Go Ahead!

Where I was brought up, we never talked about money.¹ There was not enough money in the place to furnish a topic of conversation.

Mark Twain

Financial advice has a past.

It doesn’t teach what you might think. The real lessons of history can change your financial life . . . they profoundly transformed mine.

From Benjamin Franklin to TikTok influencers, what “everyone knows” about money rarely stayed the same. Parents once taught youngsters not to save. Debt, meanwhile, was normal, necessary, and sometimes even a moral obligation. Before they were “good for the long run,” stocks were mostly for suckers and considered terrible long-term investments. Everyone says career comes first today, but marriage was the top money tip for most of American history. Timeless truths about wealth rarely lasted long.

One thing stayed the same. In each generation, loud voices assured Americans that no one gets ahead anymore.² Yet, from crisis to crisis, century to century, using made up money to greenback dollars to digital currency, Americans figured out how to move forward anyway. Some failed. Many more succeeded.

Today we say someone is “getting ahead,” but in the past their verb was bolder: “Go Ahead!” It was a common phrase, like a nineteenth-century internet meme. Go Ahead meant move, now, specifically to a better place than you began. Sometimes that meant physically going where the opportunity was, other times to grow where you were planted. But it always meant ending with a better life than you started with.

Go Ahead rarely had a number. It meant rich in the way everyday people mean it today—to rise from always needing more to having more than you ever needed. People worked, read, and dreamed about how to Go Ahead for 300 years.

Go Ahead was never easy, but it has gotten easier. There was no golden era when getting rich was a cake walk. If that era existed, you may be living in it now. The central argument of this book is that getting ahead has never been easier than it is today.

You won’t hear that from any social media or political campaign telling you everything, everywhere is getting worse. They’re wrong.

I know. It happened to me.

* * *

Where I come from, things got better every day. My mother was the sixth child born into a house with no toilet. Her parents eventually installed one ordered from the Sears catalogue, paid for by planting an extra field of peas. My father universally hated rich people, which was odd because he didn’t like other poor people, either. Both parents shared a healthy skepticism of those who tried to get ahead. They focused on not falling backward.

In the pre-NAFTA working-class South, everyone I knew existed one generation removed from farming. To have any good job was to stand apart from the “lintheads,” many related to us, working the ubiquitous small mills. A simple hierarchy was embedded in mundane architecture. At the bottom, people lived in mobile homes or clapboard “shotgun cabins,” so-called because a shotgun shell fired through the front door wouldn’t have time to expand before exiting the back one. Who tested this I do not know. At the other end of the success ladder were those who had two-story houses.

That was it. The rich lived across town in two-story houses and their kids had their own bedrooms. My father was brought home from the hospital to a mobile home. I grew up in a stick-built ranch sans garage precisely seven houses from where the gravel turned to dirt and the dirt turned to trailer parks. Three houses the other direction was a county road dotted with shotgun cabins. Whichever way we turned, we were a few very important steps from the bottom.

My father inspected buildings for the county, crawling beneath houses to examine electrical wiring. My mother was a secretary. The whole family story was one of inching ahead. After all, we peed in a flush toilet.

The person who made sense of this was my grandmother, ubiquitously called Maw Maw, pronounced like two cat’s paws, and in all ways the true wielder of family moral authority. “There are good poor people and bad poor people. We are good poor people,” she explained more than once. “The bad ones aren’t worth the cost of the gunpowder it would take to shoot ’em.”

My family is what Hillbilly Elegy would be if no one used drugs or drank booze. Moralistic? Maybe. But when you live on $14,000 per year, which is what my dad made, there are compounding returns to living without addictions. In the rush to label the Scots-Irish people of Appalachia³ as a Born Fighting dysfunctional clan of rednecks ready to drink liquor and settle scores, we’ve forgotten the born-praying Presbyterians like Maw Maw with no patience for such shenanigans who, with white knuckles, held the social fabric of the poor South together for 200 years.

Parents didn’t dream of getting rich. They prayed their kids would stay out of trouble. The marginal gains from morality could boost your chances of not falling backward. Of my two best buddies at graduation, one joined the Marines and the other went to federal prison. Tiny tailwinds gave me my on-ramp to academia, while friends hit the turbulence of drugs, drunkenness, and divorce.

I never had money, so I didn’t care much about it. After high school, I left home and lived in a singlewide with a rotted floorboard in front of my bedroom. We took a staple gun to the carpet and secured it to the wall, providing an extra second of warning before falling four feet to the ground below. I wasn’t ashamed of this. It was an ingenious use of a staple gun.

