On The Brink with Castle Island

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...

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 stable...

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

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 Gillebr...

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 ba...

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...

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 p...

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 b...

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 OpenA...

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...

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 i...

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 s...

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 offens...

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-anti...

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...

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...

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 fi...

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 cred...

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...

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-backe...

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 mainne...

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...

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 BT...

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...

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