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
Weekly Roundup 02/20/26 (CFTC claims Prediction Markets, rogue AI agents, ETH's existential crisis) (EP.703)
20 Feb 2026
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
Raj Parekh (Monad Foundation) on Stablecoins and The Next Era of Fintech (EP.702)
18 Feb 2026
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
Weekly Roundup 02/13/26 (SBF wants a retrial, taking stock of Web3, Clarity deadlocked) (EP.701)
13 Feb 2026
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
Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700)
11 Feb 2026
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?
Weekly Roundup 02/06/26 (Bitcoin bloodbath, Digesting Epstein's Emails, Ethereum rethinks L2s) (EP.699)
6 Feb 2026
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?
Weekly Roundup 01/30/26 (Fidelity's FIDD, Gold rally, Worldcoin and AI bots, digital alibis) (EP. 698)
30 Jan 2026
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
Weekly Roundup 01/23/26 (CLARITY stalls, Iran's USDT reserves, Is Web3 Social over?) (EP.697)
23 Jan 2026
Nic and Matt are back for another week of news and deals. In this episode: • There's a big storm coming • Matt's playoff picks • Farcaster sells to Neynar • Is this the nail in the
Weekly Roundup 01/16/26 (CLARITY problems, InfoFi Dead, CA Wealth Tax, Kontigo) (EP.696)
16 Jan 2026
Matt and Nic are back after a week off. In this episode: • The Clarity market structure bill markup is delayed for now • Coinbase backs out of supporting Clarity • The bank lobby is trying
Wyatt & Jake Lynch on Onchain Financial Markets (EP.695)
12 Jan 2026
Wyatt, Henry, and Jake recently put out a report called "Total Value Lost", exploring how best to assess the value of various DeFi markets - starting with lending markets. This episode is a
Weekly Roundup 01/02/26 (2026 predictions, wealth taxes, secret insolvencies) (EP.694)
2 Jan 2026
Matt and Nic are back for the first OTB show of 2026. In this episode: • Matt's ice rink adventures • The House issues a draft of the PARITY Act • The trouble with wealth taxes • DATs
2025 Highlights and 2026 Predictions with Blockchain Coinvestors (EP.693)
30 Dec 2025
Matthew Le Merle and Mitch Mechigian of Blockchain Coinvestors join the show. In this episode we discuss: • The top 5 themes of 2025 for the blockchain industry • 2026 predictions and key
Weekly Roundup 12/19/25 (Quantum FUD, CLARITY markup, are forks obsolete?) (EP.692)
19 Dec 2025
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
Corn (Yearn Finance) on the Evolution of DeFi Protocols (EP. 691)
17 Dec 2025
Henry sits down with Corn (https://x.com/omgcorn), head of business development at Yearn Finance (https://yearn.fi/), for a conversation about the evolution and current state of defi. In this
Weekly Roundup 12/12/25 (Do Kwon sentenced, DTC no action letter, Circle's private stablecoin) (EP.690)
12 Dec 2025
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
Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)
5 Dec 2025
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
Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)
1 Dec 2025
Stepan, founder of Squads (https://squads.xyz/), sits down with Wyatt on today's episode. In this discussion: • Squads' evolution from a DeFi-facing product to servicing a broader range of
Weekly Roundup 11/27/25 (Who we are thankful for, S&P downgrades Tether) (EP.687)
28 Nov 2025
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
Weekly Roundup 11/21/25 (Quantum FUD, DAT hangover, stablecoin duration risk) (EP.686)
21 Nov 2025
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
Weekly Roundup 11/14/25 (Miran speech, Cash App adds Stables, DAT Hangover)(EP.685)
14 Nov 2025
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
Weekly Roundup 11/07/25 (Balancer hack, DATs are suffering, Zcash rally) (EP.684)
7 Nov 2025
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
Keone Hon (Monad Foundation) on Blockchains Built to Scale (EP.683)
5 Nov 2025
Keone Hon (https://www.linkedin.com/in/keone-hon), founder of the Monad (https://www.monad.xyz/) Foundation joins the show. In this episode: • From the point of view of Keone's trading
