16 Timeless Business Lessons from The Simpsons

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The Simpsons is one of the most entrepreneurial shows on television. Throughout its more than 500 episodes, the characters engage in, and interact with, dozens of small business ventures.

(I was going to call this “Evergreen Business Lessons from Evergreen Terrace” — but I figured not everyone would recognize Evergreen Terrace as the name of the street where The Simpsons call home, AND not all of these operations are based there anyway.)

Their hometown of Springfield is Anytown USA, where the citizens participate enthusiastically in the local economy — including establishments like Krusty Burger, Lard Lad Donuts, King Toot’s Music Store, Luigi’s, the Gilded Truffle, Red Blazer Realty, The Android’s Dungeon, the Kwik-E-Mart, and of course Moe’s Tavern.

Homer works for the Nuclear Power Plant, but he’s one of TV’s most prolific side hustlers. He’s always got some new business idea or money-making scheme going on. He’s been a door-to-door sugar salesman, a baseball mascot, a food critic, a cartoon voice actor, a night manager at the Kwik-E-Mart convenience store, a grease re-seller, and even an astronaut.

His boss, Mr. Burns, offers this cynical advice to would-be entrepreneurs:

“Family, religion, friendship. These are the 3 demons you must slay if you wish to succeed in business.”

And while many of the businesses on The Simpsons do end up in failure, they leave behind a lesson plan more entertaining than any MBA program. Let’s study up!

1. Beware the Smooth-Talking Salesman

In The Call of the Simpsons (Season 1), Homer and the family visit Bob’s RV Round-Up to shop for an RV they can’t afford.

Even though the banner at the dealership reads, “We’d rather make a friend than a profit,” Bob recognizes a sales opportunity when he sees one, offering up a “Thank you God” as his unsuspecting victims walk onto the lot.

He goes on to explain all the luxury bells and whistles of the 2-story Ultimate Behemoth, and compliments Homer’s “god-like” features. Homer, trying to keep-up-with-the-Flanders’, is sold.

Thankfully, Homer’s less than god-like credit score prevents him from making the far-too-expensive purchase — and instead they settle on a more budget-friendly option.

The Lesson: In any sort of sales situation, do your own due diligence. The person you’re relying on for information may not have your best interest in mind.

2. Fixed Costs Can Kill You

In Bart Gets an Elephant (Season 5), Bart wins an elephant from a radio contest and names him Stampy. The family keeps the animal in the backyard, and Homer begins to sell elephant rides to the neighborhood kids for $2 apiece.

“Look at this Marge, $58 and all of it profit,” Homer exclaims. “I’m the smartest businessman in the world!”

Of course, Marge points out that Stampy ate $300 worth of food that day.

The Lesson: Profit = Revenue – Expenses. Homer forgot the expenses portion, and that was the difference between a money-making venture and one doomed to fail.

(He subsequently raises the price for an elephant ride to $500, and loses all his customers — another important lesson about price elasticity as it relates to demand.)

stampy the elephant

(image source: simpsons.wikia.com)

3. Deliver on Your Promises

In New Kid on the Block (Season 4), Homer sees an ad for all-you-can-eat seafood at the Frying Dutchman restaurant. He and Marge hire a babysitter and head out for date night.

Hours after the other restaurant patrons have left, and with Marge asleep at the table, Homer continues shoveling food into his mouth. Eventually the restaurant staff kicks him out, and he cries,

“But the sign said all you can eat!”

He sues the restaurant for false advertising, and they agree on a settlement in which Homer gets more food and the restaurant uses him as a marketing attraction — “Bottomless Pete: Nature’s Cruelest Mistake.”

The Lesson: Advertising messages are heavily regulated, so if you make a strong claim or guarantee, make sure you can back it up. It’s probably not worth the risks of upset customers and legal action to hype up marketing language to a point you can no longer deliver.

4. Play Your Own Game

In 22 Short Films About Springfield (Season 7), the Springfield police crew are enjoying lunch at the local Krusty Burger.

The conversation shifts to McDonald’s, a restaurant Chief Wiggum has never heard of, but is told has “over 2000 locations in this state alone.”

