Mark Twain
Although Twain seemed to be wealthy and had a rich spouse, his line of work wasn't exactly a payout. It was barely enough for the two of them to live comfortably. Twain's publishing company lost everything in 1894, and he was forced to declare bankruptcy. Slowly but surely, Twain's finances got back on track, but he then lost $30,000 from a shifty investment. He never made that money back...
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