On The Brink with Castle Island
npub142vwspy2vktsdkfa68zpvk22ddch2qjp7ad59d7xxylc9jym76esl3dhnx@drss.io
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
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Weekly Roundup 08/14/26 (Anti-Datacenter sentiment, dinosaur fossil investing, SEC is DIYing Clarity) (EP.734)
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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
Weekly Roundup 08/07/26 (Coldcard hack continues, Ethereum mulls an issuance tweak, ai16z winds down, Clarity deadline looms) (EP.733)
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7 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
Weekly Roundup 07/31/26 (Situational Awareness collapse, Coldcard exploit, latest on CLARITY, Visions of Bitcoin 8 years on) (EP.732)
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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
Weekly Roundup 07/24/26 (BTC Security Consortium, Genesis' Terra trade, DAT departures, Farewell to BitMEX, Network State drama) (EP.731)
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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
Weekly Roundup 07/17/26 (Teleprompter insider trading, the AI DeFi apocalypse fizzles, NY's datacenter ban) (EP.730)
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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
Weekly Roundup 07/09/26 (BonkDAO exploit, Choke Point 2.0 extended to audit firms, Kraken v Mazars) (EP.729)
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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
Weekly Roundup 07/03/26 (OpenUSD announced, Binance leaves the EU, Strategy's new framework) (EP.728)
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3 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
Weekly Roundup 06/26/26 (Quantum EOs, STRC's selloff, more MSTR) (EP.727)
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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
Weekly Roundup 06/19/26 (STRC under pressure, Illinois' crypto tax, Open weight AI vs the AI boom) (EP.726)
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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
Weekly Roundup 06/12/26 (Strategy survives, Zcash Orchard bug, the thin model hypothesis) (EP.725)
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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
Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724)
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9 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: •
Weekly Roundup 06/05/26 (MSTR wobbles, Polymarket's MSTR market, Andrew Left convicted) (EP.723)
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5 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
Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland) (EP.722)
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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
Weekly Roundup 05/22/26 (AI and power bills, SpaceX IPO, Prime Trust clawbacks, USG invests in quantum) (EP.721)
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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
Weekly Roundup feat. Gus Coldebella 05/15/26 (Clarity advances, Circle's Arc token) (EP.720)
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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
Weekly Roundup 05/08/26 (Consensus Miami, AI layoffs strike Coinbase, Clarity compromise, AI energy and water use) (EP.719)
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8 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
Weekly Roundup 05/30/26 (DeFi's worst ever month, PTJ on Bitcoin, quantum canaries) (EP.718)
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1 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
Pluto (Harbor) on the fate of DeFi after KelpDAO (EP.717)
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27 Apr 2026
Pluto (https://x.com/pluto_hbr?s=21) 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
Weekly Roundup 04/24/26 (Finding Satoshi, KelpDAO retrospective, Insider weather betting, Coinbase's Quantum report) (EP.716)
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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
Brandon Arvanaghi (Meow) on Banking AI Agents (EP.715)
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22 Apr 2026
Brandon Arvanaghi, the co-founder and CEO of Meow (https://www.meow.com/), joins the show. In this episode we discuss: • The rise of agentic payments and the convergence of LLMs and financial
Weekly Roundup 04/17/26 (BIP361 proposal, SEC's DeFi frontend policy, CSW's Bitcoin movie) (EP.714)
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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 •
Weekly Roundup 04/10/26 (New Satoshi candidates, Mythos' 0-days, CZ's memoir) (EP.713)
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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
Connor Dougherty (Valinor) on the Evolution of Private Credit (EP.712)
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9 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
Weekly Roundup 04/03/26 (Two big quantum papers, Drift protocol hack, Maritime Salvage law) (EP.711)
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3 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
Weekly Roundup 03/27/26 (Google's Quantum Deadline, Circle's selloff, DATs are selling) (EP.710)
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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
Weekly Roundup 03/20/26 (Vanity Fair fiasco, SEC token taxonomy, tokenized deposits) (EP.709)
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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
Weekly Roundup 03/13/26 (SEC vs CFTC detente, prediction market surveillance, equitizing tokens) (EP.708)
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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
Weekly Roundup 03/26/26 (Trump supports stablecoin yield, Kraken's master account, death prediction markets) (EP.707)
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6 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
Alex Wilson (Cyclops) on Crypto and Stablecoin Payment Solutions (EP.706)
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4 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
Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius (EP.705)
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3 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
Weekly Roundup 02/27/26 (Insider Predicting, OCC implements GENIUS, ZachXTB fingers Axiom, Jane St vs Terra) (EP.704)
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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? •
Weekly Roundup 02/20/26 (CFTC claims Prediction Markets, rogue AI agents, ETH's existential crisis) (EP.703)
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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
Raj Parekh (Monad Foundation) on Stablecoins and The Next Era of Fintech (EP.702)
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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
Weekly Roundup 02/13/26 (SBF wants a retrial, taking stock of Web3, Clarity deadlocked) (EP.701)
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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
Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700)
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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?
