Weekly Roundup 06/26/26 (Quantum EOs, STRC's selloff, more MSTR) (EP.727)
On The Brink with Castle Island
Release Date: 06/26/2026
Weekly Roundup 07/03/26 (OpenUSD announced, Binance leaves the EU, Strategy’s new framework) (EP.728)
On The Brink with Castle Island
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...
info_outline
Weekly Roundup 06/26/26 (Quantum EOs, STRC's selloff, more MSTR) (EP.727)
On The Brink with Castle Island
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
info_outline
Weekly Roundup 06/19/26 (STRC under pressure, Illinois’ crypto tax, Open weight AI vs the AI boom) (EP.726)
On The Brink with Castle Island
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, ...
info_outline
Weekly Roundup 06/12/26 (Strategy survives, Zcash Orchard bug, the thin model hypothesis) (EP.725)
On The Brink with Castle Island
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...
info_outline
Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724)
On The Brink with Castle Island
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?
info_outline
Weekly Roundup 06/05/26 (MSTR wobbles, Polymarket’s MSTR market, Andrew Left convicted) (EP.723)
On The Brink with Castle Island
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 Galaxy launches OTC trading for prediction markets Treasury sanctions Iran’s largest digital asset exchanges Andrew Left of...
info_outline
Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland) (EP.722)
On The Brink with Castle Island
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...
info_outline
Weekly Roundup 05/22/26 (AI and power bills, SpaceX IPO, Prime Trust clawbacks, USG invests in quantum) (EP.721)
On The Brink with Castle Island
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...
info_outline
Weekly Roundup feat. Gus Coldebella 05/15/26 (Clarity advances, Circle’s Arc token) (EP.720)
On The Brink with Castle Island
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
info_outline
Weekly Roundup 05/08/26 (Consensus Miami, AI layoffs strike Coinbase, Clarity compromise, AI energy and water use) (EP.719)
On The Brink with Castle Island
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...
info_outlineMatt 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