In short: The Volmageddon trade with Peter Thiel: "we had pre-positioned and pre-announced our expectation that the XIV ETF would collapse to zero… in a single day as it did on February 5th, 2018" — possible because product and underlying were the same thing.
XIV was a popular note that paid off when stock-market volatility stayed calm. It was so large that its own required trades moved the volatility futures it tracked — the product and its underlying were effectively the same thing. Green and Peter Thiel publicly predicted it could go to zero in a single day, and it did on February 5, 2018 ("Volmageddon"); it was then shut down.
He mentions it as the trade that made his name — and that also misled him, because broad index funds like the S&P 500 ETFs don't work that simply. It is history, not something you can buy.
18:44Now part of that was also a function of I had not yet cracked through the code of what exactly was happening in terms of how the indices were playing out and what were the parts that become predictive. It turns out that the success that I had around Volmageddon with Peter Thiel where we had pre-positioned and pre-announced our expectation that the XIV ETF would collapse to zero in a single day as it did on February 5th, 2018.
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Verbatim excerpts from the public transcripts (auto-pulled at each mention's timestamp, lightly cleaned). Timestamps link into the video; "source page" opens that commentator's full analysis at this row. Click a mention's header line to expand it (one open at a time). For personal study — not investment advice.