I don’t think Matt would have been willing to have this kind of conversation with me or most members from the the general community

I enjoyed talking with Matt Medeiros on his podcast a few years ago, including about some of the same topics: https://mattreport.com/interview-matt-mullenweg/

Which came from a WP Tavern article around the same time: https://wptavern.com/how-important-is-jetpack-on-wordpress-road-to-50-market-share

I'm happy to chat with community members around these conversations and I'll be going on a number of community podcasts the next few months including ones with only a few hundred listeners. I don't see any emails or .org Slack messages from Medeiros but if he reached out would be happy to schedule some time, as I have in the past. :)