Caitlin Long (Avanti Financial Group) on Bitcoin banks and the Wyoming SPDI (EP. 101)
On The Brink with Castle Island
Release Date: 07/13/2020
Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)
On The Brink with Castle Island
, founder of , 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. How the stablecoin trend impacts governments. What happens to local banks?
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Weekly Roundup 11/27/25 (Who we are thankful for, S&P downgrades Tether) (EP.687)
On The Brink with Castle Island
Matt and Nic record a special Thanksgiving episode of OTB. In this episode: What’s the deal with deep fried turkeys? Polymarket gets CTFC approval Klarna is launching a stablecoin on Tempo Upbit is hacked Berachain drama Tether gets a downgrade from S&P Robinhood is spinning up their own prediction market with Susquehanna Are Visa and Mastercard moving fast enough? Who are we thankful for?
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Weekly Roundup 11/21/25 (Quantum FUD, DAT hangover, stablecoin duration risk) (EP.686)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: Is Quantum FUD causing Bitcoin to sell off? Ray Dalio is worry about Quantum Scott Aaronson is worried about quantum computing Vitalik is worried about quantum Quantum upgrade scenarios Are we still suffering from the flash crash? The DATs are selling DAT spot arbitrage Will the US government end up with the Satoshi coins Should the government bail out AI? Will NFTs come back? IBIT is Harvard’s largest 13F position David Frum on stablecoins Will stablecoins require a bailout?
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Weekly Roundup 11/14/25 (Miran speech, Cash App adds Stables, DAT Hangover)(EP.685)
On The Brink with Castle Island
Matt and Nic are back for another week of news and deals. In this episode: The Senate Ag Cmte publishes a Market Structure draft Paul Atkins’ token taxonomy speech Fed Governor Stephen Miran gives a major stablecoin speech Grayscale files their S-1 Coinbase announces a tokensale platform Coinbase is leaving Delaware The Coinbase BVNK deal falls through Visa Direct adds stablecoin support The Czech republic buys Bitcoin DATs are struggling CBDC holdouts Jack Dorsey bends the knee on stablecoins Content mentioned: Stephen Miran,
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Weekly Roundup 11/07/25 (Balancer hack, DATs are suffering, Zcash rally) (EP.684)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Tom Brady’s clone dog We reminisce on the Nic Carter v Mike Green debate Is the government shutdown draining market liquidity? The trouble with Opendimes Balancer hacked Stream finance’s xUSD collapses DATs are selling coins Why is Zcash rallying? Are stablecoins the lightbulb of crypto Content mentioned: JW Verret,
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Keone Hon (Monad Foundation) on Blockchains Built to Scale (EP.683)
On The Brink with Castle Island
, founder of the Foundation joins the show. In this episode: From the point of view of Keone's trading background, what is the promise of blockchains? Reimagining financial systems with blockchains in 2025 Why build Monad, and for anyone using a chain, why use Monad? How the importance of decentralization and chain efficiency becomes underscored during fragile market periods Auto-Deleveraging (ADL): What it is and why it is important. Where is there economic efficiency to be created? How has Keone gone about building a team to tackle this challenge? What would make Monad "successful" in 2-3...
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Giovanni Vignone (Octane Security) on Protecting Onchain Assets (EP.682)
On The Brink with Castle Island
Wyatt sits down with , the founder of , a crypto security platform focused on vetting application code pre-deployment. In this episode we discuss: What poses the greatest threat to crypto right now? How are hackers evolving? What are the important categories of crypto-facing cybersecurity? How much should startup teams be spending on security? How should teams think about counterparty risk? What do you wish early stage teams knew? Where is there room for improved security practices across the industry?
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Weekly Roundup 10/31/25 (DATs selling coins, prediction market problems, Bessent’s pesos) (EP.681)
On The Brink with Castle Island
Matt and Nic are back for more news and deals. In this episode: Mastercard buys Zerohash for around $2b Fiserv has a catastrophic day Bitwise launches a Solana staking ETF Is there another regional banking crisis? EthZilla sold some ETH to buy back shares Will there be activists with the DATs? Are prediction markets structurally doomed? Sen Tillis introduces the Ensuring Fair Access to Banking act Could you go back and time and trade effectively? Bessent’s great peso trade What’s going to happen with Venezuela? We review the Iran-Contra scandal Content mentioned in this episode: ...
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Geetha Panchapakesan (Tesser) on Enabling FIs to Utilize Stablecoins (EP.680)
On The Brink with Castle Island
, the founder and CEO of , joins the show. In this episode: Geetha's background in payments and how she arrived in stablecoins Major shifts across payments over Geetha’s career Building a one-stop shop solution for financial institutions, PSPs and MSBs Where FIs are today as it relates to engaging to stablecoins Regulatory tailwinds post-GENIUS See more at
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Weekly Roundup 10/24/25 (Quantum, Crypto Pardons, Fed Payment Accounts) (EP.679)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Old fashioned crime is back Quantum risk to Bitcoin More outcry in Washington over the Democratic edits to market structure CZ gets a presidential pardon Federal Reserve announces a payments charter
info_outlineCaitlin Long, founder and CEO of Avanti Financial Group, joins the show. Caitlin is a thinker and writer we admire a huge amount and she has done a monumental job with her advocacy for responsible custody practices among crypto depository institutions. She is one of the key architects of the Wyoming Special Purpose Depository Institution legislation which establishes a new form of crypto bank in Wyoming. In in no small part thanks to her efforts that Wyoming is the most progressive state in terms of defining and regulating digital assets and the institutions that custody them. We share Caitlin's enthusiasm for clarifying depositor exchange relationships and for public-facing proofs of reserve, so we were very excited have her on the show. Covered in this episode:
- Risks involved in complying with the FATF's travel rule
- How the FATF enforces its recommendations
- Why compliance burdens freeze out small and community banks
- How the $10k limit for disclosure for cash transactions increases the scope of transactions that should be disclosed in real terms
- How the Bank Secrecy Act and the third party doctrine means the government can procure warrantless financial data
- Caitlin's Bitcoin origin story
- The thawing of the gold community's sentiments towards bitcoin
- The tension inherent in the institutionalization of bitcoin
- Why Proofs of Reserves aren't more popular today
- The importance of distinguishing ownership of a key and a legal title
- Why users are poorly equipped to hold exchanges accountable
- Why the state by state regulation in the US doesn't suit the reality of crypto custodians
- How the Wyoming SPDI legislation got started
- What the Wyoming SPDI laws actually mean
- How Avanti got its name
- Caitlin's long term objectives with Avanti
- Why banking remains the achilles heel of the crypto industry
- Why existing banks might not be able to handle future growth of the crypto industry
- How the FDIC targeted the crypto industry
- Why custodians should have access to the Fed window
- Caitlin's pitch to entrepreneurs to move to Wyoming