Insights

ipo-day
What You Should Know Before IPO

If you’re a startup founder, executive, or employee, your company’s IPO might be your first experience with managing wealth. While an influx of cash is certainly a blessing, it also brings new challenges into your life. What you do the year leading up to IPO day can ...

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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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3 (More) Essential Questions About 83(b) Elections

In part one of this two-part series, we reviewed how an 83(b) election works, how it can reduce taxable income, and the potential drawbacks of filing the election. In part two, we’ll look more closely at how 83(b) applies (or doesn’t apply) to different types of equity ...

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maximize-rsus
5 Ways to Maximize Restricted Stock Units (RSUs)

If your company is headed toward public offering, whether through IPO, SPAC, or direct listing, it’s likely you’re wondering how you can make the most of your equity compensation. While this can take several different forms, this article will specifically examine the ...

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Stock Options Are Like Avocados, Part 5 - Don't Let Your Avocados Rot on the Shelf!

Peak ripeness can be elusive.  When you buy avocados, it’s often for a specific purpose. Maybe you’re planning to have fajitas for dinner this week or make guacamole for a party. If you start worrying about whether the avocados are at the peak of their ripeness, ...

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Your Stock Options Are Like Avocados, Part 4 - Leverage More Trees to Make More Guacamole!

In the first three parts of this series, we used an avocado analogy to discuss when it’s time to exercise your stock options (pick the avocados), what it takes to be ready to sell your shares (make guacamole), and how to keep more of that guacamole for yourself and ...

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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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stock-options-avocados
Stock Options Are Like Avocados, Part 2 - Are You Ready to Make Guacamole?

It’s common for startup executives to plan to sell shares to cover major expenses such as taxes that are due for the previous year’s options exercise, a child’s college tuition, or buy a new home. While this can be a useful strategy, it’s essential to plan your share ...

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stock-options-avocado
Your Stock Options Are Like Avocados, Part 1 - Let Them Ripen!

Amazing guacamole comes from knowhow. As any amateur dip maker can tell you, the key to great guacamole is great avocados. Picking the right avocados from the market is an art as much as a science. When it comes to your stock options understanding when your options ...

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Pre-IPO Planning Checklist

If your company is preparing to go public, whether through IPO, SPAC, or direct listing, you have a lot of decisions to make leading up to the big day. The choices you make in the coming weeks and months will have a lasting impact on your long-term financial future. ...

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financial-goal-setting
The Importance of Pre-IPO Financial Goal Setting

If you’re working at a pre-IPO company, tremendous financial opportunities may be on your horizon. You may have big dreams about what you can do with your anticipated windfall, but without clear financial goals and proper structures in place to reach them, those dreams ...

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10b51-trading-plans
Common Questions About 10b5-1 Trading Plans

Your company’s public offering can bring tremendous financial opportunities. Making the most of them requires careful planning. However, as an employee, blackout periods and concerns about insider trading hang over your decisions about when to buy or sell your company ...

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