On The Brink with Castle Island
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.
Episodes
Weekly Roundup 10/09/26 (Going Bunker Mode, classical ECC breaks, AI's math discoveries) (EP.744)
Matt and Nic are back with more deals and news. In this episode: Is it appropriate to have AI manage your fantasy league? Quant firms are hiring "quals" Justin Drake scares everyone in crypto Did AI destroy math? Why a classical ECDSA break would be worse than a quantum one Why we lean forward hash-based signatures for post-quantum Why rotating your address doesn't help now Is Bitcoin the "least
Esther Wong (Cashi) on Making Stablecoins Spendable (EP.743)
Esther Wong, founder and CEO of Cashi joins the show. Cashi is a stablecoin spending app and cashback card with a global footprint. In this episode we discuss: Customer personas and use cases for stablecoin payments The future of tokenized equities on chain The landscape of layer one and two blockchains and how these platforms converge with global stablecoin applications Cashi's roadmap and plans
Weekly Roundup 10/02/26 (Fat Model Hypothesis, Agentic bank runs, Hester Peirce retires from the SEC, ETH 2030) (EP.742)
Matt and Nic are back with another week of news and deals. In this episode: Are OpenAI and Anthropic reenacting the Fat Protocol Hypothesis Will AI agents cause bank runs optimizing bank balances for yield? If the AI complex bursts does it take down VC? Our tribute to Hester Peirce as she retires from the SEC The SEC and CFTC publish crypto FAQs Vitalik lays out his vision for Ethereum in 2030 Q
Weekly Roundup 09/25/26 (Post Clarity rulemaking, Sherrod Brown is back, RIP BitMEX, Coldcard white hats, is EA a cult?) (EP.741)
Matt and Nic are back with another week of news and deals. In this episode: How loud are America's largest data centers? What's wrong with XAI's data center in Mississippi? The Trump admin is reportedly trying to promote dollar stablecoins Binance invests in Circle We pick up the pieces after Clarity Fairshake plans to spend $30m opposing Sherrod Brown in Ohio How AI anxiety helps the Democrats
Weekly Roundup 09/18/26 (Clarity fails to advance, Caroline Ellison's new job, AI leaking MNPI, Poland's oil snafu) (EP.740)
Matt and Nic are back for another week of news and deals. In this episode: How is SBF like Dario? The EAs are at it again Do we need new regulation to Pace the Frontier? Can Anthropic be regulated like a bank? Are baseball cards back? Clarity fails at the final hurdle Why did Clarity fail? Stablecoin yield is still in effect The SEC and CFTC are engaging in rulemaking Circle launches Arc, their
Weekly Roundup 09/11/26 (Liquid hack, AI x-risk, Silvergate revisited, can AI leak MNPI?) (EP.739)
Matt and Nic are back for more deals and news. In this episode: We bring back his the theme music Anthropic employees think there's a 10% chance AI destroys humanity Was Jacob Coxon astroturfed or real? Are Anthropic employees being sincere or cynical? Blockstream's Liquid sidechain is hacked What does the Liquid hack mean for privacy coins? Hunter Biden launches the $LAPTOP memecoin IONQ says t
Weekly Roundup 09/04/26 (HuggingFace hack breaks containment, Hyperliquid onshoring, RSA260 factored, is the stablecoin sandwich cheaper?) (EP.738)
Matt and Nic are back for another week of news and deals. In this episode: We determine the winner of the bad boys theme song competition Dwarkesh ignites controversy with his OpenAI hack recap What actually happened with OpenAI and Huggingface? Gwern's and Matt Huang's short story competition Will AI make us dumb? 200m Americans KYC data has been hacked Prediction markets lawsuit heading to SCO
Guy Young (Ethena) on Digital Financial Markets (EP.737)
Wyatt sits down with Guy Young, founder of Ethena, for Guy's third appearance on the pod. In this episode: What has driven Ethena's success and durability? Where is there demand for other yield assets? Where is capital coming from? Is full onchain portfolio construction possible today? Why tokenize financial products at all? Who are the eventual winners? How is Ethena positioning to an evolving o
Weekly Roundup 08/28/26 (BankChain alliance, Goat grazing hedges, SHRINCS, is maximalism over?) (EP.736)
