Yours Truly on Crossword, With Jonathan Wold and Luke Carbis

Jonathan Wold and Luke Carbis cohost a podcast called Crossword, focusing mainly on WordPress and the open web. They occasionally invite guests to join them, and it was my pleasure to join them on their latest episode:

John Gruber’s Dithering podcast with Ben Thompson was the original inspiration for Crossword’s 15-minute format. Five years later, John joins Luke and Jonathan for a wide-ranging conversation covering open versus closed platforms, the history and impact of Markdown, and a missed opportunity in WordPress. Luke goes on about the good old days, Jonathan starts thinking about a rival platform, and John makes a prediction for the ten-year follow-up episode.

While their usual format is a Dithering-esque 15 minutes, these special “perspectives” interviews run long. And unsurprisingly, mine ran long. I don’t write about the open web as much as I used to but I care about it as much as ever. I express some of my deep concerns about Substack in particular in this interview.

★ Thursday, 10 July 2025