Guide

The Holloway Guide to Equity Compensation

Holloway Free Intermediate

The most thorough plain-language reference on vesting, cliffs, strike prices, and exercise windows. Read it once and stop being confused by your grant letter.

Open on holloway.com ↗

Curated reading that points you to the sources, not personalised investment advice.

It answers 10 questions

  1. What actually happens when my ESOPs vest?
  2. Do I owe tax when I exercise my ESOPs in India?
  3. What happens to my ESOPs if I leave the company?
  4. How do I tell if an ESOP grant in a job offer is any good?
  5. My net worth is almost all startup equity on paper. Is that real wealth or not?
  6. What happens to my ESOPs when the company gets acquired?
  7. How do I track my startup ESOPs and equity alongside my mutual funds and stocks?
  8. What is a strike price, and why does it matter for my ESOPs?
  9. Should I exercise my ESOPs early, and does that actually save tax?
  10. My ESOPs are in the US parent company, not the Indian entity. What changes for me?

Read with it

  1. A plain-language India primer on what an ESOP actually is, how vesting and exercise work, and how it is taxed. ClearTax Article What is an ESOP? Meaning, taxation, and how it works ClearTax
  2. A working glossary of the words on your cap table, from the company that stores most of them, so the jargon stops getting in... Carta Article Equity 101 for founders and employees Carta
  3. The India-specific piece: perquisite tax at exercise, capital gains at sale, and the startup deferral, with worked examples in... ClearTax Article How ESOPs are taxed in India ClearTax
  4. The clearest short piece on how to think about giving up and holding equity, and why a smaller slice of a bigger outcome is the... paulgraham.com Essay The Equity Equation Paul Graham
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