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In February-March 2008, leaked instant-message transcripts showed Jimmy Wales communicating with Fox News commentator Rachel Marsden about edits to her Wikipedia biography while the two were developing a romantic relationship, which he did not fully disclose to Wikimedia's OTRS volunteer team. In one leaked message Wales wrote, 'The truth is of course a much worse conflict of interest than that :) but that will do,' acknowledging the conflict while misrepresenting it internally. Wales maintained he acted consistently with Wikipedia policy and had disclosed a conflict, but the episode was widely reported as a breach of the neutral-point-of-view and conflict-of-interest norms Wales himself championed as Wikipedia's founder.

In June 2007, Whitman allegedly shoved subordinate Young Mi Kim, an eBay communications employee, while preparing for a Reuters interview. Whitman said 'In any high-pressure working environment, tensions can surface.' Matter was resolved with $200,000 settlement.

The Internet Archive operates Open Library, a wiki-editable library catalog aiming to have 'a web page for every book ever published.' The platform has over 20 million book records and lends approximately 70,000 books per day to users worldwide. The Archive has digitized over 2 million books and scans 4,300 books daily across 18 locations.

In 2007, when the FBI issued a National Security Letter demanding personal information about an Internet Archive user, Kahle refused to comply silently. He worked with the ACLU and EFF to challenge the NSL as unconstitutional, helping establish legal precedent for challenging these secretive government demands for user data.

Resig created jQuery in 2006, which became the most widely-used JavaScript library and fundamentally simplified cross-browser web development. Released under the MIT license and later stewarded by the jQuery Foundation (now OpenJS Foundation), it demonstrated the power of community-driven open source development.

Greylock Partners led a $25 million financing round for Facebook in April 2006, investing $12.7 million when the platform was still in its early stages. Partner David Sze joined Facebook's board. Facebook/Meta later faced extensive documented harms including data privacy violations (Cambridge Analytica), mental health impacts on teens, misinformation amplification, and content moderation failures. Greylock has not publicly criticized Meta's documented harms despite being a major early investor.

In 2006, Bobby Kotick allegedly left a voicemail on his assistant's phone threatening to 'have her killed.' Kotick apologized, and the dispute was settled out of court. This incident was reported in the November 2021 Wall Street Journal investigation into Kotick's knowledge of workplace misconduct at Activision Blizzard.

Since its founding in 2005, Automattic has operated as a fully distributed company with no central office, employing workers across 90+ countries. The company has been widely cited as a model for remote work, offering stipends for home office setups, co-working spaces, and annual meetups. CEO Matt Mullenweg has been a vocal advocate for distributed work as an equity practice.

Automattic has been the primary corporate contributor to WordPress, the open-source CMS that powers over 40% of all websites. The company employs numerous WordPress core contributors and sponsors WordCamp events globally. Automattic's commercial products (WordPress.com, Jetpack, WooCommerce) are built on top of the open-source project, and the company has historically championed GPL licensing.

Development of Git began on April 3, 2005 after BitKeeper revoked free access. Torvalds built Git in roughly 5 days and released it in April 2005 under GPL-2.0. By 2022, nearly 95% of developers used Git as their primary version control system. Git became self-hosting on April 7, and managed kernel 2.6.12 release by June 16.

From 1998-2002, Whitman participated in 'spinning' - receiving privileged access to over 100 hot IPOs from Goldman Sachs in exchange for eBay bond business. Practice was banned in 2003 as corrupt. Congressional investigation in 2002 called transactions 'rigged and corrupt.' Whitman settled in 2005, disgorging $1.78M profit without admitting wrongdoing. Goldman also put her on its board in 2001, paying $475K for one year before she left during probe.

Cisco sold networking equipment used in China's Golden Shield Project (Great Firewall) beginning in the early 2000s. Plaintiffs allege Cisco custom-built surveillance tools that enabled Chinese security services to identify, track, and persecute Falun Gong practitioners. A 2006 Congressional hearing examined Cisco's role alongside Google, Yahoo, and Microsoft. Cisco maintained it sold standard networking equipment and did not customize products to facilitate censorship or repression.

David Heinemeier Hansson created Ruby on Rails in 2004 and released it as open source software. Rails became one of the most influential web frameworks, popularizing conventions like MVC architecture and 'convention over configuration.' It spawned an enormous open source ecosystem and was used to build early versions of Twitter, GitHub, Shopify, and Airbnb.

Matt Mullenweg co-created WordPress in 2003 as open source software under the GPL license. WordPress grew to power over 40% of all websites globally. Mullenweg founded the WordPress Foundation and Automattic contributed thousands of hours weekly to the open source project (prior to the 2025 reduction to 45 hours/week).

Peter Thiel co-founded Palantir Technologies in 2003, which became a major provider of surveillance and data analytics tools to US government agencies including ICE, the Department of Defense, and intelligence agencies. Palantir built the Investigative Case Management system used by ICE to track immigrants, and its FALCON database was used in immigration raids. Federal contracts grew from $4.4M in 2009 to $970.5M in 2025. Thiel remains a board member and major shareholder.

