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Automattic CEO Calls Tumblr His 'Biggest Failure' So Far (techcrunch.com) 28

An anonymous reader quotes a report from TechCrunch: WordPress co-founder and Automattic CEO Matt Mullenweg called the company's Tumblr acquisition his biggest failure -- but one he hasn't given up on yet. The comments were made at the recent WordCamp Canada 2025 conference, where Mullenweg went live for a Town Hall session to connect with the open source-focused WordPress community.

The exec noted that Tumblr was still on a different technical stack than WordPress -- something he had intended to correct by migrating the back end to WordPress infrastructure. However, that massive undertaking was put on hold earlier this year, as the cost to move Tumblr's half-billion blogs would be difficult given that the blogging platform wasn't profitable and continues to be sustained by the profits of other Automattic products.

The company has tried to trim costs with layoffs and the reallocation of Tumblr resources to more profitable parts of the business, but those efforts have yet to pay off. Mullenweg acknowledged these concerns at his Town Hall session, saying, "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." As a result, Automattic had to prioritize other projects to make Tumblr sustainable, he said. "It's probably my biggest failure or missed opportunity right now, but we're still working on it," he added.

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Automattic CEO Calls Tumblr His 'Biggest Failure' So Far

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  • WP Engine Lawsuit (Score:5, Insightful)

    by NaCh0 ( 6124 ) on Tuesday October 21, 2025 @11:37PM (#65742074) Homepage

    It's pretty crazy to say that Mullenweg's biggest failure isn't his flipout at WPEngine, getting himself sued and losing the trust of the entire wordpress community who isn't somehow on his payroll.

    That whole login checkbox thing on wordpress dot com accounts was the final straw for many supporters of his.

    • by Dracos ( 107777 )

      His biggest failure is never (after 21 years) learning how to write PHP, design a database schema, or learn about application architecture.

      Exhibit A: the WordPress codebase.

    • by Kisai ( 213879 )

      Wordpress sucks. A LOT. Migrating Tumblr to Wordpress would be like trying to run a diesel train on a gasoline boat engine.

      No serious company would ever run their business on Wordpress, and no serious company would run their entire goddamn business on the AWS stack. I swear to god businesses would rather lose business to hours and days of downtime than just hire one guy to maintain their own shit.

      • It's managerialism. Much better to be the "no one was ever fired for choosing IBM"-guy than the "You supervise the employee that does a job you don't understand"-guy.
    • It's hard to take someone seriously when they think the solution for Tumbler's problems is to convert it to Wordpress.
  • only with less money and even less charisma
  • Well... (Score:5, Funny)

    by LordHighExecutioner ( 4245243 ) on Wednesday October 22, 2025 @01:00AM (#65742140)
    ...a Manual CEO could have succeeded, maybe.
    • ...a Manual CEO could have succeeded, maybe.

      I know AI is supposed to destroy all the jobs, but it seems to be moving up the org chart faster than expected.

  • by fishnuts ( 414425 ) <fishnuts@arpa.org> on Wednesday October 22, 2025 @01:25AM (#65742160) Homepage

    Tumblr COULD HAVE been profitable, but the decision to block/prohibit adult content completely, rather than segregate it behind a "18 and up" requirement and monetized it, killed any chance of that.

    • by nicc777 ( 614519 )
      It feels like everyone just moved to reddit after that. And look where they are now.
      • Reddit is also coming under fire. The great "Rule 1" - Be Human. Don't post content marginalising vulnerable groups. There's plenty of adult subs getting shut down daily because of this.

        • by nicc777 ( 614519 )
          Agreed - I was referring to that period of time when tumblr made that decision. Reddit was an easy alternative. I would say since the last year or so reddit is also getting worse day-by-day (my personal experience). AI slop is infiltrating everywhere.
        • by xevioso ( 598654 )

          UH... humanity *is* about marginalizing other groups. The entire history of humanity revolves around doing just this.

          • UH... humanity *is* about marginalizing other groups. The entire history of humanity revolves around doing just this.

            Uh no, that's civilization. Humanity is about caring for the 10 members of your tribe, who also happens to be close family members.

            That's how it was for the large majority of time for the human kind; having enough people to be able to marginalize some of them only came about after the invention of agriculture, where groups settled and started to grow large and have different income levels.

    • Tumblr COULD HAVE been profitable, but the decision to block/prohibit adult content completely, rather than segregate it behind a "18 and up" requirement and monetized it, killed any chance of that.

      They rolled that back partially years ago. Tumblr is full of adult content again. But from what I gather they are completely arse about in how they apply it. No sex. Oh but depictions of BDSM are okay so are depictions of abuse, just make sure no sausage enters a bun.

      • Tumblr COULD HAVE been profitable, but the decision to block/prohibit adult content completely, rather than segregate it behind a "18 and up" requirement and monetized it, killed any chance of that.

        They rolled that back partially years ago. Tumblr is full of adult content again. But from what I gather they are completely arse about in how they apply it. No sex. Oh but depictions of BDSM are okay so are depictions of abuse, just make sure no sausage enters a bun.

        I was wondering why my gourmet hot dog photos were getting taken down.

    • by tlhIngan ( 30335 )

      Tumblr COULD HAVE been profitable, but the decision to block/prohibit adult content completely, rather than segregate it behind a "18 and up" requirement and monetized it, killed any chance of that.

      The problem was Tumblr wanted an app. If you have an "18+" section, Apple requires your app be marked 18+. Apple's reviewers at the time rejected the app because it was marked teens+ or for all ages, and Apple could easily find 18+ content. Apple even suggested they just rate the app 18+ like other similar social

  • by Tillmann ( 859300 ) on Wednesday October 22, 2025 @01:52AM (#65742168)

    Tumblr failed not because of the tech stack, but because of content policies that drove creators away. It could have become a highly profitable platform, like OnlyFans is today - but instead, they chose to deny this business model. It's really bizarre - kind of like running an Online Casino that doesn't allow gambling, and then blaming the failure on the tech stack.

  • Is he saying his biggest failure ISN'T creating the tooling that has seen the web flooded with infected, garbage, sites?

    That's an interesting take

  • Apart from Gutenberg, he neglected to confront some historical debt.
  • by ledow ( 319597 )

    I mean... I know Tumblr went downhill and I abandoned it several years ago, just after it was taken over, but I wasn't really paying attention as to why.

    But I never imagined for a second that the plan was to convert the entire thing to Wordpress...

  • by geekmux ( 1040042 ) on Wednesday October 22, 2025 @03:47AM (#65742264)

    Bought a web service that infamously banned pornography after establishing the premise that pornography could have been the main reason they were ever profitable or popular?

    Not even Elon was that fucking stupid.

    We can teach our kids about morals all day every day. Doesn’t change the fact that porn built the internet. Porn bans, are profit bans. Plain and simple. Banning profit isn’t the problem. Not charging anything for your damn product, is.

  • by bsdetector101 ( 6345122 ) on Wednesday October 22, 2025 @06:54AM (#65742434)
    You better have a good doable plan in place BEFORE you buy out another company. Bought in 2019..6 years ago. WordPress.com parent company Automattic in a $3 million fire sale. Company troubles all around. Tumblr...something I have never used.

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