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On The Brink with Castle Island

Jan 16, 2026

Matt and Nic are back after a week off. In this episode:

  • The Clarity market structure bill markup is delayed for now
  • Coinbase backs out of supporting Clarity
  • The bank lobby is trying to torpedo Clarity
  • Kontigo is accused of ignoring sanctions
  • X changes its API to block InfoFi
  • California’s wealth tax has backfired...


Jan 2, 2026

Matt and Nic are back for the first OTB show of 2026. In this episode:

  • Matt’s ice rink adventures
  • The House issues a draft of the PARITY Act
  • The trouble with wealth taxes
  • DATs continue to bleed out
  • We talk about Nic’s fiction story
  • Predictions for 2026
  • Is there a secret exchange insolvency?
  • What constitutes insider...


Dec 19, 2025

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

  • Secret exchange insolvency rumors
  • Caroline Ellison is free
  • David Sacks says CLARITY is getting a markup
  • The Fed rescinds their 2023 Novel Activities Supervision program
  • Insolvent exchange prediction markets
  • Visa’s stablecoin advisory business
  • JPM...


Dec 12, 2025

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

  • CIV grows the team
  • Nic does not regret 8 years in crypto
  • People are getting blackpilled about crypto
  • Does speculation in crypto have positive externalities?
  • Matt has never seen LOTR
  • Will web3 ever come back?
  • The OCC lets banks broker crypto trades
  • The...


Dec 5, 2025

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

  • Quantum risk again
  • Are banks filled with spooks?
  • The trouble with Taproot addresses
  • Microstrategy’s dollar reserve
  • Kalshi is going on chain
  • Prediction market predicaments
  • Are insiders monetizing Google search information on Polymarket?
  • Are...