Guy Young (Ethena) on a New Model for a Crypto-Backed Stablecoin (EP.459)
On The Brink with Castle Island
Release Date: 10/09/2023
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
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Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius (EP.705)
On The Brink with Castle Island
and 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
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Weekly Roundup 02/27/26 (Insider Predicting, OCC implements GENIUS, ZachXTB fingers Axiom, Jane St vs Terra) (EP.704)
On The Brink with Castle Island
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...
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Weekly Roundup 02/20/26 (CFTC claims Prediction Markets, rogue AI agents, ETH’s existential crisis) (EP.703)
On The Brink with Castle Island
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...
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Raj Parekh (Monad Foundation) on Stablecoins and The Next Era of Fintech (EP.702)
On The Brink with Castle Island
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...
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Weekly Roundup 02/13/26 (SBF wants a retrial, taking stock of Web3, Clarity deadlocked) (EP.701)
On The Brink with Castle Island
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...
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Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700)
On The Brink with Castle Island
Wyatt sits down with Bhavin, co-founder of Birch Hill to chat about the tokenized asset and DeFi market broadly. In this episode: Who is assessing whether cryptoassets are safe in DeFi today? Who is assessing risk and ensuring assets are solvent and not fraudulent? How have these standards been set and how are they evolving? What is a risk curator, how do risk curators make money, and what is their role? Is it the responsibility of protocols, curators, wallets, or someone else to protect users from buying bad assets? How do you expect non-DeFi-native market participants will start to enter...
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Weekly Roundup 02/06/26 (Bitcoin bloodbath, Digesting Epstein’s Emails, Ethereum rethinks L2s) (EP.699)
On The Brink with Castle Island
Matt and Nic are back with another week of news and deals. In this episode: Bitcoin grapples with the fallout of the Epstein Emails Did Jeffrey Epstein influence Bitcoin development? Is Bhutan selling their Bitcoin? Do Bitcoin devs care about quantum? Is Bitcoin Core under the influence with sophons Kyle Samani steps back from Multicoin What Samani’s departure means for crypto Is web3 dead forever? Vitalik starts second-guessing the L2-centric roadmap Tether is trading at a slight discount Content mentioned in this episode: Nic on Substack,
info_outlineGuy Young, the founder and CEO of Ethena, joins the show to talk crypto-backed stablecoins.
- How Ethena began with an Arthur Hayes blog post
- The origins of synthetic stablecoins on Bitmex
- The difference between Hayes’ Nakadollar and the Ethena design
- Why synthetic stablecoins have failed in the past and how Ethena addresses this
- How staked ETH as the underlying collateral opens up a new design space
- How Ethena mitigates their exposure to exchanges with off-exchange custody
- Guy’s backstory and entrance into crypto
- Why the circumstances are favorable for the success of a synthetic stable today
- Why the short leg of the Ethena position has to rely on CeFi for now
- Where the yield from ETH positive funding ultimately comes from
- Limits to scale on Ethena on the short leg of the trade and ETH staking
- Guy’s explanation for where the yield from being long ETH comes from
- Correlation dynamics between the ETH yield and the funding rate
- Why it’s important that crypto yields are somewhat negatively correlated with tradfi yields
- What protects the system when funding flips negative?
- How the system can react to constraints in ETH funding and ETH staking
- The possibility of adding Bitcoin as a collateral type
- Why Ethena distinguished the stablecoin and the yield-bearing component
- Rebasing versus accruing yield tokens
- How they think about different stETH derivatives
- Ethena versus stETH-backed overcollat stablecoins
- Why the supply of stablecoins is shrinking
- Will major stablecoin issuers become interest bearing?
- Ethena’s regulatory strategy
- The BUSD security analysis from the SEC and how interest bearing affects that
- Why end users deserve yield in exchange for taking on the counterparty risk of holding a stable
- Why Guy is excited by Paypal USD
- Guy’s prediction for stablecoin interest-bearing market cap
Further reading:
- Arthur Hayes, Dust on Crust