On The Brink with Castle Island

Hosted by Castle Island Ventures

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Episodes

753

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Oct 2026

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About the show

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

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60 recent

October 23, 2026Episode 74632 min

Weekly Roundup 10/23/26 (Gold alchemy, rogue financial AI agents, GENIUS implements stablecoin yield) (EP.746)

Matt and Nic are back with another week of news. In this episode: Marathon Fusion says it has turned mercury into stable gold What would commercially viable alchemy mean for Bitcoin's scarcity argument? AI tools uncover a major vulnerability in PHP A certificate authority's private keys turn out to be trivially guessable Railway warns developers to revoke their secrets after a cyberattack Banks are finding third-party AI agents inside customer accounts Who's responsible when your AI agent acts without instructions? The OCC finalizes its GENIUS Act rules Stablecoin issuers can't pay yield directly, but where does that leave third-party rewards? a16z reportedly plans to drop "crypto" from its flagship fund's name Ali Yahya is leaving to start a company Microsoft, Alphabet, and Goldman Sachs object to tokenized versions of their shares Should public companies have a veto over tokenizing their stock? Polymarket faces growing pains as Kalshi gains ground Are perpetual preferred shares a new source of Bitcoin demand? Can compute derivatives give investors a way to short the AI boom? Content mentioned in this episode: Marathon Fusion, Alchemy OCC, Final Rule to Implement the GENIUS Act Fidelity Digital Assets, Perpetual Preferred Stock: The Newest Demand Catalyst in Bitcoin Bitwise, Q4 2026 Staking Report Wired, The DEA's Premier Crypto Detective: Clues Led Straight to Her Own Family Bloomberg, Polymarket Investors Push CEO Coplan for Change as Kalshi Gains Ground The Wall Street Journal, Want to Short the AI Boom? She Wants to Give You a Way to Bet on Compute Prices

October 16, 2026Episode 74539 min

Weekly Roundup 10/16/26 (OCC debanking report, Google's quantum advance, Ledger spy chips, Richard Heart apprehended) (EP.745)

Matt and Nic are back with another week of news and deals. In this episode: The OCC publishes its debanking findings on America's largest banks Will the banks' fixes satisfy regulators? Google makes another advance in quantum error correction Coinbase lays out its requirements for Bitcoin's post-quantum migration Can Bitcoin's quantum transition accommodate institutional MPC wallets? OpenAI is reportedly in talks to buy Trail of Bits Patrick Witt leaves the White House — where does that leave Clarity? DWF Labs subsidiaries sue BitGo for $141m over allegedly premature token sales Spy chips in reseller-supplied Ledger devices steal recovery phrases Ledger announces an Android device with Solana Mobile Cboe gets approval for binary options on public company metrics The CFTC draws the line between prediction markets and sportsbooks Richard Heart is reportedly detained in Istanbul What's NYC Mayer Zohran Mamdani doing with a quantum computer? Content mentioned in this episode: OCC, Guaranteeing Fair Banking for all Americans Nic on Convergence: quantum risk and AI-driven advances in math Google Quantum AI on magic state cultivation Coinbase, Working Together on BTC Post-Quantum Readiness Jeff Yan on Bloomberg's Odd Lots

October 9, 2026Episode 74437 min

Weekly Roundup 10/09/26 (Going Bunker Mode, classical ECC breaks, AI's math discoveries) (EP.744)

Matt and Nic are back with more deals and news. In this episode: Is it appropriate to have AI manage your fantasy league? Quant firms are hiring "quals" Justin Drake scares everyone in crypto Did AI destroy math? Why a classical ECDSA break would be worse than a quantum one Why we lean forward hash-based signatures for post-quantum Why rotating your address doesn't help now Is Bitcoin the "least of our concerns" if ECC breaks? Nic makes a new scientific discovery with Astra The NFL thinks that gambling should be state regulated What's driving interest in Pokemon cards? Content mentioned in our episode: Coin Metrics, The Death and Life of the Average Memecoin

October 5, 2026Episode 74329 min

Esther Wong (Cashi) on Making Stablecoins Spendable (EP.743)

Esther Wong, founder and CEO of Cashi joins the show. Cashi is a stablecoin spending app and cashback card with a global footprint. In this episode we discuss: Customer personas and use cases for stablecoin payments The future of tokenized equities on chain The landscape of layer one and two blockchains and how these platforms converge with global stablecoin applications Cashi's roadmap and plans for the coming year To learn more about Cashi , visit their website and follow Esther Wong on X .

