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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

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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33:46

Daniel Lev (Coinflow) on Stablecoin Payments (EP.662)

On The Brink with Castle Island ·

2025/09/02

Wyatt sits down with Daniel Lev, the founder of Coinflow, to discuss the evolution of payments amidst a wave of stablecoin-enabled innovation. In this episode: Lurking legacy issues of payment networks How our current payment networks benefit end users but not merchants Types of merchant profiles and who stands to benefit Creating faster settlement Marketplace models and better rails How blockchain can reduce fraud and help businesses know their customers

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32:40

Weekly Roundup 08/29/25 (Stablecoins in CDMX, DAT...

On The Brink with Castle Island ·

2025/08/29

Nic and Matt return for another week of news and deals. In this episode: Nic reviews the stablecoin conference in Mexico City Will the banks obsolete stablecoins? Some DATs are having trouble The government is putting GDP on the blockchain The CFTC opens the door to US customers trading on non-US exchanges Trump fires Lisa Cook Can the Fed be considered “independent” Google is developing a blockchain A BNB DAT gets delisted Tether is building on Bitcoin via RGB How does insider trading work in

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29:57

Sandy Kaul (Franklin Templeton) on Onchain Asset...

On The Brink with Castle Island ·

2025/08/25

Wyatt sits down with Sandy Kaul, head of digital assets at Franklin Templeton, to cover Sandy's work with the CFTC and DTCC and creating sandboxes for onchain financial markets. In this episode: How wallets stand to become the hub of asset management Lasting policy for crypto Protecting consumers in an open financial system

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39:29

Weekly Roundup 08/22/25 (SALT Jackson Hole, Wyoming...

On The Brink with Castle Island ·

2025/08/22

Matt and Nic are back with another week of news and deals. In this episode: Wyoming releases a stabletoken “FRNT” Matt’s bear encounter Bowman and Waller’s speeches at Jackson Hole Eric Trump’s Bitcoin prediction Is there an example of a DAT that makes sense? Should DATs trade at a persistent premium? Figure is going public Bullish goes public Is Saylor cornered? Quintenz’ nomination The DoJ decriminalizes writing open source code Is Polymarket cooked? Does a trial by a jury of your peers make

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27:05

Cupid & Hercules (Groom Lake) on Preventing and...

On The Brink with Castle Island ·

2025/08/21

Wyatt sits down with the founders of Groom Lake. In this episode: How social engineering attacks are being used to exploit companies in crypto and beyond How companies can better protect themselves and be vigilant of these exploit attempts The future of cybersecurity software for crypto

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29:44

Luke Xie (SatLayer) on The Next Generation of Bitcoin...

On The Brink with Castle Island ·

2025/08/18

Wyatt sits down with Luke Xie, cofounder of SatLayer for a conversation about Bitcoin yield. In this episode: What makes financial markets for BTC unique How BTC DeFi will evolve, in the backdrop of the broader macro environment DeFi vs CeFi financial systems for BTC

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38:45

Weekly Roundup 08/15/25 (DAT fine print, stablecoin...

On The Brink with Castle Island ·

2025/08/15

Matt and Nic return for another week of news and deals. In this episode: We review the DAT fine print Why being in power is sometimes the hardest part Stripe and Circle announce their own L1s We make the case for stablecoin L1s The irony in Stripe's L1 What about a DAT of DATs? Bullish goes public Breakfast cereals Do Kwon pleads guilty BPI sends a letter to Congress complaining about stablecoin interest Can you prohibit stablecoin yield? Bo Hines steps down Bessent says the USG will not be

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32:13

Huf Haus (Pear Protocol) on Trading Strategies Across...

On The Brink with Castle Island ·

2025/08/13

We sit down with Huf Haus, founder of Pear Protocol. In this episode: What pair trading is, the benefits of Pear trading, and different strategies How to approach different market regimes from a trader's perspective Applying trading strategies to other asset classes

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30:19

Nathan McCauley on Anchorage Digital Prime and...

On The Brink with Castle Island ·

2025/08/11

Nathan McCauley, the founder and CEO of Anchorage joins the show. In this episode we discuss: The passage of The Genius Act and the impact it will have on the digital asset industry. The launch of Anchorage’s white label stablecoin issuance platform. Anchorage Digital Prime and how the company is working with its customers on trade execution, lending and custody. The status of the market structure bill. The Roman Storm case. To learn more about Anchorage visit their website. Follow Nathan on X

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39:36

Weekly Roundup 08/08/25 (Debanking EO, Storm Verdict,...

