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On The Brink with Castle Island

Jun 12, 2026

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

  • Spanish soccer club Osasuna hedges their relegation on Kalshi
  • Strategy shocks people by buying the dip
  • Is Strategy sacrificing MSTR to save STRC?
  • Saylor bolsters his cash position
  • What factors are dragging on the BTC price?
  • Zcash fixes a scary...


Jun 9, 2026

Wyatt sits down with Omid Malekan, a Professor at Columbia Business School, author of several books, and "Explainer-in-Chief" of blockchain technology. In this episode, Wyatt and Omid discuss:

  • Why do stablecoins carry a persisent sense of being "dangerous" or "ungovernable?
  • Are stablecoins truly private money? How do...


Jun 5, 2026

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

  • FIFA’s World Cup ticketing scandal
  • Andrew Yang is now a crypto and telecoms entrepreneur
  • Are Strategy’s woes responsible for the Bitcoin pullback?
  • Will Saylor defend STRC or MSTR?
  • What are Saylor’s options here?
  • Polymarket has another...


May 29, 2026

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

  • The CEO of Lead bank says debanking was made up
  • Which aspects of debanking were real?
  • The SEC scraps its 50-year-old gag rule
  • The WSJ gets free banking history wrong in their attack on stablecoins
  • What does history tell us about decentralized...


May 22, 2026

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

  • Are AI datacenters better or worse for the environment than Bitcoin miners?
  • AI is not responsible for your power bills
  • Why AI could actually drive down residential power prices
  • Is AI less popular than crypto ever was?
  • The negative societal...