On The Brink with Castle Island
Hosts Matt Walsh and Nic Carter of Castle Island Ventures explore news and deals in the public blockchain space and talk to some of the leading experts in the industry. Learn more and stay up to date at CastleIsland.vc and follow on twitter @CastleIslandVC
Weekly Roundup 10/30/26 (Prediction market election hiccups, Hyperliquid onshoring, pubcos push back at tokenization)
Editor's note: this episode was recorded before the Binance hack.
Matt and Nic are back with another week of news. In this episode:
Prediction markets keep screwing up around major elections Quantum firm Alice and Bob devise a new lower estimate for an ECDLP break Google enters institutional crypto custody with Google MPC ICE and Trade.xyz plan to bring Hyperliquid perps to the US, pending CFTC approval DTCC's tokenization service goes live on Canton and its private Besu chain Who is using Instinct? Who's behind the anonymous WSJ ad warning companies against tokenized stocks? Should p...Weekly Roundup 10/23/26 (Gold alchemy, rogue financial AI agents, GENIUS implements stablecoin yield)
Matt and Nic are back with another week of news. In this episode:
Marathon Fusion says it has turned mercury into stable gold
What would commercially viable alchemy mean for Bitcoin's scarcity argument?
AI tools uncover a major vulnerability in PHP
A certificate authority's private keys turn out to be trivially guessable
Railway warns developers to revoke their secrets after a cyberattack
Banks are finding third-party AI agents inside customer accounts
Who's responsible when your AI agent acts without instructions?
The OCC finalizes...
Weekly Roundup 10/16/26 (OCC debanking report, Google's quantum advance, Ledger spy chips, Richard Heart apprehended)
Matt and Nic are back with another week of news and deals. In this episode:
The OCC publishes its debanking findings on America's largest banks
Will the banks' fixes satisfy regulators?
Google makes another advance in quantum error correction
Coinbase lays out its requirements for Bitcoin's post-quantum migration
Can Bitcoin's quantum transition accommodate institutional MPC wallets?
OpenAI is reportedly in talks to buy Trail of Bits
Patrick Witt leaves the White House — where does that leave Clarity?
DWF Labs subsidiaries sue BitGo for $141m...
Weekly Roundup 10/09/26 (Going Bunker Mode, classical ECC breaks, AI's math discoveries)
Matt and Nic are back with more deals and news. In this episode:
Is it appropriate to have AI manage your fantasy league? Quant firms are hiring "quals" Justin Drake scares everyone in crypto Did AI destroy math? Why a classical ECDSA break would be worse than a quantum one Why we lean forward hash-based signatures for post-quantum Why rotating your address doesn't help now Is Bitcoin the "least of our concerns" if ECC breaks? Nic makes a new scientific discovery with Astra The NFL thinks that gambling should be state regulated What's driving interest in Pokemon cards?Esther Wong (Cashi) on Making Stablecoins Spendable
Esther Wong, founder and CEO of Cashi joins the show. Cashi is a stablecoin spending app and cashback card with a global footprint. In this episode we discuss:
Customer personas and use cases for stablecoin payments The future of tokenized equities on chain The landscape of layer one and two blockchains and how these platforms converge with global stablecoin applications Cashi's roadmap and plans for the coming yearTo learn more about Cashi, visit their website and follow Esther Wong on X.
Weekly Roundup 10/02/26 (Fat Model Hypothesis, Agentic bank runs, Hester Peirce retires from the SEC, ETH 2030)
Matt and Nic are back with another week of news and deals. In this episode:
Are OpenAI and Anthropic reenacting the Fat Protocol Hypothesis Will AI agents cause bank runs optimizing bank balances for yield? If the AI complex bursts does it take down VC? Our tribute to Hester Peirce as she retires from the SEC The SEC and CFTC publish crypto FAQs Vitalik lays out his vision for Ethereum in 2030 Quantum progress is accelerating Illinois delays their crypto transaction tax Is San Francisco better than it was?Weekly Roundup 09/25/26 (Post Clarity rulemaking, Sherrod Brown is back, RIP BitMEX, Coldcard white hats, is EA a cult?)
