On The Brink with Castle Island

Hosted by Castle Island Ventures

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Episodes

742

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Aug 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

August 21, 2026Episode 73533 min

Weekly Roundup 08/21/26 (SALT Wyoming, SEC's Reg Crypto, Tether's big 4 audit, Crypto Privateers) (EP.735)

Matt and Nic return for another week of news and deals. In this episode: The boys review SALT Wyoming in Jackson Hole Why did Stripe buy Openrouter? Stripe says we have entered the Singularity People are upset about data centers The SEC proposes Reg Crypto governing token issuance The CFTC convenes a crypto roundtable in Washington FASB proposes treating stablecoins as cash equivalent under GAAP World Liberty gets an OCC charter Trump should divest his WLF tokens to push Clarity through Saylor wriggles out of another jam Tether passes a big 4 audit The White House issues a "crypto privateer" memo

August 14, 2026Episode 73437 min

Weekly Roundup 08/14/26 (Anti-Datacenter sentiment, dinosaur fossil investing, SEC is DIYing Clarity) (EP.734)

Matt and Nic are back for another week of news and deals. In this episode: Who is the main character in AI? Why are people so mad about datacenters? Sherrod Brown is back and he's running against AI Are datacenters being built with Flock? Culturally scarce goods and dinosaurs are rallying The SEC starts to fill the gap left by the Clarity Act FinCEN ends beneficial ownership reporting The CFTC charges a $400m Ponzi operator Are there successful Ponzi schemers? Is Bitcoin at risk from miners transitioning to AI? The collapse of the diamond market

August 7, 2026Episode 73338 min

Weekly Roundup 08/07/26 (Coldcard hack continues, Ethereum mulls an issuance tweak, ai16z winds down, Clarity deadline looms) (EP.733)

Matt and Nic are back with more news and deals. In this episode: Why the Coldcard hack is worse than some major exchange and DeFi hacks What the Coldcard hack told us about the need for open weight models Is self custody over? MSTR sells more Bitcoin An FBI agent steals $1m in crypto NY state sues Kalshi Ethereum considers another change to issuance Ethereum needs to resist the urge to change monetary policy ai16z's Eliza winds down the merit of reading sci fi The cofounder of Sui leaves for Anthropic Will Anthropic keep the discoveries to themselves? The WSJ gets it wrong on Clarity

July 31, 2026Episode 73238 min

Weekly Roundup 07/31/26 (Situational Awareness collapse, Coldcard exploit, latest on CLARITY, Visions of Bitcoin 8 years on) (EP.732)

Matt and Nic are back for another week of news and deals. In this episode: What the novel Hyperion tells us about AI doom Situational Awareness liquidates most of its public book after a sharp AI selloff Will Leo have a second act? Why has AI been selling off? Over 1000 BTC stored in Coldcard wallets were stolen due to bad entropy Where does self-custody go from here? What happened with Coldcard? Political winds are shifting against crypto as midterms loom Strategy continues to strengthen its balance sheet with MSTR common sales An ice cream shop in CA is hedging the weather with Kalshi Circle buy's IBM's blockchain patent portfolio Visions of Bitcoin turns 8 this week Content mentioned this episode: Nic and Hasu, Visions of Bitcoin

July 24, 2026Episode 73133 min

Weekly Roundup 07/24/26 (BTC Security Consortium, Genesis' Terra trade, DAT departures, Farewell to BitMEX, Network State drama) (EP.731)

Nic and Matt are back for another week of news and deals. In this episode: The Fat Model Thesis Are OAI and Anthropic in real trouble with Kimi? The Bitcoin Security Consortium is announced to tackle quantum risk Galaxy announces their Quantum Readiness Initiative Clarity is beleaguered in Washington Polymarket and Kalshi keep feuding The SEC settles with Coinbase over Gensler's lost text messages We uncover some new documents revealing that Genesis inadvertently kicked off the UST depeg Jack Mallers leaves the XXI Capital DAT Movement Labs declares bankruptcy BitMEX finally winds down their exchange Balaji's Network State is unceremoniously evicted from of Malaysia The SEC warns about crypto vaults Matt comes around on soccer

July 17, 2026Episode 73039 min

Weekly Roundup 07/17/26 (Teleprompter insider trading, the AI DeFi apocalypse fizzles, NY's datacenter ban) (EP.730)

Matt and Nic are back with the deals and news of the week. In this episode: Nic licks his World Cup wounds Do Bitcoin Treasury strategies make sense? Trying to make sense of Saylor's "bitcoin rating" Trump's teleprompter operator has been trading on what Trump is going to say in his speeches Why do people keep insider trading on prediction markets? Clarity Act odds are trickling down Strategy shores up their balance sheet Is the Bitcoin cycle finally turning? Stripe bids for Paypal The AI DeFi apocalypse didn't happen Kathy Hochul's AI datacenter moratorium Why is Anthropic running ads suggesting that they could cause extinction The DTC is using Canton for it's tokenized settlement pilot Brian Chesky's AI slop thread debacle Jesse Pollak leaves Base CBDCs are officially banned federally

July 10, 2026Episode 72929 min

Weekly Roundup 07/09/26 (BonkDAO exploit, Choke Point 2.0 extended to audit firms, Kraken v Mazars) (EP.729)

Matt and Nic are back with another week of news and deals. In this episode: Strategy sells $216m worth of BTC Where does Strategy go from here with STRC? Kalshi's case faces the ban of sports contracts in NY TeraWulf signs a massive lease with Anthropic BonkDAO's legal hack Vanguard hires a head of digital assets Kraken wins arbitration against Mazars for de-auditing them in 2022 Vitalik lays out a new four year plan Polymarket's 5 minute BTC markets are being manipulated Content mentioned: Settlement Manipulation in Prediction Markets

July 3, 2026Episode 72830 min

Weekly Roundup 07/03/26 (OpenUSD announced, Binance leaves the EU, Strategy's new framework) (EP.728)

Matt and Nic are back with another week of news and deals. In this episode: Saylor releases Strategy's "Digital Credit Capital Framework" MSTR stabilizes for now though STRC is still discounted Is Saylor transitioning MSTR into a Bitcoin hedge fund? Is Strategy doing anything tricky with their mNAV calculation The OpenUSD consortium is announced Is the Tether and Circle duopoly broken? Can stablecoin consortiums work? What could cause OpenUSD to fail? Trump's 2025 diclosures include a lot of crypto Binance leaves the EU for now The K-pop DAT ends its digital asset ambitions Why the bottom might not be in

June 26, 2026Episode 72740 min

Weekly Roundup 06/26/26 (Quantum EOs, STRC's selloff, more MSTR) (EP.727)

Matt and Nic are back for another week of news and deals. In this episode: Our recording snafu STRC's depeg explained Saylor's path forward Why Strategy's issue is the converts Polymarket's questionable marketing Trump's Quantum EOs

June 19, 2026Episode 72638 min

Weekly Roundup 06/19/26 (STRC under pressure, Illinois' crypto tax, Open weight AI vs the AI boom) (EP.726)

Matt and Nic are back for a week of news and deals. In this episode: The Tartan Army takes over Boston Europeans are shocked that American infrastructure works STRC falls into the low $80s STRC's liquidation cascade mechanics What are Saylor's options now? Is the US right to put the brakes on Fable? Will open weight models puncture the AI boom? Are we living in a vulnerable world? Kristin Gillebrand's son raises $30m for a perps exchange Make sure your tokenized equity provider has the equity Why aren't publishers doing pay per content Content mentioned: Nick Bostrom, The Vulnerable World Hypothesis