Chapter 2

Reading Your Offer Letter Like a Pro

The numbers that actually matter, vesting schedules, the exercise window gotcha, and what your percentage really means.

What you’ll learn

  • The share count trap — why raw numbers are meaningless without context
  • Total shares outstanding and how to calculate your real percentage
  • The post-termination exercise window (90 days vs. extended windows)
  • Vesting cliff and schedule — what to negotiate
  • Double-trigger acceleration and why it matters in acquisitions
  • Questions to ask before signing

Most offer letters are designed to make equity look appealing without giving you the context to evaluate it. You'll see a share count — say, 50,000 options — with no reference to total shares outstanding. You'll see a strike price but no current 409A valuation. You'll see a vesting schedule but no mention of the exercise window when you leave.

Here's how to read past the marketing and find the numbers that actually matter.

In this chapter, you’ll work through the exact framework for reading your offer letter like a pro. We cover each of the key topics with worked examples, real numbers, and actionable steps you can take immediately.

  • The share count trap — why raw numbers are meaningless without context
  • Total shares outstanding and how to calculate your real percentage
  • The post-termination exercise window (90 days vs. extended windows)
  • Vesting cliff and schedule — what to negotiate
  • Double-trigger acceleration and why it matters in acquisitions
  • Questions to ask before signing
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This chapter is part of the full guide

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Equity Decoder

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12 chapters. 38 pages. An equity calculator. Everything you need to decode any offer.

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