Peter Thiel and Elon Musk formed PayPal after merging two dot-com companies

PayPal was started in 1998 by Peter Thiel

By the year 2002, PayPal went public for the first time—but that was far from the end of its business story. eBay later bought PayPal, then eventually spun it off. PayPal IPO'd for a second time in 2015.

The concept for Palantir's key software came from PayPal's anti-fraud protocol

PayPal, which, like Palantir, was cofounded by Peter Thiel, developed the initial framework for Palantir's data-mining service to prevent financial crime. Following the 9/11 terrorist attacks, Thiel realized the software could also enable government agencies to connect data and prevent similar terrorist attacks from occurring in the future.

Elon Musk's first company was an online business directory called 'Zip2'

Musk started the online alternative to Yellow Pages in 1995 with his younger brother. Musk sold the company for $305M in 1999.

PayPal's Peter Thiel turned his Roth IRA into $5B

In 1999, tech titan Peter Thiel had a Roth IRA with roughly $2K in it. By 2019, that tax-free account was worth $5B. For context, the average Roth IRA was worth roughly $39K at the end of 2018. Naturally, Thiel had a few investment options that the average person probably doesn’t have access to—but the story of his IRA’s boom is nonetheless fascinating.

One Facebook investor turned $500K into $1B

Peter Thiel was Facebook's first big investor. In 2004, he invested $500K into the social network, long before the company owned Instagram or renamed itself "Meta." In 2012, when he sold off most of his stake, he turned that initial $500K investment into more than $1B in cash.

Y Combinator was founded in 2005 to bridge gaps between founders and investors

In one of Paul Graham’s essays on his website, he took the time to explain how and why he and his cofounders (including his girlfriend at the time, and now wife, Jessica Livingston), came up with the idea of and eventually created Y Combinator.

Listen to a conversation between two Palantir cofounders—Peter Thiel and Joe Lonsdale

Palantir cofounder Joe Lonsdale was an editor of the Stanford Review (which Peter Thiel founded), and Thiel became a mentor to Lonsdale. The two discussed shared sentiments about the importance of developing Palantir to maintain a largely American global order, as well as cultural revolutions.

Many original dot-com company founders were bought out early on

The people who bought the original domains for dot-com companies and had the ideas to start businesses were often bought out by investors before becoming well-known companies. Both Pets.com and Broadcast.com were acquired early on.

Read a timeline of all of Elon Musk's business ventures, from the software company Zip2 in the 1990s to Musk's Twitter acquisition.

Yahoo acquired Paul Graham's former startup Viaweb in 1998

Viaweb was the web app tech startup that Paul Graham, Robert Morris, and Trevor Blackwell cofounded before they started Y Combinator. The company sold for $49M and Viaweb was rebranded as the Yahoo Store.

Y Combinator, the startup accelerator, gets its name from the 'Y combinator' computer science concept.

YouTube began as a quirky site invented by former PayPal employees

In February 2005, YouTube was launched by Steve Chen, Chad Hurley, and Jawed Karim. Their idea was to build a platform to support the convenient sharing of videos online, a relatively novel idea in the days of cable TV and early social media.

Legendary venture capitalist Peter Thiel once wrote that 'competition is for losers'

With Peter Thiel's "Monopoly Theory," the Founders Fund partner argued that investing in companies that create new categories, rather than those that compete with other businesses in existing ones, is a best practice in venture capital.

Pets.com is one of the most emblematic dot-com companies

Pets.com—an e-commerce pet store webpage—is a prime example of dot-com companies burning through investments. Despite being a popular and well-known brand, the company struggled to generate enough revenue to become profitable. After raising approximately $82.5M in its February 2000 initial public offering, Pets.com filed for bankruptcy in November of that same year.

Bill Gates and Paul Allen were childhood friends before founding Microsoft

The two bonded over a teletype terminal at their school, which required a $40 hourly fee for computing time. They were banned from using the device after exploiting a bug that allowed them to bypass the fee, only to be later offered free computing time for finding more bugs.

Sears once tried to become a tech company

In 1984, Sears arguably created one of the first online retail services, called “Prodigy,” in 1984 alongside IBM and CBS. But it was more of a WeChat than an Amazon, offering a variety of other services to users a few years before the dot com era.

Read more about Palantir cofounder Peter Thiel's political beliefs and activity

At Stanford University, Thiel founded "The Stanford Review," a libertarian magazine dedicated to being against "political correctness." Since then, Thiel has railed against American universities as failing institutions, given lectures about the coming of the Antichrist, and donated money to high-profile political campaigns (including those of President Donald Trump and Vice President JD Vance).

