OP Insider’s Edge 6.3.26

The single worst long-term hold I know of is also one of the best trades of the last fifteen years, and it's the same exact fund.

The only thing that changes is which side of it you're standing on.

It has lost more than 99.99% of its value since it launched, which sounds like a catastrophe until you realize it's the design.

Once you understand why a fund can be built to bleed down to nothing, you'll never get trapped on the wrong side of it, and you'll start to see the way a volatility trader actually reads this market.

So stick with me, because the trap is worth understanding before the edge is.

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The ticker is UVXY.

Plenty of traders reach for it when they get scared, because it's sold as insurance against a crash.

You buy it, volatility spikes, you profit, and for about a day that's exactly how it works.

Hold it longer than that and it bleeds.

I don't mean it drifts lower, I mean a single share bought when this thing launched in 2011 has lost more than 99.99% of its value.

The fund has had to run something like ten reverse splits just to keep its price from rounding to zero, jamming the shares back together every year or two so it still looks like a normal stock.

Strip those splits out and the decline is almost too big to fit on a chart.

And none of it is a malfunction. UVXY is doing precisely what it was engineered to do.

Here's the engine, because this is the whole game.

UVXY doesn't own "volatility," it owns VIX futures, and it has to constantly sell the ones about to expire and buy the next month out.

Most of the time that next month costs more than the one rolling off, so with every roll the fund is selling cheap and buying expensive, and it never stops doing it.

In a calm market that structure alone can eat somewhere between 50% and 85% of the value in a single year. That isn't a bad year, that's the blueprint working as intended.

So when somebody asks me about UVXY, my answer is simple.

Held for the long term, it's one of the great wealth destroyers ever built, and shorted, it's been one of the best trades of the last fifteen years, because you're essentially betting on gravity.

Now I have to be straight with you, because I traded volatility for a living and I've watched it wreck people who got cocky.

You do not short this thing and walk away.

When fear actually hits, UVXY doesn't move politely. In the COVID crash it ran from around $11 to roughly $130 in two weeks, and a spike like that wipes out a short who's asleep no matter how right the long-term math turns out to be.

The decay is real. So is the dynamite.

That's the lesson sitting underneath all of it.

In volatility, you don't get paid for guessing which direction the market goes tomorrow.

You get paid for understanding the structure underneath the product, the plumbing almost nobody bothers to look at, and then putting yourself on the right side of it.

That's the same way I'm looking at the new 1DTE options the CBOE just rolled out on individual stocks.

It's a real change in the market's plumbing, and my partner Licia and I have spent the last few months mapping the edge inside it, built around a daily read we call the Tilt.

It's the same discipline as the UVXY trade, just pointed at a fresh opportunity.

Read the structure, find where the edge actually is, and trade that instead of the headline.

We laid the whole thing here, including how the Tilt works and what we found doing it with our own money.

Your only option,

Mark Sebastian

 

Mark Sebastian

Mark Sebastian

Mark Sebastian is a former member of both the Chicago Board Options Exchange (CBOE) and the American Stock Exchange (AMEX), where he spent years mastering the art of options trading in the most competitive environment imaginable. As Chief Investment Officer at the hedge fund Karman Line Capital, Mark manages sophisticated options strategies for institutional clients. He is the author of two highly regarded books on options trading: ‘The Option Traders Hedge Fund’ and ‘Trading Options for Edge.’ Mark is a frequent guest on major financial networks including CNBC, Fox Business News, Bloomberg, and First Business News, where he provides expert commentary on market volatility and options strategies.

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About the Author

Mark Sebastian

Mark Sebastian

Former CBOE floor trader and CIO at Karman Line Capital. Author of ‘The Option Traders Hedge Fund’ with over 30 years of options trading experience.

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