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50 free Entrepreneurship trivia questions with answers — trivia quiz, new questions added Aug 2026.
Most famous companies did not start as the thing they became. A chat app was the by-product of a failed game, a streaming giant was pitched as a matchmaking site, and a fashion empire began in a rented Paris shop that was only allowed to sell one kind of product. The stories behind the founders are often stranger than the balance sheets. These 50 questions cover the founders and their false starts, the pivots that saved companies, the vocabulary of startups and venture funding, the accelerators and incubators that shape new firms, and the older history of enterprise, from the economist who first described the entrepreneur to the world's oldest surviving businesses. Every answer comes with a short explanation and a source. It suits business students, pub quiz setters, anyone running a workshop on enterprise, and players who simply like knowing where the brands in their pocket came from. Most questions are answerable by a curious general reader; a few are there for people who read term sheets for fun.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Investor Aileen Lee picked which mythical beast in 2013 for a private startup valued at $1B or more?
Unicorn
Unicorn was chosen for its rarity: Lee's TechCrunch article counted just 39 such companies, and by May 2024 CB Insights listed more than 1,200.
Q 02Play-Doh began in 1930s Cincinnati as which household product, long before schools used it as clay?
Wallpaper cleaner
Wallpaper cleaner was the original product: the compound was reworked and marketed to Cincinnati schools in the mid-1950s, becoming a toy only after its cleaning days were over.
Q 03Airbnb's founders raised $30,000 in 2008 by selling what, branded after candidates Obama and McCain?
Breakfast cereal
Breakfast cereal named after the two candidates was sold mostly at the 2008 Democratic National Convention, keeping the site then called AirBed & Breakfast afloat.
Q 04YouTube co-founders Chad Hurley and Steve Chen, both ex-PayPal, said their 2005 site was first conceived as what?
A dating service
A dating service with video profiles was the pitch, influenced by Hot or Not; the idea broadened after Jawed Karim could not find clips of the 2004 Indian Ocean tsunami online.
Q 05Priced out of bagels, Ben Cohen and Jerry Greenfield took a correspondence course in what?
Ice cream making
Ice cream making was the fallback after bagels: the Penn State course led to a $12,000 parlour in a renovated Burlington, Vermont, gas station in May 1978.
Q 06Ray Kroc was selling what when he visited the McDonald brothers' San Bernardino restaurant in 1954?
Milkshake mixers
Milkshake mixers from Prince Castle were Kroc's line, and the brothers had bought eight of his Multimixers, which is what made him curious enough to visit.
Q 07Shopify's founders built their own platform in 2006 after first opening an online store for what?
Snowboards
Snowboards were the stock at Snowdevil, the 2004 shop of Tobias Lütke, Daniel Weinand and Scott Lake; unhappy with existing e-commerce software, Lütke coded his own and that became the product.
Q 08Ferruccio Lamborghini started building sports cars in 1963 to rival Ferrari after succeeding with what?
Tractors
Tractors made his money: Lamborghini Trattori, founded in 1948, still builds them in Pieve di Cento, Italy.
Q 09Juicero's $699 juicer collapsed in 2017 after Bloomberg News showed its produce packs could be what?
Squeezed by hand
Squeezed by hand, the packs gave juice nearly indistinguishable from the machine's, and venture capitalist Ben Einstein called the press 'an incredibly complicated piece of engineering'.
Q 10What term describes launching a company on internal cash flow alone, with no outside capital?
Bootstrapping
Bootstrapping means surviving the startup phase on internal cash flow and tight expenses, with a small pot of money set aside at the outset for the process.
Q 11Which startup term names the pace, usually stated per month, at which a company consumes its cash?
Burn rate
Burn rate is negative cash flow with a vivid name, typically expressed in monthly terms, and the same phrase describes how fast people spend their own discretionary income.
Q 12Whose 2011 book The Lean Startup spread 'pivot' and 'minimum viable product' among founders?
Eric Ries
Eric Ries built the book on his blog, citing Zappos founder Nick Swinmurn, who tested demand by photographing local shoe-store stock before building a website or inventory.
Q 13Slack, the workplace chat app, grew out of an internal tool at Tiny Speck, a studio developing what?
A massively multiplayer game
Q 21Coco Chanel's first licensed Paris business, opened at 21 rue Cambon in 1910, sold only what?
