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On The Brink with Castle Island

On The Brink with Castle Island

754 episodes — Page 1 of 16

Weekly Roundup 10/23/26 (Gold alchemy, rogue financial AI agents, GENIUS implements stablecoin yield) (EP.746)

Oct 23, 202632 min

Weekly Roundup 10/16/26 (OCC debanking report, Google's quantum advance, Ledger spy chips, Richard Heart apprehended) (EP.745)

Oct 16, 202639 min

Weekly Roundup 10/09/26 (Going Bunker Mode, classical ECC breaks, AI's math discoveries) (EP.744)

Oct 9, 202637 min

Esther Wong (Cashi) on Making Stablecoins Spendable (EP.743)

Oct 5, 202629 min

Weekly Roundup 10/02/26 (Fat Model Hypothesis, Agentic bank runs, Hester Peirce retires from the SEC, ETH 2030) (EP.742)

Oct 2, 202633 min

Weekly Roundup 09/25/26 (Post Clarity rulemaking, Sherrod Brown is back, RIP BitMEX, Coldcard white hats, is EA a cult?) (EP.741)

Sep 25, 202633 min

Weekly Roundup 09/18/26 (Clarity fails to advance, Caroline Ellison's new job, AI leaking MNPI, Poland's oil snafu) (EP.740)

Sep 18, 202638 min

Weekly Roundup 09/11/26 (Liquid hack, AI x-risk, Silvergate revisited, can AI leak MNPI?) (EP.739)

Sep 11, 202647 min

Weekly Roundup 09/04/26 (HuggingFace hack breaks containment, Hyperliquid onshoring, RSA260 factored, is the stablecoin sandwich cheaper?) (EP.738)

Sep 4, 202633 min

Guy Young (Ethena) on Digital Financial Markets (EP.737)

Sep 2, 202633 min

Weekly Roundup 08/28/26 (BankChain alliance, Goat grazing hedges, SHRINCS, is maximalism over?) (EP.736)

Aug 28, 202635 min

Weekly Roundup 08/21/26 (SALT Wyoming, SEC's Reg Crypto, Tether's big 4 audit, Crypto Privateers) (EP.735)

Aug 21, 202633 min

Weekly Roundup 08/14/26 (Anti-Datacenter sentiment, dinosaur fossil investing, SEC is DIYing Clarity) (EP.734)

Aug 14, 202637 min

Weekly Roundup 08/07/26 (Coldcard hack continues, Ethereum mulls an issuance tweak, ai16z winds down, Clarity deadline looms) (EP.733)

Aug 7, 202638 min

Weekly Roundup 07/31/26 (Situational Awareness collapse, Coldcard exploit, latest on CLARITY, Visions of Bitcoin 8 years on) (EP.732)

Jul 31, 202638 min

Weekly Roundup 07/24/26 (BTC Security Consortium, Genesis' Terra trade, DAT departures, Farewell to BitMEX, Network State drama) (EP.731)

Jul 24, 202633 min

Weekly Roundup 07/17/26 (Teleprompter insider trading, the AI DeFi apocalypse fizzles, NY's datacenter ban) (EP.730)

Jul 17, 202639 min

Weekly Roundup 07/09/26 (BonkDAO exploit, Choke Point 2.0 extended to audit firms, Kraken v Mazars) (EP.729)

Jul 10, 202629 min

Weekly Roundup 07/03/26 (OpenUSD announced, Binance leaves the EU, Strategy's new framework) (EP.728)

Jul 3, 202630 min

Weekly Roundup 06/26/26 (Quantum EOs, STRC's selloff, more MSTR) (EP.727)

Jun 26, 202640 min

Weekly Roundup 06/19/26 (STRC under pressure, Illinois' crypto tax, Open weight AI vs the AI boom) (EP.726)

Jun 19, 202638 min

Weekly Roundup 06/12/26 (Strategy survives, Zcash Orchard bug, the thin model hypothesis) (EP.725)

Jun 12, 202638 min

Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724)

Jun 9, 20261h 3m

Weekly Roundup 06/05/26 (MSTR wobbles, Polymarket's MSTR market, Andrew Left convicted) (EP.723)

Jun 5, 202632 min

Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland) (EP.722)

May 29, 202643 min

Weekly Roundup 05/22/26 (AI and power bills, SpaceX IPO, Prime Trust clawbacks, USG invests in quantum) (EP.721)

