On The Brink with Castle Island

Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland) (EP.722) 29.05.2026 43p

Matt and Nic are back with another week of news and deals. In this episode: The CEO of Lead bank says debanking was made up Which aspects of debanking were real? The SEC scraps its 50-year-old gag rule The WSJ gets free banking history wrong in their attack on stablecoins What does history tell us about decentralized monetary issuance Why stablecoins aren't vulnerable to the same issues as free banks SoFi launches SoFiUSD and mixes a stablecoin with a tokenized deposit Sentiment is bottoming in Ethereum David Hoffman sells his ETH Are stablecoins parasitic to L1s Can L1s accrue value sustainably? The DATs are troubled Is AGI here already? AI cost discipline Content mentioned in this episode: Nic on Substack, Stablecoins are private money. There's nothing wrong with that

Weekly Roundup 05/22/26 (AI and power bills, SpaceX IPO, Prime Trust clawbacks, USG invests in quantum) (EP.721) 22.05.2026 35p

Matt and Nic are back with another week of news and deals. In this episode: Are AI datacenters better or worse for the environment than Bitcoin miners? AI is not responsible for your power bills Why AI could actually drive down residential power prices Is AI less popular than crypto ever was? The negative societal effects of tech companies staying private for longer We analyze the SpaceX S1 OpenAI solved one of the Erdos problems The US government is taking equity stakes in quantum computers Jane Street is still dealing with the Terra fallout Prime Trust is trying to claw back assets from Swan The SEC has questions about tokenized equities Content mentioned in this episode: Nic on Substack, AI is not hiking your electricity bill - yet

Weekly Roundup feat. Gus Coldebella 05/15/26 (Clarity advances, Circle's Arc token) (EP.720) 15.05.2026 24p

Matt and Nic are aback with another week of news and deals, today joined by Gus Coldebella to cover the CLARITY Act. In this episode: The Clarity Act advances resoundingly from committee Sen. Warren doesn't like the Clarity Act Will there be an ethics provision inserted into Clarity? The next fight in DC What's up with Nantucket real estate? Nantucket's ponzinomics Nantucket is the birthplace of venture capital Circle is issuing a token Cprkrn recovers 5 BTC with the help of Claude

Weekly Roundup 05/08/26 (Consensus Miami, AI layoffs strike Coinbase, Clarity compromise, AI energy and water use) (EP.719) 08.05.2026 43p

Matt and Nic are back for another week of news and deals. In this episode: Will Hantavirus become another global pandemic? Kraken buys Reap for $600m Bullish buys Equiniti for $4.2b Reflections on 10 years of attending Consensus Is it acceptable to wear a backpack with a suit a16z crypto announces a $2.2b fundraise Coinbase is laying off 14% of the firm Will AI lead to massive job losses? Is VC immune from AI job displacement I bipartisan compromise is finally reached on Clarity How the AI water use debate is just like Bitcoin The AI lobby is learning from Fairshake The SEC delays prediction market ETFs

Weekly Roundup 05/30/26 (DeFi's worst ever month, PTJ on Bitcoin, quantum canaries) (EP.718) 01.05.2026 29p

Matt and Nic are back for another week of news and deals. In this episode: DeFi had its worth month of hacks ever How are people falling for the fake Zoom link hack The KelpDAO Aave bailout is happening Is Bitcoin's security degrading because miners are pivoting to AI? Litecoin suffers a 51% attack Is Bitcoin PoW at risk? Computershare partners with Securitize Meta will offer creator payouts in stablecoins via Stripe Q-day prize controversy Why quantum canaries might not provide much of a warning Paul Tudor Jones is spooked by quantum Some evidence for insider information in political prediction markets

Pluto (Harbor) on the fate of DeFi after KelpDAO (EP.717) 27.04.2026 35p

Pluto is a veteran of DeFi and cross chain systems, with prior stints at Thorchain and Airswap, now building Harbor, a native asset DEX. In this episode, we talk about the KelpDAO exploit and how DeFi can regain people's trust. Nic sits down with him to discuss: What exactly happened with the KelpDAO/ Aave hack? Will new AI models make hackers more proficient? Is advanced AI a defensive or offensive technology for smart contracts? Why protocol exposures are often not on chain Why DeFi might want to segregate execution from settlement Is it possible to have instant settlement and proactive monitoring Do we have anything to learn from DeFi What could Aave have done different? Where did LayerZero go wrong? Can DeFi work if there are occasional freezes and seizures? Pluto's reflections on Thorchain What Thorchain did right Arbitrum's questionable precedent What Pluto is building with Harbor Where does DeFi go from here? Learn more about Harbor and follow Pluto on X

Weekly Roundup 04/24/26 (Finding Satoshi, KelpDAO retrospective, Insider weather betting, Coinbase's Quantum report) (EP.716) 24.04.2026 36p

