Asymmetric Trades

Also known as unbounded success with limited downside.

Something that takes an hour, but impacts you for life. Unbounded upside, capped downside.

E.g. Typing. It takes around 4 hours to double your typing speed, for free. 4 hours for dividends for the rest of your career. (More productivity for 90,000 hours.)

The classic comeback to this: “Voice to text exists”, or “Typing isn’t really that big of a game changer.”

You’re trading 4 hours for optionality. The typing skills may never come in handy, but your downside has a maximum cap of 4 hours. (Unlimited upside.)

What other time trades do you have a limited downside on, but potentially massive return? A good book takes years to write, but can be consumed in a matter of hours. Someone already collected all of the experts, condensed their views, and presented them to you in a short format.

I'm trying to see this in more areas, so here are some examples:

  • Buying $100 in Put options on SPY. Will likely expire worthless, but have a 1000x potential return. This is a hedge against my main portfolio.

Update in 2022 - This is highlighted in Taleb’s

. How can we have maximum exposure to upside with limited exposure to risk.


Creation time ≠ Consumption time.

What if I hunt for content that takes the maximum amount of time to create, but minimum amount of time to consume? Probably results in watching rich/well producted Tik-Toks.