...zero f*cks given.
(Yes, ASCII wasn't around in 1798.)
Luck matters, but deep down I think his luckiest break was having a great boat captain. The guy found profit in the most unlikeliest of places by improvising.
"August 17th, 1782. The idiot sent us to the West Indies with a boat-load of warming pans. It was only through my ingenuity and hustle that I was able to convince the locals that they would make excellent ladles - we actually managed to turn a profit! I can already imagine the smug look on Dexter's face when we tell him about this. I bet this will inspire him to send something even more idiotic next time, like wool mittens. Note to self, don't show him this journal lest he get any ideas."