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 dot-com boom sent tech stocks soaring before a historic collapse

A look at the dot-com bubble, when investors poured money into unproven internet startups, driving the Nasdaq to dizzying heights before it crashed by more than 80% after 2000, showing how new technologies can detach markets from reality.

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.

See which companies folded and which survived the dot-com crash

Companies that primarily used the web as a platform for doing business were more vulnerable than companies that created technology. While hardware and software companies managed to make it to the other side, most e-commerce companies took a brutal beating and share prices plummeted.

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.

Listen to the history of the first banner ad on the internet, which went live on Oct. 27, 1994, on HotWired.com and pioneered the modern concept of digital advertising.

The dot-com bubble burst in 2000 when the Nasdaq dropped more than 76% in roughly 2 years

Between 1995 and 2000, the Nasdaq Composite index jumped from roughly 1,000 to 5,000 amid excitement over new internet companies. As venture capitalists dumped money into startups, those same companies struggled to turn a profit, leading to a bubble. The Nasdaq wouldn't reach its former high until 2015.

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.

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.

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

Internet domain names can be worth millions of dollars

And yet, the mysterious man who owns Milk.com likely isn't selling his valuable site any time soon.

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.

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.

Many dot-com companies spent some investor money on expensive parties

Parties hosted by dot-com companies were known to be extravagant and expensive. Technology companies in the Bay Area hosted between 15 and 20 parties a week on average, which cost between $30K and $50K on average.

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 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.

The term 'startup'—which is typically used to describe private companies in their early stages of operation that focus on innovating new products or services to meet a market gap—can be traced back to a 1976 Forbes article.

Theranos and Pets.com are among some of the biggest startup failures ever

You might have heard of Theranos, Elizabeth Holmes’s one-time blood testing company that landed the founder in prison for more than a decade after she was charged with fraud. The rest of the startups on a list of five of the biggest startup failures ever might not be as famous as Theranos, but they were met with similarly disastrous fates.

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.

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.

Visualize where the first batch of founders from the famous startup accelerator Y Combinator are now.

See the original websites for companies like Google, Facebook, and Apple

Explore archived images of homepages on websites dating all the way back to 1991.

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.

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.

IPOs that failed

Plenty of private companies fail once they try to go public. Failing can mean shares sell for less than their initial asking price on its IPO date, or it can look like a company pulling out of the IPO process at the last minute. Some companies with failed IPOs include Pets.com, Etsy, and Robinhood. Learn more about these companies and others here.

Watch a medley of Pets.com commercials with the famous sock puppet mascot

Pets.com used a sock puppet decorated like a dog (operated by comedian Michael Ian Black) as the company's mascot. The sock puppet became synonymous with the brand. An auto lender company called BarNone Inc. later purchased the sock puppet for $125K and rebranded it with the slogan "Everybody deserves a second chance."

'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.

Warren Buffett has been criticized for avoiding investing in tech stocks during the 1990s dot-com boom, as he wasn't confident in the future growth of the tech industry.

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.

Google's early focus on simplicity and user experience drove its future successes

Google Search revolutionized information retrieval in 1998, but additional web-based products, including Gmail, Maps, Docs, and YouTube reinforced the company's core ad business while allowing it to aggregate the world's information. Forming Alphabet protected this business from riskier moonshot projects.

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.

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.

7 prominent investors rejected Airbnb in its early days

Airbnb is arguably known as one of the most successful startup stories of all time. But back in 2008, many prominent investors rejected their pitch when they went out to raise money—and Airbnb's founder still has the rejection emails to prove it.

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.

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.

PetSmart and Hilton are among 10 of the most famous leveraged buyouts in history

Some of the most famous leveraged buyout deals include Blackstone's 2007 acquisition of Hilton Hotels, in which Blackstone took the then-public company private and then returned it to the public markets in 2013. A British PE firm bought PetSmart for $9B in 2014—one of the most expensive leveraged buyouts since 2007.

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.

Amazon expanded its business and diversified its offerings by acquiring companies

Amazon’s retail and cloud businesses have been key drivers of the company’s growth over the years, but they haven’t done all the work by themselves. Companies Amazon has acquired include the video doorbell maker Ring, the grocer Whole Foods, the streaming service Twitch, the shoe retailer Zappos, and the film studio MGM.

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.

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.

When a radio company was the biggest tech stock around

The Radio Corporation of America was the biggest stock during the 1920s. Originally called Marconi Wireless, the company transformed radio technology. The company pioneered broadcasting, created NBC, and became a tech giant. After remarkable growth and challenges, RCA was acquired by General Electric in 1986, marking the end of its 67-year independent existence.

Frisbee, Jet Ski, and Dumpster—explore a list of words you might not realize are trademarked

Many products that have become household names started out as first-of-a-kind items. As those products grew in popularity, the brand name became the default name for the product.

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

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.