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Option exercise

As explained in Tech Startup Toolkit

Option exercise is the act of using an option to acquire the underlying company shares at its strike price.

Option exercise is the act of paying a fixed strike price to turn vested stock options into company shares you own. Vesting earns the right to exercise; exercise completes the purchase. Until exercise, an option is only a promise of future stock. section 4.2 section 21.4.2

Keep these practical points in mind:

  • The strike price is fixed when the option is granted, so a lower strike price makes conversion cheaper if the company becomes more valuable. section 21.4.2
  • A typical grant vests over four years with a one-year cliff: nothing vests during the first year, then one quarter vests at the anniversary and the rest vests monthly. section 21.4.2
  • Leaving the company can create a short deadline—usually about 90 days—to exercise vested options, or they may disappear. section 4.2 section 21.4.2
  • Exercised shares can be sold only if there is a buyer; selling shares held for less than a year may make the profit taxable as income. section 4.2

A grant becomes ownership

Suppose an employee receives options with a strike price of $1 per share. After the first year of a four-year schedule, one quarter of the grant is vested. Exercising that portion means paying $1 for each vested option and receiving the corresponding company shares. The remaining options still require later vesting before they can be exercised. section 21.4.2

How Tech Startup Toolkit covers it

How deep it goes
Defines exercise, then connects it to vesting, strike price, expiration, departure deadlines, sale conditions, and taxation.
Examples
Uses four-year vesting, a one-year cliff, fixed strike prices, post-departure deadlines, and conversion from options into shares.
What it assumes
Assumes only a basic distinction between options and shares, while defining vesting, strike price, and exercise directly.
What you can do after
Apply option exercise by identifying vested options, calculating the strike-price payment, and checking expiration or departure deadlines.
How it connects
Connects option exercise with vesting, strike price, incentive stock options, founder shares, expiration dates, and percentage ownership.

This explainer was generated by Manning's knowledge graph from the text of Tech Startup Toolkit. The section links point to the parts of the book it draws on.