What You Should Know About Double-Trigger RSUs

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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 ...

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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 this third ...

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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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