Claim OwnershipOn The Brink with Castle Island
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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
720 Episodes
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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, 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
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
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
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
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?
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, 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 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
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
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
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?
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
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?
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
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
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 coffin for Web3Social? Where Farcaster went wrong BitGo goes public NYSE is building a tokenized security trading platform Are we looping back around to enterprise blockchains? A MA judge has issued an injunction against Kalshi Jeffries drops Bitcoin from its model portfolio over quantum risk Coinbase launches an advisory board on quantum Trump sues JPM for debanking him Does the Central Bank of Iran really control $500m worth of USDT? What's next for Caroline Ellison?
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 to torpedo Clarity Kontigo is accused of ignoring sanctions X changes its API to block InfoFi California's wealth tax has backfired already BitMine invests $200m into Mr Beast's company Why tokenized deposits aren't as interesting as stablecoins Content mentioned in this episode: Jason Mikula, Kontigo: Y Combinator's Venezuelan Sanctions Evasion Startup
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 continuation of that conversation, exploring what carries value in DeFi going forward, particularly on the back of a shaky market period. This discussion covers: Where does the recent, ongoing market selloff leave us? What metrics matter for onchain markets? What market dynamics contributed to the October 10 washout? How does leverage manifest in onchain markets, and what does it look like today? How do you assess the value of illiquid cryptoassets? What drives revenue multiples. Which protocols will benefit from the tokenization of other asset classes, and which will struggle? How do the individual behaviors and incentives of investment funds contribute to crypto market volatility?
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 continue to bleed out We talk about Nic's fiction story Predictions for 2026 Is there a secret exchange insolvency? What constitutes insider trading for prediction markets? Is the four year cycle finally over? Is it time to try socialfi again? Kickstarter snafus Content mentioned in this episode: Nic Carter, Trillion Dollar Salvage
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