
On The Brink with Castle Island
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
Latest episodes

20 snips
Mar 12, 2025 • 42min
Jeff Park (Bitwise) on Digital Asset Alpha Strategies (EP.602)
Jeff Park, Head of Alpha Strategies at Bitwise Asset Management, shares his extensive expertise in digital asset investment strategies. He highlights the latest innovations at Bitwise, including effective yield strategies and the role of stablecoins in the market. The conversation dives into the evolving landscape of Bitcoin yield generation and how companies like MicroStrategy are strategically adopting Bitcoin on their balance sheets. Listeners will also gain insights into the regulatory challenges and future opportunities within the crypto space.

4 snips
Mar 10, 2025 • 40min
Brandon Mulvihill (Crossover Markets) on the future of market structure in the USA (EP.601)
Brandon Mulvihill, co-founder and CEO of Crossover Markets, discusses the future of market structure in the U.S. crypto landscape. He explores how banks are adapting to regulatory changes and the emerging competition among exchanges. The conversation highlights the potential of Electronic Communication Networks for price discovery and the role of traditional institutions in the crypto space. Mulvihill also shares insights on Crossover’s growth plans, including integrating AI to enhance trading efficiency and liquidity by 2025.

Mar 7, 2025 • 35min
Weekly Roundup 03/07/25 (Crypto Reserve, Debanking Bill, Broker Rule) (EP.600)
Engaging discussions unravel the potential implications of a U.S. crypto reserve, pondering whether Bitcoin should dominate or co-exist with altcoins. The SEC's growing involvement in crypto regulation is highlighted alongside pivotal developments in fundraising trends and market dynamics. Tensions bubble between major stablecoins like Tether and Circle in Washington. A scrutiny of entrepreneurial struggles amidst these market shifts adds a personal touch, while a whimsical debate on fasting and personal challenges offers a lighter contrast to the heavy crypto discussions.

Feb 28, 2025 • 36min
Weekly Roundup 02/28/25 (Bybit Hack, SEC drops lawsuits, bank-issued stablecoins) (EP.599)
This week, the cryptocurrency world faces shockwaves from Bybit's staggering $1.48 billion hack, marking the largest breach in history. Meanwhile, new regulations see the SEC abandoning lawsuits against major platforms like Coinbase and Robinhood. The debut of a yield-bearing stablecoin approved by the SEC raises eyebrows, as does Bank of America's potential entry into the stablecoin market. Additionally, MicroStrategy's bold Bitcoin investment and discussions around the implications of the Bank Secrecy Act on DeFi highlight the evolving landscape of finance.

Feb 21, 2025 • 31min
Weekly Roundup 02/21/25 (Milei’s Libra scandal, physical gold chaos, are memecoins dead?) (EP.598)
Milei's abrupt launch and abandonment of a Libra memecoin raises questions about the memecoin sector's future. Discussions delve into bipartisan support for a new stablecoin bill and the implications of evolving crypto regulations. The conversation shifts to the chaotic landscape of physical gold trading, contrasting it with Bitcoin's transferability. Interesting insights emerge on insider trading controversies and the potential of asteroid mining for future gold sources, all while addressing the shifting attitudes of younger generations towards these traditional assets.

Feb 14, 2025 • 29min
Weekly Roundup 02/14/25 (OCC and CFTC nominations, nation-state memecoins, Tigran retrospective) (EP.597)
Matt and Nic tackle significant news from the crypto world. They discuss key nominations for SEC and CFTC positions and the potential impact on regulations. The Central African Republic's launch of a meme coin stirs debate. They also reflect on Tigran Gambaryan’s story and explore the implications of a new stablecoin bill. Meanwhile, the gold market shows signs of strain, as tungsten gains traction amidst geopolitical tensions. Plus, is Vitalik making waves again? The hosts break down these hot topics with engaging insights.

Feb 13, 2025 • 30min
SEC Commissioner Hester Peirce on the journey ahead (EP.596)
Hester Peirce, SEC Commissioner and a champion for blockchain innovation, dives into the intricacies of digital asset regulation. She tackles the SEC's evolving policies and the risks they pose to technical innovation. The conversation highlights the necessity for clear regulations that bolster capital formation in the crypto space. Peirce also emphasizes the importance of transparency in token disclosures and the need for collaboration between regulators and innovators. Her insights provide valuable guidance for founders navigating this complex landscape.

Feb 11, 2025 • 35min
Nathan McCauley (Anchorage) on the evolving banking and custody landscape (EP.595)
Nathan McCauley, co-founder and CEO of Anchorage, delves into the dynamic banking landscape surrounding digital assets. He shares insights on the impactful evolution of Anchorage, highlighting the challenges of becoming a qualified custodian and the troubling trend of debanking for crypto startups. The conversation also covers the future of stablecoins, including the potential for a Global Dollar Network. Plus, McCauley discusses innovative tools like the Porto Wallet and Atlas, which aim to enhance self-custody and address institutional needs.

9 snips
Feb 7, 2025 • 36min
Weekly Roundup 02/07/25 (FDIC Files, House & Senate Hearings, SEC crypto priorities) (EP.594)
The hosts share hilarious skiing tales while unraveling serious crypto news. They dive into the Senate's hearings on debanking and regulatory challenges faced by the FDIC. Insights from Silvergate's liquidation provide a peek into banking dynamics. The Czech Republic's tax breaks for Bitcoin holders spark interest, alongside updates on the SEC's priorities for cryptocurrencies. As Ethereum navigates an identity crisis, the ambitious moves from MicroStrategy paint a vivid picture of the evolving crypto landscape.

Feb 5, 2025 • 47min
Mike Lempres on Silvergate’s Collapse, Bank Regulation, and Debanking (EP.593)
Mike Lempres, former Chairman of Silvergate Bank and a seasoned expert in banking regulation, dives deep into the collapse of the crypto-focused bank. He shares insights about the bank's growth and the significance of the Silvergate Exchange Network. Lempres reveals how Silvergate faced a devastating bank run following the FTX fallout and examines the implications of regulatory pressures that led to its liquidation. He also discusses the complex relationship between banks and crypto, exploring regulatory overreach and the future of debanking.