House Hacks and Side Hustles Before Uber and Airbnb

The gig economy, they call it.

Kids today label side jobs rizzidencies or grinding, which in my day was a very different thing. Renting rooms in your house is “house hacking.” Before 2013, the only historical use of that phrase combined a tame noun with a violent verb: he went through the house, hacking bodies. Now it is a financial strategy that rebrands “I have roommates” into wealth creation. There’s an app for all that, but the idea is hardly new. Everyday Americans had hustle culture from Day 1.

Boy did I need a side gig. I was in debt up to my credit limit, scrapping vacations for HVAC repairs, and generally trying to keep my poorly planned upward mobility from crashing down to earth. Out of the blue, my wife got a promotion that came with a non-negotiable move to Atlanta, Georgia. The promotion was terrific. The timing, not. I was up for tenure, so we hunkered down for a commuter marriage. Where does a forty-year-old man live alone?

I had just the thing, inspired by history’s investment guides. I would stay for free with roommates. I rented a small three-bedroom ranch near campus and sublet the other two rooms. It went so well, and I got so many applicants, I decided to rent my room, too. I slept on the couch for eighteen months and went to Atlanta on weekends. The idea came from history, but the motivation came from the fact that all my investment properties were losing money. For the first year, my only rental that broke even was the one with two grad students, a geography professor, and an award-winning historian sleeping on the sofa.

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The house-hacking label took hold on BiggerPockets.com, a website and podcast for novice real estate investors, around 2013. In this case, the game you hacked was financial freedom, and the cheat code was buying a house and renting the extra rooms to pay the mortgage. Hit a few buttons in correct order (FHA mortgage with 3 percent down, purchase a multi-family home, live in one unit, rent out the others) and boom! You win!

House hacking has its own tiny piece of the internet, at the corner of get rich with nothing and unconventional arrangements. It’s a four-plex. You can’t miss it. The idea has its own Reddit thread, with posts like “Roommate death,” asking if insurance covers removing the stench from a dead body.¹ Games don’t win themselves.

This rewarding roommate strategy is, yep, very old. American families have been renting rooms in their houses since the dawn of American families having rooms in houses. Before it was the cheat code for getting ahead, it was simply called “taking on a boarder.” As far back as colonial times, poor people house hacked to advance. The Summers family of 1760s Philadelphia “lived with Cordwainer Henry Birkey, his wife and three children, and divided the £18 annual rent,”² according to tax records. They were not the least bit unusual.

Immigrants were especially down with this strategy to pay for, pay off, and expand their homes. A social worker in early twentieth-century Chicago³ described recently arrived workers, earning $1.25 per day, who still “managed to lay a little aside for that longed-for possession—a house and a lot that they could call their own.”These families bought houses with little down and promptly rented out every room. After boarders helped pay down the mortgage, “then the house receives an additional story, and that was rented so that it began earning money.” Then they would expand again, this time adding rental rooms on the back and building “an imposing brick or stone structure” on the front to add curb appeal. Only after years of housemates would couples live in the nicest portion of their own homes, renting out the older rooms to pay for showpieces of American consumer culture: carpets, upholstered chairs, and a piano. These families found a shortcut on the difficult journey to the middle class.

This was no small phenomenon. In any given year before 1900, nearly one-third—pause over that . . . one-third—of all families took in boarders. Around half of American families were landlords at least once in their lives. Especially for young mothers stuck at home with little children, taking on boarders was a way to raise the family’s income. This money wasn’t free. Women’s labor came standard: laundry, cleaning, and meal prep were included.

Seventy percent of Lithuanian families in America had boarders in 1910, as did nearly 50 percent of Hungarian and Italian immigrants.⁴ By the early twentieth century in cities like New York and Pittsburgh, no less than 20 percent of all homes were renting rooms.⁵ Not just one. The typical immigrant household kept three to four renters at any given time.⁶

Why do this? Because the benefits were life changing. The lowest estimates suggest taking on boarders added 10 percent to family take-home pay. In Pittsburgh, immigrant and black families increased income by 30 percent this way.⁷ Families with renters were the most likely to have savings left over at the end of each year.⁸ In Detroit and Milwaukee, researchers found that nearly half of unskilled workers were able to afford their own homes only because they rented the rooms. For generations, house hacking was the primary American mortgage payoff strategy.

New York City policeman John Taylor and his wife, Agnes, became homeowners⁹ this way in the 1890s. Taylor had been a policeman for over a decade before they could finally afford the down payment on a brownstone at 152 Waverly Place for $17,500. For eight years, the couple lived on one floor and rented the others to nine men and a live-in maid. By 1900, with most of the mortgage paid down, they sold and bought 213 West 136th Street in Harlem, which they could afford all to themselves. As a 1905 newspaper commented, “Taking in boarders is one of the oldest and most respectable forms of adding to the income”¹⁰ for working people. Once they reached the middle class, most people put that chapter of life behind them, as the Taylors did.

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As homes became more plentiful and nicer, taking on boarders gradually subsided. But it wasn’t affluence that did away with the strategy. Progressive reformers killed it, campaigning against the crass “lodger evil.” Between 1880 and 1920, 18 million people arrived in the United States, many of them renting rooms, couches, and even space on the floor from other immigrants. Overcrowding concerns were genuine, but much of it was hyped by racist tirades. The same man who wrote The Clansman, a book and later movie in which the KKK were the heroes, wrote horror stories about evil immigrant boarders. Legislation soon followed. Night raids, landlord laws, and zoning combined to effectively make taking on boarders illegal in most cities. The shame associated with it (like single men around married women) made renting your rooms a mark of embarrassment instead of a badge of Go Ahead honor.

