What You Should Know About Double-Trigger RSUs

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How to Get Cash from Your Stock Without Selling at IPO

When you work for a startup, IPO is an immensely exciting time. Executives and employees who have been receiving equity compensation may be looking forward to IPO day in anticipation of a big payout. Typically, however, company insiders aren’t allowed to sell shares at ...

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Giving Back, Getting Back: Charitable Donations & Your Tax Return

Sharing your good fortune with others by donating to charities can generate a host of benefits. Not only can it spark that warm feeling inside of knowing that you’re making a difference; giving has also been shown to have the power to convey important health advantages ...

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Tax Implications of RSU Double-Trigger Acceleration

What are RSUs? Restricted stock units (RSUs) are a type of stock that companies often grant to employees as an incentive to remain with the company and contribute to its growth. Unlike stock options, which grant the right to purchase stock at a specified price, RSUs do ...

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How Is the Alternative Minimum Tax Calculated?

As a startup employee with options or shares in your company, you may be encountering the alternative minimum tax (AMT) for the first time. Before the AMT, many high-income filers could largely avoid federal income tax liability by taking a variety of deductions and ...

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What Pre-IPO Employees Should Know About the Alternative Minimum Tax (AMT)

What is Alternative Minimum Tax? The alternative minimum tax (AMT) is a provision of the tax code designed to obligate high-income taxpayers to pay at least a minimum amount of tax. When the AMT is triggered, a taxpayer must calculate their taxable income twice: once ...

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Will I Owe Taxes When My Company Goes Public?

For employees who own equity in their companies, the approach of IPO day is filled with excitement. Along with the possibility of newfound wealth, however, comes the prospect of a sizeable tax bill. If your company is on the path to public offering, you may be ...

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Your Stock Options Are Like Avocados, Part 3 - Don’t Give Away Too Much Guac!

In parts 1 and 2 of our analogy between stock options and avocados, we discussed the importance of understanding when your stock options are ready to pick (exercise) and your shares ready to slice (sell) depending on what type you have (ISOs or NSOs). In this ...

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How to Keep Your Taxes Under Control in an IPO Year

The time leading up to your company’s IPO or SPAC merger can be intensely exciting and, at times, overwhelming. A debut on the public market often marks a steep increase in income for employees. This new influx of wealth, however, requires a new level of tax planning. ...

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How are Restricted Stock Awards and Restricted Stock Units Taxed?

Restricted stock awards (RSAs) and restricted stock units (RSUs) are two types of incentive programs that are common in startup companies. While similar, there are some key differences in how these benefits are delivered and taxed. Both require careful tax and ...

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Active Tax Loss Harvesting: The Great Reappearing Alpha

Alpha is elusive. Some advisors claim they’ve achieved it, only to have it slip through their fingers. Many of the most prestigious investment firms have spent billions developing algorithms trying to track it down. When alpha appears, it comes down to fractions of a ...

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How Does an Employee Stock Purchase Plan Work?

If your company offers an employee stock purchase plan (ESPP), it could provide a path to future wealth. Like any investment, however, participating in an ESPP carries risk. Before signing up, you should understand how an ESPP works, the specific provisions of the plan ...

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What Is a Grantor Retained Annuity Trust (GRAT)?

A grantor retained annuity trust (GRAT) can allow you to avoid large amounts of gift or estate tax while transferring high-value investments to the next generation. Changing Estate Tax Law While most families don’t have to worry about estate taxes, they can put a ...

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CRTs: The Mr. Hyde of Charitable Trusts

In a previous blog post, we discussed how charitable lead trusts (CLTs) could be used to gain a large tax deduction, offset other capital gains, and fund philanthropic interests. However, that is just one side of the charitable trust world; charitable remainder trusts ...

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What You Should Know About Double-Trigger RSUs

In the nascent days of a startup, stock options are the norm. Early employees can expect access to incentive stock options (ISOs), and non-qualified stock options (NSOs), which are leveraged type options that can make someone very wealthy, very quickly. But as a ...

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ISOs – The Importance of 83(b) Pt. 3

In Part I of “The Importance of 83(b),” we conducted a survey of the 83(b) election and discussed in what context the election made sense when it came to restricted stock awards (RSAs). In Part II, we looked at examples of 83(b) elections for RSAs. Now, in Part III, ...

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An Introduction to Stock Options and Taxes

As the number of startups hit new heights in the Silicon Valley and various companies are utilizing equity to help attract, retain, and motivate skilled workers, the term “incentive stock option” is becoming more common in employment contracts. Although many will use ...

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RSA Examples – The Importance of 83(b) Pt. 2

In Part I of “The Importance of 83(b),” we shared a survey of the 83(b) election, and discussed in what context the election made sense when it came to restricted stock awards (RSAs). In this post, we are going to go through some examples of what can be accomplished ...

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ISOs Pt. 1 – Stock Options and Taxes

As we sign on the dotted line and say yes to a job offer, many of us do not completely comprehend the full effect of what we are signing. Aside from income tax on the base salary, we often overlook the tax consequences caused by the other big variable—stock ...

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RSAs – The Importance of 83(b) Pt. 1

Most people have heard of the famous Internal Revenue Code sections 401(k), 403(b), 121, and 1031, yet there are a few that tend to slip under the radar for most taxpayers. One code section that has a meaningful impact on a taxpayer’s return is 83(b). What is 83(b)? At ...

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