Matt and Nic are back with another week of news and deals. In this episode:
How loud are America's largest data centers? What's wrong with XAI's data center in Mississippi? The Trump admin is reportedly trying to promote dollar stablecoins Binance invests in Circle We pick up the pieces after Clarity Fairshake plans to spend $30m opposing Sherrod Brown in Ohio How AI anxiety helps the Democrats Sherrod Brown is back to haunt crypto Coinbase is listing IPOs now Are prediction markets out of step with the original vision? BitMEX finally closes its doors 52 BTC were saved from t...Weekly Roundup 09/18/26 (Clarity fails to advance, Caroline Ellison's new job, AI leaking MNPI, Poland's oil snafu)
Matt and Nic are back for another week of news and deals. In this episode:
How is SBF like Dario? The EAs are at it again Do we need new regulation to Pace the Frontier? Can Anthropic be regulated like a bank? Are baseball cards back? Clarity fails at the final hurdle Why did Clarity fail? Stablecoin yield is still in effect The SEC and CFTC are engaging in rulemaking Circle launches Arc, their new L1 Robinhood employees get caught insider trading on Hyperliquid Caroline Ellison is back and working for a former FTX portco Can AI models le...Weekly Roundup 09/11/26 (Liquid hack, AI x-risk, Silvergate revisited, can AI leak MNPI?)
Matt and Nic are back for more deals and news. In this episode:
We bring back his the theme music Anthropic employees think there's a 10% chance AI destroys humanity Was Jacob Coxon astroturfed or real? Are Anthropic employees being sincere or cynical? Blockstream's Liquid sidechain is hacked What does the Liquid hack mean for privacy coins? Hunter Biden launches the $LAPTOP memecoin IONQ says they will be able to crack ECC in two years Ex Silvergate CEO Alan Lane speaks out OpenAI offers a solution to the Navier-Stokes problem Can insider information leak through AI models? Why AI doo...Weekly Roundup 09/04/26 (HuggingFace hack breaks containment, Hyperliquid onshoring, RSA260 factored, is the stablecoin sandwich cheaper?)
Matt and Nic are back for another week of news and deals. In this episode:
We determine the winner of the bad boys theme song competition Dwarkesh ignites controversy with his OpenAI hack recap What actually happened with OpenAI and Huggingface? Gwern's and Matt Huang's short story competition Will AI make us dumb? 200m Americans KYC data has been hacked Prediction markets lawsuit heading to SCOTUS? Robinhood Chain is taking off Strategy is buying Bitcoin again Should Members of Congress be paid more? Cronos suffers a defi hack Revolut gets a bank charter Is the stablecoin sandwich cheaper f...Guy Young (Ethena) on Digital Financial Markets
Wyatt sits down with Guy Young, founder of Ethena, for Guy's third appearance on the pod. In this episode:
What has driven Ethena's success and durability? Where is there demand for other yield assets? Where is capital coming from? Is full onchain portfolio construction possible today? Why tokenize financial products at all? Who are the eventual winners? How is Ethena positioning to an evolving onchain yield landscape?Weekly Roundup 08/28/26 (BankChain alliance, Goat grazing hedges, SHRINCS, is maximalism over?)
Matt and Nic return for another week of deals and news. In this episode:
Matt and Nic consider candidates for the new bad boys intro music 39 state banking associations form the BankChain alliance Blockstream researchers proposed SHRINCS, a PQ signature scheme for Bitcoin How much should depositors care about bank credit risk? Kalshi hosts a prediction market on goat grazing regulation Are trading bot agents getting good? Blockstream proposes SHRINCS for Bitcoin Zcash hits an 8-year high Treasury designates anyone helping Iran's crypto sector AI watermarkingBad boys theme song submissions:
Ian's song Seth's songC...
