I don’t doubt these anecdotes that show the guy’s intuition was correct in a few cases. I’d be interested to know when it was wrong.
For example, he had an intuition that his engineers could build full self driving in 12 months 10 years ago. And every 12 months he’d show up promising that it would be ready for real for real in 12 months. Nah bro, he was just lying to pump up the stock price. Yeah, maybe. Or his intuition was just wrong.
He’s exceptionally good at taking credit for work done by others. SpaceX is the classic example, but him playing Path of Exile claiming to have reached the maximum level possible when actually he was taking credit for someone else playing on his behalf is another good example.
This is a really useless statistic. How many times was Musk wrong and his engineers were right? We don't know, we only have those two hand-picked examples from a less than neutral source.
For example, engineers also warned the launch pad wasn't suitable for the first test flight, those enineers were correct, it didn't matter as much as it would have for e.g. a Saturn V or a Space Shuttle launch because Starship was (and still is) a test flight of a shockingly cheap unmanned vehicle.
That said, if the people currently raising alarm over Kessler cascade risks are correct, that would be an example of something essentially unsurvivable for Starlink and similar constellations.
Musk gambles when he thinks the expected return is positive; you can do that while winning hardly any bets, let alone loosing hardly any. What you have to avoid fooling yourself over are the odds, the costs, and the rewards, and I do think Musk is fooling himself about political costs if nothing else.