On The Brink with Castle Island cover

On The Brink with Castle Island

Castle Island Ventures

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

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, agents are using stables) (EP.747)

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Weekly Roundup 10/30/26 (Prediction market election hiccups, Hyperliquid onshoring, pubcos push back at tokenization, agents are using stables) (EP.747) 30 Oct 2026

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 public companies be able to opt out of tokenized trading? Canton Strategic Holdings plans to tokenize its own shares Bitcoin Core discloses three bugs found by an AI security scan Does AI make yearlong vulnerability disclosure embargoes obsolete? Category Labs unveils Quantum Cadence, a post-quantum consensus protocol Can fast blockchains accommodate quantum-safe signatures? Strategy shareholders approve daily dividends on its perpetual preferred stocks Datavault AI says it can't withdraw its Bitcoin from Biconomy Y Combinator's latest crypto request for startups Why do Kalshi and Polymarket disagree on the midterms? Content mentioned in this episode: Nic on Coin Stories with Natalie Brunell Category Labs, Quantum Cadence Alex Thorn's Bitcoin bull case Y Combinator, Crypto Request for Startups Coin Metrics, 50 Shades of Gray: Explore Pricing

Weekly Roundup 10/23/26 (Gold alchemy, rogue financial AI agents, GENIUS implements stablecoin yield) (EP.746) 23 Oct 2026

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 its GENIUS Act rules Stablecoin issuers can't pay yield directly, but where does that leave third-party rewards? a16z reportedly plans to drop "crypto" from its flagship fund's name Ali Yahya is leaving to start a company Microsoft, Alphabet, and Goldman Sachs object to tokenized versions of their shares Should public companies have a veto over tokenizing their stock? Polymarket faces growing pains as Kalshi gains ground Are perpetual preferred shares a new source of Bitcoin demand? Can compute derivatives give investors a way to short the AI boom? Content mentioned in this episode: Marathon Fusion, Alchemy OCC, Final Rule to Implement the GENIUS Act Fidelity Digital Assets, Perpetual Preferred Stock: The Newest Demand Catalyst in Bitcoin Bitwise, Q4 2026 Staking Report Wired, The DEA's Premier Crypto Detective: Clues Led Straight to Her Own Family Bloomberg, Polymarket Investors Push CEO Coplan for Change as Kalshi Gains Ground The Wall Street Journal, Want to Short the AI Boom? She Wants to Give You a Way to Bet on Compute Prices

Weekly Roundup 10/16/26 (OCC debanking report, Google's quantum advance, Ledger spy chips, Richard Heart apprehended) (EP.745) 16 Oct 2026

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 over allegedly premature token sales Spy chips in reseller-supplied Ledger devices steal recovery phrases Ledger announces an Android device with Solana Mobile Cboe gets approval for binary options on public company metrics The CFTC draws the line between prediction markets and sportsbooks Richard Heart is reportedly detained in Istanbul What's NYC Mayer Zohran Mamdani doing with a quantum computer? Content mentioned in this episode: OCC, Guaranteeing Fair Banking for all Americans Nic on Convergence: quantum risk and AI-driven advances in math Google Quantum AI on magic state cultivation Coinbase, Working Together on BTC Post-Quantum Readiness Jeff Yan on Bloomberg's Odd Lots

Weekly Roundup 10/09/26 (Going Bunker Mode, classical ECC breaks, AI's math discoveries) (EP.744) 09 Oct 2026

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? Content mentioned in our episode: Coin Metrics, The Death and Life of the Average Memecoin

Esther Wong (Cashi) on Making Stablecoins Spendable (EP.743) 05 Oct 2026

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 year To 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) (EP.742) 02 Oct 2026

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?) (EP.741) 25 Sep 2026

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 the Coldcard hack by white hats Is Anthropic privatizing the frontier? A White House memo says effective altruism is a cult Content mentioned in this episode: Nic on Substack, How Noisy are America's Largest Data Centers?

Weekly Roundup 09/18/26 (Clarity fails to advance, Caroline Ellison's new job, AI leaking MNPI, Poland's oil snafu) (EP.740) 18 Sep 2026

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 leak MNPI? A Polish oil company tried to buy sanctioned oil from Venezuela with USDT The DOE launches a $250m Quantum computing competition

Weekly Roundup 09/11/26 (Liquid hack, AI x-risk, Silvergate revisited, can AI leak MNPI?) (EP.739) 11 Sep 2026

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

Weekly Roundup 09/04/26 (HuggingFace hack breaks containment, Hyperliquid onshoring, RSA260 factored, is the stablecoin sandwich cheaper?) (EP.738) 04 Sep 2026

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

Guy Young (Ethena) on Digital Financial Markets (EP.737) 02 Sep 2026

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?) (EP.736) 28 Aug 2026

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

Weekly Roundup 08/21/26 (SALT Wyoming, SEC's Reg Crypto, Tether's big 4 audit, Crypto Privateers) (EP.735) 21 Aug 2026

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

Weekly Roundup 08/14/26 (Anti-Datacenter sentiment, dinosaur fossil investing, SEC is DIYing Clarity) (EP.734) 14 Aug 2026

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

Weekly Roundup 08/07/26 (Coldcard hack continues, Ethereum mulls an issuance tweak, ai16z winds down, Clarity deadline looms) (EP.733) 07 Aug 2026

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

Weekly Roundup 07/31/26 (Situational Awareness collapse, Coldcard exploit, latest on CLARITY, Visions of Bitcoin 8 years on) (EP.732) 31 Jul 2026

