On The Brink with Castle Island

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

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 s

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

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

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

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 r

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

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 Mississ

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

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 Frontie

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

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 W

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

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

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

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 the

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

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 association

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

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 hav

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

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 b

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

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

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

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

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

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 C

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

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 se

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

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

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

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 thoug

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

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

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

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 fa

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

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 buyin