What should I do with my RSUs?

I’m surprised by how often financial planners will recommend to all their clients that they sell all their RSUs. Sometimes, this is the correct answer. But I think this conversation deserves nuance. Whether navigating thousands, hundreds of thousands, or especially millions of dollars, managing your RSUs is one of your most important financial decisions. So, let’s have a strategy.

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5 Strategies For Optimizing Cash Tax Efficiently After A Liquidity Event

Whether you are on the verge of an IPO, liquidity event, tender offer, or have been building up cash for a specific goal, you may be wondering, how you can optimize what you doing with your cash, above and beyond using a high-yield savings account. Here are some of the options I’ve been discussing with clients lately and have been using in client accounts to optimize large cash holdings (above $100k) with a focus on tax efficiency.

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Managing OpenAI Equity & Future Wealth

Collaborate with a financial planner to determine the amount of wealth that creates your full financial freedom and plan for the long term by developing a comprehensive financial plan. Engaging in a comprehensive cash-flow analysis and future projections with a financial planner can provide valuable context not only for deciding what to do with equity proceeds but also for aligning your wealth with what brings you joy and fulfillment. Doing so can also help create the context for developing a plan for future liquidity and the decision of how much OpenAI stock to hold for the long term.

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Matthias Giezendanner
The 2020 Booklist

Here are a few of the books that I most enjoyed and had the largest impact on my thinking in 2020. I offer them in hope that you will find one that enriches your life as much as they have enriched mine.

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Matthias Giezendanner
Understanding How The Alternative Minimum Tax Affects Your Incentive Stock Option Exercise Decisions

If you’ve been scouring the internet trying to wrap your head around the concept of the alternative minimum tax (AMT) and how it applies to your startup’s equity compensation you’ve probably come across at least one financial advisor, tax professional or journalist that has tried to scare you into believing that the AMT is a confusing mystery , far beyond the common woman or man.

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Maximizing The Return On Your Incentive Stock Options (ISOs) By Using Their Underlying Leverage

It turns out Incentive Stock Options are not unlike this playground seesaw. By taking advantage of the characteristics of your options, you can both leverage funds you have earmarked for option exercise to increase income while also protecting yourself from the underlying company stock’s potential downside.

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Deciding Whether to Exercise ISOs by Considering the Health of Your Startup

The single most important factor in considering if and when to exercise your options is their underlying value when they reach full liquidity – either through being acquired, following an initial public offering (IPO), or when the team closes shop. The fundamental question is, ‘will my startup succeed?’ But how do you measure this trajectory?

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Investing for Good: Socially Responsible Investing

In the last few years, the buzz about socially responsible investing (SRI) has been rolling through the investment world. Money has poured into socially responsible funds. Investors want to know whether their investments are contributing to positive change in the world. A recent study found that 40% of financial advisors say that SRI is important to them and their clients.

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