Portfolio Pursuit

It's that headline risk

October 10, 2025

The euphemism "headline risk" has become frustratingly more en vogue this year. In April I got slammed, as did some friends by the "headline risk" of President Trump announcing idiotic tariffs on our friends, allies, but curiously not our enemies.

Today's "headline risk" worked out in my favor for a change.

I was heading into the open expecting my CoreWeave (CRWV) and Shopify (SHOP) covered call positions to get exercised as both companies had had a pretty meteoric risk over the preceding two weeks in large part thanks to OpenAI:

These unexpected announcements meant the ambitious options were way out of the money most of the week. Then through the magic of headline risk both companies retreated with the rest of the market causing them to be in the money. I was fortunate to catch the tug-of-war heading into the close on Friday and re-sell covered calls for the following week which I am far more pleased with.

I made a little money off of the headline risk this week, but nothing compared to the insider trading money being made off the same headlines:


Portfolio

Trades

  • CRWV 10OCT25 140 C
  • CRWV 10OCT25 141 C
  • CRWV 10OCT25 142 C
  • CRWV 17OCT25 141 C
  • CRWV 17OCT25 142 C
  • CRWV 17OCT25 145 C
  • SHOP 10OCT25 150 C
  • SHOP 17OCT25 157.5 C

Holding

Equities

  • COST
  • CRWV
  • IBKR
  • SHOP

Options

  • CRWV 17OCT25 141 C
  • CRWV 17OCT25 142 C
  • CRWV 17OCT25 145 C
  • SHOP 17OCT25 157.5 C