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On The Brink with Castle Island — Business
On The Brink with Castle Island

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

Latest Episodes:

Weekly Roundup 08/01/25 (SEC's Project Crypto, In-kind ETFs, White House report) (EP.651) Aug 01, 2025

Show notes

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 Dashboard
Omid Malekan and Zach Pandl, Stablecoins and the Singleness of Money
White House, Strengthening American Leadership in Digital Financial Technology
Paul Atkins, American Leadership in the Digital Finance Revolution
Nic Carter, The Last Word on Stablecoins and Free Banking

Michael Bentley (Euler) on Euler's Comeback (EP.650) Jul 28, 2025

Show notes

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

Weekly Roundup 07/25/25 (Tether's GENIUS options, Defending Free Banks, Saylor's Stretch) (EP.649) Jul 25, 2025

Show notes

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 new stablecoin issuance platform. The first stablecoin product will be USDtb in partnership with Ethena Labs
The Senate Banking Committee released their discussion draft for crypto market structure legislation this week, designed to build off the House's passage of the CLARITY Act last week
Citadel Securities has expressed concern around the rise of tokenized securities
Bhutan's Bitcoin trade
BitGo, a crypto custody provider, and Bullish, a crypto exchange, both announced that they had confidentially filed an S-1

Further reading:

Wired, The Great Crypto Re-Banking Has Begun
Galaxy Digital, Crypto Policy Under Trump: H1 2025 Report

Cyrus Shirazi (Haven) on Better Bookkeeping for Crypto Startups & Beyond (EP.648) Jul 21, 2025

Show notes

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

Weekly Roundup 07/18/25 (GENIUS is Law, Clarity passes, narrow banking and GENIUS) (EP.647) Jul 18, 2025

Show notes

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 stablecoins and banks

Nikhil Raghuveera (Predicate) on Policy Engines for Blockchains (EP.646) Jul 14, 2025

Show notes

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

Weekly Roundup 07/11/25 (New BTC ATH, Crypto Week, Zelensky suit scandal) (EP.645) Jul 11, 2025

Show notes

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 Currency
There are new public access vehicles
Andreessen wants you to leave Delaware
A fundamental valuation model for L1s?
GMX is hacked for $42m
Tim Massad's exchange with Bernie Moreno

Content mentioned in this episode:

Hester Peirce, Enchanting, but Not Magical: A Statement on the Tokenization of Securities
Fidelity, Blockchains as emerging economies
Bridge, How Meow and Bridge Make USDC Payments as Seamless as Cash

Zac Townsend (Meanwhile) on Bitcoin Life Insurance (EP.644) Jul 10, 2025

Show notes

Zac Townsend, the founder and CEO of Meanwhile, joins the show. In this episode we discuss:

Zac's background and the path that led him to start Meanwhile.
The mechanics of Bitcoin denominated life insurance.
How Meanwhile generates Bitcoin yield.
Zac's views on the evolution of Bitcoin treasury companies.

To learn more about Meanwhile visit meanwhile.bm

Charles Hamel (Opera MiniPay) on Globalizing Dollar Access (EP.643) Jul 09, 2025

Show notes

Charles Hamel, Product Director at Opera's MiniPay, joins the show. In this episode:

Stablecoin habits in emerging markets
Prospects for local stablecoins
What's next on the stablecoin horizon

Weekly Roundup 07/04/25 (Tokenized stocks, Crypto Week, BBB passes) (EP.642) Jul 04, 2025

Show notes

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

EthCC troubles
Robinhood has been shipping
Figma owns BTC
The House GOP has declared "crypto week" in July
Circle and Ripple are applying for bank charters
AI companies are buying Bitcoin miners
Sharia finance
The BBB passes
America teeters towards default
The Sohan Parekh fiasco
How do tokenized stocks work?
Another architect of OCP2.0 bites the dust
Is AI going to usher in a socialist revolution?
Ric Edelman wants you to buy crypto
Franklin Templeton is worried about bitcoin treasury companies
No crypto language was included in the BBB

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