The Zune struggled with a limited music store, clunky software and poor timing

Explore an illustrated history of the iPod, the Apple music player that entered listeners' pockets in 2001 and underwent several hardware redesigns before being discontinued in 2022 in favor of the iPhone.

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.

Microsoft developed the Xbox to compete with Sony's all-in-one entertainment hardware

The video game console originated as a side project between four DirectX developers, from whom the console's original name, "DirectX Box," derives. These developers sought to counter Sony's PlayStation product line, which they saw as capable of capturing all entertainment markets by playing games, CDs, and DVDs.

Watch Steve Jobs unveil the first iPhone in 2007

During his Macworld San Francisco 2007 keynote address, Jobs claimed Apple had reinvented the phone by integrating phone capabilities with internet access and music playback from its iPod product line. The multitouch display eliminated the need for a stylus or keyboard hardware typically found on other smartphones.

The first smartwatch was made by Microsoft in 1994

Coproduced by Timex, the Timex DataLink 150 featured a small LCD screen and could transfer data to and from a Windows PC. Like the Windows XP Tablet that launched in 2002, the smartwatch did not sell well, and both products are considered to have been released before their time.

Apple, the tech giant renowned for products like the iPhone, iPad, and Mac, started out in a garage in 1976.

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.)

Explore the history of the iPhone from 2007 to 2023.

Spotify took 18 years to reach profitability—and 70% of its revenue goes to rights holders.

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.

Watch Steve Jobs introduce the first iPad

Apple's cofounder debuted the first iPad in 2010, framing it as a third category of personal electronics between the laptop and the smartphone. Steve Jobs showed off how thin the device was (for the time) and explained how it was better than smartphones and laptops for browsing the web.

Explore a breakdown of 18 influential Apple products

The launch of the MacBook Air in 2008 popularized the ultrabook category of laptops, while the iPad (2010) made large-screen mobile devices a technological norm. The iPhoneX (2017) introduced the notch, which has become a staple at the top of many smartphone displays.

View an illustrated history of Microsoft Solitaire, first released as part of the Windows 3.0 operating system in 1990 to help users get familiar with using a mouse.

How Apple's GarageBand changed music

Apple's preinstalled, easy-to-use software GarageBand was first released in 2004. Since then, it's changed the way artists write and record music. The program's accessibility and ease of use have allowed beginner artists to experiment and find their voice, while major artists like Rihanna, Grimes, and Bjork have used the program to record hit singles and perform live. This article from the Red Bull Music Academy explains how the basic interface reshaped an industry.

The moment Bill Gates and the Rock announced the original Xbox at CES 2001

At CES 2001, Bill Gates and Dwayne “The Rock” Johnson took the stage to unveil the original Xbox. This memorable moment marked Microsoft’s entry into gaming and set the tone for its console brand.

The iPhone's impact in 10 charts

It's been almost 20 years since Steve Jobs first unveiled the iPhone, the device that would come to define Apple for years and change not just the smartphone industry but the world at large. 10 examples of the iPhone's impact include its all-screen touch interface and the way it led to the rise of app culture.

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.

Steve Jobs changed the world with Apple and Pixar

The devices Jobs introduced during his time at Apple, including the iPad and iPhone, were imitated by competitors, ultimately helping to create the numerous options consumers have today. In addition to leading Apple, Jobs also helped turn Pixar and the software startup NeXT into success stories.

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.

Introduced in 1981 for $1,795, the Osborne 1 was the world's first commercially successful portable laptop, despite weighing 24.5 pounds and having no battery.

By 2005, Microsoft may have made as many as 12,000 millionaires

Stock options given to early employees also created four billionaires, including Bill Gates, who became the then-youngest self-made billionaire at the age of 31. As of 2025, Microsoft employs about 228,000 employees, including more than 50,000 at its headquarters in Redmond, Washington.

The Macintosh popularized GUI and mouse navigation for personal computing

A graphical user interface that utilized windows, icons, and pull-down menus, rather than text-based commands, contributed to the device's success after its January 1984 launch. Its original sound system—capable of playing four voices—was developed after non-technical staff suggested the machine should play music.

Traditional bands largely disappeared from the Billboard charts in the 21st century, mostly replaced by solo artists.

The Beatles sued technology company Apple in 1978 to defend naming rights to their record label, Apple Corps.

Although no longer the dominant format, CDs are increasingly popular with younger people.

Steve Jobs once explained why iPhones can’t be made in the US

In 2011, then-President Obama asked Steve Jobs, “What would it take to make iPhones in the United States?” Steve Jobs said it wasn’t a viable option, explaining that overseas factories had far outpaced the US’s in terms of skill and speed.