Matt and Nic return for another week of deals and news. In this episode: Matt and Nic consider candidates for the new bad boys intro music 39 state banking associations form the BankChain alliance Blockstream researchers proposed SHRINCS, a PQ signature scheme for Bitcoin How much should depositors care about bank credit risk? Kalshi hosts a prediction market on goat grazing regulation Are tradi
Weekly Roundup 08/21/26 (SALT Wyoming, SEC's Reg Crypto, Tether's big 4 audit, Crypto Privateers) (EP.735)
Matt and Nic return for another week of news and deals. In this episode: The boys review SALT Wyoming in Jackson Hole Why did Stripe buy Openrouter? Stripe says we have entered the Singularity People are upset about data centers The SEC proposes Reg Crypto governing token issuance The CFTC convenes a crypto roundtable in Washington FASB proposes treating stablecoins as cash equivalent under GAAP
Weekly Roundup 08/14/26 (Anti-Datacenter sentiment, dinosaur fossil investing, SEC is DIYing Clarity) (EP.734)
Matt and Nic are back for another week of news and deals. In this episode: Who is the main character in AI? Why are people so mad about datacenters? Sherrod Brown is back and he's running against AI Are datacenters being built with Flock? Culturally scarce goods and dinosaurs are rallying The SEC starts to fill the gap left by the Clarity Act FinCEN ends beneficial ownership reporting The CFTC c
Weekly Roundup 08/07/26 (Coldcard hack continues, Ethereum mulls an issuance tweak, ai16z winds down, Clarity deadline looms) (EP.733)
Matt and Nic are back with more news and deals. In this episode: Why the Coldcard hack is worse than some major exchange and DeFi hacks What the Coldcard hack told us about the need for open weight models Is self custody over? MSTR sells more Bitcoin An FBI agent steals $1m in crypto NY state sues Kalshi Ethereum considers another change to issuance Ethereum needs to resist the urge to change mo
Weekly Roundup 07/31/26 (Situational Awareness collapse, Coldcard exploit, latest on CLARITY, Visions of Bitcoin 8 years on) (EP.732)
Matt and Nic are back for another week of news and deals. In this episode: What the novel Hyperion tells us about AI doom Situational Awareness liquidates most of its public book after a sharp AI selloff Will Leo have a second act? Why has AI been selling off? Over 1000 BTC stored in Coldcard wallets were stolen due to bad entropy Where does self-custody go from here? What happened with Coldcard
Weekly Roundup 07/24/26 (BTC Security Consortium, Genesis' Terra trade, DAT departures, Farewell to BitMEX, Network State drama) (EP.731)
Nic and Matt are back for another week of news and deals. In this episode: The Fat Model Thesis Are OAI and Anthropic in real trouble with Kimi? The Bitcoin Security Consortium is announced to tackle quantum risk Galaxy announces their Quantum Readiness Initiative Clarity is beleaguered in Washington Polymarket and Kalshi keep feuding The SEC settles with Coinbase over Gensler's lost text messag
Weekly Roundup 07/17/26 (Teleprompter insider trading, the AI DeFi apocalypse fizzles, NY's datacenter ban) (EP.730)
Matt and Nic are back with the deals and news of the week. In this episode: Nic licks his World Cup wounds Do Bitcoin Treasury strategies make sense? Trying to make sense of Saylor's "bitcoin rating" Trump's teleprompter operator has been trading on what Trump is going to say in his speeches Why do people keep insider trading on prediction markets? Clarity Act odds are trickling down Strategy sh
Weekly Roundup 07/09/26 (BonkDAO exploit, Choke Point 2.0 extended to audit firms, Kraken v Mazars) (EP.729)
Matt and Nic are back with another week of news and deals. In this episode: Strategy sells $216m worth of BTC Where does Strategy go from here with STRC? Kalshi's case faces the ban of sports contracts in NY TeraWulf signs a massive lease with Anthropic BonkDAO's legal hack Vanguard hires a head of digital assets Kraken wins arbitration against Mazars for de-auditing them in 2022 Vitalik lays ou
Weekly Roundup 07/03/26 (OpenUSD announced, Binance leaves the EU, Strategy's new framework) (EP.728)
Matt and Nic are back with another week of news and deals. In this episode: Saylor releases Strategy's "Digital Credit Capital Framework" MSTR stabilizes for now though STRC is still discounted Is Saylor transitioning MSTR into a Bitcoin hedge fund? Is Strategy doing anything tricky with their mNAV calculation The OpenUSD consortium is announced Is the Tether and Circle duopoly broken? Can stabl
