WordPress co-founder and Automattic CEO Matt Mullenweg didn’t mince words: buying Tumblr is the biggest failure of his career so far. But he’s not walking away. Speaking at a Town Hall during WordCamp Canada 2025, Mullenweg laid out why the turnaround has been so hard, what comes next, and how the broader WordPress ecosystem is evolving.
At the heart of the challenge is technology and scale. Tumblr still runs on a different stack than WordPress, despite long-standing plans to migrate its back end to WordPress infrastructure. That move would streamline maintenance, reduce costs, and better connect Tumblr to the open social web, including the fediverse. But the effort is massive and expensive. With more than 500 million blogs to move, and with Tumblr still unprofitable and subsidized by Automattic’s other products, the migration was put on hold earlier this year.
“I need to switch [Tumblr] over to WordPress, but it’s a big lift. It’s over 500 million blogs, actually, and, as a business, it’s costing so much more to run than it generates in revenue,” Mullenweg said. Automattic has reduced costs through layoffs and by shifting Tumblr resources toward more profitable projects, but those changes haven’t yet delivered the turnaround needed to resume the migration at full speed. “It’s probably my biggest failure or missed opportunity right now, but we’re still working on it,” he added.
Even with the pause, the vision remains the same: get Tumblr onto WordPress infrastructure to make it simpler, more cost-effective, and more interoperable with the open social web. That alignment would also make it easier for Tumblr to participate in federated networks, a direction Automattic has increasingly supported.
Beyond Tumblr, Mullenweg highlighted several initiatives across Automattic’s portfolio. He called out ongoing work in WordPress, Jetpack, and WooCommerce, and spotlighted Playground, a tool that runs WordPress entirely in a web browser. He also discussed Beeper, Automattic’s universal messaging app, which will expand with new bridges to additional services, including KakaoTalk and messaging features from dating apps. The goal is to knit together more of the fragmented messaging landscape, giving users a single place to manage conversations across platforms.
On artificial intelligence, Mullenweg was pragmatic. He noted that “we’re not putting the genie back in the bottle,” and described leading AI companies as “too big to fail.” Rather than rejecting AI outright, he suggested practical ways to adapt. One example under consideration is tagging AI-generated images in the WordPress theme directory so users can filter search results to match their preferences, instead of banning AI-created themes altogether.
The session also touched on tensions within the WordPress ecosystem, including a legal dispute involving WP Engine, a hosting provider that Automattic has criticized for benefiting from open source without contributing proportionally. Asked about “bad actors,” Mullenweg reframed the issue as “bad actions” and emphasized creating incentives that reward positive contributions. He floated ideas like boosting visibility for contributors in the WordPress directory and showcase, and urged the community to “vote with your wallet” by supporting companies that give back.
Mullenweg referenced a site that tracks the number of websites leaving a particular host, noting it was nearing 100,000 tracked moves, with tens of thousands of sites going offline since last September. He said the site was temporarily ordered offline by the courts, calling that action an attempt to muzzle free speech and transparency.
For now, Automattic’s path forward centers on making Tumblr sustainable and aligning it more closely with WordPress’s technical foundation. If and when the migration resumes, Tumblr could gain the operational efficiency and open web compatibility Mullenweg has long envisioned. Until then, Automattic is focusing on projects with clearer returns—while still keeping the Tumblr turnaround on the table.
