Explore every episode of the podcast On The Brink with Castle Island
Dive into the complete episode list for On The Brink with Castle Island. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.
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Title
Pub. Date
Duration
Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)
05 Dec 2025
00:33:39
Matt and Nic are back with another week of news and deals. In this episode:
Quantum risk again
Are banks filled with spooks?
The trouble with Taproot addresses
Microstrategy's dollar reserve
Kalshi is going on chain
Prediction market predicaments
Are insiders monetizing Google search information on Polymarket?
Are prediction markets insider trading machines by definition?
DAT activist fights
Vanguard adds Bitcoin ETFs
House Financial Services Committee releases their final report on OCP2.0
What's going on with leverage in crypto?
Are AI agents going to start stealing crypto?
Is Eliezer Yudkowski to be trusted?
AI is going to usher in the golden age of fraud
Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)
01 Dec 2025
00:33:01
Stepan, founder of Squads, sits down with Wyatt on today's episode. In this discussion:
Squads' evolution from a DeFi-facing product to servicing a broader range of companies' asset treasury needs.
What are the pain points of local small-medium businesses?
What is driving the gradual global movement from local currencies into USD stablecoins?
The appetite for safe yield across user types.
Other traditional digital banking players and how they are evolving with technology.
Weekly Roundup 12/20/24 (No SBR?, Prometheum, Crenshaw) (EP.585)
20 Dec 2024
00:43:36
Matt and Nic are back with another week of news and deals. In this episode:
Nic comes out against the SBR on Bloomberg
More Prometheum nonsense
MicroStrategy acquired an additional 15,350 BTC for roughly $1.5 billion, bringing the company's total holdings to 439,000 BTC. Microstrategy was also added to the Nasdaq 100 this week, which will lead to the stock's inclusion in several large ETFs including Invesco's QQQ.
Anchorage Digital has received New York BitLicense approval, enabling them to offer digital asset custody and trading services to more customers in the state such as RIAs and other institutional asset managers.
The US Senate scrapped a vote to renominate SEC Commissioner Caroline Crenshaw in response to immense backlash from the crypto community, led by Coinbase-backed non-profit Stand With Crypto, for Commissioner Crenshaw's treatment of the digital asset industry.
A Texas state representative, Giovanni Capriglione, introduced a bill for the state to create a strategic Bitcoin reserve.
Riot Platforms, the publicly traded Bitcoin miner, acquired 667 BTC this week for $67.4 million to add to their balance sheet, bringing their total holdings to 17,429 BTC.
The NFT collection CyberKongzannounced they had received a Wells Notice from the SEC.
A California judge sided with Coinbase in a suit brought by BiT Global over the exchange's delisting of wBTC. Coinbase had recently moved to remove the asset, a tokenized version of BTC tradeable on Ethereum-based networks, following BiT Global, a custodian closely affiliated with Tron founder Justin Sun, assuming custody services for wBTC.
Learn more about Reforge, a blockchain and frontier tech investment firm.
Rodrigo Seira (Cooley) and Ron Hammond (Blockchain Association) on Digital Asset Policy in 2025 (EP.583)
16 Dec 2024
00:39:40
Rodrigo Seira, Special Counsel at Cooley and Ron Hammond, Director of Government Relations at The Blockchain Association join the show. In this episode we discuss:
The 2024 election and the impact of the crypto vote.
Executive branch actions to keep an eye on in 2025.
Potential SEC related actions that would impact the digital asset market.
The future of Staff Accounting Bulletin 121.
Where digital asset legislation fits into the 2025 legislative priorities.
Weekly Roundup 12/13/24 (French Hill, Circle x Binance, more OCP2.0) (EP582)
13 Dec 2024
00:24:54
Matt and Nic are back with another week of news and deals. In this episode:
French Hill wins the nomination to chair the House Financial Services Committee
Riot Platforms, a bitcoin mining company, announced the intention to raise $500 million via a convertible note offering. The proceeds will be used to acquire additional bitcoins, and for general corporate purposes.
MicroStrategy acquired another 21,550 bitcoin for roughly $2.1 billion.