Giovanni Vignone (Octane Security) on Protecting Onchain Assets (EP.682)
3 Nov 2025
Wyatt sits down with Giovanni Vignone, the founder of Octane Security, a crypto security platform focused on vetting application code pre-deployment. In this episode we discuss: • What poses the
Weekly Roundup 10/31/25 (DATs selling coins, prediction market problems, Bessent's pesos) (EP.681)
31 Oct 2025
Matt and Nic are back for more news and deals. In this episode: • Mastercard buys Zerohash for around $2b • Fiserv has a catastrophic day • Bitwise launches a Solana staking ETF • Is
Geetha Panchapakesan (Tesser) on Enabling FIs to Utilize Stablecoins (EP.680)
29 Oct 2025
Geetha Panchapakesan, the founder and CEO of Tesser, joins the show. In this episode: • Geetha's background in payments and how she arrived in stablecoins • Major shifts across payments
Weekly Roundup 10/24/25 (Quantum, Crypto Pardons, Fed Payment Accounts) (EP.679)
24 Oct 2025
Matt and Nic are back with another week of news and deals. In this episode: • Old fashioned crime is back • Quantum risk to Bitcoin • More outcry in Washington over the Democratic edits
Weekly Roundup 10/17/25 (Flash crash, pig butchering scam busted, Erebor charter granted) (EP.678)
17 Oct 2025
Matt and Nic are back with another week of news and deals. In this episode: • We dissect the market structure behind the flash crash last week • What happened with Binance and Ethena? •
Pbj (Perpl) on the Perp DEX Market & Monad's Imminent Launch (EP.677)
14 Oct 2025
Wyatt sits down with Pbj, the founder of Perpl, a prominent perpetuals exchange on the imminently launching Monad blockchain. In this episode: • How large are perp exchanges in the crypto
Dave Balter (Flipside) on the convergence of AI and Blockchain Analytics (EP.676)
13 Oct 2025
Dave Balter, the co-founder and CEO of Flipside Crypto (https://flipsidecrypto.xyz/home/) joins the show. In this episode we discuss: • How Flipside has shifted its product to fully harness the
Weekly Roundup 10/10/25 (Luxembourg buys BTC, N. Dakota’s stablecoin, Salomon bros dust attack) (EP.675)
10 Oct 2025
Matt and Nic are back for another week of news and deals. In this episode: • Will stablecoins drive deposit flight from the banks? • Is FDIC insurance obsolete? • Can CBDCs provide real
Pelle Braendgaard on the Notabene Flow payments platform (EP.674)
8 Oct 2025
Pelle Braendgaard, the co-founder and CEO of Notabene (https://notabene.id/) joins the show. In this episode we discuss: • Pelle’s background and path to co-founding Notabene. • The travel
Mike Cagney (Figure) on Blockchain Capital Markets (EP.673)
7 Oct 2025
Mike Cagney (https://x.com/mcagney), the founder of Figure joins the show. In this episode we discuss: • The process of taking Figure public in September 2025. • The market structure for
Weekly Roundup 01/27/23 (Modulo Capital, PoR legislation, Tungsten mounts a comeback ) (EP.392)
27 Jan 2023
Matt and Nic return for another week of news and deals. In this episode: • Is there a socially optimal level of vigilantism • What's the deal with Modulo Capital? • SBF's mother and
Maneesh Gandhi & Michael Liddy (Evanston Capital) on The Institutional Allocator Landscape (EP.391)
25 Jan 2023
Maneesh Gandhi and Michael Liddy of Evanston Capital join the show. In this episode we discuss: • Evanston Capital’s history and thoughts on the blockchain ecosystem • Their views on the
Dhruv Patel and Himanshu Sahay (Arch) on Building a New Alternative Lender (EP.390)
23 Jan 2023
Arch (https://www.archlending.com/) cofounders Dhruv Patel (https://www.linkedin.com/in/dhruv-patel-34166163/) and Himanshu Sahay (https://twitter.com/hhsahay) • Arch coming out of stealth
Weekly Roundup 01/20/23 (DOJ takes down Bitzlato, loyalty point inflation, FTX US still solvent?) (EP.389)
20 Jan 2023
Matt and Nic return for another week of news and deals. In this episode: • What’s going on with our merch? • Nic’s pitch for pickleball • What’s the deal with the leaked GTX pitch
Tony Scuderi (Imperii) on Crypto Banking and Advisory (EP.388)
18 Jan 2023
