I think he lays it out pretty well: earnestness is more than sincerity, it's dedication to solving a problem for its own sake rather than as a means to an end. I'm not sure why you want that to be quantifiable, but I don't see that as being useful since Goodhart's law then kicks in.
I do agree that on a single continuum from roulette to race, entrepreneurship is closer to roulette, but it's a limited framing because entrepreneurship is neither a well-defined rote exercise like a marathon nor a discrete probabilistic event like flipping a coin. To the contrary, building a company is a continuous feedback loop involving thousands of decisions over which an entrepreneur has complete agency. The uncomfortable truth is twofold: founders' choices do affect outcomes, but those outcomes are not predictable and have no direct relationship to ones own perception of merit, hard work, fairness, or morals. Getting hung up on the luck aspect and whether or not some successful person is humble enough is a defense mechanism that ultimately gets in the way of maximizing your own success.