You might not have heard of Mohnish Pabrai, but he's one of the modern greats in investing.
"Heads I win. Tails I don't lose much" is an approach that's made him very rich. The basic idea is that before you invest, you should consider the downside, and only invest in that idea if you have a high conviction of success and you don't expect the downside to be too bad, if you're wrong.
Yes, there's a sense of having your cake and eating it too, but for a risk-averse investor the idea itself is a useful framework.
Think about Harvey Norman Holdings Limited (ASX:HVN) a couple of years ago. The share price was less than the value of all of the property on the company's books. Sure, that number could prove too high, but it was a reasonable backstop for your valuation.
Or Fairfax Media Limited (ASX:FXJ), now the subject of a takeover offer. Its Domain business is conservatively valued at around $2 billion. So, pre-takeover, there was a decent reason to believe the company was worth at least that.
But don't be mistaken. Harvey Norman's shares could well have fallen further, as the market remained irrational. Fairfax could have chewed up all of Domain's value as it supported a loss-making media business for decades.
So nothing is perfect or failsafe. But 'Heads I win, tails I don't lose much' is an interesting approach if you don't like taking too much risk. Speaking of which, another way to moderate your portfolio risk is through dividends. You get paid, management has less opportunity to waste the money, and it's real cash in the bank, twice a year!