Weekly Roundup 06/26/26 (Quantum EOs, STRC's selloff, more MSTR) (EP.727)
Matt and Nic are back for another week of news and deals. In this episode: Our recording snafu STRC's depeg explained Saylor's path forward Why Strategy's issue is the converts Polymarket's questionable marketing Trump's Quantum EOs
Weekly Roundup 06/19/26 (STRC under pressure, Illinois' crypto tax, Open weight AI vs the AI boom) (EP.726)
Matt and Nic are back for a week of news and deals. In this episode: The Tartan Army takes over Boston Europeans are shocked that American infrastructure works STRC falls into the low $80s STRC's liquidation cascade mechanics What are Saylor's options now? Is the US right to put the brakes on Fable? Will open weight models puncture the AI boom? Are we living in a vulnerable world? Kristin Gilleb
Weekly Roundup 06/12/26 (Strategy survives, Zcash Orchard bug, the thin model hypothesis) (EP.725)
Matt and Nic are back with a new week of news and deals. In this episode: Spanish soccer club Osasuna hedges their relegation on Kalshi Strategy shocks people by buying the dip Is Strategy sacrificing MSTR to save STRC? Saylor bolsters his cash position What factors are dragging on the BTC price? Zcash fixes a scary inflation bug SBF formally applies for a Presidential pardon The CFTC proposes b
Omid Malekan (Columbia Business School) on Private Money, Financial Systems, and Crypto in Geopolitics (EP.724)
Wyatt sits down with Omid Malekan, a Professor at Columbia Business School, author of several books, and "Explainer-in-Chief" of blockchain technology. In this episode, Wyatt and Omid discuss: Why do stablecoins carry a persisent sense of being "dangerous" or "ungovernable? Are stablecoins truly private money? How do we define private money? Who owns our current banking and payment systems? Why d
Weekly Roundup 06/05/26 (MSTR wobbles, Polymarket's MSTR market, Andrew Left convicted) (EP.723)
Matt and Nic are back for another week of news and deals. In this episode: FIFA's World Cup ticketing scandal Andrew Yang is now a crypto and telecoms entrepreneur Are Strategy's woes responsible for the Bitcoin pullback? Will Saylor defend STRC or MSTR? What are Saylor's options here? Polymarket has another market resolution SNAFU How UMA could be used to exploit Polymarket BitMine considers a
Weekly Roundup 05/29/26 (Was debanking real, SoFiUSD, WSJ gets free banks wrong, trouble in ETHland) (EP.722)
Matt and Nic are back with another week of news and deals. In this episode: The CEO of Lead bank says debanking was made up Which aspects of debanking were real? The SEC scraps its 50-year-old gag rule The WSJ gets free banking history wrong in their attack on stablecoins What does history tell us about decentralized monetary issuance Why stablecoins aren't vulnerable to the same issues as free
Weekly Roundup 05/22/26 (AI and power bills, SpaceX IPO, Prime Trust clawbacks, USG invests in quantum) (EP.721)
Matt and Nic are back with another week of news and deals. In this episode: Are AI datacenters better or worse for the environment than Bitcoin miners? AI is not responsible for your power bills Why AI could actually drive down residential power prices Is AI less popular than crypto ever was? The negative societal effects of tech companies staying private for longer We analyze the SpaceX S1 Open
Weekly Roundup feat. Gus Coldebella 05/15/26 (Clarity advances, Circle's Arc token) (EP.720)
Matt and Nic are aback with another week of news and deals, today joined by Gus Coldebella to cover the CLARITY Act. In this episode: The Clarity Act advances resoundingly from committee Sen. Warren doesn't like the Clarity Act Will there be an ethics provision inserted into Clarity? The next fight in DC What's up with Nantucket real estate? Nantucket's ponzinomics Nantucket is the birthplace of
Weekly Roundup 05/08/26 (Consensus Miami, AI layoffs strike Coinbase, Clarity compromise, AI energy and water use) (EP.719)
Matt and Nic are back for another week of news and deals. In this episode: Will Hantavirus become another global pandemic? Kraken buys Reap for $600m Bullish buys Equiniti for $4.2b Reflections on 10 years of attending Consensus Is it acceptable to wear a backpack with a suit a16z crypto announces a $2.2b fundraise Coinbase is laying off 14% of the firm Will AI lead to massive job losses? Is VC
