Articles on stock options — ISOs vs NSOs, exercise strategies, tax treatment, and how to time your exercises to minimize AMT and maximize after-tax gains.
15 articles
AMT is driven by the ISO bargain element, so the way to avoid triggering it is to control that number — exercise to your break-even, spread exercises across years, and time disqualifying sales. Here are the levers in dollars.
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A comprehensive overview of all equity compensation types --- stock options (ISOs and NSOs), RSUs, restricted stock, phantom equity, SARs, and profits interests. Covers how each is taxed, when companies use them, and which you are most likely to receive at each company stage.
A comprehensive comparison of RSUs and stock options covering how each works, risk profiles in up/flat/down markets, tax timing, exercise costs, and which is more common at different company stages.
A detailed comparison of Incentive Stock Options (ISOs) and Non-Qualified Stock Options (NSOs) covering tax treatment at exercise and sale, AMT implications, the $100K annual limit, and holding period requirements.
A disqualifying disposition is selling ISO shares before meeting the holding period. Learn the two requirements, tax consequences, and when selling early is actually the better strategy.
Your strike price determines your profit when exercising stock options. Learn how companies set it, the role of 409A valuations, what happens when options go underwater, and the tax implications.
Optimize ISO exercise timing across 3-5 years
