On The Brink with Castle Island

Castle Island Ventures
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24 snips
Dec 19, 2025 • 42min

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

Expect intriguing rumors about exchange insolvency and the implications of Caroline Ellison's sentencing. Dive into the regulatory landscape with discussions on the Fed's rescinded guidance and VISA's stablecoin endeavors. Delve into the potential threats of quantum computing to Bitcoin and whether forks are becoming obsolete. Plus, explore the year's predictions for digital assets and some light-hearted chats about UFOs and the Dark Forest concept. A mix of serious analysis and whimsical speculation awaits!
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Dec 17, 2025 • 39min

Corn (Yearn Finance) on the Evolution of DeFi Protocols (EP. 691)

Dive into the evolution of DeFi with insights on how the TerraLuna crash reshaped the market. Discover the changing landscape of incentive mechanisms and the role of risk curators in this dynamic world. Corn highlights the collapse of xUSD, the implications of on-chain cybersecurity, and the appetite for DeFi among non-crypto users. Explore the nuances of token value models, the push for verifiable yields, and the tension between centralization and decentralization in the future of financial protocols.
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13 snips
Dec 12, 2025 • 38min

Weekly Roundup 12/12/25 (Do Kwon sentenced, DTC no action letter, Circle's private stablecoin) (EP.690)

Matt and Nic dive into the fallout from Do Kwon's sentencing, exploring the implications for crypto credibility. They discuss the DTC's no-action letter that clarifies regulations for tokenized securities and the launch of Circle's privacy-focused stablecoin, USDCX. The duo weighs in on the future of Web3 and reflects on the surprising stance of the teachers union against a key market structure bill. They also share insights on recent fundraising successes and the challenges posed by oracle mishaps in prediction markets.
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24 snips
Dec 5, 2025 • 34min

Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)

Quantum risks loom over Bitcoin, raising questions about Taproot's vulnerability. The hosts dissect MicroStrategy's dollar reserve tactics and the troubling state of digital asset trusts. Prediction markets face scrutiny, especially with concerns of insider trading on platforms like Polymarket. Regulatory actions heat up as Vanguard embraces crypto ETFs. The episode wraps with alarming discussions about AI's potential to exploit crypto vulnerabilities and the need for enhanced security measures.
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9 snips
Dec 1, 2025 • 33min

Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)

Stepan Simkin, the founder of Squads and creator of Altitude, shares insights on stablecoin-powered financial services. He discusses the evolution of Squads to meet the asset treasury needs of businesses, particularly small to medium-sized ones. Stepan highlights the growing trend of businesses moving towards USD stablecoins for safe yield opportunities and streamlined payroll processes. He also explores how local banks might react to these changes, predicting a future dominated by fintech innovators while traditional banks struggle to adapt.
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11 snips
Nov 28, 2025 • 28min

Weekly Roundup 11/27/25 (Who we are thankful for, S&P downgrades Tether) (EP.687)

Get ready for Thanksgiving banter about deep-fried turkeys and holiday traditions. Discover the latest in fintech with Klarna's stablecoin launch and the legal maze surrounding prediction markets. Hear insights on Upbit's substantial hack and S&P's downgrade of Tether. The hosts also dive into Robinhood's move into prediction markets and the competitive landscape for payment giants like Visa and Mastercard. Plus, a heartfelt segment on those they're thankful for this year enhances the holiday spirit.
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Nov 21, 2025 • 39min

Weekly Roundup 11/21/25 (Quantum FUD, DAT hangover, stablecoin duration risk) (EP.686)

This week, the hosts dive into the intriguing worries surrounding quantum computing's potential impact on Bitcoin, sparking sell-offs and market panic. They analyze the ongoing effects of a recent flash crash while exploring whether the U.S. government could seize Satoshi's coins amid quantum risk. The guys also discuss stablecoin duration risks and contemplate a possible bailout for AI. Additionally, they touch on institutional Bitcoin holdings and speculate on the future of NFTs. Get ready for a whirlwind of crypto news and debates!
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15 snips
Nov 14, 2025 • 34min

Weekly Roundup 11/14/25 (Miran speech, Cash App adds Stables, DAT Hangover)(EP.685)

This week covers a range of hot topics in the crypto world. A key discussion revolves around Fed Governor Stephen Miran's stablecoin speech and its implications for monetary policy. Coinbase's move out of Delaware raises eyebrows, alongside the fallout from their failed acquisition of BVNK. Visa's support for stablecoins and the Czech Republic's Bitcoin purchase add to an evolving financial landscape. Plus, debates on CBDCs and their potential impact on stablecoins shed light on the future of digital currencies.
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Nov 7, 2025 • 37min

Weekly Roundup 11/07/25 (Balancer hack, DATs are suffering, Zcash rally) (EP.684)

Matt and Nic dive into the latest crypto news, sparking a lively debate over Tom Brady's cloned dog. They discuss Balancer's $128M hack due to a smart contract error, pointing out the need for better security measures in DeFi. The duo examines the recent rally in Zcash, attributing it to privacy upgrades and market interest. They also explore the impact of a government shutdown on market liquidity and question if stablecoins might be the pivotal innovation that could transform the crypto landscape.
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9 snips
Nov 5, 2025 • 21min

Keone Hon (Monad Foundation) on Blockchains Built to Scale (EP.683)

Keone Hon, founder of the Monad Foundation and an expert in high-frequency trading, dives into the future of on-chain finance. He explores how blockchains can revolutionize financial systems by 2025 and discusses Monad's unique architecture designed for high throughput and low-latency finality. Keone also sheds light on the importance of decentralization during market instability, the role of Auto-Deleveraging, and what success looks like for Monad in a few years. Plus, he shares insights on building a dynamic, entrepreneurial team to tackle these challenges.

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