Automattic

Matt Mullenweg started WordPress in 2003 as a hobby, working on it nights and weekends instead of schoolwork. He was a University of Houston student studying jazz saxophone and gigging around town to pay bills. The blogging platform was never meant to be a business initially—it was just a passion project. About a year after launching WordPress, Matt took a job at CNET working on open-source initiatives, which gave him exposure to industry leaders like Google and Yahoo.

In 2005, roughly two years into WordPress's existence, Matt founded Automattic with the mission of building services around the open-source project. He had multiple opportunities on the table, including staying at CNET, but decided to dive fully into the startup. The company started small—just 20-25 people—with revenue in the low millions. Matt brought in Tony Mullenweg as CEO early on, a former Yahoo executive whose company had been acquired by Yahoo. Matt wanted clear leadership structure to avoid the conflicts he'd seen in co-CEO arrangements, so Tony took the top role while Matt focused on product for WordPress and core business development.

Automattic grew through the WordPress ecosystem itself. By 2010, the company had crossed the magical $10 million annual revenue mark, achieved through its three subscription-based products: WordPress.com (hosting), Jetpack (services for self-hosted WordPress), and later WooCommerce (e-commerce). The business model was straightforward—approximately 98-99% subscription revenue. WordPress itself had become ubiquitous on the web, with major publications using it. By 2012, Tony publicly shared that the company had hit $45 million in revenue with 70 million sites running WordPress and over 500,000 paying customers.

In 2008, about two and a half years after launching Automattic, Matt received a $200+ million acquisition offer. Instead of selling, he used it strategically: he went back to existing investors and raised a round at a $200 million valuation, with the New York Times participating. This allowed Matt to stay independent and give himself financial security—by age 28, he reached a point where he could retire if he wanted. Matt explained his reasoning: "I don't know if I'd want to change my life at all" and felt there was far more the company could accomplish independently.

The company's strategy of being fully distributed proved ahead of its time. Operating across 62 countries with 650 fully remote employees, Automattic had to build its own internal tools like P2 (replacing email with internal blogging) to coordinate effectively. Matt also made a strategic decision not to acquire hosting companies like WP Engine, instead focusing on complementary services like Jetpack that worked with all hosts.

As of 2017, Automattic had raised approximately $350 million total across primary and secondary rounds, with the last major round in 2014 raising $160 million. Matt was clear that this capital was raised specifically to stay private, not to pursue an IPO, believing that independence provided the flexibility needed to make long-term strategic bets that public market pressure would discourage. The company had surpassed $100 million in ARR and was generating revenues in the "nine figures" range. In 2015, Automattic acquired WooCommerce for $30 million, recognizing it as both a technology and product fit for the ecosystem.

Matt also launched Project Gutenberg while serving as CEO—a major reimagining of WordPress's core editor to use block-based editing (like Lego blocks) instead of traditional text-based editing. He took on a board position at GitLab, another fully distributed open-source company, continuing his investment in supporting distributed organizations. Matt made early crypto bets in 2013 through Audrey Capital, investing in Bitcoin and supporting WordPress's early adoption of Bitcoin payments, though he later sold most of his holdings.