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

Domains were like real estate in the dot-com era

In the early days of the World Wide Web, users needed to type URLs directly in the search bar to navigate to webpages (as opposed to the more general keyword search that browsers use now). This made simple, short, and intuitive domain names a hot commodity. So having a domain name, like Pets.com or Rent.com, that was easy to find and understand was like owning prime real estate on the WWW. (Some users may experience a paywall.)

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.

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.

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.

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.

Dot-com companies paid $44M for Super Bowl ads in 2000

During the 2000 Super Bowl game, 17 dot-com companies paid $44M total for ads. Just the next year, only three dot-com companies ran ads in the game. The significant drop reflects just how hard the crash hit dot-com companies and how unsustainable the businesses were.

The original 'four horsemen' of tech were Intel, Dell, Microsoft, and Cisco

These companies became known as the "four horsemen of tech" for the influence the companies had both on other businesses and investors in the late 1990s and early 2000s. The expansion of internet infrastructure throughout the 1990s and the dot-com bubble lifted these companies to incredible heights.

Many startup founders pull out-of-the-box stunts to get their businesses off the ground

Do you know Airbnb’s founders used cereal (yes, as in the breakfast food) to secure their initial round of funding? Or that PayPal’s founders once gave out free money to get people to sign up for the platform? These stories might be crazy, but they’re not uncommon.

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.

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.

How venture capital firms came to be

The venture capital firm that kickstarted an industry.

YouTube was acquired by Google for $1.65B in stock during its second year

In 2006, Google acquired YouTube for $1.65B, only two years after its launch. Sequoia Capital, one of Silicon Valley's best-known venture firms, was an early investor in the streaming video platform, seeing it as the next step in the evolution of user-generated content that flourished online during the mid-2000s.

Where are the first batch of YC founders now?

Reddit was one of the companies in Y Combinator’s first batch. While OpenAI wasn’t among the companies started at YC, Sam Altman, who would later become the AI company’s CEO, had a different company called Loopt in the first batch.

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.

Venture capitalists were once bullish on DTC brands

While a physical store can only hold so many objects, online retailers without the limits of four walls that could sell their products direct-to-consumer could theoretically be great investments. But they didn’t always provide investors with expected returns.

Warren Buffett has said not investing in Google or Amazon early enough was a mistake on his part

After avoiding investing in tech stocks during the dot-com boom, Buffett's stance on investing in tech was widely criticized. Buffett later shared his thoughts on why he regrets not investing early enough.

'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.

The Grateful Dead's online bulletin board system inspired the early internet

The legendary countercultural band the Grateful Dead had a popular hub on The Well, an online extension of the Whole Earth Catalog, a popular hippie magazine in the '60s and '70s. Users included Craig Newmark (founder of Craigslist), Steve Case (founder of AOL), and Steve Wozniak (cofounder of Apple).

Amazon sold its first book on April 3, 1995

Before selling everything on the internet, Amazon started as an online bookstore. The company's first customer was a man named John Wainright, who purchased "Fluid Concepts And Creative Analogies: Computer Models Of The Fundamental Mechanisms Of Thought" by Douglas Hofstadter. There's a building named after Wainwright on Amazon's Seattle campus.

Today's money-making influencers might not have existed without the 'mommy bloggers'

"Mommy bloggers" chronicled the realities of their lives with kids on blogs in the early 2000s. Many eventually made some serious ad dollars too.

These famous brands used to have different names

Did you know that Nike used to be called Blue Ribbon Sports? Or that Google was originally named BackRub? Getting a brand's name right is a tough job; there's an entire cottage industry of brand naming agencies to prove it. See which brands got it right the first time—and which ones might be better off with their current names—in this article.

Microsoft's initial successes came from promising products that did not yet exist

In discussions with teams responsible for MITS's Altair 8800 and IBM's PC, Bill Gates and Paul Allen claimed to have created ready-to-use software. Code for the former was not completed until Paul Allen's flight to MITS' headquarters, where the software was successfully tested for the first time.