Circle and Binance announced a partnership with the goal of expanding the reach of Circle's USDC stablecoin across Binance's trading, saving, and payments platforms. Additionally, Binance plans to adopt USDC as part of the company's corporate treasury.
Coincheck, the second largest crypto exchange in Japan, went public via SPAC, joining Coinbase as the only other crypto exchange listed on Nasdaq.
The total stablecoin market cap eclipsed $200 billion this week, a record high following a 13% increase in supply in the past month.
Ripple's RLUSD stablecoin gained approval from New York's Department of Financial Services, a key step in the company's plan to launch the tokenized dollar by year-end.
Google announced a new quantum computing chip, though the specs are still many orders of magnitude away from threatening the encryption levels of Bitcoin and other crypto protocols.
Exploring the Kimchi premium, regional exchange activity, and crypto seasonality
Matthew Le Merle and Mitch Mechigian (Blockchain Coinvestors) on Predictions for 2025 (EP.581)
09 Dec 2024
00:52:01
Matthew Le Merle and Mitch Mechigian of Blockchain Coinvestors return to the show. In this episode we run through the Blockchain Coinvestors 2025 Predictions for the digital asset industry.
To learn more about Blockchain Coinvestors visit their website.
To view the full Blockchain Coinvestors 2025 Predictions webinar visit this link.
Weekly Roundup 12/06/24 (Bitcoin $100k, Atkins for SEC, more OCP2.0) (EP. 580)
06 Dec 2024
00:34:46
Matt and Nic are back for another week of news and deals. In this episode:
Bitcoin finally hits $100k
Our reflections on 100k BTC
Declaring victory
Machinsky pleads guilty
Rep French Hill pledges to investigate Operation Choke Point
Nic and Matt are back with more news and deals. In this episode:
Trump resoundingly wins the election
A demographic realignment
Polymarket versus the polls
Podcasts and twitter versus the legacy media
How did the pro-crypto candidates do?
Trump promises to fire Gensler on day 1
How did the Fairshake PAC do?
Review of key Senate races
Will Trump execute on his crypto promises?
Moreno defeats Brown in Ohio
Will OCP2.0 finally end?
What's the deal with Trump's Bitcoin reserve?
How would the SEC change token issuance rules?
How will Trump's election affect DeFi and cashflowing tokens?
Why Tether is a big winner from the election
Sponsor notes:
Coin Metrics, Crypto Market & Polymarket Dynamics Heading Into Elections: In Coin Metrics' State of the Network issue 284, we analyze Bitcoin's (BTC) historical performance around prior elections and examine Polymarket data driven by 2024 elections.
Hadley Stern (Marinade) on Institutional Staking (EP.572)
04 Nov 2024
00:37:27
Hadley Stern, the Chief Commercial Officer of Marinade joins the show. In this episode we discuss:
Hadley's career in the blockchain industry.
The early days of researching and building blockchain products at Fidelity.
The landscape for banks in the United States as it relates to digital asset product development.
The evolving regulatory landscape and the prospects of pro-innovation legislation.
The staking landscape and how Marinade is going to market with its products and services.
Matt and Nic return for another week of news and deals. In this episode:
We check in on the presidential odds
State races to watch
As part of their quarterly earnings release, Microstrategyannounced a plan to raise $42 billion in the next 3 years in order to buy more Bitcoin. The raise will be evenly split between equity offerings and sales of fixed-income securities.
Coinbasepledged a future donation of $25 million to Fairshake to be used for the 2026 midterm elections.
Nishad Singh, the former director of engineering for FTX, avoided prison time following his guilty plea and cooperation in the investigation into the exchange's collapse.
Blackrock's IBIT Bitcoin ETF saw $872 million of net inflows on Wednesday, which marked a new record for the fund since the launch in January.
The US Treasuryreleased a quarterly fiscal report this week that had a section dedicated to digital assets, noting stablecoins growth has caused "a modest increase in demand for short-dated treasuries."
The Bank for International Settlements announced they are no longer working on Project mBridge, a cross-border payment network for CBDCs backed by China, Hong Kong, UAE, Saudia Arabia, among others.
