Continuing the series of bullshit standard stories. This one is especially peculiar because it was firmly debunked a LONG time ago, then continued as truth.
Timothy Dexter lived around the time of the American Revolution. He was the Luckiest Entrepreneur Ever, held up as an example for youngsters who wouldn’t try new businesses. The official story tells us that he tried many different odd enterprises and made a fortune each time by being the first man to figure out the advantage. I heard about him on an episode of Strange as it Seems, which presented the whole story as true.
The official story was already debunked in the 1830s, but didn’t go away. Like ampersand, the reality is even weirder but NOT a fine example for young entrepreneurs!
Dexter was the Ultimate Troll. His first investment, arbitraging the debased Continental Currency, appears to be true though not lucky. He probably had inside knowledge of the coming revaluation. Using the money he bought a mansion and gathered a cult of dissolute youngsters who enjoyed his extravagant parties. At one point he “declared bankruptcy” and offered the mansion and its contents at public auction. The bankruptcy was fake and he continued living there. Later he held his own funeral and watched the mourners from his window. He hired a local poet as his Poet Laureate and graciously received the sycophantic poetry in his honor. He hired a sculptor to build giant statues in front of the mansion, mixing himself in with Franklin, Washington et al.
The mythical speculative ventures were written up in Dexter’s booklet, A Pickle for th Knowing Ones. He wrote the book without any punctuation in extravagant and inconsistent misspellings.
At the end he added an appendix:

He would have been right at home in modern social media, or a certain mansion in a certain national capital.
