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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
Microstrategy
Stablecoin
Blockchain Technology
Circle
Crypto Regulation
Tether
Quantum Computing
Artificial Intelligence
Decentralized Finance
Binance

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

PublishesWeeklyEpisodes754Founded7 years ago
Number of ListenersCategories
InvestingBusinessTechnology

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Latest Episodes

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

• Marathon Fusion says it has turned mercury into stable gold

• What would commercially viable alchemy mean for Bitcoin's scarcity argument?

• AI tools uncover a major vulner... more

YouTube

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

• The OCC publishes its debanking findings on America's largest banks

• Will the banks' fixes satisfy regulators?

• Google makes another advance in quantum error co... more

YouTube

Matt and Nic are back with more deals and news. In this episode:

• Is it appropriate to have AI manage your fantasy league?

• Quant firms are hiring "quals"

• Justin Drake scares everyone in crypto

• Did AI destroy math?

• Why a classical ECD... more

YouTube

Esther Wong, founder and CEO of Cashi joins the show. Cashi is a stablecoin spending app and cashback card with a global footprint. In this episode we discuss:

• Customer personas and use cases for stablecoin payments

• The future of tokenized eq... more

YouTube

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Recent Guests

Justin Drake
Ethereum researcher, co-author on quantum-related work
Cryptography/Blockchain field
Episode: Weekly Roundup 10/09/26 (Going Bunker Mode, classical ECC breaks, AI's math discoveries) (EP.744)
Yehuda Lindell
Cryptographer, Coinbase executive (head of cryptography)
Coinbase
Episode: Weekly Roundup 10/09/26 (Going Bunker Mode, classical ECC breaks, AI's math discoveries) (EP.744)
Esther Wong
Founder and CEO of Cashi
Cashi
Episode: Esther Wong (Cashi) on Making Stablecoins Spendable (EP.743)
Guy Young
Founder/representative of Athena
Athena
Episode: Weekly Roundup 09/04/26 (HuggingFace hack breaks containment, Hyperliquid onshoring, RSA260 factored, is the stablecoin sandwich cheaper?) (EP.738)
Christian Coller
Crypto industry professional
Episode: Weekly Roundup 08/21/26 (SALT Wyoming, SEC's Reg Crypto, Tether's big 4 audit, Crypto Privateers) (EP.735)
Chris Perkins
Crypto industry professional
Episode: Weekly Roundup 08/21/26 (SALT Wyoming, SEC's Reg Crypto, Tether's big 4 audit, Crypto Privateers) (EP.735)
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)

Hosts

Matt Walsh
Host of On The Brink; partner at Castle Island Ventures; regular host delivering market, policy, and deal-focused analysis.
Nic Carter
Co-host; partner at Castle Island Ventures; brings industry analysis, research-driven perspectives, and crypto journalism perspective to episodes.

Reviews

4.8 out of 5 stars from 571 ratings
  • Good content but ableist

    I like the podcast overall but was really disappointed to hear them rip into Dario Amodei, who clearly suffers from autism, for being "weird" while grimacing and stimming during his public appearance at the White House. I wish they would educate themselves and not tear others down out of ignorance.

    Apple Podcasts
    2
    Prnzzzzzx
    United States23 days ago
  • Good fry

    the only vocal fry I’ll accept

    Apple Podcasts
    5
    Tom Tom 8
    Australia6 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 Statesa year 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 Statesa year 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 Statesa year ago

Listeners Say

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

Deals section is particularly valued by listeners for actionable takeaways.
High praise for honest, skeptical coverage of crypto topics and governance.
Insightful, no-nonsense market analysis with useful context for investors.
Some episodes drift into politics; balance can feel uneven to critics.

Chart Rankings

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

Apple Podcasts
#102
Indonesia/Business/Investing
Apple Podcasts
#105
Colombia/Business/Investing
Apple Podcasts
#119
Russia/Business/Investing
Apple Podcasts
#135
Philippines/Business/Investing
Apple Podcasts
#244
Ireland/Business/Investing
Apple Podcasts
#247
Norway/Business/Investing

Talking Points

Recent interactions between the hosts and their guests.

Esther Wong (Cashi) on Making Stablecoins Spendable (EP.743)
Q: What drives your choice of stablecoins and how does Cashi approach regional differences in demand?
Cashi offers USDC and USDT and tailors to regional liquidity and supply patterns; USDT is more prevalent in some regions due to local liquidity sources, while USDC sees higher demand where liquidity and settlement ecosystems favor it; the user base is still early, so Cashi adapts to demand rather than pre-commit to a single coin.
Esther Wong (Cashi) on Making Stablecoins Spendable (EP.743)
Q: Tell us about Cashi and how you came to launch this business.
Cashi emerged from the need to simplify how people hold and spend stablecoins, leveraging Esther's background in payments and experience with Visa, MasterCard, and multi-currency cards to build a platform focused on easy on-ramps, fast settlement, and broad merchant adoption.
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.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
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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?

Two Castle Island Ventures hosts deliver a brisk, opinionated take on the week's crypto, DeFi, and tech policy news, pairing market analysis with candid commentary on deals, regulation, and security. Episodes balance hard-hitting security and governance topics with business moves, funding rounds, and regulatory dynamics, often weaving in practical takeaways for investors, builders, and operators. A standout angle is the hosts' venture-capital perspective combined with deep industry know-how, plus a recurring emphasis on self-custody, risk management, and the evolving interplay between crypto markets and policy.

Noteworthy traits include a consistent, no-nonsense delivery, thematic focus on both markets and policy, and a distinctive blend o... more

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On The Brink with Castle Island launched 7 years ago and published 754 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. Justin Drake
2. Yehuda Lindell
3. Esther Wong
4. Guy Young
5. Christian Coller
6. Chris Perkins
7. Omid Malekan
8. Gus Coldebella

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