The dot-com boom made Mark Cuban a billionaire

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 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.

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.

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.

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.

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.

Uber's first investors included StumbleUpon founder Garrett Camp

In 2010 when Uber went out to raise money, prominent investors including Mark Cuban and Gary Vaynerchuk passed. Vaynerchuk actually said no twice.

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.)

Y Combinator tends to outperform many other Silicon Valley startup accelerators

In a podcast episode, Garry Tan—CEO of startup accelerator Y Combinator—speaks about how YC has a better track record than the rest of Silicon Valley at placing bets on startups. Learn how Tan earned his first million dollars, as well as lessons from other successful businesspeople, including Y Combinator’s Paul Graham.

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.

'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.

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.

The dot-com stock bubble taught Howard Marks about markets

Annual investment letters from Howard Marks, the billionaire cofounder of top distressed debt shop Oaktree Capital Management, are required reading on Wall Street. The prolific writer and investor explains the distinction between the folly of trying to time the market and the necessity of paying attention to market cycles. The difference makes all the difference in returns.

A quick history of Tencent

The Chinese tech firm grew from a late 1990's internet messaging service to a globally influential conglomerate. It was China's first company to hit the $500B valuation mark, and now enjoys massive reach via WeChat, WeBank, and its robust investment portfolio.

YouTube brought endless content—and endless culture wars

How did YouTube grow from a startup in 2005, to a media powerhouse with more than 2.5 billion monthly logged-in users who watch more than 1 billion hours of video every day? That’s what this podcast interview with Bloomberg tech reporter Mark Bergen on NPR’s Fresh Air explores.

Bumble went public with an IPO in 2021

That year, Bumble Founder Whitney Wolfe Herd became the youngest female CEO to ever take a company public. The company pivoted during the 2020 COVID-19 pandemic lockdowns, focusing its marketing strategy on promoting social-distanced dating and its video chat features.

How to make a billion dollars, with Brad Jacobs

Brad Jacobs is a serial entrepreneur who has launched eight billion-dollar enterprises during his storied financial career. With companies focused in energy, waste, and more, Jacobs has stuck to a roll-up playbook of consolidating small players into one conglomerate within an industry, a common tactic of similar private equity firms. This podcast from Founders summarizes Jacobs' book detailing his approach.

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).

See the small apartment WeWork founder Adam Neumann lived in before he was a billionaire

WeWork CEO Adam Neumann used to share a relatively small apartment in New York City with his wife before he became a billionaire off of WeWork. At one point, the apartment rented for $3K per month.

Steve Jobs saved a nearly bankrupt Apple

Apple nearly went bankrupt in 1997, when the tech company had only three months of operational cash left. Apple's board ousted cofounder Steve Jobs in 1985, but he was brought back as interim CEO to revive the company when Apple purchased Jobs' company, NeXT.

Ray Dalio started his career as a golf caddy in Long Island

When Dalio was 12 years old, he worked as a golf caddy at the Links Golf Club. That's where he heard about the stock market for the first time and decided to invest in Northeast Airlines—the only stock he knew that was selling for less than $5 a share. Dalio ended up tripling his profit and became fascinated with the stock market—ultimately laying the foundation for his legendary career as a hedge fund manager.

Track Warren Buffett’s real-time net worth

Buffett is worth many, many billions of dollars. As a self-made billionaire, he is the eighth-richest man in the world, and his real-time net worth changes daily.

Hear what Michael Burry thinks about the possibility of an AI bubble

Since his success shorting subprime mortgage-backed securities in 2008, Burry's positions have often become influential, sparking conversations on platforms like X. In 2025, Burry drew attention for betting against Nvidia and Palantir for being overvalued companies.

How Martha Stewart became the first self-made billionaire woman

Through her cooking shows, cookware, and media empire, Martha Stewart ascended to billionaire status in 1999, becoming America's first woman to achieve that number on her own. Despite a conviction in 2004 and time spent in prison, Stewart rebounded and continues to develop product lines and media, with an estimated net worth of $200M. Read more about her story here.

Temu aired its first Super Bowl ads in 2023

The “Shop Like a Billionaire” ad ran twice during the game. Temu saw a roughly 45% surge in downloads and a 20% increase in daily active users the day it aired.

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

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%.

SpaceX's S-1 or 'prospectus' revealed many previously unknown details about the company, including its unprofitability despite doing $18.7B in revenue in 2025, exactly how many voting shares Elon Musk will have in the company (roughly 85%), and more.

Watch this video that uses Lego bricks to explain how venture capital works.

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.

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.

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

Fast-casual restaurant Chili's is experiencing a resurgence, with its parent company recently reporting a nearly 32% increase in sales, thanks to passionate Gen Z fans on TikTok.

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.

Watch a 1934 short film starring jazz legend Cab Calloway, a major figure in the Harlem Renaissance's music scene

Jimmy Carter signed a 1978 bill that legalized home brewing, a move credited with kick-starting the craft beer industry.

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.

Exploring the Larry Bird punch that almost changed March Madness

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.

US intelligence allegedly pursued more than 600 schemes to assassinate Cuban revolutionary Fidel Castro.

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.

Fireworks make a loud booming sound after exploding due to air expanding faster than the speed of sound.

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!'

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

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.

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

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

The US first hosted the World Cup in 1994, a tournament that lives in soccer infamy for its poor planning and the murder of Colombian player Andres Escobar, who'd accidentally scored on his own net.

See a 3D reconstruction of Tenochtitlan, the Aztec capital that was home to an estimated population of 200,000 to 400,000.