May 22, 202635 min

Weekly Roundup feat. Gus Coldebella 05/15/26 (Clarity advances, Circle's Arc token) (EP.720)

May 15, 202624 min

Weekly Roundup 05/08/26 (Consensus Miami, AI layoffs strike Coinbase, Clarity compromise, AI energy and water use) (EP.719)

May 8, 202643 min

Weekly Roundup 05/30/26 (DeFi's worst ever month, PTJ on Bitcoin, quantum canaries) (EP.718)

May 1, 202629 min

Pluto (Harbor) on the fate of DeFi after KelpDAO (EP.717)

Apr 27, 202635 min

Weekly Roundup 04/24/26 (Finding Satoshi, KelpDAO retrospective, Insider weather betting, Coinbase's Quantum report) (EP.716)

Apr 24, 202636 min

Brandon Arvanaghi (Meow) on Banking AI Agents (EP.715)

Apr 22, 202618 min

Weekly Roundup 04/17/26 (BIP361 proposal, SEC's DeFi frontend policy, CSW's Bitcoin movie) (EP.714)

Apr 17, 202634 min

Weekly Roundup 04/10/26 (New Satoshi candidates, Mythos' 0-days, CZ's memoir) (EP.713)

Apr 10, 202635 min

Connor Dougherty (Valinor) on the Evolution of Private Credit (EP.712)

Apr 9, 202617 min

Ep 711Weekly Roundup 04/03/26 (Two big quantum papers, Drift protocol hack, Maritime Salvage law) (EP.711)

Matt and Nic are back for another week of news and deals. In this episode: The significance of the new Google and Oratomic papers on quantum computing and ECC256 Why short range attacks are now part of the threat model Is Nic conflicted out from discussing quantum? What will be the fate of the Satoshi coins? What maritime law and shipwreck recovery tells us about the fate of Satoshi's coins Drift protocol is hacked Gary Gensler does not like prediction markets DATs are selling BTC Content mentioned in this episode: Cain et al, Shor's algorithm is possible with as few as 10,000 reconfigurable atomic qubits Babbush et al, Securing Elliptic Curve Cryptocurrencies against Quantum Vulnerabilities: Resource Estimates and Mitigations

Apr 3, 202635 min

Ep 710Weekly Roundup 03/27/26 (Google's Quantum Deadline, Circle's selloff, DATs are selling) (EP.710)

Matt and Nic are back for another week of news and deals. In this episode: Circle stock sells off big on a CLARITY yield update compromise Tether is doing their first big 4 financial audit Who is the CLARITY Act Yield "compromise" good for? Why Circle might benefit from closing the yield loophole Is no bill better than a bad bill? Should Coinbase back the bill? Fannie Mae will accept crypto-backed mortgages Ethereum Foundation launches their post-quantum roadmap Google has revised their quantum transition deadline up to 2029 Why we will not have a lot of warning regarding quantum risk Where is Bitcoin on quantum preparedness? Why it's not all doom and gloom on quantum MARA sells $1b worth of BTC

Mar 27, 202635 min

Ep 709Weekly Roundup 03/20/26 (Vanity Fair fiasco, SEC token taxonomy, tokenized deposits) (EP.709)

Matt and Nic are back for another week of news and deals. In this episode: What happened with the disastrous Vanity Fair photoshoot Kraken postpones their IPO The SEC releases long-awaited guidance distinguishing securities from commodities A compromise may be developing over stablecoin yield The SEC drops their case against Nader Al-Naji Phantom gets a no-action letter from the CFTC Tempo mainnet launches Some regional banks are tokenizing deposits Will agentic payments be a thing Q-day is creeping closer Content mentioned: Galaxy Research, Bitcoin Is Rising to the Challenge of Quantum Readiness Global Risk Institute, Quantum Threat Timeline Report 2025

Mar 20, 202633 min

Ep 708Weekly Roundup 03/13/26 (SEC vs CFTC detente, prediction market surveillance, equitizing tokens) (EP.708)

Matt and Nic are back for another week of news and deals. In this episode: Are we in an oil crisis and energy shock Binance is suing the WSJ for defamation NASDAQ and Kraken partner to bring stocks on chain The SEC and CFTC issue an MOU Prediction markets need surveillance Across is considering converting their token into equity The White House's cyber strategy The banks are still fighting about stablecoin yield What risks do stablecoins actually pose to banks?

