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On The Brink with Castle Island

Castle Island Ventures
Bitcoin
Web3
Ethereum
Coinbase
Decentralization
Blockchain Technology
Bitcoin ETF
Stablecoins
Cryptocurrency
Crypto
Capsule
CASA
Dynamic
Tether
Artificial Intelligence
Fileverse
Elizabeth Warren
Grayscale
Layer Two Roll-Ups
Fairshake PAC

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 weeklyEpisodes715Founded6 years ago
Number of ListenersCategories
TechnologyBusinessInvesting

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Latest Episodes

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

• What Dario Amodei and SBF have in common

• Trump wades in to the market structure debate and asks the banks to come to the table

• Why stablecoins are not like banks

... more

Alex Wilson, Co-Founder and CEO of Cyclops, joins the show. In this episode:

• Alex's background running The Giving Block and the company's acquisition by Shift4

• Difficulty in enabling stablecoin solutions when utilizing existing providers whil... more

Dana Syracuse and Josh Boehm of Paul Hastings join the show. In this episode we discuss:

• The OCC Charter process how digital asset companies are pursuing the federal path

• The aftermath of the Genius Act passage and the rulemaking process for ... more

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

• Kalshi has detected and banned two accounts for insider trading

• Is Polymarket going to have to add KYC?

• Is there a tradeoff between informational efficiency and m... more

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Recent Guests

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)
Stepan Simkin
Founder of Squads
Squads
Episode: Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)
Keone Hon
Co-founder of the Monad Foundation
Monad Foundation
Episode: Keone Hon (Monad Foundation) on Blockchains Built to Scale (EP.683)
Giovanni Vignone
Founder of Octane Security
Octane Security
Episode: Giovanni Vignone (Octane Security) on Protecting Onchain Assets (EP.682)
Scott Bessent
Noted currency trader involved in Argentine peso trading
Episode: Weekly Roundup 10/31/25 (DATs selling coins, prediction market problems, Bessent's pesos) (EP.681)

Hosts

Matt Walsh
Co-host of the podcast and Partner at Castle Island Ventures
Nic Carter
Co-host of the podcast and Partner at Castle Island Ventures

Reviews

4.8 out of 5 stars from 566 ratings
  • 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 States3 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 States3 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 States5 months ago
  • Used to be good

    bleh

    Apple Podcasts
    4
    kfixbwhdisa
    United States7 months ago
  • Used to be good

    Nic’s amoral embrace of all things AI strikes me as particularly soulless. And shameless. Very useful to him no doubt but on the human level, appalling. I am disgusted.

    Apple Podcasts
    1
    kfixbwhdisa
    United States9 months ago

Listeners Say

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

Criticism has emerged regarding the balance of topics covered, particularly around company news versus broader industry discussions.
There are mixed reviews on the direction of the content, with some listeners disappointed by occasional veering into political discussions.
The delivery and relationship between the hosts are frequently praised, with many listeners finding their chemistry engaging and entertaining.
Some listeners express a desire for a return to more focus on fundamental cryptocurrency topics rather than social commentary.
Listeners appreciate the deep insights and analysis provided by the hosts, often highlighting how they offer a unique blend of humor alongside serious topics.

Chart Rankings

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

Apple Podcasts
#250
Australia/Business/Investing
Apple Podcasts
#78
Argentina/Business/Investing
Apple Podcasts
#158
Indonesia/Business/Investing
Apple Podcasts
#180
Colombia/Business/Investing
Apple Podcasts
#194
Argentina/Business
Apple Podcasts
#195
Russia/Business/Investing

Talking Points

Recent interactions between the hosts and their guests.

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.
Corn (Yearn Finance) on the Evolution of DeFi Protocols (EP. 691)
Q: What's the history of DeFi protocols and how they've evolved through 2021 and all the craziness, and then maybe all the way up to today in your experience?
Corn shares that Yearn has maintained an open culture, evolving from being a new entity in DeFi with many contributors to having a more selective onboarding process as the industry has matured.

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?

This podcast features insightful discussions on the latest happenings in the blockchain and cryptocurrency industries. The hosts frequently cover significant news, trends, and deals, providing a comprehensive analysis on various topics such as stablecoins, regulatory changes, and technological advancements impacting the market. With a blend of humor and expert opinions, the content is both informative and engaging, appealing to listeners keen on understanding the evolving landscape of digital currencies and its implications for businesses and investments.

One noteworthy aspect is the inclusion of guest experts who share their insights and experiences, deepening the conversation around complex subjects like decentralized finance and tokeniz... more

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1. The Peter McCormack Show
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How many episodes of On The Brink with Castle Island are there?

On The Brink with Castle Island launched 6 years ago and published 715 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. Alex Wilson
2. Dana Syracuse
3. Josh Boehm
4. Raj Parekh
5. Bhavin Vaid
6. Stepan Simkin
7. Keone Hon
8. Giovanni Vignone

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