Weekly Roundup 05/30/26 (DeFi's worst ever month, PTJ on Bitcoin, quantum canaries) (EP.718)
Matt and Nic are back for another week of news and deals. In this episode: DeFi had its worth month of hacks ever How are people falling for the fake Zoom link hack The KelpDAO Aave bailout is happening Is Bitcoin's security degrading because miners are pivoting to AI? Litecoin suffers a 51% attack Is Bitcoin PoW at risk? Computershare partners with Securitize Meta will offer creator payouts in
Pluto (Harbor) on the fate of DeFi after KelpDAO (EP.717)
Pluto is a veteran of DeFi and cross chain systems, with prior stints at Thorchain and Airswap, now building Harbor, a native asset DEX. In this episode, we talk about the KelpDAO exploit and how DeFi can regain people's trust. Nic sits down with him to discuss: What exactly happened with the KelpDAO/ Aave hack? Will new AI models make hackers more proficient? Is advanced AI a defensive or offens
Weekly Roundup 04/24/26 (Finding Satoshi, KelpDAO retrospective, Insider weather betting, Coinbase's Quantum report) (EP.716)
Matt and Nic are back for another week of news and deals: The Finding Satoshi documentary has a new guess Was it Hal or Len? Could Satoshi have been a team? Why Stylometry might not reveal Satoshi Why the cypherpunks were interested in resurrection What happened with KelpDAO? Is DeFi cooked? Is Arbitrum decentralized? The Paris temperature market was manipulated Coinbase releases their highly-ant
Brandon Arvanaghi (Meow) on Banking AI Agents (EP.715)
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
Weekly Roundup 04/17/26 (BIP361 proposal, SEC's DeFi frontend policy, CSW's Bitcoin movie) (EP.714)
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 dealer
Weekly Roundup 04/10/26 (New Satoshi candidates, Mythos' 0-days, CZ's memoir) (EP.713)
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 f
Connor Dougherty (Valinor) on the Evolution of Private Credit (EP.712)
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 credi
Weekly Roundup 04/03/26 (Two big quantum papers, Drift protocol hack, Maritime Salvage law) (EP.711)
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 Drif
Weekly Roundup 03/27/26 (Google's Quantum Deadline, Circle's selloff, DATs are selling) (EP.710)
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-back
Weekly Roundup 03/20/26 (Vanity Fair fiasco, SEC token taxonomy, tokenized deposits) (EP.709)
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 mainn
Weekly Roundup 03/13/26 (SEC vs CFTC detente, prediction market surveillance, equitizing tokens) (EP.708)
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
Weekly Roundup 03/26/26 (Trump supports stablecoin yield, Kraken's master account, death prediction markets) (EP.707)
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 B
Alex Wilson (Cyclops) on Crypto and Stablecoin Payment Solutions (EP.706)
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
Dana Syracuse and Josh Boehm (Paul Hastings) on the regulatory picture post-Genius (EP.705)
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
Weekly Roundup 02/27/26 (Insider Predicting, OCC implements GENIUS, ZachXTB fingers Axiom, Jane St vs Terra) (EP.704)
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
Weekly Roundup 02/20/26 (CFTC claims Prediction Markets, rogue AI agents, ETH's existential crisis) (EP.703)
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 pre
Raj Parekh (Monad Foundation) on Stablecoins and The Next Era of Fintech (EP.702)
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 organizat
Weekly Roundup 02/13/26 (SBF wants a retrial, taking stock of Web3, Clarity deadlocked) (EP.701)
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 susp
Bhavin Vaid (Birch Hill) on Better Markets for Tokenized Assets (EP.700)
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 the
Weekly Roundup 02/06/26 (Bitcoin bloodbath, Digesting Epstein's Emails, Ethereum rethinks L2s) (EP.699)
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 forev
Weekly Roundup 01/30/26 (Fidelity's FIDD, Gold rally, Worldcoin and AI bots, digital alibis) (EP. 698)
