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Mike Sinclair is the best and funniest story teller in the skate industry. Bill Weiss close second.
Mikes story about the "Gentry Rule" cracks me up every time:
Mike is the only skate industry person that leaps out to me as someone I’d like to have a beer with. I’m sure there are others, but he just seems cool as shit.
Hey Mike Sinclair was pro for the bad Zorlac so he doesn't count here!

But truths, Sinclair rules. Dudes a true fan of skateboarding and skateboarders and funny af.
Bobshirt has a deep knowledge and is a treasure trove of skate history, just check his channel.
https://www.youtube.com/@Bobshirt/videos or this Skatehoarders episode:
For written content, Chrome Ball Incident is the best par none.
If you want to watch different type of content, check out Skateboard Ranch -series. An Canadian skater named Sebastian who want's to build a place to skate in somewhere north of Quebec and starts by buying a property in the middle of nowhere and documents the whole process. What follow is a true DIY endeavor where one problem creates 15 new ones to be solved.
Skateboard Ranch: