I mean, do I really know my risk?

Stocks and Futures traders like to talk about how they use stop-loss orders to define their risks, and that’s smart.

A lifetime ago I managed a small, independent hedge fund that traded commodities with a trend-following strategy. This strategy entered positions that I’d attempt to hold for weeks or months (if they were working).

Every position I had on had a resting stop-loss order working in the market, giving me comfort that I knew the most I could lose if I was wrong.

All that comfort I was enjoying changed one day after a trip to my clearing firm’s office in downtown Chicago.

I sat down with one of the firm’s risk managers for a simple “get-to-know-you” chat. He was curious about my trading and just wanted to get to know me a little better and see if there were any ways in which he could help me get to the next level.

We got into the weeds of my trading strategy and he was nodding along in agreement that he was in favor of what I was doing and he thought the returns I was earning were impressive and better than average for accounts of similar size with that firm.

When we got on to the topic of how much risk I was taking in each position, I had my riff on position sizing and trailing volatility stop-loss orders ready to rip.

But then, mid-speech, he interrupted with a show-stopper: [Read more…]

If you would’ve told me a few months ago that we’d see a large crypto exchange (FTX) go bust and later a number of big banks become insolvent and collapse to zero, I would’ve laughed you out of the room if you followed up with: “…and bitcoin will rally.”

I mean, there is no way I would’ve agreed with that sentiment.

Thankfully, I don’t get paid for my opinions. Because the market couldn’t care less about what I think.

The strength in Bitcoin (and crypto in general) has truly been a sight to behold in recent months and in particular over the last few weeks.

The poster child instrument to play bitcoin in the equities market is via Microstrategy $MSTR. For those with their head in the sand on all thing bitcoin, this software services company has transformed itself into essentially a bitcoin ETF, having invested all of its working capital into bitcoing, and taking loans to leverage into even more bitcoin.

We’ll leave the discussion on whether or not this is crazy to another blog post. But for now, MSTR offers us a great way to participate in continued strength in bitcoin and we’re going to do it with a defined risk options spread. [Read more…]

The shorter my timeframe, the shittier the market. ~ Brian Lund @bclund

That quote was uttered during a Twitter spaces I hosted yesterday in which we discussed the emergence of “0-DTE” options and the opportunities and challenges they are spawning.

As Brian brought up, the phrase “0-DTE” which stands for “zero days until expiration” is a bit of a misnomer as options that are expiring today were not necessarily first listed for trading on the same day that they expire. Regarding SPY or SPX options, some of these “daily” options are first listed for trading as far as two weeks from expiration day. So if you were to look at the options chain for SPY, you would see options expiring every day over the next two weeks.

As many of you know, I’m a frequent trader of SPY and SPX options. One of the things I do on a daily basis in my personal trading is to manage an ever-evolving delta-neutral-ish position in the S&P 500.

And in recent weeks, I’ve jumped into the deep end of the liquidity pool that is daily expiring options.

There appear to be attractive opportunities here. [Read more…]

All things considered, the tech sector is holding up well. This gives me some comfort that this is an area we can sell some delta-neutral options premium to ride out this market volatility.

But we’re going to do so carefully, defining our risks and playing it conservatively.

Check out this chart of the Technology Sector ETF $XLK:

The horizontal lines on this chart represent areas we can sell April options premium at that feel far enough away for me to like our odds.

We’re going to get involved with an Iron Condor. [Read more…]