On The Brink with Castle Island

Castle Island Ventures
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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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Nov 3, 2025 • 39min

Giovanni Vignone (Octane Security) on Protecting Onchain Assets (EP.682)

Giovanni Vignone, founder of Octane Security and a crypto security expert, dives into the evolving landscape of cybersecurity in the cryptocurrency space. He discusses the major threats hackers pose today and how teams can improve their security practices from day one. Giovanni emphasizes the importance of continuous vulnerability analysis, budget recommendations for startups, and the role of AI in both scaling attacks and defenses. He also highlights the risks of centralization and how effective security spending can prevent costly breaches.
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Oct 31, 2025 • 38min

Weekly Roundup 10/31/25 (DATs selling coins, prediction market problems, Bessent's pesos) (EP.681)

This week, the hosts dive into Mastercard's $2 billion acquisition of Zerohash and Fiserv's staggering stock drop, hinting at regional banking pressures. They explore Bitwise's Solana staking ETF launch and question the fate of DATs amid asset sales. A discussion on the questionable legality of prediction markets leads to insights about the structural challenges they face. The hosts also reflect on historical financial crises, Scott Bessent's savvy peso trade, the crisis in Venezuela, and revisit the Iran-Contra scandal.
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Oct 29, 2025 • 19min

Geetha Panchapakesan (Tesser) on Enabling FIs to Utilize Stablecoins (EP.680)

Geetha Panchapakesan, founder and CEO of Tesser, has nearly 20 years of experience in the payments sector, having worked with industry giants like Mastercard and PayPal. She discusses the transformative role of stablecoins in enabling financial institutions to streamline payments. Geetha highlights the challenges banks face and how Tesser's all-in-one solution addresses issues like custody and treasury efficiency. Regulatory shifts, particularly the GENIUS Act, also pave the way for enhanced stability in stablecoin engagement.

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