Sean O’Keefe

Sean O’Keefe

19 posts
How startup employees can sell their pre-IPO shares

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Sean O’Keefe

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Sep 22, 2020

How startup employees can sell their pre-IPO shares

How startup employees can sell their pre-IPO shares in tender offers or secondary transactions and what the tax implications are of doing this.

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Say goodbye to capital gains with QSBS!

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Sean O’Keefe

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Aug 31, 2020

Say goodbye to capital gains with QSBS!

Qualified Small Business Stock (QSBS) may allow you to exclude gains on all or a large portion of your Federal capital gain tax when you sell your stock.

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2020 Tax Brackets

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Sean O’Keefe

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Aug 28, 2020

2020 Tax Brackets

Most taxpayers are unaware that the US tax system is progressive. This means that your income is taxed at a higher rate as your income increases. These are called progressive tax brackets.

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Avoiding the underpayment penalty for quarterly estimated tax payments

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Sean O’Keefe

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Aug 26, 2020

Avoiding the underpayment penalty for quarterly estimated tax payments

Here's the bad news: owing taxes when you file your tax return can result in underpayment penalties. The more you owe, the bigger the potential penalties.

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3 ways to finance your next stock option exercise

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Sean O’Keefe

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Apr 9, 2020

3 ways to finance your next stock option exercise

Most startup employees can't afford the cost + taxes when they exercise their stock options, but you have options.

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Owe on your taxes? How to apply for an IRS payment plan

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Sean O’Keefe

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Apr 3, 2020

Owe on your taxes? How to apply for an IRS payment plan

If you owe money on your taxes and need more time to pay, here are some simple steps to get started applying for a payment plan with the IRS or your State of residence.

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The Price of Preferred and How it is Different than FMV.

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Sean O’Keefe

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Feb 9, 2020

The Price of Preferred and How it is Different than FMV.

Price of PreferredThe value that investors paid per share in the most recent round of fundraising. This is usually higher than the price that employees pay per share (fair market

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AMT Credit: Get Back AMT From Exercising Your Incentive Stock Options (ISOs)

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Sean O’Keefe

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Feb 5, 2020

AMT Credit: Get Back AMT From Exercising Your Incentive Stock Options (ISOs)

Have you exercised incentive stock options (ISOs) in the past few years? If so, you likely got hit with a sizable Alternative Minimum Tax (AMT) fee. AMT applies when you

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What Are Estimated Tax Payments and How Do I Avoid Penalties?

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Sean O’Keefe

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Feb 5, 2020

What Are Estimated Tax Payments and How Do I Avoid Penalties?

Making estimated tax payments is one way to avoid a huge lump sum tax payment at the end of the year. Instead, you send money to the IRS throughout the

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What Every Startup Employee Needs to Know About 409A Valuations

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Sean O’Keefe

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Feb 5, 2020

What Every Startup Employee Needs to Know About 409A Valuations

By definition, a 409A valuation determines the fair market value of a startup company’s stock. These valuations are usually conducted by an independent third party and are filed with

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What Every Startup Employee Should Know About 83b Elections

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Sean O’Keefe

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Feb 4, 2020

What Every Startup Employee Should Know About 83b Elections

When you exercise your stock options (ISO, NSO), you will need to consider the tax implications to exercising. The employee pays taxes on the spread between your stock’s fair

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How Does Alternative Minimum Tax (AMT) Impact Exercising My Stock Options?

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Sean O’Keefe

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Feb 1, 2020

How Does Alternative Minimum Tax (AMT) Impact Exercising My Stock Options?

If you have stock options (ISO, NSO or RSU), chances are you’ve heard about Alternative Minimum Tax. But what exactly is it and how is it calculated? And more

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Leaving a Startup? Why Buying Your Stock Options Now Can Save Money on Taxes

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Sean O’Keefe

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Jan 8, 2020

Leaving a Startup? Why Buying Your Stock Options Now Can Save Money on Taxes

If you leave a startup company, whether by choice or you are asked to leave, it’s important to know what happens to your employee stock options (ISO, NSO). When

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What is a Restricted Stock Unit (RSU) and How is It Taxed?

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Sean O’Keefe

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Jan 1, 2020

What is a Restricted Stock Unit (RSU) and How is It Taxed?

Employee salaries are a major expense for most startups, which is why many elect to enhance their employee compensation with restricted stock units (RSUs) and other stock options. Such a

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What is Capital Gains? How are they taxed?

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Sean O’Keefe

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Dec 27, 2019

What is Capital Gains? How are they taxed?

If you own capital assets, such as a house, stock options (ISO, NSO, RSU), or a retirement plan, then you need to be aware of the term "capital gains". Eventually,

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What is a Non-Incentive Stock Option (NSO) and How Is It Taxed?

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Sean O’Keefe

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Dec 15, 2019

What is a Non-Incentive Stock Option (NSO) and How Is It Taxed?

As startups are finding ways to attract top talent, stock options have become a common perk to offer monetary incentive and give employees a sense of pride and ownership in

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What is a Vesting Schedule?

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Sean O’Keefe

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Dec 1, 2019

What is a Vesting Schedule?

Option grants (ISO, NSO) or RSUs are a promise from your employer that you will receive stock in a company at a discount to what investors are paying. Before you

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What is an Incentive Stock Option (ISO) and How Is It Taxed?

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Sean O’Keefe

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Nov 1, 2019

What is an Incentive Stock Option (ISO) and How Is It Taxed?

Most startups enter competitive landscapes when they open their doors, particularly when it comes to talent sourcing. With limited budgets, they’re usually not in a position to compete on

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What is the Fair Market Value (FMV)?

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Sean O’Keefe

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Oct 27, 2019

What is the Fair Market Value (FMV)?

If want to know the current value of a company that is traded on the public stock market (e.g. NYSE or NASDAQ), you can easily go online and look

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Sean O’Keefe

Sean O’Keefe

19 posts