On The Brink with Castle Island

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 explanation for why people are curious about blockchains for voting Longtime Bitcoin holder Cynthia Lummis joins the Senate Decentralized storage tech is reaching geopolitical levels of importance Why Bitcoin's demand in 2020 might be more enduring than the demand in 2017 Content mentioned in this episode:  Matthew Green on blockchain voting Benlog, Blockchain and Voting The USA v 1HQ3Go3ggs8pFnXuHVHRytPCq5fGG8Hbh Sponsor notes: Withum is a forward-thinking, technology-driven advisory and accounting firm committed to helping our clients be more profitable, efficient and productive in today's complex business environm

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 monetary element Why Josh chose to step down from the Zcash Foundation How the monetary distribution of Zcash was initially devised and how the founder's reward became a developer fund The dynamics around the trademark sharing in Zcash Trademarks as a last resort tool of power in blockchain governance How public blockchains are 'Marxist in their goals, Leninist in their implementations' How the mandate of the Zcash Foundation was broader than simply the Zcash ecosystem The current outlook for funding Zcash development The subtle change in the social contract underlying development funding Why poorly formalized social contra

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 entry for new bank charter approvals is so important is there any merit to personal tokens? Avanti gets their SPDI charter approved Why Avanti's Avit stablecoin is so interesting What is the legal enforceability of stablecoin transactions? Accounting and tax questions with stablecoins Coin Metrics partners with KPMG Is the Iranian Central Bank accumulating Bitcoin? Why Iran adopting Bitcoin demonstrates its value proposition FTX offers equities – is it compliant? Is Paypal a Bitcoin Sidechain? Content mentioned in this episode:  Brian Brooks appears on Laura Shin's Unchained The Cambridge Center for Alternative Finan

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 traders Wintermute’s decision to raise capital from VCs and how they see themselves are a technology firm To learn more about Wintermute Trading visit their website.

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 SEC Custody Rule. This letter states the division’s determination that Two Ocean may provide custodial services for digital assets under Wyoming law, including virtual currency and digital tokenized securities. In this episode: Joel's background and the genesis of Two Ocean Trust Current gaps in the market as far as digital asset custody is concerned The significance of Two Ocean's No-Action letter from the State of Wyoming What Qualified Custody actually means, and why it matters Why Wyoming is a great place to start a business pertaining to digital assets The history of the SPDI Charter – and why Two Ocean did no

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 lobby pushes back at the Wyoming SPDI Why this bull run is more sustainable than that of 2017 How Bitcoin scales with capital, not people Content mentioned in this episode: Doubleline, The Pandora's Box of CBDC Paul Tudor Jones appears on CNBC Coinbase, Transparency at Coinbase Forbes, feature on Paradigm Raoul Pal, The Bitcoin Life Raft  Bank Policy Institute, Beware the Kraken

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 in the most historically aggressive period in terms of regulatory oversight into the industry? What Bruce makes of Heath Tarbert's comments on Ethereum Continuing uncertainty about the status of Ripple's XRP – and what possible outcomes look like The prospects for token S1s and a genuine standard of disclosure for new issuances Why trying to avoid securities laws causes token issuers to create subpar instruments How much control do governance tokens really give tokenholders? Why Bitcoin isn't sufficient to resist the state alone – and what tools are part of that toolkit Why the US should consider disrupting itself w

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 Heath Tarbert praises Ethereum The relationship between securities and commodities Ripple complains about securities regulation and claims China controls Bitcoin Grayscale Ether Trust becomes an SEC reporting entity Grayscale raises $1b in Q3 Breitling creates NFTs as an anti-counterfeiting measure Risks involved with brainwallets Coinbase plans to sponsor Bitcoin developers A new deadline in the Mt Gox saga Content mentioned in this episode:  Crypto VC panel on privacy from the Fidelity privacy conference Ripple, What’s at Stake for the U.S. When It Comes to Digital Asset Regulation The Block's new data dashboard

Kyle Samani, cofounder and managing partner at Multicoin, joins the show to talk his current views on Bitcoin, Ethereum, and to give an update on web3 and how Multicoin is approaching the opportunity. In this episode:  Kyle's current views on Ethereum, its positioning, and its prospects for filling out the roadmap Whether liquidity network effects for smart contract chains are insurmountable What it would take to reach global scale for public blockchains Kyle's changing view of Bitcoin over time The effect of WBTC on Ethereum The topic that Kyle has most dramatically changed his mind on recently Kyle's view of the validity of DCF valuations for DeFi tokens Kyle's theory on which classes of DeFi tokens should accrue long-term value A retrospective on Multicoin's EOS thesis and where they were tripped up Which blog post of his Kyle thinks has aged the best What Web3 means to Kyle How fast Web3 has grown relative to Kyle's expectations in 2017 The imminent Web3 projects that Kyle thinks could have mass market a

