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On The Brink with Castle Island

Oct 9, 2026

Matt and Nic are back with more deals and news. In this episode: 

  • Is it appropriate to have AI manage your fantasy league?
  • Quant firms are hiring “quals”
  • Justin Drake scares everyone in crypto
  • Did AI destroy math?
  • Why a classical ECDSA break would be worse than a quantum one
  • Why we lean forward hash-based...


Oct 5, 2026

Esther Wong, founder and CEO of Cashi joins the show. Cashi is a stablecoin spending app and cashback card with a global footprint. In this episode we discuss:

  • Customer personas and use cases for stablecoin payments
  • The future of tokenized equities on chain
  • The landscape of layer one and two blockchains and how these...


Oct 2, 2026

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

  • Are OpenAI and Anthropic reenacting the Fat Protocol Hypothesis
  • Will AI agents cause bank runs optimizing bank balances for yield?
  • If the AI complex bursts does it take down VC?
  • Our tribute to Hester Peirce as she retires from the SEC
  • The SEC...


Sep 25, 2026

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

  • How loud are America’s largest data centers?
  • What’s wrong with XAI’s data center in Mississippi?
  • The Trump admin is reportedly trying to promote dollar stablecoins
  • Binance invests in Circle
  • We pick up the pieces after Clarity
  • Fairshake...


Sep 18, 2026

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

  • How is SBF like Dario?
  • The EAs are at it again
  • Do we need new regulation to Pace the Frontier?
  • Can Anthropic be regulated like a bank? 
  • Are baseball cards back?
  • Clarity fails at the final hurdle
  • Why did Clarity fail?
  • Stablecoin yield is still...