If inflation is too much money chasing too few goods, causing a drop in the value of the money, a depression is the reverse: goods and services drop in value, and money rises. And the people who are badly affected by inflation do better in a depression, and vice-versa. People with debt benefit from inflation: assuming their interest rate is fixed , inflation corrodes their debt, makes it easier to get the cash to repay it. And in a depression, people with cash savings are in a better position than people in debt, because their money grows in value. One group who notoriously did worse in the Great Depression therefore were farmers. Farmers who grow crops, like wheat, corn, etc. typically have only one season a year where they have significant cash income, and so it has long been normal for them to use credit over the rest of the year, and was so in 1929. If they had a mortgage on their farms as well, that became a double problem, for not only was it harder to earn the cash to pay their mortgage , but because they had placed the value of their farm as surety against the loan of money, when the value of their farm dropped they were called upon to pay the difference in cash. Along with the people who were in debt, there were also investors, who'd put their money into other assets. And, unfortunately, anyone who put money into a bank at the time could also be counted as an investor, as it was before the FDIC guaranteed deposits. Banks then, like now, only had on hand a portion of the money deposited, and when the Depression hit, a number of them failed.

One example of someone with more cash and little debt was W.C Fields. Before he went into making movies, he'd been a very successful juggler in Vaudeville, and distrusted Wall Street. As he traveled around he seems to have had a habit of setting up small bank accounts in towns he played, which meant he diversified his risk: some of those banks failed, and some did not.( After his death, a legend grew that there had been hundreds of them, and under assumed names, but it turns out to have been 24 of them all under his own name)

But of course a Depression also results in a very slow economy. Even if you are sitting on a pile of money, it can be hard to earn more of it. In this, Fields was also lucky, because the movie industry was one of the few that did pretty well during the Depression: people wanted to escape their misery for a few hours of watching films. Fields therefore actually had a good Depression.

James Curtis : W.C. Fields