What You Should Know About Double-Trigger RSUs

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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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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)? ...

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