As a relative outsider, I would hope being labeled as one of the biggest failures would be a mark of experience among a set that claims or claimed to uphold the “fail fast” mentality and treats failure like the learning experience it is.
In Walk Street if you have a $50 million blow-up your career is shot. If you have a $500 million blowup you get a second shot because you must have been somebody to be trusted with that much money.