Very often, I’ll speak to allocators who have target return objectives for their investments. I usually express that I’m not a fan of this approach, particularly when it comes to long volatility strategies.
Let me explain why.
Imagine you have a friend who tells you, “Hey, I’m a good poker player. I’m going to play at this casino tonight, and I’m not leaving until I make $500K.”
He starts with a bankroll of $50K. He’s a skilled player, and fortunately, he’s seated at a table with players who are considerably worse than him.
Nine hours go by, and he’s now up $450K. However, the table dynamics change. A few players rotate out, and two players he recognizes from other circuits sit down. He knows both are significantly better than him.
To me, a good poker player would recognize that the opportunity set has deteriorated. He might play a few more hands with a strict floor in mind, but if that floor is breached, he picks up his chips and calls it a night.
Unfortunately, our friend has committed himself to his original rule: He cannot leave until he makes $500K.
So he continues playing. Nine hours later, he has lost everything.
Now, let’s change the scenario.
Instead of two superior players joining the table, imagine two more fish sit down. Our friend plays another hour, makes the additional $50K, reaches his $500K target, and walks away.
Unfortunately, those two fish each have an additional $2M bankroll and are willing to keep playing all night.
In the first scenario, had he recognized the deterioration in the opportunity set, he could have walked away with $450K instead of nothing.
In the second scenario, had he recognized the improvement in the opportunity set, he might have walked away with $2M instead of $500K.
So what went wrong in both scenarios?
He allowed an arbitrary return target to dictate his decisions rather than the underlying conditions that actually determined his expected profitability.
This is the fundamental problem I have with target-based investment frameworks.
When you establish external parameters that have no meaningful relationship to the underlying distribution of outcomes, you risk systematically making the wrong decisions. You end up taking too much risk when the opportunity set deteriorates and taking too little when it improves.
Now, bring this back to volatility investing.
I often speak with allocators who say things like, “We want our hedging program to generate a 40% return if the market declines 20%, and we want to monetize when that happens.”
I try my best to explain that the parameters you establish for your hedging program have absolutely no influence on the path the market takes or the opportunity set that develops along the way.
A 20% market decline tells you very little, in isolation, about whether the remaining convexity is attractively priced, whether volatility is likely to continue expanding, or whether the positioning dynamics that created the opportunity have been exhausted.
This is precisely why so many hedging programs struggle with monetization. They either monetize too early, leaving substantial profits on the table, or monetize too late, allowing significant gains to evaporate.
The problem isn’t necessarily the hedge itself. It’s that the decision to monetize is being driven by an arbitrary objective rather than the variables that actually determine the expected value of continuing to hold the position.
The objective should never be to maximize returns relative to an arbitrary target. It should be to maximize the value extracted from the opportunity set as it evolves.