Brian Brookshire: Missed Bitcoin? Microstrategy Beats It Over The Long Run

In this deep-dive interview, Brian and I explore Bitcoin investment strategies, Microstrategy's (traded as $MSTR, recently rebranded as Strategy) trajectory under Michael Saylor, and how to analyze other Bitcoin treasury companies like Metaplanet and Semler Scientific. Brian shares unique first-principles frameworks for evaluating Bitcoin, discusses GameStop’s Bitcoin strategy, and unpacks key concepts like ATM financing instruments, convertible notes, and preferred stock.

We cover the technology adoption curve of Bitcoin, the implications of Strategy’s Nasdaq 100 inclusion for a potential future S&P 500 listing, and how leveraging debt can amplify Bitcoin exposure. Brian also reveals his favorite Bitcoin treasury company beyond MicroStrategy, his insights on Jack Mallers’ 21 Capital with Cantor Fitzgerald and Tether, and how a multilingual background can provide an edge when evaluating global Bitcoin opportunities like Metaplanet.

Whether you’re a seasoned investor or new to the world of Bitcoin, crypto, and Bitcoin treasury strategies, this conversation will help you think critically about how to approach Bitcoin investing from both short- and long-term perspectives.

Timestamps:

0:43 - Strategy’s “42 42 Plan” explained

2:20 - Short-term vs long-term Bitcoin investing

2:42 - ATM instruments, convertible notes, and preferred stock: key differences

5:45 - GameStop’s surprising Bitcoin strategy

7:59 - Technology adoption curve for Bitcoin and crypto

10:05 - Strategy’s Nasdaq 100 inclusion and implications for S&P 500 eligibility

13:19 - First Principles: Evaluating Bitcoin if starting today

16:34 - First Principles: Using arbitrage and debt to buy Bitcoin

20:18 - First Principles: How Bitcoin changed Brian’s investing

24:00 - Key KPIs to analyze Strategy/MicroStrategy ($MSTR)

29:17 - Analyzing Bitcoin treasury companies without a finance background

32:13 - Jack Mallers’ 21 Capital, Cantor Fitzgerald, and Tether

35:34 - Brian’s excitement about Bitcoin’s future

36:47 - Brian’s favorite Bitcoin treasury company beyond Strategy/MicroStrategy

39:24 - How Brian’s Japanese degree helps with Metaplanet analysis

40:05 - Brian’s view on Semler Scientific ($SMLR)

42:14 - Brian’s current reading and listening list

43:13 - Researching Metaplanet’s “ATM-like” financing instrument

44:43 - Where to follow Brian

➡️ Don’t miss this essential discussion on Bitcoin investing, Michael Saylor, MicroStrategy, Metaplanet, Semler Scientific, Jack Mallers, GameStop, Tether, and the future of Bitcoin treasury strategies.

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