See an image of the earliest surviving coupons used in America

This clip from the "Acquired" podcast shows an image of one of the original Coca-Cola coupons. The hosts argue that the coupons helped popularize Coca-Cola in its early days, making them a key component in the story of one of the world's most iconic brands.

The first private equity fund was launched in 1960

At the time, the industry—and the public's understanding of it—was rather limited, and few private equity firms existed until the 1980s. The first leveraged buyout is thought to have taken place in 1955.

Berkshire Hathaway's origin story is strongly intertwined with Warren Buffett's

"Acquired" is a podcast that tells company origin stories—and in one series of episodes, it dives into Berkshire Hathaway's. While the Berkshire Hathaway story ended up becoming three "Acquired" episodes instead of one, Part I explores how Berkshire Hathaway's former CEO became who he is today.

The name 'Silicon Valley' arose from the founding of Shockley Semiconductor Laboratory in Fairchild Semiconductor in 1956-57, founded near Stanford University in Palo Alto

Venture capital is a form of funding provided to early-stage companies with high growth potential, typically in exchange for an equity (or ownership) stake

The Nasdaq's 'Magnificent 7' companies are responsible for roughly 40% of the Nasdaq 100 index's gains, while the remaining 93 companies account for the other 60%.

Mid-century modern graphic designers, known for their bright colors and bold lines in advertising, also found success with children's books.

While the first exchange-traded fund (a 'basket' of different assets that can be bought and sold on a stock exchange) in the US only launched in 1993, the global ETF market has grown to more than $10T in the short time since.

Netflix profits when you're not watching, and its movies are designed that way—read a detail-rich critical essay exposing lesser-known Netflix takes

Sears sold DIY house kits starting at $600 in its famous catalog from 1908 through the 1940s, resulting in roughly 10,000 'Sears and Roebuck houses' being built.

Warren Buffett's former professor Benjamin Graham is known as the 'father of value investing,' a strategy in which investors seek to buy stocks trading below their intrinsic worth.

How Amazon operates a 'flywheel' business model, a self-reinforcing cycle that drives continuous growth

Elk Cloner, the first computer virus to spread in public, was written as a practical joke by Richard Skrenta, a Pittsburgh high school student.

Domino's Pizza's 30-minute delivery guarantee was responsible for the chain's 1980s surge, but it was discontinued after the company was found liable for delivery driver accidents.

Memecoins are a type of cryptocurrency—a form of digital currency with a wide variety of uses—created around popular 'memes,' or viral internet jokes.

Before humans, the Soviet Union and the United States sent animals—including apes, dogs, and cats—to space during the Space Race.

Walt Disney's early film 'Alice's Wonderland' was a groundbreaking innovation in the silent film era

Children are now three times more likely to say they want to be a YouTuber when they grow up than an astronaut, with some even attending 'YouTube camps' that teach kids how to create content for the platform.

The Beatles' US label rejected the band's first two singles, 'Please Please Me' and 'From Me to You,' with one executive calling the band 'dead in the water.'

Hear about the 250-year history of the United States Postal Service, complete with some of its strangest deliveries, important innovations, and the figures that made it an American institution.

After the Boston Tea Party, colonists switched to coffee, which became the main morning drink for revolutionaries.

The most expensive ad of all time was for Chanel No. 5 perfume and cost roughly $33M to produce in 2004—about $57M in today's dollars.

Budweiser stores yeast derived from the original 1800s strain in a secret bunker, which only the Head of Yeast Management can access—not even the CEO

A researcher recently discovered an interview from 1967 between groundbreaking journalist Joan Didion and the Grateful Dead, years before the band became an institution.

The first image of a black hole was captured by creating an Earth-sized virtual observatory from a network of eight radio telescopes.

'Shogun,' a 1980s TV series, helped popularize sushi in the US by stimulating an American interest in Japanese culture.

In 2009, the nation was gripped by the story of a missing young boy who was believed to be floating over Colorado in a homemade balloon, until it was revealed that he was at home the whole time.

Search a massive database of over 4 decades of clues from the TV quiz show 'Jeopardy!'