Podcast
On The Brink with Castle Island
Hosted by Castle Island Ventures · EN
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
46episodes
Episodes
Newest firstAll episodes
Weekly Roundup 07/24/26 (BTC Security Consortium, Genesis' Terra trade, DAT departures, Farewell to BitMEX, Network State drama) (EP.731)
2w ago00:33:50Tap to summarizeNic 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
Transcribe →Weekly Roundup 07/17/26 (Teleprompter insider trading, the AI DeFi apocalypse fizzles, NY's datacenter ban) (EP.730)
3w ago00:39:26Tap to summarizeMatt 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
Transcribe →Weekly Roundup 07/09/26 (BonkDAO exploit, Choke Point 2.0 extended to audit firms, Kraken v Mazars) (EP.729)
4w ago00:29:24Tap to summarizeMatt 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
Transcribe →Weekly Roundup 07/03/26 (OpenUSD announced, Binance leaves the EU, Strategy's new framework) (EP.728)
Jul 300:30:29Tap to summarizeMatt 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
Transcribe →Weekly Roundup 06/26/26 (Quantum EOs, STRC's selloff, more MSTR) (EP.727)
Jun 2600:40:22Tap to summarizeMatt 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
Transcribe →Weekly Roundup 06/19/26 (STRC under pressure, Illinois' crypto tax, Open weight AI vs the AI boom) (EP.726)
Jun 1900:38:41Tap to summarizeMatt 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
Transcribe →Weekly Roundup 06/12/26 (Strategy survives, Zcash Orchard bug, the thin model hypothesis) (EP.725)
Jun 1200:38:14Tap to summarizeMatt 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?
Transcribe →Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724)
Jun 901:03:33Tap to summarizeWyatt 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?
Transcribe →Weekly Roundup 06/05/26 (MSTR wobbles, Polymarket's MSTR market, Andrew Left convicted) (EP.723)
Jun 500:32:57Tap to summarizeMatt 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
Transcribe →Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland) (EP.722)
May 2900:43:01Tap to summarizeMatt 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
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