From the ages of eighteen to thirty-four, I rarely made more than $30,000 a year, usually while working two jobs. I was almost old enough to run for president, with a negative net worth and no idea it mattered. I loved history, and history loved me back. I became a professor. The doors of archives across the globe opened for me, and 300-year-old ink smudged my fingers. Me—a kid from Nowhereville, South Carolina—managed to get a college degree, make friends with winners of illustrious awards, and visit the flush toilets of some of the world’s most prestigious universities. Student loan debt seemed like a reasonable price to pay.

I came to study financial history by accident, largely because I lived through, and narrowly escaped, the 2008 financial crisis. While starting my doctoral dissertation, my wife and I were offered a no-money-down mortgage to buy a tiny townhome. Back then the “lesson of history” was supposedly clear: renting was throwing your money away. So, we took it. Who in their right mind approved such a loan never occurred to me. This was 2006.

Two years later, we agreed to take a financial class hosted by a local church. I only went because the teacher, a friend, was scared no one would show up. The next night, I could not sleep. Even with no formal training about money, I could tell we had none, owed more, and somehow owned . . . a house? We immediately put our townhome on the market, and it sold—for a profit. Our neighbor listed her home for sale one week later. It was too late. The housing crash was here.

We were the last people off the financial Titanic in 2008. As the world collapsed around us, friends lost jobs, and families tightened belts, I wrestled with how I knew so much history, but it helped so little. Saved instead by sheer luck and the commonsense rules of thumb taught in church basements, I had to know more.

The first financial book I ever read was Dave Ramsey’s The Total Money Makeover. The second was Rich Dad, Poor Dad. The third was on getting rich in stocks. The fourth was about how to buy houses with no money down. The benefit I had was reading these during the 2008 financial meltdown. It felt like watching the wedding video of a couple who dies on their honeymoon. I found it darkly fascinating that so many people believed so much of this stuff.

I became obsessed, reading gimmicky get-rich-quick ads of the Gilded Age, land brochures from the 1700s, boring insurance pamphlets from World War I, really anything I could get my hands on. I traveled to hotel lobby seminars late at night, where would-be wealth gurus told folksy tales of their success and promised people desperate to believe that they could, too. I watched in horror as people rushed, rushed to tables and fought for places in line to pay—often with credit cards—for courses on how to change their family tree forever. I signed up for online classes, traveled to no-money-down real estate trainings in trailer parks, met with Avon ladies and multilevel marketers, interviewed famous radio and tv hosts, and generally made it my life’s work to understand all the ways Americans tried to get by and get rich. I am proud, and my wife is ashamed, that I own one of the world’s largest libraries of obscure financial books like How to Buy God’s Mutual Funds and Profitable Mobile Home Investing Made Easy.

Anthropologists know there is a danger in immersive research. Study cocaine long enough, and you just might sniff a line. I certainly did. I have tried (with small sums) nearly every stock market trick there is. In my favorite experiment, I simply shorted every stock that CNBC’s Jim Cramer suggested buying on his show. I nearly broke even. Usually, I lost money on these exercises, which I thought proved the point.

I began as a pious cynic, documenting the rich stealing from the poor. It felt good to be a sanctimonious Robin Hood, mocking the wealthy with my research. A decade, though, is a very long time to argue against the evidence. Everyday people really did get ahead. The more successful people I met—in person and in the past—the less sure I became. The age-old question ate at me: If you’re so smart, why aren’t you rich? So, I stopped playing games and decided to use what I knew about history to make a million dollars.

To everyone’s astonishment, it worked. Along the way I founded a cryptocurrency, picked a fight with Thoreau, invested in moon land, nearly faced bankruptcy, made millions of dollars, retired early . . . and did this, ladies and gentlemen, without a single instance of using the word unprecedented.

To this day, no one is more surprised than me.

* * *

In the chapters that follow, we’ll explore financial concepts in the past and the present—how financial ideas changed, what they looked like in the lives of everyday Americans, and how so much of what we think is long lasting is surprisingly new. These insights are practical, so each chapter ends with takeaways making their past useful for building your future.

The point of this book is to share everything I discovered researching the Go Ahead American story. To show you what worked and what didn’t—for them, for me, and more importantly, for you—I experimented with each idea on myself, with hair-raising and occasionally hilarious results. In the end, it was worth it.

Go Ahead is as real today as it was back then, so why not give it a try? If we’re going to explore this legacy, we might as well learn how to get rich in American history.