PLAY PODCASTS
On The Brink with Castle Island

On The Brink with Castle Island

Castle Island Ventures

727 episodesEN

Show overview

On The Brink with Castle Island has been publishing since 2019, and across the 7 years since has built a catalogue of 727 episodes. That works out to roughly 520 hours of audio in total. Releases follow a several-times-a-week cadence.

Episodes typically run thirty-five to sixty minutes — most land between 34 min and 48 min — though episode length varies meaningfully from one episode to the next. It is catalogued as a EN-language Business show.

The show is actively publishing — the most recent episode landed 6 days ago, with 26 episodes already out so far this year. The busiest year was 2020, with 134 episodes published. Published by Castle Island Ventures.

Episodes
727
Running
2019–2026 · 7y
Median length
40 min
Cadence
Several per week

From the publisher

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

Latest Episodes

View all 727 episodes

Weekly Roundup 05/08/26 (Consensus Miami, AI layoffs strike Coinbase, Clarity compromise, AI energy and water use) (EP.719)

May 8, 202643 min

Weekly Roundup 05/30/26 (DeFi's worst ever month, PTJ on Bitcoin, quantum canaries) (EP.718)

May 1, 202629 min

Pluto (Harbor) on the fate of DeFi after KelpDAO (EP.717)

Apr 27, 202635 min

Weekly Roundup 04/24/26 (Finding Satoshi, KelpDAO retrospective, Insider weather betting, Coinbase's Quantum report) (EP.716)

Apr 24, 202636 min

Brandon Arvanaghi (Meow) on Banking AI Agents (EP.715)

Apr 22, 202618 min

Weekly Roundup 04/17/26 (BIP361 proposal, SEC's DeFi frontend policy, CSW's Bitcoin movie) (EP.714)

Apr 17, 202634 min

Weekly Roundup 04/10/26 (New Satoshi candidates, Mythos' 0-days, CZ's memoir) (EP.713)

Apr 10, 202635 min

Connor Dougherty (Valinor) on the Evolution of Private Credit (EP.712)

Apr 9, 202617 min

Ep 711Weekly 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 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

Apr 3, 202635 min

Ep 710Weekly 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 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

Mar 27, 202635 min

Ep 709Weekly 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 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

Mar 20, 202633 min

Ep 708Weekly 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 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?

Mar 13, 202632 min

Ep 707Weekly 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 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

Mar 6, 202631 min

Ep 706Alex Wilson (Cyclops) on Crypto and Stablecoin Payment Solutions (EP.706)

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

Mar 4, 202615 min

Ep 705Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius (EP.705)

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

Mar 3, 202631 min

Ep 704Weekly Roundup 02/27/26 (Insider Predicting, OCC implements GENIUS, ZachXTB fingers Axiom, Jane St vs Terra) (EP.704)

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

Feb 27, 202634 min

Ep 703Weekly Roundup 02/20/26 (CFTC claims Prediction Markets, rogue AI agents, ETH's existential crisis) (EP.703)

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

Feb 20, 202631 min

Ep 702Raj Parekh (Monad Foundation) on Stablecoins and The Next Era of Fintech (EP.702)

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?

Feb 18, 202638 min

Ep 701Weekly Roundup 02/13/26 (SBF wants a retrial, taking stock of Web3, Clarity deadlocked) (EP.701)

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

Feb 13, 202642 min

Ep 700Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700)

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?

Feb 11, 202636 min