On The Brink with Castle Island

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

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 themes to monitor To learn more about Blockchain Coinvestors visit fifthera.com/blockchain

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 rescinds their 2023 Novel Activities Supervision program Insolvent exchange prediction markets Visa's stablecoin advisory business JPM launches a tokenized Treasury fund MONY Quantum FUD Why Quantum might be a surprise Bitwise 2026 predictions The four year cycle is over Grabby aliens and the Dark Forest Content mentioned in this episode: Talos and Factset, Year in Review

Henry sits down with Corn, head of business development at Yearn Finance, for a conversation about the evolution and current state of defi. In this episode: The history of defi from 2020 to today, and how the TerraLuna crash impacted the market How incentive mechanisms in defi have changed in 2025 What caused the collapse of xUSD and Stream Finance? What is the role of risk curators in defi? The state of onchain cybersecurity and recent hacks What is the appetite for defi from non-crypto users and institutions, and will a declining fed funds rate help? How do defi protocols drive value to their native tokens? How "decentralized" is defi today?

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 speculation in crypto have positive externalities? Matt has never seen LOTR Will web3 ever come back? The OCC lets banks broker crypto trades The Bitwise 10 lists Rushi Manche returns with a fund Circle is launching a private stablecoin The DTC gets a no action letter from the SEC to settle tokenized securities We do a Terra/Luna restrospective Terra's fatal mistake Oracle mishaps on prediction markets Why did the nation's largest teachers union come out against the Market Structure bill Content mentioned in this episode: Nic Carter and Allen Farrington, All Falls Down

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 dollar reserve Kalshi is going on chain Prediction market predicaments Are insiders monetizing Google search information on Polymarket? Are prediction markets insider trading machines by definition? DAT activist fights Vanguard adds Bitcoin ETFs House Financial Services Committee releases their final report on OCP2.0 What's going on with leverage in crypto? Are AI agents going to start stealing crypto? Is Eliezer Yudkowski to be trusted? AI is going to usher in the golden age of fraud

Stepan, founder of Squads, sits down with Wyatt on today's episode. In this discussion: Squads' evolution from a DeFi-facing product to servicing a broader range of companies' asset treasury needs. What are the pain points of local small-medium businesses? What is driving the gradual global movement from local currencies into USD stablecoins? The appetite for safe yield across user types. Other traditional digital banking players and how they are evolving with technology. How the stablecoin trend impacts governments. What happens to local banks?

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 on Tempo Upbit is hacked Berachain drama Tether gets a downgrade from S&P Robinhood is spinning up their own prediction market with Susquehanna Are Visa and Mastercard moving fast enough? Who are we thankful for?

Matt and Nic are back for another week of news and deals. In this episode: Is Quantum FUD causing Bitcoin to sell off? Ray Dalio is worry about Quantum Scott Aaronson is worried about quantum computing Vitalik is worried about quantum Quantum upgrade scenarios Are we still suffering from the flash crash? The DATs are selling DAT spot arbitrage Will the US government end up with the Satoshi coins Should the government bail out AI? Will NFTs come back? IBIT is Harvard's largest 13F position David Frum on stablecoins Will stablecoins require a bailout?

Matt and Nic are back for another week of news and deals. In this episode: The Senate Ag Cmte publishes a Market Structure draft Paul Atkins' token taxonomy speech Fed Governor Stephen Miran gives a major stablecoin speech Grayscale files their S-1 Coinbase announces a tokensale platform Coinbase is leaving Delaware The Coinbase BVNK deal falls through Visa Direct adds stablecoin support The Czech republic buys Bitcoin DATs are struggling CBDC holdouts Jack Dorsey bends the knee on stablecoins Content mentioned: Stephen Miran, A Global Stablecoin Glut: Implications for Monetary Policy

Matt and Nic are back with another week of news and deals. In this episode: Tom Brady's clone dog We reminisce on the Nic Carter v Mike Green debate Is the government shutdown draining market liquidity? The trouble with Opendimes Balancer hacked Stream finance's xUSD collapses DATs are selling coins Why is Zcash rallying? Are stablecoins the lightbulb of crypto Content mentioned: JW Verret, Comment Letter to Treasury GENIUS ANPR

Keone Hon, founder of the Monad Foundation joins the show. In this episode: From the point of view of Keone's trading background, what is the promise of blockchains? Reimagining financial systems with blockchains in 2025 Why build Monad, and for anyone using a chain, why use Monad? How the importance of decentralization and chain efficiency becomes underscored during fragile market periods Auto-Deleveraging (ADL): What it is and why it is important. Where is there economic efficiency to be created? How has Keone gone about building a team to tackle this challenge? What would make Monad "successful" in 2-3 years?

Wyatt sits down with Giovanni Vignone, the founder of Octane Security, a crypto security platform focused on vetting application code pre-deployment. In this episode we discuss: What poses the greatest threat to crypto right now? How are hackers evolving? What are the important categories of crypto-facing cybersecurity? How much should startup teams be spending on security? How should teams think about counterparty risk? What do you wish early stage teams knew? Where is there room for improved security practices across the industry?