The idea reemerged in 1976 when Doreen Bierbrier, a single Peace Corps worker in D.C., decided to buy a bungalow and pay for it with other single gals. Discovering a shortage of rentals for young women, she moved out of the house, rented out her old room, and did it again. And again. In ten years, she purchased four houses in nice D.C. neighborhoods. Bierbrier’s how-to guides became mainstays of the self-taught real estate scene in the late 1980s and 90s. The game was being played, analog, and the cheat code still worked.

Tech met tradition in 2007 when San Francisco entrepreneurs began renting air mattresses in their apartments during design conferences, officially launching Airbnb.com a year later. The popularity of renting your dead space exploded and morphed into a full-blown investment strategy for buying dedicated short-term rentals. Blowback against Airbnb rebirthed many of the Progressive Era agitations against “the lodger evil.” Whereas people in the past lived with a housing shortage and saw renting as the solution, today our housing shortage (and the increasing trend of renting out entire homes) frames boarders as adding to the problem.

I’m of no political persuasion here, but I will say monetizing space probably helped your family climb to the middle class. If your great grandmother could do it, you shouldn’t be ashamed to try. Just be aware that municipal governments armed with ordinances have shut this down once, and if the political winds blow a certain way they will shut it down again. Those eagerly gobbling up homes for short-term rentals may learn the hard way that, as another chapter of this book says, the government was always involved.

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If roommate roulette isn’t your vibe, you can always grab a second income stream. What today are called “side hustles” were once called “tasks.” Side gigs and odd jobs monetized moments between harvests. Sons spent winters making shoes for local merchants. Bark was peeled for barrel making. Entire families spent their nights by the fire twisting hemp into strands of rope for sale.

In the 1840s a national craze for palm-leaf hats¹¹—big, broad forerunners of the cowboy version—meant women could work from home and make forty cents on the dollar of each hat’s sale. Three children once went on a hat-making spree and wove 800 in just over a month, earning two dollars per hat. As more and more families made them, the returns went down, but for a time it was as popular as driving for Uber.

The biggest hustles were butter and chickens. Around one dollar of every four earned on farms came from butter, mostly churned by women. Meanwhile, chickens were everywhere. A prize-winning essay in Good Housekeeping¹² assured readers that investing in a flock of thirty birds would, by year’s end, pay for itself through egg sales. This idea reoccurs to society every time there is an egg shortage, like in 2025.

As people increasingly moved to cities, it got harder to raise birds or keep cows. The new path was selling. In 1892, a former door-to-door book salesman transformed an army of women into independent shopkeepers minus the headache of a shop. “You get the same profit that the owner of a store receives,”¹³ he explained, without paying “rent, light, heat, clerk hire, and other expenses.” Top performers could even win a newfangled invention known as the automobile. His California Perfume Company later rebranded itself as Avon.

Avon’s concept of a sales force requiring no capital, no inventory, and setting their own hours as a path to self-sufficiency birthed the core concept that would drive the direct marketing boom. The appeal was broad. Two leading entrepreneurs of black women’s beauty products,¹⁴ Annie Malone and her one-time saleswoman Madame C. J. Walker, perfected the art of turning their best clients into agents for the company.

These were not yet the pyramid scheme we think of in the twentieth century. In fact, many black and white women made a respectable amount of money for their troubles via Avon and Walker. Many reported that their jobs helped make ends meet and gave them a way to save for major purchases. In its infancy, direct marketing was one of America’s best side hustles.

The appeal of selling your way to a better life grew larger at just the moment the returns got smaller. In the 1930s, a traveling businessman hit upon the idea of selling Chinese herbs to Americans. He recruited local enthusiasts to buy products from him wholesale to resell themselves. They weren’t salespeople, they were “distributors.” This turned loyal customers into his largest sellers, who in turn built a distribution pyramid beneath themselves of like-minded evangelists getting ever smaller cuts. The company was eventually named Nutrilite. It birthed multilevel marketing (MLM).¹⁵

By promising financial freedom, MLM companies unleashed a swarm of direct salespeople onto the American suburbs in the latter half of the twentieth century, selling everything from cookware to phone services to miracle cures. MLM tapped into something in the American soul. Possessing no capital, two generations removed from family farms, awash in a sea of consumer goods bought on credit, saddled with mortgages on homes they could no longer rent out, Americans had few outlets for the old desire to achieve independence. With eight-hour shifts and two-day weekends, would-be entrepreneurs turned their free time into hawking Tupperware parties to friends who didn’t want to be there, but didn’t know how to say no.

The returns for selling “soap and hope” are famously low. Ninety-nine percent of American “distributors” make no money after expenses. Even the top 1 percent of sellers rarely make more than minimum wage. For every pink Cadillac carrying a Mary Kay super seller, countless other dreamers are still driving the same clunker to trunk shows. How many? One in seven households have a MLM member, the overwhelming majority of them poor and likely to stay that way.¹⁶

Beware MLM companies. When your side hustle is scamming you, you will get happier results with more traditional routes: part-time jobs, roommate strategies, and so on. Heck, raise chickens. You’ll do better financially, and your friends won’t avoid you.