[10] He attended the High School for the Performing and Visual Arts to play the saxophone,[11] although he was frequently absent due to chronic migraines.

After graduating from high school, he studied economics, philosophy and political science at the University of Houston, eventually dropping out after his sophomore year in 2004.

He has stated that he prefers to settle disputes in the court of public opinion and described his approach as "brinksmanship", noting that the potential cost of legal action could put Automattic in a "tough spot".

Despite the license's requirement to publish anything built with GPL code under the GPL, Wix's CEO claimed that the company open-sourced their forked version of the component and satisfied the license's terms[35][36] before the app switched to its own fork of the MIT-licensed text editor that the WordPress editor was based upon.

[38] On January 9, 2025, the representative of the WordPress Sustainability team, Thijs Buijs, resigned via WordPress.org’s Slack channel, citing dissatisfaction with Matt Mullenweg’s December 24, 2024, Reddit post titled “What drama should I create in 2025?” highlighting concerns about what he described as “unsustainable leadership”.

[41] In response, WP Engine issued a cease and desist against what it characterized as defamation and extortion, attributing his attacks to WP Engine's refusal to pay Automattic "a significant percentage of its gross revenues – tens of millions of dollars in fact – on an ongoing basis" for what it claimed were necessary trademark licensing fees (later clarified as 8% of all revenue, payable in gross or in salaries for its own employees working under WordPress.org's direction, combined with a clause that would've prohibited forking[42]) for the "WordPress" name.

[42] As a result of the dispute, WordPress.org blocked WP Engine and affiliates from accessing its servers—which include security updates, the plugin and theme repository, and more—on September 25, 2024.

[46] Following backlash, access to WordPress.org was temporarily restored until October 1 to allow WP Engine to build its own mirror sites two days later,[47][48] which the company did.

[49] On October 7, 2024, to align the company's stance, Mullenweg announced that 159 employees—8.4% of Automattic—had quit in exchange for a severance package of $30,000 or six months of salary, whichever is higher, with the condition that the resigned would not be able to return.

[50] The next week concluded another offer of nine months' salary to attempt to placate those who could not quit for financial reasons,[51] though with only four hours to respond and the added term of being excluded from the WordPress.org community.

It has also funded startups that provide services to web developers including Creative Market, GitLab, NPM, SendGrid, Stripe and Typekit.

[55][56] On the 20th anniversary of WordPress' initial release, Mullenweg announced a scholarship program aimed at the children of significant contributors to open-source projects.