it is if you have specific event driven knowledge that the put options would gain from but if you just buy deep out of the money put options every year, say 50

it is if you have specific event driven knowledge that the put options would gain from but if you just buy deep out of the money put options every year, say 50% price drop, in a 10b5-1 structure, its ok. you will get sued a bit more than usual not much different than buying life insurance, except if your company crashes like monday.com , some schmuck who sold you the puts will have to pay you a tonne of cash then you can do a dilutionary rights issue or just use the cash buy a boat in miami and start something else