To double back on the Spotify talk....
The fact that Joe didn't seem to understand why Spotify was against them either having no episodes or half assed episodes over the holidays speaks volumes about his mindset, and why he isn't where he thinks he should be in success.
Failure to understand, or at least see the bigger picture from multiple angles will always kneecap your earning potential. Joe was thinking about taking time off. Spotify was looking at that week span traditionally being a higher volume consumption period for all forms of media, and especially streaming audio services. Them either taking that time off, or coming with a half assed episode (which, let's be honest, is exactly what would've happened if they tried to pound out their normal schedule of episodes along with pre recording a couple of extras) wouldn't have worked out in the way they thought it would.
Also, Joe effectively engineered them offering the equivalent of a 360 deal by running the video version on YouTube. I think when they got the first deal done, either both sides underestimated how many people were willing to wait for video (or, probably more accurately, are already conditioned to using YouTube with its methods of monetizing viewers, over starting to deal with Spotify), or the pod's side of the negotiations willingly misrepresented the video audience. Either way, they had to know that Spotify wasn't going to be cool with leaving money on the table that's going to another direct competitor (don't forget YouTube Music is a thing, and gives the bonus of eliminating ads on YouTube). It also doesn't help their argument that The Pull Up is run on the same channel as the pod. Makes it easy for Spotify to argue that a considerable portion of the views for that show come from people who were originally there for the podcast they're supposedly paying to make exclusive.
What's baffling is that from the outside looking in, it seems like the easy answer was to counter with offering to move the video version of the pod to Spotify exclusively, and then give The Pull Up its own channel to fully separate the two. Then, even if it's a bullshyt deal, have any future promos of Dussrpalooza, or other projects appear to be paid. Their whole argument for getting into their pockets for everything else was that all those Ms Joe was bragging about seeing were promoted or set up on what was effectively company time, since they were paying for those episodes.
For a guy that essentially brags about never having had a real job, Joe is out here showing that he hasn't learned one of the most important lessons of being an employee: don't develop shyt that can be proven was done on the company's time, or the company's dime.