Barbell Investing

This is a thread to discuss Taleb's barbell investing idea, introduced in Chapter 13 of "The Black Swan."

I'm going to quote Taleb's description of the strategy here, which I believe is ok because he blatantly and purposefully makes all his books freely available via online pdf.

"If you know that you are vulnerable to prediction errors, and if you accept that most "risk measures" are flawed, because of the Black Swan, then your strategy is to be as hyperconservative
and hyperaggressive as you can be instead of being mildly aggressive or conservative. Instead of putting your money in "medium risk" investments (how do you know it is medium risk? by listening to tenure-seeking "experts"?), you need to put a portion, say 85 to 90 percent, in extremely safe instruments, like Treasury bills—as safe a class of instruments as you can manage to find on this planet. The remaining 10 to 15 percent you put in extremely speculative bets, as leveraged as possible (like options), preferably venture capital-style portfolios. That way you do not depend on errors of risk management; no Black Swan can hurt you at all, beyond your "floor," the nest egg that you have in maximally safe investments."

This is in no way a suggestion that any of us should invest in a strategy like this. This is a thread to discuss specific, practical, hypothetical components that an investor in this type of strategy could use to construct their barbell.

Personally, I'm more interested in publicly traded investments than private equity.

I don't have many ideas to share, but here are a few.

Positive Black Swans

Bitcoin - TBH I just sold all of my bitcoin. But I still think of this as an area with possibly unlimited upside. I also *like* the idea of others piling into the trade using stocks like RIOT and bidding up the price of blockchain-related ETPs way above NAV. The next time we see a slew of "I-told-you-so" Bitcoin articles about all those silly tulip chasers, I'll be levering up through instruments like these rather than buying BTC itself, since I'm not a believer anyway. Are there any ways to get direct leveraged exposure to BTC?

Call Options - I am an options noob recently trying to educate myself. My problem with call options is that when they are most useful (after big market declines), they are also most expensive. If this is a misconception, I would like to clear it up. Can anyone recommend good resources to learn options trading? I'm not sure if I should take a class at my local business school, read some books (which ones?), learn through websites (which ones?), or all of the above.

Hedge Fund Copycat - Just last year I put a small amount into gold mining penny stocks highlighted on a series of YT videos by Crescat Capital. I don't really believe any of their story, but I think the fact that they are telling it increases the probability of these penny stocks doing well. One of them is up over 600% since I bought so that's cool. I haven't used this strategy with anything else. Anyone else have ideas for this strategy?

How else can we get exposure to positive black swans in our barbell strategy?

Negative Black Swans

USD - USD losing its status as world reserve currency would be a tremendous black swan. At first thought, it seems like there are lots of direct leveraged trades to short USD via the FOREX exchange (e.g. just go long EURUSD). But on second thought, if all currencies lose against whatever the new reserve currency will be, then it may not be quite so easy to pick relative winners among the losers. What else can we do to get exposure to this event in a barbell?

Put Options - Again, total noob options trader here. I love the irony of puts in that they are cheapest when they are most useful and valuable. How beautiful is that. I get the math behind simple hedging strategies using SPX puts, but what if you want to seek greater profits in your barbell? How do you identify a real turd to maximize the potential payout of your puts? I know, that's a big question. Any books (or anything else?) that you would recommend on the subject? I know that's like asking the industry of short sellers to reveal their secrets, but hey it doesn't hurt to ask.

What other strategies should we stick on the negative side of our barbell?