WordPress / Automattic

Matt Mullenweg grew up in Houston, Texas as a broke kid passionate about jazz and economics. He attended the High School for Performing and Visual Arts (where Beyoncé also studied) and participated in the Federal Reserve Challenge, meeting Alan Greenspan and Ben Bernanke at the national competition. Because music lessons were expensive, he bartered and traded—building websites for local musicians in exchange for lessons. This exposed him to open-source software and shaped his philosophy around digital freedom.

Inspired by the open-source ethos he discovered through Slashdot and web standards advocates like Jeffrey Zeldman, combined with his liberal arts education in philosophy and economics, Matt came to believe that open-source was "the most important idea of our generation." He saw software freedom as fundamental to human liberty: as code increasingly controls our lives, we must have the freedom to see how it works, modify it, and share those modifications.

At 19, Matt co-founded WordPress with Mike Little as a fork of B2, an abandoned open-source blogging platform. He was already a volunteer contributor to B2 and saw an opportunity when it was abandoned. WordPress launched as blogging software but evolved into a full-fledged site builder and content management platform. The project grew organically within the open-source community, eventually powering over 40% of all websites—10x the market share of its nearest competitor (Shopify at 4%).

After working as a product manager at CNET for a year, Matt had a vision: instead of forcing users to download WordPress, set up databases, and manage servers themselves, why not offer it as a hosted SaaS service? When Automattic (his then-employer) showed no interest, he left to start his own company.

Matt started Automattic 19 years ago with the mission to create commercial services that complemented the open-source WordPress core. Rather than competing with the software itself, Automattic offered cloud-based features like Akismet (an AI-powered anti-spam system) and Jetpack (described as "iCloud for WordPress," providing backups, real-time sync, and other utilities). This complementary approach worked. An early meeting with Mark Andreessen was brutal—Andreessen grilled him for an hour on how you could build a business on open-source, in a fully distributed team, when every great Silicon Valley company had offices. Matt thought it was a disaster until the next day when Andreessen called interested; he had been battle-testing their ideas.

Automattic's distributed, remote-first culture—established from the start—became a superpower. The company grew to 1,700+ employees across 90 countries. The ecosystem was key: 60,000+ plugins and themes built on top of WordPress created a true platform. Unlike proprietary platforms (Facebook, Shopify) that have historically pulled the rug out from under successful third-party developers, WordPress's open-source GPL license guaranteed that developers always owned their work. This asymmetry drove adoption.

WooCommerce, an open-source e-commerce engine, became a major acquisition and now represents over half of Automattic's revenue. The company also acquired Tumblr (later described as "the hardest thing I've ever attempted" due to content moderation complexity), and products like Day One, SimpleNote, and Pocket Casts—all aligned with an ethos of privacy and open-web values.

What hasn't worked as well: some of Automattic's products have accumulated technical debt. Matt admits being "the unhappiest WordPress user in the world" due to outdated UX in certain areas and has made improving core user experience a 2024 priority.

WordPress powers 40% of the internet, including WhiteHouse.gov. Automattic is valued at over $7 billion and operates as a fully distributed company. Matt remains deeply involved: he leads the WordPress project itself (managing releases, community, plugin/theme directories), sits on the board of Illuminate (a nonprofit doing radical public art in San Francisco, including the Bay Lights project on the Bay Bridge—which he personally mortgaged his condos to fund), manages Autric Capital (a personal investment vehicle with 100+ angel investments including Stripe and SpaceX), and co-owns Keys Jazz Bistro in San Francisco.

Recently, conflict has erupted with WP Engine, a major WordPress host acquired by private equity firm Silver Lake in 2019. WP Engine disabled core WordPress features (like post revisions/undo) to save money and used WordPress branding in ways that confused customers into thinking it was official. After failed negotiations over trademark licensing, WP Engine sued Matt and Automattic for millions, while simultaneously spending heavily on lawyers and PR. Matt sees this as emblematic of private equity's tendency to hollow out open-source projects for short-term profit, and he's using the conflict as a rallying cry for the open-source community to defend itself against this pattern.