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Asymmetry: cut the left tail, keep the right

Good investments have more upside than downside. How to build that asymmetry into a portfolio — and what it looks like in the data.

An asymmetric bet is one where you can win much more than you can lose. Venture capital is the classic example: most investments fail, a few return 10 or 100 times, and those few pay for everything.

Asymmetry in a portfolio

You can create asymmetry in two ways:

  • Position size — if each position is small, the most you can lose on it is small, while a winner can grow many times over.
  • Rules that cut losses and let winners run — stepping out of a market in a persistent downtrend limits the downside; staying in while the trend is up keeps the upside open.

What it looks like

Here is every month of the S&P 500 since 1993, sorted by return — buy & hold versus a trend-following rule:

Monthly returns: buy & hold vs a trend-following rule
Number of months by monthly return (bucket = from that value up to +2%; outer buckets include everything beyond) · hypothetical backtest incl. costs

The right side of both distributions — the good months — looks similar. The difference is on the left: the rule has far fewer deep losing months. In our data, the worst single month for buy & hold was around −20%; for the rule, about half that. More months near zero (when the rule is in cash) is the price for a thinner left tail.

You do not need to be right more often. You need your losses to be smaller than your gains.

Related: volatility · max drawdown

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Educational content, not investment advice. Disclaimer.