On The Brink with Castle Island

Jaksot

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  Weekly Roundup 09/11/26 (Liquid hack, AI x-risk, Silvergate revisited, can AI leak MNPI?) (EP.739) 11.09.2026 47min

  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 doom is like Pascal's mugging Content mentioned: Alan Lane, Silvergate's Voluntary Liquidation
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  Weekly Roundup 09/04/26 (HuggingFace hack breaks containment, Hyperliquid onshoring, RSA260 factored, is the stablecoin sandwich cheaper?) (EP.738) 04.09.2026 33min

  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 for cross border? RSA260 factored - panic? Content mentioned in the episode: GPUworld.com Wenxin Du, Three Myths About Payment Innovation  
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  Guy Young (Ethena) on Digital Financial Markets (EP.737) 02.09.2026 33min

  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?
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  Weekly Roundup 08/28/26 (BankChain alliance, Goat grazing hedges, SHRINCS, is maximalism over?) (EP.736) 28.08.2026 35min

  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 watermarking Bad boys theme song submissions: Ian's song Seth's song Content mentioned: Omid Malekan, The banking lobby's bad faith campaign to kill the Clarity Act will backfire Nic Carter, A Second and Final Eulogy for Bitcoin Maximalism  
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  Weekly Roundup 08/21/26 (SALT Wyoming, SEC's Reg Crypto, Tether's big 4 audit, Crypto Privateers) (EP.735) 21.08.2026 33min

  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 privateer" memo
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  Weekly Roundup 08/14/26 (Anti-Datacenter sentiment, dinosaur fossil investing, SEC is DIYing Clarity) (EP.734) 14.08.2026 37min

  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 market 
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  Weekly Roundup 08/07/26 (Coldcard hack continues, Ethereum mulls an issuance tweak, ai16z winds down, Clarity deadline looms) (EP.733) 07.08.2026 38min

  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 themselves? The WSJ gets it wrong on Clarity
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  Weekly Roundup 07/31/26 (Situational Awareness collapse, Coldcard exploit, latest on CLARITY, Visions of Bitcoin 8 years on) (EP.732) 31.07.2026 38min

  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 hedging the weather with Kalshi Circle buy's IBM's blockchain patent portfolio Visions of Bitcoin turns 8 this week  Content mentioned this episode:  Nic and Hasu, Visions of Bitcoin
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  Weekly Roundup 07/24/26 (BTC Security Consortium, Genesis' Terra trade, DAT departures, Farewell to BitMEX, Network State drama) (EP.731) 24.07.2026 33min

  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 is unceremoniously evicted from of Malaysia The SEC warns about crypto vaults Matt comes around on soccer
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  Weekly Roundup 07/17/26 (Teleprompter insider trading, the AI DeFi apocalypse fizzles, NY's datacenter ban) (EP.730) 17.07.2026 39min

  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 ads suggesting that they could cause extinction The DTC is using Canton for it's tokenized settlement pilot Brian Chesky's AI slop thread debacle Jesse Pollak leaves Base CBDCs are officially banned federally
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  Weekly Roundup 07/09/26 (BonkDAO exploit, Choke Point 2.0 extended to audit firms, Kraken v Mazars) (EP.729) 10.07.2026 29min

  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 manipulated Content mentioned: Settlement Manipulation in Prediction Markets  
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  Weekly Roundup 07/03/26 (OpenUSD announced, Binance leaves the EU, Strategy's new framework) (EP.728) 03.07.2026 30min

  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 in
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  Weekly Roundup 06/26/26 (Quantum EOs, STRC's selloff, more MSTR) (EP.727) 26.06.2026 40min

  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
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  Weekly Roundup 06/19/26 (STRC under pressure, Illinois' crypto tax, Open weight AI vs the AI boom) (EP.726) 19.06.2026 38min

  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 content Content mentioned: Nick Bostrom, The Vulnerable World Hypothesis  
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  Weekly Roundup 06/12/26 (Strategy survives, Zcash Orchard bug, the thin model hypothesis) (EP.725) 12.06.2026 38min

  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 Hester Peirce gives her farewell address Japanese banks are launching a joint stablecoin Will there be offshore interest-bearing USD stablecoins? Anthropic drops Fable  The thin model hypothesis What could pop the AI rally?
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  Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724) 09.06.2026 1t 3min

  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?
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  Weekly Roundup 06/05/26 (MSTR wobbles, Polymarket's MSTR market, Andrew Left convicted) (EP.723) 05.06.2026 32min

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

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

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

  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