Your RSUs are a treasury problem, not a windfall

Put this scenario in front of any finance leader as someone else's problem: a company holds 70% of its operating cash with a single counterparty, with no written limit, no review trigger, and no plan for what happens if that counterparty has a bad quarter. Every instinct in the room says the same thing — that's not a cash position, that's an incident waiting for a date.

Now look at the same finance leader's own balance sheet. A sizable share of net worth sits in employer stock — RSUs vesting on a schedule, maybe ISOs from an earlier stage, maybe a founder grant that's never been touched. It's the identical concentration they'd flag instantly in a company. They call it "my equity," and most years, nobody runs the number.

The math you'd never approve for a client

The reason the double standard survives is that RSUs don't arrive looking like a position — they arrive looking like compensation, a few shares at a time, taxed as income the moment they vest. Nothing about the mechanics signals "concentrated bet." But a concentrated bet is exactly what accumulates, quietly, across every vesting date you didn't actively manage.

It gets worse on a dimension a pure portfolio concentration doesn't have: correlation with your employment. If the company has a bad year, the stock drops and your job is often the next thing at risk — the two biggest line items on your personal balance sheet moving together, in the same direction, for the same reason. A treasury team would call this a correlated-risk problem and size it down on principle. On a personal balance sheet, it usually just sits there.

Why "I'll sell it eventually" doesn't survive contact with reality

The plan most people default to — hold the shares, sell when it feels like a good time — fails for the same reason informal review cadences fail everywhere else in finance. "A good time" is a judgment call made under exactly the conditions that make judgment calls unreliable: after a run-up, when selling feels like leaving money on the table, or after a drop, when selling feels like locking in a loss. Add blackout windows and insider-trading policies that remove your ability to act on your own schedule in the first place, and "eventually" quietly becomes "never, until a life event forces it."

A position size, not a feeling

The fix is the same one that works for company treasury: pre-commit to a rule before the emotionally loaded moment arrives, not during it.

• Set a ceiling, in writing, before you need it. A common range is 5–10% of net worth in any single employer's stock once you're past the early-stage bet-the-career phase — the exact number matters less than having one you chose on a calm day.
• Default to sell-on-vest, not decide-on-vest. Treating each vesting event as a default sale — with a deliberate decision required to hold, rather than the reverse — removes the recurring judgment call that's how concentration builds in the first place.
• Separate the tax-withholding problem from the investment decision. RSU vesting is a compensation event taxed as ordinary income; what you do with the shares afterward is a separate, investment decision. Collapsing the two into one mental step is how "I'll deal with taxes later" becomes "I never rebalanced."
• If you're an insider, automate it. A 10b5-1 plan executes your pre-committed rule on a schedule, which is the entire point — it takes the decision out of the exact windows where you're both most informed and most restricted.

A company that let 70% of its treasury sit with one counterparty wouldn't call that a position. It would call it an incident, waiting to vest.

Where it gets genuinely complicated

ISOs and AMT exposure, QSBS eligibility on early-stage grants, and illiquid private-company stock each add real complexity that a general framework can't responsibly resolve in a newsletter — those are specific, jurisdiction- and grant-dependent questions worth taking to a tax advisor who can see your actual grant terms. What doesn't need a specialist is the first decision: deciding, on a calm day, what percentage of your net worth in one company's stock you're actually willing to carry.

The number you're avoiding is the whole exercise

None of this requires predicting where the stock goes next, which is usually the reason the decision gets deferred — "I don't know if it's going up." The ceiling isn't a bet on the stock. It's a statement about how much of your financial life you're willing to have determined by one company's outcome, decided before the outcome is known. That's the same discipline applied everywhere else in this newsletter, aimed for once at the reader instead of the balance sheet they manage for someone else.