Weekly Roundup 12/23/22 (Caroline pleads, SBF is extradited, Visa’s autopayments) (EP.383)
On The Brink with Castle Island
Release Date: 12/23/2022
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_outlineMatt and Nic return for another week of news and deals. In this episode:
- Are stablecoins still a priority in DC?
- The rise of the FUDfluencer
- Sam agrees to be extradited
- Did the SDNY wait for Sam to be extradited to release Caroline’s plea deal?
- Alameda was siphoning FTX funds from day 1
- What’s the deal with Modulo Capital?
- Is Gerald Cotten back from the dead?
- Does Flashboys need a new chapter?
- What is going on with IEX?
- How did Michael Lewis not figure out something was up at FTX?
- Sen. Pat Toomey’s stablecoin legislation
- Core Scientific files for bankruptcy
- Why the mining shakeout might lead to consolidation
- The Fed’s stablecoin blog
- Visa’s autopayments for non-custodial wallets
- Stablecoins are having a great year
- Where are the remaining FTX execs?
Content mentioned:
- Coinbase, Regulating Crypto: How we move forward as an industry from here
- Visa, Auto Payments for Self-Custodial Wallets
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