We can look around at distributed banking, crypto-currencies, Special Purpose Acquisition Companies, and so many other innovative business strategies as new and exciting and innovative. And they are. But paving the way for them was simplifying online payments to what I’ve heard Elon Musk call just some rows in a database.
Peter Thiel, Max Levchin, and former Netscaper Luke Nosek had this idea in 1998. Levchin and Nosek has worked together on a startup called SponsorNet New Media while at the University of Illinois Champagne-Urbana where PLATO and Mosaic had come out of. And SponsorNet was supposed to sell online banner ads but would instead be one of four failed startups before zeroing in on this new thing, where they would enable digital payments for businesses and make it simple for consumers to buy things online. They called the company Confinity and setup shop in beautiful Mountain View, California.
It was an era when a number of organizations were doing things in taking payments online that weren’t so great. Companies would cache credit card numbers on sites, many had weak security, and the rush to sell everything in the bubble forming around dot-coms fueled a knack for speed over security, privacy, or even reliability.
Confinity would store the private information in its own banking vaults, keep it secure, and provide access to vendors - taking a small charge per-transaction. Where large companies had been able to build systems to take online payments, now small businesses and emerging online stores could compete with the big boys. Thiel and Levchin had hit on something when they launched a service called PayPal, to provide a digital wallet and enable online transactions. They even accepted venture funding, taking $3 million from banks like Deutsche Bank over Palm Pilots. One of those funders was Nokia, investing in PayPal expanding into digital services for the growing mobile commerce market. And by 2000 they were up to 1,000,000 users.
They saw an opening to make a purchase from a browser on a phone or a browser or app on a cell phone using one of those new smart phone ideas. And they were all rewarded with over 10 million people using the site in just three short years, processing a whopping $3 billion in transactions.
Now this was the heart of the dot-com bubble. In that time, Elon Musk managed to sell his early startup Zip2, which made city guides on the early internet, to Compaq for around $300 million, pocketing $22 million for himself. He parlayed that payday into X.com, another online payment company. X.com exploded to over 200,000 customers quickly and as happens frequently with rapid acceleration, a young Musk found himself with a new boss - Bill Harris, the former CEO of Intuit.
And they helped invent many of the ways we do business online at that time. One of my favorite of Levchin’s contributions to computing, the Gausebeck-Levchin test, is one of the earliest implementations of what we now call CAPTCHA - you know when you’re shown a series of letters and asked to type them in to eliminate bots.
Harris helped the investors de-risk by merging with Confinity to form X.com. Peter Thiel and Elon Musk are larger than life minds in Silicon Valley. The two were substantially different. Musk took on the CEO role but Musk and Thiel were at heads. Thiel believed in a Linux ecosystem and Musk believed in a Windows ecosystem. Thiel wanted to focus on money transfers, similar to the PayPal of today. Given that those were just rows in a database, it was natural that that kind of business would become a red ocean and indeed today there are dozens of organizations focused on it. But Paypal remains the largest. So Musk also wanted to become a full online banking system - much more ambitious. Ultimately Thiel won and assumed the title of CEO.
They remained a money transmitter and not a full bank. This means they keep funds that have been sent and not picked up, in an interest bearing account at a bank.
They renamed the company to PayPal in 2001 and focused on taking the company public, with an IPO as PYPL in 2002. The stock shot up 50% in the first day of trading, closing at $20 per share. Yet another example of the survivors of the dot com bubble increasing the magnitude of valuations. By then, most eBay transactions accepted PayPal and seeing an opportunity, eBay acquired PayPal for $1.5 billion later in 2002. Suddenly PayPal was the default option for closed auctions and would continue their meteoric rise. Musk is widely reported to have made almost $200 million when eBay bought PayPal and Thiel is reported to have made over $50 million.
Under eBay, PayPal would grow and as with most companies that IPO, see a red ocean form in their space. But they brought in people like Ken Howery, who serve as the VP of corporate development, would later cofound investment firm Founders Fund with Thiel, and then become the US Ambassador to Sweden under Trump. And he’s the first of what’s called the PayPal Mafia, a couple dozen extremely influential personalities in tech.
By 2003, PayPal had become the largest payment processor for gambling websites. Yet they walked away from that business to avoid some of the complicated regulations until various countries that could verify a license for online gambling venues.