Krusty Burger doesn’t fear the competition because they have a loyal (and very sheltered) customer base. The police crew discuss the differences between the two restaurants and conclude they’re happy with the familiar fare of Krusty Burger.

Later, Krusty’s popular Ribwich sandwich draws a cult following that calls themselves Ribheads.

The Lesson: If your business idea is any good at all, competition is inevitable. But successful businesses don’t sweat their competitors; instead they focus on what unique value they bring to the table.

RibWich Commercial from ronno on Vimeo.

5. Protect Yourself

In Bart’s Inner Child (Season 5), the family scores a free trampoline. The kids are thrilled, and Homer’s entrepreneurial sense starts tingling.

He begins to charge their friends and neighbors for jumping time, and has visions of a larger backyard theme park.

But the trampoline proves to be dangerous, as many customers wind up injured. Lacking the safety equipment and liability insurance to stay in business, Homer has to shut down the fledgling operation.

His post-mortem includes an optimistic outlook typical among entrepreneurs:

“Okay, the trampoline was a bad idea. But you know what? At least I’m out there trying new things.”

The Lesson: Make sure you have adequate liability insurance and asset protection. Even if you’re not running a backyard trampoline business, you never know when someone in our super-litigious society will come after you.

6. Keep Your Team Happy

In Last Exit to Springfield (Season 4), the family discovers Lisa needs braces. However, Mr. Burns, in an attempt to cut costs at the power plant, has removed the dental plan benefits from the union contract — replacing it with a free keg of beer at the union meetings.

Eventually, Homer realizes if they approve the contract, he’ll have to pay for Lisa’s braces out of pocket. He is enthusiastically elected the new union leader and begins a series of negotiations with Mr. Burns.

Without an agreement, the power plant workers go on strike, and Mr. Burns eventually concedes to the union’s demands — and Lisa gets her braces.

The Lesson: If you take care of your team, they’ll take care of you. John Mackey, founder of Whole Foods, once said,

“Business is simple. Management’s job is to take care of employees. The employees’ job is to take care of the customers. Happy customers take care of the shareholders. It’s a virtuous circle.”

7. Don’t Chase the Latest Trends

In Das Bus (Season 9), Homer learns that his neighbor Ned Flanders has a thriving online business. Fearful of missing out on a lucrative opportunity, he begins his own Internet business, CompuGlobalHyperMegaNet — despite not having any idea what the company actually does. (“Hmm they have the Internet on computers now…”)

He explains to Marge, “Everybody’s making money off the Internet — except us!”

For a brief moment, it seems Homer will get a big cash payday when Bill Gates offers to buy out his company. Instead, Gates’ goons just destroy Homer’s office while Bill explains,

“I didn’t get rich by writing a bunch of checks.”

The Lesson: The technology or business trend du jour might look attractive, but if you don’t understand it, you’ll probably just spin your wheels. For instance, you’ll see websites with links to their twitter, instagram, and pinterest pages, but no activity on any of those platforms. There’s no rule that says you have to be involved in every “next big thing” — especially if it’s not relevant to your business.

8. Mind Supply and Demand

In Homer vs. the Eighteenth Amendment (Season 8), Springfield discovers a law on prohibition is still on the books. With alcohol now illegal, Moe disguises his tavern as a pet shop, and citizens turn to a bootleg supply from the mob.

Anxious to get in on the action, Homer sources a load of discarded beer from the landfill. He pours the beer into hollowed-out bowling balls, and through an elaborate series of pipes, delivers the goods to Moe’s.

Marge is impressed with his ingenuity and is happy with Homer’s new side hustle income as the town’s “Beer Baron.” However, Homer’s supply soon runs short, and he begins brewing his own liquor in the basement. While he manages to stay one step ahead of the law, the stills begin exploding and he eventually turns himself in.

The fate of the business is sealed for good when a city hall official finds out the original prohibition law was actually repealed only a year later.

The Lesson: Having a monopoly on an in-demand product is great, but dangerous when that product is illegal. Also, businesses that rely on a friendly regulatory environment are inherently risky. The government could essentially put you out of business at any time.

beer baron

(image source: ojaibeerbarons.com)

9. Make it Memorable

In Season 4’s Mr. Plow, Homer buys a truck with a snow plow attachment, reasoning he can afford the payment with money earned from plowing driveways.

