De-risking concentration
Diversifying beyond your company
Turning the little liquidity you have into a portfolio that survives a bad outcome.
How do I start diversifying when most of my wealth is illiquid?
Diversify with the liquidity you can actually get, steadily, rather than waiting for one big exit. In practice that is three things: invest your ta...
Should I sell some shares in a secondary just to build a safety net for my family?
For many founders this is the single most sensible move, if the chance comes. A secondary lets you sell some existing shares, usually during or aft...
Where should the first money I take off the table actually go?
Boring, in the best way. The first money off the table is not for a hot stock tip, it is for security. A sensible order many people follow: first a...
How big should a founder's emergency fund be, and where should I park it?
A common rule of thumb is several months of essential expenses, and founders often lean toward the higher end, say closer to a year, precisely beca...
Should my diversified money try to beat the market, or just track it?
For money that is your safety net, the honest answer is usually: do not try to be clever. You already carry enormous concentrated risk in your star...
Should I diversify into real estate, gold, or just index funds?
There is no single right answer, and the aim is not to chase the best return but to hold assets that do not all sink with your startup. Index funds...
How do I diversify out of my company without triggering a big tax hit in India?
You cannot avoid tax entirely, but you can be deliberate. In India, selling startup shares in a secondary or exercising and selling ESOPs generally...
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