On The Brink with Castle Island ·

2025/08/08

Matt and Nic are back for another week of news and deals. In this episode: What’s wrong with NYC? China bans Bitcoin for the 15th time Is China really lauching an RMB stablecoin? We dissect the Trump debanking EO OpenAI releases GPT5 SEC: Liquid staking tokens are not securities Roman Storm is found guilty on one of three counts Hester Peirce’s speech on financial privacy How should we solve debanking? Will stablecoins replace bank wires? Is AI going to reveal the identity of Satoshi Further

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39:13

Sid Powell (Maple) on Maple's Comeback & DeFi Credit...

On The Brink with Castle Island ·

2025/08/04

Maple Finance CEO and cofounder Sid Powell joins the show to talk about Maple's huge year so far. In this episode: Syrup and Maple's evolution into an on-chain asset manager Traditional credit players servicing on-chain finance DeFi's strengths and weaknesses relative to traditional markets

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31:12

Weekly Roundup 08/01/25 (SEC’s Project Crypto,...

On The Brink with Castle Island ·

2025/08/01

Matt and Nic are back for another week of news and deals. In this episode: The White House publishes their highly awaited crypto report SEC Chair Paul Atkins makes a landmark speech Stablecoin-focused L1s DAT mNAV premia are converging to 1 Figma IPO The SEC embraces tokenized securities, airdrops, token issuance, and DeFi In-kind create and redeem has been authorized for Bitcoin ETFs JPM deepens their partnership with Coinbase Roman Storm verdict is imminent Further reading: Blockworks’ DAT

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46:28

Michael Bentley (Euler) on Euler's Comeback (EP.650)

On The Brink with Castle Island ·

2025/07/28

Wyatt sits down with Michael Bentley, the founder of Euler. In this episode: Euler's founding story, infamous security incident, and comeback story How the team and protocol stayed together in the face of immense challenges The value of personal relationships in crypto despite a pseudonymous culture

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37:06

Weekly Roundup 07/25/25 (Tether’s GENIUS options,...

On The Brink with Castle Island ·

2025/07/25

Matt and Nic are back with another week of news and deals. In this episode: Defending “Free Banking” from the critics – and why stablecoins are unlike free banks The American Bankers Association doesn’t like new crypto charters Tether CEO Paolo Ardoino announces the company’s plan to launch a new US-based stablecoin this year Strategy announced the plans for the fourth preferred stock offering this week, STRC, or "Stretch." Anchorage Digital, which does hold an OCC banking charter, is launching a

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32:18

Cyrus Shirazi (Haven) on Better Bookkeeping for...

On The Brink with Castle Island ·

2025/07/21

Cyrus Shirazi, CEO of Haven joins the show. In this episode: R&D tax credits and offering an attractive tax product to early stage companies What on-chain finance needs to fulfill becoming a better ledger for accounting What startups should look for in a tax & accounting partner

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36:44

Weekly Roundup 07/18/25 (GENIUS is Law, Clarity...

On The Brink with Castle Island ·

2025/07/18

Matt and Nic are back for another week of news and deals. In this episode: The Coldplay concert incident It’s Crypto Week in Washington Talos acquires Coin Metrics Do you need an MTL to run a fantasy football league? GENIUS Act is law pending Trump’s signature Clarity Act passes the House Pump.fun ICO Fairshake raises $141m Grayscale is preparing for an IPO Adam Back’s Bitcoin access vehicle Polymarket beats the allegations Is GENIUS creating a narrow bank system? Governor Waller's comments on

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34:21

Nikhil Raghuveera (Predicate) on Policy Engines for...

On The Brink with Castle Island ·

2025/07/14

Wyatt sits down with Nikhil Raghuveera of Predicate to talk policy for blockchain applications. In this episode: How Predicate’s “rules for blockchain transactions” are making on-chain finance more scalable and secure Creating more compliant stablecoin transfer systems suitable to mass financial use cases The future of secure money movement How leading software and financial firms can integrate transaction policies in their workflows

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34:45

Weekly Roundup 07/11/25 (New BTC ATH, Crypto Week,...

On The Brink with Castle Island ·

2025/07/11

Matt and Nic are back for another week of news and deals. In this episode: Bitcoin hits a new ATH and no one is talking about it Grok goes haywire The White House posts chudjak Core Weave looks to buy Core Scientific Stablecoins are going to pay yield anyway Did Zelenskyy wear a suit? How should prediction markets be settled? Pump.fun ICO is coming up Hester Peirce issues a warning on tokenized securities Crypto Week in Congress is coming up Jonathan Gould has been confirmed as Comptroller of the

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177 results

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