I have one trade that stands out head and shoulders above the rest as my number one F-up. I really screwed this one up.
Financially, it was my best trade of the year. Probably my best trade in several years…
But it still stands out as my worst trade of all time.
This was circa 2013. I had recently moved to Boulder, CO and life was good. New vistas, new friends, new environments, new everything.
And one thing I did which was new for me (at the time), was I had come up with a long-term bullish thesis on a stock. And over the course of a couple days, I wrote up about 5 pages of notes on my yellow legal pad outlining exactly how I’d play my bullish thesis using options.
The TL;DR version of my strategy is that I was going to purchase slightly out-of-the-money long calls with about a month until expiration. And then if/when the stock traded up and through the strike price of my long calls, I would take that opportunity to roll those options up and out to the next monthly series, using the proceeds from the sale of the existing ITM options to purchase as many new OTM options in the next month as possible. (For example, I’d sell 5 calls with Feb expiration for $5.00 a contract, then buy 7 calls with March expiration for $3.50 apiece. My position would grow in size, and I’d even extract a little leftover credit. Wash, rinse, repeat all the way to the moon.)
This was a super-aggressive, GO FOR IT! trade. [Read more…]