The business gets off to a slow start, but explodes after a late-night television commercial featuring a catchy advertising jingle: “Call Mr. Plow, that’s my name. That name again is Mr. Plow.”

Jealous of Homer’s success, his friend Barney starts a rival snow plow company, called Plow King, and records a commercial of his own. The relationship turns bitter as Barney wins market share and Homer retaliates with some dirty and dangerous tactics. Ultimately the two reconcile their differences, and a heat wave puts them both out of business.

The Lesson: A memorable ad can mean the difference between making sales and making nothing.

10. Earn Repeat Business

When it comes to customer service, no one in Springfield knows the value of a long-term client more than Apu Nahasapeemapetilon, the proprietor of the local Kwik-E-Mart convenience store.

Every customer is given the same cheerful farewell after their purchase:

“Thank you, come again!”

Even if the big-box grocery stores offer a larger selection and better prices, they can’t beat Apu’s convenience and friendly service. For a small town “mom and pop”-style operation, customer loyalty is earned with every transaction.

The Lesson: It’s more costly to acquire a new customer than it is to sell more to an existing customer.

apu kwik-e-mart

(image source: massmediaverse.wordpress.com)

11. Be Yourself

In Season 7’s Bart Sells His Soul, Moe transforms his tavern into a family-friendly restaurant. Uncle Moe’s Family Feedbag enjoys some brief success, but the surly bartender isn’t cut out to be friendly and polite to this new demographic of customers.

He eventually snaps at a little girl and decides the family restaurant business isn’t for him. Rather than continue to pretend to be something he’s not , he returns the bar to it’s previous state — and with the transition is visibly more relaxed and content.

The Lesson: Not all business models will be a great fit for you, and that’s OK. Some people are natural-born salespeople, while others are better suited to different roles.

Uncle Moe’s Family Feedbag from Bryan Maul on Vimeo.

12. Your Network is Your Net Worth

In Season 3, Ned Flanders opens The Leftorium, a store selling items specially built for left-handed people. The store falters, with most patrons stopping by simply to have their parking validated without purchase.

As Flanders struggles to keep his business afloat, Homer comes across more and more lefties who would be perfect customers. Even though he initially wished his neighbor would fail, Homer eventually does the right thing and begins to refer people to The Leftorium.

The word of mouth spreads through the small town and Ned’s business survives on the back of his personal network.

The Lesson: Your network amplifies your reach and can connect you with the people who can help your business.


(image source: studentlife.ryerson.ca)

13. Outsource Smart

In King-Size Homer (Season 7), the power plant implements a daily calisthenics program to help workers get healthier. Homer despises the new exercise routine and learns that employees with a disability can qualify to work from home.

Then he discovers that workers who weigh over 300 pounds are considered disabled, and so embarks on a mission to purposely gain weight.

Once reaching his goal, Homer begins working from a makeshift home office. But laziness trumps work ethic, and he finds a keyboard shortcut — Typing “Y” has the same result as typing “Y-E-S.”

“I just tripled my productivity!” Homer exclaims.

Growing weary of punching the button himself, he finds a perpetual motion toy bird to be just as effective. Unfortunately the bird doesn’t have any reasoning skills or nuclear safety training and brings the power plant to the brink of meltdown.

Homer attempts to call the plant to warn them, but his fingers are too fat to dial. To save the day, he rushes there himself and prevents the disaster.

The Lesson: Before outsourcing any part of your work — mission-critical or not — make sure whoever you hire is up to the task. A poor hiring decision can be costly both in terms of time and money.

outsource smart

(image source: gifsoup.com)

14. Make Smart Pivots

In Season 6, The Simpsons pay a visit to Itchy and Scratchy Land, a theme park modeled around their favorite violent cartoon cat and mouse. The park is an homage to Disneyland, but the episode parodies Jurassic Park when the attractions start to attack.

However, the theme park is a natural brand extension for the popular TV characters. It’s a chance to engage on a deeper level with their biggest fans. Itchy and Scratchy land is a destination, a place designed to create lasting positive family memories.

