Those things are possible (in a limited way), but a big bucket of money doesn't make you better at it, which is the context here. Checking with another expert

Those things are possible (in a limited way), but a big bucket of money doesn't make you better at it, which is the context here. Checking with another expert is just the same problem with extra steps. It's very common that someone has a stunning reputation and after a few minutes of chatting with them you realize they are a fraud (if you have expertise in the thing you are talking about). So the CEO's 'technical friend' is as likely to be a fraud as not, if not more likely as frauds are very likely to cluster around people who are making decisions that could lead to checks being written, and CEO's are much more likely to be sales-focused extroverts and we are all biased towards trusting people like ourselves (and an extroverted salesperson has a ton of overlap in terms list of characteristics with a con man). I've been in this industry a long time, I have seen plenty of 'technical leaders' who were complete and total charlatans, up to the point where their resume was very obviously fabricated (companies that never existed, job roles that never existed, the websites for the companies on their resume being fake and obviously created by them). It didn't seem to harm their career much if at all, and their bosses never once caught them out for their incompetence, even after years.