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On The Brink with Castle Island

Jul 31, 2026

Matt and Nic are back for another week of news and deals. In this episode: 

  • What the novel Hyperion tells us about AI doom
  • Situational Awareness liquidates most of its public book after a sharp AI selloff
  • Will Leo have a second act?
  • Why has AI been selling off?
  • Over 1000 BTC stored in Coldcard wallets were stolen due...


Jul 24, 2026

Nic and Matt are back for another week of news and deals. In this episode: 

  • The Fat Model Thesis
  • Are OAI and Anthropic in real trouble with Kimi?
  • The Bitcoin Security Consortium is announced to tackle quantum risk
  • Galaxy announces their Quantum Readiness Initiative
  • Clarity is beleaguered in Washington
  • Polymarket and...


Jul 17, 2026

Matt and Nic are back with the deals and news of the week. In this episode: 

  • Nic licks his World Cup wounds
  • Do Bitcoin Treasury strategies make sense?
  • Trying to make sense of Saylor’s “bitcoin rating”
  • Trump’s teleprompter operator has been trading on what Trump is going to say in his speeches
  • Why do people keep...


Jul 10, 2026

Matt and Nic are back with another week of news and deals. In this episode: 

  • Strategy sells $216m worth of BTC
  • Where does Strategy go from here with STRC?
  • Kalshi’s case faces the ban of sports contracts in NY
  • TeraWulf signs a massive lease with Anthropic
  • BonkDAO’s legal hack
  • Vanguard hires a head of digital...


Jul 3, 2026

Matt and Nic are back with another week of news and deals. In this episode: 

  • Saylor releases Strategy’s “Digital Credit Capital Framework”
  • MSTR stabilizes for now though STRC is still discounted
  • Is Saylor transitioning MSTR into a Bitcoin hedge fund?
  • Is Strategy doing anything tricky with their...