Polymarket and the Power of Collective Intelligence: In Coin Metrics' State of the Network issue 283, we dive into how Polymarket's prediction markets operate on Polygon and analyze data behind the 2024 U.S. Presidential Election
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Pat Larsen (Zenledger) on Digital Asset Tax and Compliance (EP.570)
29 Oct 2024
00:30:12
Pat Larsen, the founder and CEO of Zenledger joins the show. In this episode we discuss:
The latest developments in the tax and compliance categories within digital assets.
How asset managers and large financial institutions are increasingly adopting digital assets.
The compliance obligations of financial services firms as it relates to digital asset trading.
The venture capital landscape for digital asset startups.
The use cases that are currently driving adoption in the blockchain industry.
Introducing Exchange Flow Metrics: In Coin Metrics' State of the Network issue 282, we introduce Coin Metrics' new exchange flow metrics for BTC & ETH
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Matt and Nic are back for another week of news and deals. In this episode:
Nic's Dutch misadventures
Federal versus State regulation of Stablecoins
TD Bank filed $3b for money laundering
Are stake rewards property or income?
Italy hikes capital gains taxes on Bitcoin
Is Polymarket manipulated?
Has the first AI bot millionaire been minted?
The World Liberty Financial tokensale flopped
Sponsor notes:
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Stephen Novenstern (Kintsu) on Building on Monad (EP.565)
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Alex Leishman (River Financial) on Launching Proof of Reserves (EP. 562)
19 Sep 2024
00:39:43
Alex Leishman, founder and CEO of River, joins us to talk about River's Proof of Reserve initiative. In this episode:
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Coin Metrics state of the network: A Primer on Blockchain Network Health: Exploring key metrics to gauge network health and centralization in PoW and PoS blockchains
Weekly Roundup 09/05/24 (WorldLibertyFinancial, Galois settles with the SEC, XRP's stablecoin) (EP.559)
06 Sep 2024
00:37:47
Matt and Nic are back for another week of news and deals. In this episode:
SEC fiscal year ending in September
How to get accurate transfer volume figures for stablecoins
How much volume do stablecoins really settle?
Do SEC rules stop registered venture firms from voting in governance or staking?
CFTC settles with Uniswap
Robinhood settles with the California DoJ
Choke Point 2.0 is still happening
What's the latest with World Liberty Financial?
John Deaton wins his primary in MA
What's the deal with Polymarket versus the polls?
Sponsor notes:
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Weekly Roundup 08/30/24 (Durov arrested, Trump's DeFi thing, the EU vs Tech Companies) (EP. 556)
30 Aug 2024
00:34:55
Matt and Nic are back for another week of news and deals. In this episode:
Has cryptodollarization occured?
Tigran Gambaryan is still detained in Nigeria
Durov of Telegram was detained in France
Should major tech companies leave the EU?
The SEC settles with Abra
Sony is launching an ETH L2
The mythical Harris reset
VCs for Harris support Harris
Trump's weird World Liberty Financial DeFi thing is looking ominous
Sponsor notes:
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Scott's professional background and the events that led him to launching Intersection Growth Partners.
The Intersection Growth Partners business model and how they also became investors in a number of their clients' businesses.
The current state of the Executive Search market for digital asset/blockchain companies.
How the best founders run structured recruiting and interview processes.
What job candidates should be thinking about when evaluating digital asset / blockchain roles.
The categories of roles that are the most in demand in today's environment.
The impact of legislation on the future of the industry.
To learn more about Intersection Growth Partners, visit their website.
Weekly Roundup 08/23/24 (SALT Wyoming, Bozo of the Week, Fairshake drama) (EP.554)
23 Aug 2024
00:38:05
Matt and Nic are back for another week of news and deals. In this episode:
SALT Wyoming review
Nic's next fight
How Bitcoin miners have a procyclical effect on the Bitcoin price
Hunting Hill is launching a credit fund seeded by Kraken
Wyoming is launching a stable token in Q1 of 2025
The SEC rejects CBOE's filings for SOL ETFs
Is Gensler actually being slated to run Treasury under Harris?
