On The Brink with Castle Island

Hosted by Castle Island Ventures

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Episodes

733

Latest episode

Jun 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

June 12, 2026Episode 72538 min

Weekly Roundup 06/12/26 (Strategy survives, Zcash Orchard bug, the thin model hypothesis) (EP.725)

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 banning a subset of prediction market contracts Polymarket thinks that Kalshi is spying on them European fans in America for the World Cup are discovering Buc-ees The DATs are struggling Hester Peirce gives her farewell address Japanese banks are launching a joint stablecoin Will there be offshore interest-bearing USD stablecoins? Anthropic drops Fable The thin model hypothesis What could pop the AI rally?

June 9, 2026Episode 7241 hr 3 min

Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724)

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 banks vocally oppose stablecoins? Who will own and control digital money networks? Are blockchains the right medium for digital finance over the long term? Is digital trust a problem?

June 5, 2026Episode 72332 min

Weekly Roundup 06/05/26 (MSTR wobbles, Polymarket's MSTR market, Andrew Left convicted) (EP.723)

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 perpetual preferred security Google's quantum circuit is optimized by hobbyists Galaxy launches OTC trading for prediction markets Treasury sanctions Iran's largest digital asset exchanges Andrew Left of Citron research is convicted of securities fraud

May 29, 2026Episode 72243 min

Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland) (EP.722)

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 banks SoFi launches SoFiUSD and mixes a stablecoin with a tokenized deposit Sentiment is bottoming in Ethereum David Hoffman sells his ETH Are stablecoins parasitic to L1s Can L1s accrue value sustainably? The DATs are troubled Is AGI here already? AI cost discipline Content mentioned in this episode: Nic on Substack, Stablecoins are private money. There's nothing wrong with that

May 22, 2026Episode 72135 min

Weekly Roundup 05/22/26 (AI and power bills, SpaceX IPO, Prime Trust clawbacks, USG invests in quantum) (EP.721)

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 OpenAI solved one of the Erdos problems The US government is taking equity stakes in quantum computers Jane Street is still dealing with the Terra fallout Prime Trust is trying to claw back assets from Swan The SEC has questions about tokenized equities Content mentioned in this episode: Nic on Substack, AI is not hiking your electricity bill - yet

May 15, 2026Episode 72024 min

Weekly Roundup feat. Gus Coldebella 05/15/26 (Clarity advances, Circle's Arc token) (EP.720)

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 venture capital Circle is issuing a token Cprkrn recovers 5 BTC with the help of Claude

May 8, 2026Episode 71943 min

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

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 immune from AI job displacement I bipartisan compromise is finally reached on Clarity How the AI water use debate is just like Bitcoin The AI lobby is learning from Fairshake The SEC delays prediction market ETFs

May 1, 2026Episode 71829 min

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

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 stablecoins via Stripe Q-day prize controversy Why quantum canaries might not provide much of a warning Paul Tudor Jones is spooked by quantum Some evidence for insider information in political prediction markets

April 27, 2026Episode 71735 min

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

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 offensive technology for smart contracts? Why protocol exposures are often not on chain Why DeFi might want to segregate execution from settlement Is it possible to have instant settlement and proactive monitoring Do we have anything to learn from DeFi What could Aave have done different? Where did LayerZero go wrong? Can DeFi work if there are occasional freezes and seizures? Pluto's reflections on Thorchain What Thorchain did right Arbitrum's questionable precedent What Pluto is building with Harbor Where does DeFi go from here? Learn more about Harbor and follow Pluto on X

April 24, 2026Episode 71636 min

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

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-anticipated quantum risk report Performance tradeoffs for post-quantum signature schemes SBF was a good investor The Justin Sun WLFI saga continues Did an Indian tanker fall victim to a crypto scam in the Strait of Hormuz? Content mentioned in this episode: Finding Satoshi Documentary Fidelity Digital Assets, Getting Off Zero: Evaluating Bitcoin in 2026 Coinbase, Quantum report

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