Yahoo acquired Paul Graham's former startup Viaweb in 1998

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.

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.

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.

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 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.

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 software for wikis—user-editable websites—was launched in 1995

Computer programmer Ward Cunningham created the WikiWikiWeb online application based on an offline system that helped track how ideas moved through his company. The application enabled users to collaborate and edit website content through a web browser, as well as link pages without requiring a structured navigation scheme.

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.

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).

'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 was famously anti-tech stock during the 1990s dot-com boom

Buffett said that tech is something that Berkshire Hathaway doesn't "understand, so we don't invest in it." This philosophy led him not to invest in Yahoo or Microsoft during this time. (Some readers may experience a paywall.)

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.

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.

Bumble was originally created under the MagicLab parent company

When Blackstone acquired MagicLab in 2019, Bumble Founder and CEO Whitney Wolfe Herd was elevated to CEO of the entire parent company (which also owned Indian dating app Badoo). The parent company was rebranded as Bumble Inc.

Sophia Amoruso's company Nasty Gal was worth $100M at its peak

In 2006, Sophia Amoruso started an eBay shop that would later transform into the clothing company Nasty Gal. However, Amoruso’s rags-to-riches success with Nasty Gal didn’t last. After multiple rounds of layoffs and employee complaints, the company filed for bankruptcy in 2016.

Groupon was a digital coupon platform popular in the 2010s

Remember when everyone you knew seemed to have a Groupon for something? In August 2010, Forbes called the digital coupon platform the “fastest growing company ever.” However, the business model had some flaws: One analysis found that only an estimated 20% of Groupon buyers returned for full-price purchases.

Web3 is the successor to our current version of the Internet

Web1 (existing roughly from 1990 to 2005) was about decentralized and community-governed open protocols. Most of the value accrued to the edges of the network: users and builders. Web2 (roughly 2005 through 2020) was about siloed, centralized services run by corporations.

See Don Valentine's original 1977 memo for Sequoia's investment into Apple Computer

In honor of Apple's 50-year anniversary, Sequoia Capital recently posted a tweet on X (the social media platform formerly known as Twitter) with a photo of the original 1977 memo for Sequoia's investment in Apple.

Explore Bessemer's anti-portfolio of missed opportunities

From Pinterest to Yelp, Bessemer Venture Partners—one of the most well-known VC firms—has invested in many successful companies over the years. But the firm has also kicked itself for passing on a few great opportunities, like Apple and Google. Check out the other companies in Bessemer's "anti-portfolio" here.

The main bank serving Silicon Valley startups and venture capitalists collapsed in 2023

Silicon Valley Bank—the 16th largest bank in the US—served many tech startups in the area as well as many venture capitalists. The bank collapsed in 2023—in a single day, bankers took out $42B.

Sam Altman gave his first-ever startup pitch after dropping out of Stanford

He dropped out of Stanford to start Loopt, which sold in 2012 for $43.4M. You can watch his first-ever startup pitch in a video.

From 1986 to 2024, Microsoft has acquired at least 277 companies

Some of these acquisitions helped the company expand into enterprise software and services, including Visio, which integrated diagramming software into Microsoft Office, and Hotmail, which provided an email platform to customers. Recent acquisitions of Mojang and Activision Blizzard underscore an increasing emphasis on the video game industry.

Advertising holding company WPP acquired Ogilvy & Mather in 1989 for $864M

It was the largest amount ever paid for an agency at the time. WPP, which acquired agency J. Walter Thompson for $566M just two years before the Ogilvy & Mather acquisition, still owns Ogilvy today.

WellHub is a startup serving roughly 4 million people in 11 countries, providing broad wellness benefits to employees

Valued at $2.4B in 2025, the company helps workers get gym access and meditation apps, in addition to basic healthcare. Listen to the founder of the company, Cesar Cevalho, explain how he scaled the company with Jeff Berman.

WeWork filed its first S-1 in 2019

When WeWork prepared to file for its initial public offering in 2019, its S-1 revealed its poor financial state to the public.

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

A vending machine run with Anthropic's AI went out of business after it was convinced to give away items for free and sell a video game console.

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

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.

In 2019, a laptop loaded with six of the worst malware in history and described as 'an exhibit of historical weaponry' sold for $1.3M.

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

A Yale student wrote a profound essay about the consulting industry's influence on elite college students that was published in a book of her writing after she died in a post-graduation car accident.

In its famous catalog, Sears sold $600 DIY house kits from 1908 through the 1940s, resulting in an estimated 100,000 'Sears and Roebuck homes.'

Legendary architect Frank Lloyd Wright designed the SC Johnson headquarters in Wisconsin, aiming to make a cathedral-like workplace

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.

After 25 people used virtual reality headsets to practice flying with virtual wings—flapping their arms—their visual cortex responded to the wings almost as if they were real arms, treating them as body parts.

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

When a Paris department store hesitated to sell Estée Lauder's perfume, she 'accidentally' broke a bottle, causing the smell to spread throughout the store and shoppers to start asking to buy the scent.

The animatronic shark from Steven Spielberg's 'Jaws,' the first modern blockbuster, was a complex underwater apparatus called 'Bruce.'

The tragic Pulitzer Prize-winning image 'The Vulture and the Little Girl' (1993) generated controversy, raised concerns about ethics in photography, and eventually led to the photographer's death.

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%.

NBA superstar Victor Wembanyama spent the 2025 summer training with monks in central China to enhance his body and mind.

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.

An Ebola vaccine was developed during the 2018 west African Ebola outbreak, but the 2026 Ebola outbreak is with a different species of the virus, not the one that the vaccine is approved to treat.

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.'

Explore the archaeological treasures of Pompeii, the city buried under volcanic ash when Mount Vesuvius erupted in 79 CE.

Telehealth demand for GLP-1s for weight loss is booming as consumers seek easier access.

Long before Major League Baseball began allowing instant replay for balls and strikes, an umpire reluctantly used the technology to determine whether a hit was a home run, a move that inadvertently ushered in a new era for the sport.

The term 'algorithm' originated from the Latinized name of al-Khwārizmī, a 9th-century mathematician whose works introduced Arabic numerals and the decimal-based numeral system to Europe and whose treatise 'Al-Jabr' gave algebra its name.