What an excellent discussion, and I look forward to listening to the interview when I have a few moments.
There has been a lot of discussion about the DMs Guild. Given my history with the platform, I have thoughts. Mike Shea and I have discussed this endlessly in other forums.
For an aspiring game designer, I think the DMs Guild makes for a good breakfast, an indifferent lunch, and a miserable dinner. That is, it's a good place to make a start, but you need to move on pretty soon. Quite a few people now working fulltime in the industry honed their craft on the DMs Guild in the early days: Justice Arman, James Introcaso, Hannah Rose, Emmet Byrne, Celeste Conowitch, Joe Rasso, Lysa Penrose, come to mind. Countless others have picked up freelance writing gigs with first tier RPG companies.
Mike highlighted two big complaints with the Guild, and I agree they are problems.
The first is the 50% cut, which is very rough. I think it's wrong to compare this to a bricks and mortar store taking 60%, since they are providing things like physical shelf-space. The better comparison is other digital marketplaces (like the Apple app store), which typically take about 30% of the sale. The real reason the cut on the DMs Guild is 50% is because the hosting company (Roll20) takes 30% and WOTC takes 20%. If WOTC open their own marketplace in the future, such as on D&D Beyond or on their long-awaited VTT, I hope and suspect they will take 30%.
The other issue is that your IP is locked onto the DMs Guild perpetually. This became a real problem once the industry shifted to crowdfunding as the main source of income. Everyone understands that you can't take something about Drizzt and publish that elsewhere - obviously! It would be good if there were more flexibility to use non-WOTC IP that you may have published there. For example, in a hypothetical book "Drizzt's Guide to the Underdark", you might have created a dozen new spells which have no relation to WOTC exclusive IP. But I understand the tightrope this would require from a legal perspective.