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Strategy & decisions
RSUs
The RSU tax traps that hit in April, and how to dodge them
The flat rate your company withholds at vesting is almost always lower than what you owe, and that gap is just the first of the RSU traps. This is the complete field guide: the withholding gap, estimated taxes, the double-taxed 1099-B, short-term gains, blackouts, wash sales, acceleration, and the private-company bill on shares you cannot sell.
How to value an RSU offer against base salary
Discount the equity for vesting risk and volatility before you compare two job offers.
Restricted stock
Missing the 30-day 83(b) deadline (and skipping it on purpose)
The 83(b) election has a hard 30-day window and no late forgiveness. Miss it, or skip it, on early-stage stock and you can hand the IRS a tax bill that grows every year the company does well, on shares you cannot sell to pay it.
Restricted stock in an acquisition
When your company gets bought, your restricted stock can cash out, convert to acquirer shares, or roll into new vesting. Which one you get, and whether your unvested shares accelerate, decides what the deal actually pays you.
ISOs
NSOs
ESPPs
Is maxing out your ESPP worth it
With a real discount and a quick sale, an ESPP is often the highest-return benefit you have. This is the whole playbook: whether to max it, how to fund it, when to sell, and the rare case for holding.
ESPP vs 401(k): where should the next dollar go
Both are good. They do different jobs, and the order you fund them in can leave real money on the table. Here is the priority I use.
Keeping ESPP shares from concentrating your portfolio
The discount is real, but every share you keep stacks more of your net worth on the one stock that already signs your paycheck. Here is how to take the deal without taking the bet.
How to fund a maxed ESPP without the cash on hand
Maxing the plan means a chunk of every paycheck vanishes for months before you see stock. Here is how to bridge that gap without taking on risk that eats the discount.