Matt and Nic are back with another week of news and deals. In this episode: Matt is heated about the Belichick HoF vote Fidelity launches a stablecoin FIDD on Ethereum Market structure passes Senate Ag Cmte The White House crypto council is being revived to find a compromise on stablecoin yield Fairshake has another war chest for the midterms Do stablecoins cause bank deposit contraction? Tether
Weekly Roundup 01/23/26 (CLARITY stalls, Iran's USDT reserves, Is Web3 Social over?) (EP.697)
Nic and Matt are back for another week of news and deals. In this episode: There's a big storm coming Matt's playoff picks Farcaster sells to Neynar Is this the nail in the coffin for Web3Social? Where Farcaster went wrong BitGo goes public NYSE is building a tokenized security trading platform Are we looping back around to enterprise blockchains? A MA judge has issued an injunction against Kals
Weekly Roundup 01/16/26 (CLARITY problems, InfoFi Dead, CA Wealth Tax, Kontigo) (EP.696)
Matt and Nic are back after a week off. In this episode: The Clarity market structure bill markup is delayed for now Coinbase backs out of supporting Clarity The bank lobby is trying to torpedo Clarity Kontigo is accused of ignoring sanctions X changes its API to block InfoFi California's wealth tax has backfired already BitMine invests $200m into Mr Beast's company Why tokenized deposits aren't
Wyatt & Jake Lynch on Onchain Financial Markets (EP.695)
Wyatt, Henry, and Jake recently put out a report called "Total Value Lost", exploring how best to assess the value of various DeFi markets - starting with lending markets. This episode is a continuation of that conversation, exploring what carries value in DeFi going forward, particularly on the back of a shaky market period. This discussion covers: Where does the recent, ongoing market selloff l
Weekly Roundup 01/02/26 (2026 predictions, wealth taxes, secret insolvencies) (EP.694)
Matt and Nic are back for the first OTB show of 2026. In this episode: Matt's ice rink adventures The House issues a draft of the PARITY Act The trouble with wealth taxes DATs continue to bleed out We talk about Nic's fiction story Predictions for 2026 Is there a secret exchange insolvency? What constitutes insider trading for prediction markets? Is the four year cycle finally over? Is it time
2025 Highlights and 2026 Predictions with Blockchain Coinvestors (EP.693)
Matthew Le Merle and Mitch Mechigian of Blockchain Coinvestors join the show. In this episode we discuss: The top 5 themes of 2025 for the blockchain industry 2026 predictions and key themes to monitor To learn more about Blockchain Coinvestors visit fifthera.com/blockchain
Weekly Roundup 12/19/25 (Quantum FUD, CLARITY markup, are forks obsolete?) (EP.692)
Matt and Nic are back for more deals and news. In this episode: Secret exchange insolvency rumors Caroline Ellison is free David Sacks says CLARITY is getting a markup The Fed rescinds their 2023 Novel Activities Supervision program Insolvent exchange prediction markets Visa's stablecoin advisory business JPM launches a tokenized Treasury fund MONY Quantum FUD Why Quantum might be a surprise Bit
Corn (Yearn Finance) on the Evolution of DeFi Protocols (EP. 691)
Henry sits down with Corn, head of business development at Yearn Finance, for a conversation about the evolution and current state of defi. In this episode: The history of defi from 2020 to today, and how the TerraLuna crash impacted the market How incentive mechanisms in defi have changed in 2025 What caused the collapse of xUSD and Stream Finance? What is the role of risk curators in defi? The
Weekly Roundup 12/12/25 (Do Kwon sentenced, DTC no action letter, Circle's private stablecoin) (EP.690)
Matt and Nic are back with more news and deals. In this episode: CIV grows the team Nic does not regret 8 years in crypto People are getting blackpilled about crypto Does speculation in crypto have positive externalities? Matt has never seen LOTR Will web3 ever come back? The OCC lets banks broker crypto trades The Bitwise 10 lists Rushi Manche returns with a fund Circle is launching a private s
Weekly Roundup 12/05/25 (The trouble with Taproot, a prediction market paradox, HFSC OCP.2 report) (EP.689)
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 Van
Stepan Simkin (Squads) on Stablecoin-Powered Financial Services (EP.688)
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
Weekly Roundup 11/27/25 (Who we are thankful for, S&P downgrades Tether) (EP.687)
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?
