Executives at American Online wanted to shut down AIM

See a ranking of the most popular websites on the World Wide Web from 1995 to 2023

America Online's homepage was the most popular website through mid-2021, when the Yahoo homepage took over and, shortly afterward, became the first website to reach 1 billion monthly visits. It would not be dethroned until early 2006 by Google, a major player in the search engine market.

At 12 years old, Mark Zuckerberg built a messaging platform for his family called 'ZuckNet.'

The philosophy of effective altruism was at the heart of Sam Altman's firing

OpenAI was originally created as a nonprofit to develop artificial general intelligence for humanity's benefit. However, skyrocketing computing costs made adherence to this belief difficult, as new influences, such as external investors, were introduced to accelerate growth with reduced safety.

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 Million Dollar Homepage' is a snapshot of a dead internet

In 2005, 21-year-old Alex Tew set out to make $1M by selling $1 pixels on his website, effectively creating a standalone internet billboard. The gambit worked, and because the advertisements were one-time payments, the site looks the same as it did in 2005, despite many of the advertised sites going defunct since.

A Grateful Dead online bulletin board system inspired the early internet and counted some of tech's biggest names, like Apple's Steve Wozniak, as users.

The band Radiohead launched a chatbot to promote its 2001 album, creating a popular form of artificial intelligence over 20 years before ChatGPT.

American International Group, one of the largest insurance companies in the world, received $182B from the federal government—the largest of any bailout in the wake of the Great Recession.

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.

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.

American Express intentionally targets wealthy cardholders, who spend higher amounts per transaction and tend to make more transactions than the average cardholder, thereby reducing the company's risk.

OpenAI helped kick-start an AI arms race in Silicon Valley

Led by CEO Sam Altman, OpenAI's mission is to "ensure artificial general intelligence benefits all of humanity" by making its products open to all users. In 2023, the $86B company behind the chatbot ChatGPT consisted of a for-profit arm under its nonprofit governing board.

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

The overnight collapse of Ello, a beloved, decade-old social network

Ello launched in 2014 with big dreams to avoid advertising and retain a user-friendly, simple style. But in 2023, the hip social network suddenly shut down, removing nine years of posts with no warning. Artists, writers, and other creators lost nearly a decade of work with no explanation. Read the troubling story here.

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.

In 2025, American Express paid $230M to settle fraud and deceptive marketing charges

American Express launched a wire payment service targeted at small businesses and falsely touted the service as a tax-deductible business expense in 2018. American Express was also accused of allowing small businesses to open corporate credit cards without the necessary employer identification number (EIN).

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

Elon Musk cofounded "X.com," an online banking service, in 1999 with the idea that the web would become a financial repository as internet access expanded and became ingrained in daily life. Peter Thiel cofounded "Confinity" as a digital security service that morphed into a payments system. In 2000, the two merged to form PayPal, and in 2002, they sold PayPal to eBay for $1.5B.

A merger between OpenAI and Anthropic was reportedly proposed after Sam Altman's firing

OpenAI's board of directors reportedly reached out to Anthropic's CEO, Dario Amodei, about the possibility of taking over the role left by Altman in 2023. Amodei declined to take over as OpenAI's CEO and to a merger of the two AI startups.

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.

See a timeline of American Express' history

Since its founding in 1850, American Express has evolved from a mail delivery service to a multinational financial services company. Small additions to the company over time, such as taking money orders and inventing traveler's cheques, were key drivers of the company's transformation.

Creating the iPhone ended the marriages of several of Apple's engineers

In the early 2000s, Apple recruited multiple engineers onto rival teams tasked with combining phone, internet, and iPod capabilities. Despite significant technical hurdles, Steve Jobs favored a prototype with multitouch technology and a modified Mac operating system over a competing in-house model based on the iPod's click wheel. (Some users may experience a paywall.)

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.

American Express runs on a 'spend-centric' model, using perks and merchant fees to drive profit

American Express cardholders tend to spend more money per transaction than other credit card users, which makes the interchange fees merchants have to pay to accept American Express cards worth it while incentivizing other companies to pay the interchange fee as well.

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.

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.

How 'Don't leave home without it' became the American Express tagline

The tagline was created by legendary New York advertising firm Ogilvy & Mather. Its first commercial was fronted by Karl Malden, famous for his role in the TV show "The Streets of San Francisco." The slogan was originally designed for American Express traveler's cheques, but was revived for the company's credit cards. (Some users may experience a paywall.)

The first compiler to facilitate communication with computers was developed by Grace Hopper

The A-0 program linker automatically translated mathematical symbols into machine-readable binary code. Although it took two years for computer executives to get on board with the idea, the technology was foundational to future programming languages that allowed computers to understand commands written in word-based languages.

American Express stopped its rail service when President Wilson seized American railroads

After the US entered World War I, the federal government took control of American railways and consolidated rail companies. American Express officially exited the express shipping business in 1918 and turned its focus to its travel and financial services.

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

Electronic trading transformed investing, ushering in a new era for retail investors in which average Americans could research stocks online and then use early platforms like StreetSmart and E-Trade to conduct their transactions

In the early 1990s, stock brokerages knew that online trading would be a great equalizer, creating opportunities for more individuals to buy and sell stocks.

Microsoft paid $50k for the foundation of the OS they licensed to IBM

Rather than write MS-DOS from scratch, Bill Gates purchased the full rights to QDOS—Quick and Dirty Operating System—from Seattle Computer Products only weeks before IBM's PC hit the market. The IBM deal allowed Microsoft to license its OS to other manufacturers, ensuring it was not dependent on IBM's long-term success.

The pandemic saw Zoom overtake Skype as the default video conferencing tool

When millions of people needed to become work-from-home experts overnight, ease of use for video conferencing tools became especially important. Zoom's success was partly because the company made it easier to join meetings than Skype did—with Zoom, users only needed a URL to join a meeting, rather than downloading a fully separate app as they did on Skype. (Some users may experience a paywall.)

In defense of the advertisement economy

Advertising is frequently reviled for how it clutters up public spaces and our everyday experiences. Nonetheless, it allows for vast amounts of goods and services to be rendered free to millions of users—and gives users the option to pay with money or time and attention.

Chat with famous, historical, and fantasy figures with this chatbot

Character.ai—a generative AI-based chatbot platform—allows you to have free-flowing conversations with a wide range of people. From celebrities to famous figures from the past, the platform relies on a neural language model to process huge amounts of text, learning from conversations with users to develop responses. A number of observers have referred to the platform as "making AI fun," with user time on site surpassing a whopping two hours per day.