August 2026 Random Ramblings

YAVP #411

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 to sell when there is no price to anchor to, whether the crossover funds actually had an AI information edge or just conviction, why I cannot make the memory valuations work under any assumption I am willing to make, and where I think the real opportunity is: the beaten-up AI power names Situational owned in size, several of which are not trading far above the DCF of the contracts they already have.

---

This podcast is sponsored by Trata

I already know you’re going to like trata. Why? Because you’re reading this blog post, meaning you’re interested in this podcast. And trata is just like this podcast (though without the handsome host!). Trata is anonymized transcripts of buysiders discussing stocks they are following and what they really think will drive the stock. I’ve been mentioning it on the podcast for months, and the most frequent complaint I hear from people who check it out is they wish trata had more content on more of their stocks. Even better: they recently released an MCP that lets you connect their transcripts to the AI model of your choice. If you’re interested, check out a free transcipt on GLXY here.

---

Please follow the podcast on Spotify, iTunes, or YouTube! And please be sure to rate / review the podcast if you enjoy it, or share it with someone else who would enjoy it (more listeners is a critical part of the flywheel that keeps this Substack and podcast going!).

Transcript for paid subs begins below (The initial transcript is AI-generated and is replaced with a professionally edited version when available)

Disclaimer: Nothing on this podcast or on this blog is investing or financial advice; please see our full disclaimer here. The transcript below is from a third party transcription service; it’s entirely possible there are some errors in the transcript.