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On The Brink with Castle Island

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...


Jun 26, 2026

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

  • Our recording snafu
  • STRC's depeg explained
  • Saylor's path forward
  • Why Strategy's issue is the converts 
  • Polymarket's questionable marketing
  • Trump's Quantum EOs


Jun 19, 2026

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

  • The Tartan Army takes over Boston
  • Europeans are shocked that American infrastructure works
  • STRC falls into the low $80s
  • STRC’s liquidation cascade mechanics
  • What are Saylor’s options now?
  • Is the US right to put the brakes on Fable?
  • Will open...


Jun 12, 2026

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

  • Spanish soccer club Osasuna hedges their relegation on Kalshi
  • Strategy shocks people by buying the dip
  • Is Strategy sacrificing MSTR to save STRC?
  • Saylor bolsters his cash position
  • What factors are dragging on the BTC price?
  • Zcash fixes a scary...