Weekly Roundup 02/06/26 (Bitcoin bloodbath, Digesting Epstein's Emails, Ethereum rethinks L2s) (EP.699)
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6 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?
Weekly Roundup 01/30/26 (Fidelity's FIDD, Gold rally, Worldcoin and AI bots, digital alibis) (EP. 698)
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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
Weekly Roundup 01/23/26 (CLARITY stalls, Iran's USDT reserves, Is Web3 Social over?) (EP.697)
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23 Jan 2026
Nic and Matt are back for another week of news and deals. In this episode: • There's a big storm coming • Matt's playoff picks • Farcaster sells to Neynar • Is this the nail in the
Weekly Roundup 01/16/26 (CLARITY problems, InfoFi Dead, CA Wealth Tax, Kontigo) (EP.696)
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16 Jan 2026
Matt and Nic are back after a week off. In this episode: • The Clarity market structure bill markup is delayed for now • Coinbase backs out of supporting Clarity • The bank lobby is trying
Wyatt & Jake Lynch on Onchain Financial Markets (EP.695)
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12 Jan 2026
Wyatt, Henry, and Jake recently put out a report called "Total Value Lost", exploring how best to assess the value of various DeFi markets - starting with lending markets. This episode is a
Weekly Roundup 01/02/26 (2026 predictions, wealth taxes, secret insolvencies) (EP.694)
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2 Jan 2026
Matt and Nic are back for the first OTB show of 2026. In this episode: • Matt's ice rink adventures • The House issues a draft of the PARITY Act • The trouble with wealth taxes • DATs
2025 Highlights and 2026 Predictions with Blockchain Coinvestors (EP.693)
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30 Dec 2025
Matthew Le Merle and Mitch Mechigian of Blockchain Coinvestors join the show. In this episode we discuss: • The top 5 themes of 2025 for the blockchain industry • 2026 predictions and key
Weekly Roundup 12/19/25 (Quantum FUD, CLARITY markup, are forks obsolete?) (EP.692)
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19 Dec 2025
Matt and Nic are back for more deals and news. In this episode: • Secret exchange insolvency rumors • Caroline Ellison is free • David Sacks says CLARITY is getting a markup • The Fed
Corn (Yearn Finance) on the Evolution of DeFi Protocols (EP. 691)
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17 Dec 2025
Henry sits down with Corn (https://x.com/omgcorn), head of business development at Yearn Finance (https://yearn.fi/), for a conversation about the evolution and current state of defi. In this
Weekly Roundup 12/12/25 (Do Kwon sentenced, DTC no action letter, Circle's private stablecoin) (EP.690)
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12 Dec 2025
Matt and Nic are back with more news and deals. In this episode: • CIV grows the team • Nic does not regret 8 years in crypto • People are getting blackpilled about crypto • Does
Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)
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5 Dec 2025
Matt and Nic are back with another week of news and deals. In this episode: • Quantum risk again • Are banks filled with spooks? • The trouble with Taproot addresses • Microstrategy's
Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)
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1 Dec 2025
Stepan, founder of Squads (https://squads.xyz/), sits down with Wyatt on today's episode. In this discussion: • Squads' evolution from a DeFi-facing product to servicing a broader range of
Weekly Roundup 11/27/25 (Who we are thankful for, S&P downgrades Tether) (EP.687)
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28 Nov 2025
Matt and Nic record a special Thanksgiving episode of OTB. In this episode: • What's the deal with deep fried turkeys? • Polymarket gets CTFC approval • Klarna is launching a stablecoin