Matt and Nic are back for more news and deals. In this episode: Mastercard buys Zerohash for around $2b Fiserv has a catastrophic day Bitwise launches a Solana staking ETF Is there another regional banking crisis? EthZilla sold some ETH to buy back shares Will there be activists with the DATs? Are prediction markets structurally doomed? Sen Tillis introduces the Ensuring Fair Access to Banking act Could you go back and time and trade effectively? Bessent's great peso trade What's going to happen with Venezuela? We review the Iran-Contra scandal Content mentioned in this episode: Sen Tillis, Fair Access to Banking press release

Geetha Panchapakesan, the founder and CEO of Tesser, joins the show. In this episode: Geetha's background in payments and how she arrived in stablecoins Major shifts across payments over Geetha's career Building a one-stop shop solution for financial institutions, PSPs and MSBs Where FIs are today as it relates to engaging to stablecoins Regulatory tailwinds post-GENIUS See more at tesser.xyz

Matt and Nic are back with another week of news and deals. In this episode: Old fashioned crime is back Quantum risk to Bitcoin More outcry in Washington over the Democratic edits to market structure CZ gets a presidential pardon Federal Reserve announces a payments charter

Matt and Nic are back with another week of news and deals. In this episode: We dissect the market structure behind the flash crash last week What happened with Binance and Ethena? Palmer Luckey's de novo bank Erebor gets an OCC charter Paxos' fat finger The US government has seized $15b in funds tied to pig butchering scams

Wyatt sits down with Pbj, the founder of Perpl, a prominent perpetuals exchange on the imminently launching Monad blockchain. In this episode: How large are perp exchanges in the crypto market? Why perps are attractive to crypto users and traders Hyperliquid's success What assets would people trade on Perpl vs Hyperliquid? What makes Monad unique Perps for other asset classes? Reasons to be excited

Dave Balter, the co-founder and CEO of Flipside Crypto joins the show. In this episode we discuss: How Flipside has shifted its product to fully harness the power of LLMs for analyzing public blockchain networks. Building a product organization in the age of A.I. Perspectives on the evolving landscape of layer one and layer two blockchains. How the role of a data analyst will evolve in the coming years. Where Flipside is focusing its efforts within the blockchain data/analytics segment. To learn more about Flipside visit flipsidecrypto.xyz and follow the company on X.

Matt and Nic are back for another week of news and deals. In this episode: Will stablecoins drive deposit flight from the banks? Is FDIC insurance obsolete? Can CBDCs provide real privacy? ICE invests in Polymarket North Dakota is looking to issue their own "rough rider" stablecoin, joining Wyoming Luxembourg buys bitcoin out of their sovereign wealth fund Is the quantum bubble creating risks for Bitcoin? The "Salomon brothers" OP_RETURN dusting attack on old Bitcoins Reg NMS for blockchains? Katie Porter has a new drama Congress is still working on the market structure bill Shutdown update Content mentioned in this episode: Nic on Substack, Yes, we really do want to trust crypto interests with the future of money Galaxy Research, The Great Bitcoin Dusting: A 'Salomon Brothers' Client Tries to Claim Dormant Wallets

Pelle Braendgaard, the co-founder and CEO of Notabene joins the show. In this episode we discuss: Pelle's background and path to co-founding Notabene. The travel rule and how institutions achieve compliance for blockchain transactions. The launch of Notabene Flow, the first open stablecoin payments platform enabling pull payments for businesses. Views on the evolving market structure for stablecoin payments The state of digital identity. To learn more about Notabene visit notabene.id and follow the company on X.

Mike Cagney, the founder of Figure joins the show. In this episode we discuss: The process of taking Figure public in September 2025. The market structure for tokenized securities. Perspectives on the key issues being debated in the context of The Clarity Act. Reg NMS considerations for blockchain assets. The impact of stablecoins on the banking sector. The original thesis of Figure and the attractiveness of the HELOC market. The Provenance Blockchain Competition versus legacy financial services firms. To learn more about Figure visit figure.com. Follow Mike on X. Follow Figure on X.

Matt and Nic are back for another week of news and deals. In this episode: AI bailed out the mining companies AI people deal with the same energy use claims We reflect on the life of Jane Goodall DoubleZero gets a no-action letter from the SEC Will Tether and Circle lose market share? Who could challenge the Big Two stablecoins? Do optimists always win? Some DATs are troubled Is Kalshi starting to take over? Stripe announces Open Issuance The US Government is shut down Content mentioned: Nic on Substack, The Stablecoin Duopoly is Ending

Wyatt sits down with Ben Ward and Steven Pack of RockSolid. In this episode: What are DeFi vaults? What is RockSolid? Lido vs Rocket Pool Creating effective unified efforts in decentralized communities A look at the wider landscape of DeFi yield How do you measure protocol success? Strengthening the broader Ethereum ecosystem

Mark Coe, the Founder and CIO of Intrinsic Edge Capital Management joins the show. In this episode we discuss: Mark's background and path that led him to founding Intrinsic Edge Capital Management. The Intrinsic Edge Digital Infrastructure Fund, a fund that was launched four years ago to focus on companies in the digital asset ecosystem. Perspectives on the mining industry and the impact of AI/LLMs on this sector of the industry. Views on the types of businesses that will enter the public markets in the coming years. The future of prime brokerage and how service providers will evolve. To learn more about Intrinsic Edge visit intrinsicedge.com or email them at [email protected]