Yes Trump did make most of his money using borrowed funds and leverage. However, the lenders in that case have skin in the game and the debtors presumably exert some restraint on Trump. Trump did have his credit on the line as well as whatever personal assets he pledged. For every high profile bankruptcy there were likely many more in which everyone made out, otherwise no one would extend him any credit.

Bankruptcy laws add a lot of value to a functioning capitalism and debtor and obliger are both aware of the laws. Perhaps you don't agree with them or Trump abused them but that's a different story.

Trump was smart in that he likely structured his financial dealings in a way to limit his personal losses, but the banks knew they and Incorporated that into their offer.

But it's true that more recently he has been a celebrity and leased out his name. However, since his name is his primary asset, you can still say he has skin in the game.

Also I would add that Trump's celebrity is due to something in his control. Whether it's because he's a demogouge, visionary or marketer extrodinaire, he is successful on his merits. Taleb would probably contrast that to some academic on an unelected government panel somewhere due to personal connections

So I'm not criticizing Trump here per se (I mean I really dislike him, but that wasn't what I was getting at.) My point is more that this distinction between "skin in the game"/"no skin in the game" that Taleb portrays as binary is really quite murky, and people's perceptions of who's taking risks are affected by factors other than the truth. I agree that bankruptcy laws often add value, but that wasn't the point; they add value precisely because they reduce the "skin in the game" of the person going bankrupt, whereas Taleb had indicated that Trump had shown his risk-taking by losing his own money. And it's exactly this idea that leasing out one's name, putting one's reputation on the line, turning yourself into a celebrity could also be considered having "skin in the game" that makes this distinction murky: isn't that what Taleb's IYIs do? Aren't all columnists, academics, journalists and so on playing in the same system, and self-promoting as a form of hustling their way to the top? It depends more on your perspective than on any objective definition of "skin in the game."

Also with respect to Trump being "successful on his merits"... being born into hundreds of millions is better than most connections. More importantly, Taleb isn't talking about success/failure on one's own merits, but taking on risk, and I think that's one of his better points. That's the difference between the "skin in the game" concept and judging based on some abstract idea of meritocracy: people understand that Trump was given advantages in his life, but they respect him because (they perceive!) he's opened himself up to risk and put those earnings, unfairly gotten as they may be, on the line.

I'm sure Nasim is talking about perception and not 'reality.' As the saying goes "perception is reality," I think you'll find that objective reality is not very important in the domain of culture.

> see Ross Douthat's career

Anything specifically that one should see or do you just not like him or his writing?

This is unfair of me; there are lots of pundits as bad as him or worse, but he's become the designated punching-bag on parts of the internet of people who thought Trump would never make it. Throughout the primaries, he was incredibly dismissive towards anyone who thought Trump had a chance, mocked the idiots who didn't see the obvious truth that Marco Rubio would win every primary, responded to every Trump dip in the polls with "I TOLD YOU SO I TOLD YOU SO I TOLD YOU SO YOU DIDN'T BELIEVE ME," then predicted that Rubio and Cruz would never endorse Trump, then predicted someone else would snatch the nomination at a contested convention... and still has a job for the New York Times, educating the masses on what the future holds. No punishment for being wrong: no skin in the game.