Mar 13, 202632 min

Ep 707Weekly Roundup 03/26/26 (Trump supports stablecoin yield, Kraken's master account, death prediction markets) (EP.707)

Matt and Nic are back for another week of news and deals. In this episode: What Dario Amodei and SBF have in common Trump wades in to the market structure debate and asks the banks to come to the table Why stablecoins are not like banks Kraken Financial gets a skinny Fed master account Visa and Bridge are rolling out stablecoin-linked cards The FBI arrests a suspect accused of stealing $46m in BTC from the US marshalls Morgan Stanley is coming out with their own Bitcoin ETF The Aave token governance controversy rumbles on Kalshi's traders are upset about their "death market" policy Content mentioned in this episode: The CIV Youtube Channel Alpen Labs, Size Matters: Architecting BTC Credit Markets

Mar 6, 202631 min

Ep 706Alex Wilson (Cyclops) on Crypto and Stablecoin Payment Solutions (EP.706)

Alex Wilson, Co-Founder and CEO of Cyclops, joins the show. In this episode: Alex's background running The Giving Block and the company's acquisition by Shift4 Difficulty in enabling stablecoin solutions when utilizing existing providers while inside of Shift4 Backgrounds of the founding team at Cyclops Regulatory strategy for Cyclops Products: Pay with Crypto (POS, E-Com), Stablecoin Settlement (for Merchants vs. Wire or ACH), Stablecoin Payouts (Payroll, Contractor Payments, Remittance) Key features for building specifically for payments companies See more at cyclops.io

Mar 4, 202615 min

Ep 705Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius (EP.705)

Dana Syracuse and Josh Boehm of Paul Hastings join the show. In this episode we discuss: The OCC Charter process how digital asset companies are pursuing the federal path The aftermath of the Genius Act passage and the rulemaking process for this law Considerations for Federal vs. State charter pathways The market structure bill Learn more about Paul Hastings

Mar 3, 202631 min

Ep 704Weekly Roundup 02/27/26 (Insider Predicting, OCC implements GENIUS, ZachXTB fingers Axiom, Jane St vs Terra) (EP.704)

Matt and Nic are back with another week of news and deals. In this episode: Kalshi has detected and banned two accounts for insider trading Is Polymarket going to have to add KYC? Is there a tradeoff between informational efficiency and market fairness The OCC de facto bans stablecoin yield in its rulemaking around GENIUS Meta is considering partnering with a stablecoin issuer Stripe is bullish in their annual report ZachXBT determines that Axiom employees have been abusing the platform Terraform labs accuses Jane Street of insider trading WSJ reports that Binance overlooked Iranian sanctions violations Justin Drake unveils a post-quantum roadmap for Ethereum Matt Corallo says Nic is wrong about Bitcoin and quantum Content mentioned: Larry Cermak: How Crypto Actually Works: The Missing Manual

Feb 27, 202634 min

Ep 703Weekly Roundup 02/20/26 (CFTC claims Prediction Markets, rogue AI agents, ETH's existential crisis) (EP.703)

Matt and Nic are back with another week of news and deals. In this episode: Crypto VC funds have some dry powder CFTC chair Mike Selig asserts jurisdiction over prediction markets relative to the States Is Kalshi more reliable than interest rate futures? The CLARITY Act inches closer to passing Shake up at Gemini OpenClaw agents are going to start phishing crypto users Bitwise aims to launch prediction market ETFs Bridge gets their OCC charter Hyperliquid launches a lobbying arm DAT hangover continues Blockfills reveals a $75m hole Ethereum is having an identity crisis Base is moving away from Optimism Neel Kashkari's bad faith stablecoin criticism

Feb 20, 202631 min

Ep 702Raj Parekh (Monad Foundation) on Stablecoins and The Next Era of Fintech (EP.702)

Wyatt sits down with Raj Parekh, Head of Stablecoins and Payments at Monad. In this episode: Will enterprises build out their own stablecoin solutions? Will card payments continue to grow, or be challenged by other forms of payments? What is the role of governments in driving whether stablecoin adoption will continue, accelerate, or decelerate? How does Monad work with leading financial organizations? Where do you see opportunity for novel tech solutions around stablecoins? Will there be many stablecoins or a smaller number of stablecoins at scale? Will companies run their own corporate chains? How should companies look at embedding stablecoins in their workflows from scratch?

