On The Brink with Castle Island
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Recent Episodes
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 buying the dip Is Strategy…
Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724)
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…
Weekly Roundup 06/05/26 (MSTR wobbles, Polymarket's MSTR market, Andrew Left convicted) (EP.723)
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…
Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland) (EP.722)
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…
Weekly Roundup 05/22/26 (AI and power bills, SpaceX IPO, Prime Trust clawbacks, USG invests in quantum) (EP.721)
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…
Weekly Roundup feat. Gus Coldebella 05/15/26 (Clarity advances, Circle's Arc token) (EP.720)
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.…
Weekly Roundup 05/08/26 (Consensus Miami, AI layoffs strike Coinbase, Clarity compromise, AI energy and water use) (EP.719)
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…
Weekly Roundup 05/30/26 (DeFi's worst ever month, PTJ on Bitcoin, quantum canaries) (EP.718)
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…
Pluto (Harbor) on the fate of DeFi after KelpDAO (EP.717)
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…
Weekly Roundup 04/24/26 (Finding Satoshi, KelpDAO retrospective, Insider weather betting, Coinbase's Quantum report) (EP.716)
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…
Brandon Arvanaghi (Meow) on Banking AI Agents (EP.715)
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…
Weekly Roundup 04/17/26 (BIP361 proposal, SEC's DeFi frontend policy, CSW's Bitcoin movie) (EP.714)
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…
Weekly Roundup 04/17/26 (BIP361 proposal, SEC's DeFi frontend policy, CSW's Bitcoin movie) (EP.714)
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…
Weekly Roundup 04/10/26 (New Satoshi candidates, Mythos' 0-days, CZ's memoir) (EP.713)
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…
Connor Dougherty (Valinor) on the Evolution of Private Credit (EP.712)
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…
Weekly Roundup 04/03/26 (Two big quantum papers, Drift protocol hack, Maritime Salvage law) (EP.711)
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…
Weekly Roundup 03/27/26 (Google's Quantum Deadline, Circle's selloff, DATs are selling) (EP.710)
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…
Weekly Roundup 03/20/26 (Vanity Fair fiasco, SEC token taxonomy, tokenized deposits) (EP.709)
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…
Weekly Roundup 03/13/26 (SEC vs CFTC detente, prediction market surveillance, equitizing tokens) (EP.708)
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…
Weekly Roundup 03/26/26 (Trump supports stablecoin yield, Kraken's master account, death prediction markets) (EP.707)
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…
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On The Brink with Castle Island has published 733 episodes since September 2019, covering topics in Business, Investing.
On The Brink with Castle Island is currently highly active with new episodes weekly. Average episode length is 40m.
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