Why 'it kept going up' isn't a strategy — and the math that shows exactly how exposed you are.
Hold vs. sell scenarios modeled over 12 and 36 months: ordinary income, capital gains, AMT, and the traps between them.
10b5-1 plans, exchange funds, direct indexing, and charitable strategies — compared side by side, trade-offs included.
Turning a concentrated position into a funded life: what your equity can actually buy, and in what order.
What −30% and −60% scenarios do to your plans — and the specific first steps, with dates.
Written for senior ICs, managers, and executives with $500K+ in company equity — especially with a lockup expiring. Educational only; not individualized advice.
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