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On The Brink with Castle Island

Mar 6, 2026

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

  • What Dario Amodei and SBF have in common
  • Trump wades in to the market structure debate and asks the banks to come to the table
  • Why stablecoins are not like banks
  • Kraken Financial gets a skinny Fed master account
  • Visa and Bridge are rolling out...


Mar 4, 2026

Alex Wilson, Co-Founder and CEO of Cyclops, joins the show. In this episode:

  • Alex’s background running The Giving Block and the company’s acquisition by Shift4
  • Difficulty in enabling stablecoin solutions when utilizing existing providers while inside of Shift4
  • Backgrounds of the founding team at Cyclops
  • Regulatory...


Mar 3, 2026

Dana Syracuse and Josh Boehm of Paul Hastings join the show. In this episode we discuss:

  • The OCC Charter process how digital asset companies are pursuing the federal path
  • The aftermath of the Genius Act passage and the rulemaking process for this law
  • Considerations for Federal vs. State charter pathways
  • The market...


Feb 27, 2026

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

  • Kalshi has detected and banned two accounts for insider trading
  • Is Polymarket going to have to add KYC?
  • Is there a tradeoff between informational efficiency and market fairness
  • The OCC de facto bans stablecoin yield in its rulemaking...


Feb 20, 2026

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

  • Crypto VC funds have some dry powder
  • CFTC chair Mike Selig asserts jurisdiction over prediction markets relative to the States
  • Is Kalshi more reliable than interest rate futures?
  • The CLARITY Act inches closer to passing
  • Shake up at...