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Not so. Guy had ownership/controlling interest in 4 companies that filed for chapter 11 bankruptcy restructuring. Saying "he" went bankrupt is not accurate. I don't support the guy, and I think the fact that he is getting so much support is a very clear indication that we, as a country, are heading into troubled waters. But to say that "he" went bankrupt is inaccurate and irresponsible, because it implies a personal failure of finances, when what it really is is normal in the business world. Many businesspeople don't succeed on their first attempt, and the higher the possible gain, usually, the higher the risk of failure. The Paypal guy had several failed businesses prior to Paypal.
If anything, Trump's business history, including the four business ventures that ended in chapter 11, can be used as a model for young entrepreneurs about how venture capital/business start up/chapter 11/cycle works. Trump has a net worth of over 2 billion dollars. He got there by trying and failing and succeeding, and the people who financed him - and lost in the chapter 11s - clearly thought the guy had the ability to make them money, which he may have in his successful ventures.
This is an incredibly charitable gloss of Trump's business career and it's a bit strange to say that he provides a "model for young entrepreneurs." It was pretty well known that he himself was the guarantor on a significant portion of the financing for the Taj Mahal which is why he carried close to a billion dollars of (personal) obligations into the 90s. That was the deal where he got some schmuck analyst fired for predicting that the Taj would go under in its first year and then, lo and behold, bankruptcy for the holidays. He lost about $100M of his own money when the Hotel/Casino entity filed for BK about ten years ago.
If by the PayPal guy you mean Elon Musk, he sold his first company for $300M.