P. T. Barnum

Phineas Taylor Barnum built the first great American entertainment fortune in the 1840s and 1850s. He bought a struggling collection in lower Manhattan in 1841 and turned it into Barnum’s American Museum, the most popular attraction in the country. In 1850 he gambled on importing the Swedish opera singer Jenny Lind for a U.S. tour, paying her $1,000 a night, and the venture made him one of the wealthiest showmen in America.

Then he ruined himself with a single bad investment. Trying to build an industrial district in East Bridgeport, Connecticut, Barnum lent heavily to the Jerome Clock Company and was tricked into signing a flood of notes that left him personally liable for sums reported in the hundreds of thousands of dollars. The company collapsed in 1856, and Barnum was effectively insolvent, his fortune wiped out and his name dragged through years of litigation and public mockery.

He clawed back through work and discipline. Barnum took his famous performer Tom Thumb on another European tour, delivered a popular lecture titled The Art of Money-Getting, and methodically paid down his debts. By the early 1860s he had bought back his museum and rebuilt his wealth.

In 1871, at the age of 60, Barnum entered the business that would make him a legend: the traveling circus. P. T. Barnum’s Grand Traveling Museum, Menagerie, Caravan and Hippodrome grew, through a merger, into Barnum & Bailey, the Greatest Show on Earth. He also served as mayor of Bridgeport and in the Connecticut legislature before his death in 1891, far richer and more famous than he had been before his fall.

Ulysses S. Grant

Ulysses S. Grant rose from obscurity to become the general who won the American Civil War and then a two-term President of the United States. Yet he had little money sense, and after leaving the White House in 1877 he was not wealthy. In 1880 he tied his name and savings to a Wall Street brokerage, Grant & Ward, founded by his son Buck and a young financier named Ferdinand Ward, who was hailed as the Young Napoleon of Finance.

Ward’s operation was a fraud, an early Ponzi scheme. When it collapsed in May 1884, it took Grant’s entire fortune with it. The former President, who had borrowed $150,000 from William H. Vanderbilt to try to save the firm, was left essentially penniless, his honor stained by association with a swindle he had not understood. Soon afterward he was diagnosed with cancer of the throat.

With death approaching and his family facing destitution, Grant did the one thing he could do: he wrote. Encouraged and ultimately published by his friend Mark Twain, whose firm offered far better terms than the publisher Grant first approached, he raced to complete his Personal Memoirs while the disease consumed him.

He finished the manuscript in July 1885 and died days later, on July 23. The memoirs were a critical and commercial triumph, earning his widow, Julia, royalties of roughly $450,000, an immense sum that secured the family’s future. The book is regarded as one of the finest military memoirs ever written, and Grant won his last and most personal victory from his deathbed.