Entrepreneurship Trivia
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99 free Entrepreneurship trivia questions with answers — trivia quiz, new questions added Oct 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 99 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 99 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 found just 39 such companies, about 0.07 percent of the software startups funded in the same decade.
Q 02Which children's toy began in 1930s Cincinnati as a compound for cleaning coal soot off wallpaper?
Play-Doh
Play-Doh was saved by a nursery-school teacher: Kay Zufall saw her pupils loved modelling with the fading cleaner and urged her brother-in-law's firm to sell it as a toy.
Q 03Which startup's founders raised about $30,000 in 2008 by selling breakfast cereal named after Obama and McCain?
Airbnb
Airbnb was then AirBed & Breakfast and deep in debt: its founders repackaged a thousand boxes as Obama O's and Cap'n McCains, and the sales paid off most of what they owed.
Q 04Which website launched in 2005 as a video dating service under the slogan 'Tune In, Hook Up'?
YouTube
YouTube's founders advertised on Craigslist, offering women money to upload dating videos; when almost nobody did, they opened the site to clips of any kind.
Q 05Which ice cream company's founders, priced out of opening a bagel shop, learned the trade from a Penn State correspondence course?
Ben & Jerry's
Ben & Jerry's opened in 1978 in a renovated gas station in Burlington, Vermont; Ben Cohen can barely smell, so he kept adding bigger chunks for texture, and they became the brand's trademark.
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 07Which e-commerce platform grew out of Snowdevil, an online snowboard store its founders launched in 2004?
Shopify
Shopify exists because Tobias Lütke, a programmer, disliked the store software on sale: he wrote his own for Snowdevil, and in 2006 the founders launched that software as the product.
Q 08Which Italian sports-car maker was founded in 1963 by a man who had grown rich building tractors?
Lamborghini
Lamborghini's founder Ferruccio built his first tractors from surplus military vehicles after the war; the profits bought him Ferraris, which he judged too noisy and rough for the road.
Q 09Juicero, maker of a juicer launched at $699, collapsed in 2017 after Bloomberg News showed its produce packs could be what?
Squeezed by hand
Squeezed by hand, the packs gave up their juice about as well as the machine did; widely mocked, Juicero offered refunds and shut down less than five months after the report.
Q 10What term describes launching a company on internal cash flow alone, with no outside capital?
Bootstrapping
Bootstrapping borrows from 'pull yourself up by your bootstraps', a phrase that originally described an impossible feat and only later came to mean getting ahead with no outside help.
Q 11Which startup term names the pace, usually stated per month, at which a company consumes its cash?
Burn rate
Burn rate tells a startup its 'runway': divide the cash in the bank by the monthly burn and you get the months left before it must turn a profit, raise more money or close.
Q 12Whose 2011 book The Lean Startup spread 'pivot' and 'minimum viable product' among founders?
Eric Ries
Eric Ries first set out the method on his blog in 2008; his book cites Zappos founder Nick Swinmurn, who posted photos of local shoe-store stock and bought each pair only after it sold.
Q 13Which chat app began as an internal tool at Tiny Speck, the studio behind the failed online game Glitch?
Slack
Q 21Which fashion designer's first Paris boutique, opened at 21 rue Cambon in 1910, sold only hats?
Coco Chanel
Coco Chanel called the shop Chanel Modes, and well-known actresses of the day wore her hats, which built the reputation she later carried into clothes.
Q 22Which British entrepreneur launched a magazine called Student at 16, then a mail-order record business?
Richard Branson
Richard Branson's headmaster told him on his last day at school that he would end up either in prison or a millionaire; the mail-order records became Virgin.
Q 23Roughly how many prototypes did James Dyson build over five years before his first bagless vacuum, the G-Force?
5,127
Slack was Stewart Butterfield's second accidental hit: his earlier attempt at an online game had also failed, leaving behind the photo-sharing site Flickr.
Q 14Which crowdfunding site, launched in 2009, hosted the Pebble smartwatch's record-breaking campaign in 2012?
Kickstarter
Kickstarter backers stepped in where investors had not: unable to raise more money the usual way, Pebble's founder asked the public for $100,000 and got it within two hours.
Q 15Which crowdfunded startup did Facebook buy for $2 billion in 2014, before it had shipped a consumer product?
Oculus
Oculus began with a teenager in a garage: Palmer Luckey finished his first headset prototype at 17, and the company had released only developer kits when Facebook bought it.
Q 16Which messaging app did Facebook agree to buy for $19 billion in February 2014?
WhatsApp's founders, Jan Koum and Brian Acton, had both applied for jobs at Facebook a few years earlier and been turned down.
Q 17Whitney Wolfe Herd, at 31, became the youngest woman to take a US company public in 2021 with which app?
Bumble
Bumble grew out of a break with Tinder: Wolfe Herd resigned in 2014, settled a sexual-harassment suit against the company, and launched a rival app on which women sent the first message.
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 World Records list as the first self-made female millionaire?
Madam C. J. Walker
Madam C. J. Walker denied being a millionaire in her lifetime: the record rests on her estate at her death in 1919, and earlier fortunes such as Mary Ellen Pleasant's are simply less documented.
5,127 was Dyson's own count of five years' work in a shed; vacuum makers who profited from selling dust bags turned the cleaner down, so it first went on sale in Japan.
Q 24Jack Ma, later Alibaba's founder, told Charlie Rose which fast-food chain rejected him for a job?
KFC
KFC hired 23 of the 24 people who applied when it came to his city, Ma said, leaving him the only one turned away; he also says Harvard Business School rejected him ten times.
Q 25Barbie's inventor Ruth Handler co-founded which toy company with her husband Elliot?
Mattel
Mattel blends the names of Harold 'Matt' Matson and Elliot Handler; Ruth was left out of the name, yet she went on to run the company as its president.
Q 26Whose first car venture, the Detroit Automobile Company, folded in 1901 after just twenty vehicles?
Henry Ford
Henry Ford lost his twelve backers $86,000, then walked out of his second firm, the Henry Ford Company, which carried on without him under a new name: Cadillac.
Q 27Laugh-O-Gram, a Kansas City cartoon studio that went bankrupt in 1923, was founded by whom?
Walt Disney
Walt Disney left Kansas City for Hollywood after the bankruptcy with $40 and a reel of Alice's Wonderland; that film won him the distribution deal that launched the Disney studio.
Q 28Martha Matilda Harper, a former servant, grew her 1888 Rochester hair salon into 500 shops by pioneering which business model?
Franchising
Franchising, in Harper's version, began with women like her: the first hundred salons went only to poor women, whom she trained and whose shops she inspected herself.
Q 29Which coffee chain was bought by a former employee who had quit to run his own espresso bar, Il Giornale?
Starbucks
Starbucks then mainly sold beans, and its founders did not want a chain of cafés, so Howard Schultz left to prove the idea, bought them out and put their name on his own bars.
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'.