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On The Brink with Castle Island

Castle Island Ventures
On The Brink with Castle Island
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735 episodes

  • On The Brink with Castle Island

    Weekly Roundup 06/19/26 (STRC under pressure, Illinois' crypto tax, Open weight AI vs the AI boom) (EP.726)

    19/06/2026 | 38 mins.
    Matt and Nic are back for a week of news and deals. In this episode: 
    The Tartan Army takes over Boston
    Europeans are shocked that American infrastructure works
    STRC falls into the low $80s
    STRC's liquidation cascade mechanics
    What are Saylor's options now?
    Is the US right to put the brakes on Fable?
    Will open weight models puncture the AI boom?
    Are we living in a vulnerable world?
    Kristin Gillebrand's son raises $30m for a perps exchange
    Make sure your tokenized equity provider has the equity
    Why aren't publishers doing pay per content
    Content mentioned:
    Nick Bostrom, The Vulnerable World Hypothesis
  • On The Brink with Castle Island

    Weekly Roundup 06/12/26 (Strategy survives, Zcash Orchard bug, the thin model hypothesis) (EP.725)

    12/06/2026 | 38 mins.
    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 inflation bug
    SBF formally applies for a Presidential pardon
    The CFTC proposes banning a subset of prediction market contracts
    Polymarket thinks that Kalshi is spying on them
    European fans in America for the World Cup are discovering Buc-ees
    The DATs are struggling
    Hester Peirce gives her farewell address
    Japanese banks are launching a joint stablecoin
    Will there be offshore interest-bearing USD stablecoins?
    Anthropic drops Fable 
    The thin model hypothesis
    What could pop the AI rally?
  • On The Brink with Castle Island

    Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724)

    09/06/2026 | 1h 3 mins.
    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 we define private money?
    Who owns our current banking and payment systems?
    Why do banks vocally oppose stablecoins?
    Who will own and control digital money networks?
    Are blockchains the right medium for digital finance over the long term?
    Is digital trust a problem?
  • On The Brink with Castle Island

    Weekly Roundup 06/05/26 (MSTR wobbles, Polymarket's MSTR market, Andrew Left convicted) (EP.723)

    05/06/2026 | 32 mins.
    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 market resolution SNAFU
    How UMA could be used to exploit Polymarket
    BitMine considers a perpetual preferred security
    Google's quantum circuit is optimized by hobbyists
    Galaxy launches OTC trading for prediction markets
    Treasury sanctions Iran's largest digital asset exchanges
    Andrew Left of Citron research is convicted of securities fraud
  • On The Brink with Castle Island

    Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland) (EP.722)

    29/05/2026 | 43 mins.
    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 monetary issuance
    Why stablecoins aren't vulnerable to the same issues as free banks
    SoFi launches SoFiUSD and mixes a stablecoin with a tokenized deposit
    Sentiment is bottoming in Ethereum
    David Hoffman sells his ETH
    Are stablecoins parasitic to L1s
    Can L1s accrue value sustainably?
    The DATs are troubled
    Is AGI here already?
    AI cost discipline
    Content mentioned in this episode: 
    Nic on Substack, Stablecoins are private money. There's nothing wrong with that
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About On The Brink with Castle Island
Hosts Matt Walsh and Nic Carter of Castle Island Ventures explore news and deals in the public blockchain space and talk to some of the leading experts in the industry. Learn more and stay up to date at CastleIsland.vc and follow on twitter @CastleIslandVC
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