

On The Brink with Castle Island
Castle Island Ventures
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
Episodes
Mentioned books

15 snips
Aug 22, 2025 • 39min
Weekly Roundup 08/22/25 (SALT Jackson Hole, Wyoming Stable Token, Fed drama) (EP.659)
This week dives into a bear encounter during a mountain run, offering a lighthearted spin on a wild experience. Key highlights from the Jackson Hole conference include Eric Trump's bold Bitcoin predictions amidst critical Fed discussions. Wyoming's innovative stablecoin initiative takes center stage, while questions arise around Digital Asset Treasuries and their market implications. The conversation tackles legal responsibilities of developers, exploring the complexities of decentralized finance and the potential impact of jury trials in the digital age.

Aug 21, 2025 • 27min
Cupid & Hercules (Groom Lake) on Preventing and Responding to Cybercrime (EP.658)
Wyatt chats with the founders of Groom Lake, diving into the intricate world of cybersecurity in the crypto realm. They discuss how social engineering attacks target crypto companies and emphasize the importance of employee education. The conversation highlights strategies like Multi-Factor Authentication and routine audits for enhancing security. Listeners learn about the urgency of addressing potential account compromises and the Reaper platform for monitoring data leaks. Proactive measures and a strong organizational culture are key for elevating cybersecurity standards.

18 snips
Aug 18, 2025 • 30min
Luke Xie (SatLayer) on The Next Generation of Bitcoin Yield (EP.657)
Luke Xie, cofounder of SatLayer and an expert in Bitcoin and DeFi, dives into the intriguing landscape of Bitcoin's financial evolution. He discusses how Bitcoin's unique role in decentralized finance is growing, addressing its comparative downside in total value locked against other assets. Luke explores innovative yield strategies and the potential for Bitcoin as a global reserve currency. Additionally, he examines the cultural factors shaping Bitcoin adoption and the future of instant payments, revealing the exciting possibilities of Bitcoin-backed financial products.

11 snips
Aug 15, 2025 • 39min
Weekly Roundup 08/15/25 (DAT fine print, stablecoin L1s, banks vs stables) (EP.656)
Join Matt and Nic as they dive into the latest in crypto, discussing the nuances of Digital Asset Tokens and their market implications. Hear about Stripe and Circle's new stablecoin Layer 1s and the irony surrounding Stripe's entry. Reflect on Do Kwon's plea deal, the potential fallout of a 51% attack on Monero, and complaints about stablecoin yields. They also explore the challenges of traditional banks in adapting to the evolving landscape of digital assets while sharing a light-hearted take on breakfast cereals along the way.

Aug 13, 2025 • 32min
Huf Haus (Pear Protocol) on Trading Strategies Across Crypto Cycles (EP.655)
Huf Haus, founder of Pear Protocol, has a strong background in traditional financial markets, focusing on trading strategies. He explores the intriguing world of pair trading and its benefits in volatile crypto markets. The conversation highlights innovative strategies like volatility selling and basket trading, delving into the complexities of funding rates. Huf also discusses how AI is transforming trading efficiency and emphasizes the importance of adapting methods to tackle market inefficiencies. The impact of privacy for institutional traders and the evolution of trading platforms adds to the rich discussion.

17 snips
Aug 11, 2025 • 30min
Nathan McCauley on Anchorage Digital Prime and Stablecoin White-Label (EP.654)
Nathan McCauley, Founder and CEO of Anchorage, discusses the transformative impact of the Genius Act on the digital asset industry. He unveils Anchorage’s white-label stablecoin issuance platform and explores its role in enhancing trade execution and custody services. McCauley highlights the evolving market structure and regulatory landscape, including the implications for financial institutions and the future of stablecoins. With insights on geopolitical impacts and investment strategies, he paints a vivid picture of the challenges and opportunities in modern finance.

12 snips
Aug 8, 2025 • 40min
Weekly Roundup 08/08/25 (Debanking EO, Storm Verdict, RMB stables) (EP.653)
Dive into the chaos of NYC's sanitation struggles and China's relentless Bitcoin bans. Discover if China is truly launching an RMB stablecoin and ponder the implications of Trump’s debanking executive order. Explore OpenAI's release of GPT-5 and debate the future of AGI. Unpack SEC updates on liquid staking tokens and the need for financial privacy amid growing surveillance. Plus, consider the potential of stablecoins to revolutionize banking and whether AI could finally unmask Satoshi Nakamoto.

Aug 4, 2025 • 39min
Sid Powell (Maple) on Maple's Comeback & DeFi Credit Markets (EP.652)
Sid Powell, CEO and co-founder of Maple Finance, shares insights on Maple's remarkable rebound in the DeFi space. He discusses the evolution from centralized credit services to on-chain asset management and the challenges faced during the 2022 crypto credit crisis. Powell emphasizes the importance of resilience and innovative strategies. The conversation also highlights the benefits of stablecoin lending for trading firms and the transformative potential of decentralized finance over traditional markets.

Aug 1, 2025 • 31min
Weekly Roundup 08/01/25 (SEC’s Project Crypto, In-kind ETFs, White House report) (EP.651)
Matt and Nic dive into significant developments in cryptocurrency, including a groundbreaking White House report that highlights the government's interest in digital assets. They discuss SEC Chair Paul Atkins' pivotal speech, emphasizing a shift towards embracing tokenized securities and DeFi. The rise of stablecoins takes center stage, along with exciting news on Bitcoin ETFs and JPMorgan's expanding collaboration with Coinbase. The tech world isn't left out, with Figma's successful IPO and insights into how AI is reshaping design.

14 snips
Jul 28, 2025 • 46min
Michael Bentley (Euler) on Euler's Comeback (EP.650)
Michael Bentley, founder of Euler, shares his journey in the crypto world, navigating the complexities of decentralized lending. He recounts Euler's inspiring comeback after a massive $200 million security breach, highlighting the importance of team resilience and personal relationships in a pseudonymous culture. Bentley discusses the balance of innovation and risk in crypto, the lessons of navigating public perception, and the challenges of combining work and family life in a demanding industry. His insights reveal the vital role of interpersonal connections in shaping success.