Taleb is not a source of investing advice at all - he merely illustrates his philosophy with examples from finance as it's something he's more than familiar with.

Stock market is a fool's game by its nature.

I'll rephrase for hassy. "investing" is for suckers. the only people making any money in the market are professional traders who aren't at all making decisions based on "trends" or "fundamentals".

see: dynamic hedging by nasim taleb--a book that sits on many professional traders desks in which taleb makes more than a few points about trading.

> I continually hear stories (friends of friends, of course) of people hitting it big and wonder if I just don't get it.

For every hitting it big, there is an opposite (and often larger) story of losing it big. Often by the same people -- except they are happy to tell you about their wins and don't talk so much about the losses.

It's not even a zero sum game -- the fees and spreads ("friction") are non-trivial.

Selection bias. You'll only see news about the extremes. You'll never see news about the average person who loses money or makes less than the market.

I'll worry about it when I have it. But my current thinking is along the lines of: 10-20% in highly speculative stuff (much more so than stocks) and the rest in super-safe stuff (much safer than stocks).