Weekly Roundup 10/23/20 (PayPal jumps in, the banks push back at the SPDI, are CBDCs inflationary?) (EP.140)
On The Brink with Castle Island
Release Date: 10/23/2020
Weekly Roundup 03/26/26 (Trump supports stablecoin yield, Kraken’s master account, death prediction markets) (EP.707)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: What Dario Amodei and SBF have in common Trump wades in to the market structure debate and asks the banks to come to the table Why stablecoins are not like banks Kraken Financial gets a skinny Fed master account Visa and Bridge are rolling out stablecoin-linked cards The FBI arrests a suspect accused of stealing $46m in BTC from the US marshalls Morgan Stanley is coming out with their own Bitcoin ETF The Aave token governance controversy rumbles on Kalshi’s traders are upset about their “death market”...
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Alex Wilson (Cyclops) on Crypto and Stablecoin Payment Solutions (EP.706)
On The Brink with Castle Island
Alex Wilson, Co-Founder and CEO of , joins the show. In this episode: Alex’s background running The Giving Block and the company’s acquisition by Shift4 Difficulty in enabling stablecoin solutions when utilizing existing providers while inside of Shift4 Backgrounds of the founding team at Cyclops Regulatory strategy for Cyclops Products: Pay with Crypto (POS, E-Com), Stablecoin Settlement (for Merchants vs. Wire or ACH), Stablecoin Payouts (Payroll, Contractor Payments, Remittance) Key features for building specifically for payments companies See more at
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Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius (EP.705)
On The Brink with Castle Island
and of Paul Hastings join the show. In this episode we discuss: The OCC Charter process how digital asset companies are pursuing the federal path The aftermath of the Genius Act passage and the rulemaking process for this law Considerations for Federal vs. State charter pathways The market structure bill Learn more about
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Weekly Roundup 02/27/26 (Insider Predicting, OCC implements GENIUS, ZachXTB fingers Axiom, Jane St vs Terra) (EP.704)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Kalshi has detected and banned two accounts for insider trading Is Polymarket going to have to add KYC? Is there a tradeoff between informational efficiency and market fairness The OCC de facto bans stablecoin yield in its rulemaking around GENIUS Meta is considering partnering with a stablecoin issuer Stripe is bullish in their annual report ZachXBT determines that Axiom employees have been abusing the platform Terraform labs accuses Jane Street of insider trading WSJ reports that Binance overlooked Iranian...
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Weekly Roundup 02/20/26 (CFTC claims Prediction Markets, rogue AI agents, ETH’s existential crisis) (EP.703)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Crypto VC funds have some dry powder CFTC chair Mike Selig asserts jurisdiction over prediction markets relative to the States Is Kalshi more reliable than interest rate futures? The CLARITY Act inches closer to passing Shake up at Gemini OpenClaw agents are going to start phishing crypto users Bitwise aims to launch prediction market ETFs Bridge gets their OCC charter Hyperliquid launches a lobbying arm DAT hangover continues Blockfills reveals a $75m hole Ethereum is having an identity crisis Base is moving...
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Raj Parekh (Monad Foundation) on Stablecoins and The Next Era of Fintech (EP.702)
On The Brink with Castle Island
Wyatt sits down with Raj Parekh, Head of Stablecoins and Payments at Monad. In this episode: Will enterprises build out their own stablecoin solutions? Will card payments continue to grow, or be challenged by other forms of payments? What is the role of governments in driving whether stablecoin adoption will continue, accelerate, or decelerate? How does Monad work with leading financial organizations? Where do you see opportunity for novel tech solutions around stablecoins? Will there be many stablecoins or a smaller number of stablecoins at scale? Will companies run their own corporate...
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Weekly Roundup 02/13/26 (SBF wants a retrial, taking stock of Web3, Clarity deadlocked) (EP.701)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Matt reflects on the Patriots season We review the Superbowl Ads Looking forward to the OpenAI wearable Is “something big happening” in AI? Does crypto accelerate the rise of malicious AI? Are all communications networks going to break down in 90 days? SBF wants a new trial Blackrock adds BUIDL to Uniswap Blockfills suspends withdrawals Robinhood is internalizing their prediction market product The stablecoin yield issue in Clarity is still a problem Fairshake is getting active in the midterms Is Chris Dixon...
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Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700)
On The Brink with Castle Island
Wyatt sits down with Bhavin, co-founder of Birch Hill to chat about the tokenized asset and DeFi market broadly. In this episode: Who is assessing whether cryptoassets are safe in DeFi today? Who is assessing risk and ensuring assets are solvent and not fraudulent? How have these standards been set and how are they evolving? What is a risk curator, how do risk curators make money, and what is their role? Is it the responsibility of protocols, curators, wallets, or someone else to protect users from buying bad assets? How do you expect non-DeFi-native market participants will start to enter...
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Weekly Roundup 02/06/26 (Bitcoin bloodbath, Digesting Epstein’s Emails, Ethereum rethinks L2s) (EP.699)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Bitcoin grapples with the fallout of the Epstein Emails Did Jeffrey Epstein influence Bitcoin development? Is Bhutan selling their Bitcoin? Do Bitcoin devs care about quantum? Is Bitcoin Core under the influence with sophons Kyle Samani steps back from Multicoin What Samani’s departure means for crypto Is web3 dead forever? Vitalik starts second-guessing the L2-centric roadmap Tether is trading at a slight discount Content mentioned in this episode: Nic on Substack,
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Weekly Roundup 01/30/26 (Fidelity’s FIDD, Gold rally, Worldcoin and AI bots, digital alibis) (EP. 698)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Matt is heated about the Belichick HoF vote Fidelity launches a stablecoin FIDD on Ethereum Market structure passes Senate Ag Cmte The White House crypto council is being revived to find a compromise on stablecoin yield Fairshake has another war chest for the midterms Do stablecoins cause bank deposit contraction? Tether has 140 tons of gold now Why is Bitcoin not participating in the “debasement” trade? Is gold at risk from alchemy? People are still worried about quantum Will Worldcoin save us from AI bots?...
info_outlineMatt and Nic cover deals and news of the week. In this episode:
- PTJ's latest comments on Bitcoin
- How Bitcoin is akin to a cathedral
- Franklin Templeton invests in Curv
- PayPal launches a crypto offering
- Will PayPal open up its walled garden?
- The Kik story finally reaches a conclusion
- Coinbase publishes their first transparency report
- Paradigm's big bet
- Is CBDC going to be pro-inflationary?
- The bank lobby pushes back at the Wyoming SPDI
- Why this bull run is more sustainable than that of 2017
- How Bitcoin scales with capital, not people
Content mentioned in this episode:
- Doubleline, The Pandora's Box of CBDC
- Paul Tudor Jones appears on CNBC
- Coinbase, Transparency at Coinbase
- Forbes, feature on Paradigm
- Raoul Pal, The Bitcoin Life Raft
- Bank Policy Institute, Beware the Kraken