Castle Island Ventures
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
Author
Castle Island Ventures
Category
Podcast website
Latest episode
Jul 10, 2026
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Episodes
Weekly Roundup 12/08/22 (FTX's Venture Portfolio, SBF's mining investment, BlockFi retrospective) (EP.380) 09.12.2022 58:22
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 employees were raising LP money for funds from FTX Why was FTX acting as a fund of funds? What is modulo capital The Michael Lewis - IEX - FTX troika Why did FTX invest $1b+ in Genesis Digital Assets? SBF's possible incenti...
John Palmer (CBOE Digital) on Regulated Digital Asset Derivatives (EP.379) 07.12.2022 38:59
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 acquisition of ErisX and the company's recent funding round. CBOE Digital's product approach. The regulatory landscape in the United States and how CBOE is positioned vs. offshore unregulated venues. The impact of the F...
Robert Miller (Flashbots) on Decentralizing Block Building with SUAVE (EP.378) 05.12.2022 1:18:33
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 maximal extractable value. We cover: The MEV supply chain and how it's evolved as Ethereum transitioned from Proof of Work to Proof of Stake The new challenges and risk vectors that have emerged as a res...
Weekly Roundup 12/01/22 (Is SBF playing the media, more Bad Boys, Binance's Proof of Reserve) (EP.377) 01.12.2022 48:01
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 is still not in jail Sam's hidden media strategy How Sam could be positioning himself for the case Was FTX really a case of negligence or was it fraud? Sam is muddying the waters Sam Trubucco is our bad boy of the week Shoul...
Mahesh Ramakrishnan (Escape Velocity) on Decentralized Wireless (EP.376) 30.11.2022 36:43
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. The decentralized wireless market and how it is likely to evolve. How tokenized protocols and USD stablecoins are likely to play a role in this evolution. How incumbents are positioned in this emerging category....
Mike Belshe (BitGo) on FTX and the impact on crypto market structure (EP.375) 28.11.2022 38:06
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 is likely to evolve in the face of the FTX collapse. The regulatory landscape and the path forward for spot market regulation. Views on the MPC custody landscape and advances in zero knowledge cryptography. To lear...
Weekly Roundup 11/24/22 (SBF is at large, DCG's fate, what we are thankful for) (EP.374) 24.11.2022 43:40
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 Is the Alameda/FTX situation really that complicated? Sam's parents bought tens of millions worth of Bahamas property The Bahamas steps in and seizes some funds Should the US annex the Bahamas? Should the US use 'extraor...
Travis Scher on the FTX impact on Crypto VC (EP.373) 21.11.2022 32:15
Travis Scher, co-founder of North Island Ventures joins the show. In this episode we discuss: Travis' investing career including his tenure at DCG and his path to founded North Island Ventures. How Travis initially met SBF and his reasons for passing on the deal. Analysis of the bankruptcy process and the likely second order impacts. How this event will change the early crypto VC landscape. To lea...
Weekly Roundup 11/17/22 (John Ray's FTX filing, will FTX political contributions be repaid, what's wrong with effective altruism?) (EP.372) 18.11.2022 44:16
Matt and Nic return for another week of news and deals. In this episode: Matt's blog post, 'It's Time to Grow Up' The Alameda - FTX relationship was always sketchy Would FTX ever have been able to go public? Why don't we have decent disclosure for token emissions? How do we put this crisis to use? John Ray's Day 1 filing about the state of affairs at FTX So what in the hell happened to the client...
Garrett Weaver (Juke) on Digital Collectibles (EP.371) 17.11.2022 33:19
Garrett Weaver, the co-founder and CEO of Juke joins the show. In this episode we discuss: Garrett's career as an entertainment industry executive and the path that led him to starting Juke. How Hollywood intellectual property works and how blockchains can open up revenue opportunities for studios. The use cases for NFT technology and the innovation on the horizon in the industry. To learn more ab...
Weekly Roundup 11/10/22 (FTX fiasco, Su Zhu and Do attempt comebacks, Proof of Reserves redemption) (EP.370) 10.11.2022 56:00
Nic and Matt return for one of the craziest weeks in crypto history. In this episode: Coin Metrics makes a key on-chain discovery regarding FTX's insolvency Will Castle Island buy the naming rights to the Miami Heat arena? What in the hell happened to FTX/Alameda? How big is the hole in FTX' balance sheet Was FTX/Alameda insolvent as early as Q2? How this is reminiscent of the Bitfinex/Tether tra...
Josh Schwartz and Dima Kogan (FORDEFI) on Building Institutional Custody for DeFi (EP.369) 08.11.2022 35:31
Josh Schwartz and Dima Kogan, co-founders of Fordefi , join the show. In this episode we discuss: MPC custody: what it is, its academic roots and how MPC works. The tradeoffs and considerations that have led to the growth in popularity of MPC custody. Josh and Dima's backgrounds and the path that led them to founding Fordefi. The institutional custody landscape and some of the challenges that firm...
Weekly Roundup 11/04/22 (Fidelity Crypto Launches, Alameda's balance sheet, SDNY looks at Tether) (EP.368) 04.11.2022 50:53
Matt and Nic return for another week of deals and news. In this episode: Bitwise is moving into active management What's the deal with Uber on the blockchain? The boys review House of the Dragon The history of land-based blockchain bets Fidelity launches no-fee retail trading for trading BTC and ETH on their platform Matt reminisces on Fidelity's crypto journey Google announces blockchain node en...
Jeff Park (Bitwise) on Active Management in Crypto (EP.367) 01.11.2022 36:53
Jeff Park, an active Portfolio Manager at Bitwise joins the show. In this episode we discuss: The state of active crypto asset management. How Bitwise approaches the active management opportunity. The taxonomy of strategies that Jeff observes in the market. Perspectives on MEV and other crypto specific opportunities. The institutional LP landscape for active management vs. passive. To learn more a...
