As in, it's hard to "get ahead" by definition. So anyone that's overtly ahead of the pack has therefore been vetted as superior to most everyone else. It's a reasonable proxy for gauging intelligence, charisma, and interpersonal skills without even meeting them.
As you get more information you'd realize he made his millions making, say, a software product so, fine, that lowers the assumption of interpersonal skills and charisma and increases it of intelligence. Regardless, the shorthand implies an excess compared to average.
TL;DR - Arguably, "successful" is a rational and effective way to gauge a mate's value.