Key moments in fintech history include the transatlantic cable’s invention and E-Trade’s founding

Founded in 1982, E-Trade was the first-ever online brokerage, pioneering a method of investing that is common today. Its story is part of a timeline that the New York Times put together of key moments in early fintech history.

Mark Zuckerberg was nearly fired from his own company after refusing to sell Facebook to Yahoo for $1B

In 2006, Yahoo tried to buy Facebook for $1B. Despite enthusiasm from nearly all of Facebook's management team and board (which included PayPal cofounder and famed investor Peter Thiel at the time), then 22-year-old Zuckerberg turned down the offer, insisting that Yahoo undervalued the company and didn't have a clear vision for the future. Zuckerberg has since said he regrets not being clear about his intentions to grow the company with his team before the Yahoo bid, as almost all of the company's management team left after he turned down the offer.

3 out of Palantir's 5 cofounders once served as editor-in-chief of The Stanford Review

After Peter Thiel founded the conservative student newspaper, he remained involved and invested in the paper's success. Other Palantir cofounders, Joe Lonsdale and Stephen Cohen, also both previously served as the paper's editor-in-chief.

Apple’s third cofounder was its angel investor

Steve Jobs and Steve Wozniak are well-known for cofounding Apple, but the company had a third founder who acted as an angel investor: Mike Markkula, who invested $250K in 1977.

Two of American Express' co-founders also founded Wells Fargo

Henry Wells and William Fargo formed Wells, Fargo & Co. two years after American Express was created. Wells and Fargo saw an opportunity to expand the express delivery service from the East Coast and Middle America to the West Coast. The two initially asked the American Express board to expand operations, but the board declined, so they decided to create their own company. Today, Wells Fargo is among the top four largest banks in the US.

The dot-com boom made Mark Cuban a billionaire

Cuban co-founded AudioNet with Todd Wagner in 1995 before it became Broadcast.com—a web app that allowed people to listen to sports commentary on their computers if they couldn't watch a game. In 1999, Yahoo bought Broadcast.com for $5.7B. By the time the market crashed, Cuban had already sold most of his stock in the company and had become a billionaire.

In 1994, Amazon was founded as an online bookseller

Books were just the start, as founder Jeff Bezos' ultimate goal was to create an "everything store," using the internet to transcend the physical limitations of brick-and-mortar retail. The Seattle-based Amazon gradually added CDs and consumer electronics, becoming a dominant e-commerce player in the late 1990s, and one of the few dot-com companies to make it through the bust.

Owned by Tencent, WeBank was China's first digital bank and services 340 million customers.

The payments tool Zelle was created by big banks to compete with apps like Venmo

Zelle is an alternative to Venmo, where people can pay each other back for expenses like apartment utilities or dinner. But its origin story has more to do with big finance than small transactions.

The dot-com bubble burst in the early 2000s

If you’ve heard of companies like Google and Yahoo, you’re already partially familiar with the dot-com bubble: a period from roughly 1995 to 2001, when internet companies were the hottest thing in venture capital. The “bubble” part of the term refers to the industry’s eventual implosion.

SpaceX was built to achieve Elon Musk's vision of making humans an interplanetary species.

Apple's first backer recruited his own CEO to help manage the company

Wanting Steve Jobs and Steve Wozniak to focus on developing Apple computers, Mike Markkula brought in his colleague from Fairchild Semiconductor, Michael Scott. As employee number five, Scott helped professionalize the fledgling computer company and getting manufacturing off the ground. (Some users may experience a paywall.)

YC was partly inspired by an investor named Julian Weber

Y Combinator Cofounder Paul Graham’s former professor’s husband Julian Weber provided $10K in seed funding to Graham’s previous startup, Viaweb in its early days. In exchange, Weber received 10% of the company. Weber’s involvement inspired Graham to start a program where investors were more involved with the companies they contributed seed funding to.

The evolution of X, from startup to Musk-owned giant, reflects rapid tech shifts

Twitter began in 2006 as a side project and grew into a major global platform, widely used for news, activism, and political discourse. Despite mainstream success, it faced ongoing management turmoil, business struggles, and rising concerns over misinformation and user safety.

Elon Musk joined Tesla in 2004, investing $30M and becoming chair

The company went public in 2010, raising $226 million in its IPO just two years after beginning production on its first car. Tesla's first Supercharger stations were launched in 2012 with six locations in California.