The theme park gives the TV characters a chance to get off the screen and into real life — and into the hearts and wallets of the guests. Instead of just earning TV and licensing fees, now Itchy and Scratchy can earn parking fees, park admittance fees, souvenir sales, and food and beverage sales.

The Lesson: Extend your brand and your business where it makes sense.

15. Use Checks and Balances

In Oh Brother, Where Art Thou? (Season 2), Homer discovers he has a long-lost brother named Herbert Powell. Herb is the super-successful owner of Powell Motors, an automobile manufacturer in Detroit.

Herb is enthralled to find out about his new family, and forms an immediate bond with Bart and Lisa. As a gesture of goodwill, he invites the family to visit him in Detroit, and calls on Homer to help design a new car.

Initially Homer is timid with his design choices, but after a pep talk from Herb, really lets his creative spirit fly.

The end result is a car that is truly unique; it has a glass-domed roof, tail fins, and a horn that plays “La Cucaracha.” The car is unveiled to a shocked crowd and Herb soon realizes he gave Homer too much design freedom and offered too little oversight and guidance.

To make matters worse, Homer’s car comes with a price tag of $82,000 which leaves Herb bankrupt and Powell Motors out of business.

The Lesson: Getting outside design input was a great idea, but giving complete unchecked control over to anyone — especially an outsider — is a recipe for disaster. No one knows your business like you do.

homer's custom car

(image source: custombats.co.uk)

16. Live Your Brand

Comic Book Guy (Real name for trivia buffs: Jeff Albertson) is a recurring character on the show and the owner of The Android’s Dungeon comic shop. He’s a prime example of someone who eats, sleeps, and breathes his business.

Comic Book Guy is obese and nerdy, but also wickedly smart; he’s got a 170 IQ and is member of Springfield’s Mensa branch. We learn in one episode he holds a master’s degree in folklore and mythology, and translated The Lord of the Rings into Klingon for his thesis.

He runs the store as more than a business; it’s his life. Some comic book issues have too much sentimental value for him and he can’t part with them, even at the risk of insolvency. Still, his loyal customers like Bart and Milhouse know The Android’s Dungeon is their best bet for comic books, trading cards, and condescending sarcastic remarks.

In The Simpsons Movie, moments before his likely death, he admires his comic book collection and sighs with contentment:

“Life well spent.”

The Lesson: Do what you love, and you’ll never work a day in your life.

android's dungeon

(image source: simpsons.wikia.com)

Did I miss any of your favorites? Let me know in the comments below. With more than 500 episodes, I’m sure I missed some good ones!

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

8 thoughts on “16 Timeless Business Lessons from The Simpsons”

  1. I don’t really like the Simpsons, but I prefer Family Guy over anything.

    Really interesting article comparing some of their traits to business characteristics.

    I do agree in being yourself and take your own story to create greatness.

    Thanks for the post and keep up the good work over here!

    – Sam

  2. Fun post Nick, The Simpsons was such a funny show back in the day, brings back good memories :)
    One of my favorites is Homer’s patent pending “Miracle Spine-O-Cylinder”, a dented old trash can he used to straighten peoples spine out of his garage. A true Side Hustle…until Springfield’s Chiropractor gang sneaks in and destroys his invention.

  3. Simpsons ..hehe..I like it very much and am watching it from many years.So luck to come across your excellent blog. Your blog brings me a great deal of fun.. Good luck with the site.

  4. Thanks for sharing this. I grew up watching the Simpsons and forgot about many of these moments. I appreciate the reminder of these great events.

    I’ve gotta share this with my friends lol

  5. A lesson anyone should learn and use entrepreneurship to their advantage is never rely on a traditional cushy day job. Narcissist employers only want to rob employees and keep their monies due to them. They’ll not only keep their money, but set them up for termination, talk bad about the person to other members in management, cast the person they’re out to get in a certain light before other employees and create enmity between the targeted person and the employees for the sake of covering up the narcissists’ skeletons in their closet. Those are valuable business lessons anyone can use to their entrepreneurial advantage in staying energetic about their side hustle and their ability to prosper as an aspiring entrepreneur striving to achieve greatness.


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