Will was working for a publisher (not sure if it was the same his dad worked for), before they started Chapo. He had the roledex of authors and media connections that let him get some big early guests. He also seemed to be the one bankrolling and doing the business/legal stuff for the podcast. At one point Chapo, or Will personally, was sued by someone. They never mentioned it on the podcast until the case was over and Will won. It was probably libel/defamation since they used to end the show by threatening violence to various political and media figures.

As for takesmithing, Will just grabs stuff from Twitter. There was a time when, if you followed all the Chapos and people they follow, you could see the weekly episode content in their likes/posts/replies. He just cribs other people's takes. It's smart because it's very hard to have great takes all the time and using twitter to essentially crowd source it saves time and probably helps generate better ideas. But the downside is that Will sometimes straight up plagiarizes shit off the internet like it's his own idea. I've even seen him repeat stuff we all concluded here on this site because the internet moves faster than a bi-weekly podcast recording. Not saying that he browses here, just that the online left space is insular enough that takes get around pretty quickly and easily. And it's also important to note what the Chapos do isn't particularly difficult or unique. It's mostly being well-read and paying attention to stuff.