After he sold to NameMedia, of which he still owns a 15 percent stake, Mann had a noncompete that kept him away from the domain game for about four years. Instead, he worked on his many other ventures, such as SEO.com and a nonprofit called Grassroots.org.
From grassroots.org:
The mission of Grassroots.org is to help charities succeed by providing them with modern technologies and best practices at no cost.
I don't know if it's morally correct or not, but Mann doesn't otherwise seem like a morally bankrupt individual.
Grassroots.org appears to just be away for him to funnel more cash to himself. The charity gives away his SEO services - i.e. donors are just paying for his salary.
It's not amoral. I've been frustrated myself over domains I couldn't get, but I fail to understand how this is amoral. Too often we are quick to make moral judgments based on distaste (of which I share).
Why is it not morally correct? He is just speculating as speculators do in all different industries. And kudos to him - it's technically non-trivial, carries a lot of risk and clearly requires a lot of business acumen to work.
From grassroots.org:
The mission of Grassroots.org is to help charities succeed by providing them with modern technologies and best practices at no cost.
I don't know if it's morally correct or not, but Mann doesn't otherwise seem like a morally bankrupt individual.