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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

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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40:45

Pelle Braendgaard on the Notabene Flow payments...

On The Brink with Castle Island ·

2025/10/08

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 enabling pull payments for businesses. Views on the evolving market structure for stablecoin payments The state of digital identity. To learn more about Notabene visit notabene.id and follow

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36:50

Mike Cagney (Figure) on Blockchain Capital Markets...

On The Brink with Castle Island ·

2025/10/07

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 considerations for blockchain assets. The impact of stablecoins on the banking sector. The original thesis of Figure and the attractiveness of the HELOC market. The Provenance Blockchain Competition versus legacy financial services

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33:57

Weekly Roundup 10/03/25 (Stablecoin Wars, SEC no...

On The Brink with Castle Island ·

2025/10/03

Matt and Nic are back for another week of news and deals. In this episode: AI bailed out the mining companies AI people deal with the same energy use claims We reflect on the life of Jane Goodall DoubleZero gets a no-action letter from the SEC Will Tether and Circle lose market share? Who could challenge the Big Two stablecoins? Do optimists always win? Some DATs are troubled Is Kalshi starting to take over? Stripe announces Open Issuance The US Government is shut down Content mentioned: Nic on

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31:42

Ben Ward & Steven Pack (RockSolid) on DeFi Vaults...

On The Brink with Castle Island ·

2025/10/01

Wyatt sits down with Ben Ward and Steven Pack of RockSolid. In this episode: What are DeFi vaults? What is RockSolid? Lido vs Rocket Pool Creating effective unified efforts in decentralized communities A look at the wider landscape of DeFi yield How do you measure protocol success? Strengthening the broader Ethereum ecosystem

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29:48

Mark Coe (Intrinsic Edge) on The View From The Public...

On The Brink with Castle Island ·

2025/09/29

Mark Coe, the Founder and CIO of Intrinsic Edge Capital Management joins the show. In this episode we discuss: Mark’s background and path that led him to founding Intrinsic Edge Capital Management. The Intrinsic Edge Digital Infrastructure Fund, a fund that was launched four years ago to focus on companies in the digital asset ecosystem. Perspectives on the mining industry and the impact of AI/LLMs on this sector of the industry. Views on the types of businesses that will enter the public markets

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33:30

Weekly Roundup 09/26/25 (Tether worth $500b?,...

On The Brink with Castle Island ·

2025/09/26

Matt and Nic are back for another week of news and deals. In this episode: We review the Coin Center dinner Tether is going out to raise at $500b Cloudflare wants to launch a stablecoin for agentic payments and launches the 402 protocol Circle is thinking about reversible transactions BitGo files for an S1 Strive acquires Semler Scientific The SEC is looking into 200 DATs for insider trading 9 major European banks are looking to launch a MiCA stablecoin The Bank Policy Institute thinks stablecoins

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51:27

Felipe Montealegre and Noah Goldberg (Theia Capital)...

On The Brink with Castle Island ·

2025/09/22

Wyatt sits down with Felipe Montealegre and Noah Goldberg of Theia Capital, a fund investing actively in liquid crypto tokens with strong fundamentals. In this episode: What drives crypto market valuations? Fundamentals or supply of capital? The imbalance between venture vs hedge fund activity in crypto markets Navigating a market where assets become liquid early in their lifecycle Talent in the crypto industry What makes exceptional founders and team members? Using LLMs in investing and general

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34:40

Weekly Roundup 09/19/25 (SEC listing standards, BoE...

On The Brink with Castle Island ·

2025/09/19

Matt and Nic are back for another week of news and deals. In this episode: The SEC approves generic listing standards for cryptoassets Gensler loses a year’s worth of text messages BoE wants to limit stablecoin exposure to £20k Tether launches USAT Coinbase is exploring a Base token Binance nears the end of DoJ compliance monitoring Galaxy is launching a tokenized money market fund PayPal launches PayPal links

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26:48

Walt Smith (Standard Crypto) on VC Investing in...

On The Brink with Castle Island ·

2025/09/16

Walt joins the podcast to discuss the current state of Bitcoin and what is investable in and around the Bitcoin ecosystem. In this episode: Austrian economics and Bitcoin Bitcoin's strengths and limitations when it comes to innovation and durability The modern role of decentralization and trust Whether nation-states will fully adopt BTC The role of Bitcoin in network states Owning BTC and other cryptoassets directly vs in equity wrappers Assessing the monetary value of cryptoassets BTC for

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32:26

Weekly Roundup 09/12/25 (Hyperliquid stablecoin, CBOE...

On The Brink with Castle Island ·

2025/09/12

Matt and Nic are back for another week of news and deals. In this episode: We reminisce about the fork wars Figure goes public Gemini is slated to list The Winklevoss Quintenz drama rumbles on DAT updates CLARITY updates The fight over stablecoins paying interest continues Prediction markets and sports betting SwissBorg is hacked The CBOE is launching BTC and ETH “continuous futures” Harberger taxes

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47:48

Austin Federa (DoubleZero) on Building a Better...

On The Brink with Castle Island ·

2025/09/08

Wyatt sits down with Austin Federa, the founder of DoubleZero to discuss the hardware systems that underlie blockchains and the internet. In this episode: Building a newer, better fiber network How and why much of internet hardware infrastructure is antiquated Why software innovation has taken precedent over hardware innovation Vertical integration and who has access to the best hardware systems Why hardware innovation requires startups and new entrants Why blockchains demand faster, reliable

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34:07

Weekly Roundup 09/05/25 (Stripe’s Tempo, NASDAQ...

On The Brink with Castle Island ·

2025/09/05

Matt and Nic are back for another week of news and deals. In this episode: We review the US Open The Clippers scandal Fantasy football and the efficient market hypothesis Tax treatment of sports betting on Poly versus sports betting apps Are prediction markets more efficient than bookies? Galaxy launches a tokenized version of their stock NASDAQ is adding supervision rules for DATs Is it over for the DATs? World Liberty Fi launches and gets into a fight with Justin Sun Gemini files to go public

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