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On The Brink with Castle Island

Castle Island Ventures
Bitcoin
Stablecoins
Defi
Ethereum
Cryptocurrency
SEC
Blockchain
Coinbase
Digital Assets
Stable Coins
Stablecoin
Blockchain Technology
Microstrategy
Circle
Crypto Regulation
Binance
Tether
Tokenization
Quantum Computing
Solana

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

PublishesTwice weeklyEpisodes734Founded7 years ago
Number of ListenersCategories
InvestingTechnologyBusiness

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Artwork for On The Brink with Castle Island

Latest Episodes

Matt and Nic are back for a week of news and deals. In this episode:

• The Tartan Army takes over Boston

• Europeans are shocked that American infrastructure works

• STRC falls into the low $80s

• STRC's liquidation cascade mechanics

• What a... more

YouTube

Matt and Nic are back with a new week of news and deals. In this episode:

• Spanish soccer club Osasuna hedges their relegation on Kalshi

• Strategy shocks people by buying the dip

• Is Strategy sacrificing MSTR to save STRC?

• Saylor bolsters... more

YouTube

Wyatt sits down with Omid Malekan, a Professor at Columbia Business School, author of several books, and "Explainer-in-Chief" of blockchain technology. In this episode, Wyatt and Omid discuss:

• Why do stablecoins carry a persisent sense of being ... more

YouTube

Matt and Nic are back for another week of news and deals. In this episode:

• FIFA's World Cup ticketing scandal

• Andrew Yang is now a crypto and telecoms entrepreneur

• Are Strategy's woes responsible for the Bitcoin pullback?

• Will Saylor d... more

YouTube

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Recent Guests

Omid Malekan
Adjunct professor at Columbia Business School; blockchain thinker
Columbia Business School
Episode: Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724)
Gus Coldebella
Chief Legal Officer, Castle Island
Castle Island Ventures
Episode: Weekly Roundup feat. Gus Coldebella 05/15/26 (Clarity advances, Circle's Arc token) (EP.720)
Brandon Arvanaghi
Co-founder and CEO of Meow
Meow
Episode: Brandon Arvanaghi (Meow) on Banking AI Agents (EP.715)
Connor Dougherty
Co-founder and CEO of Valinor Digital
Valinor Digital
Episode: Connor Dougherty (Valinor) on the Evolution of Private Credit (EP.712)
Alex Wilson
Co-founder and co-CEO of Cyclops
Cyclops
Episode: Alex Wilson (Cyclops) on Crypto and Stablecoin Payment Solutions (EP.706)
Dana Syracuse
Partner at Paul Hastings, active lawyer on stablecoin licensing
Paul Hastings
Episode: Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius (EP.705)
Josh Boehm
Partner at Paul Hastings, experienced in governance and regulatory structuring for digital assets
Paul Hastings
Episode: Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius (EP.705)
Raj Parekh
Head of Stablecoins and Payments at Monad
Monad Foundation
Episode: Raj Parekh (Monad Foundation) on Stablecoins and The Next Era of Fintech (EP.702)
Bhavin Vaid
Co-founder of Birch Hill, focused on risk curation for digital assets
Birch Hill
Episode: Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700)

Hosts

Matt Walsh
Host, Castle Island Ventures partner known for crypto market analysis and policy-focused discussions
Nic Carter
Co-host, Castle Island Ventures partner bringing regulatory, governance, and market structure insights

Reviews

4.8 out of 5 stars from 567 ratings
  • Good fry

    the only vocal fry I’ll accept

    Apple Podcasts
    5
    Tom Tom 8
    Australia2 months ago
  • Found the most boring pod in bitcoin

    If you want to hear two guys rattle off ‘news’ about companies nobody cares about, this is your pod. Some company acquired another company - snooze. Another company raised some money - zzzzz. The hosts even sound half asleep, how is anyone else supposed to find this drivel interesting.

    Apple Podcasts
    1
    Ixzo
    United States7 months ago
  • Best Weekly Recap

    The insight and analysis from Matt and Nic is unmatched. I look forward to this recap every week. An absolute must listen. (Praying some terrorist turkey doesn’t take Matt out.)

