You do know how he started in Canada right ? Nothing glamorous about that. And don't get me started on the Emerald mine talking point. As far as every trustworthy source has confirmed he was quite far from a trust fund kid. The one thing in his favor was possible to be a white, well educated kid. Compared to all the PoC who don't even have that under similar conditions.
Its still a good skill picking winner in a hyper competitive environment, but he's closer to an average trust fund kid than a jobs or a page.