On The Brink with Castle Island
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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Alex Wilson (Cyclops) on Crypto and Stablecoin Payment Solutions
<p >Alex Wilson, Co-Founder and CEO of Cyclops, joins the show. In this episode:</p> 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 <p >See more at cyclops.io</p>
Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius
<p >Dana Syracuse and Josh Boehm of Paul Hastings join the show. In this episode we discuss:</p> 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 <p >Learn more about Paul Hastings </p>
Weekly Roundup 02/27/26 (Insider Predicting, OCC implements GENIUS, ZachXTB fingers Axiom, Jane St vs Terra)
<p>Matt and Nic are back with another week of news and deals. In this episode: </p> 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 sanctions violations Justin Drake u...
Weekly Roundup 02/20/26 (CFTC claims Prediction Markets, rogue AI agents, ETH's existential crisis)
<p>Matt and Nic are back with another week of news and deals. In this episode: </p> 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 away f...
Raj Parekh (Monad Foundation) on Stablecoins and The Next Era of Fintech
<p>Wyatt sits down with Raj Parekh, Head of Stablecoins and Payments at Monad. In this episode:</p> 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 chains? How should companies look at...
Weekly Roundup 02/13/26 (SBF wants a retrial, taking stock of Web3, Clarity deadlocked)
<p>Matt and Nic are back with another week of news and deals. In this episode: </p> 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 right about W...
Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700)
<p>Wyatt sits down with Bhavin, co-founder of Birch Hill to chat about the tokenized asset and DeFi market broadly. In this episode:</p> 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...
Weekly Roundup 02/06/26 (Bitcoin bloodbath, Digesting Epstein's Emails, Ethereum rethinks L2s)
<p>Matt and Nic are back with another week of news and deals. In this episode: </p> 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 <p>Content mentioned in this episode:</p> Nic on Substack, Bitcoin developers are mostly not concerned about quantum risk <p>...
Weekly Roundup 01/30/26 (Fidelity's FIDD, Gold rally, Worldcoin and AI bots, digital alibis)
<p>Matt and Nic are back with another week of news and deals. In this episode: </p> 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 b...
Weekly Roundup 01/23/26 (CLARITY stalls, Iran's USDT reserves, Is Web3 Social over?)
<p>Nic and Matt are back for another week of news and deals. In this episode: </p> There's a big storm coming Matt's playoff picks Farcaster sells to Neynar Is this the nail in the coffin for Web3Social? Where Farcaster went wrong BitGo goes public NYSE is building a tokenized security trading platform Are we looping back around to enterprise blockchains? A MA judge has issued an injunction against Kalshi Jeffries drops Bitcoin from its model portfolio over quantum risk Coinbase launches an advisory board on quantum Trump sues JPM for debanking him Does the Central Bank of Iran r...
