Occasionally, riders make the brand legit, rather than vice versa. I am not a fan of the names or aesthetics of Straye or Raw Dawg personally, but I don't know that they aren't going to end up being successful, especially with people like Antuwan involved. After all, the big name brands are dwindling in popularity and impact, so other brands are going to have to come up in their place.
Unless skateboarding is dying again, in which case it might be that nothing replaces them, but that's a different conversation altogether.
Also, I'd also like to say that the phrase "Black Tom Penny", regardless of where it came from, is bad. 'The Black (insert white person's name here)' is a phrase that should have never come to be, and should definitely be retired permanently.