There is a serious disconnect between the mc's actions and his backstory. He was a very rich thrill seeker in his first life, yet the character seems to lack business sense and basic planning while also being rattled too easily. It makes the character, even though we don't know him that well, feel like he has regressed. His arc should be more overconfident at the start before becoming more cautious over time as character growth. Instead, he comes off almost timid much of the time. I think that this issue could be salvaged if you made him have nightmares about his death, etc, to give a reason for him being so low-key out the gate.
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LIKEHe can't exactly do the same things that resulted in his death now, can he? You gotta look at things from a different point of view. He is in the body of a 19-year-old. While he is still him, he has a different set of responsibilities now and his body is obviously emotionally attached to his little sister. Any action he takes, he has to consider her... not just himself. If it was just him alone, he'd still do things with reckless abandon. As for the business, he already successfully created one that is doing well, so what exactly is the issue?