Inside Strategy: How the World's Biggest Bitcoin Company Actually Works | Chaitanya Jain #215

Inside Strategy: How the World's Biggest Bitcoin Company Actually Works | Chaitanya Jain #215

March 11, 2026 · 56 min

About this episode

Chaitanya Jain discusses the inner workings of Strategy's Bitcoin team and the significance of their new product, Stretch.

CJ, part of the Bitcoin team at Strategy, joins Jordan to explain what’s really happening behind the company’s new preferred equities — and why Stretch is becoming a headline product. 🇬🇧 Join the UK Bitcoin Business Network: https://bitcoincollective.co/bbn/ CONTACT JORDAN: X: https://x.com/JayW132 LinkedIn: https://www.linkedin.com/in/jordan-walker-293955106/ Email: hello@bitcoincollective.co CONTACT CJ: X: https://x.com/CJ_Bitcoin LinkedIn: https://www.linkedin.com/in/jainchaitanya CHAPTERS: 00:00 Intro 00:51 CJ’s role on Strategy’s Bitcoin team 02:12 What CJ does day to day 05:25 Behind Saylor’s messaging and Strategy’s content 08:34 What CJ has learned working closely with Saylor 11:22 Why Strategy uses AI so aggressively 14:21 How the Bitcoin and software sides fit together 17:07 Strategy’s model explained (Jesse Meyers graphic) 24:27 What Stretch is and why it exists 27:27 How Stretch helps Strategy buy more Bitcoin 31:07 How the dividend rate gets set and adjusted 34:43 Stretch vs stablecoin yield 38:44 Why Stretch could be Strategy’s “iPhone moment” 41:41 Who can copy this model and why size matters 44:46 Building products on top of Stretch outside the US 46:28 A UK…

People in this episode

Host: Jordan Walker

Guest: Chaitanya Jain

Mentioned in this episode

Organizations: Strategy, Bitcoin, UK Bitcoin Business Network, Saylor

Products: Stretch, iPhone

Places: UK

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