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

Weekly Roundup 07/24/26 (BTC Security Consortium, Genesis' Terra trade, DAT departures, Farewell to BitMEX, Network State drama) (EP.731) 24 Jul 2026

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

Weekly Roundup 07/17/26 (Teleprompter insider trading, the AI DeFi apocalypse fizzles, NY's datacenter ban) (EP.730) 17 Jul 2026

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

Weekly Roundup 07/09/26 (BonkDAO exploit, Choke Point 2.0 extended to audit firms, Kraken v Mazars) (EP.729) 10 Jul 2026

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

Weekly Roundup 07/03/26 (OpenUSD announced, Binance leaves the EU, Strategy's new framework) (EP.728) 03 Jul 2026

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

Weekly Roundup 06/26/26 (Quantum EOs, STRC's selloff, more MSTR) (EP.727) 26 Jun 2026

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

Weekly Roundup 06/19/26 (STRC under pressure, Illinois' crypto tax, Open weight AI vs the AI boom) (EP.726) 19 Jun 2026

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

Weekly Roundup 06/12/26 (Strategy survives, Zcash Orchard bug, the thin model hypothesis) (EP.725) 12 Jun 2026

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?

Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724) 09 Jun 2026

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) (EP.723) 05 Jun 2026

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

Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland) (EP.722) 29 May 2026

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 May 2026

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 May 2026

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 May 2026

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 May 2026

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 Apr 2026

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 Apr 2026

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 Apr 2026

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 Apr 2026

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 Apr 2026

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 Apr 2026

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 Apr 2026

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 Mar 2026

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 Mar 2026

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 Mar 2026

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 Mar 2026

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 Mar 2026

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 Mar 2026

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 Feb 2026

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 Feb 2026

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

Raj Parekh (Monad Foundation) on Stablecoins and The Next Era of Fintech (EP.702) 18 Feb 2026

Wyatt sits down with Raj Parekh, Head of Stablecoins and Payments at Monad. In this episode: Will enterprises build out their own stablecoin solutions? Will card payments continue to grow, or be challenged by other forms of payments? What is the role of governments in driving whether stablecoin adoption will continue, accelerate, or decelerate? How does Monad work with leading financial organizations? Where do you see opportunity for novel tech solutions around stablecoins? Will there be many stablecoins or a smaller number of stablecoins at scale? Will companies run their own corporate chains? How should companies look at embedding stablecoins in their workflows from scratch?

Weekly Roundup 02/13/26 (SBF wants a retrial, taking stock of Web3, Clarity deadlocked) (EP.701) 13 Feb 2026

Matt and Nic are back with another week of news and deals. In this episode: Matt reflects on the Patriots season We review the Superbowl Ads Looking forward to the OpenAI wearable Is "something big happening" in AI? Does crypto accelerate the rise of malicious AI? Are all communications networks going to break down in 90 days? SBF wants a new trial Blackrock adds BUIDL to Uniswap Blockfills suspends withdrawals Robinhood is internalizing their prediction market product The stablecoin yield issue in Clarity is still a problem Fairshake is getting active in the midterms Is Chris Dixon right about Web3? We review winter olympic sports Content mentioned: Chris Dixon, The long game for crypto

Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700) 11 Feb 2026

Wyatt sits down with Bhavin, co-founder of Birch Hill to chat about the tokenized asset and DeFi market broadly. In this episode: Who is assessing whether cryptoassets are safe in DeFi today? Who is assessing risk and ensuring assets are solvent and not fraudulent? How have these standards been set and how are they evolving? What is a risk curator, how do risk curators make money, and what is their role? Is it the responsibility of protocols, curators, wallets, or someone else to protect users from buying bad assets? How do you expect non-DeFi-native market participants will start to enter this market? Will users eventually buy, hold, and sell assets on protocol interfaces, brokerages / exchanges, or risk curator interfaces? Does the Fat Protocol Thesis hold true? Where does value accrue today?

Weekly Roundup 02/06/26 (Bitcoin bloodbath, Digesting Epstein's Emails, Ethereum rethinks L2s) (EP.699) 06 Feb 2026

Matt and Nic are back with another week of news and deals. In this episode: Bitcoin grapples with the fallout of the Epstein Emails Did Jeffrey Epstein influence Bitcoin development? Is Bhutan selling their Bitcoin? Do Bitcoin devs care about quantum? Is Bitcoin Core under the influence with sophons Kyle Samani steps back from Multicoin What Samani's departure means for crypto Is web3 dead forever? Vitalik starts second-guessing the L2-centric roadmap Tether is trading at a slight discount Content mentioned in this episode: Nic on Substack, Bitcoin developers are mostly not concerned about quantum risk

Weekly Roundup 01/30/26 (Fidelity's FIDD, Gold rally, Worldcoin and AI bots, digital alibis) (EP. 698) 30 Jan 2026

Matt and Nic are back with another week of news and deals. In this episode: Matt is heated about the Belichick HoF vote Fidelity launches a stablecoin FIDD on Ethereum Market structure passes Senate Ag Cmte The White House crypto council is being revived to find a compromise on stablecoin yield Fairshake has another war chest for the midterms Do stablecoins cause bank deposit contraction? Tether has 140 tons of gold now Why is Bitcoin not participating in the "debasement" trade? Is gold at risk from alchemy? People are still worried about quantum Will Worldcoin save us from AI bots? What's the solution to the AI slop apocalypse? Digital alibis with blockchains Content mentioned in this episode: Niall Ferguson and Manny Rincon-Cruz, Stablecoins Are the Future but Banks will Survive McKinsey and Artemis, Stablecoins in payments: What the raw transaction numbers miss