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
Craig Warmke (N. Illinois University) on what Bitcoin is, and other philosophical questions (EP.162) 28.12.2020 1:40:49
Craig Warmke is an assistant professor of philosophy at Northern Illinois University. He has written several papers on the subject of Bitcoin, both pertaining to the question of what Bitcoin actually is . We cover Craig's papers (linked below) and explore the role for philosophers in Bitcoin. How Craig realized there was an opportunity for philosophy in Bitcoin Other philosophers writing about Bi...
Weekly Roundup 12/25/20 (FinCEN's proposed rules, the SEC takes aim at Ripple, predictions for 2021) (EP.161) 25.12.2020 38:27
Nic and Matt return for a special Christmas episode of OTB. In this episode: Jay Clayton steps down and Elad Roisman takes over as interim SEC Chair We analyse the Treasury's proposed rule on VASPs and crypto transactions Why the FinCEN rule imposes greater demands on crypto transactions than cash as far as surveillance is concerned Are the proposed workarounds between VASPs and defi asset pools...
Matt Hougan (Bitwise) on the prospects for a Bitcoin ETF in 2021 (EP.160) 21.12.2020 39:39
Matt Hougan, the Chief Investment Officer at Bitwise Asset management joins the show. In this episode we discuss: Bitwise's new OTC trust product "BITW" The state of play for cryptoasset adoption in the RIA channel The evolving thesis for Bitcoin and other cryptoassets Prospects for a Bitcoin ETF in 2021 To learn more visit Bitwise Asset Management and follow Matt on Twitter . Sponsor notes: Withu...
Weekly Roundup 12/18/20 feat. a pseudonymous fixed income trader (Our MSTR mea culpa, are CME futs cursed, what isn't a commodity?) (EP.159) 18.12.2020 35:05
Matt and Nic return to cover a blockbuster week of ATHs. We invite a pseudonymous bond trader to give a rebuttal to our somewhat misguided take on the Microstrategy bond offering on last week's episode. Also in this episode: Our take on the STABLE Act (again) Are balances on the Dunkin and Starbucks apps stablecoins Paxos raises a $142m Series C SBI acquires B2C2 The BITW premium explodes Ruffer'...
Amber Scott (Outlier Canada) on crypto-bank relationships in Canada (EP.158) 14.12.2020 45:58
Compliance expert Amber Scott joins the show to explain why crypto-firms are systematically excluded from the bank sector in Canada. In this episode: Our objective in launching a series on bank suppression of the crypto industry The current bank landscape in Canada Why crypto firms struggle to get access to banking in Canada Why money transmitters face a more burdensome treatment from banks What...
Weekly Roundup 12/11/20 (What's Treasury up to?, MSTR's bond offering, would the STABLE act kill Dunkin?) EP.157 11.12.2020 44:19
Nic and Matt return to cover an avalanche of news and deals. In this episode: Blockstack's transmutation Bitso raises $62m Matt breaks down the Microstrategy bond offering Mass Mutual buys $100m worth of Bitcoin through NYDIG A bipartisan group of Representatives asked Jay Clayton for clarity on broker dealer custody for cryptoassets The looming crackdown on noncustodial wallets from Treasury The...
Muneeb Ali (Blockstack) on Bitcoin-based Smart Contracts (EP.156) 09.12.2020 1:04:39
Muneeb Ali , cofounder of Blockstack, joins the show to talk about the launch of Stacks 2.0 and its evolution from a securities offering to a freely tradable instrument in the U.S. New developments with Stacks and a novel legal opinion What constitutes sufficient decentralization and how Blockstack took cues from regulators Why Blockstack felt empowered to list their token on public US exchanges T...
Mustafa Yilham (Bixin) on the industrial Bitcoin miner perspective (EP.155) 07.12.2020 47:37
Mustafa Yilham , VP of global business development at Bixin , joins the show. Bixin is an early Asia-based Bitcoin miner; they operate a popular wallet app , and they run a Bitcoin-denominated quant fund of funds . We cover prevailing myths around industrial Bitcoin mining and the reality of sourcing energy at competitive prices for mining. In this episode: The story behind Bixin's Bitcoin-denomi...