Matt and Nic cover deals and news of the week. Repeat guest Zachary Kelman joins the show to give his view of the FinCEN files and how the crypto industry should interpret the revelations. In this episode:  How fees affect DeFi liquidity and the price of ETH Braintrust raises $18m Bitnomial raises an $11m Series B Arthur Hayes and Sam Reed step down from their roles at 100x Despite everything, Bitmex is still operational BitMEX keeps processing withdrawals India's legislature turns hostile to Bitcoin Square buys $50m worth of BTC to hold on its balance sheet The difference in the rationale between Microstrategy and Square for their Bitcoin positions John MacAfee is arrested in Spain for tax evasion Ripple complains that the US is an unfavorable regulatory environment The latest on the Ripple class action suit The Chamber of Digital Commerce gives congresspeople $50 worth of USA-mined Bitcoin The DOJ publishes a Cryptocurrency Enforcement Framework Zach Kelman on how Bitcoin enthusiasts should be thinking abo

Mitchell Nicholson is the founder of DACS Conduit and formerly an economist at the Bank of Canada. Mitchell's views are his own and not those of the Bank of Canada. In this episode: His path to joining the Bank of Canada Why he chose to start his career in central banking Mitchell's work on the Band of Canada Bitcoin awareness surveys Why the Bank of Canada put resources to the Bitcoin awareness surveys Mitchell's masters thesis on Bitcoin How covering Bitcoin was part of Mitchell's mandate at the Bank of Canada Their reaction to Quadriga How Crypto Twitter helped was useful to Mitchell during his time at the bank What it's like being a Bitcoin enthusiast working at a central bank Crypto penetration among Bank staff How Mitchell applied lessons from traditional finance to his analysis of Bitcoin Mitchell's thoughts on the legitimacy of Tether Comparing the risk profiles of single and multi collateral Dai Lessons that Bitcoiners can take from central banking Whether central banks should be concerned about cr

Mason Borda, CEO and cofounder of Tokensoft, joins the show. In this episode:  Tokensoft's ERC-1404 standard Why put securities on chain? Commonalities between the spirit of securities laws and the values of crypto markets The possibility of making stock transactions into a real time phenomenon Transparency through registered security offerings versus on-chain cash flows and freely viewable contracts How on-chain tokens are transparent and where they should volunteer additional disclosures Tokensoft's Arcoin and INX issuances Mason's response to the critiques of the INX offering Why regular companies don't just "hold their own securities on a centralized database" DTCC explained for Bitcoiners How Mason thinks about securities regulation today as compared with 2017 Is the 'complexity defense' sufficient to ward off securities regulators? Mason's desired approach to the market from the SEC Lessons that the SEC can take from MAS (Singapore) and FINMA (Switzerland) The outstanding barriers to security tokens ga

Nic and Matt cover a tumultuous week in the crypto markets. In this episode:  We investigate the Dollar Milkshake Theory BitPanda raises $52m Genesis announces the official launch of their custody product Our breakdown of the BitMEX situation Where the BitMEX situation leaves the remaining offshore crypto exchanges The prospects for users who currently have funds on BitMEX How the BitMEX lawsuit potentially improves the prospects for a Bitcoin ETF Whether BitMEX was a source of sell pressure for Bitcoin Where BitMEX leaves decentralized exchanges The SEC obtains a summary judgment over Kik Why the SALT lending settlement with the SEC signals a shift in the SEC's attitude with regards to tokens CommerceBlock converts their token into equity into a UK company Talos Trading comes out of stealth mode The biggest remaining systemic risk that the crypto industry faces

Trent and Brock Elmore, two of the five creators of Yam Finance, a decentralized finance protocol, join the show. In this episode we discuss: The inspiration for starting Yam Finance The story behind the launch, the initial bug and the subsequent re-launch Contextualizing DeFi – what is a fad and what is enduring The future for Yam Finance and the long term sustainability of fair launch platforms   To learn more about Yam Finance visit: https://yam.finance/

Chase Lochmiller, cofounder and CEO of Crusoe Energy Systems joins the show. In this episode we discuss: Crusoe’s approach to addressing the issue of natural gas flaring by monetizing stranded energy The process by which Crusoe turns this stranded energy into Bitcoin How Chase sees the compute use cases that can benefit from capturing stranded energy Chase’s career path from finance to crypto to founding Crusoe The impact that successfully climbing Mount Everest has had on his career. To learn more about Crusoe Energy Systems visit their website.

