Gruber thinks in terms of brands. Apple is a brand. Reddit is a brand. Twitter is a brand. It's easy to pick winners and losers with brands.
Mastodon isn't a brand so much as it's a grouping of a bunch of different brands (servers). In a way Mastodon can't win or lose because of this. If you have 10 people on a server and they're happy- you've won.
Gruber has a hard time wrapping his head around this, partially because it's just not his thing.