Mike Flaum (Grain of Salt): Shares per Bitcoin, MSTR Preferreds, and AI Research Workflows

Mike Flaum (Grain of Salt): Shares per Bitcoin, MSTR Preferreds, and AI Research Workflows

Author: Tony Carrera February 16, 2026 Duration: 1:43:08

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:


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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.


Hosted by Tony Carrera, Proof of Pain digs into the tangible sacrifices and strategic decisions required in an economy increasingly shaped by sound money principles. This isn't about abstract theory; it's a close examination of the real-world costs and the consequential opportunities that emerge from this financial shift. While the core of the podcast is firmly rooted in Bitcoin-exploring its ecosystem, mining operations, treasury strategies, and derivative markets-the conversation often finds compelling parallels elsewhere. Carrera brings on guests from diverse fields like professional sports and traditional business, individuals who understand fundamental incentives and high-stakes tradeoffs in their own arenas. Through these discussions, the show builds a broader narrative about value, risk, and commitment. You'll hear detailed analysis on specific Bitcoin-focused investment vehicles and company strategies, balanced with wider reflections on how the mindset of sound money applies far beyond digital assets. For anyone navigating the complexities of modern investing, this podcast offers a grounded, often provocative perspective on what it truly takes to build and preserve wealth in a changing world. New episodes are released on a regular schedule.
Author: Language: en-us Episodes: 12

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