Matt and Nic are back for another week of news and deals: The Finding Satoshi documentary has a new guess Was it Hal or Len? Could Satoshi have been a team? Why Stylometry might not reveal Satoshi Why the cypherpunks were interested in resurrection What happened with KelpDAO? Is DeFi cooked? Is Arbitrum decentralized? The Paris temperature market was manipulated Coinbase releases their highly-anticipated quantum risk report Performance tradeoffs for post-quantum signature schemes SBF was a good investor The Justin Sun WLFI saga continues Did an Indian tanker fall victim to a crypto scam in the Strait of Hormuz? Content mentioned in this episode: Finding Satoshi Documentary Fidelity Digital Assets, Getting Off Zero: Evaluating Bitcoin in 2026 Coinbase, Quantum report

Brandon Arvanaghi (Meow) on Banking AI Agents (EP.715) 22.04.2026 18p

Brandon Arvanaghi, the co-founder and CEO of Meow, joins the show. In this episode we discuss: The rise of agentic payments and the convergence of LLMs and financial services. Meow's approach to banking the agentic economy. How financial services firms and banks will need to evolve in order to service AI agents. Meow's product roadmap. Meow recently made history as the first fintech to enable AI agents to open business bank accounts and virtual cards. Meow has been building the banking and treasury infrastructure for crypto-native and VC-backed companies for several years now. This includes USDC/USDT rails, stablecoin card programs, treasury management, and FX. To learn more about Meow visit meow.com

Weekly Roundup 04/17/26 (BIP361 proposal, SEC's DeFi frontend policy, CSW's Bitcoin movie) (EP.714) 17.04.2026 34p

Matt and Nic are back for more news and deals: Jameson Lopp's BIP361 gets an official BIP number What about an official salvage process for the quantum-vulnerable Satoshi coins What about recycling Satoshi's bitcoins into long-term tail emissions Why the Satoshi freeze war will be unlike the Blocksize war Kraken confidential files for an IPO The SEC says defi frontends might not be broker dealers even if they list tokenized securities Goldman files for a Bitcoin ETF WLFi is having a feud with Justin Sun Ether Machine, an Ethereum DAT winds down There is a new Satoshi documentary coming out There is an A-list Hollywood movie coming out about Craig Wright Leo Aschenbrenner's secret Tether invests into Drift Protocol post-hack Why is USDC refusing to freeze funds after hacks? Do we need an "on-chain" Chancery Court for blockchains Content mentioned on this episode: Nic on X, How to resolve the matter of the Satoshi coins without a freeze

Weekly Roundup 04/10/26 (New Satoshi candidates, Mythos' 0-days, CZ's memoir) (EP.713) 10.04.2026 35p

Matt and Nic are back with another week of news and deals. In this episode: The New York Times thinks Adam Back is Satoshi The problems with the NYT's analysis The case for Len Sassaman The case for Satoshi not being alive Could Satoshi be a group? Why Satoshi might be discovered this year Morgan Stanley launches their Bitcoin ETF Scott Bessent asks for Congress to pass Clarity The White House finds that stablecoin yield would not harm the banking system Kalshi secures a key win in a NJ appeals court Anthropic's Mythos model is exposing vulnerabilities CZ is publishing a memoir Will Hormuz tolls be payable in Bitcoin?

Connor Dougherty (Valinor) on the Evolution of Private Credit (EP.712) 09.04.2026 17p

Connor Dougherty, Co-Founder and CEO of Valinor Digital, joins the show. In this episode: Connor's background working at a large private credit shop Pioneering a new category of Open Credit and how it expands the TAM for private credit Explosion of stablecoin demand enabling new borrowing types Structuring deals to align with traditional private capital and onchain lending Building a modern credit institution by utilizing technology See more at valinordigital.com

Weekly Roundup 04/03/26 (Two big quantum papers, Drift protocol hack, Maritime Salvage law) (EP.711) 03.04.2026 35p

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

Weekly Roundup 03/27/26 (Google's Quantum Deadline, Circle's selloff, DATs are selling) (EP.710) 27.03.2026 35p

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

Weekly Roundup 03/20/26 (Vanity Fair fiasco, SEC token taxonomy, tokenized deposits) (EP.709) 20.03.2026 33p

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

Weekly Roundup 03/13/26 (SEC vs CFTC detente, prediction market surveillance, equitizing tokens) (EP.708) 13.03.2026 32p

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?

Weekly Roundup 03/26/26 (Trump supports stablecoin yield, Kraken's master account, death prediction markets) (EP.707) 06.03.2026 31p

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

Alex Wilson (Cyclops) on Crypto and Stablecoin Payment Solutions (EP.706) 04.03.2026 15p

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

Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius (EP.705) 03.03.2026 31p

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

Weekly Roundup 02/27/26 (Insider Predicting, OCC implements GENIUS, ZachXTB fingers Axiom, Jane St vs Terra) (EP.704) 27.02.2026 34p

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

Weekly Roundup 02/20/26 (CFTC claims Prediction Markets, rogue AI agents, ETH's existential crisis) (EP.703) 20.02.2026 31p

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