Agreed. Only at the very end of the right column which most users will not read to is the mention of the charge. "Activating your VIP service" could easily be interpreted as being free given the purchase. Regardless of their numbers, it is definitely not obvious that there will be a monthly $40 charge. (The fact that they do give a credit for the charge makes things not 100% scummy I will say)

Second that. Smallest font on the page, light grey while everything else is black, pushed to the bottom of the side column - certainly looks like fine print to me.

There's no option to opt out of VIP membership - if I haven't said I want it, and was not asked whether I want it, I shouldn't be paying for it, should I?

I think OP has a case here.

Do they ever try to remind customer about the upcoming charge?

I don't accept the word "misleading" -- I do not believe the page in any way misleads. It does not try to position it as anything other than a subscription, and the language is plain english.

Could they put the subscription details in bold? Could they use a larger font than all the other text? Sure. It's a tradeoff, for sure, and every retailer has to optimize their site to perform. Could they pop up three boxes after you click yes and say, "Are you sure?" "Are you really, really sure?" -- (yes, I know I'm being ridiculous) -- but yes, it is a tradeoff.

But with an NPS score in the 50's, nearing a million subscribers with very low churn rates -- happy users -- as investors we feel the business is healthy and being managed in an upfront way.

But, I can see how one might feel they would like it bolder or more prominent -- reasonable people could disagree on that.

I would submit that, when you come to view the site under the lens of clicking on a discussion about a fraud, and then go to it to decide if it is a fraud, and you (probably) aren't a likely customer and don't think "damn, that's a hot pair of boots for $40", you end up with a different lens.