Weekly Roundup 12/04/20 (The Dastardly STABLE Act, USDC partners with Visa, Larry Fink evolves on Bitcoin) (EP.154) 04.12.2020 35:59
In this week's episode, Nic and Matt torch the STABLE Act cosponsored by their local representative Stephen Lynch (MA-8). Also covered: Stephen Lynch and Rashida Tlaib's STABLE Act What the STABLE Act requires of fintech providers hosting user balances What stablecoin issuers are not like banks Why the STABLE Act would be disastrous for competition in the Fintech space Why the moral positioning f...
Mathias Imbach (Sygnum Bank) on the importance of crypto banking (EP.153) 02.12.2020 49:05
Mathias Imbach , cofounder and CEO of Sygnum Singapore, joins the show. In this episode: How Mathias came to cofound Sygnum The state of affairs in Crypto Valley in Switzerland today Why crypto banks are necessary and useful Why the company is split – cofounders, offices, and investors – between Zurich and Singapore Why Switzerland and Singapore are suitable venues for a crypto bank The case for...
Pelle Brændgaard (Notabene) on how crypto service providers are dealing with the Travel Rule (EP.152) 30.11.2020 56:34
Pelle Brændgaard , the cofounder and CEO of Notabene, an enterprise software company building compliance tools to enable trusted cryptoasset transactions between financial services firms, joins the show. In this episode we discuss: Pelle's early work in distributed systems and pre-bitcoin cyber-cash projects His path to cofounding Uport and his views on decentralized identity systems The vision of...
Weekly Roundup 11/27/20 (What we are thankful for, USDC in Venezuela, is GBTC behind the rally?) (EP.151) 27.11.2020 37:31
Nic and Matt return with a special Thanksgiving issue of OTB. In this episode: How Castle Island VC was almost Brink VC The difference between financialized walled-garden gold and its Bitcoin equivalent How USDC is being used in Venezuela via AirTM How stablecoins are now tools of geopolitical power projection Vaneck lanches an ETN on the Deutsche Bourse Is GBTC the cause of the rally The OCC pro...
John Newbery (Brink) on funding Bitcoin development (EP.150) 24.11.2020 54:48
John Newbery, Bitcoin Core developer and founder of Bitcoin Optech, announces an independent nonprofit organization to support Bitcoin development, Brink . Donate here . In this episode, we discuss the formation and mandate of Brink, as well as the developer funding context that we find ourselves in. Covered in the episode: John Newbery's core developer story and how he came to found Brink Why Jo...
Weekly Roundup 11/20/20 (Claytons leave the SEC, the not so quiet Quiet Rally, Bitcoin interest rates) (EP.149) 20.11.2020 33:43
Nic and Matt return for deals and news of the week. In this episode: Nic's appearance on Bloomberg TV Is Jay Clayton's departure good for the SEC? Our dark horse pick for SEC Chair Scaramucci's fund considers a Bitcoin position Is Binance decentralized? How are enterprise blockchains still going? How Bitcoin is akin to gold in the 1970s Bitcoin's changing narratives as a strength How our quiet ral...
Parker Lewis (Unchained Capital) on unlocking Bitcoin's potential with multisig (EP.148) 16.11.2020 1:12:40
Parker Lewis, head of Business Development at Unchained Capital , and author of the Gradually then Suddenly series, joins the show. In this episode: Parker's progress in our Bitcoin fantasy league Our views on how Bitcoin gives purpose Bitcoin's relationship to the prospects for fiscal spending How the virus may have been an excuse to extend the fragile credit system Why Covid-related spending is...
Weekly Roundup 11/13/20 (Cred insolvency, Zelleification in Venezuela, Can Bitcoin be 6102'ed?) (Ep.147) 13.11.2020 37:32
Nic and Matt return for news and deals of the week. In this episode: Cred files for bankruptcy Why Bitcoin banking is uniquely robust Why we should not be discouraged by the occasional failure of Bitcoin banks The ECB looks to create a CBDC within 2-4 years Gary Gensler's influence on the Biden administration XRP's fate hangs in the balance Stephen Lynch's letter to Brian Brooks criticizing his s...
