How to Decide How Much Company Stock to Hold (and Cap the Loss)
The 2-year test: how much company stock to hold so a 50% drop costs no more than 2 years of spending.
Continue reading →Exchange fund vs. selling stock: what a $1 million position costs each way
A staged sale beats a 7-year lockup for most $1 million positions.
Continue reading →What is risk capacity in investing, and how do you measure yours?
Most people assume an 'aggressive' questionnaire score means they can hold mostly stock, but that score only measures nerve.
Continue reading →Edward Jones Investments' Guide to ISO Exercise and AMT, With Real Numbers
Picture a principal engineer opening his tax software in February and watching a new form appear, with a bill he never saw coming.
Continue reading →How Edward Jones Investments Approaches the Checklist Before Leaving a Tech Job
ISOs exercised more than 3 months after departure lose their ISO status and get NSO tax treatment.
Continue reading →Holding ESPP shares for the tax break is the mistake that costs the most: ESPP mistakes to avoid
For ESPP shares it usually lists only the discounted purchase price, so the discount already on your W-2 gets taxed twice unless you adjust the basis.
Continue reading →When should I sell RSUs? A guide for engineers holding vested shares
Quick test: sell at vest any shares covering money you'll spend within 5 years, plus any tax still owed.
Continue reading →Questions for an Equity Compensation Advisor: The Edward Jones Investments Checklist
An ESPP sale counts as qualifying only after more than 2 years from the offering date and more than 1 year from the purchase date, and Medicare sets premiums from income 2 years earlier.
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