On The Brink with Castle Island

Castle Island Ventures
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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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9 snips
Oct 24, 2025 • 34min

Weekly Roundup 10/24/25 (Quantum, Crypto Pardons, Fed Payment Accounts) (EP.679)

This week dives into a wild mix of topics. Crime makes a comeback with insider NBA betting scandals and a daring jewel heist at the Louvre. Insights reveal how quantum computing could threaten Bitcoin's security. A controversial presidential pardon for a crypto CEO stirs political debates, while the Federal Reserve introduces a payments charter impacting fintech. Plus, major fundraises in the crypto world, including the launch of a new hedge fund, ramp up the stakes in digital assets. Don't miss the clash of crypto and AI policy discussions!
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12 snips
Oct 17, 2025 • 34min

Weekly Roundup 10/17/25 (Flash crash, pig butchering scam busted, Erebor charter granted) (EP.678)

This week dives into the aftermath of a flash crash triggered by tariff news and its effects on crypto markets. The hosts dissect Binance's role and the auto-deleveraging phenomenon that intensified the selloff. They highlight the alarming $15 billion Bitcoin seizure linked to pig butchering scams, shedding light on the human cost behind these scams. The conversation also touches on the recent approval of Erebor’s OCC charter and the potential impact of new crypto banks on traditional finance, raising questions about regulatory dynamics.
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12 snips
Oct 14, 2025 • 27min

Pbj (Perpl) on the Perp DEX Market & Monad's Imminent Launch (EP.677)

Delve into the booming world of perpetual exchanges as the founder of Perpl shares insights on their allure for retail traders. Discover how derivatives dominate crypto trading volumes and the innovative strategies behind Hyperliquid's success. The discussion highlights Monad's unique features and potential for broad asset classes, while examining trading behavior across desktop and mobile. Learn about the exciting future of on-chain trading and how it could transform access to traditional markets.
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11 snips
Oct 13, 2025 • 33min

Dave Balter (Flipside) on the convergence of AI and Blockchain Analytics (EP.676)

Dave Balter, co-founder and CEO of Flipside Crypto, dives into the fascinating intersection of AI and blockchain analytics. He shares how Flipside is leveraging AI to transform data workflows, empowering analysts with partner-level insights. Balter discusses the urgent need for real-time on-chain data versus traditional finance delays, and how AI analytics can drastically reduce time-to-outcome. He also explores the challenges of balancing real users against bots on blockchains and the evolution of successful strategies in this rapidly changing landscape.

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