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100 free PayPal trivia questions with answers — technology quiz, new questions added Aug 2026.
This PayPal trivia quiz covers the online payments company from a Palm Pilot security start-up called Fieldlink to a Fortune 500 giant with 426 million accounts. It opens with the founders Max Levchin, Peter Thiel and Luke Nosek, the March 2000 merger with Elon Musk's X.com, the boardroom coup that replaced Musk with Thiel, the 2002 IPO at $13 a share and the sale to eBay for $1.5 billion in stock a few months later. It also asks about the $10 sign-up bonus, why eBay sellers loved it, and the fraud-fighting software that led Thiel to found Palantir. The second half covers the group of alumni known as the PayPal Mafia, who went on to start YouTube, LinkedIn, Yelp and SpaceX, the Anonymous attacks after PayPal cut off WikiLeaks, the acquisitions of Braintree, Xoom, iZettle and Honey, PayPal.Me and PayPal Here, the Carl Icahn-driven spin-off from eBay in 2015, the launch of cryptocurrency trading and the PYUSD stablecoin, the misinformation-fine policy that was pulled after an outcry, the countries where PayPal cannot operate, and the takeover interest of 2026. Questions range from easy to expert. Every answer was checked against the Wikipedia articles on PayPal and the PayPal Mafia.
30 of 100 questions with answers and explanations. Play the quiz
Q 01Under what name was the company that became PayPal originally established in December 1998?
Fieldlink
It was soon renamed Confinity and made security software for hand-held devices before pivoting to a digital wallet.
Q 02Which three men founded the company that became PayPal?
Max Levchin, Peter Thiel and Luke Nosek
The first version of the PayPal payments system launched in 1999.
Q 03With which company, founded by Elon Musk in March 1999, did Confinity merge in March 2000?
X.com
Musk had co-founded it with Harris Fricker, Christopher Payne and Ed Ho as an online financial services firm.
Q 04Who replaced Elon Musk as CEO of X.com in October 2000?
Peter Thiel
That same month Musk had decided the company would drop its other banking operations and focus on payments; the firm was renamed PayPal in June 2001.
Q 05At what price per share did PayPal list on NASDAQ in its 2002 IPO?
$13
The offering raised over $61 million under the ticker PYPL, the same symbol it returned to in 2015.
Q 06How much did eBay pay to acquire PayPal on October 3, 2002?
$1.5 billion in stock
More than 70% of eBay auctions already accepted PayPal, which beat eBay's own Billpoint, Citibank's c2it and Yahoo's PayDirect.
Q 07How much did PayPal deposit in new users' accounts as a sign-up incentive in its early growth campaign?
$10
Auction sellers loved it because many could not qualify for a credit-card merchant account, and buyers liked not sharing card numbers with strangers.
Q 08PayPal's early fraud-monitoring software led its then-CEO to found which big-data company?
Palantir
By 2001 international hackers were draining small sums from many accounts and PayPal was losing millions a month.
Q 09What is the group of ex-employees who founded LinkedIn, YouTube and Yelp popularly called?
The PayPal Mafia
A 2007 Fortune photo shoot dressed them in mafia-style attire; Reid Hoffman says he prefers 'PayPal Network'.
Q 10How many of PayPal's first 50 employees were left within four years of the eBay takeover?
12
They struggled with eBay's more traditional corporate culture but stayed connected and funded one another's start-ups.
Q 11Which three former PayPal employees co-founded YouTube?
Steve Chen, Chad Hurley and Jawed Karim
Hurley and Chen skipped the famous Fortune mafia photo after their Google handler objected to the gangster motif.
Q 12Which former PayPal executive vice president founded LinkedIn?
Reid Hoffman
He was also an early investor in Facebook and sits on Microsoft's board.
Q 13Which PayPal co-founder, the 'consigliere' of the PayPal Mafia, later became CEO of Affirm?
Max Levchin
Thiel is the 'don'; former COO David Sacks founded Yammer and became the White House AI and crypto czar in December 2024.
Q 21Which Amsterdam-based company did eBay turn to for payments after its PayPal agreement ended in 2020?
Adyen
PayPal remained a payment option on eBay but was no longer featured ahead of cards.
Q 22Which digital money-transfer company did PayPal buy for about $1.09bn in 2015?
Xoom
It brought 1.3 million US customers sending money to 37 countries; Pakistan's government later used Xoom to crowdfund two dams.
Q 23What is the format of a payment-request link on the service launched in September 2015?
PayPal.me/username/amount
The service launched in 18 countries when PayPal had 170 million users, aiming for a mobile-first experience.
Q 14Which venture firm did former PayPal CFO Roelof Botha join as a partner?
Sequoia
Fellow ex-CFO Ken Howery joined Founders Fund and served as US ambassador to Sweden and later Denmark.
Q 15Which Israeli start-up specialising in online risk tools did PayPal buy for $169M in January 2008?
Fraud Sciences
That November it also bought Bill Me Later, the online credit company later rebranded PayPal Credit.
Q 16Why did hacktivists linked to Anonymous launch denial-of-service attacks on the company in December 2010?
It had stopped processing donations to WikiLeaks
Fourteen alleged members, the 'PayPal 14', were charged in July 2011 and most pleaded guilty in 2013.
Q 17How many active user accounts did PayPal have by 2010, according to Wikipedia?
Over 100 million
They spanned 190 markets and 25 currencies; by 2022 the figure was 426 million accounts in 202 markets.
Q 18Which Chicago-based payment gateway did PayPal acquire in 2013 to boost its mobile business?
Braintree
Braintree owned Venmo; a year later PayPal launched One Touch, letting users pay with a single tap on partner sites.
Q 19Which activist investor demanded in 2013 that eBay spin off PayPal?
Carl Icahn
The split was announced on September 30, 2014, and completed on July 18, 2015, with PayPal relisting under PYPL.
Q 20On what date was PayPal's spin-off from eBay completed?
July 18, 2015
eBay later said that after their agreement ended in 2020 it would work with Amsterdam-based Adyen instead.
Q 24Which Swedish payment processor did PayPal agree to buy for $2.2bn in May 2018?
iZettle
It was PayPal's largest acquisition until the $4 billion Honey deal announced in late 2019.
Q 25Which company did PayPal acquire for over $4bn on January 6, 2020, then its largest deal?
Honey
The browser coupon extension deal came months after PayPal booked a $228 million loss, largely on a $500 million Uber investment.
Q 26Which NBA team did PayPal become a jersey patch sponsor of in 2018?
Phoenix Suns
PayPal opened a technology centre in Scottsdale, Arizona, in 2006 and has support operations in Chandler.
Q 27Which company issued PayPal's stablecoin PYUSD when it launched in August 2023?
Paxos
PayPal secured the first conditional crypto licence from New York's financial regulator in October 2020.
Q 28What is the ticker-style name of the US dollar stablecoin PayPal launched in August 2023?
PYUSD
The SEC subpoenaed both PayPal and Paxos over it that November.
Q 29What fine did PayPal's withdrawn October 2022 policy propose for users spreading misinformation?
$2,500
Former president David Marcus said it 'goes against everything I believe in', Elon Musk piled on, and PayPal withdrew it.
Q 30Which former Intuit executive became PayPal's CEO in September 2023, succeeding Dan Schulman?
Alex Chriss
Schulman had joined from American Express and Virgin Mobile in 2014; Chriss was replaced by Enrique Lores in February 2026.