Weekly Roundup 06/24/22 (FTX steps in, 3AC postmortem, fraying DeFi governance) (EP.328)
On The Brink with Castle Island
Release Date: 06/24/2022
Sandy Kaul (Franklin Templeton) on Onchain Asset Management (EP.670)
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
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Weekly Roundup 08/15/25 (DAT fine print, stablecoin L1s, banks vs stables) (EP.656)
On The Brink with Castle Island
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 buying Bitcoin Is monero being 51% attacked? Content mentioned: BitMEX...
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Huf Haus (Pear Protocol) on Trading Strategies Across Crypto Cycles (EP.655)
On The Brink with Castle Island
We sit down with , founder of . 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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Nathan McCauley on Anchorage Digital Prime and Stablecoin White-Label (EP.654)
On The Brink with Castle Island
, the founder and CEO of 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 visit their . Follow Nathan on . See also:
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Weekly Roundup 08/08/25 (Debanking EO, Storm Verdict, RMB stables) (EP.653)
On The Brink with Castle Island
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 reading: Hester Peirce, Nic on Substack,
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Sid Powell (Maple) on Maple's Comeback & DeFi Credit Markets (EP.652)
On The Brink with Castle Island
CEO and cofounder 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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Weekly Roundup 08/01/25 (SEC’s Project Crypto, In-kind ETFs, White House report) (EP.651)
On The Brink with Castle Island
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’ Omid Malekan and Zach Pandl, White House, Paul Atkins, Nic Carter,
info_outlineMatt and Nic return for a fiery episode of deals and news. In this episode:
- Is miner selling backed up by the on-chain data?
- Is Massachusetts open to pro-crypto legislation?
- FTX provides credit support to embattled crypto lenders
- Why private market transactions do not constitute bailouts in the pejorative sense
- Was 3 Arrows just a case of too much leverage and bad trades, or was it fraud?
- Does the 3AC situation stray into criminal territory?
- There were significant harms stemming from the 3AC scheme
- Kyle's infamous On The Brink appearance and his special request
- Did GBTC bring down 3AC?
- Are we entering the PvP era of crypto twitter?
- The story behind 3AC's yacht
- Solend requisitions user funds
- Wartime versus peacetime governance in DeFi
- South Korea puts a travel ban on Terraform labs employees
- DYDX is leaving Ethereum and moving to their own chain
- The relationship between lender balance sheets and GBTC
- Is there a case to be made for winding down GBTC?
- How to think about the GBTC trade today
- How the 3AC GBTC trade is like LTCM
- How to think about the "macro"
- Is the 'crypto hedge fund that also does VC' obsolete?
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