After years of losses that almost nobody else would have been able (or willing) to sustain he made it into a moderate success.
Outwardly, at face value, he's doing pretty well, until you count the decade of losses which nobody talks about.
Another friend is a moderately renowned documentary maker. Again, facilitated by family wealth. Outwardly, the appearance is of being successful, which cost a fair chunk of family wealth.
I think in both cases, family wealth drove something akin to an obsession to appear successful, which they largely achieved and nobody mentions the uncomfortable facts about how they got there in polite company.
Almost nobody else would have been able (or willing) to sustain the costs that made it into a success.
What matters is the bottom line.
With more money can of course learn to fail in greater scale, but IMHO this also has benefits in it's own. Learning to think big is a skill of it's own. Small business plays by different rules than big business, even if they have overlaps.
And I also think how succesfull you really were can only be said after staying on your peak for some time, because some games go really really long.
[0] https://digitalsynopsis.com/inspiration/privileged-kids-on-a...