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

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On The Brink with Castle Island

On The Brink with Castle Island

Castle Island Ventures

Business
Technology

Frequency: 1 episode/3d. Total Eps: 697

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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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Score global : 48%


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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

vendredi 5 décembre 2025Duration 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

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

Episode 688

lundi 1 décembre 2025Duration 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?

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

Episode 679

vendredi 24 octobre 2025Duration 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 

 

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

Episode 589

vendredi 10 janvier 2025Duration 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: 

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

Episode 588

jeudi 9 janvier 2025Duration 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

 

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

Episode 587

vendredi 27 décembre 2024Duration 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: 

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

Episode 286

mercredi 25 décembre 2024Duration 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

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

Episode 585

vendredi 20 décembre 2024Duration 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.
  • The NFT collection CyberKongz announced they had received a Wells Notice from the SEC.
  • A California judge sided with Coinbase in a suit brought by BiT Global over the exchange's delisting of wBTC. Coinbase had recently moved to remove the asset, a tokenized version of BTC tradeable on Ethereum-based networks, following BiT Global, a custodian closely affiliated with Tron founder Justin Sun, assuming custody services for wBTC.

Sponsor notes: 

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

Episode 584

mercredi 18 décembre 2024Duration 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.

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

Episode 583

lundi 16 décembre 2024Duration 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.

To learn more about Cooley visit:

www.cooley.com

To learn more about The Blockchain Association visit:

www.theblockchainassociation.org


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