Taleb being an academic is fun to read. He's an options trader. He made his money with a fund that bought way-out-of-the-money options. That strategy loses money most years, but was a big win in 2008, when the crash made those cheap options valuable. Any 5-year period in the past 30 years that didn't include 2008 would probably have been a lose. So he may have been lucky, rather than smart. Although, arguably, you could see in the runup to 2008 that something had to give.

Taleb's big argument here is that Bitcoin will someday be obsolete and will have a value of 0. Since Bitcoin doesn't generate income or pay dividends, its present value is thus 0. That's a strange position for an options trader to take. Options, by their nature, expire, and have a value of 0 at some future time. Yet they are traded during their life as having value.

An option is a bet, not an investment. It's zero-sum; losers + winners is zero, minus some trading costs. This is also true of Bitcoin. Taleb, interestingly, does not analyze Bitcoin as an option. Possibly out of frustration. Options are analyzed based on what the underlying commodity is expected to do. Bitcoin has no underlying commodity. So option analysis techniques won't work.

Nobody has a convincing model for the future value of cryptocurrencies. It's mostly velocity investing - it goes up because it's been seen to go up. Until it doesn't. Taleb looks at financial history, sees that this isn't the first thing which behaves that way, and notes that pure speculative instruments always collapse in the end. But when?