Daniel Zajac, CFP | Equity Compensation with Daniel Zajac

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How Incentive Stock Options May Be Taxed: And Some Caveats About Seeking A Qualified Disposition

by Daniel Zajac, CFP®, EA | Last updated May 4, 2025 | Incentive Stock Options

Who doesn’t love a great tax break? You and I can’t personally reverse a bear market or revise Federal regulations. But we do get to decide when and how to...

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What Equity Compensation Shares Are the Best to Contribute to a Donor Advised Fund? Part 1

by Daniel Zajac, CFP®, EA | Last updated May 4, 2025 | Considerations When You Have Significant Equity Compensation, Donor Advised Fund

If there’s such a thing as a match made in philanthropic heaven, it may be the ability to donate a portion of your equity compensation shares to a Donor Advised...

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What Equity Compensation Shares Are the Best to Contribute to a Donor Advised Fund? Part 2

by Daniel Zajac, CFP®, EA | Last updated May 4, 2025 | Donor Advised Fund, Equity Compensation

To achieve this win-win ideal, it’s important to be deliberate about which equity compensation share lots you donate, as well as whether you donate them as post-sale cash proceeds, or...

Why Exercising Incentive Stock Options When the Stock Price is Down May Not Be Your Best Strategy

by Daniel Zajac, CFP®, EA | Last updated May 4, 2025 | Incentive Stock Options

Wouldn’t it be great if your company stock price only ever went up—especially if you’re participating in its growth through incentive stock options (ISOs)? Unfortunately, that’s not always how the...

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Comparing Incentive Stock Options and Non Qualified Stock Options

by Daniel Zajac, CFP®, EA | Last updated May 4, 2025 | Employee Stock Options, Incentive Stock Options, Non Qualified Stock Options

Non-qualified stock options and incentive stock options are the two types of employee stock options that you may receive as part of your compensation package. While they have some similarities,...

83(b) election

by Daniel Zajac, CFP®, EA | September 2, 2022 | 8

You can file an 83(b) election to accelerate a taxable event on your stock options or restricted stock awards, so it occurs sooner than it normally would. Why would you...

Alternative minimum tax (AMT) and AMT Credits

by Daniel Zajac, CFP®, EA | September 2, 2022 | A

AMT is a parallel system for figuring how much tax you owe the IRS each year. You or your tax preparer calculate your annual taxes based on both standard and...

AMT Crossover

by Daniel Zajac, CFP®, EA | September 2, 2022 | A

A calculation that projects the maximum number of incentive stock options that can be exercised and held in a given year without incurring AMT.

Appreciated/depreciated stock

by Daniel Zajac, CFP®, EA | September 2, 2022 | A

When a stock has appreciated, it has increased in value since you acquired it. When a stock has depreciated, it has declined in value since you acquired it.

Capital gains (short- and long-term)

by Daniel Zajac, CFP®, EA | September 2, 2022 | C

When you sell a security for more than you paid for it (for more than its cost basis), the difference is a realized capital gain, subject to taxation if it...

Capital losses

by Daniel Zajac, CFP®, EA | September 2, 2022 | C

When you sell a security for less than you paid for it (for less than its cost basis), the difference is a realized capital loss. If you incur losses in...

Cashless exercise/sell to cover

by Daniel Zajac, CFP®, EA | September 2, 2022 | C

For stock options, a simultaneous exercise and sell of some or all of your exercised options that allows you to cover the cost of the shares and any subsequent taxes...

Insights

How Incentive Stock Options May Be Taxed: And Some Caveats About Seeking A Qualified Disposition

What Equity Compensation Shares Are the Best to Contribute to a Donor Advised Fund? Part 1

What Equity Compensation Shares Are the Best to Contribute to a Donor Advised Fund? Part 2

Why Exercising Incentive Stock Options When the Stock Price is Down May Not Be Your Best Strategy

Comparing Incentive Stock Options and Non Qualified Stock Options

83(b) election

Alternative minimum tax (AMT) and AMT Credits

AMT Crossover

Appreciated/depreciated stock

Capital gains (short- and long-term)

Capital losses

Cashless exercise/sell to cover

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