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On The Brink with Castle Island

Apr 9, 2026

Connor Dougherty, Co-Founder and CEO of Valinor Digital, joins the show. In this episode:

  • Connor’s background working at a large private credit shop
  • Pioneering a new category of Open Credit and how it expands the TAM for private credit
  • Explosion of stablecoin demand enabling new borrowing types
  • Structuring deals...


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 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 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...