Feb 18, 202638 min

Ep 701Weekly Roundup 02/13/26 (SBF wants a retrial, taking stock of Web3, Clarity deadlocked) (EP.701)

Matt and Nic are back with another week of news and deals. In this episode: Matt reflects on the Patriots season We review the Superbowl Ads Looking forward to the OpenAI wearable Is "something big happening" in AI? Does crypto accelerate the rise of malicious AI? Are all communications networks going to break down in 90 days? SBF wants a new trial Blackrock adds BUIDL to Uniswap Blockfills suspends withdrawals Robinhood is internalizing their prediction market product The stablecoin yield issue in Clarity is still a problem Fairshake is getting active in the midterms Is Chris Dixon right about Web3? We review winter olympic sports Content mentioned: Chris Dixon, The long game for crypto

Feb 13, 202642 min

Ep 700Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700)

Wyatt sits down with Bhavin, co-founder of Birch Hill to chat about the tokenized asset and DeFi market broadly. In this episode: Who is assessing whether cryptoassets are safe in DeFi today? Who is assessing risk and ensuring assets are solvent and not fraudulent? How have these standards been set and how are they evolving? What is a risk curator, how do risk curators make money, and what is their role? Is it the responsibility of protocols, curators, wallets, or someone else to protect users from buying bad assets? How do you expect non-DeFi-native market participants will start to enter this market? Will users eventually buy, hold, and sell assets on protocol interfaces, brokerages / exchanges, or risk curator interfaces? Does the Fat Protocol Thesis hold true? Where does value accrue today?

Feb 11, 202636 min

Ep 699Weekly Roundup 02/06/26 (Bitcoin bloodbath, Digesting Epstein's Emails, Ethereum rethinks L2s) (EP.699)

Matt and Nic are back with another week of news and deals. In this episode: Bitcoin grapples with the fallout of the Epstein Emails Did Jeffrey Epstein influence Bitcoin development? Is Bhutan selling their Bitcoin? Do Bitcoin devs care about quantum? Is Bitcoin Core under the influence with sophons Kyle Samani steps back from Multicoin What Samani's departure means for crypto Is web3 dead forever? Vitalik starts second-guessing the L2-centric roadmap Tether is trading at a slight discount Content mentioned in this episode: Nic on Substack, Bitcoin developers are mostly not concerned about quantum risk

Feb 6, 202641 min

Ep 698Weekly Roundup 01/30/26 (Fidelity's FIDD, Gold rally, Worldcoin and AI bots, digital alibis) (EP. 698)

Matt and Nic are back with another week of news and deals. In this episode: Matt is heated about the Belichick HoF vote Fidelity launches a stablecoin FIDD on Ethereum Market structure passes Senate Ag Cmte The White House crypto council is being revived to find a compromise on stablecoin yield Fairshake has another war chest for the midterms Do stablecoins cause bank deposit contraction? Tether has 140 tons of gold now Why is Bitcoin not participating in the "debasement" trade? Is gold at risk from alchemy? People are still worried about quantum Will Worldcoin save us from AI bots? What's the solution to the AI slop apocalypse? Digital alibis with blockchains Content mentioned in this episode: Niall Ferguson and Manny Rincon-Cruz, Stablecoins Are the Future but Banks will Survive McKinsey and Artemis, Stablecoins in payments: What the raw transaction numbers miss

Jan 30, 202638 min

Ep 697Weekly Roundup 01/23/26 (CLARITY stalls, Iran's USDT reserves, Is Web3 Social over?) (EP.697)

Nic and Matt are back for another week of news and deals. In this episode: There's a big storm coming Matt's playoff picks Farcaster sells to Neynar Is this the nail in the coffin for Web3Social? Where Farcaster went wrong BitGo goes public NYSE is building a tokenized security trading platform Are we looping back around to enterprise blockchains? A MA judge has issued an injunction against Kalshi Jeffries drops Bitcoin from its model portfolio over quantum risk Coinbase launches an advisory board on quantum Trump sues JPM for debanking him Does the Central Bank of Iran really control $500m worth of USDT? What's next for Caroline Ellison?

Jan 23, 202636 min