Guy Raz’s How I Built This

I spoke with Guy Raz about the early days of WordPress and Automattic on the latest episode of “How I Built This (listen on Pocket Casts).” We ended up talking for over four hours and the show has skillfully edited this down to just over an hour. We discussed my time at CNET, how I accidentally invented a new way to spam, why we didn’t sell Automattic, my feelings on Wix and competitors like Shopify (sponsor of this episode, hah, in which I speak about how their dashboard looks just like WordPress’s). Guy pivoted the conversation to grief that came with the loss of my father and challenges we faced during the pandemic. He kept the conversation going effortlessly and I had a great time taping the episode. Thanks to Guy and his team for a great experience. 

5 thoughts on “Guy Raz’s How I Built This

  1. Hi Matt. Congratulations on the success of Automattic and after all these moments. I have one question. What happened to the latest pricing? I love and would be heartbroken that I’m currently on Premium and can’t continue on because I can’t afford to pay if I have to upgrade to Pro.

    1. I want to update my comment. After I tried upgrading to Pro plan and comparing it with similar services, I can say that although the price is not really affordable enough for me (and maybe for some other users), I admit that the prices, specs, and supports are indeed competitive when I compare it with similar services (managed WordPress hosting). So far, has always been the best for me and I always hope that the great quality will continue to be maintained.

  2. If one could say that Tumblr is “Proudly powered by WordPress,” things could get even more interesting from a pr / marketing vantage point!

    Also, if DJs could perform live sets without fear of “takedowns” due to copyright violations, that would definitely be a game-changer. Twitch is very popular, but often mutes portions of a DJ’s set when one replays the set hours later. Mixcloud is the only legal option, but isn’t as popular. (

    By the way, Tumblr’s new homepage looks very cool! Going to sign-up.

    This is fun to run through the cycle: 5-3-b3-2-1.