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 funds had high fees, and buying an index directly required enormous capital. Instead, everyday people went to bucket shops, bet on price moves, played the numbers, and treated gambling as a kind of financial hope.
James and Joseph also discuss passive investing, shadow indexing, the rise of ETFs and 401(k)s, and the way the stock market has become a mass retirement promise. Joseph points out that this is historically new. For most of American history, no ordinary person would have expected to retire on the stock market.
From there, the episode moves to FIRE: financial independence, retire early. Joseph has lived part of that story himself. He built enough wealth through rental real estate after 2008 to stop working for a period, only to discover that early retirement was not automatically fulfilling. He compares FIRE to CrossFit: extreme, demanding, sometimes powerful, sometimes injurious, and not a lifestyle most people actually want.
The final section asks the big question: What has consistently worked?
Joseph boils the lessons down to five pillars: solve other people’s problems, take risks, move toward opportunity, marry well, and believe you can. James adds that optimism matters because it keeps people in the game long enough to get more shots on goal.
The result is a conversation about money, but also about history, risk, luck, marriage, mobility, discipline, scams, and the difference between getting rich and staying rich.
What You’ll Learn:
- Why early American wealth often involved marriage, leverage, luck, and risk.
- How George Washington’s marriage to Martha helped fund the Washington we remember.
- Why Benjamin Franklin’s public advice about debt did not match his own early financial behavior.
- What debtor’s prison meant in early America, including the risk to families.
- Why debt is a tool, not a wealth strategy by itself.
- Why opportunity—not debt—is what actually makes people rich.
- Why real estate can build middle-class wealth but rarely creates the biggest fortunes.
- How buying a home can reduce mobility and opportunity, especially for younger people.
- Why renting versus buying is situational, not a universal rule.
- Why most Americans historically could not invest in the stock market the way modern charts imply.
- What bucket shops and “the numbers” reveal about everyday financial hope.
- How passive investing changed the purpose of the stock market.
- Why stock-market concentration is not new, but mass participation is.
- Why FIRE can work mathematically and still fail psychologically.
- How older financial-independence stories often hid trust funds, inheritances, or outside support.
- Why inflation is one of the biggest risks to early retirement.
- Why getting rich and staying rich require different behavior.
- Why successful people often take risk early and reduce risk later.
- Why optimism is financially useful when it keeps people in the game.
- The five recurring pillars Joseph sees across American wealth-building history.
Timestamped Chapters:
[05:00] How to Get Rich in 1790
James asks Joseph how someone got rich in early America, starting with George Washington, Martha Washington, and marriage as a financial strategy.
[07:24] Stephen Girard and Benjamin Franklin’s Debt
Joseph compares Stephen Girard’s leveraged rise with Franklin’s messy early business debts.
[10:29] Debt Does Not Make You Rich
Joseph explains that opportunity creates wealth, while debt simply lets someone reach for more of that opportunity.
[11:23] Debtor’s Prison Was Real
Joseph explains why failing in the 1790s could mean prison not only for the debtor, but for the debtor’s family.
[12:25] The Real Estate Myth
Joseph argues that real estate can build modest wealth, but rarely creates the biggest fortunes.
[13:43] Real Estate as a Short on the Dollar
Joseph explains modern real estate as an inflation bet, income annuity, tax shelter, and leverage tool.
[15:22] You Need an Edge
James argues that every bet has someone on the other side, which means investors need to know what their advantage actually is.
[16:18] Beating the Market, Missing the Moment
Joseph tells the story of shorting Jim Cramer stock pops, beating the market net of theory, losing to fees, and missing his daughter’s first steps.
[19:56] Shadow Passive Investing
James and Joseph discuss hedge funds, index tracking, fees, and the way much of Wall Street quietly follows the same big benchmarks.
[20:31] The Index Revolution
Joseph explains why Vanguard’s 1976 index fund changed investing for ordinary Americans—and why passive investing may create new structural risks.
[24:24] The Four Percent of Stocks That Matter
James and Joseph discuss stock-market returns, T-bills, concentration, and why a small number of companies drive most gains.
[25:16] The Second Bank Crash
Joseph compares modern market concentration to the 1830s, when the Second Bank of the United States made up a huge share of the stock market before collapsing.
[26:21] The Stock Market as a Retirement Promise
Joseph explains why turning the stock market into a mass retirement strategy is historically new.
[29:58] The Problem With “The Chart”
Joseph criticizes the classic financial-advisor chart that assumes someone in 1929 invested a large sum, held forever, and never touched it.
[31:17] Bucket Shops and Playing the Numbers
Joseph explains how everyday people used gambling, bucket shops, and lottery-like games as financial hope when stock ownership was out of reach.
[34:04] The Mean Moves Through Time
Joseph explains why history is not physics and why the “average” keeps changing as the economy changes.
[35:49] Renting vs. Buying
James and Joseph debate the homeownership myth, maintenance, taxes, transaction costs, mobility, family stability, and when buying can make sense.
[41:02] FIRE and the Question of Enough
James asks how much is enough in 2026, and Joseph explains why the answer depends on location, expectations, security, and lifestyle.
[44:24] FIRE as the CrossFit of Personal Finance
Joseph compares FIRE to an extreme discipline that can work for some people but injure others if they push too hard.
[45:38] Geoarbitrage and Selling the Dream
James and Joseph discuss moving somewhere cheaper, Instagram FIRE influencers, and the difference between living the dream and monetizing the dream.
[46:00] The Long History of Financial Independence
Joseph traces earlier versions of FIRE through Sylvester Judd, Thoreau, Emerson, and Helen and Scott Nearing.
[49:17] Inflation and the FIRE Risk
Joseph explains how Your Money or Your Life and bond-heavy financial independence strategies ran into changing interest-rate realities.
[50:23] Five Pillars of Getting Rich
Joseph lays out the durable lessons: solve problems, take risks, move more, marry well, and believe you can.
[53:43] Marriage, Optimism, and Staying in the Game
James and Joseph talk about supportive partnership, optimism, savings discipline, and why staying in the game increases opportunity.
[56:11] The Line Between Optimism and Recklessness
Joseph distinguishes productive optimism from gambling and explains why control over outcomes matters.
[58:28] Getting Rich vs. Staying Rich
Joseph explains why many wealthy people take risk early, then de-lever over time to keep what they built.
[01:00:00] Leverage, Trading, and the Guy Who Never Stops
James and Joseph discuss extreme leverage, Bitcoin futures, Jesse Livermore, gamblers, and why some people cannot walk away.
Additional Resources:
Joseph Moore - History Helps
How to Get Rich in American History - Book Page
How to Get Rich in American History - Google Books
Next Big Idea Club: “The Changing Rules for Getting Rich in America”
Fast Company: “How the rules of getting rich in the U.S. change with every era”
The Motley Fool Interview with Joseph Moore
Meb Faber Show Interview
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