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On The Brink with Castle Island

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...


Feb 18, 2026

Wyatt sits down with Raj Parekh, Head of Stablecoins and Payments at Monad. In this episode:

  • Will enterprises build out their own stablecoin solutions?
  • Will card payments continue to grow, or be challenged by other forms of payments?
  • What is the role of governments in driving whether stablecoin adoption will continue,...


Feb 13, 2026

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

  • Matt reflects on the Patriots season
  • We review the Superbowl Ads
  • Looking forward to the OpenAI wearable
  • Is “something big happening” in AI?
  • Does crypto accelerate the rise of malicious AI?
  • Are all communications networks going to break...


Feb 11, 2026

Wyatt sits down with Bhavin, co-founder of Birch Hill to chat about the tokenized asset and DeFi market broadly. In this episode:

  • Who is assessing whether cryptoassets are safe in DeFi today?
  • Who is assessing risk and ensuring assets are solvent and not fraudulent?
  • How have these standards been set and how are...