August 2026 Random Ramblings
About this episode
The episode discusses capital allocation strategies and the challenges of selling thematic trades in the context of recent market movements.
Strategy filed an 8K this morning: they sold $300 million of stock, sold $100 million of bitcoin, and put the proceeds into buying back roughly $80 million of their own preferred at a discount. So you have a company trading over NAV, diluting shareholders, and selling the one asset it exists to hold, and it is still trading at a premium. Management is presenting the move from "one-way capital issuer" to "multi-way capital issuer" like it is a financial engineering breakthrough. It is just normal capital allocation, and it took them five years to get there. That is the through line for this whole ramble: selling. Strategy made a genuinely good call in 2020 and then never sold a thing. Situational Awareness made a generational call, long AI winners and short AI losers, went up something like 10x on it, never rebalanced, kept pressing a trade that naturally degrosses, and blew up when software went from 20 back to 30 and semis went from 400 back to 370. I do a miniature version of the same thing every time I decide in advance that I will start trimming at 15 a stock I bought at 10, and I am not sure that plan is as smart as it feels. I also get into why thematic trades are so hard…
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