Perhaps I'm not being clear. The new version of the MC blew his money on a crypto scam, and was so traumatized that he spent the next ten years taking absolutely no chances whatsoever. This means that in the intervening time he has had exactly zero opportunities to improve his basic judgement or his tolerance for risk. Yet the instant he makes a fortune selling his old KobaltKoins, he's not only willing to make rapid fire risky decisions (hiring a financial advisor, investing in real estate, hiring a lawyer), but based on the way the original game played out he's done a pretty shrewd job on all of them (though I suppose he did decide to ghost Nicki, so that does break up the streak a bit).
Given the way the game had gone to that point I'd find either of those outcomes unexpected on their own, but both together just seems out of character for the MC as he was (re)established. Remember, we didn't see a montage of the MC making some sound decisions prior to his drunken YOLO investment. We opened with him making one of the stupidest decisions possible, then watched him refuse to learn any useful lessons from as he writhed around for a decade.
The only thing this MC is demonstrably good at is fucking up. If he struck it rich, I'd expect him to either stuff the money under his mattress and be paralyzed by indecision, or decide he's bulletproof after all and go right back to making poorly thought out spending decisions. We know he didn't hoard the money, so that means he's back to being a high roller... and thus an industrial-strength scam magnet.
I know that's not what happens because I played the original version, but that MC had a lot more leeway to exercise good judgement either before or after the fateful incident. The remake spends more time fleshing out his actions but they're all terrible. Hence my assertion that if he came into money, I'd expect him to lose it rapidly.