Hats
Hats were all she could sell there: the rue Cambon building already housed a clothing business, so the milliner's shop named Chanel Modes stuck to millinery.
Q 22Richard Branson's first business venture, started at the age of 16, was a magazine called what?
Student
Student was the title, and the teenage publisher went on to be knighted in March 2000 for 'services to entrepreneurship'.
Q 23Roughly how many prototypes did James Dyson build over five years before his 1983 G-Force vacuum?
5,127
5,127 was Dyson's own count, made while his wife's salary as an art teacher helped support the family; no UK manufacturer would handle the result.
A massively multiplayer game called Glitch was Tiny Speck's first product, a social MMORPG led by Flickr co-founder Stewart Butterfield; it 'unlaunched' in 2012 and the team's chat tool became the business.
Q 14Which crowdfunding site, launched in 2009, hosted Oculus's 2012 campaign for its VR headset?
Kickstarter
Kickstarter was started by Perry Chen, Yancey Strickler and Charles Adler, and every project page ever launched there stays permanently archived and public.
Q 15How much did Facebook pay in 2014 for Oculus, a VR startup that had crowdfunded its headset in 2012?
$2 billion
$2 billion bought a company that had shipped only a development prototype; the first consumer Rift did not arrive until March 2016.
Q 16What price did Facebook announce for WhatsApp in February 2014, its largest acquisition to date?
$19 billion
$19 billion broke down as $4 billion in cash, $12 billion in Facebook shares and $3 billion in restricted stock units for WhatsApp's founders.
Q 17Whitney Wolfe Herd, aged 31, became the youngest woman to take a company public in 2021 with which app?
Bumble
Bumble's IPO also made Wolfe Herd the world's youngest female billionaire, and she rang the Nasdaq bell with her 14-month-old son on her hip.
Q 18Sara Blakely spent two years and how much in savings developing the hosiery idea that became Spanx?
$5,000
$5,000 was the entire budget, spent while she still worked at Danka in Atlanta; by 2012 Forbes put her on its cover as the youngest self-made female billionaire in the world.
Q 19Yvon Chouinard handed which outdoor-clothing company to a trust and a climate non-profit in 2022?
Patagonia
Patagonia's voting stock went to the Patagonia Purpose Trust and its non-voting stock to the Holdfast Collective, so profits fund climate work and land protection.
Q 20Which hair-care entrepreneur does Guinness list as America's first self-made female millionaire?
Madam C. J. Walker
Madam C. J. Walker may not even have been first — Mary Ellen Pleasant's wealth is less documented — and at her death she was the wealthiest self-made Black woman in America.
Q 24Jack Ma, later Alibaba's founder, told Charlie Rose which fast-food chain rejected him for a job?
KFC
KFC said 'you're no good', Ma recalled, and he also claims Harvard Business School rejected him ten times in a row.
Q 25Barbie's inventor Ruth Handler co-founded which toy company with her husband Elliot?
Mattel
Mattel had Handler as its first president from 1945 to 1975, and Barbie arrived in 1959 with curves that gave dolls an adult shape.
Q 26Whose first car venture, the Detroit Automobile Company, folded in 1901 after just twenty vehicles?
Henry Ford
Henry Ford attracted twelve backers in 1899, lost them $86,000 and went on to found the Henry Ford Company before the firm that still bears his name.
Q 27Laugh-O-Gram, a Kansas City cartoon studio that went bankrupt in 1923, was founded by whom?
Walt Disney
Walt Disney sold his camera after the bankruptcy and moved to Hollywood with an unfinished reel of Alice's Wonderland.
Q 28Who launched modern retail franchising with an international chain of 500 hair salons?
Martha Matilda Harper
Martha Matilda Harper franchised the salon model to low-income women, and at its peak her company had more than 500 franchises plus a line of hair-care products.
Q 29Which coffee shop did Howard Schultz open after quitting Starbucks in 1985, later merging the two?
Il Giornale
Il Giornale came after Schultz visited more than 500 espresso bars in Milan and raised the $400,000 he needed to start it.
Q 30Which Irish-French banker's Essai first framed the entrepreneur as a bearer of risk?
Richard Cantillon
Richard Cantillon's Essai Sur La Nature Du Commerce En Général was largely forgotten until William Stanley Jevons rediscovered it in the late 19th century and called it the 'cradle of political economy'.