Episode Details

In this episode of Proof of Pain, Tony sits down with Mike Flaum (Grain of Salt) to break down Bitcoin investing through a product manager lens: optionality, taxes, IRAs, and why “shares per Bitcoin” can be the clearest way to understand Bitcoin treasury companies like Strategy (MSTR).

We also go deep on AI research workflows, how to battle models, and why preferreds changed the treasury playbook.

What we cover• Product manager investing: TAM, tradeoffs, first principles• Paying taxes vs never taking profit• Bitcoin in IRAs, wrappers, and buckets• Strategy (MSTR): converts vs preferreds vs cash• Shares per Bitcoin vs Bitcoin per Share (pizza analogy)• AI deep research workflows (ChatGPT, Claude, Grok)• Why mNAV can mislead, and the metric Mike wants standardized

Chapters

0:00 Intro and Mike’s background3:40 Investing like a product manager7:00 Profit, taxes, and mindset17:40 Bitcoin discovery and why IRAs mattered33:50 Finding Strategy (MSTR)39:20 AI deep research and battle workflows56:20 How search and operators really work1:05:20 Strategy as digital credit and preferreds1:07:25 Shares per Bitcoin vs Bitcoin per Share1:20:50 Treasury companies: what matters1:29:10 FASB fair value and CAMT confusion1:37:25 Rapid fire

Links / references:

• Mike's background and books: https://www.logscaleinvestments.com/identity
• BitInfoCharts “Rich List” (address distribution): https://bitinfocharts.com/top-100-richest-bitcoin-addresses.html
• Clarke’s Third Law (“advanced tech looks like magic”): https://en.wikipedia.org/wiki/Clarke%27s_three_laws
• IRS Corporate Alternative Minimum Tax (CAMT) interim guidance (Notice 2025-49 PDF): https://www.irs.gov/pub/irs-drop/n-25-49.pdf

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Video of this episode on Youtube:

https://www.youtube.com/watch?v=5YuInVeimGc

Not financial or tax advice. For entertainment only.