Rule 9: Take your biggest risks when you have little to lose.
When you face asymmetric risk, it makes total sense to be bold, to grab the opportunity at hand. At the extreme, when the downside is very low (or nonexistent, as in the ‘nothing to lose’ case) and the upside is really high, it’s actually riskier not to make the bold move.
By aiming to die with zero, you will forever change your autopilot focus from earning and saving and maximizing your wealth to living the best life you possibly can.
In the end, the business of life is the acquisition of memories.