A deceased man bursts through the doors of his own funeral and starts beating his wife for not crying hard enough over his fake death. That scene captures Timothy Dexter, an 18th-century Massachusetts tanner who built staggering wealth on investments so foolish his rivals suggested them as cruel jokes.

We trace his rise from farm laborer to basement tradesman, his bet on worthless Continental currency, and the export schemes that should have ruined him: bed warmers, wool mittens, coal to Newcastle, and cats to the Caribbean. Every joke turned to gold. We also cover his gaudy mansion, his fake titles, and his punctuation-free book, asking whether he was the luckiest fool or a shrewd contrarian.

• How buying depreciated Continental currency made him fabulously wealthy
• Why bed warmers sold as ladles to the West Indies molasses ...