Startup equity & liquidity

The wealth question only founders have: what your equity is really worth, and how to turn some of it into money you can live on, responsibly.

What founders use for startup equity & liquidity, ranked by how many answers lean on 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 In 11 answers
  2. A calm explainer of what a secondary actually is, who has to approve it, and how the price gets set, before you raise it with... Carta Article How secondary sales work at private companies Carta In 10 answers
  3. The most thorough plain-language reference on vesting, cliffs, strike prices, and exercise windows. Read it once and stop being... Holloway Guide The Holloway Guide to Equity Compensation Holloway In 8 answers
  4. 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 In 7 answers
  5. 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 In 6 answers
  6. 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 In 6 answers
  7. The best reminder that avoiding ruin beats chasing returns, and that wealth is the money you don't spend. The whole founder... The Psychology of Money Book The Psychology of Money Morgan Housel In 2 answers
  8. The India reference on short vs long term capital gains, holding periods, and rates for equity, funds, and property, so you... ClearTax Article Capital gains tax in India ClearTax In 2 answers

The questions

ESOPs, in plain English 11

What your options are really worth, and when you actually get to keep them.

What actually happens when my ESOPs vest? 3 → Do I owe tax when I exercise my ESOPs in India? 3 → My ESOPs look valuable on paper. Is that real money yet? 3 → What happens to my ESOPs if I leave the company? 3 → How do I tell if an ESOP grant in a job offer is any good? 4 → All 11 questions in ESOPs, in plain English →
Secondaries and taking chips off the table 10

Turning some paper equity into money you can live on, without signalling you have lost faith.

Should I sell some of my equity in a secondary? 2 → How much of my stake is reasonable to sell in a secondary? 2 → How does a founder secondary actually happen, mechanically? 2 → Will selling in a secondary upset my investors? 2 → How is the money I get from a secondary taxed in India? 2 → All 10 questions in Secondaries and taking chips off the table →
eChai Partner Brands The partnership →