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.

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.

Elon Musk's first company was an online business directory called 'Zip2'

Musk started the online alternative to Yellow Pages in 1995 with his younger brother. Musk sold the company for $305M in 1999.

Lessons learned from Steve Jobs

From predicting our screen-filled future in 1983 to slashing Apple's product line in 1997, Steve Jobs believed in focus, simplicity, and the fusion of technology and art. His philosophies still influence how products are built and marketed today.

Long before Coachella, Steve Wozniak attempted a similarly-minded festival

In 1982, Apple cofounder Steve Wozniak was on a hiatus from Apple after a near-fatal plane crash. In his spare time, he decided to throw a festival that would bring together cutting-edge music and technology—a Woodstock for the 1980s. The result was the US Festival, an early ancestor of Coachella that brought world-class acts like Tom Petty, Fleetwood Mac, Talking Heads, the Grateful Dead, and the Ramones to a rustic venue outside Los Angeles.

Hip-hop gained significant popularity in the 21st century, dominating Billboard's pop chart.

Microsoft Office debuted on the Macintosh in 1989

Over 15 months before its debut on Windows, the suite included Microsoft Word, Excel, PowerPoint and Mail—the precursor to Outlook. Bill Gates saw the Mac as a testing ground to work out bugs and gather feedback before the Windows release.

Explore an emulated demo of Windows 95 Microsoft Plus to try your hand at Solitaire, 3D Pinball Space Cadet, and other classic Windows applications.

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 Rolling Stones were paid $3M to have 'Start Me Up' in the Windows 95 promo

The fee was part of Microsoft's $300M advertising and promotional campaign for the operating system, which featured the Start button for the first time. The company also filmed sitcom-style infomercials featuring "Friends" TV stars Jennifer Aniston and Matthew Perry.

The first Coachella lost $1M

Coachella is now the premier live music festival in the US, but it almost didn't survive its financially catastrophic first year, which featured extreme heat and attracted only 50,000 attendees. The festival did not return until 2001—thanks to entertainment company AEG, which purchased Goldenvoice and provided the capital needed to continue.

In 1999, Microsoft and Intel’s addition signaled the information tech era for the Dow

Microsoft and Intel became the first information technology firms added to the DJIA. Their inclusion marked a turning point—the digital revolution and tech began to drive the American economy.

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.

Peloton pays artists more for music than most streaming platforms because the on-demand classes are technically live performances, so Peloton has to pay both for the rights to the song itself and for the right to actually play the song.

Digital coupon platform Groupon IPO'd in 2011 at a $17.8B market cap, but as of 2024 was worth just $103M—a 99.4% decrease.

Car touchscreen debuted on 1986 Buick Riviera, but flopped

Preceding car infotainment centers by decades, the technology that was unveiled in the Buick elicited praise from auto journalists, but consumers did not make investments in the cars.

See which Apple products drive the most of its $391B revenue.

In 2025, Weight Watchers filed for Chapter 11 bankruptcy after reporting revenue and profit losses for multiple consecutive years, with its stock price losing about 99% of its value between 2018 and 2025.

Unsatisfied with the designs provided by an Apple engineer, Steve Jobs designed the original Mac calculator in about 10 minutes.

The payments tool Zelle was created by big banks to compete with apps like Venmo

Zelle is an alternative to Venmo, where people can pay each other back for expenses like apartment utilities or dinner. But its origin story has more to do with big finance than small transactions.

As of 2024, server products and cloud services make up 40% of Microsoft's revenue

These products generated $97.7B in the 2023-24 fiscal year, followed by office products and cloud services, which accounted for $54.9B during the same period. The fastest-growing revenue source was gaming at 39%, driven by sales of Xbox and first-party software.

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.

Amazon didn't have a profitable quarter until 2001, more than 6 years into its existence

Jeff Bezos, however, took pride in Amazon's early unprofitability, reinvesting the money Amazon made back into its business, prioritizing investment into long-term growth and customer acquisition over short-term gains.

Why Metallica sued Napster—and enraged music fans

When Lars Ulrich, the drummer for metal legends Metallica, began his press campaign against Napster, an early filesharing software, he said he was fighting for artists. Listeners weren't convinced, especially because data suggested that filesharing services helped record sales rather than hinder them. This history of the ordeal contextualizes more modern problems in the music business, especially considering streaming services like Spotify were initially seen as a solution to illegal filesharing.