Weekly Roundup 08/21/26 (SALT Wyoming, SEC's Reg Crypto, Tether's big 4 audit, Crypto Privateers)
Matt and Nic return for another week of news and deals. In this episode:
The boys review SALT Wyoming in Jackson Hole Why did Stripe buy Openrouter? Stripe says we have entered the Singularity People are upset about data centers The SEC proposes Reg Crypto governing token issuance The CFTC convenes a crypto roundtable in Washington FASB proposes treating stablecoins as cash equivalent under GAAP World Liberty gets an OCC charter Trump should divest his WLF tokens to push Clarity through Saylor wriggles out of another jam Tether passes a big 4 audit The White House issues a "crypto p...Weekly Roundup 08/14/26 (Anti-Datacenter sentiment, dinosaur fossil investing, SEC is DIYing Clarity)
Matt and Nic are back for another week of news and deals. In this episode:
Who is the main character in AI? Why are people so mad about datacenters? Sherrod Brown is back and he's running against AI Are datacenters being built with Flock? Culturally scarce goods and dinosaurs are rallying The SEC starts to fill the gap left by the Clarity Act FinCEN ends beneficial ownership reporting The CFTC charges a $400m Ponzi operator Are there successful Ponzi schemers? Is Bitcoin at risk from miners transitioning to AI? The collapse of the diamond marketWeekly Roundup 08/07/26 (Coldcard hack continues, Ethereum mulls an issuance tweak, ai16z winds down, Clarity deadline looms)
Matt and Nic are back with more news and deals. In this episode:
Why the Coldcard hack is worse than some major exchange and DeFi hacks What the Coldcard hack told us about the need for open weight models Is self custody over? MSTR sells more Bitcoin An FBI agent steals $1m in crypto NY state sues Kalshi Ethereum considers another change to issuance Ethereum needs to resist the urge to change monetary policy ai16z's Eliza winds down the merit of reading sci fi The cofounder of Sui leaves for Anthropic Will Anthropic keep the discoveries to t...Weekly Roundup 07/31/26 (Situational Awareness collapse, Coldcard exploit, latest on CLARITY, Ice Cream Kalshi hedges)
Matt and Nic are back for another week of news and deals. In this episode:
What the novel Hyperion tells us about AI doom Situational Awareness liquidates most of its public book after a sharp AI selloff Will Leo have a second act? Why has AI been selling off? Over 1000 BTC stored in Coldcard wallets were stolen due to bad entropy Where does self-custody go from here? What happened with Coldcard? Political winds are shifting against crypto as midterms loom Strategy continues to strengthen its balance sheet with MSTR common sales An ice cream shop in CA is h...Weekly Roundup 07/24/26 (BTC Security Consortium, Genesis' Terra trade, DAT departures, Farewell to BitMEX, Network State drama)
Nic and Matt are back for another week of news and deals. In this episode:
The Fat Model Thesis Are OAI and Anthropic in real trouble with Kimi? The Bitcoin Security Consortium is announced to tackle quantum risk Galaxy announces their Quantum Readiness Initiative Clarity is beleaguered in Washington Polymarket and Kalshi keep feuding The SEC settles with Coinbase over Gensler's lost text messages We uncover some new documents revealing that Genesis inadvertently kicked off the UST depeg Jack Mallers leaves the XXI Capital DAT Movement Labs declares bankruptcy BitMEX finally winds down their exchange Balaji's Network State i...Weekly Roundup 07/17/26 (Teleprompter insider trading, the AI DeFi apocalypse fizzles, NY's datacenter ban)
Matt and Nic are back with the deals and news of the week. In this episode:
Nic licks his World Cup wounds Do Bitcoin Treasury strategies make sense? Trying to make sense of Saylor's "bitcoin rating" Trump's teleprompter operator has been trading on what Trump is going to say in his speeches Why do people keep insider trading on prediction markets? Clarity Act odds are trickling down Strategy shores up their balance sheet Is the Bitcoin cycle finally turning? Stripe bids for Paypal The AI DeFi apocalypse didn't happen Kathy Hochul's AI datacenter moratorium Why is Anthropic running a...Weekly Roundup 07/09/26 (BonkDAO exploit, Choke Point 2.0 extended to audit firms, Kraken v Mazars)
Matt and Nic are back with another week of news and deals. In this episode:
Strategy sells $216m worth of BTC Where does Strategy go from here with STRC? Kalshi's case faces the ban of sports contracts in NY TeraWulf signs a massive lease with Anthropic BonkDAO's legal hack Vanguard hires a head of digital assets Kraken wins arbitration against Mazars for de-auditing them in 2022 Vitalik lays out a new four year plan Polymarket's 5 minute BTC markets are being manipulatedContent mentioned:
Settlement Manipulation in Prediction Markets
Weekly Roundup 07/03/26 (OpenUSD announced, Binance leaves the EU, Strategy's new framework)
Matt and Nic are back with another week of news and deals. In this episode:
Saylor releases Strategy's "Digital Credit Capital Framework" MSTR stabilizes for now though STRC is still discounted Is Saylor transitioning MSTR into a Bitcoin hedge fund? Is Strategy doing anything tricky with their mNAV calculation The OpenUSD consortium is announced Is the Tether and Circle duopoly broken? Can stablecoin consortiums work? What could cause OpenUSD to fail? Trump's 2025 diclosures include a lot of crypto Binance leaves the EU for now The K-pop DAT ends its digital asset ambitions Why the bottom might not be inWeekly Roundup 06/26/26 (Quantum EOs, STRC's selloff, more MSTR)
