How You Get Rich Isn't How You Stay Rich: 300 Years of Proof | Joseph Moore

A Note from James:

In 1790, one of the easiest ways to get rich in America was the old-fashioned way: marry someone rich.

George Washington did pretty well that way. Benjamin Franklin, meanwhile, was so deep in debt that he offered to marry a woman if her parents would mortgage their house to pay off his printing press debt. When they said no, he married someone else who had money.

And back then, debt was not just annoying. It could land you in debtor’s prison. Actual prison. And not just you—your wife and kids could go too.

Fast-forward to the 1900s, and most Americans still were not buying stocks. Only a tiny percentage owned shares. Everyday people were gambling, playing the numbers, using dream-interpretation books to decide what lottery number to play, and trying to find some edge that would move them a little closer to security.

My guest today, Joseph Moore, literally wrote the book on this: How to Get Rich in American History: 300 Years of Financial Advice That Worked (& Didn’t).

The book is full of strange, funny, surprising stories about money in America: Franklin, Washington, debtor’s prison, the Great Depression, bucket shops, real estate booms, FIRE, crypto, debt, index funds, and all the scams people keep falling for.

But the bigger lesson is that the basic patterns have not changed as much as we think.

People want security. People want freedom. People want hope. People want a way out. And whenever there is hope, there is usually someone selling a formula.

Joseph has very little patience for the usual personal finance myths. Debt does not make you rich. Opportunity makes you rich. Real estate is not always a magic wealth machine. The stock market was not designed to be everyone’s retirement plan. FIRE can work, but it can also become the CrossFit of personal finance. And optimism, marriage, mobility, risk, and solving other people’s problems may matter more than almost anything else.

If you think the rules for getting rich have changed completely, this conversation may convince you how little human nature has changed.

Episode Description:

Joseph Moore joins James to talk about the long, strange history of getting rich in America.

His book, How to Get Rich in American History, looks at 300 years of financial advice—what worked, what failed, what people kept repeating, and what today’s money culture keeps forgetting.

The conversation starts in 1790, with George Washington, Martha Washington, Benjamin Franklin, Stephen Girard, debt, leverage, and debtor’s prison. Joseph explains that many early American fortunes were built through risk, borrowed money, marriage, luck, and then—critically—de-leveraging over time.

That becomes one of the core lessons of the episode: debt does not make people rich. Opportunity does. Debt is only a tool that allows someone to grab more of an opportunity than they otherwise could. But if the opportunity is not real, or the person cannot handle the risk, debt destroys them.

James and Joseph then move into real estate. Joseph argues that real estate is a good way to build a modest middle-class fortune, but not usually the path to the biggest fortunes. In modern America, he says, real estate often functions as a short on the dollar, an income annuity in a low-dividend world, a tax shelter, and a way for ordinary people to use leverage they could not access anywhere else. But that does not make buying a house automatically smart. Renting versus buying depends on age, mobility, location, family needs, inflation, taxes, maintenance, transaction costs, and opportunity cost.

The conversation then turns to the stock market. Joseph challenges the usual historical charts that claim anyone could have invested a fixed sum in 1929 and held forever. Most Americans could not invest that way. There were no index funds, mutual f