Avoid Catastrophic Loss

If you can make one heap of all your winnings And risk it on one turn of pitch-and-toss, And lose, and start again at your beginnings And never breathe a word about your loss; (Location 871)

pretty much the opposite advice of Taleb and Naval:

The one thing you have to avoid is the risk of ruin.

Avoiding ruin means stay out of jail. So, don’t do anything illegal. It’s never worth it to wear an orange jumpsuit. Stay out of total catastrophic loss. Avoiding ruin could also mean you stay out of things that could be physically dangerous or hurt your body. You have to watch your health.

Stay out of things that could cause you to lose all of your capital, all of your savings. Don’t gamble everything on one go. Instead, take rationally optimistic bets with big upsides.

https://www.navalmanack.com/almanack-of-naval-ravikant/find-a-position-of-leverage

If only SBF and his Pirates of the Caribbean were more well-versed on the notion of catastrophic losses before they heavily leveraged their own crypto trading firm 202212170120.

Bankman-Fried's net worth peaked at $26 billion. In October 2022, he had an estimated net worth of $10.5 billion.5 However, on November 8, 2022, amid FTX's solvency crisis, his net worth was estimated to have dropped 94 percent in a day to $991.5 million, according to the Bloomberg Billionaires Index, the largest one-day drop in the index's history.67 By November 11, 2022, the Bloomberg Billionaires Index considered Bankman-Fried to have no material wealth.

On December 12, 2022, Bankman-Fried was arrested in the Bahamas, pending potential extradition to the United States. An indictment of him before the U.S. District Court for the Southern District of New York was unsealed on December 13, revealing a range of charges for offenses, including wire fraud, commodities fraud, securities fraud, money laundering, and campaign finance law violations. Bankman-Fried faces up to 115 years in prison if convicted on all eight counts.

https://en.wikipedia.org/wiki/Sam_Bankman-Fried