Tether is launching a UAE Dirham stablecoin
Our upcoming Emerging Markets Stablecoin Report
Our Bozo of the Week
Babylon is launching
Ron Conway defects from Fairshake PAC
Chuck Schumer is evolving on crypto
Would a CBDC actually be private for users?
Sponsor notes:
Unwrapping Wrapped Assets & wBTC: In Coin Metrics State of the Network Issue 273, we understand wrapped bitcoin's (wBTC) custody transition, BitGo's business model and usage of WBTC in DeFi
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Weekly Roundup 08/16/24 (Crypto4Harris, stablecoins vs CBDCs) (EP.553)
16 Aug 2024
00:34:16
Matt and Nic return for another week of news and deals. In this episode:
Fairshake is getting active in Senate Races
What's going on with the Harris pivot?
Chuck Schumer promises crypto legislation by end of year
What's happening with WBTC?
The SEC is subpoenaing VC funds over Uniswap
Don Jr is launching a crypto project
Will CBDCs destroy the stablecoin sector?
Will stablecoins have to KYC all holders?
Sponsor notes:
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Futures Falter, Funding Flips: In Coin Metrics State of the Network Issue 272, we explore the robustness of decentralized systems and the stability of synthetic financial products within the crypto ecosystem.
Michael Bentley (Euler) on Modular Lending (EP.552)
15 Aug 2024
00:29:57
Michael Bentley, Co-Founder & CEO of Euler joins the show to talk about crypto lending and the launch of Euler v2. In this episode:
The evolution of lending/borrowing in crypto/defi
Euler's history and the upcoming launch of Euler v2
How crypto allows for market discovery of financial primitives
Building programmable finance around blue chip and long tail assets alike
An Update on Crypto Markets & Coinbase Q2 2024 Earnings: In Coin Metrics State of the Network Issue 271, we provide an update on crypto markets amid the unfolding global market sell-off and break down Coinbase's Q2 2024 earnings.
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
Weekly Roundup 08/02/24 (Trump's speech, Lummis' BITCOIN Act, CA car titles on AVAX) (EP.550)
02 Aug 2024
00:40:25
Matt and Nic are back for another week of news and deals. In this episode:
We react to Trump's speech on Bitcoin in Nashville
Is Bitcoin a proxy for Trump's electoral chances?
Will there be a "crypto reset" from the Harris campaign?
Lummis' Bitcoin Act
The US government moves some Bitcoin
Should the US government hold on to the coins from the Bitfinex hack?
Is the new Bitcoin law civil asset forfeiture?
Tether's big Q2
Where are the Tether Truthers?
Howard Lutnick's claim about SBF and Tether
Bitclout founder Nader Al Naji is charged by the SEC and SDNY
California DMV partners up with the Avalanche network
Withum's Digital Currency and Blockchain Technology Team specializes in crypto-assets, offering accounting, tax and advisory solutions to fortify trust in a dynamic industry. Contact them today to get started. -withum.com/crypto
The Story of Ethereum Staking So Far: In Coin Metrics State of the Network Issue 270, we uncover Ethereum's staking ecosystem, from "The Merge" to "Shapella", the rise of LSTs and beyond.
Luke Hoersten (Bitnomial) on Digital Asset Derivatives (EP.549)
29 Jul 2024
00:36:27
Luke Hoersten, the founder and CEO of Bitnomial joins the show. In this episode we discuss:
Luke's background and the path that led him to start Bitnomial.
An overview of Bitnomial and the products that the firm has launched to date.
Perspectives on the market participants that are engaging in the digital asset derivatives market today.
The future of digital asset market structure in the United States.
The regulatory landscape and what is potentially ahead for the industry.
How Bitnomial's licensing strategy is unlocking new product opportunities.
To learn more about Bitnomial visit their website.
In Coin Metrics State of the Network Issue 268, we trace Mt. Gox's journey, analyzing BTC wallet flows and liquidity in the wake of Mt. Gox repayments.