There's not really any good reason to compare Freedumb to Bianca Chandon. The only thing I see in common with them is that skaters own them.
It's not a true comparison, it's more-so a subtle point. Being that Freedumb is classic, honest to skateboarding and has a team of all of his homies that are legendary to skateboarding.
Does Bianca truly represent skateboarding in an honest way or a pretentious way? IMO, it's pretentious. Sure, he wants to be artistic and voice his opinions, I just think it can be in so many different ways that aren't so exclusive to just Alex Olson's interests but inclusive to skateboarding and embraces it as a community.
It doesn't seem AO knows how to connect the essence of skateboarding with his interests yet.....as I mentioned before he should consider freelance illustrators/designers for board graphics. It's always good to have an open ended art direction. Classic is the way to go.
I'm sure I will be proven wrong and his products will be worth money one day and auctioned off on eBay for crazy prices.