Weekly Roundup 09/16/22 (Merge makes it, Chainalysis crypto adoption report, Starbucks NFTs, Coinbase grades Congress) (EP.350)
On The Brink with Castle Island
Release Date: 09/16/2022
Weekly Roundup 12/19/25 (Quantum FUD, CLARITY markup, are forks obsolete?) (EP.692)
On The Brink with Castle Island
Matt and Nic are back for more deals and news. In this episode: Secret exchange insolvency rumors Caroline Ellison is free David Sacks says CLARITY is getting a markup The Fed rescinds their 2023 Novel Activities Supervision program Insolvent exchange prediction markets Visa’s stablecoin advisory business JPM launches a tokenized Treasury fund MONY Quantum FUD Why Quantum might be a surprise Bitwise 2026 predictions The four year cycle is over Grabby aliens and the Dark Forest Content mentioned in this episode: Talos and Factset,
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Corn (Yearn Finance) on the Evolution of DeFi Protocols (EP. 691)
On The Brink with Castle Island
Henry sits down with , head of business development at , for a conversation about the evolution and current state of defi. In this episode: The history of defi from 2020 to today, and how the TerraLuna crash impacted the market How incentive mechanisms in defi have changed in 2025 What caused the collapse of xUSD and Stream Finance? What is the role of risk curators in defi? The state of onchain cybersecurity and recent hacks What is the appetite for defi from non-crypto users and institutions, and will a declining fed funds rate help? How do defi protocols drive value to their native...
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Weekly Roundup 12/12/25 (Do Kwon sentenced, DTC no action letter, Circle’s private stablecoin) (EP.690)
On The Brink with Castle Island
Matt and Nic are back with more news and deals. In this episode: CIV grows the team Nic does not regret 8 years in crypto People are getting blackpilled about crypto Does speculation in crypto have positive externalities? Matt has never seen LOTR Will web3 ever come back? The OCC lets banks broker crypto trades The Bitwise 10 lists Rushi Manche returns with a fund Circle is launching a private stablecoin The DTC gets a no action letter from the SEC to settle tokenized securities We do a Terra/Luna restrospective Terra’s fatal mistake Oracle mishaps on prediction markets Why did the...
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Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Quantum risk again Are banks filled with spooks? The trouble with Taproot addresses Microstrategy’s dollar reserve Kalshi is going on chain Prediction market predicaments Are insiders monetizing Google search information on Polymarket? Are prediction markets insider trading machines by definition? DAT activist fights Vanguard adds Bitcoin ETFs House Financial Services Committee releases their final report on OCP2.0 What’s going on with leverage in crypto? Are AI agents going to start stealing crypto? Is...
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Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)
On The Brink with Castle Island
, founder of , sits down with Wyatt on today's episode. In this discussion: Squads' evolution from a DeFi-facing product to servicing a broader range of companies' asset treasury needs. What are the pain points of local small-medium businesses? What is driving the gradual global movement from local currencies into USD stablecoins? The appetite for safe yield across user types. Other traditional digital banking players and how they are evolving with technology. How the stablecoin trend impacts governments. What happens to local banks?
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Weekly Roundup 11/27/25 (Who we are thankful for, S&P downgrades Tether) (EP.687)
On The Brink with Castle Island
Matt and Nic record a special Thanksgiving episode of OTB. In this episode: What’s the deal with deep fried turkeys? Polymarket gets CTFC approval Klarna is launching a stablecoin on Tempo Upbit is hacked Berachain drama Tether gets a downgrade from S&P Robinhood is spinning up their own prediction market with Susquehanna Are Visa and Mastercard moving fast enough? Who are we thankful for?
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Weekly Roundup 11/21/25 (Quantum FUD, DAT hangover, stablecoin duration risk) (EP.686)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: Is Quantum FUD causing Bitcoin to sell off? Ray Dalio is worry about Quantum Scott Aaronson is worried about quantum computing Vitalik is worried about quantum Quantum upgrade scenarios Are we still suffering from the flash crash? The DATs are selling DAT spot arbitrage Will the US government end up with the Satoshi coins Should the government bail out AI? Will NFTs come back? IBIT is Harvard’s largest 13F position David Frum on stablecoins Will stablecoins require a bailout?
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Weekly Roundup 11/14/25 (Miran speech, Cash App adds Stables, DAT Hangover)(EP.685)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: The Senate Ag Cmte publishes a Market Structure draft Paul Atkins’ token taxonomy speech Fed Governor Stephen Miran gives a major stablecoin speech Grayscale files their S-1 Coinbase announces a tokensale platform Coinbase is leaving Delaware The Coinbase BVNK deal falls through Visa Direct adds stablecoin support The Czech republic buys Bitcoin DATs are struggling CBDC holdouts Jack Dorsey bends the knee on stablecoins Content mentioned: Stephen Miran,
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Weekly Roundup 11/07/25 (Balancer hack, DATs are suffering, Zcash rally) (EP.684)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Tom Brady’s clone dog We reminisce on the Nic Carter v Mike Green debate Is the government shutdown draining market liquidity? The trouble with Opendimes Balancer hacked Stream finance’s xUSD collapses DATs are selling coins Why is Zcash rallying? Are stablecoins the lightbulb of crypto Content mentioned: JW Verret,
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Keone Hon (Monad Foundation) on Blockchains Built to Scale (EP.683)
On The Brink with Castle Island
, founder of the Foundation joins the show. In this episode: From the point of view of Keone's trading background, what is the promise of blockchains? Reimagining financial systems with blockchains in 2025 Why build Monad, and for anyone using a chain, why use Monad? How the importance of decentralization and chain efficiency becomes underscored during fragile market periods Auto-Deleveraging (ADL): What it is and why it is important. Where is there economic efficiency to be created? How has Keone gone about building a team to tackle this challenge? What would make Monad "successful" in 2-3...
info_outlineMatt and Nic return for another week of news and deals. In this episode:
- The Merge takes place without incident
- Will the Merge silence Ethereum critics on the left?
- Will the ESG narrative around crypto get louder?
- FTX takes a stake in Skybridge
- Castle Island is not an island
- If you make an NFT of a diamond and destroy the diamond, do you still have a diamond?
- CME launches Ether options
- Starbucks launches an NFT loyalty platform
- Tungsten cubes are selling off
- South Korea issues an arrest warrant for Do Kwon
- The thin line between visionary and scammer
- What Terra teaches us about why disclosures matter in capital markets
- Huobi delists privacy coins
- Can you take delivery of Tornado Cash-dusted Ether?
- Coinbase launches their Crypto Action Network
- Matt and Nic evaluate the ratings members of Congress are getting from Coinbase
- Chainalysis releases their 2022 global crypto adoption index
- Hodlnaut’s CSW case begins
- The NSA Bitcoin lab leak hypothesis
- OTB goes live!
Mentioned in this episode:
- Jake Chervinsky's thread on Tornado Cash
- Chainalysis 2022 Global Crypto Adoption Report
Sponsor notes:
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