For most people, tax time can be a headache—though for earners with traditional compensation packages, it can at least be fairly predictable (W-2 wages, withheld taxes, 401(k) contribution deductions, etc.). If you’re a business owner, partner, or investor in a...
I’m Daniel Zajac, CFP®
I write about employee stock options and equity compensation in a way that is easy to understand.
How Your Income May Influence a Qualified Sale of Incentive Stock Options (ISOs)
Incentive stock options (ISOs) are known far and wide for their preferential tax treatment on the total recognized gain—as long as you meet the holding period requirements for a qualified sale.
The Basics of Equity Compensation
If your employer provides equity compensation as a part of its benefits package, you can expect to receive a wealth of information about the program. If you’re new to the subject, the amount of information and the details can be daunting, especially if you’re not yet familiar with the basics. To help with that, let’s take a step back and view the big picture on equity compensation.
When Intentionally Disqualifying ISOs at Year End May Make Sense
Deciding when to exercise, hold, and sell your incentive stock options (ISOs) is complicated, requiring you to manage several simultaneous financial variables, all at the same time. These include: Prices: Especially the strike price, the share price at exercise, and...
Rethinking Whether to Exercise and Hold Non-Qualified Stock Options for Long-Term Capital Gains Tax
When it comes to evaluating strategies to exercise your Non-Qualified Stock Options (NQSOs), what is your best plan of attack? Do you: Exercise and sell all your NQSOs immediately, cashing out the full proceeds? Exercise your NQSOs and hold shares of stock, hoping the stock price will go up? Or, leave your NQSOs unexercised and hope the stock price will go up? If you anticipate a higher stock price in the future…
Concentration Risk and Your Equity Compensation: Reasons and Rebuttals
Concentration risk is an issue of interest to nearly every employee, executive, business owner, or anyone else holding company stock and employee stock options. What is concentration risk? It’s loosely defined as holding a significant portion of wealth in a single stock, which could result in an inappropriately diversified portfolio. Unfortunately, the ambiguity associated
What Executives Need to Know About Performance Awards
A performance award is a grant of company stock or stock units, typically tied to a pre-determined metric or goal that is specific to the recipient or award itself. More often than not, the recipient is an executive. Interchangeably referred
The 10b5-1 Plan: 8 Frequently Asked Questions and Recent Updates
If you’re an executive or an employee with significant equity in your company from employee stock options, restricted stock units, or other stock grants, you may have a continual need to sell stock. However, SEC regulations, company insider trading policies and fears of allegations of insider trading may prevent proper diversification of holdings. Fortunately for executives and insiders, Rule 10b5-1 trading plans can allow flexibility to sell stock without regard to limitations imposed by company insider trading policies while complying with SEC regulations. Such plans also provide an affirmative defense to allegations of insider trading.
A Quick Take on the Tax Treatment of Incentive Stock Options
If your employer has granted you incentive stock options (ISOs), you’ve likely spent time researching the tax treatment. If so, you’ve probably read about the alternative minimum tax (AMT), and qualifying and disqualifying dispositions. Perhaps the complication has left you wondering: What does this mean to me as a taxpayer?
Simplifying the Equity Compensation Complexities: Keep it, Spend it, or Save it
If you’re wondering how to maximize the value of your incentive stock options (ISOs), non-qualified stock options (NQSOs), restricted stock units (RSUs), or other forms of equity compensation, you’re not alone. After all, there is plenty to think about if you’ve been granted equity compensation. You may dream of how to strike it rich. You may fear you’ll do something wrong and miss out. You might become mired in taxing technicalities, including AMT calculations. All that thinking can backfire if “TMI” (too much information) prevents you from proceeding.
Dive Deeper
Whether you’re just getting started or expanding your knowledge, here are some resources to get you started.
NEW! The Ultimate Guide to Equity Compensation
Understand what you have, what you should consider, and what ultimately matters to you.
Hi, I'm Daniel Zajac, CFP®, EA
I write about equity compensation and employee stock options in a way that is easy to understand.
NEW! The Ultimate Guide to Equity Compensation
Understand what you have, what you should consider, and what ultimately matters to you.
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Get the Ultimate Guide to Incentive Stock Options to better understand your equity compensation.