On The Brink with Castle Island

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 ar...

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 rep...

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...

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...

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 Qu...

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 S...

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...

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 th...

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 SCOT...

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 on...

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 tradin...

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...

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 ch...

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 mon...

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?...

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 message...

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 sho...

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...

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 stable...

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 EOs

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 Gillebr...

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 ba...

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...

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 p...

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 b...