Tony Scuderi, the founder of Imperii Partners joins the show. In this episode we discuss: • The investment banking landscape for crypto/blockchain companies. • How the fundraising environment
Luuk Strijers (Deribit) on a New Model for Proof of Reserves (EP.387)
17 Jan 2023
Deribit (https://www.deribit.com/) Chief Commercial Officer Luuk Strijers joins the show to talk about their new Proof of Reserve rollout. In this episode: • Why Deribit decided to do a PoR
Weekly Roundup 01/13/23 (Nexo raided, crypto charity boxing, DCG vs Gemini II) (EP.386)
13 Jan 2023
Matt and Nic return for another week of news and deals. In this episode: • What’s happening with Proof of Reserves? • Will BTC and ETH have another fee crisis? • Nishad Singh has met
Weekly Roundup 01/06/23 (DCG vs Gemini, SBF's plea, India's crypto framework) (EP.385)
6 Jan 2023
Matt and Nic return for another week of news and deals. In this episode: • A call for on-chain archeology • Nic’s scuppered NYE plans • More news from the FTX crime family • Who is
Weekly Roundup 12/30/22 (Avi Eisenberg arrest, weather affects the hashrate, our predictions for 2023) (EP.384)
30 Dec 2022
Nic and Matt return for another week of news and deals. In this episode: • Galaxy acquires the Helios miner facility from Argo • Consolidating in the miner space • A new bad boy bursts
Weekly Roundup 12/23/22 (Caroline pleads, SBF is extradited, Visa’s autopayments) (EP.383)
23 Dec 2022
Matt and Nic return for another week of news and deals. In this episode: • Are stablecoins still a priority in DC? • The rise of the FUDfluencer • Sam agrees to be extradited • Did
Rep. Tom Emmer (R-MN) on FTX, the SEC, and the House Crypto Agenda for 2023 (EP.382)
20 Dec 2022
Minnesota Representative and newly elected House Whip Tom Emmer joins the show for a discussion of the FTX fallout, the House hearings, the SEC’s behavior throughout the process, and developments
Weekly Roundup 12/16/22 (SBF Arrest, Binance’s ‘Bank run’, Gensler, FTX, and IEX) (EP.381)
16 Dec 2022
Matt and Nic are back for another wild week of news and deals. In this episode: • Is SBF currently interned in a top 5 prison on earth? • SBF is finally arrested • We enumerate the
Weekly Roundup 12/08/22 (FTX’s Venture Portfolio, SBF’s mining investment, BlockFi retrospective) (EP.380)
9 Dec 2022
Matt and Nic return for another episode of news and deals. In this episode: • Brink Nation’s surprising fan club in Bali • We investigate FTX’s leaked private equity portfolio • FTX
John Palmer (CBOE Digital) on Regulated Digital Asset Derivatives (EP.379)
7 Dec 2022
John Palmer, the CEO of CBOE Digital joins the show. In this episode we discuss: • John’s career and the path that led him to CBOE Digital. • The history of CBOE Digital, including the
Robert Miller (Flashbots) on Decentralizing Block Building with SUAVE (EP.378)
5 Dec 2022
In this episode, Ria is joined by Robert Miller, Steward at Flashbots, which is a research and development organization with the aim to reduce the negative externalities and risks posed by MEV, or
Weekly Roundup 12/01/22 (Is SBF playing the media, more Bad Boys, Binance’s Proof of Reserve) (EP.377)
1 Dec 2022
Matt and Nic are back for another week of news and deals. In this episode: • Tether collapse scenarios • The wrapped Bitcoin issue • Ria and others are named Forbes 30 under 30 • Sam
Mahesh Ramakrishnan (Escape Velocity) on Decentralized Wireless (EP.376)
30 Nov 2022
Mahesh Ramakrishnan of Escape Velocity joins the show. In this episode we discuss: • Mahesh’s career in traditional financial services and the path that led him to launching Escape Velocity.
Mike Belshe (BitGo) on FTX and the impact on crypto market structure (EP.375)
28 Nov 2022
Mike Belshe, co-founder and CEO of BitGo joins the show. In this episode we discuss: • Mike’s thoughts on FTX and the unfolding fraud case. • His views on crypto market structure and how it
Weekly Roundup 11/24/22 (SBF is at large, DCG’s fate, what we are thankful for) (EP.374)
24 Nov 2022
Matt and Nic return for a Thanksgiving episode of OTB. In this episode: • Liz Warren writes her first good letter ever? • SBF is striking a defiant tone • Sam’s new letter to employees