Brian Venturo and Brannin McBee (CoreWeave) on Building an Industrial Scale GPU Cloud (EP.366) 31.10.2022 1:01:22
CoreWeave 's Brian Venturo (CTO) and Brannin McBee (CSO) return to On The Brink for a discussion of their journey through the merge and beyond. In this episode: Are they relieved that the merge finally happened? Will there be some form of non-Bitcoin PoW in the future? Could Ethereum conceivably return to PoW? The effect of PoS on ETH's censor resistance What quantity of ETH miners shifted to oth...
Roundup 10/28/22 (Bitcoin's hashrate spike, Miner insolvencies, Lightning v Rollups) (EP.365) 28.10.2022 39:59
Matt and Nic are back for another week of deals and news. In this episode: Full time crypto haters What's the deal with the nocoiner think tank? Eric Wall and Udi vs Bitcoiners Did Bitcoin put all of its eggs in the LN basket? Scaling isn't LN versus big blocks any more Is there just one scaling solution for blockchains? What are the prospects for ZK Rollups on Bitcoin? Spam attacks on BSV and Zc...
Mike Cahill (Pyth) on Solving the Oracle Problem (EP.364) 24.10.2022 34:33
Mike Cahill , Director of the Pyth Data Association joins the show. In this episode we discuss: The origin of Pyth and how the project is addressing the 'Oracle Problem'. How Pyth works and how companies and protocols are using the product today. Mike's views on how equities on chain will evolve, and how Pyth is positioned in this market. The recent Mango Markets exploit and the future of on-chain...
Weekly Roundup 10/21/22 (Aptos launch, crypto vigilantes, FTX's regulatory draft) (EP.363) 21.10.2022 50:49
Matt and Nic return for news and deals of the week. In this episode: Why USDC is suffering redemptions but not USDT Some new 3AC shenanigans are unearthed The SEC and CFTC are investigating 3AC Details from the Voyager bankruptcy filing Avraham Eisenburg is crypto's hottest new villain Is the Mango exploit against the law? Is there a vigilante group out to get Do Kwon? SBF is criticized for his r...
Blake King (Galaxy Digital) on Mining, Transmission, and Curtailment (EP.362) 17.10.2022 1:14:07
For another episode of the mining miniseries, Nic sits down with Blake King , power markets engineer at Galaxy Digital, for his second OTB appearance. In this episode: Blake reacts to the White House OSTP report on crypto mining Does mining actually reduce the incentive for utilities to build additional transmission? How transmission building decisions get made How are ERCOT planners taking the p...
Weekly Roundup 10/13/22 (FASB accounting rules update, Warren's letter to Texas, Howey's orange groves) (EP.361) 14.10.2022 41:16
Matt and Nic are back for another week of deals and news. In this episode: What is XEN and why is it driving up ETH fees? Bittrex settles with OFAC SEC is investigating Yuga labs Mango and Binance Smart Chain are hacked The FASB settles on fair value accounting for cryptoassets Warren writes a letter to Texas about mining Coin Center is suing OFAC Sponsor notes: Talos powers institutional access...
Rob Behnke (Halborn) on Public Blockchain Cybersecurity (EP.360) 12.10.2022 40:20
Rob Behnke, co-founder and CEO of Halborn joins the show. In this episode we discuss: Rob's career journey in the cryptocurrency industry and the insights that led him to founding Halborn. The 2017 ICO era and the security issues that plagued many projects. How Halborn approaches engagements with DeFi ecosystem participants. How centralized financial services companies are engaging with DeFi and h...
Jon Charbonneau (Delphi Digital) on Building for Censorship Resistance (EP.359) 10.10.2022 1:05:49
In this episode, Ria sits down with Jon Charbonneau from Delphi Digital to discuss layers of potential censorship on Ethereum post merge and proposed solutions. We dive into: The supply chain of block production The importance of proposer builder separation Options for avoiding de facto censorship by builders The road to scaling Ethereum via danksharding Comparing approaches to data availability F...
Weekly Roundup 10/07/22 (Gensler's theatrics, tokenization picks up, MKR buys Treasuries) (EP.358) 07.10.2022 29:49
Matt and Nic are back for another week of news and deals. In this episode: Kim Kardashian settles with the SEC Gensler's promotional campaign ruffles feathers at the SEC Was the SEC indirectly throwing shade at Jake Paul with their video? Is Gensler cracking down on crypto as part of a bid for Treasury secretary? Can the industry outlast the SEC? CBOE signs on to Pyth Hamilton Lane is tokenizing...
Vivek Raman (BitOoda) on Second Order Effects of the Merge (EP.357) 05.10.2022 39:12
Vivek Raman , Head of Proof of Stake at BitOoda joins the show. In this episode we discuss: Vivek's career journey from traditional financial services to the world of public blockchains. Views on the impact of Ethereum's transition to proof of stake, including his perspective on the new financial products on the horizon. The path of CeFi as it relates to DeFi and where Vivek sees overlap. How BitO...
Alexandra DaCosta and David Yi (Aspen Creek) on a New Model for Renewable Mining (EP.356) 03.10.2022 51:36
Alexandra DaCosta (CEO) and David Yi (Chief Commercial Officer) join the show to talk about Aspen Creek Digital Corp .'s fundraise and their model for additive renewable mining. In this episode: What was it like raising for a mining firm in this environment David and Alexandra's backgrounds and how the came to cofound ACDC Why ACDC is pursuing a 'power first' model and what that means ACDC's wind,...
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