There are definitely beneficial tax/benefit implications to failing businesses in certain situations. (Similar to how if you suck at stocks, you get perks.) Not out of the realm of possibilities. Given that his early life had successes, it could very well be that he learned failure is more profitable. Given the silver spoon in his mouth, less possible he learned, rather than existed and bumbled into it. Either way, not someone to put a lot of stock in. When you're bootstrapped with a certain amount of money, as long as your accountants keep you from being an abject fool, you'll never be poor a day in your life. Like, if most Americans had somewhere around $5 million invested conservatively, (don't trust this number, random deep memory grab that may be in error, and based on current money in the last decade) they could live on the dividends (money generated) while never touching the nest egg, and live a normal comfortable life without working for the rest of their lives.
Failing a business is only profitable because of abuse of laws. Laws can be changed, and should be. Success should always be the goal.
There's legitimately an entire genre of CEO that exists in the USA just to go into a company and purposely destroy it, and collect a golden parachute exit payout, for example. Shouldn't ever exist.
Is it funny or sad that I know all this, yet I work my ass off to survive?
Surprised they are only now complaining that it resembles warehouse work, they were shitty to work for as a software engineer before "AI". Can't imagine what hellscape they are now.