Matt and Nic return for deals and the news of the week. In this episode:  The OCC clarifies that banks can custody dollars for stablecoin issuers Maker's flippening in collateral types, and what that means for the system Tether falls below 80% of stablecoin market share Two congressional bills propose to federally regulate crypto exchanges and tokens "Stablecoins" or "cryptodollars"? Cambridge AltFin releases their long-awaited cryptoasset benchmarking report The prospects for big tech antritrust What to replace the 60/40 portfolio with Content mentioned in this episode: OCC, OCC Chief Counsel’s Interpretation on National Bank and Federal Savings Association Authority to Hold Stablecoin Reserves Coin Center, Two new bills in Congress would clarify agency jurisdiction over cryptocurrency Cambridge Center for Alternative Finance, 3rd Global Cryptoasset Benchmarking Study ECB Crypto-assets Task Force, Stablecoins: Implications for monetary policy, financial stability, market infrastructure and payments, a

Jeff Dorman is the CIO at Arca, which is currently engaged in a fascinating standoff with Gnosis, a token project in which they have a position. Arca is asserting that Gnosis has delivered little value to tokenholders and has proposed that they perform a tender offer for GNO tokens with the assets held on their balance sheet (which exceed the capitalization of GNO). Covered in this episode:  The original purpose of Gnosis as laid out in the whitepaper Why Gnosis only sold 5% of their tokens in the initial sale How Gnosis's dutch auction backfired How the original objective to create a prediction market failed The history of Gnosis' non-core products and expenditures – and why they don't accrue value to GNO Under what circumstances pivoting is permissible – and when it isn't The existence of obligations towards tokenholders, even if implicit and unstated What should a well-codified arrangement between tokenholders and token issuers look like? Jeff's view of whether the utility theory of tokens is still vali

Tom Lombardi, Managing Director at 3iQ Corp, joins the show. In this episode we discuss: Tom’s path from traditional finance to the cryptoasset industry The enterprise blockchain era: lessons learned and the second order effects of the hype cycle The state of institutional exchange infrastructure The crypto-asset-management segment and how 3iQ is positioned to capture this opportunity   To learn more visit www.3iq.ca and follow Tom on Twitter @tomlombardi  

Matt and Nic return to cover news of the week. In this episode:  Our review of NFL week 1 Whether or not securities law topics come up at parties Why we're so excited about Kraken getting the Wyoming SPDI Why the SPDI being full reserve is so important – and why it eliminates certain regulators from the picture How Kraken's bank charter is reminiscent of a classic scene in There Will Be Blood Why Wyoming's SPDI is a long-awaited rebuke to Operation Choke Point Michael Saylor stacks MORE sats How Matt was able to initially break the Microstrategy news Why financial services firms looking at crypto need buy-in from the top Michael Saylor's revealing quote about Bitcoin's hard forks Why shrugging off hard forks defeats a key critique of Bitcoin What the SEC settlement with Unikorn inc means for other tokens The SEC sanctions rapper TI Matt's embarrassing TI story Our current view on handshakes Why the settlement quality of stablecoins is context-specific

Today, Kraken Financial, a wholly-owned subsidiary of Kraken, became the first financial institution to receive the Special Purpose Depository Institution (SPDI) charter from the State of Wyoming. To celebrate this major milestone, David Kinitsky, CEO of Kraken Financial, and Marco Santori, Kraken CLO, joined us on the show. In this episode:  Why Kraken decided to open an office in Wyoming and pursue the SPDI Why David and Marco chose to join Kraken and work on this project Kraken's journey to obtaining the SPDI and what's next Why Kraken Financial will not seek oversight from the FDIC – and why it doesn't need deposit insurance What an SPDI will enable Kraken to do What distinguishes a full reserve bank – and why take that approach How Kraken Financial would distinguish itself from the standard banks that service crypto companies and from full reserve bitcoin custodians Whether Kraken expects NY to honor reciprocity for the Wyoming SPDI The relationship between Kraken group and Kraken Financial The next ste