Iain Murray (Competitive Enterprise Institute) on the history of Operation Choke Point (EP.169)
On The Brink with Castle Island
Release Date: 01/18/2021
Walt Smith (Standard Crypto) on VC Investing in Bitcoin (EP.666)
On The Brink with Castle Island
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 payments?
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Weekly Roundup 09/12/25 (Hyperliquid stablecoin, CBOE continuous futures, stablecoin interest) (EP.665)
On The Brink with Castle Island
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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Austin Federa (DoubleZero) on Building a Better Internet (EP.664)
On The Brink with Castle Island
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 bandwidth Why a token framework offers a better incentive mechanism
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Weekly Roundup 09/05/25 (Stripe’s Tempo, NASDAQ tightens rules on DATs, WLF vs Sun) (EP.663)
On The Brink with Castle Island
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 Stripe releases details around their Tempo L1 Some academics have an explanation for why MSTR...
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Daniel Lev (Coinflow) on Stablecoin Payments (EP.662)
On The Brink with Castle Island
Wyatt sits down with , the founder of , 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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Weekly Roundup 08/29/25 (Stablecoins in CDMX, DAT issues, GDP on the blockchain) (EP.661)
On The Brink with Castle Island
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 prediction markets?
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Sandy Kaul (Franklin Templeton) on Onchain Asset Management (EP.660)
On The Brink with Castle Island
Wyatt sits down with , 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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Weekly Roundup 08/22/25 (SALT Jackson Hole, Wyoming Stable Token, Fed drama) (EP.659)
On The Brink with Castle Island
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 sense? Content mentioned: Reducible Errors,
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Cupid & Hercules (Groom Lake) on Preventing and Responding to Cybercrime (EP.658)
On The Brink with Castle Island
Wyatt sits down with the founders of 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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Luke Xie (SatLayer) on The Next Generation of Bitcoin Yield (EP.657)
On The Brink with Castle Island
Wyatt sits down with , cofounder of 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
info_outlineIain Murray, VP of Strategy at the Competitive Enterprise Institute, joins the show to discuss the history of Operation Choke Point, a 2011-2015 program used to exclude legal businesses from banking led by the DoJ and FDIC. In this episode:
- How Iain Murray came to be one of the main historians of Operation Choke Point
- The roots of Choke Point in the crackdown on poker sites in 2011
- How Choke Point was started on a whim by two midlevel DoJ lawyers in 2011
- How OCP targeted completely legal but politically disfavored industries
- How mechanically the DoJ was able to get banks to comply with their informal guidance
- Why the closed nature of banking means that alternatives financial service providers for these industries couldn't be created
- How bank consolidation meant that OCP was easier to instrumentalize
- How successful was Choke Point in marginalizing targeted industries?
- Did OCP have buy-in from the highest levels of the Obama administration?
- How regulations should have implemented the rules they sought to create with Choke Point – and why they chose not to
- How OCP was an end-around the administrative procedure act, and why it was done covertly
- Was there any accountability for the individuals behind OCP? Was anyone fired?
- Why individuals on any side of the political spectrum should be concerned about OCP
- Did Choke Point ever really end?
- The long term enduring effects of OCP
- How the Wyoming SPDI is a reaction to Choke Point
- Whether Iain agrees with the OCC's 'Fair Access' rule
Content mentioned in this episode:
- Iain Murray at CEI, Operation Choke Point: What it is and why it matters
- OCC, 'Fair Access' rule