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PODCAST

On The Brink with Castle Island

Castle Island Ventures

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

business investing

All Episodes

37:25

Weekly Roundup 01/02/26 (2026 predictions, wealth...

On The Brink with Castle Island ·

2026/01/02

Matt and Nic are back for the first OTB show of 2026. In this episode: Matt's ice rink adventures The House issues a draft of the PARITY Act The trouble with wealth taxes DATs continue to bleed out We talk about Nic's fiction story Predictions for 2026 Is there a secret exchange insolvency? What constitutes insider trading for prediction markets? Is the four year cycle finally over? Is it time to try socialfi again? Kickstarter snafus Content mentioned in this episode: Nic Carter, Trillion

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45:40

2025 Highlights and 2026 Predictions with Blockchain...

On The Brink with Castle Island ·

2025/12/30

Matthew Le Merle and Mitch Mechigian of Blockchain Coinvestors join the show. In this episode we discuss: The top 5 themes of 2025 for the blockchain industry 2026 predictions and key themes to monitor To learn more about Blockchain Coinvestors visit fifthera.com/blockchain

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42:20

Weekly Roundup 12/19/25 (Quantum FUD, CLARITY markup,...

On The Brink with Castle Island ·

2025/12/19

Matt and Nic are back for more deals and news. In this episode: Secret exchange insolvency rumors Caroline Ellison is free David Sacks says CLARITY is getting a markup The Fed rescinds their 2023 Novel Activities Supervision program Insolvent exchange prediction markets Visa's stablecoin advisory business JPM launches a tokenized Treasury fund MONY Quantum FUD Why Quantum might be a surprise Bitwise 2026 predictions The four year cycle is over Grabby aliens and the Dark Forest Content mentioned

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38:59

Corn (Yearn Finance) on the Evolution of DeFi...

On The Brink with Castle Island ·

2025/12/17

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 and recent hacks What is the appetite for defi from non-crypto users and

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37:34

Weekly Roundup 12/12/25 (Do Kwon sentenced, DTC no...

On The Brink with Castle Island ·

2025/12/12

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 action letter from the SEC to settle tokenized securities We do a Terra/Luna

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33:39

Weekly Roundup 12/05/25 (The trouble with Taproot, a...

On The Brink with Castle Island ·

2025/12/05

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

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33:01

Stepan Simkin (Squads) on Stablecoin-Powered...

On The Brink with Castle Island ·

2025/12/01

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

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28:09

Weekly Roundup 11/27/25 (Who we are thankful for, S&P...

On The Brink with Castle Island ·

2025/11/28

Matt and Nic record a special Thanksgiving episode of OTB. In this episode: What's the deal with deep fried turkeys? Polymarket gets CTFC approval Klarna is launching a stablecoin on Tempo Upbit is hacked Berachain drama Tether gets a downgrade from S&P Robinhood is spinning up their own prediction market with Susquehanna Are Visa and Mastercard moving fast enough? Who are we thankful for?

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38:41

Weekly Roundup 11/21/25 (Quantum FUD, DAT hangover,...

On The Brink with Castle Island ·

2025/11/21

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 AI? Will NFTs come back? IBIT is Harvard's largest 13F position David

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34:17

Weekly Roundup 11/14/25 (Miran speech, Cash App adds...

On The Brink with Castle Island ·

2025/11/14

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 are struggling CBDC holdouts Jack Dorsey bends the knee on stablecoins

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36:41

Weekly Roundup 11/07/25 (Balancer hack, DATs are...

On The Brink with Castle Island ·

2025/11/07

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 Treasury GENIUS ANPR

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21:15

Keone Hon (Monad Foundation) on Blockchains Built to...

On The Brink with Castle Island ·

2025/11/05

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 and why it is important. Where is there economic efficiency to be created

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38:47

Giovanni Vignone (Octane Security) on Protecting...

On The Brink with Castle Island ·

2025/11/03

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 do you wish early stage teams knew? Where is there room for improved

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37:50

Weekly Roundup 10/31/25 (DATs selling coins,...

On The Brink with Castle Island ·

2025/10/31

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 and trade effectively? Bessent's great peso trade What's going to happen

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19:07

Geetha Panchapakesan (Tesser) on Enabling FIs to...

On The Brink with Castle Island ·

2025/10/29

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 institutions, PSPs and MSBs Where FIs are today as it relates to engaging to stablecoins Regulatory tailwinds post-GENIUS See more attesser.xyz

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34:07

Weekly Roundup 10/24/25 (Quantum, Crypto Pardons, Fed...

On The Brink with Castle Island ·

2025/10/24

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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34:08

Weekly Roundup 10/17/25 (Flash crash, pig butchering...

On The Brink with Castle Island ·

2025/10/17

Matt and Nic are back with another week of news and deals. In this episode: We dissect the market structure behind the flash crash last week What happened with Binance and Ethena? Palmer Luckey’s de novo bank Erebor gets an OCC charter Paxos’ fat finger The US government has seized $15b in funds tied to pig butchering scams

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27:22

Pbj (Perpl) on the Perp DEX Market & Monad's Imminent...

On The Brink with Castle Island ·

2025/10/14

Wyatt sits down with Pbj, the founder of Perpl, a prominent perpetuals exchange on the imminently launching Monad blockchain. In this episode: How large are perp exchanges in the crypto market? Why perps are attractive to crypto users and traders Hyperliquid's success What assets would people trade on Perpl vs Hyperliquid? What makes Monad unique Perps for other asset classes? Reasons to be excited

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33:18

Dave Balter (Flipside) on the convergence of AI and...

On The Brink with Castle Island ·

2025/10/13

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 layer one and layer two blockchains. How the role of a data analyst will evolve in the coming years. Where Flipside is focusing its efforts within the blockchain data/analytics segment. To learn

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37:36

Weekly Roundup 10/10/25 (Luxembourg buys BTC, N....

On The Brink with Castle Island ·

2025/10/10

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 brothers" OP_RETURN dusting attack on old Bitcoins Reg NMS for blockchains

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