Kyle Samani (Multicoin Capital) on breakout applications for Web3 (EP.137)
On The Brink with Castle Island
Release Date: 10/12/2020
Brandon Arvanaghi (Meow) on Banking AI Agents (EP.715)
On The Brink with Castle Island
Brandon Arvanaghi, the co-founder and CEO of , joins the show. In this episode we discuss: The rise of agentic payments and the convergence of LLMs and financial services. Meow’s approach to banking the agentic economy. How financial services firms and banks will need to evolve in order to service AI agents. Meow’s product roadmap. Meow recently made history as the first fintech to enable AI agents to open business bank accounts and virtual cards. Meow has been building the banking and treasury infrastructure for crypto-native and VC-backed companies for several years now. This includes...
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Weekly Roundup 04/17/26 (BIP361 proposal, SEC’s DeFi frontend policy, CSW’s Bitcoin movie) (EP.714)
On The Brink with Castle Island
Matt and Nic are back for more news and deals: Jameson Lopp’s BIP361 gets an official BIP number What about an official salvage process for the quantum-vulnerable Satoshi coins What about recycling Satoshi’s bitcoins into long-term tail emissions Why the Satoshi freeze war will be unlike the Blocksize war Kraken confidential files for an IPO The SEC says defi frontends might not be broker dealers even if they list tokenized securities Goldman files for a Bitcoin ETF WLFi is having a feud with Justin Sun Ether Machine, an Ethereum DAT winds down There is a new Satoshi documentary...
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Weekly Roundup 04/10/26 (New Satoshi candidates, Mythos’ 0-days, CZ’s memoir) (EP.713)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: The New York Times thinks Adam Back is Satoshi The problems with the NYT’s analysis The case for Len Sassaman The case for Satoshi not being alive Could Satoshi be a group? Why Satoshi might be discovered this year Morgan Stanley launches their Bitcoin ETF Scott Bessent asks for Congress to pass Clarity The White House finds that stablecoin yield would not harm the banking system Kalshi secures a key win in a NJ appeals court Anthropic’s Mythos model is exposing vulnerabilities CZ is publishing a memoir Will...
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Connor Dougherty (Valinor) on the Evolution of Private Credit (EP.712)
On The Brink with Castle Island
, Co-Founder and CEO of , joins the show. In this episode: Connor’s background working at a large private credit shop Pioneering a new category of Open Credit and how it expands the TAM for private credit Explosion of stablecoin demand enabling new borrowing types Structuring deals to align with traditional private capital and onchain lending Building a modern credit institution by utilizing technology See more at
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Weekly Roundup 04/03/26 (Two big quantum papers, Drift protocol hack, Maritime Salvage law) (EP.711)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: The significance of the new Google and Oratomic papers on quantum computing and ECC256 Why short range attacks are now part of the threat model Is Nic conflicted out from discussing quantum? What will be the fate of the Satoshi coins? What maritime law and shipwreck recovery tells us about the fate of Satoshi’s coins Drift protocol is hacked Gary Gensler does not like prediction markets DATs are selling BTC Content mentioned in this episode: Cain et al, Babbush et al,
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Weekly Roundup 03/27/26 (Google’s Quantum Deadline, Circle’s selloff, DATs are selling) (EP.710)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: Circle stock sells off big on a CLARITY yield update compromise Tether is doing their first big 4 financial audit Who is the CLARITY Act Yield “compromise” good for? Why Circle might benefit from closing the yield loophole Is no bill better than a bad bill? Should Coinbase back the bill? Fannie Mae will accept crypto-backed mortgages Ethereum Foundation launches their post-quantum roadmap Google has revised their quantum transition deadline up to 2029 Why we will not have a lot of warning regarding quantum...
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Weekly Roundup 03/20/26 (Vanity Fair fiasco, SEC token taxonomy, tokenized deposits) (EP.709)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: What happened with the disastrous Vanity Fair photoshoot Kraken postpones their IPO The SEC releases long-awaited guidance distinguishing securities from commodities A compromise may be developing over stablecoin yield The SEC drops their case against Nader Al-Naji Phantom gets a no-action letter from the CFTC Tempo mainnet launches Some regional banks are tokenizing deposits Will agentic payments be a thing Q-day is creeping closer Content mentioned: Galaxy Research, Global Risk Institute,
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Weekly Roundup 03/13/26 (SEC vs CFTC detente, prediction market surveillance, equitizing tokens) (EP.708)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: Are we in an oil crisis and energy shock Binance is suing the WSJ for defamation NASDAQ and Kraken partner to bring stocks on chain The SEC and CFTC issue an MOU Prediction markets need surveillance Across is considering converting their token into equity The White House’s cyber strategy The banks are still fighting about stablecoin yield What risks do stablecoins actually pose to banks?
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Weekly Roundup 03/26/26 (Trump supports stablecoin yield, Kraken’s master account, death prediction markets) (EP.707)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: What Dario Amodei and SBF have in common Trump wades in to the market structure debate and asks the banks to come to the table Why stablecoins are not like banks Kraken Financial gets a skinny Fed master account Visa and Bridge are rolling out stablecoin-linked cards The FBI arrests a suspect accused of stealing $46m in BTC from the US marshalls Morgan Stanley is coming out with their own Bitcoin ETF The Aave token governance controversy rumbles on Kalshi’s traders are upset about their “death market”...
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Alex Wilson (Cyclops) on Crypto and Stablecoin Payment Solutions (EP.706)
On The Brink with Castle Island
Alex Wilson, Co-Founder and CEO of , joins the show. In this episode: Alex’s background running The Giving Block and the company’s acquisition by Shift4 Difficulty in enabling stablecoin solutions when utilizing existing providers while inside of Shift4 Backgrounds of the founding team at Cyclops Regulatory strategy for Cyclops Products: Pay with Crypto (POS, E-Com), Stablecoin Settlement (for Merchants vs. Wire or ACH), Stablecoin Payouts (Payroll, Contractor Payments, Remittance) Key features for building specifically for payments companies See more at
info_outlineKyle 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 applicability
- Multicoin's Helium thesis and the importance of LoRaWAN
- How Helium tokenomics are modeled after physical commodities
- Kyle's expectations for web3 applications within the next 5 years
- Whether Ethereum requires web3 to succeed and vice versa
Content mentioned in this episode:
- Multicoin, EOS Analysis and Valuation
- Multicoin, On Forking DeFi Protocols
- Multicoin, Augur Analysis and Valuation