Read an overview of Tencent's biggest business moments, from the 2011 WeChat launch to streaming deal with Universal Music Group.

Mark Zuckerberg credits some of Facebook's success to constant evolution

Before becoming the head of OpenAI, Sam Altman was the president of Y Combinator—a startup accelerator company that supported companies like Airbnb, DoorDash, and Coinbase. In 2016, Altman interviewed Zuckerberg about creating Facebook and its growth over time. Zuckerberg said that, unlike other companies (think: CourseMatch), Facebook kept growing and adding new features, which prevented the app from becoming obsolete.

In high school, Mark Zuckerberg rejected Microsoft's proposal to buy his music suggestion software for $950K

Mark Zuckerberg and Adam D'Angleo built a website called "Synapse," which created playlists for users based on their listening preferences and an algorithm to suggest new songs, in September 2002.

7 angel investors funded Google in its early days

Entrepreneur Shaan Puri shares how seven strangers acted as Google’s earliest angel investors. The first gave Google $100K without even putting his equity agreement in writing. The investors on “Shark Tank” use their personal funds to support startups, but they’re often more predatory about terms than typical angels.

Elon Musk claims cutting costs fast was the only way to stop X from dying

Laying off 80% of X's workforce, says Musk, was required to avoid a financial collapse within months of him purchasing the platform. In 2023, he claimed X would be cash-flow positive within the year as advertisers returned to the platform.

Elon Musk once tried to make himself CEO of artificial intelligence behemoth and ChatGPT creator OpenAI.

For Reddit's founders, the company's early days included choosing a dinner with Y Combinator's Paul Graham over a spring break trip, a $10M Condé Nast acquisition, and other pivotal moments.

Facebook was almost sold to Yahoo! for $1B, but its CEO refused

The board tried to fire Mark Zuckerberg for his resistance, which he blames for failing to communicate the long-term vision of the company. He claims the company has succeeded by launching products quickly to learn faster than its competitors.

The 'big bang' of the dot-com era: Netscape's stock price doubled on the day of its initial public offering

The company behind the browser that revolutionized search went public on August 9, 1995. Just before the IPO, the company increased its initial opening price from $14 to $28. On the day the company went public, shares traded as high as $71 before closing at $58.25. The company's market capitalization exceeded $2B. The eye-popping IPO is largely considered the beginning of the dot-com bubble.

When he first enrolled at Princeton University, Jeff Bezos wanted to study physics

He later changed his major to electrical engineering and computer science. He graduated Summa Cum Laude and received job offers at Intel, Nokia, and Accenture, but he declined those offers in favor of a job at a fintech startup.

ChatGPT was conceived over dinner at a Silicon Valley hotel.

Silicon Valley’s reign over tech, money, and politics

Tesla and X CEO Elon Musk, OpenAI CEO Sam Altman, LinkedIn founder Reid Hoffman, and others are getting into politics. From Musk’s role in President Trump’s second term to Hoffman’s spending on former Vice President Harris’ presidential campaign, more tech CEOs are expanding into politics. This podcast episode by WBUR and American Public Media discusses what the impact could be with so many tech figures engaging in American politics. Listen here.

Watch a timeline of Tencent—one of China's earliest tech giants—despite the company's low profile.

eCash paved the way for today’s popular crypto investments

Bitcoin is typically cited as the first decentralized cryptocurrency. But some argue that back in the 1990s, eCash was technically the first cryptocurrency, although it wasn't decentralized.

More than 650 companies went public in the US in 1996

As the dot-com bubble reached its peak, most dot-com companies went public with little proof of being profitable and were often overvalued. In 1999, the Nasdaq's price-to-earnings ratio (a tool used to determine a stock's value that divides its price by earnings) hit 90.2, signaling that many companies were operating at a net loss. Startups promised investors that more time and money would help scale their businesses and become profitable.

Steve Jobs founded NeXT while on a break from Apple

While Steve Jobs was on a hiatus from working at Apple, he founded a company called NeXT and helped lead the release of its operating system NeXTSTEP. The operating system was used to create the first app store of sorts, as well as the first web browser.

The rebrand to X was to make Twitter an all-in-one social media app

Elon Musk renamed the platform as part of his plan to create an app that goes beyond posts and tweets. The rebrand included a new name, logo, and vision for a platform that offers messaging, video, banking, shopping, and more.

Y Combinator changed the way startups around the world are built

Many of the philosophies that the leaders of Y Combinator have infused into the program’s portfolio companies have become the playbook for building the next big thing, such as its focus on founder personality and more.