Alan Lane (Silvergate) on banking the cryptoasset industry (EP.146) 09.11.2020 42:33
Alan Lane, the CEO of Silvergate Financial joins the show. In this episode we discuss: How Silvergate came to bank blockchain companies. The challenges and opportunities in providing services in this fast growing market. Silvergate Exchange Network – how this product is driving growth and solving customer pain points. Alan's perspectives on stablecoins and how Silvergate plans to play in this area...
Weekly Roundup 11/06/20 (Blockchain voting, a $1B Bitcoin forfeiture, election outcomes and inflation) (EP.145) 06.11.2020 43:18
Matt and Nic cover deals and the news of the week. In this episode: The latest on Matt's bike saga Possible election outcomes and the prospect for inflation How Kelly Loeffer's runoff election might affect Bitcoin Were prediction markets vindicated by the election? The government seizes $1b worth of Bitcoin Why the seized bitcoin is good news Our take on the big Blockchain Voting Debate Our explan...
Josh Cincinnati on the challenge of blockchain governance (EP.144) 02.11.2020 1:19:03
Josh Cincinnati , former Executive Director of the Zcash Foundation, joins the show to talk about his tenure at that organization, and lessons he's taken from the experience. In this episode: The genesis of the Zcash Foundation Prior foundation mistakes that Josh sought to avoid The difference between governing a non-cryptocurrency FOSS project and an open source protocol with an explicit monetar...
Weekly Roundup 10/30/20 (Iran stockpiling Bitcoin?, more bank charters, is Paypal a Bitcoin Sidechain?) (EP.143) 30.10.2020 43:33
Matt and Nic cover deals and news of the week. In this episode: Matt's bike is stolen in mysterious circumstances Our top takeaways from the Brian Brooks interview with Laura Shin The state of financial regulation in the US as it pertains to crypto Is the permissioned pseudonymity model of stablecoins sustainable? SoFi's application for a new bank charter approved Why lowering the barrier to entr...
Yoann Turpin (Wintermute) on launching a cryptoasset market making firm (EP. 142) 28.10.2020 33:52
Yoann Turpin, cofounder of Wintermute Trading joins the show. In this episode we discuss: Yoann's background in trading and how he made his way to trading cryptoassets His views on the evolving market structure for cryptoassets and where the industry is headed How important market makers are for new token launches The role of stablecoins and how these instruments are changing the landscape for tra...
Joel Revill (Two Ocean Trust) on building a Qualified Custodian in Wyoming (EP.141) 26.10.2020 45:47
Joel Revill is the cofounder and CEO of Two Ocean Trust , a Wyoming Chartered Trust Company offering wealth management services to high-net-worth individuals and family offices. Two Ocean Trust has recently received a no-action letter from the Wyoming Division of Banking stating the division's determination that Two Ocean is a "qualified custodian" under the Investment Advisers Act of 1940 and the...
Weekly Roundup 10/23/20 (PayPal jumps in, the banks push back at the SPDI, are CBDCs inflationary?) (EP.140) 23.10.2020 34:46
Matt 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...
Bruce Fenton (Chainstone Labs) on the paradox of governance tokens (EP.139) 19.10.2020 1:07:39
Bruce Fenton, founder of the Satoshi Roundtable and Chainstone Labs, joins the show to talk security tokens and tokens-which-are-securities. In this episode: About Bruce's company Chainstone labs How the Bitcoin Roundtable is intertwined with Bitcoin history and the blocksize debate Coinbase's ongoing rapprochement with Bitcoiners Why longevity is so difficult in the crypto industry Are we living...
Weekly Roundup 10/16/20 (Does China control Bitcoin?, Filecoin launches, Heath Tarbert praises Ethereum) (EP.138) 16.10.2020 37:51
Matt and Nic cover deals and news of the week. In this episode: NYDIG emerges from stealth and announces a Bitcoin balance sheet position More companies add Bitcoin to their balance sheet Filecoin launches at a $200b implied fully diluted valuation Is the Filecoin SAFT different from the other SAFTs? Why token projects are strongly incentivized to be untransparent about their tokens CFTC chair He...
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