried that complex equity comp could trigger an IRS audit? Learn what actually raises flags and practical steps to reduce errors and stress.

 

Wednesday, July 8, 2026

Learn how layoffs may affect vested and unvested stock options and RSUs, key deadlines, and what employers sometimes offer in severance.

 

Tuesday, July 7, 2026

Learn how stock options, RSUs, and ESPP shares may affect FAFSA through assets and income—and what to do when reporting isn’t clear.

 

Tuesday, July 7, 2026

Leaving a job? Ask these essential questions about stock options, RSUs, and ESPP deadlines, taxes, vesting, and next steps to avoid surprises.

 

Sunday, July 5, 2026

Does you Advisor Understand Your Equity Compensation Well Enough to Help you Plan it?

 

Friday, July 3, 2026

Explore tax-efficient ways to divest RSU shares, including sell-at-vest, staged selling, tax-lot selection, loss harvesting, and charitable strategies.

 

Thursday, July 2, 2026

Considering an overseas assignment? Learn how tax equalization may apply to RSUs, options, and other equity compensation—and what to ask HR.

 

Wednesday, July 1, 2026

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.

 

Wednesday, July 1, 2026

Learn how the AMT credit from ISO exercises works, when it can be used, and planning steps to track it and potentially use it over time.

 

Monday, June 29, 2026

How equity compensation affects estate and charitable planning: beneficiaries, trusts, liquidity, and tax-smart giving strategies for families.

 

Saturday, June 27, 2026

Changing from employee to consultant may affect option vesting, exercise deadlines, and taxes. Learn key questions to ask before switching.

 

Friday, June 26, 2026

Can you defer taxes from an equity exercise using a deferred comp plan? Learn what’s usually possible, plan limits, and key questions to ask.

 

Thursday, June 25, 2026

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.

 

Thursday, June 25, 2026

Learn the most common performance share (PSU) goals—TSR, EPS, revenue, cash flow, ROIC, and milestones—and how they affect vesting and planning.

 

Monday, June 22, 2026

Learn how to align stock options, RSUs, and ESPPs with retirement goals using tax-aware timing, diversification rules, and a clear savings plan.

 

Saturday, June 20, 2026

Learn how private equity buyouts may affect RSUs, stock options, and vesting—plus key questions, taxes to consider, and next steps.

 

Wednesday, June 10, 2026

ESPP payroll deductions usually don’t reduce your 401(k) or IRA contribution limits, but they can affect cash flow, taxes, and planning priorities.

 

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.

 

Saturday, June 6, 2026

Considering an 83(b) election? Learn key benefits, risks, and a practical checklist to weigh taxes, vesting, cash flow, and concentration risk.

 

Thursday, June 4, 2026

Learn when companies can restrict employee stock ownership, trading, and transfers—and what documents to review to understand your rules.

 

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.

 

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.

 

Friday, May 29, 2026

Questions to ask about performance share plans: vesting, metrics, taxes, job changes, trading limits, diversification, and planning.

 

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.

 

Thursday, May 28, 2026

Questions to ask about your ESPP: discounts, cash flow, exit rules, tax treatment, concentration risk, and whether to hold or sell shares.

 

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.

 

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.

 

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.

 

Tuesday, May 26, 2026

Key retirement planning questions for stock options, RSUs, and ESPPs—taxes, vesting, diversification, and income planning for confidence.

 

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.

 

Monday, May 25, 2026

Learn how blackout and lockup periods can affect stock options, ESPPs, and trading windows—and practical steps to plan ahead.

 

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.

 

Monday, May 25, 2026

Learn how NQSOs are typically taxed at grant, exercise, and sale—plus key timing, income vs. capital gains, and planning watch-outs.

 

Sunday, May 24, 2026

Learn how ISO exercises may trigger AMT, how qualifying vs. disqualifying sales are taxed, and what planning questions to ask before acting.

 

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.

 

Friday, May 22, 2026

Learn tax-aware options when selling company stock, including staged sales, charitable gifting, QSBS/NUA considerations, and loss offsets.

 

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.

 

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.

 

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.

 

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.

 

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.

 

Sunday, May 17, 2026

Learn why companies favor RSUs over stock options: simplicity, perceived value, retention, dilution considerations, and planning tips for recipients.

 

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.

 

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.

 

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.

 

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.

 

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.

 

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.

 

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.

 

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.

 

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.

 

Wednesday, October 29, 2025

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.

 

Friday, February 7, 2025

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.

 

Friday, January 10, 2025

Form 3922 is an informational ESPP stock form. Learn what it reports, what it doesn’t, and how to use it for tax and planning decisions.

 

Friday, November 15, 2024

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.

 

Monday, January 2, 2023

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.

 

Friday, October 14, 2022

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.

 

Wednesday, February 5, 2020

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.

 

Wednesday, January 15, 2020

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

 

Thursday, June 13, 2019

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.