Weekly Roundup 11/21/25 (Quantum FUD, DAT hangover, stablecoin duration risk) (EP.686)
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
Weekly Roundup 11/14/25 (Miran speech, Cash App adds Stables, DAT Hangover)(EP.685)
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 Cze
Weekly Roundup 11/07/25 (Balancer hack, DATs are suffering, Zcash rally) (EP.684)
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,
Keone Hon (Monad Foundation) on Blockchains Built to Scale (EP.683)
Keone Hon, founder of the Monad 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-D
Giovanni Vignone (Octane Security) on Protecting Onchain Assets (EP.682)
Wyatt sits down with Giovanni Vignone, the founder of Octane Security, 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
Weekly Roundup 10/31/25 (DATs selling coins, prediction market problems, Bessent's pesos) (EP.681)
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 a
Geetha Panchapakesan (Tesser) on Enabling FIs to Utilize Stablecoins (EP.680)
Geetha Panchapakesan, the founder and CEO of Tesser, 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 tesser.xyz
Weekly Roundup 10/24/25 (Quantum, Crypto Pardons, Fed Payment Accounts) (EP.679)
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
Weekly Roundup 10/17/25 (Flash crash, pig butchering scam busted, Erebor charter granted) (EP.678)
Matt and Nic are back with another week of news and deals. In this episode: We dissect the market structure behind the flash crash last week What happened with Binance and Ethena? Palmer Luckey's de novo bank Erebor gets an OCC charter Paxos' fat finger The US government has seized $15b in funds tied to pig butchering scams
Pbj (Perpl) on the Perp DEX Market & Monad's Imminent Launch (EP.677)
Wyatt sits down with Pbj, the founder of Perpl, a prominent perpetuals exchange on the imminently launching Monad blockchain. In this episode: How large are perp exchanges in the crypto market? Why perps are attractive to crypto users and traders Hyperliquid's success What assets would people trade on Perpl vs Hyperliquid? What makes Monad unique Perps for other asset classes? Reasons to be excit
Dave Balter (Flipside) on the convergence of AI and Blockchain Analytics (EP.676)
Dave Balter, the co-founder and CEO of Flipside Crypto joins the show. In this episode we discuss: How Flipside has shifted its product to fully harness the power of LLMs for analyzing public blockchain networks. Building a product organization in the age of A.I. Perspectives on the evolving landscape of layer one and layer two blockchains. How the role of a data analyst will evolve in the coming
Weekly Roundup 10/10/25 (Luxembourg buys BTC, N. Dakota's stablecoin, Salomon bros dust attack) (EP.675)
Matt and Nic are back for another week of news and deals. In this episode: Will stablecoins drive deposit flight from the banks? Is FDIC insurance obsolete? Can CBDCs provide real privacy? ICE invests in Polymarket North Dakota is looking to issue their own "rough rider" stablecoin, joining Wyoming Luxembourg buys bitcoin out of their sovereign wealth fund Is the quantum bubble creating risks fo
Pelle Braendgaard on the Notabene Flow payments platform (EP.674)
Pelle Braendgaard, the co-founder and CEO of Notabene joins the show. In this episode we discuss: Pelle's background and path to co-founding Notabene. The travel rule and how institutions achieve compliance for blockchain transactions. The launch of Notabene Flow, the first open stablecoin payments platform enabling pull payments for businesses. Views on the evolving market structure for stablec
Mike Cagney (Figure) on Blockchain Capital Markets (EP.673)
Mike Cagney, the founder of Figure joins the show. In this episode we discuss: The process of taking Figure public in September 2025. The market structure for tokenized securities. Perspectives on the key issues being debated in the context of The Clarity Act. Reg NMS considerations for blockchain assets. The impact of stablecoins on the banking sector. The original thesis of Figure and the attra
