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.

Just finished listening in to this episode – loved seeing the humility, generosity, and passion of open source reflected in the formation of Automattic and the company culture as it exists today.
I just started using Pocket Casts yesterday. So far I really like the interface. It seems to be a really good app. I also like the thought of using something different and fresh compared to the oligopolistic companies dominating the market.
Condolences.
Hi Matt. Congratulations on the success of Automattic and WordPress.com after all these moments. I have one question. What happened to the latest WordPress.com pricing? I love WordPress.com and would be heartbroken that I’m currently on Premium and can’t continue on WordPress.com because I can’t afford to pay if I have to upgrade to Pro.
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, WordPress.com has always been the best for me and I always hope that the great quality will continue to be maintained.
Matt,
I’ve followed you since your early days of WordPress. I am thankful that you went on Guy’s podcast as I was able to learn all the behind-the-scenes things that you did to get WordPress to where it is today. I grew up in Houston as well and that was really cool to know that is where you began your love for coding. You are correct in how masterfully they edited the podcast, it flowed very well, and knowing that you did a four-hour chat and it was shortened to one hour is impressive. Keep up the great work!
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. (https://blog.mixcloud.com/2021/06/30/why-mixcloud-doesnt-offer-on-demand-video-vods/)
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.
WP-4-Life!
Going to enjoy listening to this one Matt!