Shares per Bitcoin, Preferreds, and the MSTR Machine (Grain of Salt) | Proof of Pain

Mike Flaum (“Grain of Salt”) breaks down Bitcoin investing through a product-manager lens: optionality, taxes, IRAs, and why “shares per bitcoin” may be the clearest way to understand Bitcoin treasury companies like Strategy (MSTR). We also go deep on AI – how to “battle” with models using deep research workflows – and why preferreds changed the treasury playbook. Topics: Product-manager investing: TAM, tradeoffs, and first principles Paying taxes vs never taking profit Bitcoin in IRAs (and why wrappers and buckets matter) Strategy ($MSTR): converts vs preferreds vs cash “Shares per Bitcoin” vs “Bitcoin per Share” (the pizza analogy) AI deep research + cross-checking models (ChatGPT/Claude/Grok) Why mNAV can mislead + the metric Mike would require for all treasuries Links / references: Mike's background: https://www.logscaleinvestments.com/i... Mike on X (Grain of Salt @Z06Z07): https://x.com/Z06Z07 BitInfoCharts “Rich List” (address distribution): https://bitinfocharts.com/top-100-ric... Clarke’s Third Law (“advanced tech looks like magic”): https://en.wikipedia.org/wiki/Clarke%... IRS Corporate Alternative Minimum Tax (CAMT) interim guidance (Notice 2025-49 PDF): https://www.irs.gov/pub/irs-drop/n-25... Mike’s books: “Magic Mirror” (AI) “I Am Root” (AI) “The Rise, Fall, and Reemergence of Bitcoin Treasury Companies” Link to books: https://www.logscaleinvestments.com/i... Chapters: 0:00 Intro + Mike’s background (tech + investing) 3:40 Investing like a Product Manager (TAM, models, tradeoffs) 7:00 The “P-word”: profit, taxes, and mindset 17:40 Bitcoin discovery (2013–2017) + why IRAs mattered 33:50 Finding Strategy (MSTR) + skepticism → conviction 39:20 AI deep research + “battle” workflows 47:00 Claude vs ChatGPT + “operator” mindset 56:20 How search works (operators / intent / structure) 1:05:20 Strategy as “digital credit” + preferreds 1:07:25 Shares per Bitcoin vs Bitcoin per Share (pizza analogy) 1:20:50 Treasury companies: what matters, who’s run well 1:29:10 FASB fair value + CAMT confusion (why people miss this) 1:37:25 Rapid fire: good and bad metrics, 2026 Bitcoin and MSTR price targets If you got value out of this, drop a comment! Not financial advice. Educational discussion only.