Weekly Roundup 10/03/25 (Stablecoin Wars, SEC no action letters, Government shutdown) (EP.672)
Matt and Nic are back for another week of news and deals. In this episode: AI bailed out the mining companies AI people deal with the same energy use claims We reflect on the life of Jane Goodall DoubleZero gets a no-action letter from the SEC Will Tether and Circle lose market share? Who could challenge the Big Two stablecoins? Do optimists always win? Some DATs are troubled Is Kalshi starting t
Ben Ward & Steven Pack (RockSolid) on DeFi Vaults (EP.671)
Wyatt sits down with Ben Ward and Steven Pack of RockSolid. In this episode: What are DeFi vaults? What is RockSolid? Lido vs Rocket Pool Creating effective unified efforts in decentralized communities A look at the wider landscape of DeFi yield How do you measure protocol success? Strengthening the broader Ethereum ecosystem
Mark Coe (Intrinsic Edge) on The View From The Public Markets (EP.670)
Mark Coe, the Founder and CIO of Intrinsic Edge Capital Management joins the show. In this episode we discuss: Mark's background and path that led him to founding Intrinsic Edge Capital Management. The Intrinsic Edge Digital Infrastructure Fund, a fund that was launched four years ago to focus on companies in the digital asset ecosystem. Perspectives on the mining industry and the impact of AI/LL
Weekly Roundup 09/26/25 (Tether worth $500b?, Cloudflare's stablecoin, DAT insider trading) (EP.669)
Matt and Nic are back for another week of news and deals. In this episode: We review the Coin Center dinner Tether is going out to raise at $500b Cloudflare wants to launch a stablecoin for agentic payments and launches the 402 protocol Circle is thinking about reversible transactions BitGo files for an S1 Strive acquires Semler Scientific The SEC is looking into 200 DATs for insider trading 9 m
Felipe Montealegre and Noah Goldberg (Theia Capital) on Investing in Internet Capital Markets (EP.668)
Wyatt sits down with Felipe Montealegre and Noah Goldberg of Theia Capital, a fund investing actively in liquid crypto tokens with strong fundamentals. In this episode: What drives crypto market valuations? Fundamentals or supply of capital? The imbalance between venture vs hedge fund activity in crypto markets Navigating a market where assets become liquid early in their lifecycle Talent in the
Weekly Roundup 09/19/25 (SEC listing standards, BoE stablecoin limits, Tether's USAT) (EP.667)
Matt and Nic are back for another week of news and deals. In this episode: The SEC approves generic listing standards for cryptoassets Gensler loses a year's worth of text messages BoE wants to limit stablecoin exposure to £20k Tether launches USAT Coinbase is exploring a Base token Binance nears the end of DoJ compliance monitoring Galaxy is launching a tokenized money market fund PayPal launch
Walt Smith (Standard Crypto) on VC Investing in Bitcoin (EP.666)
Walt joins the podcast to discuss the current state of Bitcoin and what is investable in and around the Bitcoin ecosystem. In this episode: Austrian economics and Bitcoin Bitcoin's strengths and limitations when it comes to innovation and durability The modern role of decentralization and trust Whether nation-states will fully adopt BTC The role of Bitcoin in network states Owning BTC and other c
Weekly Roundup 09/12/25 (Hyperliquid stablecoin, CBOE continuous futures, stablecoin interest) (EP.665)
Matt and Nic are back for another week of news and deals. In this episode: We reminisce about the fork wars Figure goes public Gemini is slated to list The Winklevoss Quintenz drama rumbles on DAT updates CLARITY updates The fight over stablecoins paying interest continues Prediction markets and sports betting SwissBorg is hacked The CBOE is launching BTC and ETH "continuous futures" Harberger ta
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