In May 2003, W3C adopted a formal Patent Policy ensuring that web standards could be implemented on a royalty-free basis. Berners-Lee stated: 'W3C Members who joined in building the Web in its first decade made the business decision that they, and the entire world, would benefit most by contributing to standards that could be implemented ubiquitously, without royalty payments.'

Baker served as Mozilla's leader from the early 2000s through 2024, overseeing Firefox's development as an open source browser and championing the open web, privacy, and internet standards. Under her leadership Mozilla maintained its commitment to open source principles and internet freedom advocacy.

Between July 1998 and June 2002, five DRAM manufacturers including Micron, Hynix, Infineon, Samsung, and Elpida participated in an international price-fixing conspiracy. Micron received immunity from the DOJ for being the whistleblower that exposed the cartel. Other participants paid hundreds of millions in fines and executives served prison time.

At the 2002 FOSDEM conference in Brussels, FSF President Richard Stallman presented Guido van Rossum the FSF Award for the Advancement of Free Software 'for inventing and implementing as Free Software the Python programming language.' This recognized Python's contribution to the free software movement and its design goal of being open source so anyone can contribute to its development.

The Internet Archive launched the Wayback Machine in 2001 to address the problem of web content vanishing. By October 2025, it reached 1 trillion archived web pages - a 'civilization-scale milestone' preserving digital history that would otherwise be lost. The service is free and used by researchers, journalists, lawyers, and the public worldwide.

In May 1998, the DOJ and 20 state attorneys general sued Microsoft for illegally maintaining its Windows monopoly by bundling Internet Explorer and crushing competitors including Netscape, Java, and Linux. In April 2000, Judge Jackson found Microsoft committed multiple Sherman Act violations and ordered a breakup. The breakup was overturned on appeal in June 2001 due to judicial conduct issues, though findings of fact were upheld. Microsoft settled in November 2001, agreeing to establish an antitrust compliance program.

As CEO and chairman, Bill Gates led Microsoft during the landmark 1998-2001 DOJ antitrust case. The trial resulted in Judge Thomas Penfield Jackson ruling that Microsoft violated antitrust laws by bundling Internet Explorer with Windows to stifle competition from Netscape. Gates personally testified in the trial. The EU subsequently fined Microsoft $2.4 billion (2004-2007) and an additional $1.4 billion (2008) for abusing its dominant market position.

Lattner created the LLVM compiler infrastructure (2000), the Clang compiler (2007), and Swift programming language (2014), all released as open source. LLVM became the foundation for compilers across the industry. Swift was open-sourced by Apple in 2015. These projects have had enormous impact on software development.

Through the Bill & Melinda Gates Foundation, Bill Gates has committed over $50 billion to global health initiatives since 2000, including major programs to eradicate polio, reduce malaria deaths, and improve vaccination access in developing countries. The Foundation became the largest private funder of the WHO and a dominant force in global health policy.

W3C developed the Web Content Accessibility Guidelines (WCAG), the global standard for web accessibility adopted by governments and organizations worldwide. WCAG ensures websites and applications are usable by people with visual, hearing, motor, and cognitive disabilities. W3C's accessibility work has won three Emmy Awards (2016, 2019, 2022) for the impact of its standards.

Since its founding in 1999, Salesforce has committed 1% of its equity, 1% of its product, and 1% of employees' time to charitable causes. Over 20+ years, this has resulted in over $240 million in grants, 3.5 million hours of community service, and product donations to 39,000 nonprofits and education institutions. The model inspired the Pledge 1% movement, with over 18,000 companies participating.

Sacks joined early-stage startup Confinity (later PayPal) in 1999, serving as first product leader then COO. He built and ran many of the company's key teams including product management and design, sales and marketing, business development, international, customer service, fraud operations, and HR. His operational leadership helped scale PayPal during the critical early internet payments era before eBay acquisition in 2002. Later became part of the 'PayPal Mafia'—founders and early employees who went on to found other successful technology companies.

Marc Andreessen co-authored NCSA Mosaic in 1993, the first widely used graphical web browser that made the internet accessible to non-technical users. He co-founded Netscape Communications in 1994, whose Navigator browser drove mainstream internet adoption. In 1998, Netscape released its browser source code as the Mozilla project, which eventually became Firefox. These contributions were foundational to the modern internet, democratized access to information, and made a significant contribution to open source software.

When Softbank acquired 80% of Kingston Technology in 1996 for $1.5 billion, co-founders John Tu and David Sun distributed $71.5 million in bonuses to their approximately 550 employees, averaging roughly $130,000 per person. Kingston was subsequently named Fortune's #2 Best Company to Work For in America in 1999 and appeared on the list for 5 consecutive years (1998-2002).

In 1996, Brewster Kahle founded the Internet Archive as a nonprofit digital library with the explicit mission of providing 'universal access to all knowledge.' He funded it with proceeds from selling his previous companies (WAIS to AOL for $15M, later Alexa to Amazon for $250M). The Archive was designated as an official library by California in 2007.