Privacy and security when your wealth becomes more visible
This isn't about assuming the worst. It's the same kind of preparation as an umbrella insurance policy: a few low-cost steps now remove a real category of risk ...
The library
Learn at your own pace
Guides organized around the decisions you'll face, meeting you wherever your knowledge stands. Built from real experience working with private company equity holders, going well beyond what a surface-level search turns up.
After a liquidity event
After a liquidity event
Giving with appreciated stock: DAFs, foundations, and trusts
For many people, one of the first questions after a liquidity event isn't about returns. It's about what they want the money to do, and often that includes ...
Decisions and taxes
Equity and taxes for green card and visa holders
Most equity and tax guidance quietly assumes you're a U.S. citizen. If you hold a green card or a visa, some of it applies differently, and a few rules exist ...
Decisions and taxes
QSBS and Section 1202: what it is and when it can apply
Qualified small business stock, or QSBS, is one of the most valuable provisions in the tax code for early shareholders, and one of the most misunderstood. It ...
Decisions and taxes
How AMT works when you exercise incentive stock options
One of the most surprising tax bills in equity compensation comes from the alternative minimum tax, or AMT. It can arrive in a year when you haven't sold ...
After a liquidity event
Choosing an advisor: fiduciary duty, credentials, and how to check a record
Choosing who to work with is one of the most consequential financial decisions you'll make, and it's also where it's easiest to be sold to. A few direct ...
After a liquidity event
Sudden wealth: why it can feel strange, and why a pause helps
A liquidity event is supposed to feel good, and often it does. It can also feel disorienting, awkward, or oddly heavy. If that's true for you, you're in good ...
Liquidity events
Concentration risk and selling in stages
Believing in your company and holding most of your net worth in its stock are two different decisions. It's possible to feel strongly about the first and still ...
Liquidity events
Lockups, trading windows, and 10b5-1 plans: when you can actually sell
Becoming eligible to sell doesn't mean you can sell anytime. After a company goes public, several layers of rules decide when employees can sell. Knowing them ...
Decisions and taxes
Why your RSU tax withholding may not cover your tax bill
The most common money surprise after a liquidity event isn't a bad investment. It's a tax bill that's much larger than expected, because less tax was withheld ...
Decisions and taxes
Exercising stock options: how the taxes work, with an example
When you exercise options, and when you sell the shares, can change how much you keep. Here's how the main choices work, with a simple example.
Equity basics
ISOs, NSOs, RSUs, and RSAs: what you actually hold
Most equity decisions trace back to one question: what kind of equity do you actually have? The four common types can look similar on a statement, but they ...
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