Matt and Nic are back for another week of news and deals. In this episode:
Our recording snafu STRC's depeg explained Saylor's path forward Why Strategy's issue is the converts Polymarket's questionable marketing Trump's Quantum EOsWeekly Roundup 06/19/26 (STRC under pressure, Illinois' crypto tax, Open weight AI vs the AI boom)
Matt and Nic are back for a week of news and deals. In this episode:
The Tartan Army takes over Boston Europeans are shocked that American infrastructure works STRC falls into the low $80s STRC's liquidation cascade mechanics What are Saylor's options now? Is the US right to put the brakes on Fable? Will open weight models puncture the AI boom? Are we living in a vulnerable world? Kristin Gillebrand's son raises $30m for a perps exchange Make sure your tokenized equity provider has the equity Why aren't publishers doing pay per contentContent mentioned:
Nick B...Weekly Roundup 06/12/26 (Strategy buys the dip, Zcash Orchard bug, eurodollar stablecoins)
Matt and Nic are back with a new week of news and deals. In this episode:
Spanish soccer club Osasuna hedges their relegation on Kalshi Strategy shocks people by buying the dip Is Strategy sacrificing MSTR to save STRC? Saylor bolsters his cash position What factors are dragging on the BTC price? Zcash fixes a scary inflation bug SBF formally applies for a Presidential pardon The CFTC proposes banning a subset of prediction market contracts Polymarket thinks that Kalshi is spying on them European fans in America for the World Cup are discovering Buc-ees The DATs are struggling H...Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics
Wyatt sits down with Omid Malekan, a Professor at Columbia Business School, author of several books, and "Explainer-in-Chief" of blockchain technology. In this episode, Wyatt and Omid discuss:
Why do stablecoins carry a persisent sense of being "dangerous" or "ungovernable? Are stablecoins truly private money? How do we define private money? Who owns our current banking and payment systems? Why do banks vocally oppose stablecoins? Who will own and control digital money networks? Are blockchains the right medium for digital finance over the long term? Is digital trust a problem?Weekly Roundup 06/05/26 (MSTR wobbles, Polymarket's MSTR market, Andrew Left convicted)
Matt and Nic are back for another week of news and deals. In this episode:
FIFA's World Cup ticketing scandal Andrew Yang is now a crypto and telecoms entrepreneur Are Strategy's woes responsible for the Bitcoin pullback? Will Saylor defend STRC or MSTR? What are Saylor's options here? Polymarket has another market resolution SNAFU How UMA could be used to exploit Polymarket BitMine considers a perpetual preferred security Google's quantum circuit is optimized by hobbyists Galaxy launches OTC trading for prediction markets Treasury sanctions Iran's largest digital asset exchanges Andrew Left of Citron research is convicted of securities f...Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland)
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 L...Weekly Roundup 05/22/26 (AI and power bills, SpaceX IPO, Prime Trust clawbacks, USG invests in quantum)
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 t...Weekly Roundup feat. Gus Coldebella 05/15/26 (Clarity advances, Circle's Arc token)
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)
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 f...Weekly Roundup 05/30/26 (DeFi's worst ever month, PTJ on Bitcoin, quantum canaries)
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 p...Pluto (Harbor) on the fate of DeFi after KelpDAO
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...Weekly Roundup 04/24/26 (Finding Satoshi, KelpDAO retrospective, Insider weather betting, Coinbase's Quantum report)
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...Brandon Arvanaghi (Meow) on Banking AI Agents
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...
Weekly Roundup 04/17/26 (BIP361 proposal, SEC's DeFi frontend policy, CSW's Bitcoin movie)
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 c...Weekly Roundup 04/10/26 (New Satoshi candidates, Mythos' 0-days, CZ's memoir)
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 i...Connor Dougherty (Valinor) on the Evolution of Private Credit
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 technologySee more at valinordigital.com
Weekly Roundup 04/03/26 (Two big quantum papers, Drift protocol hack, Maritime Salvage law)
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 BTCContent mentioned in this episode:
Cain et al, Shor's algorithm is p...Weekly Roundup 03/27/26 (Google's Quantum Deadline, Circle's selloff, DATs are selling)
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 W...Weekly Roundup 03/20/26 (Vanity Fair fiasco, SEC token taxonomy, tokenized deposits)
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 closerContent mentioned:
Galaxy Research, Bitcoin Is Rising to the Challenge of Quantum Readiness Global Risk Institute, Quantum T...Weekly Roundup 03/13/26 (SEC vs CFTC detente, prediction market surveillance, equitizing tokens)
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?