On The Brink with Castle Island

Henry sits down with Corn, head of business development at Yearn Finance, for a conversation about the evolution and current state of defi. In this episode: 

• The history of defi from 2020 to today, and how the TerraLuna crash impacted the market
• How incentive mechanisms in defi have changed in 2025
• What caused the collapse of xUSD and Stream Finance?
• What is the role of risk curators in defi?
• The state of onchain cybersecurity...

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

• CIV grows the team
• Nic does not regret 8 years in crypto
• People are getting blackpilled about crypto
• Does speculation in crypto have positive externalities?
• Matt has never seen LOTR
• Will web3 ever come back?
• The OCC lets banks broker crypto trades
• The Bitwise 10 lists
• Rushi Manche returns with a fund
• Circle is launching a private stablecoin
• The DTC gets a no act...

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 F...

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 pla...

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

• Is Quantum FUD causing Bitcoin to sell off?
• Ray Dalio is worry about Quantum
• Scott Aaronson is worried about quantum computing
• Vitalik is worried about quantum
• Quantum upgrade scenarios
• Are we still suffering from the flash crash?
• The DATs are selling
• DAT spot arbitrage
• Will the US government end up with the Satoshi coins
• Should the government bail out...

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

• The Senate Ag Cmte publishes a Market Structure draft
• Paul Atkins' token taxonomy speech
• Fed Governor Stephen Miran gives a major stablecoin speech
• Grayscale files their S-1
• Coinbase announces a tokensale platform
• Coinbase is leaving Delaware
• The Coinbase BVNK deal falls through
• Visa Direct adds stablecoin support
• The Czech republic buys Bitcoin
• DATs a...

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

• Tom Brady's clone dog
• We reminisce on the Nic Carter v Mike Green debate
• Is the government shutdown draining market liquidity?
• The trouble with Opendimes 
• Balancer hacked
• Stream finance's xUSD collapses
• DATs are selling coins
• Why is Zcash rallying?
• Are stablecoins the lightbulb of crypto

Content mentioned:

• JW Verret, Comment Letter to Trea...

Keone Hon, founder of the Monad Foundation joins the show. In this episode:

• From the point of view of Keone's trading background, what is the promise of blockchains?
• Reimagining financial systems with blockchains in 2025
• Why build Monad, and for anyone using a chain, why use Monad?
• How the importance of decentralization and chain efficiency becomes underscored during fragile market periods
• Auto-Deleveraging (ADL): What it is a...

Wyatt sits down with Giovanni Vignone, the founder of Octane Security, a crypto security platform focused on vetting application code pre-deployment. In this episode we discuss:

• What poses the greatest threat to crypto right now?
• How are hackers evolving?
• What are the important categories of crypto-facing cybersecurity?
• How much should startup teams be spending on security?
• How should teams think about counterparty risk?
• What ...

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

• Mastercard buys Zerohash for around $2b
• Fiserv has a catastrophic day
• Bitwise launches a Solana staking ETF
• Is there another regional banking crisis?
• EthZilla sold some ETH to buy back shares
• Will there be activists with the DATs?
• Are prediction markets structurally doomed?
• Sen Tillis introduces the Ensuring Fair Access to Banking act
• Could you go back and time a...

Geetha Panchapakesan, the founder and CEO of Tesser, joins the show. In this episode: 

• Geetha's background in payments and how she arrived in stablecoins
• Major shifts across payments over Geetha's career
• Building a one-stop shop solution for financial i...

Dave Balter, the co-founder and CEO of Flipside Crypto joins the show. In this episode we discuss:

• How Flipside has shifted its product to fully harness the power of LLMs for analyzing public blockchain networks.
• Building a product organization in the age of A.I.
• Perspectives on the evolving landscape of laye...

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

• Will stablecoins drive deposit flight from the banks?
• Is FDIC insurance obsolete?
• Can CBDCs provide real privacy?
• ICE invests in Polymarket
• North Dakota is looking to issue their own "rough rider" stablecoin, joining Wyoming
• Luxembourg buys bitcoin out of their sovereign wealth fund
• Is the quantum bubble creating risks for Bitcoin?
• The "Salomon brother...

Pelle Braendgaard, the co-founder and CEO of Notabene joins the show. In this episode we discuss:

• Pelle's background and path to co-founding Notabene.
• The travel rule and how institutions achieve compliance for blockchain transactions.
• The launch of Notabene Flow, the first open stablecoin payments platform ...

Mike Cagney, the founder of Figure joins the show. In this episode we discuss:

• The process of taking Figure public in September 2025.
• The market structure for tokenized securities.
• Perspectives on the key issues being debated in the context of The Clarity Act.
• Reg NMS consideratio...