I don't think this guy was being an asshole for offering advice when people sought him out as an expert. Perhaps he is being more tactful with his new approach, but he definitely wasn't being an asshole imo.
Though I agree, I think many people mistakenly interpret direct suggestions as being commentary on the junior-person/company Y's flaws and might be seen as more aggressive (asshole-ish)than having a senior-person/company X point out their own flaws. That makes X seem more humble, and more importantly, depicts success in the face of struggle as more attainable. I really think that's what provides the most benefit from his new approach; successful person/company X is not some mysterious deity that simply exists, it is the product of actions taken throughout the same process junior person/company Y has recently faced, is facing, or will face. Junior person/company Y may make, or have already made, different decisions or actions at various steps and, for better or worse, will be different because of it.