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On The Brink with Castle Island


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 insider trading on prediction markets?
  • Clarity Act odds are trickling down
  • Strategy shores up their balance sheet
  • Is the Bitcoin cycle finally turning?
  • Stripe bids for Paypal
  • The AI DeFi apocalypse didn’t happen
  • Kathy Hochul’s AI datacenter moratorium
  • Why is Anthropic running ads suggesting that they could cause extinction
  • The DTC is using Canton for it’s tokenized settlement pilot
  • Brian Chesky’s AI slop thread debacle
  • Jesse Pollak leaves Base
  • CBDCs are officially banned federally