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From Zero to Side Hustle
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When you get a letter from the IRS…
🎲 Monopoly started as a warning. Lizzie Magie patented The Landlord’s Game in 1904 to show how rent piles up. Decades later, the version everyone knows turned it into a race for Boardwalk.
Most people take the wrong lesson from it and chase the expensive squares. The real game is collecting small rents again and again. Boring, cheap, frequently visited beats flashy more often than you’d think.
Those are the squares we like to write about.
Roll the dice.
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The Party Game People Print At Home
WHAT’S THE PROBLEM?
Whoever hosts the baby shower, the bachelorette, or the office Christmas party needs a game by Saturday. They don't want to invent one, and they won't wait for shipping.
A printable fixes that: pay a few dollars, download a PDF, print it at home.
That's the gap: hosts want a ready-made game tonight, and they don't want to design one.
WHAT’S THE BIG IDEA?
Design a game once in Canva, like a Christmas scavenger hunt, and list it on Etsy for $4 to $8. After that, every copy costs almost nothing to deliver.
The business makes money on each download. But it grows from the number of listings.
►Rachel Jimenez opened her Etsy printables shop in 2019 on maternity leave, selling party games and budgeting pages. It brought in about $160,000 in 2021, and she left her full-time job that June.
Zooming out: every holiday and party theme is another listing
A newer seller, Cody, wrote on Making Sense of Cents that he listed 350 printables in four months and hit $1,000 a month by day 116. Think: gender reveal games, retirement trivia, classroom bingo.
🥢The winners will be the sellers who go narrow. Cody's best listings were oddly specific, like a "school bus driver thank you card." One listing per exact occasion beats one generic game.
🍜The risk is that printables fade. Rachel's Etsy revenue fell from about $160,000 in 2021 to about $110,000 in 2022 and roughly $77,000 in 2023. You have to keep adding listings just to hold your ground.
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What's your take?
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Why Sandra Boynton Picked A Tiny Card Company
Most artists who license their drawings aim for the biggest company that will say yes. Sandra Boynton's greeting cards show why the right first licensee is often a small company that needs you.
What they uncovered: In the early 1970s Boynton met Recycled Paper Products, a young Chicago card company, at a New York trade show and signed a long-standing contract to design for it. Her "Hippo Birdie Two Ewes" birthday card has sold more than 10 million copies, and nearly 500 million of her cards sold between 1973 and 2003.
The usual mistake is treating the first license as a trophy. A giant company has thousands of designs to push, and an unknown artist's work can disappear into that pile.
Recycled Paper was the opposite. Two former Amherst roommates, Phil Friedmann and Michael Keiser, started it in 1971 to sell cards printed on recycled paper, and it was one of the first card companies to put the artist's name on the card. Boynton's hippo card became so identified with the company that people knew it by that name.
The company grew with her. Sales passed $20 million a year by 1981 and reached $100 million by 1991. She was never one artist in a catalog of thousands. She was the look people bought the cards for.
What they learned: When you license anything, whether a design, a name or a character, the first partner decides whether anyone ever learns it's yours. Pick one small enough that your work is its main product, and get your name on the product in writing.
The first licensee isn’t "a big brand." It’s the small company that just took it’s first booth at a trade show and still needs a signature look.
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House Window Washing, All The Way Down
Window washing is cleaning the glass on people's homes, inside and out, for homeowners who can't or won't get on a ladder.
What it costs to start: About $100 of supplies: an 8-foot pole, a squeegee, a brush and soap. The ladder is the real purchase; one local company requires its subs to bring a 28-foot extension ladder.
What you charge: Homeowners pay a national average of about $266 per job.
What a job costs you: Soap, gas and a few hours.
What's left per job: Close to the full $266, a very good morning.
🧮 What breaks it: The calendar. Final Touch Home Care, a Chicago-area company, pays window techs $500 to $800 a day, and only spring through fall is busy.
Earning $800 a day alone means three $266 houses every working day, more than 60 customers a month. So what fills the other hours? Finding those customers, then finding other work when winter comes.
Before you buy the ladder, see if you can book ten houses on your own street for next spring. Those ten names are worth more than the gear.
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Hungry yet?
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Enough talk. Go cook.
That's the plate. Reply and tell us the strangest thing anyone ever mailed you. Forward this to whoever is stuck hosting the office Christmas party this year. See you tomorrow.
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