In this segment from Motley Fool Answers, Robert Brokamp interviews Alan Pell Crawford, author of How Not to Get Rich: The Financial Misadventures of Mark Twain.

They discuss how Samuel Clemens, one of 19th-century America's greatest authors and cleverest wits, repeatedly made a ton of money, and then repeatedly made bad business decisions that lost it all for him. He saw big possibilities for American manufacturers in a product that eventually became one of South America's major exports. He also headed out West to seek his fortune mining silver -- and came ever so close to striking it rich.

A full transcript follows the video.

This video was recorded on March 20, 2018.

Robert Brokamp: One of the first business pursuits Mark Twain tried, as I understand it, was to corner the world's cocaine market.

Alan Pell Crawford: Yes. I don't think he was 18 or 19 years old at the time, and there was a book of an American explorer who went to the Amazon. [He] observed the silver mining operations going on down there, and how these indigenous peoples could work endlessly with no food. They didn't seem to get tired. They were in very cold streams wading around -- and they were chewing a leaf of the coca plant. This man observed this, and Twain got this brilliant idea. He could see, I think, a tremendous market for this elixir that if you're running a textile mill in New England or something, and you want your workers to work uncomplainingly, all day and all night...

Brokamp: Cocaine's the answer.

Crawford: Yes, here it is. So, he decides he's going to take a ship from New Orleans to the Amazon and get it all figured out, and then his brother will join him. They'd have a monopoly on this product and ship it to Europe and the United States. Unfortunately, he gets to New Orleans, he runs out of money, and he also learns that there are no ships leaving from New Orleans to the Amazon and there wouldn't be, they said, for another half century, at least. So, he decides, "Well, I need to find a new occupation." That's how he ended up talking his way onto a job as a cub riverboat pilot on the way back north on the Mississippi.

Brokamp: I assume this is where he comes across the term that means water is deep enough to be safe, which means it's two fathoms deep, and that term is...?

Crawford: "Mark twain." At some point -- and scholars disagree about this and there are various theories -- he began to use the byline "Mark Twain," which does have the river usage that you're referring to. There was also another man that wrote a few pieces for one of the New Orleans newspapers who was himself on the river and used that byline first.

Brokamp: Oh, really?

Crawford: Yes, so plagiarism on top of all the other mistakes.

Brokamp: So, he has to pay $500 to be an apprentice on the riverboat. The problem with that situation is the Civil War breaks out.

Crawford: Yes. He was making a fair amount of money as a very young man in what was a glamorous occupation. The riverboats we think of as being kind of quaint. This was the glamorous thing to be doing. Twain did very well as a young man as a riverboat pilot. He loved the work and thought he would do it for the rest of his days.

Then something unfortunate happens, which was a war comes and shipping on the Mississippi River shut down. He knew about it, but let's say it became very vivid when he and another pilot friend were nearing St. Louis and their boat gets fired on by Federal artillery. Twain's just a passenger up in the pilot house when his friend is at the wheel. A shell hits them and stuff goes flying, and he says, "Sam, what do you think that means?" and Twain says, "I think that means they want us to slow down a little."

Twain then takes the wheel and heroically maneuvers the thing into safety, but that's the end of his piloting. In fact, according to his sister's account, he was scared to death that he was going to be impressed into the Union Army as a pilot on gunboats, and that they would shoot him at the least sign of a misstep.

At this point, again, he says, "I've got to find a new livelihood." And like thousands of other American men who didn't want to get shot, he left for the Nevada silver mining boom with his brother who was appointed to a government post out West.

Brokamp: So, he does some pretty dirty work, there, for a while. He and a friend do get the rights to a blind lead to some silver. Basically, they blew it.

Crawford: Yes. They stumbled onto a vein of silver that they could lay claim to. It was running through another company's claim that could shut this down. They had, I think, 10 days to do some very minimal work to make this claim theirs, legally, where everything had to stop and they got to go in there and make their millions.

When they discovered this, they sat up all night talking about what they were going to do with the money. They were going to spend a year and a half traveling in Europe. They were going to build mansions in San Francisco. Twain knew exactly where the billiard table was going to be and what his liveried servants were going to wear. In great detail they figure this out and then they don't communicate properly. One goes off in one direction and Twain goes out to visit a sick friend, and by the time they come back, they left notes for the other one on what you're supposed to do to work this claim so it's permanent and it's ours, and unfortunately neither of them got the other's note and, as Twain says, "I was a millionaire, there, for an hour or two, and now I'm poor again."

It's one of the early financial calamities. Again, I think what's wonderful about this is everybody who reads this will say, "Oh, my favorite time was when X happened," and in part because there's an irrepressibility to his personality. Nothing discourages him. Temporarily it does. There are periods when he can't sleep, and he paces the floor, and he drinks too much, and he worries. But then something occurs to him that, "Oh, this is going to be it. This time I'm going to make a fortune." All that other stuff seems to have been forgotten. He moves forward.