In this episode, we sit down with Chaitanya Jain (CJ), an MBA candidate at Harvard Business School and strategist at MicroStrategy, who worked closely with Michael Saylor on the recent open source Bitcoin24 model. CJ shares his experience talking about bitcoin at HBS, detailing efforts to distinguish it from broader crypto discussions. We explore Michael Saylor’s perspective on whether bitcoin is money or just another asset. CJ offers insights into building the Bitcoin24 model and MicroStrategy’s evolving custody strategy, including the future of bitcoin in banking and other companies adopting MicroStrategy’s bitcoin strategy. We also cover their acquisition strategy using equity and convertible notes, the constraints they face, and how to think about valuing MicroStrategy in relation to their NAV. Last, CJ discusses MicroStrategy's potential future S&P 500 inclusion, effective bitcoin advocacy techniques, and the most significant risks to bitcoin today.

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TIMESTAMPS:

00:00:00 Introduction and background

00:03:23 Experience at HBS with bitcoin

00:06:06 Efforts to differentiate bitcoin from crypto at HBS

00:08:13 Bitcoin and crypto courses at HBS

00:10:21 Michael Saylor’s view of bitcoin: money or asset?

00:12:12 Catalysts for HBS interest in bitcoin

00:14:06 Key takeaways from interacting with Michael Saylor

00:18:25 Valuing bitcoin without cash flows

00:20:36 Building the Bitcoin24 model with MicroStrategy

00:24:24 MicroStrategy’s bitcoin custody strategy

00:26:32 Future of bitcoin in banking

00:30:55 Other companies following MicroStrategy’s bitcoin strategy

00:38:21 MicroStrategy’s bitcoin acquisition strategy: equity and convertible notes

00:46:24 Limits on equity issuances and convertible notes

00:50:24 Common misunderstandings about MicroStrategy

00:52:42 MicroStrategy’s inclusion in the S&P 500

00:58:26 Bitcoin advocacy and persuasion techniques

00:59:10 Biggest risks to bitcoin

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The Bitcoin Frontier

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