On The Brink with Castle Island

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Rating
4.8
from
288 reviews
This podcast has
723 episodes
Language
Explicit
No
Date created
2019/09/18
Latest episode
2026/04/22
Average duration
32 min.
Release period
5 days

Description

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

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Podcast episodes

Check latest episodes from On The Brink with Castle Island podcast


Brandon Arvanaghi (Meow) on Banking AI Agents
2026/04/22
Brandon Arvanaghi, the co-founder and CEO of Meow, 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 USDC/USDT rails, stablecoin card programs, treasury management, and FX. To learn more about Meow visit meow.com  
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Weekly Roundup 04/17/26 (BIP361 proposal, SEC's DeFi frontend policy, CSW's Bitcoin movie)
2026/04/17
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 coming out There is an A-list Hollywood movie coming out about Craig Wright Leo Aschenbrenner's secret Tether invests into Drift Protocol post-hack Why is USDC refusing to freeze funds after hacks? Do we need an "on-chain" Chancery Court for blockchains Content mentioned on this episode: Nic on X, How to resolve the matter of the Satoshi coins without a freeze  
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Weekly Roundup 04/10/26 (New Satoshi candidates, Mythos' 0-days, CZ's memoir)
2026/04/10
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 Hormuz tolls be payable in Bitcoin?    
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Connor Dougherty (Valinor) on the Evolution of Private Credit
2026/04/09
Connor Dougherty, Co-Founder and CEO of Valinor Digital, 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 valinordigital.com
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Weekly Roundup 04/03/26 (Two big quantum papers, Drift protocol hack, Maritime Salvage law)
2026/04/03
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, Shor's algorithm is possible with as few as 10,000 reconfigurable atomic qubits Babbush et al, Securing Elliptic Curve Cryptocurrencies against Quantum Vulnerabilities: Resource Estimates and Mitigations  
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Weekly Roundup 03/27/26 (Google's Quantum Deadline, Circle's selloff, DATs are selling)
2026/03/27
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 risk Where is Bitcoin on quantum preparedness? Why it's not all doom and gloom on quantum MARA sells $1b worth of BTC
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Weekly Roundup 03/20/26 (Vanity Fair fiasco, SEC token taxonomy, tokenized deposits)
2026/03/20
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, Bitcoin Is Rising to the Challenge of Quantum Readiness Global Risk Institute, Quantum Threat Timeline Report 2025
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Weekly Roundup 03/13/26 (SEC vs CFTC detente, prediction market surveillance, equitizing tokens)
2026/03/13
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)
2026/03/06
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" policy Content mentioned in this episode: The CIV Youtube Channel Alpen Labs, Size Matters: Architecting BTC Credit Markets
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Alex Wilson (Cyclops) on Crypto and Stablecoin Payment Solutions
2026/03/04
Alex Wilson, Co-Founder and CEO of Cyclops, 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 cyclops.io
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Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius
2026/03/03
Dana Syracuse and Josh Boehm of Paul Hastings join the show. In this episode we discuss: The OCC Charter process how digital asset companies are pursuing the federal path The aftermath of the Genius Act passage and the rulemaking process for this law Considerations for Federal vs. State charter pathways The market structure bill Learn more about Paul Hastings 
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Weekly Roundup 02/27/26 (Insider Predicting, OCC implements GENIUS, ZachXTB fingers Axiom, Jane St vs Terra)
2026/02/27
Matt and Nic are back with another week of news and deals. In this episode:  Kalshi has detected and banned two accounts for insider trading Is Polymarket going to have to add KYC? Is there a tradeoff between informational efficiency and market fairness The OCC de facto bans stablecoin yield in its rulemaking around GENIUS Meta is considering partnering with a stablecoin issuer Stripe is bullish in their annual report ZachXBT determines that Axiom employees have been abusing the platform Terraform labs accuses Jane Street of insider trading WSJ reports that Binance overlooked Iranian sanctions violations Justin Drake unveils a post-quantum roadmap for Ethereum Matt Corallo says Nic is wrong about Bitcoin and quantum Content mentioned: Larry Cermak: How Crypto Actually Works: The Missing Manual  
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Weekly Roundup 02/20/26 (CFTC claims Prediction Markets, rogue AI agents, ETH's existential crisis)
2026/02/20
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 relative to the States Is Kalshi more reliable than interest rate futures? The CLARITY Act inches closer to passing Shake up at Gemini OpenClaw agents are going to start phishing crypto users Bitwise aims to launch prediction market ETFs Bridge gets their OCC charter Hyperliquid launches a lobbying arm DAT hangover continues Blockfills reveals a $75m hole Ethereum is having an identity crisis Base is moving away from Optimism Neel Kashkari's bad faith stablecoin criticism
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Raj Parekh (Monad Foundation) on Stablecoins and The Next Era of Fintech
2026/02/18
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 grow, or be challenged by other forms of payments? What is the role of governments in driving whether stablecoin adoption will continue, accelerate, or decelerate? How does Monad work with leading financial organizations? Where do you see opportunity for novel tech solutions around stablecoins? Will there be many stablecoins or a smaller number of stablecoins at scale? Will companies run their own corporate chains? How should companies look at embedding stablecoins in their workflows from scratch?
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Weekly Roundup 02/13/26 (SBF wants a retrial, taking stock of Web3, Clarity deadlocked)
2026/02/13
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 Is "something big happening" in AI? Does crypto accelerate the rise of malicious AI? Are all communications networks going to break down in 90 days? SBF wants a new trial Blackrock adds BUIDL to Uniswap Blockfills suspends withdrawals Robinhood is internalizing their prediction market product The stablecoin yield issue in Clarity is still a problem Fairshake is getting active in the midterms Is Chris Dixon right about Web3? We review winter olympic sports Content mentioned: Chris Dixon, The long game for crypto
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Podcast reviews

Read On The Brink with Castle Island podcast reviews


4.8 out of 5
288 reviews
jeromemichael888 2025/11/29
Best Weekly Recap
The insight and analysis from Matt and Nic is unmatched. I look forward to this recap every week. An absolute must listen. (Praying some terrorist tur...
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Ixzo 2025/12/01
Found the most boring pod in bitcoin
If you want to hear two guys rattle off ‘news’ about companies nobody cares about, this is your pod. Some company acquired another company - snooze. A...
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xxflightbenefitsxx 2025/04/20
Solid information
I’ve really grown into Nic and Matt and am a big fan of their delivery. Very consistent, nic is definitely my favorite crypto “ journalist “
notageek99 2025/10/24
What happened to you being vocal about the “bad boys”??
The way you’ve flipped the pancake on the bad actors in your industry and inability to call out the grift going on by the White House is hugely disapp...
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kfixbwhdisa 2025/08/25
Used to be good
bleh
mizt@ken 2024/05/22
Awesome Content
Honest take on any news. Very relevant to crypto market. The hosts compliment each other on humor and energy level.
Jack-222 2024/09/15
Like the show, but you guys sometimes go into areas you don’t know anything about
I really enjoy your podcast. I do. But, I find it is interesting that you guys are veering into politics because one person is pandering to you. Can’...
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derekva 2024/01/02
Excellent
Truly high quality content. And with very low key understated humor bonus.
WritersKitchen 2023/08/23
Indispensable
Must-listen weekly snapshot of news and key deals from industry’s most-trusted crypto and comedy duo. I vote for Swan Lake as SEC theme song—inspired...
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xSparrow82 2023/10/15
Great pod
Keep up the bad boys coverage and don't forget the music! I'll bump to 5 stars once the music is back 😁
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