October 2, 2026Episode 74233 min

Weekly Roundup 10/02/26 (Fat Model Hypothesis, Agentic bank runs, Hester Peirce retires from the SEC, ETH 2030) (EP.742)

Matt and Nic are back with another week of news and deals. In this episode: Are OpenAI and Anthropic reenacting the Fat Protocol Hypothesis Will AI agents cause bank runs optimizing bank balances for yield? If the AI complex bursts does it take down VC? Our tribute to Hester Peirce as she retires from the SEC The SEC and CFTC publish crypto FAQs Vitalik lays out his vision for Ethereum in 2030 Quantum progress is accelerating Illinois delays their crypto transaction tax Is San Francisco better than it was?

September 25, 2026Episode 74133 min

Weekly Roundup 09/25/26 (Post Clarity rulemaking, Sherrod Brown is back, RIP BitMEX, Coldcard white hats, is EA a cult?) (EP.741)

Matt and Nic are back with another week of news and deals. In this episode: How loud are America's largest data centers? What's wrong with XAI's data center in Mississippi? The Trump admin is reportedly trying to promote dollar stablecoins Binance invests in Circle We pick up the pieces after Clarity Fairshake plans to spend $30m opposing Sherrod Brown in Ohio How AI anxiety helps the Democrats Sherrod Brown is back to haunt crypto Coinbase is listing IPOs now Are prediction markets out of step with the original vision? BitMEX finally closes its doors 52 BTC were saved from the Coldcard hack by white hats Is Anthropic privatizing the frontier? A White House memo says effective altruism is a cult Content mentioned in this episode: Nic on Substack, How Noisy are America's Largest Data Centers?

September 18, 2026Episode 74038 min

Weekly Roundup 09/18/26 (Clarity fails to advance, Caroline Ellison's new job, AI leaking MNPI, Poland's oil snafu) (EP.740)

Matt and Nic are back for another week of news and deals. In this episode: How is SBF like Dario? The EAs are at it again Do we need new regulation to Pace the Frontier? Can Anthropic be regulated like a bank? Are baseball cards back? Clarity fails at the final hurdle Why did Clarity fail? Stablecoin yield is still in effect The SEC and CFTC are engaging in rulemaking Circle launches Arc, their new L1 Robinhood employees get caught insider trading on Hyperliquid Caroline Ellison is back and working for a former FTX portco Can AI models leak MNPI? A Polish oil company tried to buy sanctioned oil from Venezuela with USDT The DOE launches a $250m Quantum computing competition

September 11, 2026Episode 73947 min

Weekly Roundup 09/11/26 (Liquid hack, AI x-risk, Silvergate revisited, can AI leak MNPI?) (EP.739)

Matt and Nic are back for more deals and news. In this episode: We bring back his the theme music Anthropic employees think there's a 10% chance AI destroys humanity Was Jacob Coxon astroturfed or real? Are Anthropic employees being sincere or cynical? Blockstream's Liquid sidechain is hacked What does the Liquid hack mean for privacy coins? Hunter Biden launches the $LAPTOP memecoin IONQ says they will be able to crack ECC in two years Ex Silvergate CEO Alan Lane speaks out OpenAI offers a solution to the Navier-Stokes problem Can insider information leak through AI models? Why AI doom is like Pascal's mugging Content mentioned: Alan Lane, Silvergate's Voluntary Liquidation

September 4, 2026Episode 73833 min

Weekly Roundup 09/04/26 (HuggingFace hack breaks containment, Hyperliquid onshoring, RSA260 factored, is the stablecoin sandwich cheaper?) (EP.738)

Matt and Nic are back for another week of news and deals. In this episode: We determine the winner of the bad boys theme song competition Dwarkesh ignites controversy with his OpenAI hack recap What actually happened with OpenAI and Huggingface? Gwern's and Matt Huang's short story competition Will AI make us dumb? 200m Americans KYC data has been hacked Prediction markets lawsuit heading to SCOTUS? Robinhood Chain is taking off Strategy is buying Bitcoin again Should Members of Congress be paid more? Cronos suffers a defi hack Revolut gets a bank charter Is the stablecoin sandwich cheaper for cross border? RSA260 factored - panic? Content mentioned in the episode: GPUworld.com Wenxin Du, Three Myths About Payment Innovation

September 2, 2026Episode 73733 min

Guy Young (Ethena) on Digital Financial Markets (EP.737)

Wyatt sits down with Guy Young, founder of Ethena, for Guy's third appearance on the pod. In this episode: What has driven Ethena's success and durability? Where is there demand for other yield assets? Where is capital coming from? Is full onchain portfolio construction possible today? Why tokenize financial products at all? Who are the eventual winners? How is Ethena positioning to an evolving onchain yield landscape?

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