On The Brink with Castle Island

Castle Island Ventures

  • 42 minutes 20 seconds
    Weekly Roundup 12/19/25 (Quantum FUD, CLARITY markup, are forks obsolete?) (EP.692)

    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 launches a tokenized Treasury fund MONY
    • Quantum FUD
    • Why Quantum might be a surprise
    • Bitwise 2026 predictions
    • The four year cycle is over
    • Grabby aliens and the Dark Forest

    Content mentioned in this episode:

    19 December 2025, 11:00 am
  • 38 minutes 59 seconds
    Corn (Yearn Finance) on the Evolution of DeFi Protocols (EP. 691)

    Henry sits down with Corn, head of business development at Yearn Finance, for a conversation about the evolution and current state of defi. In this episode:

    • The history of defi from 2020 to today, and how the TerraLuna crash impacted the market
    • How incentive mechanisms in defi have changed in 2025
    • What caused the collapse of xUSD and Stream Finance?
    • What is the role of risk curators in defi?
    • The state of onchain cybersecurity and recent hacks
    • What is the appetite for defi from non-crypto users and institutions, and will a declining fed funds rate help?
    • How do defi protocols drive value to their native tokens?
    • How "decentralized" is defi today?

    17 December 2025, 8:18 pm
  • 37 minutes 34 seconds
    Weekly Roundup 12/12/25 (Do Kwon sentenced, DTC no action letter, Circle's private stablecoin) (EP.690)

    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 Bitwise 10 lists
    • Rushi Manche returns with a fund
    • Circle is launching a private stablecoin
    • The DTC gets a no action letter from the SEC to settle tokenized securities
    • We do a Terra/Luna restrospective
    • Terra's fatal mistake
    • Oracle mishaps on prediction markets
    • Why did the nation's largest teachers union come out against the Market Structure bill

    Content mentioned in this episode:

    12 December 2025, 11:00 am
  • 33 minutes 39 seconds
    Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)

    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 prediction markets insider trading machines by definition?
    • DAT activist fights
    • Vanguard adds Bitcoin ETFs
    • House Financial Services Committee releases their final report on OCP2.0
    • What's going on with leverage in crypto?
    • Are AI agents going to start stealing crypto?
    • Is Eliezer Yudkowski to be trusted?
    • AI is going to usher in the golden age of fraud
    5 December 2025, 11:00 am
  • 33 minutes 1 second
    Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)

    Stepan, founder of Squads, sits down with Wyatt on today's episode. In this discussion:

    • Squads' evolution from a DeFi-facing product to servicing a broader range of companies' asset treasury needs.
    • What are the pain points of local small-medium businesses?
    • What is driving the gradual global movement from local currencies into USD stablecoins?
    • The appetite for safe yield across user types.
    • Other traditional digital banking players and how they are evolving with technology.
    • How the stablecoin trend impacts governments.
    • What happens to local banks?
    1 December 2025, 5:55 pm
  • 28 minutes 9 seconds
    Weekly Roundup 11/27/25 (Who we are thankful for, S&P downgrades Tether) (EP.687)

    Matt and Nic record a special Thanksgiving episode of OTB. In this episode:

    • What's the deal with deep fried turkeys?
    • Polymarket gets CTFC approval
    • Klarna is launching a stablecoin on Tempo
    • Upbit is hacked
    • Berachain drama
    • Tether gets a downgrade from S&P
    • Robinhood is spinning up their own prediction market with Susquehanna
    • Are Visa and Mastercard moving fast enough?
    • Who are we thankful for?
    28 November 2025, 11:00 am
  • 38 minutes 41 seconds
    Weekly Roundup 11/21/25 (Quantum FUD, DAT hangover, stablecoin duration risk) (EP.686)

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

    • Is Quantum FUD causing Bitcoin to sell off?
    • Ray Dalio is worry about Quantum
    • Scott Aaronson is worried about quantum computing
    • Vitalik is worried about quantum
    • Quantum upgrade scenarios
    • Are we still suffering from the flash crash?
    • The DATs are selling
    • DAT spot arbitrage
    • Will the US government end up with the Satoshi coins
    • Should the government bail out AI?
    • Will NFTs come back?
    • IBIT is Harvard's largest 13F position
    • David Frum on stablecoins
    • Will stablecoins require a bailout?
    21 November 2025, 11:00 am
  • 34 minutes 17 seconds
    Weekly Roundup 11/14/25 (Miran speech, Cash App adds Stables, DAT Hangover)(EP.685)

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

    • The Senate Ag Cmte publishes a Market Structure draft
    • Paul Atkins' token taxonomy speech
    • Fed Governor Stephen Miran gives a major stablecoin speech
    • Grayscale files their S-1
    • Coinbase announces a tokensale platform
    • Coinbase is leaving Delaware
    • The Coinbase BVNK deal falls through
    • Visa Direct adds stablecoin support
    • The Czech republic buys Bitcoin
    • DATs are struggling
    • CBDC holdouts
    • Jack Dorsey bends the knee on stablecoins

    Content mentioned:

    14 November 2025, 11:00 am
  • 36 minutes 41 seconds
    Weekly Roundup 11/07/25 (Balancer hack, DATs are suffering, Zcash rally) (EP.684)

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

    • Tom Brady's clone dog
    • We reminisce on the Nic Carter v Mike Green debate
    • Is the government shutdown draining market liquidity?
    • The trouble with Opendimes
    • Balancer hacked
    • Stream finance's xUSD collapses
    • DATs are selling coins
    • Why is Zcash rallying?
    • Are stablecoins the lightbulb of crypto

    Content mentioned:

    7 November 2025, 11:00 am
  • 21 minutes 15 seconds
    Keone Hon (Monad Foundation) on Blockchains Built to Scale (EP.683)

    Keone Hon, founder of the Monad Foundation joins the show. In this episode:

    • From the point of view of Keone's trading background, what is the promise of blockchains?
    • Reimagining financial systems with blockchains in 2025
    • Why build Monad, and for anyone using a chain, why use Monad?
    • How the importance of decentralization and chain efficiency becomes underscored during fragile market periods
    • Auto-Deleveraging (ADL): What it is and why it is important.
    • Where is there economic efficiency to be created?
    • How has Keone gone about building a team to tackle this challenge?
    • What would make Monad "successful" in 2-3 years?
    5 November 2025, 4:54 pm
  • 38 minutes 47 seconds
    Giovanni Vignone (Octane Security) on Protecting Onchain Assets (EP.682)

    Wyatt sits down with Giovanni Vignone, the founder of Octane Security, a crypto security platform focused on vetting application code pre-deployment. In this episode we discuss:

    • What poses the greatest threat to crypto right now?
    • How are hackers evolving?
    • What are the important categories of crypto-facing cybersecurity?
    • How much should startup teams be spending on security?
    • How should teams think about counterparty risk?
    • What do you wish early stage teams knew?
    • Where is there room for improved security practices across the industry?
    3 November 2025, 5:31 pm
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