I believe Gumroad uses Stripe to process payments, so I'd guess this entire validation process is coming from Stripe. When the CEO paid you via Zelle, he probably just wanted to help you out with the hope that you would continue using Gumroad and have a positive experience with the company. I wouldn't look at any of this as a negative reflection of the company.
(I've personally never used Gumroad, so this opinion is only based on your comment and my experience with Stripe)
That could be the case but Gumroad knows the requirements to become verified.
Gumroad chose to gather the minimum amount of info and requested more with dark pattern forms to maximize collecting personal information without providing value.
If they said up front everything that was needed and it was a requirement of their payment processor then it would have cleared everything up.