In 2006 they added security keys and moved to sending codes to phones for a second factor of security validation. In 2008 they bought Fraud Sciences to gain access to better online risk management tools and Bill Me Later.
As the company grew, they setup a company in the UK and began doing business internationally. They moved their EU presence to Luxembourg 2007. They’ve often found themselves embroiled in politics, blocking the any political financing accounts, Alex Jones show InfoWars, and one of the more challenging for them, WikiLeaks in 2010. This led to them being attacked by members of Anonymous for a series of denial of service attacks that brought the PayPal site down.
OK, so that early CAPTCHA was just one way PayPal was keeping us secure. It turns out that moving money is complicated, even the $3 you paid for that special Golden Girls t-shirt you bought for a steal on eBay. For example, US States require reporting certain transactions, some countries require actual government approval to move money internationally, some require a data center in the country, like Turkey. So on a case-by-case basis PayPal has had to decide if it’s worth it to increase the complexity of the code and spend precious development cycles to support a given country. In some cases, they can step in and, for example, connect the Baidu wallet to PayPal merchants in support of connecting China to PayPal.
They were spun back out of eBay in 2014 and acquired Xoom for $1 billion in 2015, iZettle for $2.2 billion, who also does point of sales systems. And surprisingly they bought online coupon aggregator Honey for $4B in 2019. But their best acquisition to many would be tiny app payment processor Venmo for $26 million. I say this because a friend claimed they prefer that to PayPal because they like the “little guy.”
Out of nowhere, just a little more than 20 years ago, the founders of PayPal and they and a number of their initial employees willed a now Fortune 500 company into existence. While they were growing, they had to learn about and understand so many capital markets and regulations. This sometimes showed them how they could better invest money. And many of those early employees went on to have substantial impacts in technology. That brain drain helped fuel the Web 2.0 companies that rose.
One of the most substantial ways was with the investment activities. Thiel would go on to put $10 million of his money into Clarium Capital Management, a hedge fund, and Palantir, a big data AI company with a focus on the intelligence industry, who now has a $45 billion market cap. And he funded another organization who doesn’t at all use our big private data for anything, called Facebook. He put half a million into Facebook as an angel investor - an investment that has paid back billions. He’s also launched the Founders Fund, Valar Venture, and is a partner at Y Combinator, in capacities where he’s funded everyone from LinkedIn and Airbnb to Stripe to Yelp to Spotify, to SpaceX to Asana and the list goes on and on and on.
Musk has helped take so many industries online. Why not just apply that startup modality to space - so launched SpaceX and to cars, so helped launch (and backed financially) Tesla and solar power, so launched Solar City and building tunnels so launched The Boring Company. He dabbles in Hyperloops (thus the need for tunnels) and OpenAI and well, whatever he wants. He’s even done cameos in movies like Iron Man. He’s certainly a personality.
Max Levchin would remain the CTO and then co-found and become the CEO of Affirm, a public fintech company.
David Sacks was the COO at PayPal and founded Yammer. Roelof Botha is the former CFO at PayPal who became a partner at Sequoia Capital, one of the top venture capital firms. Yishan Wong was an engineering manager at PayPal who became the CEO of Reddit.
Steve Chen left to join Facebook but hooked back up with Jawed Karim for a new project, who he studied computer science at the University of Illinois at Champaign-Urbana with. They were joined by Chad Hurley, who had created the original PayPal logo, to found YouTube. They sold it to Google for $1.65 billion in 2006. Hurley now owns part of the Golden State Warriors, the MLS Los Angeles team, and Leeds United.
Reid Hoffman was another COO at PayPal, who Thiel termed the “firefighter-in-chief” and left to found LinkedIn. After selling LinkedIn to Microsoft for over $26 billion he become a partner at venture capital firm, Greylock Partners.
Jeremy Stoppelman and Russel Simmons co-founded Yelp with $1 million in funding from Max Levchin, taking the company public in 2011. And the list goes on.
PayPal paved the way for small transactions on the Internet. A playbook repeated in different parts of the sector by the likes of Square, Stripe, Dwolla, Due, and many others - including Apple Pay, Amazon Payments, and Google Wallet. We live in an era now, where practically every industry has been taken online. Heck, even cars. In the next episode we’ll look at just that, exploring the next steps in Elon Musk’s career after leaving PayPal.