On The Brink with Castle Island – Details, episodes & analysis

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On The Brink with Castle Island

Castle Island Ventures

Business

Technology

Frequency: 1 episode/3d. Total Eps: 740

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

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https://onthebrink.link/withum
52 shares
https://coinmetrics.io/
48 shares
https://onthebrink.link/fireblocks%20
26 shares

https://twitter.com/CopperHQ
12 shares
https://twitter.com/castleislandvc
6 shares
https://twitter.com/DTAPCAP
5 shares

https://medium.com/@nic__carter/the-status-of-proof-of-reserve-as-of-year-end-2022-48120159377c
2 shares
https://medium.com/@nic__carter/redeem-and-retain-nfts-are-the-future-of-luxury-goods-760f00dbce23
2 shares
https://medium.com/@sean.m.judge/reasons-to-remain-bullish-after-a-year-in-crypto-hell-74d6807cc408
2 shares

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Score global : 42%

Publication history

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Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)

Episode 689

Friday, December 5, 2025 • Duration 33:39

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

Quantum risk again
Are banks filled with spooks?
The trouble with Taproot addresses
Microstrategy's dollar reserve
Kalshi is going on chain
Prediction market predicaments
Are insiders monetizing Google search information on Polymarket?
Are prediction markets insider trading machines by definition?
DAT activist fights
Vanguard adds Bitcoin ETFs
House Financial Services Committee releases their final report on OCP2.0
What's going on with leverage in crypto?
Are AI agents going to start stealing crypto?
Is Eliezer Yudkowski to be trusted?
AI is going to usher in the golden age of fraud

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Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)

Episode 688

Monday, December 1, 2025 • Duration 33:01

Stepan, founder of Squads, sits down with Wyatt on today's episode. In this discussion:

Squads' evolution from a DeFi-facing product to servicing a broader range of companies' asset treasury needs.
What are the pain points of local small-medium businesses?
What is driving the gradual global movement from local currencies into USD stablecoins?
The appetite for safe yield across user types.
Other traditional digital banking players and how they are evolving with technology.
How the stablecoin trend impacts governments.
What happens to local banks?

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Weekly Roundup 10/24/25 (Quantum, Crypto Pardons, Fed Payment Accounts) (EP.679)

Episode 679

Friday, October 24, 2025 • Duration 34:07

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

Old fashioned crime is back
Quantum risk to Bitcoin
More outcry in Washington over the Democratic edits to market structure
CZ gets a presidential pardon
Federal Reserve announces a payments charter

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Weekly Roundup 01/10/24 (FDIC Pause Letters released, SEC v Coinbase) (EP.589)

Episode 589

Friday, January 10, 2025 • Duration 38:37

Matt and Nic are back after a week off. In this episode:

Southern District of New York grants Coinbase's appeal in their case against the SEC
The Governor of the Czech national bank is considering Bitcoin in their reserves
Do Kwon is extradited to the US
E-trade is launching crypto trading
The FDIC is forced by a court to further un-redact documents Coinbase asked for in a FOIA request
We cover the FDIC's Pause Letters

Content mentioned in this episode:

Fidelity Digital Assets, 2025 Look Ahead
Bitwise, Benchmark Survey of Financial Advisor Attitudes Toward Crypto Assets
Nick Anthony, Fair Access to Banking

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Dana Syracuse and Josh Boehm (Paul Hastings LLP) on the 2025 Digital Asset Legal Landscape (EP.588)

Episode 588

Thursday, January 9, 2025 • Duration 38:37

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

The common legal and regulatory considerations that are encountered by companies in the digital asset industry.
Common pitfalls that entrepreneurs in this ecosystem should avoid.
The state of the stablecoin industry and the regulatory considerations in this category.
Potential changes ahead in 2025 on how digital assets are regulated in the United States.

To learn more about Paul Hastings and their fintech and digital asset practices visit www.paulhastings.com

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Weekly Roundup 12/27/24 (Tether x Rumble, quantum threat, End of year predictions) (EP.587)

Episode 587

Friday, December 27, 2024 • Duration 38:27

Matt and Nic are back for an end of year episode. In this episode:

Tether invests $775m in Rumble
Who are the Rumble shareholders in Trump's admin?
Microstrategy seeks approval for more Bitcoin buying
We review the quantum risk to Bitcoin
Matt and Nic's predictions for 2025

Sponsor notes:

Coin Metrics, State of the Network's 2024 Year in Review
In Coin Metrics State of the Network Issue 291, we revisit major stories that shaped the digital asset industry in 2024 with a data-driven lens

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Janusz and Red (Bitcoin Layers) on Bitcoin Season 2 (EP.586)

Episode 286

Wednesday, December 25, 2024 • Duration 31:05

Janusz and Red from Bitcoin Layers join the show. In this episode:

Innovation on Bitcoin, previously and now
Technology vs consumer adoption
The future of BTC use cases

More about Bitcoin Layers

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Weekly Roundup 12/20/24 (No SBR?, Prometheum, Crenshaw) (EP.585)

Episode 585

Friday, December 20, 2024 • Duration 43:36

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

Nic comes out against the SBR on Bloomberg
More Prometheum nonsense
MicroStrategy acquired an additional 15,350 BTC for roughly $1.5 billion, bringing the company's total holdings to 439,000 BTC. Microstrategy was also added to the Nasdaq 100 this week, which will lead to the stock's inclusion in several large ETFs including Invesco's QQQ.
Anchorage Digital has received New York BitLicense approval, enabling them to offer digital asset custody and trading services to more customers in the state such as RIAs and other institutional asset managers.
The US Senate scrapped a vote to renominate SEC Commissioner Caroline Crenshaw in response to immense backlash from the crypto community, led by Coinbase-backed non-profit Stand With Crypto, for Commissioner Crenshaw's treatment of the digital asset industry.
A Texas state representative, Giovanni Capriglione, introduced a bill for the state to create a strategic Bitcoin reserve.
Riot Platforms, the publicly traded Bitcoin miner, acquired 667 BTC this week for $67.4 million to add to their balance sheet, bringing their total holdings to 17,429 BTC.

Alex Lin (Reforge) on On-chain Innovation & Consumer Use Cases (EP.584)

Episode 584

Wednesday, December 18, 2024 • Duration 31:50

Wyatt sits down with Reforge VC's Alex Lin. In this episode:

Alex's interdisciplinary road into crypto
Innovation in blockchain infrastructure
Crypto-powered consumer applications

Learn more about Reforge, a blockchain and frontier tech investment firm.

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Rodrigo Seira (Cooley) and Ron Hammond (Blockchain Association) on Digital Asset Policy in 2025 (EP.583)

Episode 583

Monday, December 16, 2024 • Duration 39:40

Rodrigo Seira, Special Counsel at Cooley and Ron Hammond, Director of Government Relations at The Blockchain Association join the show. In this episode we discuss:

The 2024 election and the impact of the crypto vote.
Executive branch actions to keep an eye on in 2025.
Potential SEC related actions that would impact the digital asset market.
The future of Staff Accounting Bulletin 121.
Where digital asset legislation fits into the 2025 legislative priorities.
Stablecoin legislation.
Market structure legislation.

On The Brink with Castle Island – Details, episodes & analysis

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On The Brink with Castle Island – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

Other99+

Twitter99+

Medium29

RSS feed quality and score

Publication history

Latest published episodes

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Apple Podcasts

Spotify

Related Shows Based on Content Similarities

Other99+

Twitter99+

Medium29