    Apple Podcasts
    5
    jeromemichael888
    United States7 months ago
  • What happened to you being vocal about the “bad boys”??

    The way you’ve flipped the pancake on the bad actors in your industry and inability to call out the grift going on by the White House is hugely disappointing. CZ gets pardoned and you call this “controversial”?? Your listeners have longer memories.

    Apple Podcasts
    2
    notageek99
    United States8 months ago
  • Used to be good

    bleh

    Apple Podcasts
    4
    kfixbwhdisa
    United States10 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Insightful, no-nonsense crypto analysis with practical takeaways
Hosts mix policy with market context in a relatable way
Some listeners push back on political commentary or perceived bias
Consistent depth on regulatory developments and DeFi risk

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#144
France/Business/Investing
Apple Podcasts
#57
Argentina/Business/Investing
Apple Podcasts
#87
Ireland/Business/Investing
Apple Podcasts
#123
Russia/Business/Investing
Apple Podcasts
#140
Colombia/Business/Investing
Apple Podcasts
#141
Singapore/Business/Investing

Talking Points

Recent interactions between the hosts and their guests.

Brandon Arvanaghi (Meow) on Banking AI Agents (EP.715)
Q: What was the hardest part about just building out the product for the AI agents? Were there obstacles? How are agents different than humans in that respect?
The main challenges were prompt engineering and understanding the black-box behavior of models, which required heavy experimentation and close collaboration between engineers and AI systems to achieve reliable agent interactions and safe banking operations.
Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius (EP.705)
Q: Josh, what should entrepreneurs be thinking about as Genius rulemaking unfolds?
Josh emphasizes that startups should prepare for rulemaking by aligning with capital, AML, sanctions, and governance standards, while evaluating how stablecoin provisioning will adapt to the evolving framework and the potential for various charter types.
Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius (EP.705)
Q: Dana, starting with you, what type of companies are going this OCC path?
Dana explains that many firms are applying for OCC charters to enable banking-like activities for custody, purchase-sale of digital assets, and the use of a robust regulatory framework; she also notes that the environment has shifted toward seeking a clear set of rules.
Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700)
Q: What advice would you give to potential asset issuers of financial institutions who might be thinking about issuing an asset on-chain?
Vaid emphasizes the importance of efficiency within the asset issuance process, suggesting that institutions should focus on streamlining their operations rather than adopting practices that could lead to negative outcomes for retail investors.
Corn (Yearn Finance) on the Evolution of DeFi Protocols (EP. 691)
Q: What's the role and maybe the faults of the risk curators in some of these scenarios?
Corn explains that curators need to manage the risk within vaults, ensure sound collateral, and adapt to market demands, despite the overall business being challenging due to low profits.

Audience Metrics

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Frequently Asked Questions About On The Brink with Castle Island

What is On The Brink with Castle Island about and what kind of topics does it cover?

The show focuses on the intersection of crypto markets, regulation, and fintech infrastructure, with frequent deep dives into policy developments, DeFi risk, and the evolving role of traditional finance in digital assets. Hosts and guests unpack timely topics such as regulatory acts, stablecoins, cross-chain security, and the economics of crypto deals, often pairing rigorous analysis with pragmatic takeaways for builders, investors, and operators. Uniquely, episodes blend policy, market structure, and technical context with candid banter and postmortems from the industry's leading practitioners, offering actionable insights for listeners navigating a fast-moving space.

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1. Empire
2. Unchained
3. The Breakdown
4. Bankless
5. The Pomp Podcast

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On The Brink with Castle Island launched 7 years ago and published 734 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on On The Brink with Castle Island?

Recent guests on On The Brink with Castle Island include:

1. Omid Malekan
2. Gus Coldebella
3. Brandon Arvanaghi
4. Connor Dougherty
5. Alex Wilson
6. Dana Syracuse
7. Josh Boehm
8. Raj Parekh

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