Unchained

Twenty One Aims to Buy as Much Bitcoin as Possible. Can It Succeed? - Ep. 824


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A new company called Twenty One is making waves—with a launch strategy that echoes Strategy (formerly MicroStrategy), a cap table that includes Tether, SoftBank, and Cantor Fitzgerald, and a plan to acquire more Bitcoin than anyone else.

They’re starting with 42,000 BTC, worth nearly $4 billion, and they’ve hinted they’ll use convertible debt, equity raises, and other market mechanics to buy more.

But is this just a smarter MicroStrategy? Or a recipe for financial reflexivity gone wrong?

In this episode, Matthew Sigel, head of digital assets research at VanEck, digs into:

  • How the strategy works and why it could break
  • What happens if the stock trades below NAV
  • Why timing the market may be a feature, not a bug
  • And whether this signals a new phase in corporate Bitcoin exposure
  • Sigel also shares a bold idea for “BIT Bonds” that could let the U.S. Treasury issue Bitcoin-linked government debt. Could it work?

    Plus, Unchained regulatory reporter Veronica Irwin talks about her scoop that we might see a crypto market structure bill as early as this week. 

    Visit our website for breaking news, analysis, op-eds, articles to learn about crypto, and much more: unchainedcrypto.com

    Thank you to our sponsors!
    • Bitkey: Use code UNCHAINED for 20% off
    • FalconX
    • Mantle
    • Guest
      Matthew Sigel, Head of Digital Assets Research at VanEckLinks
      • Unchained: 
      • Press Release: Tether, SoftBank Group, and Jack Mallers Launch Twenty One, a Bitcoin-native Company, Through a Business Combination With Cantor Equity Partners
      • The Block: Strike founder Jack Mallers to lead Tether-backed multi-billion bitcoin buying venture, Twenty One Capital
      • Ryan Watkins’ post on X
      • Jeff Park’s post on X

      • Timestamps:

        👋 0:00 Introduction

        🚀 4:59 How Twenty One plans to buy more bitcoin than anyone else

        ⚠️ 7:23 The key risks behind the reflexive BTC acquisition strategy

        📈 12:38 Why more companies are copying the MicroStrategy playbook

        👔 16:17 Jack Mallers’ role and why the CFO matters even more here

        💥 17:55 Could one bad move blow these companies up?

        💰 22:28 The types of investors this model attracts

        ⏳ 25:40 Did Twenty One launch at the worst possible time?

        🤔 26:58 How to think about investing in BTC vs. these BTC-heavy stocks

        🇺🇸  28:23 Unchained regulatory reporter Veronica Irwin on why a market structure bill might be on its way relatively soon

        📰 35:31 Crypto News Recap

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        UnchainedBy Laura Shin